Osprey/Nokomis FL 5000+ Sq. Ft. Real Estate, Homes, Condos for Sale - Ed Grabowski

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

$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

$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

$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

$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

$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

$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

$1,612,500

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

$11,950,000

5 Beds ⋅ 6 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code

Pre-Construction. To be built. An extraordinary opportunity on Casey Key, set across 1.37 private acres with an exceptional 300 feet of deep-water bay frontage, one of the most expansive and coveted waterfront parcels on the island. Thoughtfully designed as a modern coastal estate, this residence will offer over 5,400 square feet under air, featuring 5 bedrooms, 5 full baths, 1 half bath, a private elevator, and a 5 car garage, all crafted to capture sweeping panoramic water views from nearly every room. Floor-to-ceiling glass, soaring ceilings, and seamless indoor-outdoor transitions define the home’s architectural vision, blending refined design with the natural beauty of its surroundings. The open-concept layout is designed for both elevated daily living and effortless entertaining, with expansive living spaces that flow onto multiple waterfront terraces. Outdoor living is equally impressive, anchored by a resort-style pool and spa, outdoor kitchen, and generous lounge areas overlooking Sarasota Bay. The property’s significant water frontage allows for an extended private dock with excellent depth, ideal for accommodating larger vessels and delivering direct access to the Intracoastal Waterway and Gulf. Adding to its rarity, the estate includes deeded beach access directly across the street, offering private entry to the pristine Gulf shoreline, an increasingly scarce feature even among Casey Key’s most exclusive homes. Positioned on one of Florida’s most private barrier islands, home to fewer than 400 residences and free of high-rises or traffic lights, this offering delivers a unique blend of seclusion and accessibility. Located just minutes from the dining, shopping and cultural amenities of Sarasota and the charm of Venice, the property embodies the ultimate coastal lifestyle. This is a rare opportunity to secure a generational waterfront estate with the potential to customize finishes and create a truly bespoke residence in one of Florida’s most coveted coastal enclaves.

2542 Casey Key Road, Nokomis

$2,470,000

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

A custom-built Baron estate of timeless elegance, overlooking a tranquil lake from a quiet cul-de-sac within one of the region’s most coveted guard-gated communities. Located in Oaks Bayside, oak-canopied streets, private bay access, and a peaceful setting define everyday living—just steps from the community’s private day dock on Little Sarasota Bay for kayaking and sunset views. Offering 5,287 square feet of living space, the home features four bedrooms, an office, a study, and 3½ baths, with a floor plan designed for both refined entertaining and comfortable living. Travertine marble and rich hardwood floors extend beneath coffered and tray ceilings, while aquarium windows and impact glass fill the interiors with natural light and frame serene lake views. A gas fireplace anchors the living room, and surround sound enhances the main living areas, all flowing seamlessly to the screened lanai. The chef’s kitchen is appointed with Wolf and Sub-Zero appliances, an oversized island with bar seating, and a walk-through pantry. A casual dining area adjoins the kitchen, while a separate formal dining room accommodates more formal gatherings. A wet bar with a large-capacity wine refrigerator and custom cabinetry adds a sophisticated entertaining element. The primary suite offers a private sitting area and a luxurious bath with separate vanities, individual dressing areas, private water closets, and two walk-in closets with custom built-ins. Three additional bedrooms are thoughtfully positioned for family or guests, along with a spacious office, separate study, and a five-seat home theater. Outdoors, the expansive screened lanai is designed for year-round living, featuring a pool, spa, fountain, covered seating, and a full outdoor kitchen overlooking the lake and lush tropical landscaping. An elegant circular paver drive and a three-car garage with epoxy floors and extensive storage enhance both form and function. Additional highlights include a whole-home vacuum system, solid wood doors, impact windows, a cedar closet, and abundant storage throughout. Located in Flood Zone X for added peace of mind. The Oaks Country Club offers 2 championship 18 hole golf courses, Tennis, pickleball, croquet, bocce, and an abundance of social activities to stay engaged in all the club has to offer. Ideally located near downtown Sarasota, Siesta Key Beach, and renowned cultural destinations, Oaks Bayside offers a rare blend of privacy and convenience. Membership to The Oaks Club is required. A wonderful opportunity to live in one of the finest country clubs in Florida.

449 Webbs Cove, Osprey

$5,299,999

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

Bring your yacht. This is Sarasota waterfront living at its most refined. First time on the market, this custom-built John Cannon estate is perfectly positioned within Southbay Yacht & Racquet Club—one of Sarasota’s most exclusive waterfront communities offering a true private yacht club lifestyle within the neighborhood. With a deep-water marina reserved for residents, accommodating vessels up to 55 feet, and direct access to the Intracoastal Waterway and Gulf of Mexico, this is a setting designed for those who expect seamless access to life on the water. Privately situated on a homesite surrounded by water on two sides, the property offers a rare level of exposure and presence. From your outdoor living spaces, the backdrop is ever-changing—boats moving through the marina, dolphins just beyond your dock, and unobstructed sunsets that define the end of each day. Inside, the residence is a study in craftsmanship and comfort, where rich wood detailing carries throughout—from the staircase to the ceilings in the main living areas and extending into the outdoor spaces—creating a warm, architectural continuity rarely seen. Walls of impact-rated windows and doors bring in natural light while offering peace of mind, while expansive sliders pocket away completely—creating a perfect expression of Florida living with seamless indoor-outdoor flow and unobstructed sunset views across the bay. The kitchen is both striking and highly functional, appointed with Wolf and Miele appliances, dual Sub-Zero refrigerators, a warming drawer, two sinks, and a concealed pantry, all complemented by generous storage and oversized closets throughout the home. A fireplace anchors the main living space, adding warmth and ambiance. Designed for real life as beautifully as it is for entertaining, the home also features a thoughtfully designed mudroom off the garage entry, creating an organized and functional transition into the home. Outdoor living is equally elevated and designed for year-round enjoyment. Electronic roll-down screens allow you to fully enjoy the outdoor kitchen, complete with a propane grill and hood, sink, and composite cabinetry. Just beyond, a propane-fed fire pit creates the perfect setting for evenings by the pool. The separate air-conditioned poolside cabana offers stunning bayfront views and is equipped with its own refrigerator and ice maker—ideal for entertaining or creating a private retreat for guests. The floor plan is thoughtfully designed, offering 4 bedrooms, 4.5 baths, a private office, upstairs lounge, and expansive laundry room—balancing everyday livability with elevated design. For collectors and enthusiasts, the 5-car garage with 9,000 lb lift provides exceptional capacity, while the 110-foot private dock with jet ski lift delivers a level of waterfront utility that is increasingly rare. Southbay Yacht & Racquet Club offers a curated lifestyle with a private marina, clubhouse, fitness center, heated pool, tennis and pickleball courts, and walking trails—all within minutes of Casey Key, where pristine beaches, waterfront dining, and relaxed coastal elegance define the surrounding area. This is a property that stands apart. Compare it to anything else on the market and the value is clear. Priced to sell, with a motivated seller.

313 Lookout Point Drive, Osprey

$4,900,000

4 Beds ⋅ 5 Baths ⋅ N/A SubDv. ⋅ 34275 Zip Code

Discover the ultimate in luxury living in this exquisite John Cannon home, Southwest Florida's most celebrated, award-winning custom home builder for over three decades. This phenomenal residence exudes timeless sophistication and refined coastal living. Set on 98 ft of frontage along the tranquil shores of Dona Bay, this amazing home boasts over 5,700 square feet of thoughtfully designed open-concept living space enhanced by soaring 30-foot ceilings, three fireplaces, a sweeping staircase, polished travertine floors throughout and beautiful Mediterranean architectural interests. Formal and casual living areas unfold seamlessly, opening to multiple balconies, ideal for entertaining and relaxed waterfront living. The magnificent kitchen serves as heart of the home, featuring exotic 2-inch blue Bahia granite counters, a large gas range, three dishwashers, three copper sinks, and wet bar with walk-in 1,000-bottle wine cellar. The main floor also boasts two grand living areas with stunning water views, one of two primary suites, two guest bedrooms, 2 1/2 baths and a butler pantry with laundry facilities. The elevator leads to the second floor, where a dedicated game room, private office and magnificent primary suite serve as a private sanctuary, opening to a romantic terrace overlooking the bay. A closet fit for royalty also hosts a washer and dryer for convenience. The primary bath boasts a full room mirror, two large vanities, walk in shower and Roman tub. Outdoors, the home’s graceful lines lead to an infinity saltwater pool with a sun deck, spa, full bath with air conditioner and resort-style entertainment area, all shaded by 92 palm trees. A bayfront walkway leads to the new Trex dock with a 10,000-pound lift, completing the experience. This is a four-zone house, all units new, a new steel EDCO roof and two septic tanks with new floats and pumps. There is also a central vacuum system for cleaning ease. The extensive list of improvements is available in the attachments. Be sure to watch the video and walk-through floor plan.

