3466 WINDING OAKS DRIVE 35, Longboat Key, FL 34228

• 2 beds |
• 2 baths |
• 2,039 sqft

Property Description

Located in one of the most sought-after villa communities on Longboat Key, this well-kept 2-bedroom, 2-bath home in Winding Oaks lives more like a single-family residence—without all the upkeep. Behind the gates of Bay Isles, it offers a great opportunity to enjoy a quiet, established neighborhood known for its natural beauty and relaxed feel. A paver driveway and walkway, surrounded by mature landscaping, lead you to the front door. Inside, high ceilings and warm wood floors immediately make the space feel open and inviting. The finishes are neutral and timeless, and the natural light really does the rest. Impact glass throughout adds both comfort and peace of mind. The main living area flows easily, with a striking corner of sliding glass doors that brings the outdoors in and opens to a spacious, screened, deck. It’s the kind of space you’ll actually use—whether that’s for entertaining, relaxing, or just enjoying the greenery around you. The kitchen is nicely laid out with stone countertops, stainless appliances, a tray ceiling, and a large window that keeps things bright. Both bedrooms are generously sized. The primary suite feels like a true retreat, with vaulted ceilings, a walk-in closet, and sliding doors that open to the deck with peaceful nature views. The bathroom is spacious, featuring dual vanities, a Jacuzzi tub, walk-in shower, and well-done tile details. Additional highlights include a two-car garage and a floor plan that offers a nice balance of openness and privacy. Winding Oaks is part of the Bay Isles Harbourside golf course community and offers a gated entrance, community pool, and access to Bay Isles amenities—including deeded beach access through the private Bay Isles Beach Club. It’s an easy, comfortable lifestyle in one of Longboat Key’s most desirable communities.

Listing Status:

Active

Date Added:

April 7, 2026

Data Last Updated:

April 30, 2026 at 9:21PM

Listing Office:

COLDWELL BANKER REALTY : 941-383-6411

Listing Agent:

Bruce Myer : 941-376-5311

MLS ID:

A4686581

Interior

• General: Built-in FeaturesCeiling Fans(s)Eat-in KitchenOpen FloorplanPrimary Bedroom Main FloorSolid Surface CountersStone CountersThermostatWindow Treatments
• Appliances: Built-In OvenCooktopDishwasherDisposalDryerMicrowaveRefrigeratorWasher
• Laundry: Laundry Room
• Flooring: TileWood
• A/C: Central Air
• Heating: CentralElectric

Exterior

• General: LightingSidewalkSliding DoorsStorage
• Style: Other
• Other Structures: DeckRear PorchCovered
• Pool: HeatedIn Ground
• Parking: DrivewayGarage Door Opener

Construction

• Roofing: Other
• General: BlockStuccoOneSlab

Location

• Road/Access: Paved
• HOA Amenities: PoolPoolEscrow Reserves FundInsuranceMaintenance StructureMaintenance GroundsPest ControlPrivate RoadSewerTrashWater791.03Annually
• Originating MLS: Stellar MLS
• County: Sarasota

Lot

• Zoning: MUC1UNIT 35 WINDING OAKS0004121035
• View: Water

Utilities

• Utilities: Electricity ConnectedPublicSewer ConnectedUnderground UtilitiesWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple