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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

3621 North Point Road Unit 403, Osprey image
3621 North Point Road Unit 403, Osprey — 3621 $700,000

Embrace an active lifestyle with comfort and luxury in this beautifully situated residence at Meridian at The Oaks Preserve. Located in Building 5, this lovely condo is j...

  • 3 Beds
  • 3 Baths
  • The Oaks SubDv.
  • 34229 Zip Code
402 Macewen Drive, Osprey image
402 Macewen Drive, Osprey $1,590,000

Located behind the gates of The Oaks Clubside and within close proximity to the clubhouse, this 3-bedroom plus office, 3.5-bath residence offers over 3,500 square feet of...

  • 3 Beds
  • 4 Baths
  • The Oaks SubDv.
  • 34229 Zip Code
141 Sugar Mill Drive, Osprey image
141 Sugar Mill Drive, Osprey $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 image
362 Macewen Drive, Osprey $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 image
2912 Boating Boulevard, Kissimmee $510,000 ▼

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

One or more photo(s) has been virtually staged. An expansive double lot, a quiet cul-de-sac setting and preserve views with no rear neighbors make this Bishops Court resi...

  • 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
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
1524 The Oaks Boulevard, Kissimmee image
1524 The Oaks Boulevard, Kissimmee $534,900 ▼

Positioned along the 13th hole of The Oaks National Golf Course in Kissimmee, this golf-front residence offers elegant interiors, updated systems and a layout designed fo...

  • 4 Beds
  • 3 Baths
  • The Oaks SubDv.
  • 34746 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

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