419 Bayview Parkway, Nokomis

$6,400,000

5 Beds ⋅ 5 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code

Experience true Florida coastal living in this impeccably maintained Key West–style home on Casey Key, offering the rare and coveted Gulf-to-Bay lifestyle. Thoughtfully designed with high ceilings and a bright, open feel, this residence blends relaxed island charm with modern updates throughout. Step outside to a beautifully landscaped, fenced, and gated backyard—your own private oasis. Enjoy the Pebble Tec resurfaced pool, perfect for entertaining or unwinding after a day on the water. Boaters will love the new composite dock with covered lift, providing effortless access to the bay and Gulf beyond. The dune walkover and 100 feet of private sandy beachfront is perfect for afternoons by the shore and evening sunsets. Adding exceptional flexibility, the separate guest house features one bath and two bedrooms (or one bedroom plus a den)—ideal for guests, extended family, or a home office retreat. This home has been extensively updated for peace of mind, including hurricane shutters, newer HVAC systems, water heaters, well pump, and a whole-house replumb. Every detail reflects pride of ownership and careful maintenance. Whether you’re seeking a full-time residence or a luxurious island escape, this exceptional Casey Key property delivers privacy, comfort, and the ultimate waterfront lifestyle.

3240 Casey Key Road, Nokomis

$4,700,000

4 Beds ⋅ 6 Baths ⋅ Sarabay Acres SubDv. ⋅ 34229 Zip Code

Virtually Staged. PREMIER HIGH-ELEVATION BAYFRONT ESTATE ON 2 PRIVATE ACRES 4 Bedrooms | 5.5 Bathrooms | 6,308 Sq. Ft. | 730 Sarabay Road is a rare opportunity to own two acres of private waterfront property in Osprey. Situated at the end of a long gated drive by a private pond, this expansive estate offers privacy, luxury, and direct boating access to the Gulf through nearby Midnight Pass. Positioned along 100 feet of Little Sarasota Bay frontage, it includes a private dock and 15,000-lb boat lift. Inside, the residence provides over 6,300 square feet of living space, soaring ceilings, walls of windows, and sweeping bay views. Wide-plank oak and floor-to-ceiling hurricane-impact windows frame generous living spaces designed for entertaining and an open-plan gourmet kitchen. The primary suite includes a spa-inspired bath and spacious walk-in closets. Upstairs, three en suite bedrooms feature views over the bay; an additional room offers flexibility as a sitting room or fifth bedroom. Outside, a large travertine terrace, resort-style pool and hot tub, propane fire pit, and broad bayside lawn showcase Sarasota’s brilliant sunsets. A four-car attached garage and air-conditioned, detached three-car garage offer space for car collectors, or for an artist’s studio or home gym. Ideally located between Sarasota and Venice, the home has easy access to Siesta Key and Nokomis beaches as well as to the many cultural attractions of Sarasota’s downtown. Additionally, the home has a documented history of no flooding, water intrusion, or hurricane damage, providing significant peace of mind. This bayfront estate is a unique combination of lush acreage, secure elevation, boating access, and luxury coastal living—a complete waterfront lifestyle.

730 Sarabay Road, Osprey

$3,650,000

4 Beds ⋅ 7 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Nestled within the exclusive gated community of the Oaks Club in Osprey, Florida. This singular estate represents a masterful confluence of architectural refinement and modern luxury, encompassing nearly 7000 ft.² of conditioned living space, the residence has undergone an extraordinary transformation – reflecting an investment exceeding $1.5 million – to achieve a standard of craftsmanship seldom encountered in contemporary homes. The grand foyer reimagined with architectural restraint and elegance, opens to a series of impeccably curated, living spaces defined by scale, light and material integrity. The entire home has been freshly repainted, presenting a pristine, harmonious aesthetic that enhances the interplay of color, texture and light throughout. The kitchen rebuilt from its foundation up is a tour de force of design and function-anchored by bespoke ultra-custom cabinetry, expansive, quartz surfaces, and a suite of professional grade Thermador appliances. These include three wall, ovens a speed-cook microwave, an induction cooktop, dual dishwashers, two wine coolers, a U-line beverage refrigerator, and an impressive new side by side Thermador refrigerator and freezer. Every culinary and social experience is elevated by thoughtful details such as Newport Brass fixtures, elegant chandeliers, and an exceptional walk-in pantry that unite beauty and practical design. The primary suite embodies serene granuer, featuring a newly constructed bath with custom cabinetry, a sculptural freestanding tub, and dual shower-all finished in large format, porcelain tile. A remarkable walk-in closet includes a concealed storage and safe room, melding security with sophistication. Two additional bedroom suites have been fully redesigned with its own private bath, while a refined powder room enriches the main entry corridor. Throughout the home, state- of-the-art technology complements the elegant aesthetic, a newly installed security system with outdoor surveillance cameras, ensures peace of mind, while a Sonos sound system, integrates premium audio, seamlessly across living areas for both entertainment and ambience. Additional appointments include new hardwood flooring, freshly refinished and painted garage spaces with an epoxy-coated floor, and a large air-conditioned storage room with supplementary washer, dryer hook ups. The outdoor domain has been equally vitalized, showcasing, a newly remodeled pool, upgraded mechanical systems, and beautifully landscaped grounds that frame the home with natural grace and meticulous attention to detail. Residing within the Oaks Club, homeowners enjoy the exclusivity of one of Sarasota County’s, most distinguished country club communities renowned for its championship golf courses, fine dining, tennis and social amenities. This one-of-a-kind Eagle Watch Lane estate stands as a testament to discerning design, meticulous, stewardship, and enduring architectural grace.

691 Eagle Watch Lane, Osprey

$9,000,000

6 Beds ⋅ 7 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code

WELCOME TO ONE OF THE FEW BRAND-NEW GULF FRONT HOMES FOR SALE ON THE WEST CENTRAL COAST OF FLORIDA. A rare opportunity, where cutting-edge design meets wide Gulf vistas. Nestled on the prestigious barrier island of Casey Key, this newly constructed Modern Coastal estate exemplifies modern beachfront living. Positioned directly on the sand with sweeping Gulf views, this striking residence offers elevated living space, showcasing the pinnacle of craftsmanship and architectural innovation. Built with block construction, pilings, impact-rated windows and doors, and a four-stop elevator, every detail of this home has been thoughtfully curated for style, function, and resilience. Inside, soaring 24-foot ceilings welcome you into the grand foyer and great room, anchored by a dramatic floating staircase and a 24-foot feature fireplace wall. With en-suite bedrooms, state-of-the-art home theater, lounge, bar, and a wine wall, this home offers both grand entertaining and serene retreat. The chef’s kitchen is a design showpiece, featuring European cabinetry, dual waterfall-edge islands clad in book-matched 3cm quartz, and premium Sub-Zero & Wolf appliances. Dual laundry rooms, breakfast nook, and custom built-in vanities provide elevated everyday living. The primary suite is a personal sanctuary, complete with a spa-like bathroom featuring a 71-inch freestanding tub, dual rainfall showers, a makeup vanity, and a large walk-in closet. Every bathroom throughout the home is appointed with bespoke cabinetry, quartz surfaces, and backlit mirrors. Designed to impress from every angle, the home is finished with smooth stucco, level 5 drywall, hardwood floors, imported tile, and integrated LED tray ceilings. A sleek rooftop terrace crowns the home, offering panoramic views of the Gulf and beyond. Step outside to your personal resort: an expansive terrace with an oceanfront pool, floating spa, sun decks, outdoor fireplace, and fully equipped kitchen. Lush, tropical landscaping, Zoysia grass, and a concrete drive with turf inlays complete the impeccable exterior design. Sleek metal railings accentuate balconies and the rooftop for a modern edge. Set on a half-acre of prime waterfront. This is coastal modern luxury at its pinnacle—a rare opportunity to own a brand-new, Gulf-front estate on one of Sarasota’s most desirable stretches of sand.

