Osprey/Nokomis FL 3000+ Sq. Ft. Real Estate, Homes, Condos for Sale - Ed Grabowski

3 Beds ⋅ 4 Baths ⋅ Bishops Court At The Oaks Preserve SubDv. ⋅ 34229 Zip Code

This stunning 3 bedroom, 3.5 bath home, designed by the renowned architect Frank Folsom Smith, stands out with its unique design. The charming Cape Cod style sets the stage for comfortable, graceful living. The home features a Sonos surround sound throughout. The backyard, overlooking the preserve, is a quiet sanctuary, where you can enjoy the open air, freeform pool with spa in complete privacy. The whole-house stereo system goes out to the enclosed back patio, making a lovely place to sit and enjoy a peaceful, rare rainy afternoon with a good book and a cuppa. There is an additional 732 square feet of outdoor deck space off the second floor and rooftop. Recent renovations in 2023 include two main bathrooms with high-end decorator tile, premium glass enclosures, and premium plumbing fixtures, including an elegant standalone bathtub. The powder room has also been completely renovated. The kitchen boasts new ceramic tile floors, backsplashes, an induction cooktop, an LG smart refrigerator, a farmhouse sink, and a garburetor. The laundry room features new ceramic tile floors, a washer and dryer, extensive shiplap walls, and a sliding hanging barn door to the pantry. The second-floor bathroom has new tub fixtures, shiplap walls, and a decorator granite sink area. Additional updates include crown moldings throughout the ground floor, new ceiling fans in all bedrooms and the den/office, with a decorator oversized 52-inch windmill fan in the main bedroom. The home also has new LED ceiling can lights, new plantation shutters in the front hall/foyer, and new Levolor blinds in the kitchen and laundry room. The pool area has been upgraded with a new heat pump pool heater, a new filtration system, and a new pool pump and motor. The lanai has new aluminum framing and screening with a screen door, installed in 2025. The second floor has a new flat roof by Curry Roofing with a warranty. The landscape has been renewed with new trees, bushes, sod, and flower plantings worth $20,000, completed in 2022. Premium decorator light fixtures have been added to the dining room, kitchen, and foyer. The entire house exterior was painted in August 2025, and a new second-floor deck was also completed in August 2025. The pristine condition of the lovely home, combined with the quiet, private setting on double lot at the end of a cul-de-sac, makes it the perfect Florida retreat for you and your loved ones. Situated in the enclave of Bishopscourt, a maintenance-free neighborhood behind the gates of The Oaks Preserve, lawn and landscape maintenance, as well as irrigation, are included in the homeowner’s association fees. You will delight in this graceful, inviting home. Membership in The Oaks, Sarasota’s finest golf and country club, is required with homeownership. With two distinctly unique 18-hole championship golf courses, 12 HAR-TRU tennis courts (4 lighted), croquet and pickle ball courts, a state-of-the art fitness center, fine and casual dining options, and a wealth of social events, The Oaks is truly Sarasota’s premier golf and country club. There is currently no waiting list for either Golf or Sports/Social membership.

156 Bishopscourt Road, Osprey

$3,190,000

5 Beds ⋅ 6 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

A gracious columned front porch, classic dormers and a grand entry staircase introduce this distinctive residence in The Oaks. Set along the 13th hole, the home and separate guesthouse occupy more than half an acre framed by mature trees, with southern exposure, expansive greenspace to the east and no golf cart path bordering the property's side of the course. The setting feels remarkably private and spacious, with beautiful views from virtually every room. Timeless Southern character meets thoughtful updates, including a new tile roof, new hurricane-rated windows and skylights, freshly painted interiors and exterior, refinished wood floors, new upstairs flooring and updated lighting inside and out. Designer wallpaper and a new powder room vanity add fresh style, while the generous covered front porch offers an inviting place for morning coffee and relaxed gatherings. The kitchen features white cabinetry, quartz countertops, a waterfall-edge peninsula and a walk-in pantry. An oversized Viking six-burner gas range with a griddle, a Thermador refrigerator, a EuroCave wine cooler, a built-in Miele coffee maker and reverse osmosis system complement the space. Formal dining, a living room with a fireplace and a light-filled family room create inviting settings for entertaining and everyday living. The main-level primary suite overlooks the pool and grounds, spacious custom-organized closet, dual vanities, soaking tub and separate shower. A study and an exceptionally large laundry room with abundant storage complete the first floor. Upstairs, three bedrooms each feature an en suite bath and walk-in closet. A hidden playroom with skylights offers a magical retreat for imagination and creativity, with its area additional to the stated living square footage. With a full kitchen and bath, the separate guesthouse provides flexible accommodations for visitors, extended family or an au pair. Together, the main home and guesthouse frame an inviting outdoor retreat with an open-air pool and spa, palms and expansive golf course views. Generous entertaining areas, a fenced yard and a screened patio with a fireplace offer spaces to gather or unwind throughout the seasons. The home also includes a recently installed whole-house Generac generator with a 200-gallon buried propane tank. The Oaks lifestyle includes golf, tennis, pickleball, fitness and multiple dining venues, complemented by social gatherings and holiday traditions. Enjoy a casual meal at the Overlook or an evening celebration at the club, with the Legacy Trail, Pine View School and the beaches of Siesta Key and Casey Key nearby. Located in Flood Zone X with no reported history of flooding, this residence brings together architectural charm, substantial recent improvements and an exceptional golf course setting.

871 Macewen Drive, Osprey

$600,000

4 Beds ⋅ 3 Baths ⋅ Blackburn Point Woods SubDv. ⋅ 34229 Zip Code

It’s always about the experience of living near Casey Key and the Intracoastal Waterway from this two-story town home in the maintenance-free community of Blackburn Point Woods. Nearby marina, waterfront park with boat ramp and trail for those seeking a lifestyle that celebrates the water, the wildlife, and the open spaces of Florida — nothing compares. A charming entry to the home leads to the inviting great room with soaring ceilings and a wood-burning fireplace. The first level features a private two-car garage and paver drive, French doors leading to a lanai and private pool area, and a secondary patio with an above-ground hot tub. With two bedrooms on the first level, one a generously sized primary with an en-suite bath, and two on the second, there is abundant space for everyone. Upper-level area for a den and a space for home fitness and an oversized closet. The chef's kitchen has solid wood cabinetry; topped in granite, there is kitchen dining as well as adjacent spacious formal dining. Thoughtful dry bar area for entertaining. Each floor/area of the residence has balconies for seamless indoor/outdoor living, the second-level 8-by-18 balcony has had wood replaced in 2026. Luxury Vinyl flooring throughout the living areas provides warmth and sophistication. Nearby are Publix, CVS, ice cream and coffee shops and numerous restaurants. This location is a short distance to Bayfront Park, tiki bar and two waterfront restaurants, a short scenic drive down Casey Key takes you to Nokomis Beach. The community amenities offer two heated pools, pickleball and tennis, a clubhouse and gym. This extraordinary home is the ideal frame for exceptional, easy living. Home is being offered turnkey furnished, excluding personal effects, some homeowner's decor, and staging decor.

455 Oak Point Road, Osprey

$1,575,000

5 Beds ⋅ 5 Baths ⋅ Talon Preserve On Palmer Ranch SubDv. ⋅ 34275 Zip Code

Welcome to the remarkable 14726 Eagle Branch Drive located within the gated community of Talon Preserve with NO CDD FEE. This stunning home combines distinctive architecture, versatile living spaces, and exceptional outdoor entertaining. This exceptional Layton Grande two-story residence features 5 bedrooms, 4.5 bathrooms, and a three-car garage with a 4-foot extension, showcasing extensive builder upgrades and seller customizations. Approximately 12-foot first-floor ceilings and soaring 13-foot tray and coffered ceiling add architectural elegance to this floor-plan. Double entry doors open to a dramatic two-story foyer with a tray ceiling and expansive clear-glass transom windows. Designer fluted accent walls and custom wood ceiling details add distinctive character. The open-concept living and dining areas feature a custom built-in bookshelf and media center surrounding the television, complemented by an electric fireplace. The gourmet kitchen boasts a 48-inch built-in KitchenAid refrigerator, double stacked cabinetry with illuminated glass-front doors, wall oven and microwave, cooktop, and a large quartz island with additional cabinets and shelving. The quartz countertops extend up as the backsplash for an elegant and seamless finish. The pantry features custom shelving and is set up to accommodate a secondary refrigerator. Pocket doors enclose a private guest wing with two bedrooms flanking a full bathroom. A third guest bedroom near the garage has an adjacent full bathroom with a walk-in shower. All bathrooms feature under-cabinet lighting and illuminated mirrors, while guest bedroom closets provide additional shelving and lighting. The spacious primary suite overlooks the pool and lanai through expansive windows. The primary bathroom features under-cabinet lighting, and the walk-in closet includes custom built-in shelving. The dedicated laundry room includes a utility sink, countertops with space for folding, shelving, and cabinetry. Upstairs, an open overlook captures views of the foyer and expansive windows. Under-stair storage accommodates household essentials. The large bonus room offers flexibility for an office, game room, or additional living space. An additional bedroom and full bathroom provide privacy for guests, while extra storage near the upstairs utility room adds convenience. Expansive impact glass, pocket sliding doors open to a private outdoor retreat featuring a custom saltwater pool with spill-over spa and additional water features, generous sun shelf, and custom outdoor kitchen. A pool bath enhances entertaining convenience. Pet owners will appreciate the side-yard dog run enclosed by a four-foot wrought-iron fence. Talon Preserve offers resort-style amenities, including a heated pool with rock waterfall and splash pad, spa, full-service restaurant and bar, approximately 18,000-square-foot clubhouse, state-of-the-art fitness center, arcade, eight pickleball courts, tennis and bocce courts, fire-pit area, and dog park with NO CDD FEE. Conveniently located near Oscar Scherer State Park, Nokomis and Siesta Key beaches, Legacy Trail, Sarasota Memorial Hospital, championship golf courses, I-75, and downtown Sarasota, Venice, and Wellen Park. Community information and governing documents are available at www.talonpreservehoa. Buyers should verify all information with the HOA.

14726 Eagle Branch Drive, Nokomis

$672,900

4 Beds ⋅ 4 Baths ⋅ Magnolia Bay SubDv. ⋅ 34275 Zip Code

Under Construction. The two-story front porch welcomes you into the entryway. A secluded guest suite with full bathroom and large walk-in closet is off the main entrance. French doors lead into the home office that offers plenty of natural light. The kitchen features a large island with built-in seating and corner walk-in pantry. The dining area is embraced by a corner of windows and allows access to the backyard covered lanai. The family room boasts tall ceilings. The primary bedroom has three large windows and a tray ceiling. Double doors lead to the bathroom which has dual vanities, a garden tub, glass enclosed shower, and oversized walk-in closet. Upstairs you are greeted by the game room which is surrounded by windows on two sides. Two secondary bedrooms each with walk-in closets and a shared bathroom complete the second level. The home offers ample storage throughout. The laundry room is located off the three-car garage that opens into the drop zone area.

270 Holly Bank Avenue, Nokomis

$1,485,999

4 Beds ⋅ 3 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Welcome to 1474 Landview Ln, a charming single-family home located in the desirable Southbay Yacht & Racquet Club in Osprey, FL. This spacious property features and exceptional layout with a total finished area of 3,246 sq.ft. As you step inside, you'll be greeted by a warm and inviting atmosphere with plenty of natural light flowing through the home. Quality, attention to detail, and fine finishes surround you in every room. The interior features 3 bathrooms, providing convenience and privacy for all residents and guests. Premium upgrades throughout include a built-in coffee system, custom cabinetry, multiple living rooms- including a 6' fireplace! The gourmet kitchen flows into the hearth room and simultaneously opens to the pool counter. The lot size is an impressive 10,560 sq.ft. offering ample outdoor space for entertaining, gardening, or simply relaxing in serene privacy. Whether you're looking to host a BBQ with friends or enjoy a quiet evening under the stars, this property has plenty of room to accommodate your lifestyle. Southbay Yacht & Racquet Club has it's own PRIVATE MARINA with well maintained boat slips up to 55ft. Easy access to the ICW and Gulf passes make Southbay one of Florida's most unique neighborhoods. Southbay is conveniently located near a variety of amenities and attractions, including the Heritage Bicycle and Recreational Trail. Finally, shopping, dining, a micro brewery, coffee shop, Pilates studio, fitness center, beauty salon and more are accessible with your golf cart via a designated entrance to the adjacent shopping center. Don't miss your chance to make this wonderful property your new home. With its ideal location, ample space, and charming features, boat slip, racquet courts, and more, 1474 Landview Ln is the perfect place to create lasting memories and enjoy the Florida lifestyle to the fullest. Contact us today to schedule a showing and see all that this property has to offer.

