Oaks Real Estate, Homes, Condos for Sale in Osprey/Nokomis, FL - 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

$775,000

2 Beds ⋅ 2 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Your OPPORTUNITY to call THE OAKS Country Club home has just become AFFORDABLE! This TURNKEY-FURNISHED ESTATE HOME by Legendary Architect Bo MacEwen, is Located on a Cul De Sac in the PRESTIGIOUS SAINT JAMES PARK Neighborhood. If You Are Seeking EXCLUSIVITY and PRIVACY You'll Appreciate the Nearly 1/3rd Acre of Lusciously Landscaped Grounds Overlooking the Eagle Golf Course Located Near the Clubhouse and THE OAKS World-Class Amenities. OUTSTANDING FEATURES of this Elegant Home are the HURRICANE IMPACT WINDOWS & SLIDING DOORS (Installed 2019 & 2024), NEWER ROOF (2024), and NEWER STAINLESS KITCHEN AIDE APPLIANCES, with Solid-Wood Cabinetry. ELEGANT FEATURES of this Distinctive Home include; Crown Molding, Wainscoting, Wood-Burning Fireplace, Engineered Hardwood and Tile Floors plus a Hidden Wet Bar for Entertaining and Personal Enjoyment. An Abundance of Sunlight Pours through the EXPANSIVE Sliders Mid-Day to Welcome You Home. The Primary Suite is Spacious and Inviting with a Private Dressing Area; Featuring a Walk-In Closet, Dressing Table, Dual Vanities, Private Commode, Soaking Tub and Custom-Tiled Shower. The 2nd Bedroom has its own En-Suite Bathroom and Can Also Serve as a Spacious Den with Closet. Entertaining in Your CLASSIC OVER-SIZED Dining Room is Wonderful for Extended Family and Guests. Once You Step Outside onto the INCREDIBLE SCREENED LANAI (48X20 feet) and Gaze Upon the Luscious Landscaping and Serene View, You Will Realize that this is the Place You Can Call Home! Spectacular Sunsets with Western Exposure Await You on this Lanai Where Dreams Unfold. The Oversized 2- Car Garage has a Charging Station for Electric Car Enthusiasts. THE OAKS Country Club Community is Among One of America’s Healthiest Clubs, having been Awarded Numerous Accolades including: Platinum Club of America, Emerald Club of the World, and Elite Distinguished Club of the World. Members enjoy 3 Restaurants, a Ballroom, a State-of-the-Art Fitness Center, Junior Olympic Heated Community Pool, an Award-Winning Racquets Program with 12 Har-Tru Hydro-Grid Tennis Courts, 4 Pickleball Courts, plus a Croquet Facility and more. The Premier Attractions in THE OAKS are the TWO 18-Hole Championship GOLF courses. Membership is Mandatory; Either Select a Golf or a Social Membership. Located Close to the World Famous Siesta Key Beach and a Short Drive to Downtown Sarasota for World-Class Cultural Entertainment, this Amazing Lifestyle is Awaiting You. Call Today for Your Private Showing.

227 Saint James Park, Osprey

$1,445,000

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

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

422 Blue Garden Lane, Osprey

$1,900,000

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

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

168 Coastal Hammock Court, Osprey

$3,700,000

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

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

650 Oaks Creek Court, Osprey

$679,000

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

**EXPERIENCE EFFORTLESS LIVING in this BEAUTIFULLY UPDATED TOWNHOUSE with SERENE WATER VIEWS** Located behind the Secure Gates of The Oaks Preserve, Golf & Country Club neighborhood, this delightful residence features 2 En Suite Bedrooms on the 2nd Floor, 2 Full and 1 Half Baths, and offers a refined yet relaxed lifestyle surrounded by mature oak canopies and tranquil lake views. The main living area entails an inviting great room that opens to serene water views framed by palms and natural greenery while the European-style kitchen is thoughtfully designed with premium SubZero, Wolf and Bosch appliances, modern wood cabinetry, polished granite countertops, and durable ceramic tile flooring—ideal for both everyday living and entertaining. Architectural details add warmth and character throughout, including hand-plastered walls with art niches, graceful archways, plantation shutters, and sisal carpeting. Just off the entry foyer, you’ll find a convenient powder room and a separate laundry room. A private brick balcony provides ample space for outdoor dining or relaxing while enjoying the peaceful surroundings. The primary suite overlooks the lake and includes two walk-in closets and a spacious bathroom featuring dual vanities, walk-in shower, jacuzzi tub and appointed with upscale finishes. The guest suite is equally comfortable, complete with built-in shelving and ample storage. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS program with 12 Har-Tru Hydro-Grid TENNIS courts (4 lighted), 4 PICKLEBALL Courts, wonderful CROQUET facility, state-of-the-art FITNESS center and junior Olympic, heated community SWIMMING POOL, Bocce, Basketball Court, Playground and more! 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.

33 Bishops Court Road Unit 118, 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

$1,245,000

3 Beds ⋅ 2 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Impeccable is the only way to describe this charming property! This stunning 3 bedroom, 2 bathroom residence has been completely remodeled to create a luxurious yet comfortable, livable home. No detail has been overlooked in the complete renovation, making it truly gorgeous and unique. The interior is incredible and has so many high-end features; tile flooring designed to look like wood, quartzite countertops, a stylish coffee bar, and a beautifully crafted hood vent. The recent addition of an entire deck off to the side of the home enhances the outdoor living space. The deck includes a canopy that extends to cover part of the area, providing shade for the dining table, swinging chair, and grill. Additionally, a hot tub has been added for your relaxation. The home boasts three bedrooms, with one currently being used as an office. The previously enclosed Florida room has been transformed into a spacious family room, perfect for gatherings. The interior design, crafted by a professional, ensures that no detail no matter how big or small has been missed. The property also features a huge yard, the largest in the neighborhood, providing ample space for outdoor activities, and the pièce de résistance, a dreamy view of the pond. Residents enjoy access to a community pool and clubhouse, both within walking distance from the house. Plus, landscape maintenance is included, making it a hassle-free living experience. With mandatory membership, residents can enjoy all the amenities The Oaks offers. There is currently no waiting list for either Golf or Sports/Social membership.

17 Bayhead Lane, Osprey

$2,800,000

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

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

662 Fernwalk Lane, Osprey

$1,350,000

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

Located inside the gates of The Oaks Club, this 3 bedroom 2.5 bathroom home offers an exceptional opportunity for luxury country club living. The property features a new roof and impact windows. Situated in a community recognized for its world-class amenities, residents enjoy access to two 18-hole championship golf courses—the Eagle and Heron courses—along with comprehensive practice facilities and driving ranges. The member-owned Oaks Club features a 34,000-square-foot clubhouse with multiple dining venues, tennis courts, pickleball courts,a resort-style pool, and a 7,500-square-foot fitness center. Beyond the community gates, this location provides convenient access to Gulf Coast beaches, scenic trails including The Legacy Trail, local parks, as well as the cultural offerings of Sarasota and Venice. Schedule a private tour to explore the property and experience the distinct lifestyle of The Oaks Club.

226 Saint James Park, Osprey

$1,800,000

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

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

222 Saint James Park, Osprey

$699,000

3 Beds ⋅ 2 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Remarkable 3 bedroom 2 bathroom home in Emerald Woods now available for purchase. Nestled in the Oaks Preserve Neighborhood and offering a maintenance free lifestyle with 24 hour guarded gate. Features include; Beautiful Tray Ceilings, Crown Moldings, Plantation Shutters, Solid Surface Countertops, Tile flooring throughout living spaces, and an Spectacular Owner’s Suite with multiple walk-in closets and sitting area.The Oaks Club boasts 2 Championship Golf Courses, 12 Har-Tru Tennis Courts (4 lighted), State Of The Art Fitness Center, Junior Olympic Swimming Pool, Regulation Croquet Court, 4 Pickle Ball Courts, along with numerous dining, social and recreational options. Conveniently located near Florida's top rated Pine View School, the Legacy Bike Trail, and the world renowned beaches of Siesta Key, Casey Key, and so much more. Just a short distance from shops, restaurants, and the cultural offerings of downtown Sarasota. Membership to the club is mandatory. Some images may have been Virtually Staged/Edited...

