The Oaks Homes

Situated along the bay front, The Oaks offers a tropical paradise of stately elegance. It captures and maximizes the natural beauty of Florida with mature oaks that sway across winding, canopied streets. Exclusive and opulent, this 1000-acre area features homes in a variety of styles, including contemporary, Mediterranean, and Georgian.  The Oaks is comprised of three gated communities with 24-hour security. On Sarasota Bay, you will find almost 200 homes in The Oaks Bayside and The Preserve. Situated along the lush fairways of our 36-hole championship golf course is The Oaks Clubside, with more than 350 homes.

The Oaks offers homes for every lifestyle, including maintenance-free villas, town homes, high-rise condominiums, golf course homes, and waterfront executive homes—all designed with high-end amenities and distinctive luxury appointments. 

The Oaks Club is also the perfect community for those who love to enjoy all that the beautiful climate of Florida offers.  Take advantage of two championship golf courses; enjoy one of the 12 Har-Tru tennis courts; or take a swim in the junior Olympic pool.  If that’s not enough, you could enjoy the regulation croquet court, or simply indulge in an afternoon or evening with friends at the clubhouse.  Also a perfect location for avid boaters, residents have easy access from canal or bay front properties to a day of fun on the water.

With a long history that dates back to the 1900s, The Oaks was the original estate of Bertha Palmer, a Chicago socialite and businesswoman who purchased 80,000 acres in Sarasota. Her name and influence are still felt in the community today.  She chose 1,000 acres for her personal estate and dubbed it “The Oaks,” a name that became synonymous for the elegant lifestyle of Mrs. Palmer and of the distinguished guests she entertained in her home.

Today, The Oaks is a thriving community that offers a luxurious setting for Florida living, along with easy access to the thriving community life of Sarasota. Only 20 minutes from downtown Sarasota, The Oaks is also only 5 minutes from Sarasota Square Mall, along with a plethora of dining and shopping establishments, the Legacy Trail for cycling or walking, Oscar Sherer State Park, and much more.

The Oaks Homes for Sale

All Listings$100,000 - $200,000$200,000 - $300,000
$300,000 - $400,000$400,000 - $500,000$500,000 - $600,000
$600,000 - $700,000$700,000 - $800,000$800,000 - $900,000
$900,000 - $1,000,000Over $1,000,000
216 Properties Found. Showing Page 1 of 27
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Just Reduced! Motivated Seller. This Bayfront E...

$4,825,000
5 br, 7 ba, 6,045 ft² Oaks Days on Market: 229
Price:
$4,825,000
City:
Osprey
Beds:
5
Baths:
7
Subdivision:
Oaks
MLS® #:
A3949830
Days on Market:
229
Michael Saunders & Company
Provider:
Michael Saunders & Company

Just Reduced! Motivated Seller. This Bayfront Estate In The Prestigious Oaks Club Is Situated On ...

Osprey, FL Real Estate: Residential Property for Sale in OAKS

This Home Has It All! Location! Location! Gr...

$4,750,000
6 br, 7 ba, 8,973 ft² Oaks Days on Market: 183
Price:
$4,750,000
City:
Osprey
Beds:
6
Baths:
7
Subdivision:
Oaks
MLS® #:
A3952220
Days on Market:
183
Michael Saunders & Company
Provider:
Michael Saunders & Company

This Home Has It All! Location! Location! Grand Entrance To This Custom 3 Floors Estate Home S...

MLS®# A3952220: Osprey Residential Real Estate for Sale at 112 Osprey Point Dr in OAKS

Stunning Georgian Estate Home Meticulously Reno...

$4,400,000
5 br, 9 ba, 6,881 ft² Oaks Days on Market: 120
Price:
$4,400,000
City:
Osprey
Beds:
5
Baths:
9
Subdivision:
Oaks
MLS® #:
A3954912
Days on Market:
120
Michael Saunders & Company
Provider:
Michael Saunders & Company

Stunning Georgian Estate Home Meticulously Renovated And Maintained To Perfection. This Exquisit...

MLS®# A3954912: Osprey Residential Real Estate for Sale at 136 Osprey Point Dr in OAKS

Wow! Better Than New! Words Can Not Describe ...

$2,495,000
5 br, 7 ba, 8,531 ft² Oaks Days on Market: 173
Price:
$2,495,000
City:
Osprey
Beds:
5
Baths:
7
Subdivision:
Oaks
MLS® #:
A3952572
Days on Market:
173
Michael Saunders & Company
Provider:
Michael Saunders & Company

Wow! Better Than New! Words Can Not Describe The Incredible Ambiance Feel This Home Has To Offe...

MLS®# A3952572: Osprey Residential Real Estate for Sale at 95 Osprey Point Dr in OAKS

The Epitome Of Luxurious Living In A Coveted Lo...

$2,450,000
4 br, 5 ba, 5,758 ft² Oaks Days on Market: 106
Price:
$2,450,000
City:
Osprey
Beds:
4
Baths:
5
Subdivision:
Oaks
MLS® #:
A3955617
Days on Market:
106
Premier Sotheby's Intl. Realty
Provider:
Premier Sotheby's Intl. Realty

The Epitome Of Luxurious Living In A Coveted Location, This Grand Custom-designed Estate Home Sit...

MLS®# A3955617: Osprey Residential Real Estate for Sale at 324 Osprey Point Dr in OAKS

Elegance, Privacy And Beautiful Golf Views Comb...

$2,349,000
4 br, 6 ba, 7,842 ft² Oaks Days on Market: 128
Price:
$2,349,000
City:
Osprey
Beds:
4
Baths:
6
Subdivision:
Oaks
MLS® #:
A3954446
Days on Market:
128
Michael Saunders & Company
Provider:
Michael Saunders & Company

Elegance, Privacy And Beautiful Golf Views Combine In This Lavish Estate Located In An Exclusive ...

MLS®# A3954446: Osprey Residential Real Estate for Sale at 550 Dove Pointe Pt in OAKS

Elegant, Gracious, Inviting...just A Few Words ...

$2,250,000
5 br, 6 ba, 5,553 ft² Oaks Days on Market: 117
Price:
$2,250,000
City:
Osprey
Beds:
5
Baths:
6
Subdivision:
Oaks
MLS® #:
A3955058
Days on Market:
117
Premier Sotheby's Intl. Realty
Provider:
Premier Sotheby's Intl. Realty

Elegant, Gracious, Inviting...just A Few Words That Come To Mind As One Meanders Down The Winding...

MLS®# A3955058: Osprey Residential Real Estate for Sale at 285 Sugar Mill Dr in OAKS

This Exquisite Home Built By Baron Construction...

$1,749,000
4 br, 5 ba, 5,416 ft² Oaks Days on Market: 92
Price:
$1,749,000
City:
Osprey
Beds:
4
Baths:
5
Subdivision:
Oaks
MLS® #:
A3956327
Days on Market:
92
Michael Saunders & Company
Provider:
Michael Saunders & Company

This Exquisite Home Built By Baron Construction, On An Acre+ Lot, Offers A Classic Example Of The...

MLS®# A3956327: Osprey Residential Real Estate for Sale at 473 E Macewen Dr in OAKS
 

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All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Listing data comes from My Florida Regional MLS.

Listing information last updated on May 23rd, 2012 at 12:55pm EDT.