1474 Landview Lane, Osprey

$2,150,000

4 Beds ⋅ 5 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Beautifully updated and carefully maintained, this Rutenberg-designed home is idyllically situated on a half-acre corner lot surrounded by beautiful landscaping with views of the lake and the 14th Fairway of the Heron Course. This 4 bedroom residence has 4 full baths, 1 half bath, a formal living room with pool views, a separate formal dining room, and an open gourmet kitchen with gas cooktop, stainless appliances, two wallovens, a breakfast bar, an adjoining dining area and two pantries. The kitchen opens to an expansive family room overlooking the pool. The spacious master suite features a large luxury bath, two large his-and-hers closets and a lovely sitting area overlooking the pool. All three additional bedrooms are en suite. A dedicated office with built ins and a versatile bonus room/game room adds valuable flexibility for a wide variety of lifestyles. The large and lovely lanai includes an outdoor grill and bar, covered seating, awnings, and a freeform pool and spa overlooking the water and golf course. With a four-car garage, abundant storage and numerous updates, including a new roof installed in December 2024 (with warranty), a new pool heater installed in 2024, new central air conditioning (2 units, 2 zones) in 2022, freshly painted interior and exterior, this home is the perfect choice for those who want to live in comfort and luxury. A complete list of updates is available. The mandatory Membership to The Oaks Club will provide everything for living a country club lifestyle; two championship golf courses, tennis and pickleball courts, a regulation croquet lawn, state-of-the-art wellness center and a wide array of dining and social options. There is currently no waiting list for either Golf or Sports/Social membership.

642 Trenton Way, Osprey

$4,485,000

4 Beds ⋅ 6 Baths ⋅ Nokomis SubDv. ⋅ 34275 Zip Code

RARE BLACKBURN BAY WATERFRONT ESTATE | 119' DEEP-WATER FRONTAGE | PRIVATE DOCK | NO-BRIDGE GULF ACCESS Privately gated and beautifully positioned along Blackburn Bay, 2115 Lychee Lane is a rare waterfront estate offering privacy, refined living and an exceptional boating lifestyle. Set on approximately 0.58 acres with 119 feet of deep-water frontage, this three-home enclave has no monthly HOA and offers easy, no-bridge access toward the Gulf. With over 6,000 square feet of living space, the residence features expansive bay views, custom architectural details, crown molding, tray ceilings, 5-inch baseboards and 24x24 porcelain tile. The dramatic 2024 chef’s kitchen showcases custom floor-to-ceiling cabinetry, granite surfaces and Wolf, Sub-Zero and Cove appliances, opening to the dining room with fireplace and sweeping water views. The expansive family room with custom oak bar flows seamlessly to the waterfront entertaining areas. The first-floor primary suite offers panoramic water views, private terrace, generous bath and custom walk-in closet, complemented by a formal sitting area and office. A second primary suite upstairs features a private balcony, marble en-suite bath and two custom walk-in closets, with additional en-suite bedrooms for family and guests. Outdoor living is exceptional with a heated pool, spa, waterfall, outdoor kitchen, fireplace and expansive covered and open-air living areas overlooking Blackburn Bay. A private beach and firepit create an idyllic waterfront retreat. Boaters will appreciate the newly constructed deep-water dock with composite decking, 14,000-lb. boat lift, two jet-ski lifts, electricity and water, plus no-bridge Gulf access. Additional enhancements include impact-rated windows and doors, electric shutters, whole-home Generac generator, security and camera systems, automated blinds, programmable HVAC, commercial whole-house water filtration, irrigation well and a newly constructed elevated three-car garage with air conditioning. At 2115 Lychee Lane, Blackburn Bay is more than a backdrop—it is the lifestyle.

2115 Lychee Lane, Nokomis

$2,150,000

4 Beds ⋅ 4 Baths ⋅ Roberts Sub SubDv. ⋅ 34275 Zip Code

Striking from the moment you arrive, this 2022-built contemporary residence combines the scale and quality of a custom coastal retreat with a design created for the way Florida is meant to be lived. Set at 327 Roberts Road in Nokomis, the 4-bedroom, 3.5-bath home offers approximately 3,300 square feet under air and nearly 6,000 square feet in total, offering multiple levels of living, expansive balconies, oversized garages, a resort-style backyard, and no HOA. Built by OMKAL Construction and occupied since completion by its builder/owner, the property reflects a thoughtful approach to both design and construction. The three-story layout creates a natural separation between entertaining, everyday living, and private retreat. Elevated above the ground level, the main living floor is bright and open, with abundant natural light, added privacy, and a dramatic two-story great room framed by oversized picture windows and a custom linear fireplace. The kitchen opens seamlessly to the living and dining areas, pairing sleek modern cabinetry with an oversized center island designed for gathering. Expansive balconies extend the living spaces outdoors, capturing coastal breezes, elevated surroundings, and changing evening skies. The primary suite and two additional bedrooms are located on the main level, while the upper floor offers a private fourth suite and spacious loft, ideal as an office, lounge, library, or additional living area. From here, elevated balconies capture views toward the Intracoastal Waterway and offer a quiet vantage point for sunset. The arrangement provides exceptional flexibility for everyday living, extended family, and overnight guests. The finished lower level opens directly to the pool and backyard, creating a relaxed extension of the home's entertaining spaces. With room for a media lounge, fitness area, game room, or casual gathering space, it connects effortlessly to one of the property's most memorable features: its private outdoor retreat. A large heated saltwater pool with spa and tanning ledge anchors the backyard, surrounded by tropical landscaping, custom fencing, accent lighting, tiki torches, porcelain feature walls, and a fire pit. A covered pergola and grilling area provide another inviting place to gather, while generous deck space allows for dining, lounging, and entertaining. Private and beautifully composed, the entire setting functions as a true outdoor living environment rather than simply a backyard. The quality extends well beyond what is immediately visible. Built to newer Florida Building Code standards, the home features hurricane-impact windows and doors, an elevated stem-wall foundation, energy-efficient construction, a flat tile roof, synthetic stucco, large-format porcelain surfaces, and Level 5 smooth drywall, details chosen with Florida's climate, longevity, and ease of ownership in mind. And despite the sense of privacy at home, the best of the Gulf Coast remains remarkably close. Venice, Sarasota, Casey Key beaches, the North Jetty, boating, dining, and recreation are all within easy reach. Modern, substantial, and refreshingly individual, 327 Roberts Road offers something increasingly difficult to find near the coast: newer construction, exceptional indoor and outdoor space, no HOA, and the freedom to enjoy it all on your own terms.

327 Roberts Road, Nokomis

$12,650,000

4 Beds ⋅ 4 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code

Spanning nearly an acre from the Gulf of Mexico to Blackburn Bay, this one-of-a-kind Casey Key residence pairs 140 feet of private Gulf frontage with 130 feet of protected bayfront, offering private beach access, boating and sweeping water views from sunrise to sunset. Designed by Jerry Sparkman, AIA, NCARB, of Sweet Sparkman Architecture and completed in 2021, the residence blends architecture and nature, land and water, and linear and curved forms. Its elevated "split-level hugger" design combines a split-level floor plan with a modified courtyard concept, creating intimate gathering spaces and a seamless indoor-outdoor connection. Flowing rooflines, curved walls and broad overhangs form a sculptural silhouette, while warm wood ceilings and walls of glass fill the interiors with natural light and frame the Gulf, Blackburn Bay and tropical landscape in nearly every direction. The light-filled interior is centered around an open great room, dining room and kitchen, where soaring wood ceilings, oversized windows and expansive glass doors open to an elevated waterfront terrace. A separate lounge with a bar offers an inviting space for entertaining, while a waterfront fitness space opens directly to the lawn and bay. Upstairs, the primary suite is wrapped in floor-to-ceiling glass and features a private terrace with uninterrupted Blackburn Bay views. Its spa-inspired bath includes a floating dual vanity, freestanding soaking tub, glass-enclosed shower and corner windows overlooking the water. Three additional bedrooms accommodate family and guests, while the loft provides flexible living space. An elevator connects the home's levels for added convenience. Designed for coastal living, the residence unfolds around a private oasis with a resort-style pool, expansive terraces and shaded lounge areas. Curved stairways and elevated walkways wrap through the architecture, offering changing perspectives of the pool, lawn, bay and Gulf. Covered entertaining spaces provide comfortable places to gather out of the sun, while the open lawn extends toward the bayfront and private dock. From morning on the water to sunset over the Gulf, the property offers a seamless waterfront lifestyle. The residence has also earned NGBS Emerald certification, the highest tier under the National Green Building Standard, along with a RESNET HERS Index rating of -28, a score below zero means the home produces more energy than it consumes, powered in part by on-site solar. It's a rare combination of coastal luxury and true net-positive energy performance. The Gulf-to-Bay setting is essential to the experience. The private dock and boat lift provide direct access to Blackburn Bay, the Intracoastal Waterway and the Gulf. On the west, sunset views are just steps from the beach. A refined palette of stucco, glass, wood and concrete balances architectural sophistication with coastal durability. Native beach grasses, sea grapes and palms soften the transition between the home and its island landscape. Elevated to meet FEMA floodplain requirements and coastal-resiliency standards, the residence responds thoughtfully to its barrier-island setting. Located on Casey Key, it offers exceptional seclusion without sacrificing convenience. The property is positioned between Sarasota and Venice, near historic downtown Venice, Nokomis Beach and waterfront dining, with convenient access to Sarasota International Airport and downtown Sarasota.

1716 Casey Key Road, Nokomis

$6,850,000

4 Beds ⋅ 4 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code

Virtually Staged. Imagine the possibilities of Gulf-to-Bay living on Casey Key, where deeded private beach access, deep-water boating and a resort-style bayfront setting create the foundation for an extraordinary coastal retreat. Set on more than half an acre with frontage on Blackburn Bay, 2116 Casey Key Road offers more than 5,500 square feet and an exceptional opportunity to enjoy a substantial island residence within one of Sarasota County’s most coveted waterfront settings. The exterior has been thoughtfully enhanced for enjoying life on the water. Along the bayfront, a multi-level tropical setting unfolds through expansive pavered terraces, covered lounge areas and a gazebo-style dining pavilion with a fully equipped summer kitchen and built-in grilling station. At the center is a heated swimming pool and spa finished in PebbleTec, creating a private resort environment framed by mature tropical surroundings and the waters of Blackburn Bay. A screened second-level bayfront terrace provides another inviting place to relax. For boaters, the property is equally compelling. The extended dock, updated in 2018, includes a lift and provides deep-water access, accommodating both powerboats and sailboats. Deeded private beach access places the Gulf’s turquoise waters and spectacular sunsets just steps from home, creating the increasingly rare opportunity to enjoy both boating and the beach from a single property. Inside, the residence reveals an impressive sense of space and a distinctive architectural character. Soaring cathedral ceilings, generous room proportions and walls of oversized impact windows and sliders fill the home with natural light while capturing sweeping views across Blackburn Bay. The substantial footprint and flexible two-level configuration provide an exceptional foundation for comfortable waterfront living, with the opportunity to embrace the home's individual character or introduce a more contemporary coastal aesthetic. The first level offers inviting spaces, including a family room, game room, two guest bedroom suites, an office with built-ins that can also function as a fourth bedroom, and a convenient kitchenette. This arrangement lends itself beautifully to extended family, visiting guests or the creation of private living quarters within the home. Upstairs, the main living spaces take full advantage of the elevated bayfront setting. The living and dining rooms are joined by a kitchen with granite countertops, center island, informal dining area and stainless steel appliances, along with a wet bar and wine cooler. The primary suite is also located on this level, allowing the principal living spaces to share the home’s expansive water views. A three-stop elevator and interior staircase connect the levels. Considerable improvements include a 2022 metal roof, multiple A/C replacements from 2017–2024, replacement of non-impact windows with Andersen impact windows, updated dock and lift pilings, new ductwork, electrical upgrades and re-piping. Located on the quieter southern end of Casey Key, the property feels wonderfully removed while remaining convenient to Nokomis, Venice and Sarasota. Nearby destinations include Nokomis Beach, the restaurants and boutiques of Venice Island, area marinas and the Legacy Trail, while Downtown Sarasota’s dining, performing arts, cultural attractions and waterfront are within comfortable reach.

