Longboat Key, FL
Winding Oaks
A Bay Isles community built around greenery: a pool, a private park, and walking trails set in a lush residential setting. For buyers who want the gate and the quiet, with nature at the door. The county roll assesses 56 units, built 1988, rising 1 floor, in Sarasota County.
Price Range
Est. $700s to $1M
Home Types
Single-family / villas
Total Homes
56 units
Amenity Level
Medium
HOA (Yearly) Est.
$26,006 - $28,776
CDD (Yearly) Est.
None
Flood Zone
AE
Fee estimates may vary by lot size and sub-association. View all community fees →
Amenities & lifestyle
- Community pool
- Private park
- Walking trails
- Bay Isles Beach Club access
Michael’s Take
County roll: 56 units, built 1988, 1 floors, assessed in Sarasota County. No CDD; Longboat Key carries none.
How Winding Oaks compares
From the county records
$1,050,000
Median of 11 recorded sales since October 2023, the middle eighty percent between $850,000 and $1,195,000.
18%
Of the 56 finished houses here carry a homestead exemption, which reads as largely second homes and seasonal owners.
Newest building completed 1988. The roll records no completions here in the last three years, so this is a built-out community rather than one still being delivered.
Arm’s-length sales recorded with Sarasota County, read October 2026. Quitclaims, foreclosures, family transfers and pre-construction sales are excluded. Homestead requires the property to be a permanent residence, so the share carrying one is a strong proxy for how many owners live here full time, not a census of them.
At an estimated $27,391 a year in combined HOA and CDD, Winding Oaks sits about 37% above the Longboat Key median of $20,000, ranking 45 of the 62 Longboat Key communities whose fees this site tracks. There is no CDD assessment here, which is what keeps that figure down.
Estimates from the same dataset behind the fee pages and the True Cost Index. Fees vary by lot size and sub-association, and change with each budget.
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Winding Oaks FAQ
How much do homes in Winding Oaks cost?+
Homes in Winding Oaks are generally priced in the Est. $700s to $1M range. Pricing moves with the market and varies by floor plan, lot, and incentives, so reach out for the most current numbers.
What kind of homes are in Winding Oaks?+
Winding Oaks offers single-family / villas. Attached homes carry an association that maintains the building itself, so the fee covers more than it would on a single-family home and the association's reserves matter to you directly. What a specific home includes, and what the association maintains, is set out in that community's documents and is worth reading before an offer rather than after.
What amenities does Winding Oaks have?+
Winding Oaks offers Community pool, Private park, Walking trails, Bay Isles Beach Club access. Worth separating two things that often get blurred together: amenities the HOA maintains and which every owner pays for, and club or golf facilities that may require a separate membership on top. Which category each amenity falls into determines your actual annual cost, and it is set out in the community documents rather than in any listing.
What have homes in Winding Oaks actually sold for?+
11 arm's-length sales have been recorded in Winding Oaks since October 2023, at a median of $1,050,000. The middle eighty percent of those sales fell between $850,000 and $1,195,000, which is a better guide to the range than the extremes. These are prices recorded with Sarasota County, not asking prices, so they describe what buyers and sellers actually agreed. Figures read October 2026; quitclaims, foreclosures and family transfers are excluded.
Do people live in Winding Oaks year round?+
18% of the 56 finished homes in Winding Oaks carry a homestead exemption, which Florida grants only on an owner's permanent residence. That reads as largely second homes and seasonal owners. It is a strong proxy rather than a census, since an owner who lives there but never filed does not appear in it, but it is the most direct public signal of how occupied a community is outside the winter.
Is Winding Oaks still being built?+
The most recent home the county records in Winding Oaks was completed in 1988, across 57 platted parcels of which 56 carry a finished home. The county records no completions here in the last three years, so Winding Oaks is built out and what trades is resale rather than new construction. Build year matters more in Florida than buyers expect, because insurers weight roof age heavily and it drives what a property costs to carry rather than just what it costs to buy.
Does Winding Oaks have an HOA or CDD fee?+
Winding Oaks has an HOA fee estimated at $26,006 - $28,776 yearly, and the fee data for this community records no CDD assessment. That matters more than it sounds: a CDD is a bond repayment attached to the land and billed with your property taxes, so its absence is a permanent annual difference against communities that carry one. Figures are estimates and vary by home, so confirm them for the specific address before relying on them.
What flood zone is Winding Oaks in?+
The flood zone recorded for Winding Oaks is AE. Zones beginning A or V are the higher-risk categories, where a federally backed mortgage generally requires flood insurance, while zone X is lower risk and coverage is usually optional. Flood zone is assigned per property rather than per community though, and elevation can change both the requirement and the premium substantially, so get the zone and the elevation certificate for the exact address rather than relying on a community-level figure.