Oaks Homes with Gated Community - Guard Community Features

Oaks Homes with Gated Community - Guard Community Features

Welcome to Oaks, a distinguished gated community nestled in the heart of Osprey and Nokomis, Florida. This exquisite subdivision offers an unparalleled blend of luxury, privacy, and natural beauty, making it the perfect place to call home.

As you drive through the majestic entrance of Oaks, you'll be greeted by lush landscaping and a sense of tranquility that sets the tone for this remarkable community. The 24-hour guard service ensures peace of mind, allowing residents to fully embrace the serene lifestyle that Oaks has to offer. With a variety of beautifully designed homes, each property showcases unique architectural styles, spacious layouts, and modern amenities, catering to the diverse needs of families, retirees, and everyone in between.

Oaks isn't just about stunning homes; it's also about fostering a vibrant community spirit. Residents enjoy access to an array of top-notch amenities, including a sparkling community pool, tennis courts, and scenic walking trails that wind through the picturesque surroundings. The community is also conveniently located near the pristine beaches of the Gulf Coast, world-class dining, and shopping options, ensuring that everything you need is just a stone's throw away.

Whether you're looking to enjoy a leisurely afternoon at the beach, a round of golf at nearby courses, or simply unwind in your beautiful backyard, Oaks offers an idyllic lifestyle that embodies the best of Florida living. Discover the charm and sophistication of Oaks, where your dream home awaits amidst a welcoming and secure community.

Newest Oaks Homes with Gated Community - Guard Community Features

$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
$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
$1,950,000
4 Beds ⋅ 6 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
**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
$3,640,000
4 Beds ⋅ 6 Baths ⋅ Oaks SubDv. ⋅ 34229 Zip Code
Virtually Staged. Set on a private cul-de-sac within The Oaks, this revitalized estate captures the essence of elegant Florida living. From the moment you enter, the home’s light-filled, open design and thoughtful updates make an immediate impression. The main living spaces flow effortlessly from the chef’s kitchen to expansive entertaining areas and out to the lanai, where golf course views frame the heated pool, spa, and outdoor kitchen. The first-floor primary suite is a true retreat, featuring high ceilings, multiple closets, and a flexible sitting area that can serve as a nursery, gym, or private office. Upstairs, guests enjoy their own wing complete with a loft, theater, and screened terrace—ideal for relaxing or hosting in style. A split four-car garage, custom finishes, and generous room throughout reflect the craftsmanship expected in one of Sarasota’s most distinguished country club communities. The Oaks offers 24-hour security, two championship golf courses, an acclaimed racquets program, fitness and wellness facilities, and fine dining—all just minutes from the beaches and top-rated schools. Experience this home for yourself—take the 3D virtual tour and book your private showing today.

854 Macewen Drive, 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
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