2116 Casey Key Road, Nokomis

$1,024,999

5 Beds ⋅ 5 Baths ⋅ Cassata Lakes SubDv. ⋅ 34275 Zip Code

Under Construction. ****SPECIAL FINANCING AVAILABLE FOR A LIMITED TIME ONLY FROM PREFERRED LENDER. RESTRICTIONS APPLY, FOR QUALIFIED BUYERS, SUBJECT TO APPLICABLE TERMS AND CONDITIONS. SUBJECT TO CHANGE WITHOUT NOTICE**** Welcome to The Madison—a spacious, elegantly designed two story home that blends luxury, comfort, and modern functionality. With 5 bedrooms and 5 bathrooms, this thoughtfully crafted residence offers ample room for both relaxation and entertaining. The first floor boasts a den, off the entry; a gourmet kitchen, with well appointed finishes, premium cabinetry, and an expansive island ideal for gathering; and a lanai, off the great room, via a large sliding glass door, creating an inviting indoor–outdoor living experience perfect for Florida evenings. A second owner's suite and additional pool bath finish off the first floor. Upstairs, the owner’s suite serves as a private retreat with generous space and refined details. The second story also includes three additional bedrooms, two full bathrooms, and a versatile bonus room—ideal for a media lounge, playroom, or home office. Every corner of The Madison showcases thoughtful design and elevated style, making it a standout choice for those seeking a home that feels both elevated and welcoming.

1563 Lugano Circle, Nokomis

$1,445,000

3 Beds ⋅ 4 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Discover incredible value and endless potential in this beautifully maintained 3 bedroom, 3.5 bath home, tucked into lush tropical landscaping, on a quiet cul-de-sac in The Oaks Bayside. A grand traditional residence, with generous sized rooms, flexible living areas, and a private outdoor setting, the possibilities here are limitless. Step into the marble entry through the double front doors, and you will love what you find inside. Just off the entry, a cozy den with fireplace sits opposite a spacious guest suite. The heart of the home is the light-filled great room, with formal living and dining areas opening through French doors to the covered patio and resort-style pool. The kitchen combines beauty and function with granite countertops, center island cooktop, breakfast bar, and a sunny nook overlooking the pool. The elegant primary suite offers marble floors, soaring ceilings, plantation shutters, and private access to the pool for an early swim or late-night dip. A glamorous dressing area leads to the spa-like bath with soaking tub, walk-in shower, and marble finishes. Two additional oversized en suite bedrooms provide comfort and privacy for guests. A large laundry room with ample cabinetry and an adjacent private sauna completes the interior. Outdoors, the free-form pool with rock outcroppings and waterfall is a showstopper, surrounded by both shaded and open areas for dining and relaxing. With two adjoining lots preserved as gardens, this home offers rare seclusion in a natural setting. The Oaks Club features two 18-hole championship golf courses, an award-winning tennis program, pickleball courts, a state-of-the-art fitness center and a junior Olympic, community pool as well as a celebrated social calendar, and incredible dining options. There is currently no waiting list for either Golf or Sports/Social membership.

422 Blue Garden Lane, Osprey

$1,900,000

3 Beds ⋅ 4 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Experience an extraordinary waterfront lifestyle in this distinctive 3-bedroom, 3.5-bath Mizner-inspired residence, ideally positioned along Little Sarasota Bay in the prestigious Oaks Bayside. Tucked away on an intimate cul-de-sac shared by just 3 homes, this exceptional property with close to 4,000 SF of living space, offers remarkable privacy, an enchanting Old Florida setting surrounded by mature oaks and lush tropical foliage, and captivating views and sunsets stretching across Little Sarasota Bay. Thoughtfully custom designed to embrace its spectacular surroundings, the home is filled with natural light and showcases beautiful architectural details throughout, including porcelain tile flooring, soaring 14-foot and tray ceilings, extensive custom millwork and built-ins, and walls of impact-rated windows and French doors framing the surrounding landscape and water views. Fresh interior paint and brand-new porcelain tile floors and carpeting in 2026 bring a crisp, refreshed feel to the residence while preserving its distinctive character. At the heart of the home, the kitchen features stone countertops, a Sub-Zero refrigerator, ASKO dishwasher, stainless steel appliances and generous workspace, opening comfortably to the home's main gathering areas. French doors create a seamless connection to the elevated pool and spa terrace, an inviting private retreat for entertaining, relaxing in the Florida sunshine or enjoying the bay breezes and spectacular evening skies. The expansive primary suite enjoys an entire level of its own, creating a true private retreat complete with a separate sitting room/office, custom built-ins, generous closet, dedicated laundry and an ensuite bath. The upper level provides exceptional privacy for family and guests with 2 additional bedrooms, a full bath, and flexible office/media space. The convenient 3+ car oversized garage with ample storage is on the ground floor. A brand new five-stop elevator will be installed to provide convenient access throughout the home, extending to the rooftop terrace where panoramic water views and unforgettable Florida sunsets take center stage. Enjoy ultimate peace of mind with a gas generator included on-site. Beyond the residence, ownership in The Oaks provides access to one of Sarasota's most established private country club lifestyles, with championship golf, racquet sports, state-of-the-art fitness, dining and an active social calendar. Community dock located on Little Sarasota Bay. Private, distinctive and surrounded by natural beauty, 168 Coastal Hammock Court presents a rare opportunity to enjoy gracious bayfront living in one of Sarasota's most coveted gated communities.

168 Coastal Hammock Court, Osprey

$5,750,000

4 Beds ⋅ 8 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code

At the water’s edge of Sandspur Lane sits one of Casey Key’s best-kept secrets: a stunning estate offering unmatched privacy, tranquility, protected waterfront, and bespoke contemporary coastal architecture. A multi-year renovation completed in 2024 reimagined the property, adding more than 2,000 square feet of interior and exterior living space and transforming an already exceptional waterfront home into a truly distinctive residence. Tucked at the end of this quiet, private lane, the home’s structural features and sheltered location provide proven storm-resilient advantages. Ownership of both sides of the canal protects the mature trees and vegetation along the opposite shoreline, preserving natural privacy. The main level features vaulted ceilings and an open floor plan connecting the modern kitchen with dining, living, and family rooms, while wraparound aquarium glass windows and sliding glass doors flood the space with natural light and offer views of the water and the parcel’s expansive waterfront setting. A floating staircase rises through a circular glass stair tower to the primary suite, featuring a spacious bath, sitting room, and a private balcony with long water views. An adjoining casita with its own private entrance and water views provides luxurious accommodations for family, guests, or in-home staff. Two dedicated offices with built-in cabinetry and granite desks offer long ICW views, creating an inspiring setting for work or personal pursuits. A new elevator connects every level, from the garage to the rooftop deck. Designed for recreation and entertaining, the property features a cabana with bar and outdoor kitchen, a new waterfall spa and remodeled pool with water features, a home gym, firepit, indoor-outdoor Sonos sound system, and multiple balconies, terraces, and decks. After sunset the extensive outdoor lighting, including dock and underwater fish lights, transforms the property. The long driveway and motor court accommodate parking for 12–15 vehicles— a rarity on Casey Key. The 200 feet of protected waterfront includes a newly added 45-foot dock, 20,000-lb. boat lift, and two PWC lifts. And when the Gulf beckons, deeded beach access leads to its warm waters and shoreline. From sunrises over the ICW to Gulf sunsets from the rooftop deck and illuminated evenings poolside, the home embraces its waterfront setting from virtually every angle. This residence offers a package increasingly hard to find: extraordinary privacy, tranquility, and protected waterfront living—all wrapped in a beautifully reimagined contemporary coastal estate on one of Florida’s most exclusive islands.

3718 Sandspur Lane, Nokomis

$4,590,000

5 Beds ⋅ 5 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Experience exceptional waterfront living in Southbay Yacht & Racquet Club at this expansive custom John Cannon residence offering more than 5,200 square feet, 5 bedrooms, 5 baths and sweeping panoramic water views from both levels. Set along more than 135 feet of waterfront, the home was thoughtfully designed to embrace its remarkable setting, with soaring ceilings, generous expanses of glass and beautifully proportioned indoor and outdoor living spaces overlooking the bay and Intracoastal Waterway. A completely reimagined front drive and all-new landscaping create a striking first impression and a fresh, refined coastal presence. Beyond the grand double-door entry, the home immediately opens to dramatic water views, drawing the eye through the interior and out toward the horizon. Ceilings rising to approximately 21 feet enhance the sense of scale, while a series of inviting living and entertaining spaces allow the home to feel equally suited for intimate evenings or larger gatherings. The kitchen serves as the heart of the residence, anchored by a substantial granite island and complemented by a gas cooktop with pot filler, while views stretch beyond the pool to the water. A full bar and dedicated wine room enhance the main level, with an additional wet bar upstairs for effortless entertaining throughout the home. Privately positioned on the main level, the primary suite is a serene waterfront retreat with a sitting area, two generous closets and an expansive bath. Additional downstairs bedrooms are thoughtfully located on the opposite side of the residence, creating privacy and separation for family and guests. Upstairs, either an office or a fifth bedroom offers an elevated and inspiring setting for work or quiet retreat, with access to the upper terrace and its sweeping water views. From both floors, the landscape of water and sky becomes part of the experience of the home. Outdoor living is equally memorable. A heated pool and spa, covered and screened entertaining areas, outdoor kitchen, fireplace, expansive terraces and private dock create a seamless connection between the residence and the waterfront. Mornings begin with peaceful views across the water, afternoons unfold poolside, and evenings are defined by the colors of sunset. Southbay Yacht & Racquet Club offers one of the area's most distinctive boating lifestyles. Its community-owned deep-water marina accommodates vessels up to 55 feet, allowing residents to walk or take a golf cart from home to their boat. Community amenities include a renovated clubhouse, geothermal pool, fitness center overlooking the marina, tennis and pickleball courts, bocce, shuffleboard, basketball, kayak storage, a waterfront park, approximately 20 acres of common grounds and miles of walking trails. Perfectly positioned between Sarasota and Venice and convenient to Siesta Key, Nokomis Beach, the Legacy Trail, Pine View School, waterfront dining, shopping and Oscar Scherer State Park, 275 Lookout Point is a compelling blend of scale, setting and lifestyle—a substantial waterfront residence with panoramic views, private outdoor living and direct access to the heart of Southbay’s boating community.