4005 Casey Key Road, Nokomis

$2,625,000

4 Beds ⋅ 7 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code

Welcome to your dream home, a sanctuary of elegance and comfort nestled on an exclusive, private street with only nine residences and no neighbors across the way—just the tranquility of a natural preserve. This remarkable property in The Oaks Clubside, with 4 bedrooms, 5 full bathrooms, and 2 half baths, boasts impact windows and doors throughout, providing peace of mind and a quiet, secure environment. Step inside to discover an open floor plan adorned with a blend of rich wood and luxurious travertine floors. Each of the large bedrooms is an en suite retreat, offering privacy and comfort for residents and guests alike. On the first floor you will find a huge master suite, with his-and-her closets, and a luxurious master bathroom that has two separate vanities, a walk-in shower and soaking tub. The two additional bedrooms are generously sized. The open kitchen features cherry wood cabinets, a granite island and high end stainless steel appliances. The breakfast nook is flooded with natural light and offers a lovely view over the pool. The second story has a fourth en-suite bedroom, and balcony overlooking the golf course and lake. And, for those who love to entertain, the game and media room is designed for fun gatherings of friends. The heart of the home extends outdoors, where you will find an impressive outdoor kitchen area perfect for grilling and dining alfresco. Enjoy a beautiful, long view of the Heron #14 and the serene lake beyond—a panoramic scene that will take your breath away every day. This home is loaded with thoughtful additions, including three new exterior ceiling fans for comfort on warm days, custom office closet shelving and a secure dog run fence for your furry friends. The garage boasts a durable epoxy floor and hurricane-rated doors. Additional upgrades abound with 4 new AC units with UV lights for optimal air quality, a new roof, two-stage pool pump and new irrigation pump, new tankless Navian water heater to name a few. You absolutely must see this home to appreciate all it has to offer. Membership in The Oaks Club, Sarasota’s premier golf and country club is required with home ownership.

478 Oriskany Court, Osprey

$4,150,000

5 Beds ⋅ 7 Baths ⋅ Blackburn Ridge SubDv. ⋅ 34275 Zip Code

Discover an extraordinary, bayfront contemporary masterpiece in the exclusive Blackburn Estates, a gated enclave of serenity. This five-bedroom, seven-bath residence redefines luxury, with a harmonious blend of sleek modern design and timeless craftsmanship. Among this home's many unique features is an indoor basketball half-court, above the three-car garage! Go through the bespoke solid walnut pivot door into a world of elegance, where panoramic bay views captivate instantly. The great room exudes warmth and sophistication, with its soaring wood-paneled ceilings, custom recessed and pendant lighting, and polished charcoal-stained slab floors. A striking 10-foot ledgestone fireplace anchors the space, seamlessly connecting to an expansive outdoor oasis via pocketed sliding glass doors. Outside, a disappearing-edge pool with ice deck steppingstones and sun shelf, complements a vast patio and outdoor kitchen, ideal for entertaining or tranquil relaxation. This architectural gem effortlessly combines low maintenance luxury with family-friendly functionality, at the end of a peaceful cul-de-sac. A rare opportunity to own a home that is a sanctuary and a statement.

4907 Topsail Drive, Nokomis

$2,925,000

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

Sited at the end of a quiet cul-de-sac behind the gates of the prestigious Oaks Clubside in Osprey, Florida, this stately traditional custom estate offers refined living in one of Sarasota County’s most exclusive communities. Perfectly positioned on over three-quarters of an acre, the residence boasts serene preserve and fairway views, capturing the essence of Florida luxury living. Inside, discover graciously sized rooms, soaring ceilings, and abundant natural light that fills every space. The formal living room with gas fireplace and the formal dining room provide elegant spaces for entertaining. The open-concept kitchen and family room are the heart of the home, ideal for casual gatherings and everyday comfort. A large kitchen offers a generous walk-in pantry, plentiful storage, and a seamless flow into the family room and outdoor spaces. The primary suite is located on the main floor, offering a tranquil retreat with a spa-like bathroom, separate dressing room, and expansive walk-in closet. An office with fireplace is also on the main level, perfect for work-from-home privacy. Upstairs, two additional bedrooms and a bonus room provide a private haven for guests or multi-generational living. Step outside to the screened and covered outdoor living area, where a summer kitchen, cabana with full bath, and lush landscaping invite indoor-outdoor living year-round. It’s an entertainer’s dream, ideal for both intimate gatherings and grand events. Key features include wind-rated impact windows, new tile roof to be installed with a transferable 20-year workmanship warranty, $800,000+ in updates under current ownership, and situated on an oversized lot with ultimate privacy. As part of The Oaks Club, enjoy world-class amenities including two championship golf courses, 12 Har-Tru tennis courts, pickleball, croquet, a state-of-the-art WellFit Center, and exceptional dining at The Oaks Room, The Overlook, and The Tavern. This is more than a home—it's a lifestyle. Experience the timeless elegance, thoughtful design, and unmatched amenities of The Oaks Club in this remarkable estate.

550 Dove Pointe, Osprey

$2,315,000

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

Premier Waterfront Opportunity in The Oaks Bayside This grand estate home, perfectly positioned on a rarely available direct waterfront lot in the exclusive, gated Oaks Bayside community, offers sweeping views of Little Sarasota Bay and exceptional potential. With its expansive floor plan across three levels, soaring ceilings, and dramatic architectural features, this residence was built to impress—and now invites a new owner to make it their own. The ground floor has been thoughtfully prepared for renovation, providing a blank canvas to bring your vision to life. Whether you imagine a guest or in-law suite, a luxury garage with a gaming lounge, a showcase for your fishing gear, or a green room for potting plants—the possibilities are endless. A private dock awaits your custom design, offering direct access to the open bay and Gulf of Mexico. Just steps from the home, the community dock—exclusively for Oaks Bayside residents—adds even more coastal charm. Fish, launch a kayak, relax and watch the sunset, or gather with neighbors in this serene waterfront setting. Ownership includes mandatory membership in The Oaks Club, unlocking an array of world-class amenities. Set across more than 1,000 acres, the club features two private 18-hole championship golf courses, 14 Har-Tru tennis courts, a croquet lawn, a junior Olympic swimming pool, state-of-the-art fitness center, and a stunning 34,000-square-foot Georgian-style clubhouse. A guest lodge and vibrant year-round social calendar complete this private country club experience. You're not just creating a home—you're curating a luxury lifestyle in one of Florida’s most prestigious coastal communities. This exceptional property is ready for your private tour at your convenience.

112 Osprey Point Drive, Osprey

$1,900,000

5 Beds ⋅ 7 Baths ⋅ Oaks The SubDv. ⋅ 34229 Zip Code

Introducing The Grand Estate at The Oaks Bayside—a true masterpiece of refined living within one of Sarasota’s most prestigious gated communities. Surrounded by majestic oak trees and lush tropical landscaping, this extraordinary residence offers the perfect blend of elegance, comfort, and privacy. A brand-new roof (2024) crowns this sprawling estate, while a pavered circular driveway leads to a spacious 3-car side-load garage. Stately columns welcome you to the grand double-door entry, where you’ll step inside to find gleaming marble floors, soaring ceilings, and plantation shutters that set the stage for timeless sophistication. The thoughtfully designed floor plan includes a private office with built-ins and French doors, and a flexible open space with a dramatic backlit tray ceiling—ideal for a formal dining room, music room, or library. The formal living room features a stunning picture window that brings the outdoors in, along with a cozy fireplace and direct access to the luxurious pool area. The chef’s kitchen is a true showstopper, complete with an aquarium window breakfast nook, expansive breakfast bar, dual sinks, center island, double wall ovens, and a butler’s pantry. It opens seamlessly into the family room, where sliding glass doors, a wood-burning fireplace, wet bar, and built-in desk create a warm and inviting space for everyday living and entertaining. The primary suite is a tranquil retreat with a sunlit sitting area, private access to the pool, and a spa-inspired en suite bath with a walk-in shower and soaking tub that overlook your private tropical paradise. Step outside to your own resort-style oasis, where a sparkling pool, separate spa, travertine deck, and covered patio offer the ultimate in outdoor living. With over 6,000 square feet of living space, this estate features 5 bedrooms, 5 full bathrooms, and 2 half baths, along with two newer A/C systems (2023). As a resident of The Oaks, you’ll have access to The Oaks Club’s world-class amenities, including two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center, and fine dining. Ideally located near top-rated Pine View School, Historic Spanish Point, Casey Key, and Oscar Scherer State Park, this home offers both tranquility and convenience. Don’t miss your chance to own this exceptional estate—schedule your private tour today and experience the luxury of life at The Oaks Bayside.

340 Osprey Point Dr, Osprey

$2,700,000

6 Beds ⋅ 7 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Multigenerational living behind the gates of The Oaks Golf & Country Club. Set on a rare double lot at the end of a quiet cul-de-sac, this exceptional home is perfectly positioned on the 1st hole of the Heron Course, capturing sweeping golf course and clubhouse views—just minutes from Siesta Beach and Casey Key. The main residence offers 4,700+ square feet, complemented by a private 1,500+ square foot guest house—ideal for extended family or long-term guests. Outdoor living is elevated with a pool and spa, outdoor kitchen, private guest laundry, and some of the most captivating views in the community. At The Oaks, coastal sophistication unfolds across 36 championship fairways, tennis and pickleball courts, with endless opportunities for recreation, dining, and connection. Membership required.

