3435 WINDING OAKS DRIVE 18, Longboat Key, FL 34228

• 2 beds |
• 3 baths |
• 2,555 sqft

Property Description

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.

Listing Status:

Active

Date Added:

February 26, 2026

Data Last Updated:

March 15, 2026 at 7:24AM

Listing Office:

MICHAEL SAUNDERS & COMPANY : 941-383-7591

Listing Agent:

Sean Clark : 941-312-1146

MLS ID:

A4680403

Interior

• General: Ceiling Fans(s)Eat-in KitchenLiving Room/Dining Room ComboOpen FloorplanPrimary Bedroom Main FloorSplit BedroomTray Ceiling(s)
• Rooms: Den/Library/OfficeInside Utility
• Appliances: Built-In OvenDishwasherDisposalDryerElectric Water HeaterMicrowaveRangeRefrigeratorWasher
• Laundry: InsideLaundry Room
• Flooring: CarpetTileVinylWood
• A/C: Central AirHumidity Control
• Heating: CentralElectric
• Fireplace: Living RoomFireplace

Exterior

• General: Awning(s)CourtyardGardenLightingPrivate EntrancePrivate YardSliding Doors
• Other Structures: Rear PorchScreenedPatio
• Parking: Garage Door Opener

Construction

• Roofing: Tile
• Windows: BlindsWindow Treatments
• General: HardiPlank TypeOneBlockSlab

Location

• Road/Access: Asphalt
• HOA Amenities: PoolVehicle RestrictionsGuard - 24 HourCable TVCommon Area TaxesPoolEscrow Reserves FundFidelity BondMaintenance StructureMaintenance GroundsRecreational FacilitiesTrash922.0Annually
• Originating MLS: Stellar MLS
• County: Sarasota

Lot

• Zoning: MUC1UNIT 18 WINDING OAKS0004121018
• View: Golf CourseWater
• Fencing: Masonry

Utilities

• Utilities: BB/HS Internet AvailableCable AvailableElectricity ConnectedPublicSewer ConnectedUnderground UtilitiesWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Condominium