3460 WINDING OAKS DR #38, LONGBOAT KEY, FL, 34228
$1,150,000
Residential
Bedrooms
3
Bathrooms
4
Living Area
2,608 Sqft
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.
Property Details
Property Features Property Features
MLS ID: MFRA4695005 Year Built: 1988
Appliances: Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator Architectural Style: Other
Association Amenities: Maintenance, Pool Association Fee Includes: Guard - 24 Hour, Pool, Management, Private Road
Community Features: Buyer Approval Required, Deed Restrictions, Pool Construction Materials: Frame
Cooling: Central Air Country: US
County Or Parish: Sarasota Direction Faces: East
Exterior Features: Sidewalk, Sliding Doors Fireplace Features: Gas
Flooring: Tile Foundation Details: Slab
Furnished: Negotiable Heating: Central, Electric
Laundry Features: Laundry Room Levels: One
Listing Agreement: Exclusive Right To Sell Listing Terms: Cash, Conventional
Occupant Type: Owner Parking Features: Garage Door Opener
Patio And Porch Features: Rear Porch Pets Allowed: Yes
Pool Features: Heated, In Ground Property Condition: Completed
Property Sub Type: Condominium Property Type: Residential
Road Responsibility: Private Maintained Road Road Surface Type: Paved
Roof: Tile Sewer: Public Sewer
Showing Requirements: Listing Agent Must Accompany, ShowingTime Spa Features: Heated, In Ground
Special Listing Conditions: None Standard Status: Active
State Or Province: FL Utilities: Electricity Connected, Sewer Connected, Underground Utilities, Water Connected
Vegetation: Mature Landscaping View: Water
Water Source: Public Waterfront Features: Lake Front
Window Features: Blinds, Window Treatments
Rooms Rooms
Living Room: 22x29 ft Kitchen: 15x23 ft
Balcony/Porch/Lanai: 45x23 ft Primary Bedroom: 14x17 ft
Bedroom 2: 14x14 ft Bedroom 3: 15x14 ft
Laundry: 7x5 ft
We love to hear from you