236 Saint James Park, Osprey

$1,650,000

5 Beds ⋅ 7 Baths ⋅ Venetian Golf And River Club SubDv. ⋅ 34275 Zip Code

This stunning 5,252 square-foot estate is a true masterpiece, offering the perfect balance of luxury, privacy, and an exceptional lifestyle. The home features five spacious bedrooms, five and a half beautifully appointed bathrooms, and every detail is meticulously crafted for both comfort and elegance. Upon entry, you’re immediately struck by the soaring ceilings and an open, airy design that flows seamlessly from room to room. The expansive living area is bright and welcoming, with large windows framing gorgeous views of the surrounding landscape. The chef’s kitchen is an entertainer's dream, featuring top-tier appliances, an oversized island, and custom cabinetry. It opens up to the formal dining room, perfect for hosting intimate dinners or grand celebrations. The master suite is a sanctuary in itself, with a private sitting area, an inspired bathroom with a soaking tub, walk-in shower, dual vanities, and a spacious walk-in closet. Each of the other four bedrooms is generously sized and access to bathroom, offering the ultimate privacy and comfort for family and guests. A standout feature of the home is the self-contained mother-in-law suite, with its full bathroom—ideal for guests, family. Step outside into the expansive backyard, where you'll find a resort-style pool surrounded by lush landscaping, providing a private oasis. The pool area includes cascading waterfalls, an integrated spa, and ample space for lounging or entertaining. An outdoor kitchen and dining area make this the perfect spot for summer barbecues and pool parties. For entertainment, in the second floor there is a room ready to be set for a theater room. Whether you're hosting movie nights or enjoying the big game with friends, this room offers the ultimate cinematic experience. Beyond the property, the community offers an abundance of luxurious amenities to suit every interest. Residents can enjoy access to a world-class golf course, where rolling fairways and pristine greens await. For those who prefer sports, there are tennis and basketball courts, offering plenty of opportunities for outdoor recreation. The gym is fully equipped with the latest fitness equipment, ensuring you have everything you need to stay in top shape. For those seeking relaxation, the community building is the perfect place to unwind, whether you're hosting an event, attending a social gathering, or simply enjoying the peaceful ambiance. And for nature lovers, the boardwalk through nature is a serene path that winds through the lush surroundings, offering a quiet retreat where you can enjoy walks or jogs with stunning views of the natural landscape. This estate offers the ultimate blend of luxury living, world-class amenities, and unparalleled outdoor spaces. With every detail thoughtfully designed, this is a home where every day feels like a vacation, and no matter what your interests are, you’ll find everything you need right at your doorstep.

273 Portofino Drive, North Venice

$1,600,000

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

Situated on a double lot behind the secure gates of The Oaks, this two story 5 bedroom home, with 7.5 bathrooms, boasts fantastic potential and excellent bones. The only thing it needs is for you to put your personal touch on it and make it your own. As you pull up to this home, using the front circular driveway, or the back driveway with access to the 4 CAR GARAGE, you will immediately be taken with its classic lines. With its spacious layout and thoughtful design, this property is a hidden gem for those who love to entertain. With so much space, and every bedroom having its own en-suite bathroom, there is room for your loved ones and to host visiting guests, preserving privacy for all. Downstairs you will find a formal living room and an expansive family room with fireplace, built-in shelving, ceiling fan and numerous doors filled with natural light. The large open kitchen has everything the home chef could possibly need to create incredible edibles. Casual meals can be taken in the adjoining breakfast nook, or you can serve a formal feast in the large dining room with built-in cabinetry and a wet bar just outside. The master suite is huge featuring a dedicated sitting area, and his-and-hers master bathrooms. Completing the first floor is a guest bedroom a large office or library with built-ins and a powder room. Upstairs you will find 3 more en-suite bedrooms. One of which is off the back stairway and would make a great guest suite or private room for live-in help. Outdoors, the landscaped double lots, surrounded by a low wall, provides a tropical sanctuary. Here you will find an enormous, screened lanai, that is an entertainer's paradise. A sparkling pool, spa, expansive patio, and an outdoor kitchen set the stage for al fresco living at its finest. Whether enjoying serene sunsets or hosting vibrant soirées, this home will help you create unforgettable memories with friends and family. Membership in The Oaks 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.

916 Macewen Drive, Osprey

$4,000,000

4 Beds ⋅ 6 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code

Auction Property. AUCTION BIDDING OPEN: Bidding ends 6/26. Previously listed at $6.445M. Current high bid $4M. An architectural masterpiece awaits on Casey Key, where traditional Gulf Coast charm meets bold contemporary design in this magnificent 2018-built waterfront estate. Spanning 6,335 square feet of refined living space, the residence captivates with soaring ceilings and dramatic walls of glass framing endless Gulf of Mexico panoramas and spectacular sunset vistas. Meticulously crafted for seamless indoor-outdoor living, the open-concept interior flows effortlessly to expansive terraces and an infinity-edge pool overlooking tranquil waters. The gourmet kitchen showcases premium Italian Cucina cabinetry, sophisticated Dekton countertops, and professional-grade Miele and Bosch appliances. Four luxurious bedroom suites provide sumptuous accommodations, while a state-of-the-art media room, elegant gas fireplace, and comprehensive Crestron home automation system elevate the living experience. This extraordinary property represents the pinnacle of Gulf Coast luxury, offering discerning buyers an unparalleled opportunity to embrace the coveted Casey Key lifestyle in absolute comfort and style.

3909 Casey Key Road, Nokomis

$4,401,065

5 Beds ⋅ 9 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code

Auction Property. LUXURY REAL ESTATE AUCTION on-site on Friday, February 27, 2026, at 1:00 PM. Previews begin on Saturday, February 7th, and will run every Saturday and Sunday from 1:00 to 4:00 PM until the auction. Private appointments are available; please call for details. Designed by renowned architect George Merlin and built in 2006 by Christner Brothers to hurricane-resistant building code, this home rests securely on concrete-driven pilings and exudes unparalleled quality. Watch the sunrise over the Intracoastal Waterway from the deepwater boat dock and lift. Spend the afternoons on your private beach along the sandy shore of the gulf where spectacular sunsets are almost guaranteed. Inside nearly 8,000 square feet, five bedrooms with en suites, nine baths, formal living, family and sitting rooms, dual private offices, den and a theater room provide seemingly endless enjoyment. Crown molding, trayed ceilings, travertine flooring, three fireplaces and Yoder Brothers custom cabinetry exude elegant touches throughout. An elevated lagoon-style swimming pool is great for a cool dip or relax in the heated spa and outdoor fireplace on a chilly evening. The gourmet kitchen is large enough to host an impressive dinner party and gather with family and friends. Casey Key is a place like no other, where residential homes line the shores, absent of commercial building and high-rise condominiums. Development is restricted to single-family homes, yet all conveniences of shopping and restaurants are minutes away. Private and commercial air travel are easily accessible. Sports and cultural entertainment enthusiasts will find golf, tennis, theaters, music and more, just a few miles away in nearby Venice and Sarasota. There’s something for everyone in this gulf to bay resort-style home.

1304 Casey Key Road, Nokomis

$3,498,000

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

Auction Property. AUCTION – Seller offering property via online auction. Now Selling at or Above the Published Reserve Bid Price of $2.5M! Previously listed for $5.7M. Bid online beginning Monday, April 28th. weekend begins Friday, April 25th to view this fully furnished home in the Enchanted Isles community along the shores of Roberts Bay, just minutes from historic downtown Venice. This John Cannon-built home offers 4 ensuite bedrooms, 5.5 bathrooms, and refined craftsmanship throughout. Features include a grand foyer with travertine floors and iron staircase, chef’s kitchen featuring professional grade appliances such as Sub-Zero refrigerator, Wolf dual-fuel range, dual dishwashers, wet bar, wine room, and expansive living spaces filled with natural light. The primary suite boasts a fitness room, spa-like bath, water views, and private courtyard, while a separate guest suite with private entry and kitchenette provides additional privacy. Upstairs includes two ensuite bedrooms, a powder bath, billiards room, and family room with terrace overlooking the bay and Intracoastal. Outdoor living features a saltwater pool and spa, summer kitchen, fireplace, and a 10,000 lb. boat lift with dock—just five minutes to the Gulf with no bridges. Close to dining, shopping, golf, top medical care, cultural attractions, and world-class beaches. Contact agent or Interluxe.com for full terms and conditions of the sale and schedule appointment to preview the home.

