The Oaks Homes for Sale

Welcome to The Oaks, a stunning subdivision nestled in the heart of Florida, where luxury meets tranquility. This premier community is designed for those who appreciate the finer things in life, offering an idyllic blend of natural beauty and modern convenience. With its lush landscaping, serene lakes, and winding walking trails, The Oaks is a sanctuary that invites you to unwind and enjoy the Florida sunshine.

The homes for sale in The Oaks are nothing short of extraordinary. Ranging from elegant single-family residences to spacious townhomes, each property boasts unique architectural styles and high-end finishes. You’ll find open floor plans that seamlessly connect living spaces, gourmet kitchens equipped with top-of-the-line appliances, and expansive outdoor areas perfect for entertaining or simply soaking in the picturesque surroundings. Many homes also feature luxurious amenities such as private pools, home offices, and energy-efficient designs, tailored to meet the needs of modern families.

Life in The Oaks is not just about the homes; it's about the vibrant community. Residents enjoy access to exclusive amenities, including a sparkling community pool, fitness center, and beautifully maintained parks. The subdivision is conveniently located near premier shopping, dining, and entertainment options, ensuring that everything you need is just a stone's throw away.

Whether you’re seeking a permanent residence or a seasonal retreat, The Oaks offers a lifestyle that combines elegance, comfort, and a strong sense of community. Explore the available homes for sale today and discover your dream home in this enchanting Florida oasis!

Newest The Oaks Homes for Sale

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

8731 Nw 127th Place, Chiefland $259,900 ▼

THIS property has it ALL! A solid concrete block home , 3 bedrooms / 2 bathrooms with a Den on 1 full acre in the quiet countryside with NO restrictions, minutes to the M...

3 Beds
2 Baths
The Oaks SubDv.
32626 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

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