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
86 Properties Found. Showing Page 1 of 11
View As: Thumbnails List Map
Sort by:

Welcome To Your Private And Exclusive Estate Ne...

$4,699,900
5 br, 5 ba, 8,057 ft² Oaks Days on Market: 233
Price:
$4,699,900
City:
Osprey
Beds:
5
Baths:
5
Subdivision:
Oaks
MLS® #:
A3983442
Days on Market:
233
Keller Williams On The Water
Provider:
Keller Williams On The Water

Welcome To Your Private And Exclusive Estate Nestled Amongst The Trees And Floral Tropical Fauna ...

Photo of Listing #A3983442

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

$4,350,000
6 br, 7 ba, 8,973 ft² Oaks Days on Market: 876
Price:
$4,350,000
City:
Osprey
Beds:
6
Baths:
7
Subdivision:
Oaks
MLS® #:
A3952220
Days on Market:
876
Michael Saunders & Company
Provider:
Michael Saunders & Company

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

Photo of Listing #A3952220

Come Live The Lifestyle Of Sheer Elegance On On...

$3,900,000
7 br, 9 ba, 8,843 ft² Oaks Days on Market: 482
Price:
$3,900,000
City:
Osprey
Beds:
7
Baths:
9
Subdivision:
Oaks
MLS® #:
A3970693
Days on Market:
482
Michael Saunders & Company
Provider:
Michael Saunders & Company

Come Live The Lifestyle Of Sheer Elegance On One Of The Premier Lots Of The Number 1 Country Club...

Photo of Listing #A3970693

Escape To The Comforts And Magnificence Of A Ne...

$3,499,000
4 br, 7 ba, 6,977 ft² Oaks Days on Market: 516
Price:
$3,499,000
City:
Osprey
Beds:
4
Baths:
7
Subdivision:
Oaks
MLS® #:
A3969034
Days on Market:
516
Michael Saunders & Company
Provider:
Michael Saunders & Company

Escape To The Comforts And Magnificence Of A Neiman Marcus-inspired Luxury Retreat Within The Oak...

Photo of Listing #A3969034

This Spectacular 8,500sf Manse Was Designed And...

$2,675,000
5 br, 7 ba, 8,531 ft² Oaks Days on Market: 55
Price:
$2,675,000
City:
Osprey
Beds:
5
Baths:
7
Subdivision:
Oaks
MLS® #:
A3993216
Days on Market:
55
Michael Saunders & Company
Provider:
Michael Saunders & Company

This Spectacular 8,500sf Manse Was Designed And Built By Famed Architect Bo Macewen. The Home Liv...

Photo of Listing #A3993216

Pre-construction. Your New Home Will Be Built I...

$2,500,000
5 br, 5 ba, 10,000 ft² Oaks Days on Market: 161
Price:
$2,500,000
City:
Osprey
Beds:
5
Baths:
5
Subdivision:
Oaks
MLS® #:
N5782363
Days on Market:
161
Sarasota Realty Assoc., Inc.
Provider:
Sarasota Realty Assoc., Inc.

Pre-construction. Your New Home Will Be Built In The Oaks Bayside. The Oaks Club Is An Exceptiona...

Photo of Listing #N5782363

Nestled On Nearly An Acre Of Lush Tropical Foli...

$2,200,000
5 br, 6 ba, 5,758 ft² Oaks Days on Market: 96
Price:
$2,200,000
City:
Osprey
Beds:
5
Baths:
6
Subdivision:
Oaks
MLS® #:
A3990549
Days on Market:
96
Premier Sotheby's Intl. Realty
Provider:
Premier Sotheby's Intl. Realty

Nestled On Nearly An Acre Of Lush Tropical Foliage Along The Banks Of North Creek Is This Extraor...

Photo of Listing #A3990549

Magnificently Sited On A Secluded Cul-de-sac Pr...

$1,995,000
4 br, 6 ba, 5,698 ft² Oaks 2 Phase 1 Days on Market: 41
Price:
$1,995,000
City:
Osprey
Beds:
4
Baths:
6
Subdivision:
Oaks 2 Phase 1
MLS® #:
A3994081
Days on Market:
41
Michael Saunders & Company
Provider:
Michael Saunders & Company

Magnificently Sited On A Secluded Cul-de-sac Providing Brilliant Golf Course And Lakefront Views,...

Photo of Listing #A3994081
 

Did you find your dream home? If not, please fill out the form below.
We'll do the search and send you all the homes available that match your criteria.

* Indicates a Required Field.

Your Contact Information
Property Information
Moving Details

Back to Top

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 April 16th, 2014 at 1:45am EDT.