3460 WINDING OAKS DRIVE 38, Longboat Key, FL 34228

• 3 beds |
• 4 baths |
• 2,608 sqft

Property Description

Tucked within Winding Oaks, one of Longboat Key’s most sought-after villa communities, this 3BR/3BA residence offers the scale and comfort of a single-family home paired with the simplicity of maintenance-free living. From the paver drive and walkway to the stepped front entry, the residence creates an inviting first impression before opening into a home defined by volume, light and connection to the outdoors. Step inside and soaring ceilings immediately create a sense of openness, while high-set windows invite natural light to move throughout the living spaces. Tile flooring and soft neutral tones create a clean backdrop that complements the peaceful setting just beyond the glass. Renovated in November 2025, the kitchen has been thoughtfully opened and redesigned into a true centerpiece for gathering and everyday living. A substantial island with seating anchors the space, along with stone countertops, white cabinetry, stainless steel appliances, a range hood, wine refrigerator and tile backsplash. An abundance of windows and an adjoining sitting area create a bright, welcoming space whether hosting guests or enjoying a quiet morning. The dining area transitions naturally into the living room, where cathedral ceilings, a corner fireplace and sliding glass doors connect the interior to the outdoors. Beyond, an expansive screened deck overlooks the community lake and fountain, creating a peaceful setting with multiple areas for dining, relaxing or entertaining. Privacy walls on either side enhance the feeling of seclusion while keeping the water views front and center. The primary suite is spacious and calming, featuring vaulted ceilings, engineered wood floors, a wall of sliding glass doors opening to the deck and a large walk-in closet with extensive built-ins. Also renovated in November 2025, the primary bath offers dual vanities, a walk-in shower, dressing area and separate water closet. Guest accommodations are equally well planned. One bedroom includes an en suite bath and walk-in closet, while another is currently configured as an office space with sliding glass doors opening to a private patio. Updated baths throughout, an in-residence laundry room and a 2-car garage add convenience. Set within the Harbourside golf course community, Winding Oaks offers a serene environment with a gated entrance, community pool and spa, and access to the full range of Bay Isles amenities, including deeded beach access through the private Bay Isles Beach Club.

Listing Status:

Active

Date Added:

June 2, 2026

Data Last Updated:

June 28, 2026 at 1:23AM

Listing Office:

COLDWELL BANKER REALTY : 941-383-6411

Listing Agent:

Bruce Myer : 941-376-5311

MLS ID:

A4695005

Interior

• General: Cathedral Ceiling(s)Ceiling Fans(s)Eat-in KitchenHigh CeilingsOpen FloorplanPrimary Bedroom Main FloorSolid Surface CountersThermostatWalk-In Closet(s)Window Treatments
• Appliances: DishwasherDisposalDryerGas Water HeaterMicrowaveRangeRange HoodRefrigeratorTankless Water HeaterWasherWine Refrigerator
• Laundry: Laundry Room
• Flooring: Tile
• A/C: Central Air
• Heating: CentralElectric
• Fireplace: GasFireplace

Exterior

• General: SidewalkSliding DoorsHeatedIn Ground
• Style: Other
• Other Structures: Rear Porch
• Pool: HeatedIn Ground
• Parking: Garage Door Opener

Construction

• Roofing: Tile
• Windows: BlindsWindow Treatments
• General: FrameOneSlab

Location

• Road/Access: Paved
• HOA Amenities: MaintenancePoolGuard - 24 HourPoolManagementPrivate Road1522.96Annually
• Originating MLS: Stellar MLS
• County: Sarasota

Lot

• Zoning: MUC1UNIT 38 WINDING OAKS0004121038
• View: Water

Utilities

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

Financial

• Source: Stellar MLS
• Ownership: Fee Simple