299 Turquoise Lane, Osprey

$575,000

Oaks SubDv. ⋅ 34229 Zip Code

One of the last available homesites in The Oaks Bayside. Almost 1/2 acre, at 17,647-square-feet, this exceptional lot presents a rare opportunity to build a custom luxury residence in one of Sarasota's most established and prestigious gated communities. Located behind the 24-hour staffed gates of The Oaks Bayside, this desirable homesite is ready to be transformed into the home you've always envisioned. Bring your own builder and architect and create a residence tailored to your lifestyle, surrounded by majestic oak trees, winding streets, and distinctive estate homes. The Oaks Bayside is renowned for its peaceful Old Florida charm, mature landscaping, and prime location along Little Sarasota Bay. This sought-after neighborhood offers a unique blend of privacy, natural beauty, and convenience, just minutes from the beaches of Casey Key, downtown Sarasota, and the area's finest shopping, dining, and cultural attractions. Ownership includes membership in The Oaks Club, one of Florida's most respected private club communities, featuring two championship 18-hole golf courses, 12 Har-Tru tennis courts, four pickleball courts, croquet, a state-of-the-art WellFit Center, Junior Olympic heated swimming pool, bocce, basketball, playground facilities, multiple dining venues, and a vibrant year-round social calendar. Club membership is required, and there is currently NO WAITING LIST for either Golf or Sports/Social membership.

143 Osprey Point Drive, Osprey

$1,445,000

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

Virtually Staged. A unique offering! This like-new, never lived in Spanish mission style home is a rare find. Move in ready and set on a private .63 acre lot in The Oaks Preserve, the open floor plan includes 3 en suite bedrooms and 3.5 baths. Thoughtfully designed, it welcomes you with a circular driveway, porte cochere, and a detached 2 car garage equipped with an electric vehicle charger. Inside, soaring ceilings, neutral tile and wood flooring, recessed lighting, and an electric fireplace create a warm, refined ambiance. Built to current codes with impact glass and a new roof, the home offers peace of mind and the efficiency of modern construction. The chef’s kitchen, with Bosch stainless appliances, a gas 5 burner cooktop, soft close cabinetry, a center island with wine storage, and stylish tile finishes, has a breakfast bar and opens to the dining room. The luxurious master suite features a vaulted ceiling, spacious walk-in closet, and a spa inspired bath complete with freestanding tub, glass enclosed shower, dual vanities, bidet, and exquisite tilework. A central brick paver courtyard provides a private tropical retreat with ample room to add a pool. Sarasota’s premier golf and country club, The Oaks Club’s unmatched amenities include two championship 18-holf golf courses, 12 tennis courts and 4 pickleball courts, the state-of-the-art WellFit Center, a junior Olympic pool, a celebrated social calendar, and a wide array of dining options and recreational activities. There is currently no waiting list for either Golf or Sports/Social membership

360 N Point Road, Osprey

$1,500,000

Oaks SubDv. ⋅ 34229 Zip Code

Exceptional opportunity to secure a rarely available 0.66-acre vacant lot in the esteemed Oaks Country Club community. Bring your vision to life and build a custom luxury estate with renowned builder Henson Construction. Surrounded by stunning natural beauty and upscale amenities, this prime homesite offers the ideal setting for refined country club living. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS 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, Bocce, Basketball Court, Playground and more! 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.

893 Macewen Drive, Osprey

$699,000

3 Beds ⋅ 2 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

**LOCATED IN A DESIRABLE, MAINTENANCE-FREE, COUNTRY CLUB COMMUNITY** this Charming and Cozy 3-Bedroom, 2-Full Bath home sits on a premium Corner Lot directly across from the Community Pool. Featuring a NEW ROOF, 2-Car Garage, and a Spacious and Private screened lanai perfect for relaxing or entertaining, this home offers comfort and convenience throughout. Situated in Flood Zone “X” for added peace of mind. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS 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, Bocce, Basketball Court, Playground and more! 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.

103 Bishops Court Road, Osprey

$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

$1,050,000

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

Thoughtfully Built MAINTENANCE-FREE Court Yard Life Style Home in Bishops Court in the Oaks Preserve Neighborhood. This Rare Unique Home Design Features: 3 Extra Large Bedrooms, 3 Full Baths, Oversized Main Floor Master Suite w/Sitting Room and Door to Private Back Patio, plus a Wall of Sliders Looking out to the Court Yard Pool Area, Tall Ceilings, Large Walk-in Closet w/Built-ins, Brand New Carpeting plus a 5-Piece Master Bath w/Soaking Tub; Formal Living and Dining Room are Open w/Tall Ceilings, Slider to Pool plus a Den/Library Room off the Living Room and Solid Wood Plank Flooring throughout; Open Kitchen w/Granite Counters and Breakfast Room w/Slider to Pool joined by a Family Room w/Fire Place and Solid Wood Plank Flooring; Pool Bath w/French Door, Main Floor Laundry Room w/Sink, Fabulous Upstairs Suite perfect for Guests or Extended Family w/Bonus Room, 2 Guest Bed Rooms w/Jack and Jill Bath; Extensive Crown Molding, Plantation Shutters throughout, (2026) New Interior Paint, Central Vac, Large Side Load 2 Car Garage w/Storage, Newly Resurfaced Pool and Spa in the Screened-in Court Yard Entertaining Area, Court Yard Entry Gate, (2025) Brand New Designer Flat Tile Roof, (2026) NEW Upstairs AC, (2026) New AC Duct Work, (2026) Painted Pool Deck, (2026) Brand New Paver Driveway. WITH A FEW SIMPLE TOUCHES YOU CAN MAKE THIS HOME ABSOLUTELY FABULOUS! Have VISITORS Coming? NO PROBLEM. THIS HOME MAKES THE PERFECT ENTERTAINING OR SEASONAL FLOOR PLAN OFFERING A PRIVATE UPSTAIRS GUEST SUITE! Neighborhood Community Features: Local Community Pool, 24-Hour Secured Guard Gate, Lush Florida Landscaping and Irrigation are all included in the Maintenance Free Living. The OAKS GOLF & COUNTRY CLUB IS ONE OF SARASOTA'S PREMIER EQUITY "Creme de la Creme" GOLF COMMUNITIES! This amazing COUNTRY CLUB Features: Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World Golfing (One of America’s Healthiest Clubs), Three Restaurants, Ballroom, Two 18-Hole Championship GOLF Courses, Award-Winning RACQUET Program w/12 HAR-TRU Hydro-Grid TENNIS COURTS, 4 PICKLE-BALL Courts, CROQUET, State of the Art FITNESS Center, Junior Olympic Heated Pool, Bocce Ball and Basketball Court, Playground Area plus so much more! Located just Minutes to the Top Rated Pine View School, Legacy Bike Trail, Florida's Best Coastal Beaches, Restaurants, Shopping and Costco. THE OAKS CLUB MEMBERSHIP IS REQUIRED w/NO WAIT-LIST for SOCIAL or GOLF Memberships. BUYER BONUS: Seller is Offering $80,000 towards Buyer's Capital Contribution Fee for Club Membership Option!!! ***Most Furnishings are Available Under a Separate Contract.

