The Oaks Homes with Restaurant Community Features

The Oaks Homes with Restaurant Community Features

Welcome to The Oaks, a stunning subdivision nestled in the heart of Osprey and Nokomis, Florida, where luxury living meets the serene beauty of nature. This premier community in Sarasota County is designed for those who appreciate both comfort and elegance, offering an array of exquisite homes surrounded by lush landscapes and scenic views.

The Oaks boasts a selection of beautifully crafted residences, each reflecting the unique architectural charm that the region is known for. From sprawling estates to cozy villas, there’s a perfect home for everyone in this vibrant community. The meticulously maintained grounds provide a picturesque backdrop for outdoor activities, whether you’re enjoying a leisurely stroll, biking, or simply soaking in the Florida sunshine.

One of the standout features of The Oaks is its array of community amenities, including a delightful restaurant that serves as a social hub for residents. Imagine savoring delicious meals crafted from fresh, local ingredients, all while enjoying the company of neighbors and friends. This restaurant not only offers a culinary experience but also fosters a sense of community, where gatherings, events, and celebrations are a regular occurrence.

Residents of The Oaks enjoy access to a variety of recreational activities, including golf, tennis, and a sparkling pool, making it easy to stay active and engaged. With its prime location, you’re just a short drive away from the stunning beaches of the Gulf Coast, shopping, and cultural attractions.

Discover the charm and elegance of The Oaks, where your dream home awaits in a community that feels like a vacation every day. Come experience the lifestyle you’ve always desired!

Newest The Oaks Homes with Restaurant Community Features

97 Sugar Mill Drive, Osprey
$1,950,000
5 Beds ⋅ 6 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
Welcome to an exceptional estate in The Oaks Bayside, where timeless elegance meets modern luxury in one of Sarasota County’s most prestigious gated communities. Perfectly positioned on a private, lush homesite beneath a canopy of majestic oaks, this stunning 5-bedroom, 6-bath residence offers the ideal blend of space, sophistication, and serenity. Step inside to discover a thoughtfully designed floor plan with expansive living areas, soaring ceilings, and an abundance of natural light. At the heart of the home is a completely renovated chef’s kitchen, featuring high-end finishes, premium appliances, custom cabinetry, and a seamless flow into the main living and entertaining spaces, perfect for both everyday living and hosting guests in style. Each of the five spacious bedrooms offers comfort and privacy, while the six bathrooms provide ample convenience for family and guests. Recent updates include a brand-new roof, and renovated kitchen, offering peace of mind and long-term value for the next owner. Outdoor living is equally impressive, with tranquil surroundings that capture the essence of Florida living, ideal for relaxing, entertaining, or simply enjoying the natural beauty that defines The Oaks Bayside. Residents enjoy access to The Oaks Club, a private, member-owned country club offering championship golf, tennis, fitness, dining, and a vibrant social lifestyle. Conveniently located near top-rated schools, beaches, dining, and shopping, this home delivers the perfect balance of privacy and accessibility. Experience refined living in one of the area’s most sought after communities, this is more than a home, it’s a lifestyle.

97 Sugar Mill Drive, Osprey
51 Macewen Drive Unit 5, Osprey
$235,000
1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
Discover a rare opportunity to own a serene retreat in The Oaks, one of Sarasota’s most sought-after private golf and country club communities. This bright, beautifully updated ground-floor studio is offered fully turnkey furnished, making it ideal as a seasonal getaway, or income-producing rental. Thoughtfully designed for both comfort and functionality, the open-concept layout seamlessly blends the living and sleeping areas. The updated kitchenette features dishwasher, oven, stove, fridge, freezer, microwave, quartz countertops, complemented by a dining nook and a convenient workspace. The modern bathroom includes a huge walk-in shower. Take in peaceful water views and picturesque scenes of the 18th fairway on the Eagle Course right from your patio. Residents of Windsor Lodge enjoy exclusive access to their own private pool. Short-term rentals are permitted, offering flexibility and excellent investment potential. Membership to The Oaks Club, a private, member-owned community renowned for its exceptional lifestyle amenities, is mandatory. Enjoy two championship golf courses, twelve tennis- and four pickleball courts, croquet lawns, pool and a state-of-the-art fitness and WellFit center. The expansive clubhouse features three dining venues, banquet facilities, and a vibrant social calendar. Perfectly positioned just 15 minutes from Siesta Key Beach, this property combines luxury living with unbeatable convenience in one of Sarasota’s premier locations.

