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3460 WINDING OAKS DRIVE UNIT 38

Condo/Co-op For Sale
$1,150,000

BTC: 17.96875000

ETH: 638.88888889

1 days
Waterfront
3 bds
3 ba
2,608 sqft

Overview

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.

Location

Details

Type:
Residential
Parking:
Garage Door Opener
Year Built:
1988
Lot:
No Data
Heating:
Central / Electric
Price/sqft:
$441
Cooling:
Central Air
HOA:
No Data

Valuation

Our model vs. what's actually selling nearby.
Estimate
$1,845,000
$1.2M – $3.1M
Confidence Low
List vs. estimate
$695K below estimate
List $1,150,000 · -37.7%
Our model says this listing is priced below recent comparable activity. Expect competition.
Price per sq ft
$440
-30.7% vs. city median $635
Based on
22 MLS comparables
Median of recent comparable listings. Sold comps use closing price, active listings use list price.

Highlights

Annual tax
$10,319
2025
Pool
Heated
View
Water
Waterfront
Lake Front
Garage
2 car garage
Furnished
Negotiable
Pets
Allowed
All facts and features
  • Flooring

    • Tile

    Heating

    • Central

    • Electric

    Cooling

    • Central Air

    Appliances

    • Dishwasher

    • Disposal

    • Dryer

    • Gas Water Heater

    • Microwave

    • Range

    • Range Hood

    • Refrigerator

    • Tankless Water Heater

    • Washer

    • Wine Refrigerator

    Other interior features

    • Cathedral Ceiling(s)

    • Ceiling Fan(s)

    • Eating Space In Kitchen

    • High Ceilings

    • Open Floorplan

    • Primary Bedroom Main Floor

    • Solid Surface Counters

    • Thermostat

    • Walk-In Closet(s)

    • Window Treatments

    Bedrooms and bathrooms

    • Bedrooms: 3

    • Bathrooms: 1

    • Full bathrooms: 3

  • Parking

    • Garage Door Opener

    Property

    • Levels: One

    • Exterior Features: Sidewalk / Sliding Doors

    Other Property Information

    • Parcel Number: 0004121038

    • Zoning: MUC1

  • Type and style

    • Property Type: Residential

    • Property Sub Type: Condominium

  • Utility

    • Electricity Connected

    • Sewer Connected

    • Underground Utilities

    • Water Connected

  • Other financial information

    • Annual tax amount: $10,320

  • Source details

    • MLS ID: A4695005

    Other facts

    • Construction Materials: Wood Frame

    • Foundation Details: Slab

    • Fireplace Features: Gas

    • Laundry Features: Laundry Room

    • Patio And Porch Features: Rear Porch

    • Pool Features: Heated / In Ground

    • Window Features: Blinds / Window Treatments

    • Direction Faces: East

    • Architectural Style: Other

    • Waterfront: Yes

    • Fireplace: Yes

    • Garage Spaces: 2

    • Attached Garage: Yes

    • Garage: Yes

    • Living Area: 2608

    • Water Source: Public

    • Subdivision Name: WINDING OAKS

Private inquiry
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The multiple listing information is provided by the Stellar MLS from a copyrighted compilation of listings. The compilation of listings and each individual listing are ©2026-present Stellar MLS. All Rights Reserved. The information provided is for consumers' personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Listing courtesy of: COLDWELL BANKER REALTY