61 Bayhead Lane, Osprey

$1,385,000

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

Meticulously maintained and updated with care, this 3 bedroom, 3 bath + den/study home in The Oaks Clubside offers beautiful views. A mixture between clean modern lines and cottage chic this house feels cozy. Yet it has an open floor plan, soaring ceilings and every room in the house is light and bright. The formal living room opens to the large lanai and pool with Southern exposure. The view over the lake to the Eagle #6 is simply gorgeous! It is one of the most stunning views in the neighborhood. There is plenty of room to host friends and loved ones. Serve a meal in the formal dining room, have a causal lunch in the kitchen nook or at the breakfast bar, or dine al fresco under the large, covered area overlooking the pool. From the luxurious master suite to the guest bedrooms, this home is beautifully appointed and showcases the finest of details and improvements, including a new roof, impact windows and doors and pretty, updated landscaping. The Oaks, Sarasota’s premier golf and country club, offers two championship golf courses, HAR-TRU tennis courts, pickleball, croquet, and a state-of-the-art WellFit Center.

434 Macewen Drive, Osprey

$1,865,160

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

**IMPRESSIVE GOLF COURSE ESTATE IN THE HIGHLY SOUGHT-AFTER OAKS COUNTRY CLUB** Situated on an oversized 0.59-acre lot, this exceptional, meticulously-maintained residence features many upgrades and offers breathtaking garden and golf course views in a private, serene setting. Impressive curb appeal and beautifully manicured landscaping welcome you into a beautifully appointed home featuring 4 BEDROOMS plus a STUDY/DEN, 3 FULL and 1 HALF BATHS. Inside, you’ll find high ceilings, elegant crown molding, a cozy fireplace, plantation shutters, custom built-ins, and rich hardwood flooring throughout. The spacious kitchen is designed for both functionality and style, showcasing granite countertops and black stainless KitchenAid appliances. The expansive primary suite is a true retreat, complete with multiple walk-in closets, dual vanities, a soaking tub, and a custom-tiled shower. Enjoy Florida living at its finest on the screened lanai, featuring a heated pool and spa, travertine marble pool deck, and a large covered entertaining area—all overlooking tranquil golf course and garden views for ultimate privacy. Additional highlights include a 3-car garage and thoughtfully designed indoor-outdoor living spaces perfect for entertaining or relaxing. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS 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, Bocce, Basketball Court, Playground and more! 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. **Please Enjoy Viewing the 3D VIRTUAL TOUR**

448 E Macewen Drive, Osprey

$1,600,000

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

Experience the charm of this original Bo MacEwen–designed home in The Oaks Clubside. Ideally located on a quiet cul-de-sac, in the Saint James Park enclave, this 3 bedroom residence with 2.5 baths, overlooks the opening hole of the Heron Course. Clean, bright and beautifully updated and maintained, this home has an open floor plan and features high, coffered ceilings, crown molding, French doors and gleaming mahogany floors. Extensively improved, the home has been repainted inside and out, with refurbished flooring throughout (including the garage), new carpeting, a newly renovated laundry room, new pool equipment with a saltwater system, a new driveway, updated fencing, and refreshed landscaping. The open kitchen has been updated and offers quartz countertops, Sub-Zero refrigeration, a wine fridge, beverage drawers, custom cabinetry, walk-in pantry and an island that serves as a breakfast bar. The great room opens to the lanai with pool, spa, and golf views. The split plan provides privacy with a remodeled master suite featuring a spa-like bath and custom walk-in closet. The south side includes an en suite guest room and a third bedroom/office with lanai access and golf views. Additional features include a 2-car garage with epoxy floor and storage, plantation shutters, a newer roof (2020), hurricane shades and new Pella bay windows. Saint James Park offers easy access to all of The Oaks Club’s offerings: tennis. Pickleball courts, croquet lawn, a state-of-the are WellFit Center, and golf facilities. Members enjoy a wide variety of dining options and a robust social calendar.

228 Saint James Park, Osprey

$1,495,000

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

Located on a quiet cul-de-sac within the gates of The Oaks Clubside, this custom-built residence at 554 Dove Pointe offers privacy, space, and the refined lifestyle of one of Sarasota County’s most established country club communities. Set on a beautifully landscaped homesite covering more than a half-acre, the property enjoys exceptional curb appeal with a circular drive, mature trees, and a fully fenced backyard—an ideal setting for pets, outdoor play, or peaceful evenings surrounded by nature. Spanning 3,500+ square feet of interior living space, the thoughtfully designed floor plan includes four bedrooms, three-and-a-half baths, and a dedicated study/den, creating flexible space for everyday living, guests, or working from home. The home has been carefully maintained and enhanced with a new roof completed in 2025, providing peace of mind for years to come. A welcoming foyer leads into the main living areas where high ceilings, crown molding, and expansive sightlines create an inviting atmosphere. The living/dining room is anchored by a gas fireplace and wet bar, while walls of sliding glass doors and French doors open to the outdoor living spaces, blending interior comfort with Florida’s year-round indoor-outdoor lifestyle. The chef’s kitchen serves as the center of the home, offering solid wood cabinetry, granite countertops and backsplash, stainless steel appliances, a walk-in pantry, and an expansive island with breakfast bar seating. The space flows seamlessly into the family room and breakfast nook, creating a comfortable gathering area for casual meals and conversation. The primary suite is privately situated and features terrace access, a spacious walk-in closet, and an en-suite bath designed for relaxation with dual vanities, soaking tub, and a walk-in shower. Three additional guest bedrooms are arranged in a split configuration, two featuring en-suite baths and walk-in closets, ensuring privacy and comfort for visitors. Outdoor living is designed for both relaxation and entertaining. The screened lanai and pavered pool deck surround a private swimming pool with raised spa and summer kitchen, creating an inviting setting for gatherings or quiet afternoons at home. Beyond the pool area, the fenced backyard offers an expansive lawn ideal for pets or outdoor enjoyment. Residents of The Oaks Country Club enjoy a gated setting spanning more than 1,000 acres along Little Sarasota Bay. The required membership provides access to an exceptional collection of amenities including two championship 18-hole golf courses, 12 Har-Tru tennis courts, croquet lawns, a fitness center, heated community pool, and multiple dining venues. Ideally located in Osprey between Sarasota and Venice, this home places residents just minutes from the Gulf beaches of Casey Key and Siesta Key, waterfront dining, and everyday conveniences. Nearby cultural destinations such as Selby Gardens, Sarasota Opera House, and The Bay Park anchor Sarasota’s renowned Cultural Coast, while marinas, nature preserves, and scenic trails offer endless opportunities to enjoy the area’s outdoor lifestyle. This property presents a rare opportunity to enjoy private, pet-friendly living on a spacious cul-de-sac homesite within one of Sarasota’s premier golf and country club communities.