275 Lookout Point Drive, Osprey

$1,430,000

3 Beds ⋅ 4 Baths ⋅ Duke Sub SubDv. ⋅ 34275 Zip Code

Virtually Staged. WELCOME TO YOUR PRIVATE NOKOMIS RETREAT! Set on a fully fenced and gated one-acre homesite surrounded by mature trees, this custom-built 2016 residence combines quality craftsmanship, impressive living spaces, and exceptional indoor-outdoor Florida living. Beautiful curb appeal begins with a gated entrance, expansive paved driveway with abundant parking, attached three-car garage, lush tropical landscaping, and distinctive architectural details. A metal roof, board-and-batten accents, stonework, custom railings, and a spacious covered front entry framed by substantial columns complete the exterior, while impact windows and doors provide added protection and peace of mind. Step through the foyer into a beautifully designed interior featuring bamboo flooring, vaulted ceilings with exposed beams, crown molding, plantation shutters, and custom handcrafted barn doors. The expansive living room is anchored by a floor-to-ceiling electric fireplace and opens naturally to the dining room, kitchen, and lanai for an easy flow throughout the main living areas. The spacious kitchen is designed for both everyday living and entertaining with granite countertops, coordinating backsplash, stainless steel GE Café appliances, an apron-front farmhouse sink, upgraded fixtures, generous cabinetry, and a large pantry. Its open design keeps the kitchen connected to the surrounding living and dining spaces. Pocketing sliding glass doors open to the expansive screened lanai and heated saltwater pool, seamlessly extending the living space outdoors. Multiple covered patio areas with tongue-and-groove ceilings provide plenty of room for dining, entertaining, and relaxing while overlooking the beautiful backyard. Beyond the pool, a broad manicured lawn shaded by mature trees creates an inviting setting with plenty of usable outdoor space. Gather around the fire pit, enjoy the open lawn, or take advantage of the multiple detached storage buildings for lawn equipment, tools, recreational gear, and additional storage. Privately positioned on one side of the home, the primary suite features a vaulted ceiling, spacious walk-in closet with custom wood shelving, and an ensuite bath with dual granite-topped vanities and an impressive steam shower finished in floor-to-ceiling marble tile. Two generously sized guest bedrooms are located on the opposite side of the home and are complemented by two additional full bathrooms. A dedicated office near the foyer provides a comfortable work-from-home space, while the oversized separate family/entertainment room offers flexibility for a media room, game room, hobby area, or additional gathering space. A dedicated mudroom provides a convenient transition from the garage, while the spacious laundry room offers abundant cabinetry, quartz countertops, a utility sink, and excellent additional storage. Offering approximately one acre, a three-car garage, heated saltwater pool, extensive covered and screened outdoor living space, a large fenced backyard, multiple storage buildings, and a versatile floor plan, this distinctive Nokomis home delivers space and functionality in a peaceful setting. All of this is within easy reach of shopping, dining, recreation, and the beautiful Gulf Coast beaches.

1501 Sweetland Street, Nokomis

$1,374,313

3 Beds ⋅ 4 Baths ⋅ Talon Preserve On Palmer Ranch SubDv. ⋅ 34275 Zip Code

Beautiful Layton on a premium lake and preserve homesite. SDO

6217 Grande Talon Lane, Nokomis

$979,999

4 Beds ⋅ 4 Baths ⋅ Cassata Lakes SubDv. ⋅ 34275 Zip Code

Under Construction. ****SPECIAL FINANCING AVAILABLE FOR A LIMITED TIME ONLY FROM PREFERRED LENDER. RESTRICTIONS APPLY, FOR QUALIFIED BUYERS, SUBJECT TO APPLICABLE TERMS AND CONDITIONS. SUBJECT TO CHANGE WITHOUT NOTICE**** Welcome home to the Juniper. A sprawling 2-story dream, the Juniper features an open-concept floorplan with 4 bedrooms, 3.5 bathrooms, a den, loft, and a 3-car garage. Head through the covered entry into the first floor of this grand home. A den and powder room sit on one side, and a laundry room is on the other. A spacious open floorplan gives you the best of both worlds with a formal and informal dining space that looks directly into the great room. Just waiting for a cozy couch for lazy Saturday mornings or Monday night football, you’ll love how the great room looks out to the covered lanai. The kitchen is truly a chef’s dream with a large center island containing a double basin sink for plenty of food preparation space. The owner’s suite sits on the main floor, sharing no walls with other bedrooms for maximum privacy and relaxation. Enjoy a tranquil owner’s bath with a large, connected walk-in closet for all your belongings, and unwind from the day with a large, enclosed shower and tub. Step directly outside the mud room into the large 3-car garage to make school mornings even easier. After your grand tour of the main floor, head to the second story, which features a loft open to the floor below, creating high ceilings and a grand appearance. Three bedrooms wait upstairs, each with a walk-in closet of its own, and 1 bedroom houses its own bathroom.

1575 Lugano Circle, Nokomis

$3,700,000

4 Beds ⋅ 4 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

This custom-built 2024 masterpiece was thoughtfully designed to deliver the perfect balance of luxury, functionality, and effortless indoor-outdoor living. Positioned to capture sweeping views of the 6th and 7th holes of the Heron Course, the home showcases exceptional craftsmanship and attention to detail at every turn. From the moment you arrive, the impressive 10 foot hurricane-rated steel front door, circular driveway, and beautiful exterior create a lasting first impression. Inside, wood-look tile flooring flows throughout. The expansive open concept layout seamlessly connects the main living spaces while still offering dedicated rooms for privacy and everyday comfort. The designer kitchen is a true showpiece, featuring a custom range hood, pot filler, oversized refrigerator, and premium finishes that cater to both casual family meals and formal entertaining. The large master suite is a study in elegance. The luxurious master bath is the pinnacle of luxury, with dual sinks, a lighted stand alone make up table, claw foot tub, huge steam shower, expansive countertop and storage space along with custom lighting. The upstairs loft is a great addition for those who love to entertain and host guests. It has a bedroom, bathroom, and living area with a bar and a balcony providing lovely views over the pool. Step outside to a truly exceptional outdoor retreat where luxury and tranquility come together in a breathtaking setting. The resort-style pool and spa serve as the centerpiece of the home's outdoor living experience. Designed for both relaxation and entertaining, this private oasis features expansive lounging areas, an incredible outdoor kitchen, and seamless indoor-outdoor connectivity through hurricane-rated bifold sliders that open the home to the stunning golf course backdrop. Built not only for beauty, but also for convenience and peace of mind, the home is equipped with premium hurricane-rated windows and bifold sliders, spray foam insulation, central vacuum, automated lighting and climate control systems, and wiring for a generator. Everyday functionality is enhanced by a dedicated mudroom, spacious laundry room, climate-controlled storage, and a four-car garage complete with epoxy floors, custom storage solutions, and additional space for a gym or workout area. shaded dining, and a sun-splashed pool and spa area under a screened enclosure. With mandatory membership, this home offers access to all of the amenities being a member of The Oaks has to offer. There is currently no waiting list for either Golf or Sports/Social membership.

650 Oaks Creek Court, Osprey

$629,400

3 Beds ⋅ 3 Baths ⋅ Meridian At The Oaks Preserve SubDv. ⋅ 34229 Zip Code

Virtually Staged. EXCEPTIONALLY SPACIOUS CORNER CONDO – NEARLY 3,200 SF – NO WAITLIST FOR GOLF MEMBERSHIP! Ideally situated behind the gates of the highly sought-after Oaks Preserve, this elegant and beautifully appointed corner residence offers an impressive combination of space, privacy, and resort-style living. The nearly 3,200 SF open floorplan features 3 en-suite bedrooms and 3 baths, providing exceptional comfort and flexibility. Light and bright throughout, the residence showcases crown molding, engineered hardwood flooring, and an expansive kitchen with granite countertops and stainless-steel appliances. Enjoy the serene, private preserve setting from multiple screened balconies, enhanced by convenient remote-controlled automatic hurricane shutters. Additional features include 2 assigned parking spaces, including 1 under-building space, plus climate-controlled storage. A rare opportunity to enjoy substantial living space, privacy, and the exceptional lifestyle of The Oaks! This NEWEST Tower (built in 2007) in the Meridian Condo Complex features Hurricane Impact Windows and Doors and is conveniently located next door to the condo residents’ private Amenity Center featuring Heated Pool & Spa, Fitness Room and outdoor grill in addition to The Oaks Club’s main campus of amenities. THE OAKS is a distinguished country club community which boasts many accolades including: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World - where amenities include two, 18-hole championship GOLF courses, award-winning TENNIS program with 12 Har-Tru Hydro-Grid TENNIS courts, 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL. The Oaks is just minutes from nationally ranked Pine View School, the Legacy Bike Trail, area Beaches and all that Gulf Coast living has to offer. Membership is required and there is NO WAITLIST for GOLF or SOCIAL Membership. **A MUST SEE**

3603 N Point Road Unit 202, Osprey

$1,309,462

4 Beds ⋅ 4 Baths ⋅ Talon Preserve On Palmer Ranch SubDv. ⋅ 34275 Zip Code

Stellar Grande with Pool/Loft

14735 Eagle Branch Drive, Nokomis

$4,695,000

6 Beds ⋅ 5 Baths ⋅ Gedney Richard H Inc SubDv. ⋅ 34275 Zip Code

Experience effortless luxury in this exceptional Gulf-front estate on the pristine shores of Casey Key, where the Gulf is your backyard and privacy, tranquility, and sweeping water views await! Originally built in 1951 and tastefully renovated in 2016 and 2025, this beach-front residence seamlessly blends classic character with refined modern updates. Offering nearly 4,000 square feet of living space under air, this home features 6 bedrooms and 4.5 bathrooms across three levels, designed for both comfort and entertaining. Generous room for hosting/gathering throughout with three expansive balconies inviting you to enjoy both breathtaking Gulf and intracoastal waterway views! Thoughtfully designed in-law quarters on the first level with the second level featuring a gourmet chef’s kitchen, family room and additional guest rooms/baths. The chef's kitchen is equipped with a Wolf six-burner gas range with griddle and double oven, a Sub-Zero PRO refrigerator/freezer, granite countertops, soft-close cabinetry, and a large centerpiece island perfect for casual dining with a view. The Owner's level on the third floor is to die for! Tremendous views of the Gulf from the substantial primary suite with this level also featuring a sitting area and den/office/bonus room that has views of the intracoastal waterway! The primary bathroom includes a stand-alone garden tub with skylight over, large walk-in glass and tile shower, dual vanities, and solid wood cabinets with granite countertops. Additional highlights include impact windows and doors, travertine flooring throughout (with the exception of engineered hardwood in the kitchen), marble-tiled baths, and a 2-car garage. Recent improvements include a new metal roof (2025), fresh paint inside and out (2025), a new septic system (2025) and A/C system (2023), offering peace of mind for years to come. Offered turnkey furnished. With private beach access steps away, this is a rare opportunity to own a truly remarkable waterfront retreat on one of Florida’s most desirable barrier islands! Call today for more information or to set up a private tour! **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

412 S Casey Key Road, Nokomis

$642,184

4 Beds ⋅ 4 Baths ⋅ Tiburon SubDv. ⋅ 34275 Zip Code

Under Construction. What's Special: Close to Trails | South Facing Patio | 1st Floor Primary Suite. New Construction - December Completion! Welcome to the Bermuda at 7068 Foxboro Way in Tiburon! This spacious two-story home offers four bedrooms, three-and-a-half bathrooms, a versatile loft, and a flexible space. The open-concept layout seamlessly connects the kitchen, casual dining area, and great room, creating an inviting setting for everyday living and entertaining. The first-floor primary suite features a walk-in closet and well-appointed bathroom. Upstairs, enjoy a spacious loft, three secondary bedrooms, including one with a private en-suite, and a shared bathroom. Outdoor living is enhanced by a covered lanai, and carefully selected design features such as tray ceilings, 8-foot interior doors, and whole-house impact windows add both style and functionality throughout the home. Tucked away in a peaceful Sarasota County setting on 40 acres, Tiburon offers the warmth and intimacy of a boutique community - where neighbors know each other and life moves at a more relaxed pace. With just the right blend of privacy and connection, Tiburon is ideal for those seeking a quieter, more personal lifestyle. Additional Highlights Include: washer, dryer, counter depth GE side by side refrigerator, extended flooring to primary bedroom and closet, and personalized outdoor entertainment. Photos are for representative purposes only. MLS#A4707180

7068 Foxboro Way, Nokomis

$3,700,000

5 Beds ⋅ 5 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Welcome to extraordinary living! This completely private oasis is perfectly positioned along North Creek in The Oaks Bayside, one of the most sought-after communities in South Sarasota. Situated on a lot and a half, the view is peppered with lush foliage, creating total seclusion and the feel of a luxury retreat. One of the most desirable floor plans in the community, with open flow and complete separation from the master suite and guest accommodations, creates a comfortable and highly functional living space. The casita provides the perfect separate space for an office, a studio or long-term guest accommodations, with stunning views from the second floor. Fine finishes and quality craftsmanship are showcased throughout this home, custom built by renowned contractor Baron Construction. Features include French oak flooring, quartz countertops, premium appliances, central vac, wired Sono speakers throughout the house, ADT security and Ring camerias around the exterior, and numerous custom details. The combined living and dining area provides an ideal setting for entertaining, opening directly to the outdoor pool and spa. For more casual gatherings, the spacious kitchen and breakfast nook flow seamlessly into the family room and out to the covered outdoor living space. This screened area is beautifully designed with a pool and spa, and grill. The covered areas and ceiling fans provide comfort for al fresco dining. The lots’ site is spectacular, with great water views, and areas to launch your kayak or paddleboard. Add in the practical features like a newer roof, oversized three car garage and huge pantry and you have found a home of distinction with no peer. The Oaks Bayside is a gated bayfront community within The Oaks. The distinguished private club offers 2 championship golf courses, pickleball and tennis courts, a state-of-the-art WellFit Center, exquisite dining options and a celebrated social calendar. The location provides convenient access to downtown Sarasota, dining, nightlife, and the cultural amenities of the Gulf Coast. Club membership is required with home ownership. There is currently no waiting list for either Golf or Sports/Social membership.

