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$1,150,000 Just Listed

  • For Sale
  • Active
  • Condo
  • 3 Beds
  • 3 Full Baths
  • 2,555 Sq. Ft.
  • Updated 2 hours ago
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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. Both the living room and lanai feature brand new furnishings. 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 for 3427 Winding Oaks Dr #14

General

  • Price: $1,150,000
  • HOA FEE: $2,228/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $13,849 (2025)
  • Status: Active
  • Type: Condo
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4686623
  • Updated: Today (3/23/2026)
  • Added to Site: Today

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, Pool Maintenance, Private Road, Security
  • Number of Pets: 2
  • Pet Restrictions: See Documents, / 100lbs.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Electricity Connected, 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
  • 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
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

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— 3427 Winding Oaks Dr #14 —

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NMLS#: 1598647

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NMLS#: 1598647

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Schools serving 3427 Winding Oaks Dr #14

School District:Sarasota County School District
NameGradesDistance
Southside Elementary School, Sarasota, FL
1901 Webber Street, Sarasota, FL 34239
PK-57.3 mi
Booker Middle School
2250 Myrtle Street, Sarasota, FL 34234
6-86 mi
Booker High School
3201 North Orange Avenue, Sarasota, FL 34234
9-125.1 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 Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/23/2026
Listed
$1,150,000
-3.77%
MLS
3/07/2025
Sold
$1,195,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 3427 Winding Oaks Dr #14

Year
Property Taxes
Change
Tax Assessment
Change
2025
$13,583
1%
$1,064,600
-2%
2024
$13,423
4%
$1,090,200
1%
2023
$12,917
27%
$1,083,000
52%
2021
$10,181
-17%
$714,000
-31%
2022
$12,220
20%
$1,032,700
51%
2021
$10,181
9%
$683,100
—
2019
$9,378
18%
$685,343
18%
2018
$7,953
19%
$582,500
19%
2017
$6,682
—
$489,834
2%
2016
$6,657
1%
$479,759
1%
2015
$6,586
—
$476,424
1%
2014
$6,580
2%
$472,643
2%
2013
$6,434
—
$465,658
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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3427 Winding Oaks Drive #14, Longboat Key, FL 34228 (MLS# A4686623) is a Condo property with 3 bedrooms and 3 full bathrooms. 3427 Winding Oaks Drive #14 is currently listed for $1,150,000 and was received on March 23, 2026. This property is 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.

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