554 Dove Pointe, Osprey

$2,300,000

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

This beautiful custom designed home will captivate you from the moment you enter the front door. Located in the extremely sought after Oaks Country Club, this recently renovated home is sure to impress with picturesque views of the golf course. Privacy and entertaining are at the top of the list for this tastefully remodeled home, offering 4 bedrooms and 5 ½ baths. Marble and wood floors are in the main living areas. You are certain to have plenty of room for visiting family and friends, with a living room, fireplace, and family room all overlooking large pool area, lush landscaping, and golf course. The kitchen is waiting for your culinary skills, with stunning Quartz countertops, an island, a Thermador gas range, complete stainless appliances including double ovens with a warming drawer, extensive wood cabinetry, wine refrigeration and dining space for six. The dining room seats 12 comfortably, has handsome wood floors, and plenty of light. Two full size closet pantries offer plenty of storage space for kitchenware. The study/den has extensive built in shelving for your book collection. hurricane impact sliding doors lead you to the immense lanai, with a completely outfitted outdoor kitchen and fireplace, and multiple seating areas for dining al fresco. The generous pool and spa, all newly surfaced, are sure to complete your lifestyle. The first floor has an extremely spacious owner’s suite complete with a sitting area and three custom designed walk in closets. Also, an exercise or bonus room completes the owner’s wing. The generous bath has a walk in shower, jetted Jacuzzi, and separate vanity areas. An en suite guest bedroom is on the first floor as well. The elevator or stairs take you to the second level where you will find two en suite guest rooms complete with a cozy sitting area. This home is ready for its new owners with newer air conditioning systems, pool equipment, epoxy flooring in the 3 car garage and professional landscaping. The Oaks Country Club is a Platinum Club of America, and Emerald Club, offering two 18 hole golf courses, tennis, pickleball, croquet, fitness center, dining, and an extremely active social calendar. No need to look further, this is the one! Membership is required. Conveniently located to beautiful beaches, the Legacy

896 Macewen Drive, Osprey

$1,300,000

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

METICULOUSLY MAINTAINED AND THOUGHTFULLY UPDATED, THIS EXCEPTIONAL RESIDENCE IS PRIVATELY SITUATED ON A SERENE LOT WITH BEAUTIFUL GARDEN AND PRESERVE VIEWS. Located in Flood Zone “X” (no flood insurance required), the home is tucked behind the secure gates of the highly sought-after Bayside neighborhood within The Oaks Country Club, just steps from Little Sarasota Bay. The home offers 3 En Suite Bedrooms, 3 Full and 1 Half Baths. The Updated Kitchen features Quartz countertops, custom hardwood cabinetry, and premium appliances, including Sub-Zero and Wolf. A cozy family room with a wood-burning fireplace provides an inviting gathering space, while impressive Brazilian cherry hardwood flooring enhances the living and dining areas. The spacious primary suite includes a walk-in closet and a luxurious bath with dual vanities, a custom-tiled shower, and a soaking tub. Outdoor living is highlighted by a large screened and covered entertaining area, along with a stunning open-air pool overlooking the tranquil preserve. Additional features include a circular driveway and a peaceful, private setting. RECENT UPDATES include Hurricane IMPACT Windows (2019), HVAC (2021), ROOF (2014), Flooring (2020), Etc. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS 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, Bocce, Basketball Court, Playground and more! 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**

25 Sugar Mill Drive, Osprey

$2,000,000

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

ELEGANT HOME WITH ALL THE BELLS AND WHISTLES. SITTING ON A DOUBLE LOT! ON HERON GOLF COURSE, BEAUTIFUL OUTDOOR KITCHEN, HIGH CEILINGS AND CROWN MOLDING!

895 Macewen Drive, Osprey

$1,950,000

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

Under contract-accepting backup offers. **ELEGANT UPDATED RESIDENCE IN THE OAKS | MODERN COMFORT ON A .83-ACRE CORNER LOT** Welcome to 538 Dove Pointe, an exceptional residence in the secure and gated Oaks Country Club community in Osprey, Florida. Set on a generous .83-acre elevated lot, this beautifully landscaped property offers the perfect combination of privacy, sophistication, and modern comfort. Built in 2002, this newer home showcases timeless architecture with a thoughtful layout and extensive 2023–2025 updates throughout. From its striking curb appeal to its serene outdoor living spaces, every detail has been meticulously curated. Inside, the home offers 4 EN SUITE BEDROOMS, 5.5 BATHS, and a 3-CAR GARAGE that’s been freshly painted and upgraded with a new epoxy floor. Walls of glass fill the home with natural light, complemented by plantation shutters and new motorized window shades throughout. Major updates include a new tile roof (August 2025), two new HVAC units, new LED lighting, and new outlets and light switches across the home. The entire interior and exterior were freshly painted in 2023, giving the home a bright and modern aesthetic. The primary suite is a private retreat, featuring new flooring, a spacious bath, and a bonus office/dressing area for added versatility. A separate office or sitting room, also with new floors, provides ideal space for remote work or quiet relaxation. The three additional bedrooms feature new carpeting, creating a cohesive and comfortable atmosphere. The chef’s kitchen is equipped with new stainless-steel appliances (refrigerator, dishwasher, – all 2025) and flows seamlessly to the main living areas and outdoor entertainment space. There is a new 2025 washer and dryer as well. Step outside to your private Florida oasis — a covered lanai with a full outdoor kitchen and a large motorized Sunbrella shade for comfort and convenience. The property’s two fountains (one new) and professionally graded, elevated landscaping create a lush and tranquil environment perfect for al fresco dining or quiet reflection. The Oaks is a distinguished, 24hr guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS 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, Bocce, Basketball Court, Playground and more! 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. **Please Enjoy Viewing the 3D VIRTUAL TOUR**

538 Dove Pointe Drive, Osprey

$2,100,000

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

**INCREDIBLE TRANSFORMATION OF THIS MOVE-IN READY, GOLF COURSE ESTATE** From the Reimagined Entryway and through the Stunning Iron double front door, you will be captivated by the attention to detail throughout this elegantly appointed residence located on an Over Half Acre, Private lot on the Interior, Heron Golf Course in the highly-sought after, OAKS COUNTRY CLUB community. The recently completed, extensive renovation throughout its expanded footprint with 4-BEDROOMS, NEW Office/Den Addition and 4 FULL BATHS, entails NEW tile and engineered hardwood flooring, crown moldings, custom built-ins, Hurricane Impact Windows and Doors, designer window treatments, etc. The sophisticated Kitchen features a large island seating area, beautiful hardwood cabinets, quartz countertops, premium stainless steel appliances including WOLF, KitchenAid, Etc. The extensive Owners’ Suite showcases herringbone pattern engineered hardwood floors, multiple walk-in closets with custom built-ins and an impressive primary bath adorned by a gorgeous chandelier and featuring separate vanities, oversized custom-tiled shower, soaking tub, separate water closet, plantation shutters, etc. With its private setting and ideal Southwestern Exposure, the Expansive screened lanai offers multiple covered areas with NEW outdoor kitchen and separate Bar seating area with adjacent Full pool bath, a wonderful Pebbletec, Heated, Saltwater Pool & Spa, and attractive pavered deck. 3-CAR GARAGE offers ample storage. The Oaks is a distinguished, 24hr guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS 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, Bocce, Basketball Court, Playground and more! 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. **Please Enjoy Viewing the 3D VIRTUAL TOUR and AERIAL VIDEO**

889 Macewen Drive, Osprey

$2,035,000

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

Virtually Staged. **BRILLIANTLY UPDATED, MOVE-IN READY, GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** offers an Ideal Southern-Exposure and View across the 3rd Fairway of the Interior, HERON GOLF COURSE. Situated on an Oversized 0.71 Acre Lot with Circular Driveway and manicured landscape, this Extensively Renovated Home offers 3 BEDROOMS + STUDY/DEN, 3 FULL BATHS, High Ceilings, Crown Moldings, Gas Fireplace, Engineered Hardwood Flooring, Spacious Kitchen with New QUARTZ Counters and Stainless Steel appliances including premium brands such as SUBZERO and KITCHENAID, 3-Car Garage, Etc. An Expansive Primary Bedroom Suite features multiple walk-in closets, dual vanities, soaking tub and custom-tiled shower. The Expansive screened lanai features a Heated Pool & Spa, Outdoor Kitchen and ample entertaining space in a private and serene setting. NEW FEATURES include ROOF, Hurricane Impact Windows & Doors, Flooring, Countertops, Appliances, Pool Cage, Newly Resurfaced Pool & Spa, newly Pavered driveway and pool deck, etc. The Oaks is a distinguished, 24hr guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS 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, Bocce, Basketball Court, Playground and more! 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.

