$1,150,000
Off-Market Date: 05/30/20263427 Winding Oaks Drive #14 Longboat Key, FL 34228
Pending MLS# A4686623
3 beds 3 baths 2,555 sq ft Condo
Details for 3427 Winding Oaks Drive #14
MLS# A4686623
Description for 3427 Winding Oaks Drive #14, Longboat Key, FL, 34228
Under contract-accepting backup offers. 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.
Listing Information
Property Type: Residential, Condominium
Status: Pending
Bedrooms: 3
Bathrooms: 3
Square Feet: 2,555 sq ft
Year Built: 1988
Garage: Yes
Stories: 1 Story
Construction: HardiPlank Type
Construction Display: New Construction
Subdivision: Winding Oaks
Foundation: Slab
County: Sarasota
Construction Status: New Construction
School Information
Elementary: Southside Elementary
Room Information
Main Floor
Laundry: 11x5
Porch: 46x29
Porch: 15x11
Porch: 10x10
Dining Room: 21x13
Living Room: 19x15
Kitchen: 31x19
Bedroom 3: 15x12
Bedroom 2: 14x14
Primary Bedroom: 15x20
Bathrooms
Full Baths: 3
Additonal Room Information
Laundry: Laundry Room, Inside
Interior Features
Appliances: Electric Water Heater, Built-In Oven, Wine Refrigerator, Washer, Microwave, Refrigerator, Cooktop, Dishwasher, Dryer
Flooring: Luxury Vinyl,Tile
Doors/Windows: Blinds, Window Treatments
Fireplaces: Living Room, Gas, Wood Burning
Additional Interior Features: Eat-In Kitchen, Walk-In Closet(s), Split Bedrooms, Ceiling Fan(s), Window Treatments, Built-in Features, High Ceilings, Living/Dining Room, Open Floorplan, Main Level Primary, Solid Surface Counters, Stone Counters
Utilities
Water: Public
Sewer: Public Sewer
Other Utilities: Electricity Connected,Natural Gas Available,Sewer Connected,Underground Utilities,Water Connected
Cooling: Ceiling Fan(s), Central Air
Heating: Gas, Electric, Central
Exterior / Lot Features
Attached Garage: Attached Garage
Garage Spaces: 2
Parking Description: Garage, driveway, Garage Door Opener, Deeded
Roof: Tile
Pool: Community, Heated, Association, In Ground, Gunite
Lot View: Golf Course,Lake,Pond,Water
Additional Exterior/Lot Features: Sprinkler/Irrigation, Awning(s), Lighting, Screened, Covered, Deck, Patio, Front Porch, Rear Porch, Landscaped, Buyer Approval Required
Waterfront Details
Water Front Features: Lake Privileges, Pond, Lake Front
Community Features
Community Features: Gated, Pool, Golf, Sidewalks, Lake
Security Features: Gated Community, Gated with Guard
Association Amenities: Pool, Tennis Court(s), Spa/Hot Tub, Maintenance Grounds
HOA Dues Include: Maintenance Grounds, Insurance, Association Management, Maintenance Structure, Pool(s), Pest Control, Reserve Fund, Road Maintenance, Security
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.
Financial Considerations
Terms: Cash,Conventional,VA Loan
Tax/Property ID: 0004121014
Tax Amount: 13849.79
Tax Year: 2025
A broker reciprocity listing courtesy: COLDWELL BANKER REALTY
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Copyright 2026 Stellar MLS as distributed by the MLS GRID. All Rights Reserved.
Sales History & Tax Summary for 3427 Winding Oaks Drive #14
Sales History
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Tax Summary
| Tax Year | Estimated Market Value | Total Tax |
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
Schools
Schools nearby 3427 Winding Oaks Drive #14
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
The schools shown represent both the assigned schools and schools by distance based on local school and district attendance boundaries. Attendance boundaries change based on various factors and proximity does not guarantee enrollment eligibility. Please consult your real estate agent and/or the school district to confirm the schools this property is zoned to attend. Information is deemed reliable but not guaranteed.
SchoolDigger ® Rating
The SchoolDigger rating system is a 1-5 scale with 5 as the highest rating. SchoolDigger ranks schools based on test scores supplied by each state's Department of Education. They calculate an average standard score by normalizing and averaging each school's test scores across all tests and grades.
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