51 Macewen Drive Unit 5, Osprey
49 Osprey Point Drive, Osprey
$2,399,000
4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes, including newer impact windows, retractable window walls, a sleek tile roof, custom concrete flooring, and exquisite baths and fixtures to go along with the state-of-the-art kitchen, equipped with top-tier Wolf and Sub-Zero appliances. Soaring vaulted ceilings create an expansive, airy ambiance, while large windows frame stunning lake views, offering the perfect backdrop for the sparkling pool and expansive spa, complete with tranquil water features. With disappearing sliders throughout, the home can let the air and light flow easily from outside to in. Enjoy breathtaking sunsets from your private oasis or stroll a kayak or paddleboard to the nearby boat launch for effortless access to Sarasota Bay and the Gulf, thanks to the newly reopened Midnight Pass. Situated on a secluded .40-acre lot, this property offers a serene retreat, featuring a Zen garden surrounded by lush landscaping. Residents of The Oaks enjoy world-class amenities, including championship golf, fine dining, tennis, fitness, and swimming. At 49 Osprey Point Drive, every detail has been meticulously crafted for those who seek refined living and unparalleled elegance.

49 Osprey Point Drive, Osprey
852 Macewen Drive, Osprey
$2,395,000
3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
**CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and Wetbar, 3-CAR GARAGE, etc. Premium features abound including Crown moldings, Marble and wood floors, Coffered ceiling, Custom built-ins, a well-equipped kitchen with Granite countertops, Stainless Steel Appliances including KitchenAid and Fisher & Paykel, and much more! An Expansive Primary Bedroom Suite features a Bonus Room, Walk-In Closet, dual vanities, soaking tub and custom-tiled shower. Enjoy OUTDOOR LIVING at its FINEST in an Expansive, Screened Lanai with PEBBLETEC Pool & Spa and Outdoor Kitchen in a serene setting. ROOF (2015). 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**

852 Macewen Drive, Osprey
13 Bayhead Lane, Osprey
$769,000
3 Beds ⋅ 2 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
**IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANCE-FREE COMMUNITY** This residence boasts an open floor plan that is ideal for entertaining, along with a screened and spacious outdoor pool area that provides privacy and overlooks a nature preserve. Recent updates include a new kitchen, bathrooms, flooring, fans, a four-year-old roof, a newly pavered driveway, and hurricane-rated patio and bedroom doors. All living areas have wood floors or Italian porcelain tile. The kitchen features a gas stove, Waterworks faucet, quartz countertops, modern stainless appliances, and solid wood cabinetry. The breakfast nook adjacent to the kitchen has aquarium glass windows offering a view of the pool and foliage. The family room glass doors stack behind the wall, providing views of the pool and preserve, and they are hurricane-rated. The owner's suite includes two walk-in closets, a linen closet and space for a sitting area or office. Hurricane-rated glass doors overlook the pool. There is a separate study/office/bedroom with built-in wood cabinetry and space and wiring for a media room. The guest suite has an ensuite bath updated with Quartz counters and a vessel sink. Enjoy the utmost in outdoor living with a stunning, PebbleTec POOL with Travertine deck while there is ample space for a spa or additional seating within the spacious screened lanai. Connections for an outdoor kitchen are also available. A beautiful new pavered driveway adds that special curb appeal. In addition to the metal, roll down hurricane shutters, there is an electric hurricane protective screen spanning the lanai area to protect outdoor furniture. The extra deep two car garage affords additional storage options. A collection of unique bougainvillea and crepe myrtle rounds out the gardens. This lot is located outside the FEMA flood zone Bishops Court in The Oaks Preserve is a 24-hour guard-gated community with walking and biking paths. Additionally, there is a year-round heated community pool nearby. 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**

13 Bayhead Lane, Osprey
909 Macewen Drive, Osprey
$1,595,000
3 Beds ⋅ 4 Baths ⋅ The Oaks SubDv. ⋅ 34229 Zip Code
**STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an Over Half Acre Lot overlooking the 12th Fairway of the interior, HERON GOLF COURSE. With its delightful curb appeal and manicured landscape, this splendid residence offers 3 BEDROOMS + Spacious Executive Office/Study, 3 FULL and 1 HALF BATHS, High Ceilings, Crown Moldings, Gas Fireplace, spacious Kitchen with Granite Counters and Stainless Steel appliances, 2-Car Garage w/ Circular Driveway, and much more! An Expansive Primary Bedroom Suite features multiple walk-in closets and an Updated Primary Bathroom with dual vanities, soaking tub, custom-tiled shower and private outdoor shower. Ultimate enjoyment of the outdoors is made possible with an expansive screened lanai featuring a Large 45ft Pebble-Tec Pool & Spa, Outdoor Kitchen space (without appliances) and an abundant covered seating area. Recent UPDATES include Freshly Painted Interior (2024), NEW POOL CAGE (2023), NEW ROOF (2018), HVAC (2018), Pool Pump, 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**

909 Macewen Drive, Osprey
Start Your Search