The Oaks Homes & Real Estate

The Oaks Clubhouse

Browse all The Oaks neighborhood homes for sale and real estate in Sarasota, FL below! Behold, The Oaks Club - a golf enthusiast's paradise located in the city of Osprey in Sarasota County that features some of the most beautiful waterfront properties south of Sarasota! The Oaks Club is home to not one, but two championship golf courses; the Eagle Course and the Heron Course. To get information about the Oaks neighborhood properties for sale or to schedule a home showing or private home tour, call or email the DWELL real estate professionals in Sarasota, Florida today. Read More about Oaks real estate.

Homes for Sale at The Oaks Sarasota

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205 Sugar Mill Dr, Osprey $175,000

  • 0.40 Acres

Build Your Dream Home Behind The Gates Of The Oaks Bayside On This Tranquil Lot. There Is Ample Room To Build A Large Home On This Lakefront Lot With The Builder Of Your Choice With No Time Constraint For Building. Enjoy The Wonderful Country Club Lifestyle...

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133 Osprey Point Dr, Osprey $1,149,000

  • 4 Beds
  • 3.0 Baths
  • 4,099 SqFt
  • 0.48 Acres

The Oaks… Completely Remodeled Home Located In The Exclusive Gated Community Of The Oaks Bayside With A Private Awesome Pool With Rock Waterfall, Spa And Slide. Just Across The Street From Sarasota Bay. Recent Improvements Include New Bathrooms And New Kit...

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168 Coastal Hammock Ct, Osprey $1,910,000

  • 3 Beds
  • 4.0 Baths
  • 3,924 SqFt
  • 0.48 Acres

Bayfront In The Oaks. Custom Designed Walled Mediterranean Estate In Private Cul-de-sac Location With A 5 Stop Elevator. Gorgeous Views From Several Locations Showcasing The Gulf And The Bay. Very Livable Floor Plan With Expansive Master Suite Offering A Se...

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761 N Macewen Dr, Osprey $1,450,000

  • 4 Beds
  • 5.0 Baths
  • 5,032 SqFt
  • 0.64 Acres

This 4 Bedroom, 4.5 Bath Mediterranean Style Home In The Oaks Offers Every Luxury Feature You Can Imagine! What Do You Enjoy Doing At Home? Whatever It Is, You Can Do It Here With The Best Of Everything! At-home Chef? Your Breath Will Taken Away By The Gou...

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244 Osprey Point Dr, Osprey $1,299,459

  • 3 Beds
  • 3.0 Baths
  • 3,132 SqFt
  • 0.52 Acres

Under Construction. Gracious Living Awaits You In This New Construction Home Sited Amidst The Tree Lined Streets Of The Oaks Bayside. You’ll Enjoy The Privacy Of This Preserve Homesite That Backs To North Creek. The Ventalo Plan Offers A Stylish Open Layout...

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42 Osprey Point Dr, Osprey $1,311,875

  • 3 Beds
  • 3.0 Baths
  • 3,692 SqFt
  • 0.52 Acres

Under Construction: The Beauty Of The Oaks Bayside Awaits You In This New Construction Villa Serena Floorplan. Private Homesite Backs To Natural Woodlands And Eagle Preserve. Through The Gorgeous Iron & Glass Double-door Entry, You’ll Find A Spacious Single...

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285 Sugar Mill Dr, Osprey $2,150,000

  • 4 Beds
  • 6.0 Baths
  • 5,578 SqFt
  • 1.03 Acres

Set Gracefully Amidst Lush Landscaping In The Private Gated Community Of The Oaks Bayside, This Stunning Residence Embodies Style, Sophistication And Understated Elegance At Every Turn. Idyllically Positioned On One Acre, This Walled And Gated Lakefront Est...

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221 Osprey Point Dr, Osprey $1,595,000

  • 4 Beds
  • 6.0 Baths
  • 4,811 SqFt
  • 0.57 Acres

Located Amid The Elite Elegance Of The Oaks Bayside, This Extraordinary Home Presents A Caliber Of Quality Usually Only Reserved For Multi-million Dollar Estates. A Meticulous 2015 Renovation Of This 2007 Home Transformed This Property Into A Modern Yet Cla...

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803 Lytham Cir, Osprey $995,000

  • 4 Beds
  • 4.0 Baths
  • 3,703 SqFt
  • 0.52 Acres

Come Live The Florida Lifestyle The Way It Was Intended To Be In This Magnificent And Beautifully Designed Home, Perfectly Located Behind The Gates Of The Glamorous Club Side Oaks Community. Privacy, Comfortable Entertaining , Open Living Not To Mention El...

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854 Macewen Dr, Osprey $1,999,000

  • 4 Beds
  • 6.0 Baths
  • 9,081 SqFt
  • 0.78 Acres

Immerse Yourself In Luxury! One Of The Most Exquisite Estate Offerings Is Nestled Within The Oaks Most Distinguished Clubside Enclaves. This Incomparable Dream Unfolds Over 9,000 Square Feet Of Quality Craftsmanship Including Automated Smart Home Technol...

