Winding Oaks
Real Estate Listings & Community Guide
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. Read more
Winding Oaks Condos Overview

Community Info:
# of Condos: | 56 |
Year Built: | 1988-1991 |
Gated: | Yes |
Pool: | Yes |
Pets: | Yes |
Golf Course: | Yes |
Condo Fee: | Yes |
CDD Fee: | No |
Min. Lease: | 3 Months |
# of Leases: | 3 /Year |
Amenities:
- Gated
- Pool
- Spa
- Clubhouse
- Waterfront
- Golf is optional
Condo Fee Includes:
- Building Exterior, Cable, Community Pool, Escrow Reserves Fund, Fidelity Bond, Flood Insurance, Ground Maintenance, Pest Control.
Category: Longboat Key Condos For Sale
*Accuracy of info provided is not guaranteed. All info must be verified before making a purchase decision.
Transactions
400+
Sales
1/4 Billion
5-Star Reviews
150+

HONESTY · Reputation · Experience
Top 3% Condo Sales Team in Sarasota & Manatee County
Current Condos For Sale in Winding Oaks | Longboat Key, FL.

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Insight For Winding Oaks Condominiums
Pros:
- Maintenance-free villas that live like single homes
- Pet-friendly community
- Membership to Bay Isles Beach Club.
Considerations:
- No boat docks available in community
Lifestyle:
- Peaceful private beach living
- First class amenities optionally available at Longboat Key Club
- Fine and casual restaurants located on Longboat Key
Shopping:
- Publix grocery store is 1.1 miles
- UTC Mall is about 17.9 miles
- Saint Armands Circle is about 5.7 miles
Beach:
- Longboat Key is private beach
- Lido Key Beach is 6.1 miles
- Siesta Key Beach is 15.1 miles
Downtown:
- 9.7 miles
- 22 minute drive
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
Frequently Asked Questions
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.