The Oaks Homes with Waterfront

Welcome to The Oaks, a stunning subdivision nestled in the heart of Sarasota County, where the charm of Osprey and Nokomis meets the serene beauty of waterfront living. This exclusive community is a haven for those seeking a harmonious blend of luxury and nature, offering an idyllic lifestyle that is as vibrant as it is tranquil.

The Oaks boasts an array of exquisite homes, many of which feature breathtaking waterfront views. Imagine waking up to the gentle lapping of water against the shore, with stunning sunrises painting the sky in hues of orange and pink. These beautifully designed residences are crafted for comfort and elegance, with spacious layouts that seamlessly integrate indoor and outdoor living. Whether you’re entertaining guests on your patio or enjoying a quiet evening by the water, every moment here feels special.

Beyond the stunning homes, The Oaks offers a wealth of amenities that enhance the community experience. Residents can enjoy lush landscapes, walking trails, and direct access to the sparkling waters of Florida’s Gulf Coast. The nearby beaches, parks, and recreational facilities provide endless opportunities for outdoor activities, from boating and fishing to hiking and biking.

Living in The Oaks means embracing a lifestyle that celebrates both sophistication and relaxation. With its prime location in Osprey/Nokomis, you’re just a short drive away from the vibrant arts and culture of Sarasota, world-class dining, and shopping. Discover your dream home in The Oaks, where every day feels like a vacation!

Newest The Oaks Homes with Waterfront

$235,000

1 Beds ⋅ 1 Baths ⋅ The Oaks SubDv.

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/Nokomis

$2,399,000

4 Beds ⋅ 4 Baths ⋅ The Oaks SubDv.

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/Nokomis

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