600 Eagle Watch Lane, Osprey

$1,495,000

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

Experience the unparalleled charm and convenience of this golf course home in The Oaks Club, the country club community designed by noted Sarasota architect Bo MacEwen. 228 Saint James Park is an original Bo MacEwen design, is located on the leafy and quiet Saint James Park cul-de-sac, and directly overlooks the opening hole of the Heron golf course. This single-floor three-bedroom, two-and-a-half bath will captivate you from the moment you step inside with its open floor plan, high, coffered ceilings with extensive crown moldings, and generous French doors providing wonderful lighting, beautiful views to the lanai, swimming pool, spa, and the Heron golf course itself. 228 provides mahogany flooring in most areas, and a completely redesigned and updated kitchen with quartz countertops, Sub-Zero refrigerator, wine refrigerator, cooktop, microwave, two beverage-cooling drawers, center island, custom cabinetry, and walk-in pantry. The great room is perfect for entertaining and flows seamlessly onto the lanai that overlooks Heron #1. The split floor plan has ensuite sleeping and bath areas on each side of 228: the master suite on the north side of the home features a completely remodeled spa-like bath and soaking tub, separate glassed-in shower, stylish lighting, and a generous, custom walk-in closet. On the south side of 228 is the ensuite guest area with the spacious second bedroom and fully renovated guest bath. The third bedroom is on this south side of the home as well, and is currently being used as the residents’ office, which enjoys pleasant, direct views of Heron #1 also and direct access to the lanai and pool. Numerous details associated with this home a two-car garage with epoxy floor, storage areas, and refrigerator/freezer, French doors, plantation shutters, newer roof (2020), plantation shutters, hurricane shades, walled-in motor court, and new bay windows by Pella. Saint James Park is the residential area closest to the athletic facilities of The Oaks Club, so SJP residents can easily walk or bike to the tennis courts, pickleball courts, Well-Fit Center, or golf pro shop. Residents enjoy both casual and fine dining, as well as a social atmosphere that encourages all to stay engaged in all that The Oaks Club offers. For those electing golf memberships, the ability to play the two courses here is immediate….no waiting period! And The Oaks Club has been designated a Platinum Club of America and an Emerald Club, signifying its standing among the finest country clubs in Florida and the nation. Schedule a showing today!

228 Saint James Park, Osprey

$2,300,000

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

**BRILLIANTLY DESIGNED AND RENOVATED, CUSTOM GOLF COURSE ESTATE with SPECTACULAR WATER and GOLF COURSE VIEWS** is situated on the 8TH Green complex of the Interior HERON GOLF COURSE and is located on a tranquil, 0.59 Acre cul-de-sac lot behind the Secure Gates of The Oaks Country Club neighborhood. Featuring 4 Bedrooms PLUS Large Study/Den, 3 Full and 1 Half Baths, this Open Floorplan with Soaring Ceilings, Custom Built-Ins, Crown Moldings, Engineered Hardwood flooring and discerning architectural details throughout is ideal for entertaining both inside and out! The Impressive NEW Kitchen features Quartz Counters, Premium Stainless Steel appliances including Wolf and Subzero brands, and Large Island with seating area. The Expansive Primary Bedroom Suite entails a Bonus sitting area, multiple walk-in closets with custom built-ins and spacious bath with dual vanities, custom-tiled shower and large soaking tub. Oversized Guest Bedrooms in a private guest corridor are ideal for hosting your family and friends. Incredible Outdoor Entertaining area features a large, covered seating area and Heated Pool in an Expansive, Screened Lanai with an Ideal Southwestern Exposure. NEWer ROOF (2019), Hurricane Impact Windows & Doors (2020-2021), NEW Laundry Room and Much More! THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS 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, Bocce, Basketball Court, Playground and more! 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. **PLEASE ENJOY VIEWING THE 3D VIRTUAL TOUR and AERIAL VIDEO**

264 Saratoga Court, Osprey

$995,000

3 Beds ⋅ 2 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

Welcome to Emerald Woods, a desired cul-de-sac within The Oaks Preserve, and this private Lee Wetherington custom home that will check all the boxes, and more. Situated on one of the largest lots and surrounded by preserve for privacy, you’ll find essence and elegance as the color palette interplays with natural light, and the southern facing lanai and pool will be where you can enjoy the maintenance free lifestyle, and the quality of life second to none. Enter the foyer through 8’ insulated front doors with impact glass, and 12’ high ceilings with wide decorative crown molding. Designer exceptional interior and exterior details and finishes are completed and tastefully appointed. The kitchen offers custom 42” wood upper cabinetry with over and under cabinet lighting, granite countertops, a decorative tile backsplash, center island with base cabinetry, a pantry with rollout shelving, stainless appliances (2023), and a seamless glass aquarium window in the breakfast nook. The great room has 17” stone tile flooring, custom built-in cabinetry and a custom designed stone fireplace with electric logs. The open floor plan dining room has a hand painted tray ceiling, and a built in buffet with a granite top and 42” upper cabinets with glass inserts. A fantastic escape awaits when you walk out your sliding glass doors to the outdoor oasis that includes a newly resurfaced custom designed pool and spa with a waterfall feature and a new pool screen and cage with a panoramic view maximizing the enjoyment of the outdoor space. A dry bar/buffet makes entertaining outdoors so easy. The primary suite offers an extended office/owner’s retreat with a custom designed built in desk and cabinetry, handsome bamboo wood floors, two large walk-in closets with built-ins, a primary bath with new vanities, undermount sinks, and designer brass and chrome fixtures. The second light and bright guest suite has wood floors, a bay window with plantation shutters and an ensuite custom designed bath. Additional special features include a new roof (2023) new landscaping and sod, a paver brick driveway, and an oversized 2 car garage with tandem parking for a 3rd car and tons of storage and cabinetry. Experience the best in this move in ready home, and begin your lifestyle at The Oaks Country Club, with the best location in Sarasota County. Centrally located to all the beautiful beaches and offering two 18 hole championship golf courses, tennis, pickleball, croquet, fitness center, dining, and a wide variety of social options. The Oaks is a Platinum Club of America, an Elite Distinguished Club of The World, and best of all there is no waitlist for a golf or social membership! Don't wait to begin your terrific and exceptional lifestyle!

105 Turquoise Lane, Osprey

$765,000

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

**STUNNINGLY UPDATED CONDO with Breathtaking Water & Preserve Views that rival those of higher floors!** This LARGE, CORNER UNIT of nearly 2800sf features 3-Beds & 3 Full Baths PLUS Study/Den (or possible 4th Bedroom with Walk-In Closet) and 2 side-by-side Covered Parking Spaces near elevator, Etc. and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club neighborhood. As you emerge from your private elevator foyer entrance, you will be enthralled by the Stunning View of Little Sarasota Bay and the Gulf of Mexico. The brilliantly RENOVATED, Light and Bright interior boasts a spectacular Kitchen with large waterfall island with seating area, Quartz countertops and Newer Stainless-Steel appliances, while other premium features include Plantation and Hurricane Shutters, Luxury Vinyl Plank and tile flooring, Crown moldings, Updated bathrooms with Quartz counters, NEW HVAC (2025), etc. The Owner’s Bedroom Suite features a Walk-in Closet, Custom Tiled Shower, Soaking Tub and Dual Vanities. The Spacious Balcony offers an ideal western exposure for enjoying gorgeous sunsets! Includes Climate-controlled Storage unit. This MERIDIAN I Condo Tower boasts a New Roof (2024) and New Elevators (2025 – in progress). Meridian Condo residents enjoy private amenities including Heated Pool & Spa, Fitness and Outdoor Grill in addition to The Oaks Club’s main campus of amenities. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS 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, Bocce, Basketball Court, Playground and more! 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. **PLEASE ENJOY VIEWING the 3D VIRTUAL TOUR**