324 Osprey Point Drive, Osprey

$949,999

4 Beds ⋅ 4 Baths ⋅ Cassata Lakes SubDv. ⋅ 34275 Zip Code

Under Construction. ****SPECIAL FINANCING AVAILABLE FOR A LIMITED TIME ONLY FROM PREFERRED LENDER. RESTRICTIONS APPLY, FOR QUALIFIED BUYERS, SUBJECT TO APPLICABLE TERMS AND CONDITIONS. SUBJECT TO CHANGE WITHOUT NOTICE**** The Crystal is an elegant, award-winning home. Starting at 3,116 square feet, its layout includes four bedrooms, three full bathrooms, an enormous open-concept kitchen and great room, second-floor bonus room, and a three-car garage. As you walk in the front door, you are greeted by a bedroom with a full bath and a den, perfect for guests who want their own space for privacy. Walk farther into the home and enter the large combination dining-great room area, which opens directly into the kitchen. The kitchen is equipped to meet the demand of your culinary adventures. The owner's suite sits on the far corner, giving you maximum peace and privacy with a spacious walk-in closet. An upscale owner's bath boasts an enclosed shower area, double sinks, and a separate water closet. The upstairs opens up to a large bonus room and also includes a bedroom and full bath. Finishing off this plan is a three-car garage.

2048 Varese Street, Nokomis

$2,800,000

4 Beds ⋅ 4 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Ideally positioned on a quiet interior cul-de-sac this beautifully updated 4 bedroom, 4 bath home is located behind the gates of The Oaks Bayside. The residence features 16 ft and vaulted ceilings, white oak and marble flooring, custom crown molding, plantation shutters and extensive built-ins. The chef’s kitchen boasts marble countertops, custom hardwood cabinetry, a galley workstation sink, and premium appliances. The spacious layout flows to the private screened lanai with pool and spa, outdoor kitchen, and multiple covered seating areas overlooking lush gardens and offering tranquil lake views. The Oaks Club’s unmatched amenities include two championship 18-holf golf courses, 12 tennis courts and 4 pickleball courts, the state-of-the-art WellFit Center, a junior Olympic pool, a celebrated social calendar, and a wide array of dining options and recreational activities. Club memebership is required. There is currently no waiting list for either Golf or Sports/Social membership ---

662 Fernwalk Lane, Osprey

$1,590,000

3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Under contract-accepting backup offers. Located behind the gates of The Oaks Clubside and within close proximity to the clubhouse, this 3-bedroom plus office, 3.5-bath residence offers over 3,500 square feet of refined, comfortable living. Positioned on the 4th hole of the Eagle Course, the home features expansive golf views enjoyed from the screened lanai with pool and spa. The interior includes an elegant formal living room with fireplace, formal dining room, a spacious master suite with an oversized walk-in closet, a large laundry room, tray ceilings, crown molding, ceiling fans. This home has a whole-house generator, hurricane protection. a NEW ROOF and NEW HVAC. An oversized 3-car garage and circular paver driveway complete the property, providing everything needed to enjoy refined country club lifestyle The Oaks offers. The club’s amenities include two championship golf courses, pickleball courts, 14 Har-Tru courts and a croquet court, exceptional culinary experiences and a robust social calendar. Required with homeownership, there is currently no waiting list for either Golf or Sports/Social membership.

402 Macewen Drive, Osprey

$1,700,000

3 Beds ⋅ 3 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Custom built by Emerald Homes, this beautifully updated 3 bedroom + bonus room, 3 bath residence, offers a bright, inviting layout with generous living spaces and thoughtful design throughout. Behind the gates of The Oaks Bayside, it is beautifully situated, set back on a lot that offers peace and privacy. The open kitchen is a home chef’s dream and serves as the centerpiece of the home. Showcasing custom cabinetry, expansive counter space, and high-end appliances, the layout is ideal for both everyday cooking and effortless entertaining. There is a breakfast bar, dinette that is flooded by filtered sunshine through the tinted aquarium window, as well as a formal dining room. The living spaces flow seamlessly, enhanced by abundant natural light and refined finishes that elevate the home’s incredible appeal. The master suite has extra insulation between the great room and the master bedroom wall, ensuring a quiet, private sanctuary. The room is spacious and features a spa-like master bath with a tub, large separate walk-in shower, dual sinks and an abundance of mirrors and lighting. Step outside to a lovely lanai, with pool, spa and outdoor kitchen. This space is perfectly designed for relaxing, hosting gatherings, or enjoying the tranquil Florida lifestyle year-round. This gorgeous home offers so much, you truly must see it to fully appreciate it! Residents of The Bayside enjoy a 24-hour guarded entrance and a private community pier perfect for kayaking, fishing, or taking in spectacular sunsets over Casey Key. Ownership also provides access to the exceptional lifestyle of The Oaks Club, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, the state-of-the-art WellFit Center, a Junior Olympic swimming pool, outstanding dining venues, and an active year-round social calendar. Club membership is required, and there is currently no waiting list for either Golf or Sports/Social membership.

141 Sugar Mill Drive, Osprey

$2,175,000

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Experience luxury living in this beautifully appointed traditional home featuring 4 bedrooms, 3.5 bathrooms, and a dedicated office. The formal living room offers a fireplace and French doors, allowing separation from the kitchen and family room for more intimate gatherings. The spacious master suite includes two walk-in closets with custom built-ins, a sitting area, and a spa-inspired bath with dual vanities, soaking tub, and separate shower. Guests enjoy privacy in an en suite bedroom with direct pool access, while two additional bedrooms share a conveniently located third bath. A three-car garage provides ample space for vehicles and hobbies, complete with a workspace, overhead storage, and cabinets. Ideally positioned as the closest residence to the clubhouse on MacEwen, the home overlooks the 2nd and 3rd holes of the Eagle Course. Manicured landscaping offers complete privacy. Beyond are breathtaking golf course and lake views. Outdoor living features an expansive pool deck, screened lanai, fully updated outdoor kitchen, and a charming open-air patio. The renovated kitchen opens to the family room and includes a breakfast nook with aquarium window offering pool views, plus a formal dining room and breakfast bar for flexible entertaining. This exceptional home combines privacy, comfort, and a prime location for the ultimate country club lifestyle. Membership in The Oaks Club is required. The Oaks Club, Sarasota’s premiere golf and country club, has two champion 18-hole golf courses, twelve HAR-TRU tennis courts (4 lighted), four pickleball courts, an over 7,500 square foot state-of-the-art WellFit Center, an award-winning culinary team, and robust activities and social calendars. Club membership is required with homeownership. There is currently no waiting list for either Golf or Sports/Social membership

362 Macewen Drive, Osprey

$1,349,999

4 Beds ⋅ 4 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Looking for a home with room for everyone? This expansive 3255 square foot Southbay residence delivers! Located in the highly desirable Southbay Yacht & Racquet Club and close to the renowned Pine View School, this spacious home is just 12 years young. Built with 10-foot ceilings, generously sized rooms, beautiful architectural details and hurricane-rated windows and doors, it offers both style and peace of mind. Step inside the foyer to a welcoming dining room with an architectural wall opening to the living room featuring a shiplap accent wall and sliding glass doors leading to the covered lanai and pool area. The private primary suite is tucked away on its own and includes direct lanai access, two spacious walk-in closets, a large shower and two separate vanity areas. The kitchen is the heart of the home, with custom cabinetry, new KitchenAid black appliances, a center island, and a breakfast bar. It opens to both the dinette and family room, where an impressive wood-plank tray ceiling, decorative tile accent wall and electric fireplace create a warm and inviting gathering space. Toward the rear of the home are two Jack-and-Jill bedrooms with a shared bath. You’ll also find an office or den with built-ins, along with another full bath offering convenient access to the lanai. The staircase is discreetly tucked toward the back of the home and leads to an oversized bonus room,spacious bedroom, and additional full bath offering convenient- perfect for guests, extended family, a media room or private retreat. Thoughtful finishes continue throughout the home with attractive ceiling fans and light fixtures. Also located on the first floor is a dedicated laundry room tucked away off a hallway convenient to the kitchen. A two car oversized garage completes the first floor. Outdoor living is equally impressive. The lanai offers a large covered entertaining area, outdoor BBQ and easy access to the pool. The exterior features new sod and a circular paver driveway, adding to the home’s curb appeal. Other extra features include foam insulation in the roof, attic area and the exterior walls. Extra insulation added between master and living room and then shared wall for family room and bedroom. Southbay is a golf-cart-friendly community with something for all ages. Residents enjoy an active clubhouse with a fitness center, gathering rooms, two kitchens, ball room, card room, library, pickleball and tennis courts, bocce ball, basketball, kayak launch and storage, and a community pool overlook the marina. One of Southbay’s standout features is its resident-only marina, capable of accommodating a wide range of boat sizes at very reasonable slip rates, with direct access to the Intracoastal Waterway. The popular Casey Key Fish House and Tiki Bar is just an easy boat, golf-cart, or car ride away. Southbay is also conveniently located near restaurants, shopping, major roadways, and the Legacy Trail. Beautiful Gulf beaches are close by with Siesta Key less than 10 miles away and Nokomis Beach less than 5 miles away. Come see everything this special home - and the Southbay lifestyle - has to offer!

1417 Landview Lane, Osprey

$2,600,000

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

This 4 bedroom, 4 bath gem will please the most discriminating buyer. You will be immediately intrigued when you pull into the pavered circular driveway. Once you enter though the double front doors, you will feel like you’ve stepped into the pages of a magazine. There is no end to the delightful touches you will find; bathrooms with designer tile, walls sanded to a smooth finish and expertly painted, high-end custom light fixtures throughout and the absolutely stunning master bathroom, to name a few. You will be so taken with the interior that you might think the outside cannot be any better, but wait until you see the gorgeous, expanded lanai with summer kitchen, stone pool deck, and resort-like pool. Beautifully landscaped, the lot appeal of this home is incredible. You truly must see all it has to offer to appreciate how special it is. Imagine living in this gracious home behind the gates of The Oaks Club. The Oaks, Sarasota’s premier golf and country club, offers two championship golf courses, pickleball courts, 12 HAR-TRU tennis courts, tournament croquet court, state of the art WellFit Center and a wide variety of dining, recreational and social options. Membership in The Oaks Club is required with homeownership. There is currently no waiting list for either Golf or Sports/Social membership.

