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

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 - $1,000,000 Over $1,000,000
Sort by:
View Results by:

No listings were found that matched this criteria.

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

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

This 3 Bedroom, 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, Which You ...

Listings have been deleted from all results. Undo Last Delete or View All Deleted Listings

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...

Listings have been deleted from all results. Undo Last Delete or View All Deleted Listings

466 E Macewen Dr, Osprey $950,000

  • 4 Beds
  • 4.0 Baths
  • 3,742 SqFt
  • 0.61 Acres

As You Pull Up To The Circular Driveway Of This Custom 4 Bedroom, 4 Bath Home In The Oaks Clubside You Can Tell Immediately That It Will Offer Everything You Could Want In A Home. Open The Doors And Step Inside And Your Exceptions Will Not Only Be Met, They...

Listings have been deleted from all results. Undo Last Delete or View All Deleted Listings

490 E Macewen Dr, Osprey $775,000

  • 4 Beds
  • 4.0 Baths
  • 3,192 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 ...

Listings have been deleted from all results. Undo Last Delete or View All Deleted Listings

433 E Macewen Dr, Osprey $1,200,000

  • 4 Beds
  • 4.0 Baths
  • 4,012 SqFt
  • 0.61 Acres

Exquisite 4 Bedroom, 3.5 Bath Mediterranean With Custom Features Throughout. This Home Is A Tropical Oasis With Classic Elegance. Offering Every Detail Imaginable For The Finest In Florida Living. Features Include Whole Home Audio/video System, 6 Burner ...

Listings have been deleted from all results. Undo Last Delete or View All Deleted Listings

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...

Listings have been deleted from all results. Undo Last Delete or View All Deleted Listings

468 Walls Way, Osprey $1,995,000

  • 4 Beds
  • 5.0 Baths
  • 5,698 SqFt
  • 0.64 Acres

This Elegant Home Is Nestled On More Than A Half-acre Of Property Overlooking Tranquil Lake Waters Of The Oaks, Featuring An Array Of Beautiful Finishes Throughout. Majestic Décor Greets You At Every Turn, Including Cathedral Ceilings, A Grand Spiral Stairc...

Listings have been deleted from all results. Undo Last Delete or View All Deleted Listings

554 Dove Pointe, Osprey $979,000

  • 4 Beds
  • 4.0 Baths
  • 3,501 SqFt
  • 0.65 Acres

Idyllically Located In One Sarasota County’s Finest Communities, The Oaks Golf And Country Club, This Custom Built, 3500 Sq Ft, 4 Bedroom Plus Den, 3 ½ Bath Home, Has Quality Finishes And An Expansive Outdoor Living Area With A Summer Kitchen To Complete Y...

Listings have been deleted from all results. Undo Last Delete or View All Deleted Listings

427 Washington Ave, Osprey $199,000

  • 3 Beds
  • 2.0 Baths
  • 905 SqFt
  • 0.18 Acres

This Block Constructed 3/2 Bungalow Has Plenty Of Charm! Large Screened In Porch Is Ample Enough To Hang A Porch Swing And Have Table And Chairs For Morning Coffee Or Evening Cocktails. Beamed Ceilings And Walnut Wood Floors In The Living Room And Clay Sal...

Listings have been deleted from all results. Undo Last Delete or View All Deleted Listings

122 Marys Chapel Ct, Osprey $175,000

  • 0.45 Acres

A Dream Home In The Oaks Starts With The Perfect Piece Of Property! Just Under A Half Acre, This Wooded Lot Enjoys A Wonderful Location Within The Oaks Bayside. Situated On A Quiet Cul-de-sac, It Backs To Historic Spanish Point. A Great Opportunity For A...

Listings have been deleted from all results. Undo Last Delete or View All Deleted Listings

851 Macewen Dr, Osprey $700,000

  • 3 Beds
  • 5.0 Baths
  • 2,958 SqFt
  • 0.50 Acres

With 3 Bedrooms & 4.5 Bath This Is One Of The Smaller Houses In The Oaks Clubside By Square Footage. However, It Feels Unusually Large When Entering Its Central Room Through The Double Front Doors. With 12’ High Walls, Crown Moldings, Ceiling Wainscoting & ...

Listings have been deleted from all results. Undo Last Delete or View All Deleted Listings

464 Walls Way, Osprey $1,099,000

  • 3 Beds
  • 4.0 Baths
  • 4,826 SqFt
  • 0.65 Acres

Step Out Of The Boredom Of Predictable Floor Plans And Into The Elegance Of A Custom Designed Home That Will Excite And Delight With Originality, Quality And Presence. Situated On One Of The Most Desirable Cul De Sac Locations In The Heart Of The Oaks Club ...

Listings have been deleted from all results. Undo Last Delete or View All Deleted Listings

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


View Larger Map

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

Reviews for Oaks

0 Based on 0 Ratings
View all Community Ratings & Reviews

Your Rating *

How Do You Know?

Live/Lived Here Just Visited

About You

*Your email address will not be displayed

Your Review


Search Homes for sale in The Oaks Sarasota

The Oaks Real Estate Agent Contact

Can't find what you're looking for? Let me do the work for you. Fill out the form below and a detailed description of the type of property you're interested in and I'll send you everything currently available.

Your Contact Information

Please provide a valid email address.

Property Information

Moving Details

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 24th, 2017 at 4:23pm EDT.