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$1,100,000
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Property Description
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.
Full Property Details
Full Property Details for 3427 Winding Oaks Dr #14
General
- Sold For: $1,100,000
- HOA FEE: $2,228/month
- HOA FEE FREQ.: Quarterly
- Taxes: $13,849 (2025)
- Status: Closed
- Type: Condo
- Source: MidFloridaRegionalMLS
- MLS ID: A4686623
- Added to Site: 102 day(s) ago
Rental Information
- Min. Lease: 3 Months
Interior
- Number of Rooms: 10
- Interior Features: Built-in Features, Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s), Window Treatments
- Fireplace: Yes
- Fireplace(s): Gas, Living Room, Wood Burning
- Appliances: Built-In Oven, Cooktop, Dishwasher, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer, Wine Refrigerator
- Furnishings: Turnkey
- Flooring: Luxury Vinyl, Tile
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Inside, Laundry Room
Additional Information
- Shared Amenities: Maintenance, Pool, Spa/Hot Tub, Tennis Court(s)
- Pool: Yes
- Private Pool: Yes
- Pool Description: Gunite, Heated, In Ground
- Security/Safety: Gated Community
Exterior
- Exterior Features: Awning(s), Irrigation System, Lighting, Sliding Doors
- Deck/Patio: Covered, Deck, Front Porch, Patio, Rear Porch, Screened
- Porch/Patio/Deck: Covered, Deck, Front Porch, Patio, Rear Porch, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Covered Spaces: 2
- Parking Features: Deeded, Driveway, Garage Door Opener
Location
- Area: 34228 - Longboat Key
- County: Sarasota
- Development Name: 34228 - Longboat Key
- Subdivision: WINDING OAKS
- Driving Directions: North on Gulf of Mexico Drive to the light at Bay Isles Parkway. Turn right into Bay Isles, go to gatehouse, continue on Harbourside Drive to Winding Oaks on right.
- Direction Faces: West
School Information
- Elementary School: Southside Elementary
Community
- Community Name: 34228 - Longboat Key
- Community Features: Lake, Buyer Approval Required, Deed Restrictions, Gated Community - Guard, Golf, Pool, Sidewalks
- Optional Amenities: Maintenance, Pool, Spa/Hot Tub, Tennis Court(s)
- Association: Yes
- Assoc. Name: Winding Oaks/Neil Fleet
- Assoc. Fees Include: 24-Hour Guard, Community Pool, Escrow Reserves Fund, Insurance, Maintenance Structure, Maintenance Grounds, Manager, Pest Control, Private Road, Security
- Number of Pets: 2
- Pet Restrictions: One cat and one dog, or one dog (or two dogs if each are under 25 lbs.), or two cats., / 100lbs.
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric, Natural Gas
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Electricity Connected, Natural Gas Available, Sewer Connected, Underground Utilities, Water Connected
Structural Information
- Architectural Info: Coastal
- Architectural Style: Coastal
- Exterior Const.: HardiPlank Type
- Roof: Tile
- Windows: Blinds, Shades, Window Treatments
- Stories/Levels: One
- Square Feet: 2,555
- Sq. Ft. Source: Public Records
- Living Area: 2,555 Sq. Ft.
- Year Built: 1988
Lot Features
- Property View: Golf Course, Water
- Street/Road Desc.: Paved
Water Features
- Water Front: Yes
- Water View: Yes
- Water Access: Yes
- Water Access Desc: Lake, Pond
- Water Front Desc.: Lake, Lake Front, Pond
Financial Considerations
- Assoc Fee Freq.: Quarterly
- Assoc Fee Desc.: Required
- Condo Fee: $6,684
- Condo Fee Freq: Quarterly
- Tax Amount: $13,849.79
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: UNIT 14 WINDING OAKS
- Flood Zone Info: AE, X
- APN: 4121014
- Property ID: 4121014
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Schools
Schools serving 3427 Winding Oaks Dr #14
School District:Sarasota County School District
| Name | Grades | Distance |
|---|---|---|
Southside Elementary School, Sarasota, FL 1901 Webber Street, Sarasota, FL 34239 | PK-5 | 7.3 mi |
Booker Middle School 2250 Myrtle Street, Sarasota, FL 34234 | 6-8 | 6 mi |
Booker High School 3201 North Orange Avenue, Sarasota, FL 34234 | 9-12 | 5.1 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 3427 Winding Oaks Dr #14
Date
Details
Price
Change
Source
6/18/2026
Sold
$1,100,000
-4.35%
MLS
3/23/2026
Listed
$1,150,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
3427 Winding Oaks Drive #14, Longboat Key, FL 34228 (MLS# A4686623) is a Condo property that was sold at $1,100,000 on June 18, 2026. This property was listed by Carolyn Donnelly from our Longboat Key Office.Want to learn more about 3427 Winding Oaks Drive #14? Do you have questions about finding other Condo real estate for sale in Longboat Key? You can browse all Longboat Key real estate or contact a Coldwell Banker agent to request more information.


