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Coastal

3427 WINDING OAKS DRIVE 14

LONGBOAT KEY , FL 34228

MLS#: A4686623

$1,150,000

Status: Active
Listing number: A4686623
Listing provided by: COLDWELL BANKER REALTY
Listing agent phone: None
Last update: an hour ago
New on site 1 day ago
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WINDING OAKS - Residential

Property

Beds

3

Full Baths

3

1/2 Baths

None

Year Built

1988

Sq.Footage

2,555

Privately tucked away within the private Winding Oaks community on Longboat Key, this beautifully updated three-bedroom villa offers an easy, elevated way to enjoy Sarasota’s coastal lifestyle. Overlooking the Harbourside Golf Course, the home captures peaceful water views and the scenic 5th hole, creating a backdrop that feels both open and serene. Designed for effortless living, this turnkey furnished residence blends the comfort of a single-family home with the simplicity of maintenance-free ownership—ideal for seasonal stays or extended escapes. Inside, an airy open layout, soaring ceilings, and wide-plank tile floors create a light, welcoming feel, while floor-to-ceiling sliders connect seamlessly to the outdoor living spaces. The kitchen is both stylish and functional, featuring Italian white-lacquer cabinetry, stone countertops, and premium appliances—perfect for casual evenings at home or hosting friends. The living room centers around a custom gas fireplace and flows naturally to a spacious screened lanai, where you can unwind with long water views and soft coastal breezes. The home features many new furnishings and many recent updates. A private courtyard with a heated pool adds another layer of relaxation, offering a quiet place to start the day or wind down after time on the water, golf course or tennis courts. The primary suite is a calm retreat of its own, with tranquil water views, a spa-like bath, and a generous walk-in closet. Two additional en-suite bedrooms provide flexibility for visiting guests or a comfortable home office. Ownership includes access to the Bay Isles Beach Club, where days can be spent on pristine Gulf-front sands with thoughtfully appointed amenities. Within Winding Oaks, residents enjoy a recently refreshed community pool, walking paths, and a secure, gated setting. Optional golf, tennis and social memberships are available at the Longboat Key Club. Just minutes from dining and shopping on world-renowned St. Armands Circle and the cultural amenities of downtown Sarasota, this retreat makes it easy to step into the best of the area—while always having a peaceful place to return to. Simple, sophisticated, and distinctly Longboat Key.

Features & Amenities

Interior

  • Other Interior Features

    Built-in Features, Eat-in Kitchen, High Ceilings, Open Floorplan, Stone Counters, Walk-In Closet(s)

  • Total Bedrooms

    3

  • Bathrooms

    3

  • Cooling YN

    YES

  • Cooling

    Central Air

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Central, Electric

  • Pet friendly

    Cats OK, Dogs OK, Number Limit, Yes

Exterior

  • Garage

    Yes

  • Garage spaces

    2

  • Construction Materials

    HardiPlank Type

  • Other Exterior Features

    Awning(s), Lighting

  • Parking

    Deeded, Driveway, Garage Door Opener, Attached

  • Patio and Porch Features

    Covered, Deck, Front Porch, Patio, Rear Porch, Screened

  • Pool

    Yes

  • Pool Features

    Gunite, Heated, In Ground, Private

  • Waterfront YN

    YES

  • View

    Lake, Pond, Water, Golf Course

Area & Lot

  • Lot Features

    Waterfront

  • Property Type

    Residential

  • Property Sub Type

    Condominium

  • Architectural Style

    Coastal

Price

  • Sales Price

    $1,150,000

  • Tax Amount

    $13,849.79

  • Sq. Footage

    2, 555

  • Price/SqFt

    $450

HOA

  • Association

    Yes

  • Association Fee 2

    $2,040.05

  • Association Fee Frequency

    Quarterly

  • Association Fee 2 Frequency

    Annually

  • Association Fee Includes

    N/A

  • Total Monthly Fees

    $2,398

School District

  • Elementary School

    Southside Elementary

  • Middle School

    N/A

  • High School

    N/A

Property Features

  • Stories

    1

  • Association Amenities

    Maintenance, Pool, Spa/Hot Tub, Tennis Court(s)

  • Foundation Details

    Slab

  • Ownership

    Fee Simple

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Tax Lot

    14

  • Water Source

    Public

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Location

County

Sarasota

Elementary School

Southside Elementary

Middle School

High School

Listing Courtesy of Carolyn Donnelly, PA , COLDWELL BANKER REALTY

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Privately tucked away within the private Winding Oaks community on Longboat Key, this beautifully updated three-bedroom villa offers an easy, elevated way to enjoy Sarasota’s coastal lifestyle. Overlooking the Harbourside Golf Course, the home captures peaceful water views and the scenic 5th hole, creating a backdrop that feels both open and serene. Designed for effortless living, this turnkey furnished residence blends the comfort of a single-family home with the simplicity of maintenance-free ownership—ideal for seasonal stays or extended escapes. Inside, an airy open layout, soaring ceilings, and wide-plank tile floors create a light, welcoming feel, while floor-to-ceiling sliders connect seamlessly to the outdoor living spaces. The kitchen is both stylish and functional, featuring Italian white-lacquer cabinetry, stone countertops, and premium appliances—perfect for casual evenings at home or hosting friends. The living room centers around a custom gas fireplace and flows naturally to a spacious screened lanai, where you can unwind with long water views and soft coastal breezes. The home features many new furnishings and many recent updates. A private courtyard with a heated pool adds another layer of relaxation, offering a quiet place to start the day or wind down after time on the water, golf course or tennis courts. The primary suite is a calm retreat of its own, with tranquil water views, a spa-like bath, and a generous walk-in closet. Two additional en-suite bedrooms provide flexibility for visiting guests or a comfortable home office. Ownership includes access to the Bay Isles Beach Club, where days can be spent on pristine Gulf-front sands with thoughtfully appointed amenities. Within Winding Oaks, residents enjoy a recently refreshed community pool, walking paths, and a secure, gated setting. Optional golf, tennis and social memberships are available at the Longboat Key Club. Just minutes from dining and shopping on world-renowned St. Armands Circle and the cultural amenities of downtown Sarasota, this retreat makes it easy to step into the best of the area—while always having a peaceful place to return to. Simple, sophisticated, and distinctly Longboat Key.

3427 WINDING OAKS DRIVE 14

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