The Oaks Homes with Gated Amenities

Welcome to The Oaks, an exquisite gated community nestled in the heart of Sarasota, Florida. This stunning subdivision is not just a place to live; it’s a lifestyle choice that embodies luxury, tranquility, and a strong sense of community.

The Oaks is renowned for its beautifully designed homes that reflect a perfect blend of elegance and modern living. Each residence boasts spacious floor plans, high-end finishes, and lush landscaping, creating a picturesque setting that is both inviting and sophisticated. Whether you’re seeking a charming single-family home or a sprawling estate, The Oaks offers a diverse selection of properties to suit every taste and lifestyle.

One of the standout features of The Oaks is its gated amenities, providing residents with an added layer of security and peace of mind. The community is equipped with 24-hour security, ensuring a safe environment for families and individuals alike. Residents can enjoy a wealth of recreational activities, including access to a luxurious clubhouse, swimming pools, tennis courts, and scenic walking trails.

The Oaks is ideally situated, allowing residents to experience the best of Sarasota living. With its proximity to pristine beaches, world-class dining, and vibrant cultural attractions, residents can easily immerse themselves in the dynamic lifestyle that Sarasota has to offer.

In The Oaks, you’ll find not just a home, but a community where neighbors become friends, and every day feels like a retreat. Discover the charm and elegance of The Oaks—your dream home awaits!

Newest The Oaks Homes with Gated Amenities

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

75 Osprey Point Drive, Osprey $1,649,000

Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling opportunities currently ava...

4 Beds
4 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

156 Bishops Court Road, Osprey $1,289,000

One or more photo(s) has been virtually staged. Designed by renowned architect Frank Folsom Smith, this timeless residence is privately positioned on an expansive double ...

3 Beds
4 Baths
The Oaks SubDv.
34229 Zip Code

51 Mac Ewen Drive Unit 14, Osprey — 51 $285,000

This completely updated 595 sq ft second-floor condominium is located in the Windsor Lodge behind the gates of The Oaks. It features top-of-the-line finishes and is acces...

1 Beds
1 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

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