Oaks Homes with Gated Amenities

Oaks Homes with Gated Amenities

Welcome to Oaks, a captivating subdivision nestled in the heart of Sarasota County, Florida, between the charming communities of Osprey and Nokomis. This exquisite neighborhood is designed for those who appreciate the finer things in life, offering a perfect blend of luxury, comfort, and community spirit.

As you enter Oaks, you are greeted by beautifully landscaped grounds and the serene ambiance that this gated community provides. The subdivision boasts a variety of elegantly designed homes, each showcasing unique architectural styles that harmonize with the lush surroundings. From spacious single-family residences to sophisticated estates, there is something to suit every taste and lifestyle.

One of the standout features of Oaks is its commitment to security and privacy. The gated amenities ensure peace of mind for residents, allowing you to enjoy your home and the community without worry. The subdivision fosters a close-knit atmosphere, where neighbors become friends, and families thrive in a safe environment.

Beyond the gates, Oaks offers residents access to an array of top-notch amenities. Enjoy leisurely afternoons at the community pool, or stay active with the well-maintained walking trails and sports facilities. The clubhouse serves as a social hub, hosting events and gatherings that bring the community together.

Located just minutes from the stunning Gulf Coast beaches, vibrant shopping centers, and fine dining options, Oaks provides an ideal balance of tranquility and convenience. Discover your dream home in this exceptional community, where luxury living meets the beauty of nature. Welcome to Oaks—your perfect slice of paradise in Florida!

Newest Oaks Homes with Gated Amenities

$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, 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
$1,295,000
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
$1,495,000
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
$1,495,000
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
$4,790,000
4 Beds ⋅ 6 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
Lakefront living and elevated architecture come together at 101 Osprey Point Drive, a Bo MacEwen-designed estate privately positioned on nearly an acre within the gates of Sarasota’s prestigious Oaks Bayside community. Spanning more than 5,000 square feet across two of the community’s most desirable homesites with 150 feet of water frontage, the residence blends timeless architecture, exceptional entertaining spaces, and a tranquil resort-style setting surrounded by lush landscaping and sweeping water views. An oversized granite-tiled circular drive and stately double-door entrance create a memorable arrival, leading into interiors defined by soaring ceilings, white onyx flooring with marble inlays, handcrafted millwork, dramatic fireplaces, crystal chandeliers, and walls of French doors opening to the lakefront terrace and pool. Designed for both elegant entertaining and everyday comfort, the home offers a series of richly detailed gathering spaces including a formal living room with dual fireplaces, a lakefront dining room with custom built-ins, a domed-ceiling sitting room ideal for cocktails or conversation, and a custom bar and wine room with etched-glass cabinetry, stone countertops, and display shelving. The remodeled chef’s kitchen combines classic design with modern functionality, featuring UltraKraft cabinetry, custom soffit lighting, Corian countertops, a center island with breakfast bar, and premium appliances including a Sub-Zero refrigerator, Wolf gas cooktop, wall oven, warming drawer, microwave, dual KitchenAid dishwashers, and wine refrigerator. A butler’s pantry and sunlit breakfast nook overlooking the gardens further enhance the home’s livability. The primary suite serves as a private retreat with a spacious sitting area, custom closets, and a spa-inspired bathroom renovated in 2025. Three additional guest suites with updated baths provide comfort and flexibility, including a separate suite ideally positioned for extended-stay guests, live-in assistance, or multigenerational living. Outdoor living is centered around an open-air pool, expansive entertaining deck, and cabana framed by mature landscaping and manicured hedges, creating a private oasis with peaceful lake views. Additional updates include refinished hardwood flooring, updated guest baths, and a Daikin 5-ton HVAC system installed in 2022. Located within The Oaks Club, residents enjoy access to one of Sarasota’s premier private club communities, offering two championship golf courses, tennis and pickleball courts, croquet, a state-of-the-art fitness center and spa, multiple dining venues, and a private community dock on Little Sarasota Bay. Just moments from Sarasota waterfront dining, Siesta Key beaches, and Sarasota/Venice cultural attractions, this distinguished lakefront estate presents an exceptional opportunity within one of the Gulf Coast’s most established luxury communities.

101 Osprey Point Drive, Osprey
$749,000
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
$2,700,000
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
$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
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