457 Anchorage Drive, Nokomis

$3,525,000

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

This stunning waterfront residence in Southbay Yacht and Racquet Club is a gem on Florida’s Gulf Coast where boats are accommodated in a deep-water marina for low fees. Boasting over 135 feet of water frontage and surrounded by lush tropical landscaping and majestic Royal Palms. Its refined curb appeal sets it apart as a one-of-a-kind property. The custom John Cannon home features a grand double door entry that opens to breathtaking wide open bay views. Inside, the home showcases high-end finishes and upgrades, including impressive, vaulted ceilings reaching up to 21 feet. You'll find abundant crown molding, elaborate tray ceilings, and exquisite wall finishes adorned with artfully painted faux designs and plantation shutters throughout. The home is designed for entertaining, with a full bar and wine room for guests, as well as an upper-level wet bar. The chef's kitchen is a culinary dream, featuring a spacious granite island, a gas cooktop with a pot filler, and views overlooking the pool, patio and bay. An upper-level bonus room offers versatile space for play, music, movies or exercise, all while enjoying some of the best views in the house. The main level primary suite is a serene retreat with a sitting area, two large closets and a luxurious bath that includes a garden shower, large tub, dual sinks, and a separate toilet and bidet. The expansive outdoor living spaces, including main level and upper terraces, are ideal for enjoying sunsets and observing local wildlife such as ospreys, dolphins, manatees and a parade of boats. Private dock for sunset viewing and fishing. Ideally between Sarasota and Venice, this residence is just minutes from the pristine sands of Siesta Key and Nokomis Beach. Convenience abounds with nearby shopping, dining the Legacy Trail, private and commercial airports, and top-rated schools, including the renowned Pine View School. This exquisite home embodies the essence of Florida living. Southbay Yacht & Racquet Club lives up to its name with a newly renovated community clubhouse, geothermal pool, gym overlooking the marina, banquet rooms, three tennis courts, four pickleball courts, a bocce ball court, two shuffleboards, basketball, kayak storage area, a waterfront park, 20 acres of common grounds and miles of trails. Ideally in between culturally rich Sarasota and charming Venice, minutes to beaches, Legacy Trail, No. 1 rated Pine View School, shopping, waterfront restaurants and Oscar Scherer State Park. Walk to your boat or take your golf cart around the neighborhood. For those who seek an exceptional waterfront life, nothing compares.

275 Lookout Point Drive, Osprey

$1,650,000

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

Florida living at its finest! You'll find this lovely home tucked away on a cul-de-sac in the luxurious community known as The Oaks. This amazing custom-built home features 5 bedrooms, 5.5 bathrooms and 5,399 sq. ft. of fabulous living space, combining comfort with elegance! Upon entering you are greeted by the formal living room with high ceilings, crown molding, large sliding glass doors and arched windows. The gourmet kitchen is a chefs dream with plenty of space to work with, double refrigerators, a breakfast bar and island, open to the family room. The dining room is ideally located off of the kitchen and living room and features triple tray ceilings and a built-in bar ~ perfect for entertaining! Sliding glass doors from the living room, family and master bedroom lead out to a spacious covered lanai, pool/spa and outdoor kitchen. This home is situated on a large lot with golf course and pond views, providing a peaceful setting. Updates include a new roof (2021), fresh interior paint, landscaping and more! Tenant occupied with current lease agreement until 08/16/2025. Nestled amongst luxurious homes, mature landscape and streets lined with canopying oak trees, the Oaks is a gated community with two golf courses, racquet sports, wellness, fitness, dining and so much more. Membership is required. Close to everything Sarasota County has to offer, including beaches, parks and top-ranking Pine View School. Schedule a tour today.

676 Eagle Watch Lane, Osprey

$5,450,000

5 Beds ⋅ 7 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code

Experience unparalleled luxury on the coveted south end of Casey Key, where this custom Gulf-front estate offers 90 feet of pristine beach frontage, endless views of the turquoise Gulf waters, and the most walkable wide beach on the Key. Built with timeless craftsmanship, the residence spans over 12,000 square feet in total, featuring five bedrooms, six-and-a-half baths, and two spectacular primary suites with sunset balconies, spa-inspired baths, and expansive custom closets. Designed for both elegance and comfort, interiors include a soaring two-story living room, gourmet chef’s kitchen with Wolf, Sub-Zero and Cove appliances, formal dining with Venetian plaster, home theater, gym, and private office with water views. The technology package including automated lighting, programmable blinds, and secure hardwired internet. Outdoors, a Gulf-front saltwater pool and spa, summer kitchen, and private dune walkover create the ultimate coastal retreat. Additional luxuries include a 1,000-gallon propane tank which runs the whole home generator, elevator, R/O water filtration system, and impact-rated windows and doors. Perfectly situated minutes from boating, marinas, fine dining, and the cultural attractions of Sarasota and Venice, this exceptional Casey Key estate is move-in ready and awaits as your exclusive beachfront sanctuary.

507 Casey Key Road, Nokomis

$9,196,000

5 Beds ⋅ 7 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code

Unveiling a once-in-a-lifetime opportunity to own an unparalleled slice of coastal luxury. Welcome to Pretiola Sands Estate, a secluded and gated haven sprawled across 1.4 acres of lush grounds, boasting an impressive 200 feet of private shoreline on both the Gulf of Mexico and the Intracoastal Waterway. Experience the awe-inspiring vistas of the Gulf and Bay from every vantage point of this meticulously designed family compound. The main residence is built like a fortress on 91 pilings. It is separate yet connected to guest quarters and steps away is a Gulf-front cabana, creating an idyllic retreat for family gatherings and entertaining guests. The essence of resort-style living comes to life with a grand screened recreation area featuring a sparkling pool, a 5-hole putting green, and numerous sitting and dining areas calling you to unwind and savor the tranquil beauty of the Intracoastal Waterway. And for the avid boater, a private dock with a covered boat lift awaits for effortless maritime adventures. Step inside to experience unparalleled luxury and craftsmanship. A beautiful foyer adorned with a granite waterfall leads to the formal dining room and cozy sitting area, both offering Gulf views. The expansive family room, adorned with a charming fireplace, invites you to bask in the serenity of bayfront living. The heart of the home, a chef-inspired kitchen, features Neff international design cabinetry, top-of-the-line appliances, and a breakfast nook bathed in natural light. Adjacent, a wet bar with icemaker and wine chiller ensures seamless entertaining, while the bayside lanai beckons with a gas fireplace and built-in grill for alfresco dining. Retreat to the luxurious Gulf-side primary suite conveniently located on the first level with a massive closet and bayside bath. boasting panoramic Gulf views, a bay-side bath with custom dressing room, and heated floors for ultimate comfort. Meanwhile, guests will delight in the separate guest quarters offering privacy, bamboo flooring, a kitchenette, and a full bath. Upstairs, there are four additional bedrooms, a movie theater, nursery, and convenient laundry facilities. The ground level presents a spacious 3-car garage with ample storage and convenient elevator access to all levels. But the epitome of island living awaits at the charming beach cabana, where a living room, outdoor shower, and dressing room await. Hurricane-rated glass sliding doors seamlessly blend indoor and outdoor living, and Wi-Fi ensures comfort and convenience. The home, itself, sustained no storm damage. The photo of the beach cabana is pre-storm. It has been restored and upgraded.