385 N Point Road Unit 404, Osprey

$1,500,000

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

This completely remodeled home in The Oaks Clubside, set on nearly an acre of mature, meticulously landscaped grounds, is pure perfection. Nestled behind the gates of The Oaks Clubside, this residence is a masterful blend of classic elegance and contemporary sophistication. Arriving at the property, you are greeted by a striking full-circle driveway—a graceful approach that not only enhances the home’s curb appeal but also provides abundant guest parking for social gatherings and celebrations with loved ones. Step through the double front doors, with leaded glass, and you will immediately be taken by the clean lines and modern elegance of this home. The floors throughout the main living area are wood-look tile, making for beauty as well as ease of maintenance. The numerous high ceilings, windows and doors make the entire interior open, light and airy. With three generously sized bedrooms, an office or den, and two and a half baths, the layout adapts effortlessly to a variety of needs. The open floor plan ensures that each room enjoys picturesque views of the private lot, blurring the boundaries between indoor comfort and the natural beauty outside. The open kitchen will delight any home chef with its high-end stainless steel appliances, wide expanse of quartz countertops, an abundance of cabinetry for storage and a breakfast bar. There is a cozy breakfast nook, with a gorgeous outdoor view, for causal meals, and a formal dining room. The master suite is a study in luxury. This bright, spacious retreat features an incredible bathroom with a sunken tub and huge separate shower. The entire outdoor space has been thoughtfully updated, with ample areas for lounging, dining, and entertaining. The inviting pool and spa beckon you to cool off on a sunny afternoon or unwind beneath the stars. The new sleek pool cage ensures you can enjoy the outdoors in comfort, with incredible views. This home boasts a host of recent upgrades designed to provide ultimate comfort and efficiency. Impact windows and doors offer storm protection and energy savings while letting in abundant light. A new roof adds to the peace of mind, ensuring years of worry-free living. Add to all this, a large laundry room, a big, clean garage, custom lighting, plantation shutters, a gorgeous fireplace and so much more, and you have discovered the perfect home for living ultimate country club lifestyle on the Gulf Coast. The Oaks, Sarasota’s premier golf and country club, has two championship golf courses, an outstanding tennis program, pickle ball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and offers a wide variety of dining, recreational and social options. Membership is required with homeownership.

462 E Macewen Drive, Osprey

$1,700,000

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

Large 4 bedroom, 4 bath home on over half an acre bordering the 7th fairway of the Heron Golf Course in the Oaks Clubside. Located in the heart of south Sarasota, The Oaks offers 2 championship golf courses, a world-class tennis facility, a state-of-the art wellness center and a wide variety of club amenities, including dining options and social offerings. Club membership is required with homeownership.

898 Macewen Drive, Osprey

$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

$1,197,000

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

Luxury Clubside Living at The Oaks – featuring Elegance and Comfort! Stunning Clubside residence in the upscale Oaks Club, offering the perfect blend of estate charm and modern luxury. Nestled among grand oak trees with partial lake and full golf course views, this beautifully upgraded home offers 3,321 sq ft of refined living space in one of Sarasota’s most exclusive communities. You’re welcomed by a grand entrance that sets the tone for this elegant home. The living room features a custom-built-in bar and three sets of French doors that open to the pool and patio, perfect for indoor-outdoor entertaining. A formal dining room offers a refined space for gatherings, while plantation shutters throughout add timeless style. The stunning kitchen has been completely upgraded with new cabinets and countertops, along with a new dishwasher and refrigerator, and opens seamlessly to the delightful breakfast and family room with its new fireplace wall. The first-floor owners' suite offers privacy and serenity with French doors to the pool area and a spa-inspired bathroom featuring a stone tub and marble finishes. Upstairs, you’ll find spacious guest bedrooms, each with their own brand-new en-suite bathrooms, ideal for family or visitors. Enjoy modern convenience with smart home features including automated lighting, locks, garage doors, and an irrigation system. Outside, the crystal-clear pool is enclosed by a brand-new pool cage, and there’s a convenient powder room just off the pool for guests. Additional highlights all windows replaced with Miami-Dade hurricane windows with lifetime warranty, new leaf filter system, a generous laundry room, an oversized two-car garage with a built-in storage system, and an updated garage floor. A complete list of upgrades since the current owner’s purchase is available upon request. Less than 3 miles from Pine View School. Membership in The Oaks Country Club is required, granting access to world-class amenities such as two championship golf courses, an elegant clubhouse with dining and social events, Har-Tru clay tennis courts and pickleball, a heated community pool, playground, and the state-of-the-art WellFit fitness center. The Oaks is proud to be a Platinum Club of America and holds a renowned 5-Star rating.

223 Saint James Park, 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

$1,850,000

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

This is your rare chance to claim a spectacular estate in Sarasota’s premier golf and country club community THE OAKS. This elegant home seamlessly blends timeless architecture with resort-style living. Beyond the private gates, step into over 4,000 square feet of refined interiors featuring dramatic ceilings, architectural columns, and panoramic views. The expansive layout includes 4 bedrooms, 5 bathrooms, formal and casual living spaces, and an executive Office/Den/Bourbon Tasting Room. The gourmet kitchen is perfectly equipped for culinary entertainment, with custom cabinetry, premium appliances, and a spacious island that flows into the family room. A luxurious owner’s suite provides a private sanctuary with jetted bath, 3 walk-in closets, and direct access to the pool terrace. Outdoors, your personal retreat awaits: a heated pool and spa, covered dining and lounge areas, separate firepit area, and tropical landscaping. Membership to The Oaks Country Club is mandatory. You can decide on a Social Membership or a Full Golf Equity Membership. Details attached. Club amenities include: 36 holes of golf, tennis, pickleball, croquet, 3 dining options, fitness, community pool/spa. Situated minutes from world-class beaches, fine dining, and downtown Sarasota’s cultural attractions. Make this your new home in Paradise! Crypto currency offers considered. Call for more information.

67 Sugar Mill Drive, Osprey

$2,400,000

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

**IMMACULATE ESTATE -- NEWER CONSTRUCTION (2014) -- METICULOUSLY MAINTAINED, MOVE-IN READY, CUSTOM Residence Designed by LAS CASITAS Architects** offers exceptional quality craftsmanship throughout and is located behind the Secure Gates of THE OAKS-BAYSIDE Country Club community. Situated on an Oversized 0.59 Acre Lot backing to a Tranquil, Coastal Preserve and boasting wonderful curb appeal with its manicured landscape, Circular driveway and Courtyard entryway, this Impressive Spanish-style residence features 3-BEDS plus DEN/STUDY (with built in Murphy Bed), 3 FULL and 1 HALF BATHS and a 3-CAR Garage. Premium features abound throughout this Light and Bright, Open Floorplan, including Wood and Marble flooring, Crown Moldings, Tray Ceilings, Custom Built-ins and much more! The sizeable Chef’s Kitchen is a Culinary Dream and features white solid wood cabinets, granite counters, large island with prep sink, counter seating area, premium appliance brands including Thermador, Bosch, etc. The expansive Primary Bedroom suite entails multiple walk-in closets, primary bath with dual vanities and large, custom-tiled shower. Enjoy the utmost in Florida, Outdoor Living in your expansive, screened lanai featuring Heated Saltwater Pool, Outdoor Kitchen, ample covered seating areas and stunning natural surroundings overlooking the Coastal, North Creek Preserve. This “Smart Home” entails Control4 Home Automation, Lutron lighting technology, whole-house water filtration and softener, NEW GENERATOR with 500GAL Propane Tank, Hurricane IMPACT Windows and Doors, 2 Tankless water heaters, etc. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS 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, Bocce, Basketball Court, Playground and more! 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**

