3427 Winding Oaks Drive Unit 14, Longboat Key, FL 34228
- $1,100,000
- 3
- BD
- 3
- BA
- 2,555
- SqFt
- Sold Price
- $1,100,000
- List Price
- $1,150,000
- Status
- Sold
- Days on Market
- 68
- Closing Date
- Jun 18, 2026
- MLS#
- A4686623
- Property Style
- Condo
- Architectural Style
- Coastal
- Year Built
- 1988
- Bedrooms
- 3
- Bathrooms
- 3
- Living Area
- 2,555
- Price per sq. ft.
- 450.1
- Total Acreage
- Non-Applicable
- Building Name
- #14
- Monthly Condo Fee
- 2228
- Legal Subdivision Name
- Winding Oaks
- Community Name
- Winding Oaks
- MLS Area Major
- Longboat Key
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.
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Additional Information
- Taxes
- $13849
- Minimum Lease Period
- 3 Months
- Max Times per Year
- 2
- HOA Payment Schedule
- Quarterly
- Maintenance Includes
- Guard - 24 Hour, Pool, Escrow Reserves Fund, Insurance, Maintenance Structure, Maintenance Grounds, Management, Pest Control, Private Road, Security
- Condo Fees
- $6684
- Condo Fees Term
- Quarterly
- Community Features
- Buyer Approval Required, Deed Restrictions, Gated Community - Guard, Golf, Pool, Sidewalks, Golf Community, Maintenance Free
- Property Description
- One Story
- Zoning
- MUC1
- Interior Features
- Built-in Features, Ceiling Fans(s), Eat-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
- Floor
- Luxury Vinyl, Tile
- Appliances
- Built-In Oven, Cooktop, Dishwasher, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer, Wine Refrigerator
- Utilities
- Electricity Connected, Natural Gas Available, Sewer Connected, Underground Utilities, Water Connected
- Heating
- Central, Electric, Natural Gas
- Air Conditioning
- Central Air
- Fireplace
- Yes
- Fireplace Description
- Gas, Living Room, Wood Burning
- Exterior Construction
- HardiPlank Type
- Exterior Features
- Awning(s), Lighting, Sliding Doors
- Roof
- Tile
- Foundation
- Slab
- Pool
- Community, Private
- Pool Type
- Gunite, Heated, In Ground
- Garage Carport
- 2 Car Garage
- Garage Spaces
- 2
- Garage Features
- Deeded, Driveway, Garage Door Opener
- Elementary School
- Southside Elementary
- Water View
- Lake, Pond
- Water Access
- Lake, Pond
- Water Frontage
- Lake Front, Pond
- Pets
- Allowed
- Max Pet Weight
- 100
- Pet Size
- Large (61-100 Lbs.)
- Floor Number
- 1
- Flood Zone Code
- AE, X
- Parcel ID
- 0004121014
- Legal Description
- UNIT 14 WINDING OAKS
Listing courtesy of COLDWELL BANKER REALTY. 941-383-6411
Selling Office: MICHAEL SAUNDERS & COMPANY.Mortgage Calculator
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