The Oaks Homes with Gated Community - Guard Community Features

Welcome to The Oaks, a picturesque gated community nestled in the heart of Osprey, Florida, within Sarasota County. This stunning subdivision is more than just a place to call home; it embodies a lifestyle of luxury, tranquility, and security.

The Oaks is renowned for its beautifully designed homes that seamlessly blend elegance with comfort. Each residence is thoughtfully crafted, featuring spacious floor plans, high-end finishes, and breathtaking views of lush landscapes and serene waterways. Whether you're seeking a cozy retreat or a grand estate, The Oaks offers a diverse selection of properties to suit your lifestyle.

One of the standout features of The Oaks is its exclusive guard-gated entrance, ensuring peace of mind for all residents. The community is designed to foster a sense of security and privacy, allowing you to enjoy your home and surroundings without worry.

Beyond the gates, residents can indulge in an array of amenities that enhance the living experience. The Oaks boasts a stunning clubhouse, complete with a fitness center, swimming pool, and social spaces perfect for entertaining family and friends. For those who enjoy an active lifestyle, the community features beautifully maintained tennis courts and scenic walking trails, ideal for morning jogs or evening strolls.

Located just minutes from the beautiful beaches of Nokomis and the vibrant cultural scene of Sarasota, The Oaks offers the perfect balance of serene living and convenient access to shopping, dining, and entertainment. Experience the charm and allure of The Oaks – a community where luxury meets lifestyle in a truly remarkable setting.

Newest The Oaks Homes with Gated Community - Guard Community Features

916 Macewen Drive, Osprey $1,900,000

Virtually Staged. A rare canvas of luxury, positioned on a lush double lot within the sought-after, gated community of The Oaks, in Osprey, adjacent to stunning Sarasota,...

5 Beds
8 Baths
The Oaks SubDv.
34229 Zip Code

101 Osprey Point Drive, Osprey $4,790,000

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 o...

4 Beds
6 Baths
The Oaks SubDv.
34229 Zip Code

97 Sugar Mill Drive, Osprey $1,950,000

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. Perfectl...

5 Beds
6 Baths
The Oaks SubDv.
34229 Zip Code

51 Macewen Drive Unit 5, Osprey — Windsor Lodge $235,000 ▼

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 u...

1 Beds
1 Baths
The Oaks SubDv.
34229 Zip Code

480 Oriskany Court, Osprey — The Oaks Clubside $1,500,000 ▼

Welcome to 480 Oriskany Court...Tucked away on a quiet street within the prestigious Oaks Club in Osprey, Fl; This elegant residence overlooks the fairway of the Heron 14...

3 Beds
4 Baths
The Oaks SubDv.
34229 Zip Code

433 E Macewen Drive, Osprey $2,189,000 ▼

**EXPERIENCE TIMELESS ELEGANCE AND EXCEPTIONAL CRAFTSMANSHIP** in this impeccably maintained Arthur Rutenberg custom residence, perfectly positioned on a private 0.61-acr...

4 Beds
4 Baths
The Oaks SubDv.
34229 Zip Code

49 Osprey Point Drive, Osprey $2,399,000 ▼

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 ho...

4 Beds
4 Baths
The Oaks SubDv.
34229 Zip Code

21 Bayhead Lane, Osprey $789,000 ▼

Looking for a home you can truly fall in love with? Your search ends here. This thoughtfully updated, impeccably maintained 3 bedroom, 2 bath residence in The Oaks Preser...

3 Beds
2 Baths
The Oaks SubDv.
34229 Zip Code

852 Macewen Drive, Osprey $2,395,000 ▼

**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 Vi...

3 Beds
4 Baths
The Oaks SubDv.
34229 Zip Code

13 Bayhead Lane, Osprey $799,000 ▼

**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 en...

3 Beds
2 Baths
The Oaks SubDv.
34229 Zip Code

909 Macewen Drive, Osprey $1,595,000 ▼

**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, HER...

3 Beds
4 Baths
The Oaks SubDv.
34229 Zip Code