Reduced to $650,000.
Now accepting pre-listing offers on an amazing Siesta Key property at
5232 Winding Way, Siesta Key, FL 34242. Your opportunity to live on one of the most popular Barrier Islands on the west coast of Florida walking distance from the Gulf and Siesta Beach. Trip Advisor just named Siesta Beach the #1 Beach in the United States and the #4 Beach in the world.
Sadly, the interior of this block house was affected by hurricane Helene and it is being offered AS/IS for $649,000, the appraised value of the property. I’m told homes in this subdivision rent during the season for between $4000-$6000 per month making this property a premium investment. In addition, the protected canopy road around this small subdivision was just graded and paved this year.
NOTE: We are not able to provide special purchase terms on this property.
The existing structure on the property is a 3-bedroom 2-bath
1400+ square-foot home on a 75x100 foot lot with a caged pool. Both the block structure and Key West roof are considered to be structurally sound. The inside is completely framed. Drywall from the floor to about 4 feet high has been removed. Floors are tile and Terrazzo. The property is dotted with lots of tropical foliage including 37 palm trees and the backyard is adjacent to Glebe Park. The park includes a concession stand with restrooms, soccer fields, a baseball field, playground, basketball court, and a shell walking trail, which my wife and I used often.
To make an offer, ask questions or tour the inside please contact owner,
Trebor Britt at 941-320-4309.
For sale by owner
$650,000
5232 Winding Way, Sarasota, FL 34242
3beds
1,430sqft
SingleFamily
Built in 1963
9,000 Square Feet Lot
$-- Zestimate®
$455/sqft
$35/mo HOA
What's special
Caged poolBlock structureKey west roof
What the owner loves about this home
My late wife always felt living in this home was living in paradise this side of heaven.
- 77 days
- 1,162
- 84
Listed by:
Property Owner (941) 320-4309
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Interior area
- Total interior livable area: 1,430 sqft
Property
Lot
- Size: 9,000 Square Feet
Construction
Type & style
- Home type: SingleFamily
Condition
- New construction: No
- Year built: 1963
Community & HOA
HOA
- Has HOA: Yes
- HOA fee: $35 monthly
Location
- Region: Sarasota
Financial & listing details
- Price per square foot: $455/sqft
- Date on market: 7/27/2026
Estimated market value
Not available
Estimated sales range
Not available
$4,792/mo
Price history
| Date | Event | Price |
|---|---|---|
| 7/27/2026 | Listed for sale | $650,000$455/sqft |
Source: Owner Report a problem | ||
| 2/8/2026 | Listing removed | -- |
Source: Owner Report a problem | ||
| 11/10/2025 | Listed for sale | $650,000$455/sqft |
Source: Owner Report a problem | ||
Public tax history
Tax history is unavailable.
Monthly payment
Est. payment






