The Oaks Homes with Deed Restrictions Community Features

Welcome to The Oaks, a premier subdivision nestled in the heart of Florida, where tranquility meets modern living. This enchanting community is designed for those who appreciate the beauty of nature, combined with the convenience of contemporary amenities.

The Oaks is a thoughtfully planned neighborhood featuring a variety of stunning homes, each crafted with meticulous attention to detail. With deed restrictions in place, residents can enjoy peace of mind knowing that their community is upheld by high standards of aesthetics and maintenance, preserving the charm and integrity of the area for years to come.

As you stroll through the tree-lined streets, you’ll discover beautifully landscaped yards, inviting parks, and vibrant community spaces that foster a sense of belonging among neighbors. The Oaks is not just a place to live; it’s a lifestyle. Families and individuals alike will appreciate the array of community features, including playgrounds, walking trails, and picnic areas, perfect for enjoying the warm Florida sun.

Moreover, The Oaks is conveniently located near top-rated schools, shopping centers, and recreational facilities, ensuring that everything you need is just a stone's throw away. Whether you’re seeking a peaceful retreat or an active lifestyle, this community offers the best of both worlds.

Discover the charm of The Oaks today and envision your future in this idyllic Florida haven, where community, comfort, and convenience come together in perfect harmony. Your dream home awaits!

Newest The Oaks Homes with Deed Restrictions 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

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

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

6519 W Newberry Road Unit 204, Gainesville image

6519 W Newberry Road Unit 204, Gainesville — 200 $99,000 ▼

Attention Investors! Prime Location on Newberry Road Excellent opportunity in a highly desirable area—directly across from HCA Florida North Florida Hospital with easy a...

2 Beds
1 Baths
The Oaks SubDv.
32605 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

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