230 Osprey Point Drive, Osprey

$2,327,000

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

**STUNNING, UPDATED and METICULOUSLY MAINTAINED GOLF COURSE ESTATE with INCREDIBLE OUTDOOR OASIS in the Highly Sought-After OAKS COUNTRY CLUB Community** is Situated on an Over ½ Acre Lot on a tranquil, cul de sac street with Ideal Southern-Exposure and Lake and Golf Course View across the 14TH Fairway of the Interior, HERON GOLF COURSE. Recent UPDATES include HURRICANE IMPACT WINDOWS and SLIDING DOORS (2023), NEW PANORAMIC POOL CAGE (2023), NEW GENERATOR (with 500 Gallon Propane Tank; 2023), 2 NEW HVAC SYSTEMS (2023), NEW ROOF (2018), FRESHLY PAINTED INTERIOR, EXTERIOR PAINT (2022) and Much More! With its delightful curb appeal and gorgeously manicured landscape, this residence offers 4 BEDROOMS, 3 FULL and 1 HALF BATHS plus OFFICE and additional Bonus STUDY/DEN. High Ceilings, Crown Moldings, Spacious Kitchen with Granite Counters and Stainless-Steel appliances, Travertine and Wood flooring, 3-Car Garage w/ spacious overhead storage, extra wide and newly pavered Driveway, and much more! An Expansive Primary Bedroom Suite features a Bonus sitting area, multiple walk-in closets, dual vanities, soaking tub and custom-tiled shower. Enjoy OUTDOOR LIVING at its FINEST with a remarkable Infinity Edge, Heated Pool & Spa, well-equipped Outdoor Kitchen with counter seating, multiple entertaining areas including an Impressive and Expansive, Paver Patio with FIRE PIT gathering area. Fenced DOG RUN on side of home with Exterior Lighting. A MUST SEE! THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS 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, Bocce, Basketball Court, Playground and more! 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**

654 Trenton Way, Osprey

$875,000

3 Beds ⋅ 2 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

**STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the Secure Gates of the Distinguished OAKS PRESERVE Neighborhood. Offering 3-Beds (or 2-Beds plus Den), 2-Baths and 2-Car Garage, Premium finishes abound throughout this home and include a Chef’s Kitchen, Tray Ceilings, Crown Moldings, Beautiful Luxury Vinyl Wood Plank, Plantation Shutters, an Oversized, Owner’s Bedroom Suite with Multiple walk-in closets and sitting area and much more! Enjoy the expansive and private outdoor living area in a screened lanai with wet bar and southern exposure overlooking a Garden and Tranquil Preserve. Mostly NEW Hurricane Impact Windows/Door. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS 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, Bocce, Basketball Court, Playground and more! 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.

293 Turquoise Lane, 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

$1,855,000

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

**IMPRESSIVE ESTATE WITH GOLF COURSE AND WATER VIEW in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an over 2/3 Acre, Serene Lot with Ideal Southwestern-Exposure and View across the 15TH Fairway of the interior, HERON GOLF COURSE. Recent UPDATES include NEW ROOF (2020), NEW HURRICANE IMPACT WINDOWS & SLIDING DOORS (2020), Etc. With its delightful curb appeal and manicured landscape, this Light and Bright residence offers 4 EN SUITE BEDROOMS + Study/Den, 4 FULL and 1 HALF BATHS, Soaring Ceilings, Crown Moldings, Gas Fireplace, spacious kitchen with Granite Counters and Stainless Steel appliances, 3-Car Garage w/ Large Circular Driveway, and much more! The Spacious Primary Bedroom Suite features multiple walk-in closets, dual vanities, soaking tub and custom-tiled shower. Ultimate enjoyment of the outdoors is made possible with an expansive screened lanai featuring a Pool & Spa, Outdoor Kitchen and ample entertaining space in a private and serene setting. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS 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, Bocce, Basketball Court, Playground and more! 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**

533 N Macewen Drive, Osprey

$2,100,000

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

**EXQUISITELY DESIGNED and BRILLIANTLY RENOVATED, CUSTOM GOLF COURSE ESTATE with SPECTACULAR WATER VIEW** is situated on the Interior HERON GOLF COURSE and is located on a tranquil, cul-de-sac street behind the Secure Gates of The Oaks Country Club neighborhood. Framed by stunning Grand Oaks, your approach will only be enhanced upon entering through the grand double doors and gazing out across the picturesque lake. Featuring 4 BEDROOMS (2 En Suite), 4 FULL and 1 HALF BATHS, this Open Floorplan with Soaring Ceilings, Custom Built-Ins, Crown Moldings and discerning architectural details throughout is ideal for entertaining both inside and out! The Impressive Kitchen features Granite Counters, Stainless Steel appliances, Large Island with sitting area, separate island wet bar, etc. The Expansive Primary Bedroom Suite entails a Bonus room (possible office/sitting/gym area), multiple walk-in closets with custom built-ins and spacious bath with dual vanities, tiled shower and large soaking tub. Oversized Guest Bedrooms in a private guest corridor are ideal for hosting your family and friends. Incredible Outdoor Entertaining area features an expansive Heated Pool, Extended Lanai and pool deck, Outdoor Kitchen, Full Pool Bath, pool storage and more! NEW(er) HVAC (2018), Hot Water Tank (2024), Plumbing, Flooring, Electrical, Hurricane Impact Windows & Doors, Screen Enclosure, etc. THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where amenities include Three Restaurants, Ballroom, Two 18-hole championship GOLF courses, award-winning RACQUETS 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, Bocce, Basketball Court, Playground and more! 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**

627 Eagle Watch Lane, Osprey

$1,450,000

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

Imagine how you’d like to live the ultimate Florida lifestyle. Your vision can become a reality in this 5 bedroom, 5.5 bath two story home in The Oaks Clubside. Currently unfurnished, you just need to pack your bags, bring your own style and make it your own. Set back on a cul-de-sac lot, with gorgeous lake and golf views, the floor plan offers flexibility for the space to be used by residents and guests in a number of ways. The first floor master suite offers plenty of room, including a poolside sitting area, and luxurious bath. One of the two guest suites is also on the first floor, with another on the second. All have walk-in closets. But before heading upstairs, take in the light, bright space on the ground level. The formal living room with fireplace is the perfect setting for cozy fall evenings. The island kitchen has granite countertops and stainless steel appliances. Meals prepared here can be enjoyed at the breakfast bar, breakfast nook or in the formal dining room. Step outside and enjoy the views over the expanse of the paver deck, pool and spa. Think about all the great outdoor entertaining you can do utilizing the outdoor kitchen with granite countertops. The second floor has an en-suite guest bedroom and offers two more bedrooms with a Jack-and-Jill bath. In addition, it has a gathering area that can be used for anything from a media room to a game room. The Oaks, Sarasota’s premier golf and country club, has two championship golf courses, an outstanding tennis program, pickle ball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and offers a wide variety of dining, recreational and social options. Membership is required with homeownership. INITIATION FEES GOING UP ON 2/1/2025. BUY NOW BEFORE THE INCREASE!