794 Lytham Circle, Osprey

$1,577,990

3 Beds ⋅ 3 Baths ⋅ Aria SubDv. ⋅ 34275 Zip Code

SOLD DATA ONLY. BUILDER MODEL PURCHASE.

316 Aria Drive, Nokomis

$819,000

3 Beds ⋅ 4 Baths ⋅ Venice Woodlands SubDv. ⋅ 34275 Zip Code

This beautifully appointed 2024 Toll Brothers residence offers over 3,000 square feet of thoughtfully designed living space in the gated community of Venice Woodlands. Set on a quiet cul-de-sac with an oversized driveway, three-car garage and a private backdrop of lush, mature vegetation, this West Indies-inspired home combines refined finishes, generous spaces and the ease of nearly new construction. The Sanderling Elite floor plan welcomes you through a covered, screened entry and foyer into a soaring great room and dining area, where tray ceilings and a custom electric fireplace create an inviting focal point. The open layout draws your eye through the home to the expansive screened and covered lanai beyond, allowing one to open up the home on both sides, letting the breeze flow through and offering a private setting for outdoor dining, entertaining or simply enjoying the surrounding greenery. At the heart of the home, the beautifully designed kitchen features quartz countertops, cabinetry extending to the ceiling and an oversized center island with breakfast-bar seating. Additional cabinetry along the back of the island provides valuable hidden storage, while a sizable pantry and abundant counter space make the kitchen as functional as it is attractive. A bright casual dining area sits just beyond. The spacious primary suite is a retreat, featuring expansive custom built-out closets and a spa-inspired bath with dual vanities, an oversized walk-in shower, linen storage and a private water closet. Secondary bedrooms offer generous closet space, while a versatile flex room provides additional space for a home office, den or sitting room. Upstairs, a secluded oversized loft (which can easily be converted into a fourth bedroom and full bath) with its adjacent powder room creates an ideal bonus space for guests, a media room, game room or second living area. Built with comfort and peace of mind in mind, the home features whole-home hurricane impact windows, a flat tile roof, full gutter system and a comprehensive home security system. The property is also outside a designated flood hazard area. Beyond the home, Venice Woodlands offers a relaxed, resort-style lifestyle with a community pool, clubhouse, fitness center, pickleball courts and bocce ball. Low HOA fees include individual-home lawn maintenance, making ownership even more effortless, and there is no CDD fee. Conveniently near the best of Venice and Nokomis, this exceptional home offers the rare combination of newer construction, substantial square footage, privacy, thoughtful upgrades and community amenities. Zoned for Laurel Nokomis Elementary School, Laurel Nokomis Middle School and Venice High School, all included on the Excellent List.

469 Baneberry Court, Nokomis

$6,000,000

6 Beds ⋅ 6 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

A rare combination of timeless grandeur and effortless waterfront living, this bayfront estate in The Oaks Bayside commands approximately 150 feet of Bay frontage across 0.60 acres, with water views framing nearly every principal room. The residence offers 6 bedrooms, 5.5 baths, multiple covered balconies overlooking the Bay, additional ground-level flex space and a side-entry 3-car garage. A circular brick-paver driveway, tropical landscaping and a stately columned entrance create an unforgettable arrival. The dramatic two-story foyer features architectural columns, custom millwork and a wood-clad ceiling accent. European French white oak engineered flooring flows through the main living spaces. The living and family rooms feature soaring ceilings, extensive millwork, statement lighting, carved-stone fireplaces and oversized windows framing expansive water views. An adjoining sitting area features arched windows, a wood-clad ceiling and multiple glass doors opening to the waterfront balcony. The new kitchen is appointed with ceiling-height Shaker cabinetry, champagne-bronze hardware, marble countertops and an oversized waterfall island with seating for five. A GE Monogram appliance suite includes a professional gas range with griddle, refrigerator and dishwasher. A custom range hood, dimensional tile backsplash, apron-front sink and walk-in pantry complete the space. The waterfront dining nook incorporates built-in cabinetry, a stone serving counter and beverage cooler, while the formal dining room features a tray ceiling, paneled walls and columns. A waterfront office with built-in bookshelves, fireplace and balcony access, an updated laundry room and multiple en-suite guest accommodations complete the main level. Upstairs, the landing overlooks the living spaces beneath a crystal chandelier. The primary suite offers separate sleeping and sitting areas, a carved-stone fireplace, wide water views, private balcony access and two walk-in closets with custom storage. Its spa-inspired bath includes dual furniture-style vanities, a freestanding soaking tub beneath a picture window and an oversized frameless shower with marble-look tile, rainfall and handheld fixtures. Additional bedrooms offer en-suite or nearby baths, walk-in closets, abundant natural light and water or tropical views. Multiple covered balconies overlook the newly resurfaced pool, paver terrace, manicured lawn and waterfront. The pool features a 7-foot depth, entry steps, seating or sun-shelf areas, lighting, a self-cleaning system and a new pump. A private walkway through the mangroves leads to a new 5-by-60-foot composite dock completed in 2026, equipped with electric, water and a 6,000-pound boat lift. The property also features a concrete seawall and direct boating access. The lower level provides substantial additional flexibility for recreation, fitness, media or entertaining. Further updates include a newer 2023 tile roof, new HVAC, all-new appliances and flooring, new interior doors and moldings, hurricane protection and exterior lighting. The renowned Oaks Club is one of the area’s premier member-owned clubs, featuring two championship 18-hole golf courses, a full slate of tennis and fitness facilities, and an elegant clubhouse offering fine dining and a vibrant social calendar. Ideally situated in Osprey, the property offers convenient access to Gulf beaches, the Legacy Trail, dining and shopping, with downtown Sarasota and Venice both within easy reach.

112 Osprey Point Drive, Osprey

$9,750,000

5 Beds ⋅ 8 Baths ⋅ Casey Key SubDv. ⋅ 34229 Zip Code

At the northernmost point of Casey Key, where the Gulf meets the tranquil waters of Little Sarasota and Blackburn Bay, an extraordinary private estate unfolds between two worlds of water. Beyond a secluded entrance lies a residence of remarkable distinction, an Italianate architectural masterpiece spanning more than 8,000 square feet, with a private sandy beach on the Gulf and a rare, grandfathered covered boat lift on the bay. Designed by renowned architect Clifford A. Scholz and masterfully built by Delta Southern Construction, the estate was envisioned not simply as a home but as a setting for an exceptional life. Here, timeless architecture, impeccable craftsmanship and modern coastal luxury converge in a residence designed to bring family and guests together while preserving moments of treasured privacy. From the moment of arrival, the architecture reveals a quiet sense of grandeur. Cypress-beamed ceilings, graceful arches, French doors, handcrafted millwork, and luminous water views create a sequence of spaces that feel both magnificent and deeply welcoming. The living room commands a captivating panorama across the Bay, while walls of glass and elegantly framed openings blend the boundary between interior and landscape. The culinary spaces are equally impressive. A sophisticated kitchen is complemented by a dedicated wine cellar, butler’s pantry, and wet bar—an entertainer’s dream conceived for intimate dinners and spectacular gatherings alike. Beyond, a grand media room provides an elegant retreat for cinematic evenings, music, and cultural pursuits. The primary suite is a private sanctuary unto itself. A serene sitting room, sumptuous bath, dual closets, breakfast nook, and expansive water views create an atmosphere of effortless indulgence. Three additional bedroom suites offer luxurious accommodations for family and guests, while a fifth suite transforms into a private wellness retreat with a home gym, steam room, and sauna. A magnificent marble staircase leads to an office and library distinguished by leaded-glass doors, handcrafted built-in shelving, a coffered ceiling, and mesmerizing Gulf views. Throughout the residence, additional spaces for recreation, relaxation, and quiet spaces have been thoughtfully integrated, ensuring that every corner serves the extraordinary rhythm of life on the water. Outside, stone terraces cascade toward a shimmering infinity pool, where the architecture gives way to sky and water. Days unfold between the pool and the Gulf, afternoons drift toward the bay, and evenings become unforgettable beneath the coastal sky. For the boating enthusiast, the deep-water dock offers quick access with no bridges to the Gulf through Midnight Pass and features one of the area’s rare grandfathered covered boat lifts. For those drawn to the Gulf, a private sandy beach provides a front-row seat to spectacular sunsets and the timeless beauty of the sea. Yet perhaps the estate’s greatest luxury is its sense of place. North Casey Key remains one of Sarasota County’s most coveted enclaves—a sanctuary of quiet privacy and natural beauty, remarkably close to world-class golf, tennis, dining, shopping, and the cultural attractions of Sarasota. This is more than an exceptional residence. It is a private coastal world—an irreplaceable estate where architecture, water, nature, and the art of gracious living come together in extraordinary harmony.

1216 N Casey Key Road, Osprey

$1,060,000

10 Beds ⋅ 6 Baths ⋅ 34275 Zip Code

ONE OF A KIND! - PRICED $200,000 BELOW RECENT APPRAISAL!!! - 5 ACRES- 2 HOMES- 1 CURRENTLY USED AS A BUSINESS OFFICE- 8 CAR GARAGE with SECOND OFFICE. PERFECT FOR A BUSINESS-EMPLOYEE HOUSING-OR LARGE FAMILY. 10 MINUTES TO THE BEACH- 5 MINUTES TO I-75 and Sarasota Memorial Hospital Venice. TOTAL 10 BEDROOMS- 6 BATHROOMS- HUGE POOL-Great Location close to everything including new Walmart and Home Depot currently being built on Laurel Rd. Rare opportunity for a business owner seeking private acreage with on-site housing, office space, parking and storage. This 5-acre property features two separate homes, an 8-car garage with its own office, large circular driveway, abundant parking, and a combination of wooded and cleared land. Adjacent property is preserved and cannot be built on. The main home offers 7 bedrooms, 3½ baths, two huge family rooms, a spacious kitchen, extensive storage and a large pool. Four bedrooms are located upstairs with access from a private second-story staircase. The main home needs updating and repairs but offers tremendous potential for owner or employee housing. The second home is currently used as a professional office and is in very good condition, with possible 3 bedrooms (currently 2) 1½ baths, full kitchen, large family room and an additional open meeting area that could serve as another living or recreation space. It includes a computer room and propane-powered backup generator. Second home is built with storm resistance in mind. The 8-car garage with private office provides exceptional space for vehicles, equipment, inventory or business operations. A Beautiful picnic area and partially fenced yard complete the property. Ideally located approximately 10 minutes to the beach, 5 minutes to I-75, and less than 5 minutes to shopping, restaurants and a soon to be built Walmart and Home Depot on Laurel Rd. An exceptional opportunity for a business owner needing employee housing, an on-site office, equipment storage and plenty of parking, all in one private property. Please refer to Sarasota County for information concerning your particular use.

