3460 WINDING OAKS DR #38

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.

MLS ID#

MFRA4695005

Price

$1,150,000

Status

Active

Bedrooms

3

Bathrooms

4

Full Baths

3

Half Baths

1

Square Footage

2,608 sqft

Acres

0.0000

Year Built

1988

Type

Residential

Subtype

Condominium

Style

Other

Address

3460 WINDING OAKS DR #38

Subdivision

Winding Oaks

City

Longboat Key

County

Sarasota

State

FL

Zip Code

34228

Senior Community

No

Amenities

Maintenance, Pool

Parking

N/A

View

No

Waterfront

Yes

Pool

No

Interior Features

Cathedral Ceiling(s), Ceiling Fans(s), Eat-in Kitchen, High Ceilings, Open Floorplan, Window Treatments, Walk-In Closet(s), Solid Surface Counters, Primary Bedroom Main Floor, Thermostat

Heating

Central, Electric

Cooling

Central Air

Flooring

Tile

Fireplace

Gas

Stories

1

Appliances

Dishwasher, Disposal, Microwave, Range, Refrigerator, Dryer, Washer, Gas Water Heater, Range Hood, Wine Refrigerator, Tankless Water Heater

Exterior Features

Sliding Doors, Sidewalk

Construction

Frame

Foundation

Slab

Roof

Tile

Fencing

N/A

Lot Features

N/A

Elementary

N/A

Middle

N/A

High

N/A

Date Listed

June 2, 2026

Days on Market

0

Zoning

MUC1

Direction Faces

East

New Construction

No