1776 Casey Key Road, Nokomis

$2,400,000

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

WELCOME HOME - NO STORM DAMAGE AT THIS PROPERTY (ELEVATION / OVERALL BUILD) ~ THE OAKS COUNTRY CLUB - SARASOTA, FL. THIS HOME @ #425, BOASTS BEAUTIFUL GOLF COURSE AND SELECT WATER VIEWS THROUGHOUT. A 27,000 SF +/- PRIVATE LOT. ONE CAN LOOK DIRECTLY AT THE PAR 3 - 4TH HOLE (THE OAKS HERON COURSE). MATURE STUNNING LANDSCAPING SURROUNDS THE PROPERTY. THE HOUSE OFFERS A TOTAL OF 5,100 SQUARE FEET OF RANCH-STYLE LIVING, 5 BEDROOMS, 5 BATHROOMS WITH AN ADDITIONAL 1/2 BATHROOM. A SEPARATE GUEST SUITE WITH LIVING AREA AND SEPARATE ENTRANCE IS INCLUDED, PERFECT FOR VISITORS, GUESTS, OR A SECOND OFFICE SUITE. SOME OF THE UPDATED FEATURES INCLUDE BUT ARE NOT LIMITED TO AN OPEN FLOOR PLAN, UPDATED GOURMET KITCHEN, GAS FIREPLACE (MASTER / LIVING), ALL EN SUITE BEDROOMS, SLIDING POCKET DOORS, COFFEE BAR, SOAKER TUB, MARBLE FLOORS, GLASS SHOWERS, GRANITE COUNTERS, OUTDOOR BAR AND KITCHEN, SPACIOUS MASTER SUITE, UPSTAIRS BONUS ROOM WITH BATH AND TERRACE OVERLOOKING THE GOLF COURSE AND WATER. THERE IS ALSO A SEPARATE PRIVATE OFFICE/DEN AREA, AN EXPANSIVE POOL AREA - COVERED AND OPEN, AND RECENTLY UPDATED HURRICANE WINDOWS AND DOORS, INCLUDING A STUNNING CUSTOM-MADE CAST IRON FRONT ENTRANCE FLOOR-TO-CEILING DOOR. THE ROOF SYSTEM HAS BEEN UPDATED, THREE NEW A/C SYSTEMS, NEW POOL PUMP, WATER BOOSTER FOR EVEN PRESSURE THROUGHOUT, MEDIA ROOM WITH 85” SMART TV WITH SONOS, NEW SAMSUNG WASHER / DRYER SYSTEM, 240 VOLT CAR CHARGING, UPDATED OUTDOOR KITCHEN WITH FRIDGE, OUTDOOR LIGHTING, NEW POOL CAGE, WATER SOFTENING SYSTEM, DOUGLAS BLINDS WITH REMOTE, AND A NEW POOL HEATER WITH A PHONE APP; THE PROPERTY IS VERY CLOSE TO THE CLUBHOUSE AND ALL THE FIRST-CLASS AMENITIES, INCLUDING GOLF, TENNIS, FITNESS, RESTAURANTS, POOL, COMMON AREAS, CROQUET, AND SOCIAL EVENTS. THE OWNER HAS UPDATED ALL THE HOME AND PROPERTY INSPECTIONS TO INCLUDE BUT NOT LIMITED TO 4-POINT AND WIND MITIGATION REPORTS FOR INSURANCE. THE OAKS CLUB HAS BEEN AWARDED THE PLATINUM CLUB OF AMERICA DESIGNATION. OUTSIDE THE PRIVATE GATES, THERE IS ACCESS TO ALL THAT THE SARASOTA AREA HAS TO DELIVER, INCLUDING SIESTA KEY BEACH, DOWNTOWN ARTS, UTC SHOPPING AREA, LIDO BEACH, NOKOMIS BEACH, AND THE SARASOTA HOSPITAL SYSTEM. THERE ARE ALSO LEADING PUBLIC AND OTHER SCHOOL OPTIONS, SUCH AS PINE VIEW SCHOOL (#1 IN FLORIDA / #18 NATIONALLY) AND OUT OF DOOR ACADEMY. PLEASE REFER TO THE UPDATED VIRTUAL PROPERTY TOUR AND HD PHOTOS. WE LOOK FORWARD TO YOUR VISIT! NOTE: THE OAKS CLUB MEMBERSHIP IS REQUIRED - PLEASE REFER TO CLUB DOCUMENTS FOR DETAILS.

425 E Macewen Drive, Osprey

$8,631,000

Acreage & Unrec SubDv. ⋅ 34275 Zip Code

Escape Resort and Marina is a rare opportunity to purchase a profitable boutique resort that exudes a tropical sophistication that is rarely found. This tropical oasis is comprised of seven buildings with enormous suites that have very recently been thoughtfully reconstructed. This Casey Key resort is located on over one acre of lushly landscaped waterfront paradise that is only steps from the pristine sand and welcoming waves of the Gulf of Mexico and located near delicious waterfront restaurants and world class shopping. The lushly landscaped paver walkways lead to 14 expansive rooms each open onto the outdoor patios & balconies with many rooms having a waterfront view. All recently reconstructed rooms have been extensively renovated with features that include all new roofs, electrical and plumbing, HVAC and mechanical systems, new drywall with wall to ceiling finishes, new flooring throughout, new category 4 windows and doors and light fixtures. Each room offers new full-sized kitchens with high quality cabinetry, countertops and stainless-steel appliances, flat top stoves, microwaves, and dishwashers. Rooms range from 2 bedroom with den/3 baths to large one-bedroom suites. Onsite, guests enjoy a large pool and sundeck, hip, fun common areas including a beautiful waterfront clubhouse with full kitchen, a waterfront amphitheater with firepit, BBQ grilling areas, bicycle and kayak rentals, and workout facilities. The enormous modern rooms are styled to perfection and adorned with flat-screen TV’s, free Wi-Fi, and high-end furnishings. The attention to detail is awe inspiring as represented by the high guest review ratings and return clientele. This is a very profitable resort that has consistently experienced year after year increases in occupancy/ADR with very strong projections for 2024. The recently reconstructed 15 dock marina provides an additional generous steady stream of income. The marina is located on sailboat water and can accommodate boats up to 50 feet, contains up to 50-amp electric, water, nine 20-foot finger pipers as well as one covered boat slip with lift. Escape Resort is truly a premier year-round waterfront resort and marina. The demand for waterfront island Vacation Rentals is extraordinary and this resort stays consistently full. Escape Resort and Marina is located on coveted Casey Key Island nestled just south of world-renowned Siesta Key and quaint Venice Island and is a short drive into Sarasota, the cultural capital of the south. This island has very little accommodation competition and rooms can be rented nightly, weekly, or monthly. This Florida island beach lifestyle includes awe-inspiring sunsets and guests enjoy this amazing experience. With all of the upgrades recently completed, this is a turn-key investment for any entrepreneur or experienced hotelier that will bring tremendous cash flow while enjoying a true Island beach experience. Please DO NOT walk the property without permission and DO NOT disturb Seller or Employees.

212 Casey Key Road, Nokomis

$3,915,000

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

**EXQUISITELY DESIGNED ESTATE BOASTS MODERN & CONTEMPORARY ELEGANCE** This FULLY UPDATED Residence features a MAIN HOUSE with 3Beds/4.5Baths plus GUEST HOUSE (1Bed/1Bath, Kitchen/Laundry, Living area) and is situated on an Oversized, Private and Serene DOUBLE LOT in the SECURE, OAKS BAYSIDE Country Club Neighborhood on Little Sarasota Bay. Finishes of the highest quality abound and include Custom Iron entry and interior doors, Italian Murano sconces and chandeliers, architectural recessed lighting, Marble and Porcelain Flooring, Iron and Glass custom Wine Cellar, Glass enclosed “Spirits” Showcase, luxury appointments and fixtures throughout and is a MUST SEE! The GOURMET KITCHEN is impressively equipped with top brands including SUBZERO, WOLF, 2 ASKO dishwashers, “Waterstone” gantry faucets, work-station sinks, custom range hood, MIELE Coffee Station, etc. In total, there are 2 kitchens and 3 laundry facilities. The Stunning OUTDOOR ENTERTAINING area features a spacious screened lanai with Gorgeous, Saltwater, Heated, Pebbletec 64ft Lap Pool and Spa, Marble deck, OUTDOOR KITCHEN with Twin Eagles Grill, 2 refrigerators, covered gathering area with fireplace, air-conditioned Pool Bath with Aromatherapy Steam Shower (New in 2024), storage room and Additional Open Air Patio with FIRE PIT. Extensive Home Automation (Control4: sound, lighting, etc.) and Mechanical system installations were thoughtfully executed and include a Generator, water treatment and purification systems, robust Wi-Fi throughout, Vivent video monitored security system, Air-Conditioned Garage with EV charging, resin coated floors and utility sink, etc. Impressive grounds with new landscaping, hardscaping & lighting. Newer ROOF, HVAC, Hurricane Impact Rated Windows and Doors. THE OAKS-BAYSIDE is a distinguished, 24hr Guarded, 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. **ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO**

601 Fernwalk Lane, Osprey

$1,150,000

Nokomis Heights SubDv. ⋅ 34275 Zip Code

A unique 8-plex property in Sarasota County can be your next savvy investment opportunity! 5 of the 8 units have been partially updated (paint & some new appliances) with rents hovering at or above market rate. The other three units are ready for a rent bump from the next owner. Monthly gross income of $7,610! New exterior paint for both buildings and new exterior lights above each door. Two separate properties and buildings, each sharing a parking lot. Property is on well and septic, and both systems have been serviced in the past 6 months. Septic tank replaced 8/2017. 6/8 central air units were replaced in 2019. Please notify sales agent prior to any property interaction, as all units are filled.

