The Oaks Club

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Overview

The Oaks Golf & Country Club is 1000 acre development featuring two private 18-hole championship golf courses. The development is situated on both the east and west sides of US 41 in Osprey, Florida just 12 miles south of downtown Sarasota. Amenities include the private equity country club, guest lodge, 14 Har-Tru tennis courts, croquet court, 34,000 square foot Georgian-style clubhouse, fitness center, junior Olympic pool and an active social calendar.

Below are all of the homes for sale in the Oaks Club neighborhood in Osprey Florida. All real estate listings are updated daily from the Multiple Listing Service (MLS). To learn more about any of these properties or receive email updates when new listings hit the market, simply give us a call at 941-923-7777 or send us an email. We are here to help!

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MLS® Listing Statistics

Total Listings: 20
Average Price: $1,956,900
Highest Price: $4,195,000
Lowest Price: $469,000
Average Size: 4,047 ft²
Average Price Per Square Foot: $477 per ft²

Explore Other Sarasota Golf Homes Communities

Homes for Sale in the Oaks

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Image 0: A4627698

854 Macewen Drive, OSPREY, FL - $4,195,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 9,081 SQFT
  • 215 DOM
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One Or More Photo(s) Has Been Virtually Staged. **newly Renovated, Spacious, Golf Course Estate** Boasts Over 9,000sf And Is Situated On A Prominent, Private Cul De Sac Lot Of Over 3/4 Acres. Expansive Room Abounds In This Light And Bright Open Fl...

Image 1: O6305818

112 Osprey Point Drive, OSPREY, FL - $3,900,000

Residential, Single Family Residence
  • 4 Beds
  • 6 Baths
  • 8,635 SQFT
  • 46 DOM
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Premier Waterfront Opportunity In The Oaks Bayside This Grand Estate Home, Perfectly Positioned On A Rarely Available Direct Waterfront Lot In The Exclusive, Gated Oaks Bayside Community, Offers Sweeping Views Of Little Sarasota Bay And Exception...

Image 2: A4635707

662 Fernwalk Lane, OSPREY, FL - $2,995,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 4,359 SQFT
  • 140 DOM
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**fantastic, Fully Renovated Estate With Lake / Garden View Is Situated On A Serene, Interior, Cul-de-sac Lot With No Flood Concern (zone “x”) Behind The Secure Gates Of The Highly Sought After Bayside Neighborhood Within The Oaks Country Club Com...

Image 3: A4644125

236 Saint James Park, OSPREY, FL - $2,900,000

Residential, Single Family Residence
  • 6 Beds
  • 7 Baths
  • 6,246 SQFT
  • 84 DOM
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Tucked Away In A Quiet Cul-de-sac On A Double Lot Beneath Majestic Oaks, This Almost 5,000 Sq Ft, Timeless 2-story Home Blends Sophistication With Modern Comfort. Situated On The First Hole Of Heron Golf Course, The Home Features Soaring 11-ft Cei...

Image 4: A4642364

49 Osprey Point Drive, OSPREY, FL - $2,745,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,953 SQFT
  • 106 DOM
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Nestled In The Prestigious Gated Enclave Of The Oaks Bayside In Sarasota, This Sedona-inspired Retreat Was Recently Updated From Wall To Wall Creating A Like Brand New Home. The Estate Seamlessly Blends Modern Luxury, Comfort, And Serenity. With A...

Image 5: A4647690

340 Osprey Point Dr, OSPREY, FL - $2,500,000

Residential, Single Family Residence
  • 5 Beds
  • 7 Baths
  • 6,001 SQFT
  • 75 DOM
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Introducing The Grand Estate At The Oaks Bayside—a True Masterpiece Of Refined Living Within One Of Sarasota’s Most Prestigious Gated Communities. Surrounded By Majestic Oak Trees And Lush Tropical Landscaping, This Extraordinary Residence Offers ...

Image 6: A4647789

600 Eagle Watch Lane, OSPREY, FL - $2,385,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 3,681 SQFT
  • 72 DOM
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Located On One Of The Most Desirable Streets In The Oaks Clubside, This Completely Renovated Pool Home Sits On A Generous 0.71-acre Lot With Wide Views Of The Third Hole Of The Heron Golf Course. Nearly Every Aspect Of The Property Has Been Update...

Image 7: A4632694

85 Sugar Mill Drive, OSPREY, FL - $2,150,000

Residential, Single Family Residence
  • 3 Beds
  • 3 Baths
  • 4,191 SQFT
  • 155 DOM
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**stunningly Designed And Updated -- Architectural Estate In The Coveted Oaks Bayside Country Club Neighborhood** On Little Sarasota Bay Waters Features 3 Beds Plus Den/office, 3 Full Baths And Incredible Detail Throughout Including Beautiful Crow...