411 Bristol Lane, Nokomis

$2,095,000

4 Beds ⋅ 4 Baths ⋅ Southbay Yacht & Racquet Club SubDv. ⋅ 34229 Zip Code

Welcome to exceptional Florida living in the highly sought-after Southbay Yacht & Racquet Club. Offering approximately 4,578 square feet under roof, this spacious 4-bedroom, 3.5-bath residence combines beautifully updated interiors, exceptionally generous rooms and an extraordinary indoor-outdoor lifestyle. The heart of the home is a completely renovated kitchen featuring quartz countertops, soft-close cabinetry and drawers, built-in organizers, pull-out spice storage, a specialty appliance lift for a mixer or blender, a new refrigerator and dishwasher, and abundant functional storage. The main living area is anchored by a fully functioning wood-burning fireplace with an elegant travertine stone surround, adding warmth and character to the home. All four bedrooms are exceptionally spacious and feature large walk-in closets with custom organization systems. The primary suite and a guest bedroom are conveniently located on the first floor, providing an ideal layout for family and guests. Additional conveniences include a whole-home central vacuum system and a spacious two-car garage with an already-installed Tesla EV charging station. Major recent improvements provide additional peace of mind, including two brand-new air-conditioning systems and brand-new hurricane-rated windows installed in August 2026. The outdoor living space is truly a standout. More than 1,500 square feet of screened lanai and outdoor living area surrounds an exceptionally large residential pool ranging from approximately 3 to 8 feet deep. Two covered outdoor areas provide comfortable spaces for entertaining and relaxing, including an outdoor kitchen with a brand-new THOR grill and a separate covered TV lounge area. A pool bath is conveniently accessible directly from the lanai. Across the back of the pool enclosure, an impressive approximately 50-foot panoramic screen creates a virtually unobstructed view with no intermediate posts interrupting the sightline. Beyond the pool is an expansive green space, creating a wonderful sense of openness and privacy. The newly landscaped yard and more than 25 palm trees lining the backyard complete the lush, tropical setting. Living in Southbay Yacht & Racquet Club is about much more than the home itself. Residents enjoy an impressive collection of community amenities, including a clubhouse, heated community pool, fitness center, tennis courts, pickleball courts, basketball courts, bocce ball, library, card and game room, ballroom and banquet facilities, and the community’s highly desirable marina, where residents have opportunities to rent or lease boat slips, subject to availability. The location is equally exceptional. Pine View School is approximately one mile away, while the bay, Gulf beaches, Publix, restaurants, coffee shops, fitness and yoga studios, CVS and everyday conveniences are all close at hand. The golf-cart-friendly community makes enjoying the neighborhood and surrounding area even easier. From its oversized bedrooms and beautifully renovated kitchen to its remarkable pool, panoramic screened view and expansive outdoor entertaining areas, this home offers an uncommon combination of space, thoughtful upgrades and Florida lifestyle. Add the boating and recreational amenities of Southbay Yacht & Racquet Club, and this is a home designed to enjoy everything the Sarasota area has to provide.

154 Lookout Point Drive, Osprey

$1,100,000

5 Beds ⋅ 4 Baths ⋅ Pine Ranch East SubDv. ⋅ 34229 Zip Code

Welcome to this rare slice of coastal paradise tucked away in the boutique enclave of Pine Ranch East in Osprey, Florida. Situated on a sprawling 1.137-acre private lot, this magnificent residence offers an extraordinary blend of space, serenity, and convenience. The property boasts five spacious bedrooms and three-and-a-half baths, providing a flexible layout designed to accommodate large families, host overnight guests, or create dedicated home office spaces. Every detail of the interior reflects thoughtful maintenance and pride of ownership, offering a seamless flow between the primary living areas. Designed for quintessential Florida living, the expansive backyard functions as your own private resort. Step out onto the oversized covered lanai to entertain year-round, or cool off in the crystal-clear heated pool and integrated spa while taking in the tranquil scenery of your secluded acreage. Despite the incredible privacy, you are just minutes away from pristine Gulf beaches and iconic local dining hot spots like Pops Sunset Grill and the Casey Key Fish House. Adding to the unmatched value of this property is its setting within Pine Ranch East, an exclusive neighborhood comprised of only 26 homes. While the community maintains an established HOA structure, homeowners enjoy the astonishing benefit of paying no HOA fees thanks to a unique financial setup that leaves the neighborhood fully funded years into the future. Contact us today to learn more about this remarkable community story or to schedule your private tour.

296 Pine Ranch Trail, Osprey

$1,100,000

4 Beds ⋅ 3 Baths ⋅ Rivendell The Woodlands SubDv. ⋅ 34229 Zip Code

Under contract-accepting backup offers. UNMATCHED VALUE SCALE IN RIVENDELL – PRICED AT ONLY $276/SQ FT! Escape to estate-scale luxury on a private lake lot, directly within walking distance to the nationally top-ranked Pine View School. Spanning nearly 4,000 square feet, this 4-Bedroom + Huge Bonus Suite home offers a level of value impossible to duplicate at this price point. ZERO CAP-EX FOR THE NEXT DECADE: Buy with ultimate peace of mind. Featuring a BRAND NEW TILE ROOF (2025), newer dual A/C units, a newer water heater, and a mix of impact-resistant glass/shutters—your insurance premiums and maintenance costs are heavily optimized. CHEF'S KITCHEN & PREMIUM LAUNDRY: The interior heart of the home features a premium suite of all-Bosch kitchen appliances, offering high-end reliability and sleek European design, paired with an ultra-durable Speed Queen commercial washer and dryer set in the laundry wing. THE ULTIMATE RESORT BACKYARD: The private lanai is a personal paradise featuring a sparkling saltwater pool overlooking a peaceful preserve and lake. The chef-grade outdoor kitchen comes fully equipped with a built-in double tap kegerator, built-in 3-Burner BBQ grill with Rotisserie and a custom Big Green Egg station—perfect for sunset entertaining. Upstairs, the massive 22x21 bonus wing is perfect for a multi-generational suite, homework lounge, or executive office. Do not pay higher unit-rates for less space; maximize your equity at 907 Eagle Isle Court. Schedule your private tour today!

907 Eagle Isle Court, Osprey

$1,175,000

5 Beds ⋅ 4 Baths ⋅ Cassata Lakes SubDv. ⋅ 34275 Zip Code

Virtually Staged. REDUCED! RARE NEVER LIVED IN! Be the FIRST TO SWIM IN 2026 BUILT NEW POOL! This is your own amenity luxury living! Minutes to Nokomis Beach, historic downtown Venice, and Sarasota Memorial Hospital. Built in 2025, this pristine 2-story Juniper model by M/I Homes features 5 beds, 4 baths, a bonus loft, flexible den, and a 3-car epoxy garage equipped with setup for your choice of EV charger. Offering 3,759 sq ft of heated living space on an oversized water-view lot, this property defines high-prestige Florida living. For the discerning buyer demanding exclusivity, this clean, fresh, crisp canvas offers immediate gratification without the stress of a new build or the grueling 10-month hassle of pool construction. It is 100% move-in ready today, serving as a flawless backdrop ready to customize to your exact taste. Every square inch has been engineered with approx. $172K in rare, high-expense upgrades that elevate daily living into an art form Fortified for absolute peace of mind, the home features full hurricane impact windows, extra-high sliding glass doors, 3 exterior security cameras, a RING camera, and an intelligent smart outdoor camera with built-in AI. The advanced tech infrastructure is highlighted by a premium, dual-floor Wireless Access System with a high-power wireless access point on each level for seamless coverage, alongside professional networking options featuring built-in RG6 and CAT6 wiring. Exquisite details include soaring ceilings, custom crown molding, open stair rails, custom wood blinds, and marble window ledges. Elegant tray ceilings pair with extra canned recessed lighting, while premium, hard-to-find Karastan RevWood white-oak flooring and an upscale wood closet system ground the interior structural elegance. The gourmet kitchen is a true showpiece, anchored by rare leathered-finish quartz countertops with a sophisticated matte aesthetic and unparalleled durability. This chef's space features an oversized island, premium Kohler farmhouse sink, GE Profile appliance integration, under-cabinet lighting, and cabinets with slide-out shelving. Indulge in the master suite's ultra-exclusive en-suite bath sanctuary—the only layout of its kind in Cassata Lakes. This private masterpiece features an extra-large Kohler soaking tub, oversized frameless glass shower with rain head and seating, and an extended area that flows into the custom walk-in closet and straight into the massive laundry room equipped with washer/dryer, utility sink, folding area, and custom cabinets. The layout seamlessly transitions to outdoor entertaining. Open the extra-high impact sliders to an exquisite travertine pool deck and a spectacular, brand-new custom heated pool and spa against panoramic water views. Enjoy hidden outdoor plumbing lines completely pre-plumbed for your custom outdoor kitchen, all completely enclosed by a premium frameless clear-view lanai cage for unobstructed vistas. Carrying NO CDD fees and a remarkably low HOA of only $119/month, you can avoid building delays and claim your flawless paradise right now! Watch the captivating video tour to experience this rare gem—you must see it to believe it, so schedule your showing today! BUYERS: Must see the sensational VIDEO TOUR that brings this home to life! Watch by scrolling to "Facts & features," clicking "See more," and selecting "Virtual Tour" at the bottom.

1669 Lugano Circle, Nokomis

$2,750,000

4 Beds ⋅ 5 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Experience refined living in this extraordinary, elegant home. With 3 bedrooms and 4.5 baths it offers expansive lake and golf course views from its premier position along the Heron Course. Designed for both grand entertaining and everyday comfort, the home features generous living spaces, a bright open kitchen overlooking the family room with wood burning fireplace, and a luxurious primary suite with two walk-in closets and a spa style bath. Each guest suite includes its own private bath, ensuring comfort and privacy. Outdoor living shines with a dramatic pool, and spacious covered areas ideal for sunset dining, and beautiful views. Residents enjoy access to The Oaks Club’s renowned amenities, including two championship golf courses, tennis, pickleball, and a vibrant social calendar. Membership is required with homeownership. There is currently no wait list for either Golf or Sports/Social Membership.

447 E Macewen Drive, Osprey

$1,800,000

3 Beds ⋅ 4 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Beautifully maintained Arthur Rutenberg 3 bedroom, 3.5 bath home located on a quiet cul-de-sac. This architecturally inspired residence features crown molding, marble, tile and hardwood flooring, coffered ceilings, granite countertops, and a travertine pool deck. The first floor master suite includes a sitting area and private access to the lanai and pool. The outdoor living area offers an architectural enclosure, lush landscaping, and a built-in stainless steel gas grill. Two second-floor en-suite bedrooms plus a spacious bonus room provide excellent flexibility for guests or additional living space. This must-see home, with timeless finishes and exceptional care throughout, situated in St. James Park behind the gates of The Oaks Clubside, offers picturesque views from the incredible lanai. The Oaks Club’s unmatched amenities include two championship 18-holf golf courses, 12 tennis courts and 4 pickleball courts, the state-of-the-art WellFit Center, a junior Olympic pool, a celebrated social calendar, and a wide array of dining options and recreational activities. There is currently no waiting list for either Golf or Sports/Social membership.

222 Saint James Park, Osprey

$3,650,000

4 Beds ⋅ 4 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code

Tucked away at the end of Cutlass Bayou, this extraordinary 1.2-acre private peninsula offers a setting that is increasingly difficult to find on Casey Key. Completely redone and sold furnished this property is Surrounded by water on three sides with approximately 900 feet of shoreline, the property feels like its own secluded island retreat, with sweeping bay views, protected water, mature tropical landscaping, and deeded access to the sandy beaches of the Gulf of Mexico. The property is anchored by a charming 1950 main residence with a separate guest suite, accompanied by a distinctive 1968 artist studio designed by noted architect Edward “Tim” Seibert", an important contributor to Sarasota’s celebrated mid-century modern architectural movement. Together, the structures offer a glimpse into the architectural character that has long made Casey Key so special. Wander beneath a canopy of mature trees along the southern shoreline, where meandering trails lead to a peaceful waterfront deck—a quiet place to read, relax, or simply enjoy the shade and solitude. On the northwest point, wide-open bay views provide the backdrop for a waterfront Tiki hut with an outdoor kitchen and bar, ideal for sunset cocktails, entertaining friends, or preparing the day’s fresh catch. Just steps from the main residence, the bayfront swimming poo overlooks the water and offers the perfect place to cool off after a day of boating, fishing, paddleboarding, or exploring the Intracoastal Waterway. Along the protected northern harbor of the bayou, plans are available for a proposed substantial new dock, creating exciting possibilities for the boating enthusiast. And when the Gulf is calling, simply cross Casey Key Road to your deeded Gulf beach easement and enjoy the sand, surf, and spectacular sunsets that define the Casey Key lifestyle. The opportunity here is as remarkable as the setting. With 1.2 acres, extraordinary shoreline, Gulf access, bayfront living, and remarkable privacy, the possibilities are compelling. Located on desirable Casey Key, between Siesta Key and the Island of Venice, the property offers a rare combination of seclusion and convenience. Blackburn Point Road provides easy access on and off the island, while restaurants, boutiques, shopping, Sarasota, Venice, and I-75 are all within convenient reach. A magical lane. A private peninsula. Bay on three sides and the Gulf just across the road. This is more than a waterfront property—it is an opportunity to create your own legacy on Casey Key.

