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LONGBOAT KEY, FL 34228 3435 WINDING OAKS DRIVE 18

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Presented By: MICHAEL SAUNDERS & COMPANY with 941-383-7591. - 941-383-7591
  • MLS# A4680403
  • 01/28/2026
  • Request Tour
  • Request Info
  • Beds • 2
  • Full/Half Baths • 2 / 1
  • SQFT • 2,555
  • Garage • 2

Home Details

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.
Presented By: MICHAEL SAUNDERS & COMPANY with 941-383-7591. - 941-383-7591

Interior Features for 3435 WINDING OAKS DRIVE 18

Bedrooms

Total Bedrooms2

Bathrooms

Half Baths1
Total Baths3

Other Interior Features

LivingAreaSourcePublic Records
Air Conditioning Y/NYes
Common WallsCorner Unit
Fireplace FeaturesLiving Room
Fireplace Y/NYes
FlooringCarpet, Tile, Vinyl, Hardwood
Furnished Y/NFurnished
Heating Y/NYes
Interior AmenitiesCeiling Fan(s), Eating Space In Kitchen, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Tray Ceiling(s)
Laundry FeaturesInside, Laundry Room
Total Stories1
Window FeaturesBlinds, Window Treatments

General for 3435 WINDING OAKS DRIVE 18

Additional Parcels Y/NNo
Additional RoomsDen/Library/Office, Inside Utility
AppliancesBuilt-In Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
Association AmenitiesPool, Vehicle Restrictions
Association Fee Includes24-Hour Guard, Cable TV, Common Area Taxes, Community Pool, Escrow Reserves Fund, Fidelity Bond, Maintenance Structure, Maintenance Grounds, Pool Maintenance, Recreational Facilities, Trash
Association NameNeil Fleet
AssociationName2Bay Isle Association
Attached Garage Yes
Building Area UnitsSquare Feet
Carport Y/NNo
CityLONGBOAT KEY
Community FeaturesGulf/Ocean Front, Association Recreation - Owned, Buyer Approval Required, Deed Restrictions, Gated Community - Guard, Pool
Construction MaterialsHardiPlank Type
CoolingCentral Air, Humidity Control
CountySarasota
DirectionsGulf Of Mexico Dr to Bay Isle Parkway. Check in at Guard Gate and receive pass. Left on Harbourside drive stay in left lane use pass to continue through manual gate. Take right on Winding Oaks Drive Villa is 9th on the right hand side.
Elementary SchoolSouthside Elementary
Facing DirectionSouthwest
Flood Zone CodeAE
Full Baths2
Garage Spaces2
Garage Y/NYes
HOA Fee 2922
HOA Fee 2 FrequencyAnnually
HOA Monthly Maintenance
HeatingCentral, Electric
High SchoolBooker High
Land Lease Y/NNo
Lease Considered Y/NYes
Legal DescriptionUNIT 18 WINDING OAKS
LevelsOne
Listing TermsCash, Conventional
Living Area UnitsSquare Feet
Lot Size Square Feet602945
Lot Size UnitsAcres
MLS Area34228 - Longboat Key
Middle/Junior High SchoolBooker Middle
Minimum Lease3 Months
Monthly Condo Fee Amount2090
New ConstructionNo
Occupancy TypeOwner
OwnershipCondominium
Patio/Porch FeaturesPatio, Rear Porch, Screened
Pet Size LimitLarge (61-100 Lbs.)
Pets AllowedDogs OK, Size Limit, Yes
Property Attached Y/NNo
Property SubtypeCondominium
Property TypeResidential
RoofTile
STELLAR_InLawSuiteYNNo
Security FeaturesGated Community, Security Gate, Security System, Security System Leased, Smoke Detector(s)
Senior Community Y/NNo
SewerPublic Sewer
Standard StatusActive
StatusActive
Subdivision NameWINDING OAKS
Tax Annual Amount8564.88
Tax Lot18
Tax Year2025
Total Rooms10
Unit Number18
UtilitiesBB/HS Internet Available, Cable Available, Electricity Connected, Public, Sewer Connected, Underground Utilities, Water Connected
ViewGolf Course, Water
Water Access TypeBay/Harbor, Beach, Gulf/Ocean, Pond
Water Access Y/NYes
Water ViewPond
Water View Y/NYes
Waterfront FeaturesGulf/Ocean Front
Year Built1988
ZoningMUC1

Exterior for 3435 WINDING OAKS DRIVE 18

Building Area Total3270
Covered Spaces2
Exterior AmenitiesAwning(s), Courtyard, Garden, Lighting, Private Entrance, Private Yard, Sliding Doors
FencingMasonry
Foundation DetailsBlock, Slab
Lot Size Acres13.84
Lot Size Area13.8417
Parking FeaturesGarage Door Opener
Private PoolNo
Road Surface TypeAsphalt
SpaNo
Water SourcePublic
Waterfront Y/NNo

Additional Details

Price History

Steven Silcock

Broker Owner
Price $1,050,000
MLS#A4680403
List Date 01/28/2026
Property Type Condos
Phone 407.574.0218
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