67 Sugar Mill Drive, OSPREY, FL - $1,995,000

Residential, Single Family Residence
  • 4 Beds
  • 5 Baths
  • 4,020 SQFT
  • 119 DOM
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Bring Your Clubs And Come See This Beautifully Remodeled Home In The Oaks Club (bayside). Move In Ready With All The Amenities You Need. This Home Boast All The Room You Need With 4 Bedroom And A Study/bourbon Room. Totally Secluded Back Yard For ...

Image 9: A4655736

140 Sugar Mill Drive, OSPREY, FL - $1,970,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,286 SQFT
  • 6 DOM
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**brillianty Designed, Fully Renovated, Stunning And Serene Estate With Lush Garden Landscape** Is Located Behind The Secure Gates Of The Oaks Bayside, Country Club Neighborhood. Featuring 4 Bedrooms (2 En Suite) And 4 Full Baths, This Open Floorp...

Image 10: A4631057

401 Walls Way, OSPREY, FL - $1,825,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 4,388 SQFT
  • 199 DOM
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Recently Appraised For Over 2 Million, Seller Relocating. Exquisite Executive Home In The Oaks Clubside, Step Into Elegance And Luxury With This Stunning Two-story Masterpiece. Perfectly Situated To Capture Breathtaking Views Of The 9th Fairway O...

Image 11: A4621683

909 Macewen Drive, OSPREY, FL - $1,795,000

Residential, Single Family Residence
  • 3 Beds
  • 4 Baths
  • 4,241 SQFT
  • 279 DOM
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**stunning Golf Course Estate In The Highly Sought-after Oaks Country Club Community** Situated On An Over Half Acre Lot Overlooking The 12th Fairway Of The Interior, Heron Golf Course. With Its Delightful Curb Appeal And Manicured Landscape, Thi...

Image 12: A4644989

402 Walls Way, OSPREY, FL - $1,650,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,464 SQFT
  • 91 DOM
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Welcome To Timeless Elegance And Modern Comfort In The Oaks Clubside. This Stunning 4-bedroom Plus Den/office, 3.5-bath Home, Built In 2014 By Todd Johnson Homes, Blends Country Modern Style With Refined Sophistication. Situated On An Oversized ....

Image 13: A4637541

135 North Creek Lane, OSPREY, FL - $1,185,000

Residential, Single Family Residence
  • 4 Beds
  • 4 Baths
  • 3,160 SQFT
  • 144 DOM
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Experience The Ideal Blend Of Tranquility And Convenience In This Exquisite Residence, Designed By Renowned Builder Robert Guengerich As His Sanctuary. Set At The End Of A Serene Cul-de-sac And Surrounded By Mature Oak Trees, This Remarkable Home ...

Image 14: A4635743

227 Saint James Park, OSPREY, FL - $1,045,000

Residential, Single Family Residence
  • 2 Beds
  • 2 Baths
  • 2,071 SQFT
  • 154 DOM
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**turnkey Furnished, Elegant And Traditional Estate By Famed Architect, Bo Macewen, On The Single Largest 0.32 Acre Cul De Sac Lot In The Popular Saint James Park Neighborhood In The Oaks Country Club. New Roof (2024), Hurricane Impact Windows An...

Image 15: A4645829

13 Bayhead Lane, OSPREY, FL - $965,000

Residential, Single Family Residence
  • 2 Beds
  • 2 Baths
  • 2,310 SQFT
  • 77 DOM
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**impressive, Move-in Ready, Pool Home In The Secure And Coveted Oaks Preserve, Maintenance-free Community** This Residence Boasts An Open Floor Plan That Is Ideal For Entertaining, Along With A Screened And Spacious Outdoor Pool Area That Provide...

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 DBA Stellar MLS.

Listing information last updated on June 19th, 2025 at 3:20pm EDT.

The Oaks Club Description (continued)

Features & Amenities

  • The Oaks I Bayside features 197 homes sites with many houses directly on Little Sarasota bay.
  • The Oaks II Clubside features 358 estate-sized home sites bordering the Oaks golf courses.
  • The Oaks Preserve features preserve home sites in a natural estuary.
  • Meridian at the Oaks Preserve a bay front condominium development behind the gates of the Oaks Preserve.

Homeowners Association Information

  • HOA Fees: $1600 to $5000/year
  • CDD Fees: No CDD!
  • Fee includes: Gated Entrance, Security, Private Road, Common Area Maintenance & Landscaping

Nearby Schools

  • Laurel Nokomis Elementary
  • Sarasota Middle
  • Venice High

Membership is mandatory with any real estate purchase in Oaks I, Oaks II Oaks Preserve and Meridian. Equity and social memberships are available.

Location

The Oaks Club
301 MacEwen Dr.
Osprey, FL 34229
Website: http://www.theoaksclub.com

Directions: The Oaks is located just south of Sarasota in Osprey, FL. Take US 41 two miles south of Sarasota Square Mall.

Do you have any questions or need more information on buying a home in The Oaks Club?
Contact me today so we can talk about your real estate needs.

Map of The Oaks Club

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