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The Oaks Real Estate

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The Oaks Real Estate

Welcome to The Oaks, a prestigious subdivision nestled in the heart of Sarasota County, FL. Located in the charming cities of Osprey and Nokomis, The Oaks offers a unique blend of luxury living and natural beauty.

As you drive through the tree-lined streets of The Oaks, you'll be captivated by the lush landscaping and well-manicured lawns that define this exclusive community. The Oaks is renowned for its upscale homes, featuring a variety of architectural styles that cater to the discerning buyer.

Residents of The Oaks enjoy a host of amenities, including a private golf club, tennis courts, swimming pools, and a clubhouse perfect for social gatherings and events. The community is also conveniently located near top-rated schools, shopping destinations, and pristine beaches, making it an ideal place to call home for families and retirees alike.

Whether you're looking for a peaceful retreat or a vibrant community to immerse yourself in, The Oaks offers the perfect blend of tranquility and convenience. Come discover why The Oaks is more than just a place to live – it's a lifestyle.

Newest Listings in The Oaks

916 Macewen Drive, Osprey image
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 image
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 image
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 image
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 image
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 Mac Ewen Drive Unit 14, Osprey image
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 image
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 image
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
410 Blue Garden Lane, Osprey image
410 Blue Garden Lane, Osprey $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
49 Osprey Point Drive, Osprey image
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 image
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 image
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

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