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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931 Blue Heron Overlook, Osprey $3,100,000

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

Experience Life In One Of Florida’s Finest Country Clubs, The Oaks, From This Exquisitely Crafted Estate Home. Strategically Positioned To Overlook The Signature Heron Golf Course, This Extraordinary Residence Presents Over 6,900 Sq. Ft. Of Space In Which T...

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51 Mac Ewen Dr #7, Osprey $119,000

  • 1 Beds
  • 1.0 Baths
  • 595 SqFt

Fore...! Enjoy Views Of The Clubhouse And Hole #18 On The Eagles Course As You Relax In Your Fully Equipped Efficiency At Windsor Lodge At The Oaks. This Unit Has Been Completely Updated, Optimizing All 595 Sq Ft. Of Space. Boasting Of Modern, Day-to-day ...

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95 Osprey Point Dr, Osprey $2,250,000

  • 5 Beds
  • 6.0 Baths
  • 7,500 SqFt
  • 0.74 Acres

French Chateaux With Guest House And 4+ (tandum) Car Garage In The Oaks Bayside. This Incredible Bo Macewen Designed Masterpiece Was Finished In 1997 And Major Renovations Were Done In 2001. As You Enter The Main House You Are Met With A Spectacular Wooden ...

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395 Sugar Mill Dr, Osprey $1,277,000

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

The " Secret Garden Home" Is Located Within The Exclusive Oaks Bayside. This Time Honored Custom Home Affords The Discriminating Buyer The Highest Quality For Those Wanting No Detail Overlooked In 4,351 Square Feet Of Elegant Living. This Home Has It All: B...

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677 Trenton Way, Osprey $1,100,000

  • 3 Beds
  • 5.0 Baths
  • 5,045 SqFt
  • 0.67 Acres

When You Look Up Light And Bright In The Dictionary There Is A Photo Of This Home! A Huge Circular Drive Leads To The Front Of This Majestic Home With A 20+ Foot Columned Entry With Leaded Glass Doors And A Large Curved Transom. As You Enter The Home You Ar...

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202 Saint James Pkwy, Osprey $675,000

  • 2 Beds
  • 3.0 Baths
  • 2,541 SqFt

Welcome To A Lovely Oaks Classic, A Home of Epic Tradition!  Quality Of Life In A Loving, Wonderfully Livable Home.  Must See...  double Entry Doors Open To Formal, Spacious Living Room Overlooking Pool.  Entertain! Family Rm Has Wet Bar & Fridge.  Neutral...

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361 Macewen Dr, Osprey $899,000

  • 3 Beds
  • 3.0 Baths
  • 3,255 SqFt
  • 0.54 Acres

Oaks Clubside-golf Course Views From This Outstanding Maintained Home With Quality Upgrades Through-out! Fabulous Curb Appeal W/circle Drive, Stone Accents, Flag Pole & Fountain. Enter The Open Foyer To View The Gorgeous Pool/spa W/spillover & Fountains. Go...

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84 Osprey Point Dr, Osprey $175,000

  • 0.30 Acres

Best Priced Preserve Lot In The Oaks Bayside. Exceptional Opportunity For You To Build Your Dream Home In The Gated And Exclusive Oaks Preserve. The Oaks Club Is A Mandatory Membership Country Club! With Fabulous Amenities Including Two Championship Styl...

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431 E Macewen Dr, Osprey $1,100,000

  • 3 Beds
  • 4.0 Baths
  • 4,184 SqFt
  • 0.63 Acres

This 3 Bedroom Plus Office, 4 Bath Home Is A Former Tivoli Model. Open And Airy, It Features Large, Spacious Rooms. The Living Room, Dining Room, And Family Room Have "disappearing" Sliders That Pocket Behind The Wall Opening Up The Whole Area To The Lanai...

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426 Walls Way, Osprey $1,050,000

  • 3 Beds
  • 4.0 Baths
  • 4,034 SqFt
  • 0.51 Acres

Too Hip To Be Square. This 3 Bedroom, 4 Bath Home In The Oaks Clubside Has A Cachet Of Cool. The Open Floor Design With Eclectic Finishes And Appointments Makes This Unique Space The Ideal Place For Every Way You Want To Live The Country Club Lifestyle. W...

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490 E Macewen Dr, Osprey $775,000

  • 4 Beds
  • 4.0 Baths
  • 3,372 SqFt
  • 0.70 Acres

Gorgeous Custom Built 4 Bedroom 4 Bath Toll Brothers Home Overlooking The Eagle Course. As You Walk In You Are Immediately Greeted By High Ceilings, And A Bright Open Floor Plan That Gives You Views Over The Pool And Out To The Golf Course From Most Rooms ...

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34 Osprey Point Drive, Osprey $1,099,995

  • 3 Beds
  • 4.0 Baths
  • 4,515 SqFt
  • 0.35 Acres

This Gracious French-provincial-inspired House Teams With Elegance And Custom Details Including Coffered Ceilings, Paneled Walls, And Hand-made Solid-wood Cabinets. The Oversized Living Room With Gas Fireplace Offers Soaring Ceilings And A Graceful Entrance...

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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 August 19th, 2017 at 5:34pm EDT.