To schedule a showing of 3435 Winding Oaks Drive UNIT #18, Longboat Key, Florida, Call David Shippey at 863-521-4517 TODAY!
$949,000 | 3 beds | 2 full baths | 1 half baths | 2,555 sqft
Longboat Key, FL 34228
- 3Beds
- 3.00Total Baths
- 2 Full, 1 HalfBaths
- 2,555SqFt
- 1988Year Built
- 13.84Acres
- MLS# A4680403
- Residential
- Condominium
- Active
- Approx Time on Market4 months, 15 days
- Area34228 - Longboat Key
- CountySarasota
- Subdivision Winding Oaks
Overview
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 Armands and Downtown Sarasota.
Agriculture / Farm
Association Fees / Info
Community Features: Pool, RecreationArea, Waterfront, Gated
Pets Allowed: DogsOk, SizeLimit, Yes
Hoa Fees Frequency: Quarterly
Association: Yes
Association Amenities: Pool
Association Fee Includes: CommonAreas, CableTv, MaintenanceGrounds, MaintenanceStructure, Pools, RecreationFacilities, ReserveFund, Security, Taxes, Trash
Hoa Fees: 6271
Bathroom Info
Total Baths: 3.00
Fullbaths: 2
Building Info
Window Features: Blinds, WindowTreatments
Roof: Tile
Building Area Source: PublicRecords
Buyer Compensation
Exterior Features
Pool Features: Association, Community
Patio: RearPorch, Patio, Screened
Exterior Features: Awnings, Courtyard, Garden, Lighting, PrivateEntrance, PrivateYard
Fees / Restrictions
Association Fee: 922
Association Fee Frequency: Annually
Financial
Original Price: $1,150,000
Disclosures: CovenantsRestrictionsDisclosure
Fencing: Masonry
Garage / Parking
Parking Features: Garage, GarageDoorOpener
Attached Garage: Yes
Garage: Yes
Green / Env Info
Interior Features
Fireplace Desc: LivingRoom
Fireplace: Yes
Floors: Carpet, Tile, Vinyl, Wood
Levels: One
Laundry Features: Inside, LaundryRoom
Interior Features: TrayCeilings, CeilingFans, EatInKitchen, LivingDiningRoom, MainLevelPrimary, OpenFloorplan, SplitBedrooms
Appliances: BuiltInOven, Dryer, Dishwasher, ElectricWaterHeater, Disposal, Microwave, Range, Refrigerator, Washer
Lot Info
Direction Remarks: Gulf 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.
Lot Size Units: Acres
Lot Size Acres: 13.84
Lot Sqft: 602,945
Lot Desc: BuyerApprovalRequired
Misc
Other
Special Conditions: None
Security Features: SecuritySystemLeased, SecuritySystem, SecurityGate, SmokeDetectors, GatedWithGuard, GatedCommunity
Other Rooms Info
Property Info
Section: 05
Class Type: Condominium
Property Sub Type: Condominium
Construction Materials: HardiplankType
Stories: 1
Total Stories: 1
Foundation: Block, Slab
Human Modified: Yes
Room Info
Total Rooms: 10
Sqft Info
Sqft: 2,555
Bulding Area Sqft: 3,270
Living Area Units: SquareFeet
Living Area Source: PublicRecords
Tax Info
Tax Year: 2,025
Tax Lot: 18
Tax Legal Description: UNIT 18 WINDING OAKS
Tax Annual Amount: 8564.88
Tax Book Number: 27-27
Unit Info
Unit: 18
Utilities / Hvac
Heating: Central, Electric
Water Source: Public
Sewer: PublicSewer
Cool System: CentralAir, HumidityControl, CeilingFans
Cooling: Yes
Heating: Yes
Utilities: CableAvailable, ElectricityConnected, HighSpeedInternetAvailable, MunicipalUtilities, SewerConnected, UndergroundUtilities, WaterConnected
Waterfront / Water
Waterfront Features: BayAccess, BeachAccess, GulfAccess, Pond
View: Yes
View: GolfCourse, Pond, Water
Directions
Gulf 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.This listing courtesy of Michael Saunders & Company
The information being provided by © 2026 My Florida Regional MLS DBA Stellar MLS is for the consumer's
personal, non-commercial use and may not be used for any purpose other than to
identify prospective properties consumer may be interested in purchasing. Any information relating
to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX)
program of the My Florida Regional MLS DBA Stellar MLS. XCELLENCE is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of XCELLENCE, a broker participant of My Florida Regional MLS DBA Stellar MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site.
MLS IDX data last updated on 06-18-2026 5:57 PM EST.
If you have any questions on 3435 Winding Oaks Drive UNIT #18, Longboat Key, Florida, please call David Shippey at 863-521-4517.
MLS# A4680403 located at 3435 Winding Oaks Drive UNIT #18, Longboat Key, Florida is brought to you by David Shippey REALTOR®
3435 Winding Oaks Drive UNIT #18, Longboat Key, Florida has 3 Beds, 2 Full Bath, and 1 Half Bath.
The MLS Number for 3435 Winding Oaks Drive UNIT #18, Longboat Key, Florida is A4680403.
The price for 3435 Winding Oaks Drive UNIT #18, Longboat Key, Florida is $949,000.
The status of 3435 Winding Oaks Drive UNIT #18, Longboat Key, Florida is Active.
The subdivision of 3435 Winding Oaks Drive UNIT #18, Longboat Key, Florida is Winding Oaks.
The home located at 3435 Winding Oaks Drive UNIT #18, Longboat Key, Florida was built in 2026.