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226 Saint James Park, Osprey $497,500

  • 3 Beds
  • 3.0 Baths
  • 2,591 SqFt
  • 0.27 Acres

Stunning And Updated Design, With A New Open Kitchen, Family, And Dining Room Area With 11-foot Ceilings Overlooking The Golf Course And Lake. New Carpet, New Paint, And New Flooring! Closest Street And Location (within Walking Distance) To The Oaks Heated ...

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Selling or buying a home in The Oaks soon? Call DWELL Real Estate (941) 822-0708, your Sarasota, Florida real estate team. Our community of The Oaks REALTORS® team will help you navigate the housing market in The Oaks Sarasota, FL.

Homes Sold in The Oaks

A jewel on Florida’s peaceful Sun Coast, its celebrated social calendar and community life attracts members from all over the United States that reside in one of The Oak's three gated communities.

Looking for a smaller winter get-away, an investment property, or to relax in a prestigious fairway-side mansion? Oaks Club real estate is available in many price ranges and designs and is some of the best golf community real estate property available in the Sarasota area.

Just as with original art masterpieces, the opulent Oaks Country Club community just south of Sarasota has a fine pedigree. This area was established nearly a century ago; the original Oaks property was the home of Chicago socialite Bertha Honore Palmer (think Chicago's Palmer House Hotel), a world-renowned art patron and businesswoman. Mrs Palmer vacationed here and helped make the Sarasota area the popular winter resort destination that it still is today. The prestigious Oaks Country Club, site of Mrs. Palmer's former home, is the hub of social life in this community today. The Oaks Sarasota community offers the luxurious environment that one expects from a top-class facility. Not unlike Mrs. Palmer, residents of The Oaks have convenient access to the Gulf of Mexico, world-class golf and tennis, and a short drive to all of Sarasota's fantastic cultural offerings. The community has a wide choice of residences, from large bayfront estates to custom-designed condominiums. The Oaks Sarasota residents enjoy total privacy, elegance and Florida's natural beauty. Come experience this splendid community for yourself.

The Oaks Club Homes for Sale

There are three gated neighborhoods to choose from at The Oaks Club.

  • The Oaks Bayside features 197 homes sites with many homes directly on Little Sarasota Bay.
  • The Oaks Clubside features 358 estate sized home sites bordering The Oaks Club golf courses.
  • The Oaks Preserve features preserve home sites in a natural estuary. Meridian at The Oaks Preserve is a bay front condominium development within the preserve.

Oaks Real Estate Market

The Oaks Club Golf Courses

The Oaks Club has two – 18 hole par 72 courses, the Heron course and the Eagle course.

“Our two courses, the Eagle and the Heron, challenge highly skilled players, and yet remain playable for golfers of all skill levels.
Respectful of our pristine environment, our courses share habitat with eagles, egrets, sandhill cranes, turtles, blue herons, bobcats and other native species. These close encounters with nature’s vibrant flora and fauna greatly enhance—and inspire—the golfing experience.”

- The Oaks Club

The Oaks Club course statistics:

  • Eagle Golf Course yardage ranging from 5,022 to 7,003 yards, Sea Isle Supreme Paspalum grass from tee to green
  • Heron Golf Course yardage ranging from 4,986 to 6,695 yards
  • Five tee placements appeal for golfers of all skill levels
  • State-of-the-art practice facilities and fully-staffed locker rooms
  • An award-winning golf pro shop with extensive product offerings
  • Golf lessons and weekly clinics
  • Active men’s, women’s, and couple’s play, as well as numerous informal groups
  • Reciprocal arrangements with other local clubs during summer months

The Oaks Club Amenities

The Oaks Club features stellar amenities you would only expect from an organization of this caliber. The amenities include but are not limited to:

  • 34,00 foot community clubhouse
  • Heated Jr. Olympic swimming pool
  • 12 Har-Tru Tennis courts, 4 are lighted for night time play.
  • Tournament croquet court
  • The Grille Room and Bar: 19th hole bar and Grille
  • The Tavern: Adult gathering area with a bar
  • The Glen Room: The Oaks Club formal dining room
  • 24 hour gated and mobile

The Oaks Club Location

Conveniently located in in the city of Osprey, The Oaks Club is removed from all the congested traffic you typically encounter on Tamiami Trail (US-41), Fruitville, Bee Ridge and downtown Sarasota. Cool summer breezes from the Intracoastal Waterway provide great relief during the hotter summer months.

Location of The Oaks Subdivision


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Images of The Oaks

The Oaks Clubhouse

Aerial view of The Oaks

Overlooking Sarasota bay

Natural Trail

Areial view of Oak Clubhouse

Social room in the clubhouse

Library in the clubhouse

The Oaks dining room


The Oaks in Sarasota

The Oaks swimming pool

Bar in Oaks Clubhouse

grand staircase in Oaks clubhouse

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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 January 22nd, 2017 at 6:18am EST.