The Oaks Homes with Waterfront

Welcome to The Oaks, a stunning and serene subdivision nestled in the picturesque landscape of Osprey and Nokomis, Florida. This exclusive community is a hidden gem in Sarasota County, where luxury meets tranquility, and nature embraces modern living. The Oaks is renowned for its breathtaking waterfront homes that gracefully overlook shimmering lakes and lush greenery, offering residents a daily retreat into paradise.

As you explore The Oaks, you’ll discover a diverse selection of beautifully designed homes, each reflecting the elegance and charm that Florida living embodies. From sprawling estates to charming single-family residences, every property is thoughtfully crafted with high-end finishes and spacious layouts, perfect for families and individuals alike. The waterfront locations provide not only stunning views but also the opportunity for leisurely activities such as kayaking, fishing, or simply savoring the sunset from your private dock.

The community of The Oaks is more than just a collection of homes; it’s a lifestyle. Residents enjoy access to a range of amenities, including a clubhouse, tennis courts, and a sparkling swimming pool, all designed to foster a sense of community and well-being. With its prime location, The Oaks offers the perfect balance of seclusion and convenience, with nearby shopping, dining, and pristine Gulf Coast beaches just a short drive away.

Experience the enchanting charm of The Oaks, where every day feels like a vacation and your dream waterfront home awaits. Embrace the Florida lifestyle in this idyllic neighborhood, and make The Oaks your new haven.

Newest The Oaks Homes with Waterfront

$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

$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

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