The Oaks Homes For Sale in Sarasota

The Oaks Clubhouse

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.

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.

Homes For Sale in The Oaks

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$900,000 - $1,000,000 Over $1,000,000
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112 Osprey Point Dr, Osprey $4,449,000

  • 6 Beds
  • 7.0 Baths
  • 8,973 SqFt
  • 0.60 Acres

No Water Tease Here! Truly A Boater's Dream! This Grand Custom 3 Floor Home Sits On One Of The Premier Lots In Oaks Bayside. Enjoy Magical Full Waterview With Amazing Sunsets Either At Home Or In Your Boat Crewing On The Open Bay To The Gulf Of Mexico. ...

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136 Osprey Point Dr, Osprey $3,449,900

  • 7 Beds
  • 9.0 Baths
  • 8,843 SqFt
  • 0.67 Acres

Fantastic Opportunity To Own This Prestigious Home In The Oaks Bayside. You Will Be Immediately Impressed With The Georgian Style Of Architecture As You First Approach The Circular Driveway And The Lush Tropical Foliage. The Front Facade Of This Home Is Pic...

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931 Blue Heron Overlook, Osprey $2,499,000

  • 4 Beds
  • 7.0 Baths
  • 6,977 SqFt
  • 0.59 Acres

Located Clubside At The Oaks, This Distinguished Residence Is Sited At The End Of A Cul-de-sac Boasting Breathtaking Views Stretching All The Way To The Oaks Clubhouse And Strategically Located On The New Fry/straka (course Architects Of Erin Hill, Site Of ...

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285 Sugar Mill Dr, Osprey $2,100,000

  • 5 Beds
  • 6.0 Baths
  • 5,578 SqFt
  • 0.66 Acres

Grand And Impressive-yet Warm And Comfortable At The Same Time, This Private Walled Estate Exudes A Feeling Of Both Tranquility And Joy. Set In The Wooded Enclave Of The Oaks Bayside, You Arrive After Driving Down Canopied Sugar Mill Dr. The Property Cons...

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419 Walls Way, Osprey $1,845,000

  • 4 Beds
  • 5.0 Baths
  • 5,523 SqFt
  • 0.59 Acres

Prepare To Be Inspired At The Sight Of This Grand Colonial Revival Estate Home Sited Gracefully On Arguably One Of The Oaks' Premier Cul-de-sac Lots. Enjoy Unrivaled Sunrise, Sunset, Lake And Golf Course Views Of The New Fry- And Straka-designed (course Arc...

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497 Webbs Cv, Osprey $1,749,000

  • 6 Beds
  • 7.0 Baths
  • 6,341 SqFt
  • 0.45 Acres

Located In The Exclusive Gated Community Of The Oaks Bayside. Totally Remodeled Home With Too Many Improvements To List, Everything Is New Including; New Roof, Air Conditions, New Flooring, New Kitchens And Baths, New Pool, Lanai Screens, New Travertine Aro...

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478 Oriskany Ct, Osprey $1,679,000

  • 4 Beds
  • 7.0 Baths
  • 5,856 SqFt
  • 0.55 Acres

Closest Home To Brand New Construction You Will Find In The Oaks. New Roof, New Windows, All New Kitchen With Viking Professional Appliances, New Stone And Wood Flooring Throughout, All New Interior Doors, New Plumbing, New Second Story, New Pool Deck, Sur...

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340 Osprey Point Dr, Osprey $1,649,000

  • 5 Beds
  • 7.0 Baths
  • 6,001 SqFt
  • 0.78 Acres

Timeless Grandeur! This Exquisite Traditional Estate Was Designed To Perfection For Luxury Living With 5 Bedrooms And 5.2 Baths In The Highly Desirable Oaks Bayside. Volume Ceilings, Crown Molding And Architectural Details Are Evident Throughout The Prope...

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296 Osprey Point Dr, Osprey $1,599,000

  • 4 Beds
  • 6.0 Baths
  • 7,092 SqFt
  • 1.00 Acres

Featuring His And Hers Master Bedrooms And Bathrooms, This 4 Bedroom + Office, 5.5 Bath, 7,092 Sq Ft Home Has It All! You Need To Look No Further For The Home That Offers Space, Beauty, Comfort & Privacy! Travertine Marble Floors Gleam Throughout This Large...

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530 N Mac Ewen Dr, Osprey $1,365,000

  • 4 Beds
  • 6.0 Baths
  • 4,346 SqFt
  • 0.61 Acres

A Tastefully Understated Façade Gives Entry To Dramatic Style And Sophistication In This Recently Remodeled Estate Home Located In The Private Gated Community Of The Oaks. Expertly Renovated And Meticulously Maintained, This Home Showcases Stunning High-end...

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395 Sugar Mill Dr, Osprey $1,345,000

  • 4 Beds
  • 4.0 Baths
  • 4,351 SqFt
  • 0.40 Acres

Spectacular Is The Only Way To Describe This Custom Built Bo Macewen Home In The Oaks, Bayside. Every Inch Of The 4,351 Square Feet Of Living Space Offers Elegant Living. Quality Details Abound, From The Designer Fixtures To The Gourmet Kitchen; Brazilian C...

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370 Sugar Mill Dr, Osprey $1,299,000

  • 5 Beds
  • 6.0 Baths
  • 4,783 SqFt
  • 0.46 Acres

Detail, Privacy And Quality Capture The Spirit Of This Magnificent, Five-bedroom Residence, With An Elegance Befitting Of Its Peaceful Preserve Location In The Oaks Bayside. Custom-built By Baron, The Over 4,700 Sq. Ft. Of Living Area Exhibits Masterful Cra...

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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.

Homes Sold in The Oaks

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Photos 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

Map of the 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.

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Listing data comes from My Florida Regional MLS.

Listing information last updated on May 27th, 2016 at 1:43pm EDT.