125 & 127 Avenida De Bahia, Nokomis

$5,000,000

4 Beds ⋅ 4 Baths ⋅ 34275 Zip Code

Presenting an unparalleled opportunity for architectural elegance and opulent living in this exquisite 1.2-acre bayfront estate that is a testament to coastal luxury. With 143 feet of panoramic water frontage overlooking Casey Key, this residence is strategically positioned to capture breathtaking views of the entire bay and the Intracoastal Waterway, along with breathtaking sunsets. As you pass through the front glass double doors, the inviting entryway unveils soaring 22-foot ceilings and a grand staircase that curves gracefully upwards. Meticulously designed living spaces showcase detailed craftsmanship and magnificent architectural elements, setting the stage for a lifestyle defined by sophistication and comfort. Principal rooms are generously proportioned and feature 12-foot ceilings and large windows that flood the interior with natural light. A stunning fireplace and custom built-ins anchor the living room, while the open-concept living space seamlessly flows to the dining area and chef-inspired kitchen. Ideal for entertaining, the kitchen boasts white shaker cabinetry, granite countertops, stainless steel appliances, a Sub-Zero refrigerator, and a 6-burner gas stove with dual ovens by Fisher & Paykel. Enjoy bay views from nearly every room, celebrating the perfect harmony between architecture and landscape. Outside, you’ll discover a lush private paradise at the heart of which is a beautiful custom saltwater pool with a sun shelf, bench seating, water flow features, LED lighting, and a hot tub nestled in a charming cedar arbor. A screened-in patio with a summer kitchen adorned with cypress ceilings offers an ideal setting for alfresco dining while enjoying tranquil views of the shimmering blue waters of the bay. The tropically landscaped yard gently slopes to the water's edge, where you can witness dolphins and manatees swimming. The bayfront dock with a 10,000-pound boat lift and rotating jet ski lift provides convenient boat access to the Gulf of Mexico. As you explore the expansive outdoor space, you'll discover a host of thoughtfully designed features, ensuring both functionality and luxury, including a kayak launch, Trex dock and decking, aluminum fencing, brick paver walkways, outdoor shower, fruit trees, well-fed irrigation system, impact-resistant glass, Hardie board cement siding, Standing Seam Galvalume roof, and prewiring for a generator. Embrace a lifestyle of grandeur and comfort in this one-of-a-kind bayfront estate, offering the epitome of luxury indoor/outdoor living. Schedule your private tour of this waterfront masterpiece today.

1013 Bayshore Road, Nokomis

$3,950,000

5 Beds ⋅ 5 Baths ⋅ South Creek SubDv. ⋅ 34229 Zip Code

1+ acre waterfront property surrounded by 370 feet of water on three sides. This listing includes two parcels: 1) .68 acre with the existing home, and 2) .44 acre buildable lot that can be developed with a large waterfront home on a deep canal. Serene privacy on a cul-de-sac in the secluded South Creek community directly across from Oscar Scherer State Park and just 5 minutes to Pine View School for the Gifted. Located between Sarasota and Venice with easy access to the best amenities in both communities including beaches, shopping, dining, arts, medical and personal services. Private dock for two boats, along with kayak/paddleboard launch, provides easy access to Sarasota’s coastal waterways for endless days enjoying Florida’s year-round sun and fun. The 5,233-square-foot residence has five bedrooms, five baths, plus an in-law studio apartment. All levels feature expansive outdoor lanais/balconies with water views. Living areas are on the second level and include formal living room with cathedral ceiling, formal dining room and family room with wood-burning fireplace. The third level has the owner's retreat featuring sitting room, dual bathrooms, 24x16 bedroom and balcony with the best views of the house. This residence is on the same street as South Creek community amenities which include tennis courts, playground, day dock and night security gate. The singular combination of location, waterfront and size make this a remarkable property for an exceptional lifestyle.

1851 Island Way, Osprey

$9,350,000

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

Along the beaches of Casey Key, a private gated road leads to the exclusive northern end of this coveted barrier island. Sited on nearly 2.5 acres and 150 feet of private beach front, lies a spectacular estate home that has been shared and enjoyed by one family for generations. Designed by renowned architect Timothy Siebert, the property was thoughtfully planned as a gathering place. Wrapped around the inner courtyard, 6 en-suite bedrooms, 7 and 1 half baths, provide guests with access to a resurfaced pool, spa and tennis court and their own private retreats. High ceilings throughout emphasize the grandeur of the spacious rooms. The large kitchen and formal dining rooms are ideal for preparing and serving every culinary delight. Stepping across the expansive front lawn, enhanced with exotic palms, a private boardwalk leads to the powdered sugar quartz sand beach. One can walk for miles with turquoise blue water along the Gulf of Mexico or enjoy a place to rest on the shore with a fabulous book. With no public beach access for miles, guests are pleasantly surprised how quiet and seemingly uninhabited Casey Key remains. Designated as a conservation district by the State of Florida, building is reserved for single family homes. There are no high rises or condominiums permitted and the reputation for its natural beauty and elegance will be retained for generations to come. Private and commercial air travel in nearby Venice and Sarasota are so convenient. Shopping, golf and restaurants are all easily accessible making this destination nearly too good to be true. One of the Sarasota areas most exclusive addresses, North Casey Key will not disappoint.

1544 N Casey Key Road, Osprey

$3,000,000

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

How to describe a masterpiece?! This home was completed in February 2023, and is ready for a new owner to enjoy the breathtaking features it offers. This home is still under the builders warranty! It’s like getting a new home without the two year wait for a custom built home! This gem is truly a one of a kind in The Oaks Country Club Community. The Oaks is considered to be the pinnacle in country club living and best of all THE SELLERS ARE OFFERING TO PAY THE $100,000 CAPITAL CONTRIBUTION ON BEHALF OF THE BUYER! (With acceptable contract.) The owners have painstakingly thought out each detail from purchasing the lot, drawing up plans with an architect to having the home custom built by Henson Contractors, to making sure every item was of the finest quality. The home is situated on one and a half lots, making for a grand appearance with a circular paver drive and a side paver drive leading to the oversized 3 car garage with epoxy floors and built-in cabinetry. The interior exudes quality from the minute you arrive at the custom 4 foot wide solid mahogany front door. Entering the home you will come upon the great room with expansive 24’ ceiling height and a chandelier that is one of the focal points. Other features of the greatroom include built-in bookcases, fireplace and coffered ceiling. Open to the great room is a wet bar enclave just perfect for entertaining. Another breakfast bar area opens to the kitchen. Ah, the kitchen! Every detail is of highest quality including a Miele steam/convection built-in oven, two kitchen sinks (a third sink in the bar enclave), propane gas Wolfe range, custom cabinetry, Sub-zero 42” wide refrigerator, a pantry with sliding ladder and more! The master suite is a dream come true! Two walk in closets that should satisfy those looking for the ultimate in closets. A triple mirrored dressing area in also a unique feature. The master bath is exceptional with large double headed shower and plenty of cabinet and counter space. Currently used as an office, the fourth en-suite bedroom has rich wainscoting, and a private bath. The den is currently used as a piano room and offers floor to ceiling book cases. Upstairs is the loft large loft, another bedroom and bath. Doors lead to the second floor balcony with retractable awning. Other features include an AV closet, a drop zone room for a future elevator. The outdoor living space is outstanding! Large covered lanai with two seating areas, in-wall gas fireplace, plus 3 remote controlled hurricane shutters, travertine flooring, 18x32’ salt water, heated pool with sun shelf and spa. Expansive clear view screening, outdoor shower, outdoor kitchen. Other features are impact windows throughout, “Lutron” programmable light switches, 3 air handlers, dream laundry room, powder room with Murano vessel sink, two tankless recirculating hot water heaters, Generac 38 kw whole-house standby generator, whole house water filter, “control4” home automation (security, lighting and comfort/temperature)and extensive landscaping gives a well established look. Reading a list of features is nothing compared to coming to see this showplace! If you are in the market for a classic and timeless new home, you will not find anything finer on the market! HOA fees do not include mandatory Country Club Fees. Check pricing schedule for details. Come take a look at The Oaks Country Club and if your are not familiar with The Oaks it is a historic landmark community - where luxury lives!

350 Sugar Mill Drive, Osprey

$2,200,000

5 Beds ⋅ 7 Baths ⋅ Oaks The SubDv. ⋅ 34229 Zip Code

Introducing The Grand Estate at The Oaks Bayside! Roof is brand New 1 year old. Step into a world of opulence and tranquility, nestled within the exclusive gates of The Oaks Bayside. This remarkable residence stands as a testament to luxury living, enveloped by lush greenery, majestic oak trees, and vibrant tropical flora that set the stage for an extraordinary retreat. As you approach, a captivating driveway adorned with elegant pavers leads to the 3-car side-load garage, ensuring ample space for your vehicles. Welcoming you to the front porch are stately columns that frame the grand double-door entry, hinting at the lavish interior that lies beyond. Upon crossing the threshold, be prepared to be awed by the lavish details that define this residence. Marvel at the pristine marble flooring that gleams under the abundant natural light that bathes the space. The exquisite plantation shutters grace every window, inviting you to discover the myriad of exceptional features. To the left, an exquisite office awaits, replete with built-in bookshelves and a desk, ideal for productivity and focus. Pocketing doors provide an oasis of quiet when needed. To the right, an expansive open space with a backlit tray ceiling presents endless possibilities—a perfect enclave for your grand piano, a library of cherished books, or an elegant formal dining room. Ahead lies the formal living room, where a window of grand proportions transforms the outdoors into an integral part of your living experience. Towering ceilings, a crackling fireplace, and seamless access to the private pool area create an ambiance of comfort and sophistication. Prepare to be enamored by the kitchen's design, where a charming breakfast nook overlooks the pool through an aquarium window. A sprawling breakfast bar, dual sinks, an island for culinary creativity, a double wall oven, and a butler's pantry define the culinary haven. This space seamlessly transitions into the family room, where sliding glass doors open to the pool, accompanied by a wood-burning fireplace, a wet bar, and a convenient built-in desk—a haven for family togetherness. The master suite beckons with its spaciousness, complete with a cozy sitting area bathed in sunlight and pool access through sliding glass doors. The en suite bath boasts a walk-in shower and a garden tub with picturesque windows framing your private tropical haven. Outside, discover the ultimate private oasis—your pool area. A resplendent pool and separate spa take center stage, embraced by a travertine deck and a covered patio, making every day feel like a vacation. With 6000 square feet of living space, 5 bedrooms, 5 full bathrooms, and 2 half baths, this estate is a realm of comfort and luxury. 2 AC systems are 2 years old, And that's just the beginning! As a resident of The Oaks, you gain access to The Oaks Club, offering two golf courses, tennis courts, pickleball courts, a croquet court, a well-equipped fitness center, and exceptional dining. Conveniently situated near esteemed institutions like Pine View School, Historic Spanish Point, Casey Key, and Oscar Sherer State Park, you'll enjoy the best of both worlds—tranquility and accessibility. Your dream home is waiting. Schedule your private showing today and embrace a life of timeless elegance!

