The Oaks Real Estate

Welcome to The Oaks, a picturesque subdivision nestled in the heart of Florida, where tranquility meets modern living. This charming community is known for its lush landscapes, serene surroundings, and a vibrant atmosphere that appeals to families, retirees, and everyone in between.

As you stroll through the tree-lined streets of The Oaks, you’ll be captivated by the stunning architectural designs of the homes, each reflecting a unique blend of elegance and comfort. The community boasts a variety of housing options, from spacious single-family homes to cozy townhouses, ensuring there’s something for everyone. With well-maintained yards and vibrant gardens, each property exudes curb appeal and a sense of pride in ownership.

The Oaks is more than just a collection of beautiful homes; it’s a lifestyle. Residents enjoy access to a wealth of amenities, including a sparkling community pool, tennis courts, and playgrounds, perfect for family gatherings or leisurely afternoons. The community also hosts regular events, fostering a strong sense of camaraderie among neighbors, making it easy to forge lasting friendships.

Conveniently located near major highways, The Oaks offers easy access to nearby shopping centers, dining options, and recreational activities. Whether you’re exploring the beautiful beaches of Florida’s coast or enjoying a day at the local parks, adventure is just around the corner.

Discover the charm of The Oaks, where a vibrant community, beautiful homes, and an enviable lifestyle await you. Come experience the best of Florida living in this delightful subdivision!

Newest Listings in The Oaks

141 Sugar Mill Drive, Osprey/Nokomis image

141 Sugar Mill Drive, Osprey/Nokomis $1,700,000

Custom built by Emerald Homes, this beautifully updated 3 bedroom + bonus room, 3 bath residence, offers a bright, inviting layout with generous living spaces and thought...

3 Beds
3 Baths
The Oaks SubDv.
34229 Zip Code

362 Macewen Drive, Osprey/Nokomis $2,175,000

Experience luxury living in this beautifully appointed traditional home featuring 4 bedrooms, 3.5 bathrooms, and a dedicated office. The formal living room offers a firep...

4 Beds
4 Baths
The Oaks SubDv.
34229 Zip Code

2912 Boating Boulevard, Kissimmee $540,000 ▼

Virtually Staged. Welcome to this beautifully renovated home offering the perfect blend of luxury, comfort, and resort-style living! This move-in ready home features a br...

4 Beds
2 Baths
The Oaks SubDv.
34746 Zip Code

916 Macewen Drive, Osprey/Nokomis $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

6519 W Newberry Road Unit 108, Gainesville image

6519 W Newberry Road Unit 108, Gainesville — 100 $114,900

Fully updated 2 bed 2 bath in The Oaks. Great location near the University of Florida, Santa Fe College, and walking distance to North Florida Hospital. This second floor...

2 Beds
2 Baths
The Oaks SubDv.
32607 Zip Code

75 Osprey Point Drive, Osprey/Nokomis image

75 Osprey Point Drive, Osprey/Nokomis $1,595,000 ▼

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

156 Bishops Court Road, Osprey/Nokomis image

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

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

3 Beds
4 Baths
The Oaks SubDv.
34229 Zip Code

97 Sugar Mill Drive, Osprey/Nokomis image

97 Sugar Mill Drive, Osprey/Nokomis $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/Nokomis image

51 Mac Ewen Drive Unit 14, Osprey/Nokomis — 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/Nokomis image

51 Macewen Drive Unit 5, Osprey/Nokomis — 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

410 Blue Garden Lane, Osprey/Nokomis image

410 Blue Garden Lane, Osprey/Nokomis $699,000

Exceptional opportunity to build your dream estate in The Oaks, one of South Sarasota’s most prestigious gated golf and country club communities. Situated on a rare cul-d...

The Oaks SubDv.
34229 Zip Code