3780 Cutlass Bayou Road, Nokomis

$651,900

4 Beds ⋅ 4 Baths ⋅ Magnolia Bay SubDv. ⋅ 34275 Zip Code

Under Construction. The two-story front porch welcomes you into the entryway. A secluded guest suite with full bathroom and large walk-in closet is off the main entrance. French doors lead into the home office that offers plenty of natural light. The kitchen features a large island with built-in seating and corner walk-in pantry. The dining area is embraced by a corner of windows and allows access to the backyard covered lanai. The family room boasts tall ceilings. The primary bedroom has three large windows and a tray ceiling. Double doors lead to the bathroom which has dual vanities, a garden tub, glass enclosed shower, and oversized walk-in closet. Upstairs you are greeted by the game room which is surrounded by windows on two sides. Two secondary bedrooms each with walk-in closets and a shared bathroom complete the second level. The home offers ample storage throughout. The laundry room is located off the three-car garage that opens into the drop zone area.

285 Holly Bank Avenue, Nokomis

$1,250,000

4 Beds ⋅ 4 Baths ⋅ Shore Oaks SubDv. ⋅ 34275 Zip Code

This EXCEPTIONAL WATERFRONT residence presents an outstanding opportunity to own a custom-built GULF-ACCESS home just 1.25 miles from Nokomis Beach. Nestled on an OVERSIZED CUL-DE-SAC LOT within the gated, deed-restricted community of Shore Oaks, this impressive 4-bedroom + den, 3.5-bath residence with a detached casita, 3-car garage, pool, spa, private dock, and boat lift offers the ultimate Florida lifestyle. Built by MPS Custom Homes, the thoughtfully designed split-bedroom floor plan provides exceptional privacy, while the detached casita with its own private entrance is ideal for guests, a home office, studio, fitness room, or multigenerational living. Designed for seamless indoor-outdoor living, the main residence surrounds a spectacular courtyard-style lanai where the living room, family room, kitchen, primary suite, and guest bedroom all open to the resort-inspired outdoor oasis. Enjoy a beautifully resurfaced PebbleTec pool and spa, expansive covered entertaining space, a fully equipped outdoor kitchen, pool bath, and outdoor shower—all surrounded by lush tropical landscaping. The heart of the home is the spacious chef's kitchen featuring 42-inch maple cabinetry, stone countertops, stainless steel appliances, a generous walk-in pantry, breakfast bar, and a sun-filled breakfast nook highlighted by a dramatic mitered glass window overlooking the pool. The luxurious primary suite offers a tray ceiling, private lanai access, and dual walk-in closets. A guest bedroom enjoys pool access and tranquil canal views, while another oversized bedroom provides exceptional flexibility and abundant storage. The detached casita serves as the fourth bedroom complete with its own ensuite bath. Boating enthusiasts will appreciate the 35-foot private dock with boat lift on a saltwater canal offering Gulf access. Additional recent improvements include hurricane-impact windows and sliding glass doors, tile roof, PebbleTec pool resurfacing, and fresh interior and exterior paint, providing peace of mind for years to come. The private motor court enhances both curb appeal and functionality with additional off-street parking beyond the oversized three-car garage. Conveniently located near Nokomis Village, waterfront dining, the Legacy Trail, Oscar Scherer State Park, Historic Downtown Venice, A-rated schools, and some of Florida's most beautiful Gulf beaches, this is a rare opportunity to own an exceptional waterfront property in one of Nokomis' most desirable communities. Exceptional value. Exceptional location. Exceptional lifestyle. Schedule your private showing today. Please note: the home is no longer staged as shown in the photographs. Updated photography to follow.

321 Dulmer Drive, Nokomis

$624,979

5 Beds ⋅ 4 Baths ⋅ Tiburon SubDv. ⋅ 34275 Zip Code

What's Special: Corner Lot | Large Game Room | Close to Amenities. New Construction - Ready Now! Welcome to the Bermuda at 7028 Foxboro Way in Tiburon! This home offers five bedrooms, four bathrooms, and exceptional flexibility for modern living. The gourmet kitchen features a large center island, walk-in pantry, and flows to the casual dining area and great room, creating the perfect space for everyday gatherings. The private primary suite is tucked away on the main level and showcases elegant tray ceilings, a spacious walk-in closet, and the convenience of a direct interior door from the primary closet to the laundry room. A first-floor secondary bedroom with a nearby full bath is ideal for guests, while the second level offers three additional bedrooms, one with an en-suite, and an additional shared bathroom, and a generous game room that provides space for recreation, media, or study. Sliding glass doors open to an oversized covered lanai, extending the living space outdoors for year-round enjoyment. Tucked away in a peaceful Sarasota County setting on 40 acres, Tiburon offers the warmth and intimacy of a boutique community - where neighbors know each other and life moves at a more relaxed pace. With just the right blend of privacy and connection, Tiburon is ideal for those seeking a quieter, more personal lifestyle. Additional Highlights Include: whole house impact windows, 8' interior doors, and outdoor kitchen rough-in. MLS#A4702391

7028 Foxboro Way, Nokomis

$599,764

5 Beds ⋅ 4 Baths ⋅ Tiburon SubDv. ⋅ 34275 Zip Code

Virtually Staged. What's Special: Close to Amenities | Close to Trails | Flex Room | Loft | 5th Bedroom. New Construction – Ready Now! Welcome to the Bermuda at 7024 Foxboro Way in Tiburon! This spacious new home has a thoughtfully designed layout with five bedrooms, four bathrooms, and inviting living spaces throughout. Just beyond the foyer, a secondary bedroom and full bathroom provide flexibility for guests or a home office. The open-concept gourmet kitchen, casual dining area, and great room create the perfect setting for entertaining, with easy access to the extended covered lanai for seamless indoor-outdoor living. The private primary suite is tucked away on the main level and features an en-suite bath and walk-in closet with direct access to laundry room. Upstairs, three additional bedrooms, one with an en-suite bath, and a versatile loft provide plenty of space to relax, work, or play. Tucked away in a peaceful Sarasota County setting on 40 acres, Tiburon offers the warmth and intimacy of a boutique community - where neighbors know each other and life moves at a more relaxed pace. With just the right blend of privacy and connection, Tiburon is ideal for those seeking a quieter, more personal lifestyle. Additional Highlights Include: Whole house impact windows, tray ceiling pkg, shower at bath 3, pocket slider at great room, 8' interior doors, single pocket door at bed five to bath, and pre-plumb for future laundry sink. MLS#A4702375

7024 Foxboro Way, Nokomis

$949,900

3 Beds ⋅ 6 Baths ⋅ Toscana Isles SubDv. ⋅ 34275 Zip Code

Embrace the enchanting waterfront lifestyle you’ve always dreamed of with this breathtaking Easton floor plan, perfectly positioned on a premium and oversized lakefront lot that features a sparkling bright southern exposure. This remarkable home is crafted for today’s living, featuring three generously sized bedrooms and a den on the first floor, four full bathrooms, two half bathrooms, an oversized second story bonus room with full bath, and an impressive three-car garage. You will love the extended lanai, equipped with a luxurious outdoor kitchen designed specifically for the modern homeowner who enjoys entertaining and cooking al fresco. As you explore this exceptional residence, you’ll be captivated by the thoughtful upgrades seamlessly woven throughout. Feel secure behind hurricane impact windows and doors, while you relax and take in the high quality, luxury interior details such as elegant wood plank porcelain tile flooring that graces the downstairs, the stately 8-foot doors complemented by sophisticated baseboards and crown molding, and the stunning Restoration Hardware crystal chandeliers that add a refined touch of glamour to your living spaces. The expansive, open-concept kitchen is a true haven for any chef. It features upgraded white modern cabinets with soft-close drawers and doors and pull-outs, and striking granite countertops with matching backsplashes that enhance the elegance of the space. You will truly appreciate the well-thought-out split floor plan, ensuring your private primary suite is tucked away at the back, providing a peaceful retreat, while the additional bedrooms at the front are conveniently accessible. Plus, a spacious office/den elevates the functionality of your living area. Your lavish primary suite is designed for relaxation, showcasing two generous walk-in closets and a luxurious, oversized walk-in shower. Dual sinks and a handy separate linen closet add to the convenience. Guests will enjoy the thoughtfully designed second bedroom, which comes complete with its own en-suite bath featuring a walk-in shower, ensuring everyone’s privacy. Enjoy your hobbies in the incredible 600-square-foot upstairs multipurpose bonus room featuring its own private full bath, or if needed, use it as an additional bedroom. Step outside to discover a vast covered lanai, perfect for relaxation, along with a caged extended patio with panorama view screen. The outdoor kitchen is a culinary delight, complete with a spacious grill, sink, two beverage refrigerators, warming drawer, and an impressive stainless steel vent hood. Welcome to the vibrant Toscana Isles community, where an active lifestyle awaits! You can indulge in kayaking, canoeing, and fishing on over 200 acres of interconnected lakes, all just a stone’s throw from your home. The fabulous 8,000-square-foot clubhouse invites you to explore an array of amenities including a state-of-the-art fitness center, a grand ballroom perfect for gatherings, and a billiards room for enjoyable game nights. Beautiful Nokomis Beach is just six miles away, a quick 10-minute drive! You’ll also find easy access to the Legacy Bike Trail and the vibrant downtown areas of Venice and Sarasota, brimming with culture, shopping, and gourmet dining options. Plus, the nearby new Sarasota Memorial Hospital Venice Campus ensures added peace of mind and accessibility. Dive into this wonderful lifestyle today, you truly deserve it!

289 Villoresi Boulevard, Nokomis

$1,612,500

5 Beds ⋅ 8 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Virtually Staged. A rare canvas of luxury, positioned on a lush double lot within the sought-after, gated community of The Oaks, in Osprey, adjacent to stunning Sarasota, known for the arts. Bordering the Heron Course on the eighth fairway, this iconic two-story estate boasts incredible opportunity for limitless potential. The entire interior is freshly painted, to enhance vision of stateliness. With five bedrooms, 7.5 baths and a sprawling layout, this magnificent property is an exceptional backdrop, just waiting for your personal touch. Arrive in style via the elegant front circular driveway or utilize the private rear driveway leading to a rare four-car garage. Inside, the home is masterfully designed for grand entertaining and everyday comfort, with a sweeping curved stairway at the entrance, setting the stage to an exquisite residence. The first floor features a formal living room and a sun-drenched family room complete with a fireplace, custom built-ins and multiple French doors, leading to the outdoor bliss. A screened lanai lays the foundation for Florida living at its finest, showcasing an enormous 33-by-46-foot sparkling heated pool and spa, expansive patio and an outdoor kitchen. The expansive open kitchen is a chef's dream, flowing seamlessly into a casual breakfast nook. For formal affairs, the large dining room offers custom cabinetry and an adjacent wet bar. The main-floor primary retreat is a sanctuary, featuring a dedicated sitting area and luxurious dual en-suite baths. There is more closet space than a clothes diva could possibly desire. The first floor is completed by a handsome office/library with built-ins, a powder room and a guest bedroom. Upstairs, you will find three additional en-suite bedrooms, one of which benefits from private back-staircase access, ideal for an au pair, in-laws or VIP guests. With every bedroom featuring its private bath, privacy is guaranteed for all. Outdoors, the walled double lot provides a private tropical oasis, all with tranquil, serene views. On a practical note, roof was replaced in 2019, with hurricane shutters, for peace of mind. Two 18-hole championship golf courses, 12 Har-Tru tennis courts (four lighted), croquet and pickleball courts, a state-of-the art fitness center, fine and casual dining options and a calendar of social events, The Oaks is Sarasota’s leading golf and country club.

916 Macewen Drive, Osprey

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