340 Osprey Point Dr, Osprey

$3,510,000

5 Beds ⋅ 6 Baths ⋅ Sorrento Shores SubDv. ⋅ 34229 Zip Code

Luxury waterfront gated estate directly on the Intracoastal waterway with 2 boat lifts and one covered for weather protection, has sailboat water for larger boats dockside, 2 story with Master suites on both levels, 2nd floor has large viewing deck/workout room/office and small kitchen. Architecture by George Merlin, construction quality exceeds today’s requirements, ‘solid pour’, tile roof, marble floors, security system, elevator, detached guesthouse now serves as theatre room/rec room, solar heated pool and spa with LP gas heater as needed, outdoor bathroom and plenty of storage, 4 car garage provides plenty of room for cars, SUV’s, or smaller RV. Approximately 135’ of waterfrontage, being sold furnished as you see it with 2 boats and 2 jet skis negotiable. First level has 2 kitchens back to back, 12 zone AC system, central vacuum, security system, located on quiet cul de sac with gated entry, Feauture sheet upon request or at showings.

425 Titian Drive, Osprey

$4,400,000

3 Beds ⋅ 5 Baths ⋅ Casey Key Estates SubDv. ⋅ 34275 Zip Code

Remarkable Gulf to Bay waterfront estate on the highly exclusive Island enclave of Casey Key, where opulence and serenity unite in perfect harmony. The highly sought-after gulf to bay position allows for the optimal experience in waterfront living. No trade-offs between boating and beaches, this property indulges it all. The bayside overlooks Blackburn Bay, with a dock and lift making the waters easily accessible by boat. The gulf side features a private beach right outside the front door, literally your own slice of the paradise that people converge from across the world to experience. With walls of glass and an abundance of covered balcony space, this property offers an ideal vantage to capture sunrise over the bay, sunset over the gulf, and the turquoise waters of the Gulf of Mexico all day in between. The expansive, open floor plan is ideally suited for both entertaining and water gazing, with seating areas thoughtfully positioned throughout both floors. Added luxuries include a wet bar, elevator, upstairs laundry room off the owner’s suite, and a dedicated study on the main level. The neutral palette affords the opportunity to easily customize decor and finishes to suit your design preferences. Outside, the resort-like setting is enhanced by an infinity pool and spa, and the grounds feature lush lawns, paver paths, and outdoor dining retreats. Additionally, the property boasts 107 feet of water frontage on the Gulf of Mexico and 80 feet of frontage on Blackburn Bay, providing an extensive and stunning connection to both bodies of water. Savor the tranquility of Gulf to Bay living. Don't miss the opportunity to make this exquisite property your own and experience the epitome of coastal luxury.

1704 Casey Key Road, Nokomis

$3,750,000

5 Beds ⋅ 4 Baths ⋅ N/A SubDv. ⋅ 34275 Zip Code

Welcome to your Island retreat on Casey Key! This exquisite beach house exudes classic charm and offers a truly idyllic setting. Nestled on nearly an acre of land, this hidden gem provides the perfect blend of privacy and proximity to a private deeded beach easement, where miles of pristine shoreline await your exploration. Located on Cutlass Bayou, the home's bayside waterfrontage is nestled on a protected basin. With easy boating access to the Intracoastal Waterway, you'll appreciate the convenience of a private boat launch and dock. The mean high water depth of 4 feet ensures smooth sailing on your aquatic adventures. Embrace the essence of outdoor living with the exquisite outdoor kitchen, dining, and living areas. Revel in the classic Florida lifestyle as you dine al fresco. Plans for a new pool and spa are underway, and are currently in the permitting process.Step inside the home, where limestone floors and an abundance of natural light create an inviting ambiance. The flexible floor plan allows for versatile use, with a home office and plenty of room for guests. The kitchen is a culinary dream, featuring top-of-the-line Decor, Bosch, and Sub-Zero appliances. Spacious family and living rooms, complemented by a beautiful fireplace, offer ample room for gathering and entertaining. A separate dining room provides an elegant setting for formal meals. Ascend to the master bedroom upstairs and wake up to Gulf views. Witness stunning sunsets from the comfort of your own private retreat. Three additional generously sized bedrooms, two full baths complete the second floor. For the avid hobbyist or water sports enthusiast, the three-car garage and workshop provide the perfect space to tinker, store boating gear, and house water sports toys. Located near the north bridge, accessing and departing the island is a breeze, offering added convenience. Positioned between Sarasota and Venice, you'll enjoy easy access to a wealth of shopping and dining options. Discover why Casey Key, an eight-mile-long barrier island, is hailed as the jewel of the Gulf Coast and holds a special place in the hearts of its fortunate residents.

3760 Casey Key Road, Nokomis

$5,300,000

4 Beds ⋅ 6 Baths ⋅ Casey Key SubDv. ⋅ 34275 Zip Code

Auction Property. AUCTION BIDDING OPEN: Bidding ends June 25th. Previously Listed $9.5M. Current High Bid $5M. No Reserve. Showings Saturday & Sunday 1-4 PM & By Appt. This luxurious modern home is the last residential home built by the illustrious designer Carl Abbott and was completed in 2019 by Michael K. Walker. The home features the finest finishes and materials, creating a beautiful canvas for residents to make it their own. The spacious kitchen and dining room have a wall of windows overlooking the Gulf of Mexico. The interior has clean, modern lines and sleek design with Gulf views from all of the main rooms. A patio off the living room is perfect for enjoying a cup of coffee or morning cocktail while enjoying the waterfront breeze. The primary suite has a private balcony and an ensuite bathroom with a soaking tub. This beach paradise is located on Casey Key, one of the most exclusive neighborhoods in Nokomis. The contemporary aesthetic perfectly compliments the surrounding natural beauty of the seashore. Conveniently positioned between Venice and Sarasota, private and commercial air travel is easily accessible. Restaurants, shopping, marinas, golf and tennis are all just minutes away.

4019 Casey Key Road, Nokomis

$2,700,000

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

**SPACIOUS, LUXURIOUS and BEAUTIFULLY RENOVATED, GOLF COURSE ESTATE** Boasts OVER 9,000sf and is situated on a prominent, private cul de sac lot of Over 3/4 Acres. Expansive room abounds in this LIGHT and BRIGHT Open Floorplan consisting of 4 Beds + 4/2 Baths + Office/Library + Home Theater + Game Room w/ Wet Bar, Loft, Balcony, etc. and even includes highly coveted, oversized and split 4-Car Garage(s). This MOVE-IN READY home has been tastefully updated and is ideal for indoor and outdoor entertaining! The elegant first level primary bedroom suite features high ceilings, multiple walk-in closets, garden tub, large custom walk-in shower and an adjacent nursery/fitness/den area. The sprawling, gourmet kitchen entails a generous island and counter seating area, premium stainless steel appliances, granite counters, solid wood cabinets, walk-in pantry and more. The upstairs loft leads to two vast bedroom suites, theater room and screened terrace/balcony. Enjoy the utmost in Florida outdoor living with a Heated Pool & Spa with Fire features and a large screened lanai with Outdoor Kitchen and seating areas while overlooking the serene interior, Heron Golf Course. 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, 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 available. **ENJOY THE 3D VIRTUAL TOUR and AERIAL VIDEO**

854 Macewen Drive, Osprey

View All Latest Osprey/Nokomis 5000+ Sq. Ft. Properties for Sale

5000+ Sq. Ft. Osprey/Nokomis Real Estate

How much is your home worth?

How much is your home worth?