738 Macewen Drive, Osprey

$2,822,000

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

**STUNNINGLY UPDATED, CUSTOM GOLF COURSE ESTATE on a SPECTACULAR, Stand Alone, Beautifully Landscaped Lot with GOLF and LAKE VIEW ** is located behind the Secure Gates of The Oaks Country Club neighborhood and overlooks the Interior HERON COURSE. Featuring 5 BEDROOMS (including 4 En Suite), 4 FULL and 2 HALF BATHS, this Light and Bright, Open and Split floorplan is ideal for entertaining both inside and out with walls of windows and beautiful French Doors throughout! The Impressive NEW Kitchen features Quartz Counters, Stainless Steel appliances, Large Island with sitting area, a walk-in Pantry, etc. The new Tile (wood look) floors complement the abundant architectural details including wainscoting, ship lap, crown molding, many built-ins, and much more! The Expansive Primary Bedroom Suite entails a walk-in closet with custom built-ins and spacious bath with dual vanities, custom tiled shower and soaking tub while the 2nd story bedrooms feature private balconies PLUS a Bonus room and built-in desk area. Incredible, BRAND NEW Outdoor Entertaining area features a magnificent Pool & Spa with Fountains, travertine pool deck, Panoramic Screen Enclosure with LED lighting elements PLUS a Cabana style, covered entertaining area, Outdoor Kitchen and Pool Bath. NEW(er) ROOF (2018) and HVAC (2020-2021). THE OAKS 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, 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**

922 Macewen Drive, Osprey

$900,000

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

Welcome home to your sanctuary located behind the gates of the Exclusive Oaks Country Club. This corner lot in SAINT JAMES PARK is situated close to the CLUB, TENNIS, and all the amenities the community has to offer. As you approach the home the lush landscape and stunning trees capture your attention. Enter through the double front door to a serene view of the mature landscaping and view of the first green on the Eagle course behind. If you are looking for plenty of natural light, this home has it in abundance. The primary suite includes lots of closet space, views, direct access to the pool area and an impressive primary bath. There is a guest suite with bath and pocketing doors for added privacy. The third bedroom is just off the primary suite and includes a desk making it a very versatile room. The kitchen is open to the family room and includes a large island with plenty of space for cooking and casual dining. Additionally, there is a dinette space perfect for day-to-day dining. The family room includes a wood-burning fireplace perfect for the cool winter evenings as well as transom windows and sliders to the pool area. There is a whole home water softener installed. The roof was replaced in 2018. A/C is 2019 with an air scrubber installed in 2023. The pool includes a new pool pump and heater in 2022. Beautiful carpet was installed in portions of the home in 2023 with all other areas covered with travertine. Plantation shutters accent the many windows in the home. The Oaks Club is a private member-owned community and Requires a Golf or Social Membership of ALL residents. With over 1,000 acres and every amenity - private golf (2-18 hole courses), top-tier tennis, junior Olympic heated community pool, fitness, wellness and top-notch dining options. Our world-famous beaches are a short drive away and the south campus of Selby Gardens is just down the street. Nationally Top-ranked PINE VIEW school is close by. There is no shortage of shopping and dining options as well. Schedule your showing today! Make this your dream home in Paradise. SUBSTANCIAL PRICE IMPROVEMENT!

201 Saint James Park, Osprey

$3,000,000

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

New. Notable. No Waiting for your Dream Home! Rare opportunity for a luxury Florida lifestyle with this just completed John Cannon custom build. A coveted West of Trail location in The Oaks Bayside positions you in one of the area’s only country club neighborhoods on Sarasota Bay. With almost 3900sf on one level – and almost a half acre of private grounds – this is no cookie cutter home. If you crave “one-of-a-kind design” - you’ll delight in the details of this West Indes play on coastal style. A split plan with 3 ensuite bedrooms, 2 offices and a large den offer the ability to create the space you need – now and in the future. The moment you pass the iron entry doors, you’re instantly drawn to the vaulted ceilings with 7” wood beams and the feeling of freshness and sophistication only a modern design can convey. Your great room and kitchen transition seamlessly – complete with a linear fireplace and custom bar with wine fridge and ice maker. Truly a chef’s kitchen, entertain a crowd or intimate group with professional Monogram appliances, French-door oven, gas cooktop, 3 cm quartzite counters with mitered edges, massive island with tv views, butler’s pantry, hidden walk-in pantry, spice drawers, shaker cabinets & marble backsplash. A separate dining space offers views to the pool and grounds. No detail was left untouched in the owner’s suite – with an oversized light-filled bedroom with tray ceilings; dual closets that can only be described as massive; and a show-stopper bath with center walk-in shower, over the top soaking tub and TWO private patios for relaxing, reading or soaking up the sun! Desired but rarely found – a large, nearly half acre lot that offers privacy in a natural setting of mature oaks and native landscape. You’ll love the ample outdoor space for both sun and shade, ClearVue screen, PebbleTec saltwater pool and spa, custom fire bowls for evening ambiance, travertine pool deck, outdoor kitchen with gas grill, cooktop and storage. Oversized 3-car garage, circle drive and generator pad site & pre wire. Don’t forget the details you’d expect in a luxury home – impact windows and doors, porcelain tile floors throughout, 10 & 12 ft ceilings and pocketing sliders, LED lighting with custom fixtures and fans, solid core interior doors, tankless hot water heaters and surround sound speakers. All this in a nationally recognized club neighborhood offering not one – but TWO 18-hole golf courses, pickleball, 12 har-tru tennis courts, fitness center, community heated pool, children’s programs, on-site bar and dining as well as numerous member groups and activities. Mere minutes to the beaches, dining, shopping, the Legacy Trail, Pine View School for the Gifted and Historic Spanish Point. And just a short drive to all things Sarasota – downtown, arts and culture and fine dining. No waiting for membership and access to golf and all activities!

101 Sugar Mill Drive, Osprey

$765,000

3 Beds ⋅ 2 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code

BRAND NEW ROOF 2024! This beautiful 3 bed/2ba home is located in BISHOPS COURT in the Oaks Preserve. Once through the 24 hour guarded security gate you will be treated to rich fauna, streets lined with canopy trees, nature and tranquility. This is a MAINTENANCE FREE community, with its own private pool and clubhouse for only the Bishops Court residents to enjoy . The home was designed and built by the highly regarded Lee Wetherington. As soon as you enter the front door your eyes are drawn to the beautiful view of the Preserve that the home backs up to giving you a private oasis for which to enjoy. The architectural details of the home are not to be missed with 14ft trey ceilings making the open plan living area seem vast. The master bedroom is a spacious retreat with his and her walk in closets and a bonus area for an office/library or work out space. The master bath is light bright and airy, with a beautiful separate oversized soaking tub to relax in. The floor plan offers room and privacy for the home owner and their guests with the 2 other bedrooms sharing a bathroom on the other side. The attention to detail is shown with many upgrades, plantation shutters, pull out shelving throughout the home, brand new appliances, gas stove and updates throughout. It is move in ready. The Oaks Club is Sarasota's finest Golf and Country Club with numerous accolades. The amenities include 2 world class golf courses 12 Har Tru tennis courts, Croquet Well Fit Center, 4 Pickleball Courts, heated Junior Olympic sized pool. A brand new Grill room is almost completed and The Tavern and Blue Heron room offer fine dining in the evenings. There is an abundance of Clubs and Social activities something for everyone. The Oaks Club is a Platinum Club of America, Emerald Club of the World and Elite Distinguished Club of the World. You will live minutes from the Legacy Bike Trail, a short drive to the beautiful sandy beach on Siesta Key. Oscar Scherer State Park is just around the corner, cultural downtown Sarasota is 20 minutes away, not to mention all the other activities that Gulf Coast living has to offer. CLUB MEMBERSHIP IS AVAILABLE AND IS REQUIRED WITH PURCHASE. Paradise awaits. Bedroom Closet Type: Walk-in Closet (Primary Bedroom).

37 Bayhead Lane, Osprey

Browse All Oaks Properties for Sale

Oaks Real Estate & Homes

How much is your home worth?

How much is your home worth?