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Own your own slice of tropical paradise on Longboat Key with this beautiful two bedroom two and on half bath Villa in the exclusive Winding Oaks Community located behind the gates of Bay Isles Association. Sweeping views of the Longboat Key Club Harbourside Golf Course and a sparkling inland waterway from your primary bedroom and expansive living/dining room combo that both exit through sliders to a fully enclosed wrap around deck to further enhance your tropical lifestyle. Open floor plan with soaring ceilings and enclosed atrium help to maximize the natural light and make the 2,555 sq feet feel even larger. Beautifully updated eat in kitchen with striking tray ceiling, ample pantry storage, bright white cabinets, quartz countertops and stainless steel appliances. Primary owners suite includes an designer walk in closet, updated bath with ceramic tile, walk in shower, double sinks and quartz counter tops. Split layout offers a private guest suite, with walk in closet, updated ensuite bathroom with ceramic tile, walk in shower and quartz counter tops. Large office with desk nook could easily be converted to another bedroom. Laundry room with storage and sink adjacent to large 2 car garage with epoxy floors and storage cabinets. Meticulously maintained, Impact Windows and sliders throughout, low maintenance mature plantings in private enclosed front courtyard. Dog friendly community. Beautiful updated community pool with bathrooms. Beach access via Bay Isles Beach Club which offers a private pavilion with bathrooms, volleyball, picnic tables, grills and ample parking. Low maintenance community where all exteriors and court yards are maintained by the association. Conveniently located mid key, one mile from Publix and CVS and a short drive to the restaurants and shops of St Armand's and Downtown Sarasota.
| DAYS ON MARKET | 51 | LAST UPDATED | 2/26/2026 |
|---|---|---|---|
| TRACT | WINDING OAKS | YEAR BUILT | 1988 |
| COMMUNITY | 34228 - Longboat Key | GARAGE SPACES | 2.0 |
| COUNTY | Sarasota | STATUS | Active |
| PROPERTY TYPE(S) | Condo/Townhouse/Co-Op |
| Elementary School | Southside Elementary |
|---|---|
| Jr. High School | Booker Middle |
| High School | Booker High |
| ADDITIONAL DETAILS | |
| AIR | Central Air, Humidity Control |
|---|---|
| AIR CONDITIONING | Yes |
| AMENITIES | Cable TV, Maintenance Grounds, Maintenance Structure, Trash |
| APPLIANCES | Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer |
| AREA | 34228 - Longboat Key |
| CONSTRUCTION | HardiPlank Type |
| EXTERIOR | Awning(s), Courtyard, Garden, Lighting, Private Entrance, Private Yard |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Central, Electric |
| INTERIOR | Eat-in Kitchen, Open Floorplan, Tray Ceiling(s) |
| LOT | 13.84 acre(s) |
| PARKING | Garage Door Opener, Attached |
| SEWER | Public Sewer |
| STORIES | 1 |
| SUBDIVISION | WINDING OAKS |
| TAXES | 8564.88 |
| UTILITIES | Cable Available, Electricity Connected, Sewer Connected, Underground Utilities, Water Connected |
| VIEW | Yes |
| VIEW DESCRIPTION | Pond, Water, Golf Course |
| WATER | Public |
| WATERFRONT DESCRIPTION | Beach Access |
MORTGAGE CALCULATOR
TOTAL MONTHLY PAYMENT
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Listing provided by Sean Clark, MICHAEL SAUNDERS & COMPANY, 941-383-7591
The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 3/19/26 7:59 PM PDT.
This IDX solution is (c) Diverse Solutions 2026.
