Winding Oaks Condos For Sale | Longboat Key, FL
Winding Oaks Condominiums in Longboat Key, FL.
Winding Oaks condos for sale are a wonderful community nestled within the Longboat Key Club’s exclusive Bay Isles Harbourside golf course community. These one-level villa have the feel of a single-family home with 2-car garage, while delivering a private walled courtyard, large deck and many have private pools. The community of Winding Oaks Villas experienced nearly $3 million in capital improvements which completely transformed the community. These upgrades included a state-of-the-art infinity swimming pool, tile roofs, paver drives & walkways, exterior painting, mailboxes & entry signs.
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Amenities Include:
- Gated
- Pool
- Spa
- Clubhouse
- Waterfront
- Golf is optional
Community Fee Includes:
- Building Exterior, Cable, Community Pool, Escrow Reserves Fund, Fidelity Bond, Flood Insurance, Ground Maintenance, Pest Control.
Key Facts:
| # of Homes | 56 |
| Years Built | 1988 – 1991 |
| Gated | Yes |
| Community Pool | Yes |
| Pets | Yes |
| Golf Course | Yes |
| Condo Fee | Yes |
| CDD Fee | No |
| Min. Lease | 3 Months |
| # of Leases | 3 /Year |
Condominium Category:
*Accuracy of info provided is not guaranteed. All info must be verified before making a purchase decision.
Photos of Winding Oaks Condos in Longboat Key, FL.

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Current Condos For Sale in Winding Oaks | Longboat Key, FL.

Winding Oaks
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Additional Winding Oaks Condo Information
The neighborhood is managed by a hands-on Homeowners Assoc. & Board of Directors. Residents enjoy the beauty, security & benefits of Bay Isles, including access to Bay Isles Beach Club on the Gulf of Mexico. The community is pet-friendly, and residents enjoy numerous neighborhood social activities.
Winding Oaks Condominiums
Winding Oaks has about 56 condos, built between 1988-1991.
Yes, Winding Oaks has a heated pool.
Yes, Winding Oaks is a gated community within Bay Isles Lonbboat Key.
Winding Oaks is located in a golf course community. Residents may join the Longboat Key Club which offers the Islandside 18 Hole Golf Course and Harbourside 27 Hole Golf Course. Additionally, there are two clubhouses, 6 restaurants, an award winning tennis center with 22 Har-Tru courts, fitness center, full-service spa, and a 29 slip marina within Longboat Key Club.
Winding Oaks is located about 8.3 miles from downtown Sarasota.
Winding Oaks is located about 1.7 miles from Bay Isles Beach Club. Residents of Winding Oaks have a membership to Bay Isles Beach Club.
Winding Oaks is located about 11.6 miles from the Sarasota International Airport.
Yes, however we recommend that you consult with a Realtor to get specific pet policy info for this community. We are happy to help you.
*Accuracy of info provided is not guaranteed. All info must be verified before making a purchase decision.
Longboat Key FL. Condominiums
Aquarius Club
$1.5M–$1.6M
Banyan Bay Club
$595k–$794k
Bay Harbour
$650k–$700k
Bayport
$450k–$1.4M
Beach Harbor Club
$290k–$550k
Beaches
$1.0M–$2.5M
Beachplace
$600k–$2.2M
Buttonwood Cove
$440k–$1.0M
Casa Del Mar
$600k–$800k
Cedars East
$900k–$1.5M
Cedars West
$800k–$900k
Club Longboat
$490k–$950k
Diplomat
$450k–$550k
En Provence
$3.0M–$5.0M
Fairway Bay
$400k–$1.7M
Grand Bay
$650k–$2.7M
Grande
$300k–$500k
Inn On The Beach
$410k–$1.1M
Islander Club
$825k–$1.4M
Islands West
$1.3M–$1.6M
L’Ambiance
$2.7M–$10.2M
La Firenza
$3.8M–$5.0M
Longboat Beachcomber
$900k–$1.0M
Longboat Harbour
$325k–$800k
Longboat Harbour Towers
$900k–$1.3M
Longboat Key Towers
$1.2M–$1.6M
Marina Bay
$1.3M–$2.4M
Pierre
$1.4M–$3.0M
Players Club
$795k–$1.6M
Portobello
$700k–$1.2M
Positano
$5.0M–$7.0M
Privateer
$690k–$1.6M
Promenade
$800k–$2.1M
Regent Place
$3.8M–$4.5M
Sage
$4.0M–$7.0M
Sanctuary
$1.5M–$3.6M
Sand Cay
$800k–$1.2M
Sands Point
$950k–$2.0M
Sea Gate Club
$1.0M–$2.0M
Seaplace
$400k–$900k
Shore
$700k–$900k
Spanish Main
$200k–$650k
St. Regis Residences
$2.4M–$13.0M
Sunset Beach
$1.0M–$2.0M
Sutton Place
$300k–$600k
Tangerine Bay Club
$900k–$3.0M
Tiffany Plaza
$1.0M–$2.0M
Turtle Crawl
$750k–$900k
Villa Di Lancia
$2.0M–$2.6M
Vizcaya
$3.4M–$5.0M
Water Club
$950k–$4.0M
Westchester
$425k–$925k
Whitney Beach
$387k–$1.0M
Winding Oaks
$895k–$1.2M
Windward Bay
$335k–$1.2M



















































































