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$1,135,000

  • Sold
  • Closed
  • Condo
  • 3 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2,608 Sq. Ft.
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Tucked within Winding Oaks, one of Longboat Key's most sought-after villa communities, this 3BR/3BA residence offers the scale and comfort of a single-family home paired with the simplicity of maintenance-free living. From the paver drive and walkway to the stepped front entry, the residence creates an inviting first impression before opening into a home defined by volume, light and connection to the outdoors. Step inside and soaring ceilings immediately create a sense of openness, while high-set windows invite natural light to move throughout the living spaces. Tile flooring and soft neutral tones create a clean backdrop that complements the peaceful setting just beyond the glass. Renovated in November 2025, the kitchen has been thoughtfully opened and redesigned into a true centerpiece for gathering and everyday living. A substantial island with seating anchors the space, along with stone countertops, white cabinetry, stainless steel appliances, a range hood, wine refrigerator and tile backsplash. An abundance of windows and an adjoining sitting area create a bright, welcoming space whether hosting guests or enjoying a quiet morning. The dining area transitions naturally into the living room, where cathedral ceilings, a corner fireplace and sliding glass doors connect the interior to the outdoors. Beyond, an expansive screened deck overlooks the community lake and fountain, creating a peaceful setting with multiple areas for dining, relaxing or entertaining. Privacy walls on either side enhance the feeling of seclusion while keeping the water views front and center. The primary suite is spacious and calming, featuring vaulted ceilings, engineered wood floors, a wall of sliding glass doors opening to the deck and a large walk-in closet with extensive built-ins. Also renovated in November 2025, the primary bath offers dual vanities, a walk-in shower, dressing area and separate water closet. Guest accommodations are equally well planned. One bedroom includes an en suite bath and walk-in closet, while another is currently configured as an office space with sliding glass doors opening to a private patio. Updated baths throughout, an in-residence laundry room and a 2-car garage add convenience. Set within the Harbourside golf course community, Winding Oaks offers a serene environment with a gated entrance, community pool and spa, and access to the full range of Bay Isles amenities, including deeded beach access through the private Bay Isles Beach Club.

Full Property Details for 3460 Winding Oaks Dr #38

General

  • Sold For: $1,135,000
  • HOA FEE: $2,228/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $10,319 (2025)
  • Status: Closed
  • Type: Condo
  • Source: MidFloridaRegionalMLS
  • MLS ID: A4695005
  • Added to Site: 108 day(s) ago

Rental Information

  • Min. Lease: 3 Months

Interior

  • Number of Rooms: 7
  • Interior Features: Cathedral Ceiling(s), Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Thermostat, Walk-In Closet(s), Window Treatments
  • Fireplace: Yes
  • Fireplace(s): Gas
  • Appliances: Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
  • Furnishings: Negotiable
  • Flooring: Tile

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Shared Amenities: Maintenance, Pool
  • Pool Description: Heated, In Ground
  • Spa: Yes
  • Spa Description: Heated, In Ground

Exterior

  • Exterior Features: Sidewalk, Sliding Doors
  • Deck/Patio: Rear Porch
  • Porch/Patio/Deck: Rear Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Garage Door Opener

Location

  • Area: 34228 - Longboat Key
  • County: Sarasota
  • Development Name: 34228 - Longboat Key
  • Subdivision: WINDING OAKS
  • Driving Directions: Start at St. Armands Circle. Take N Boulevard of the Presidents north. Continue onto John Ringling Parkway. Cross onto Gulf of Mexico Drive. Stay on Gulf of Mexico Drive north. Turn right on Bay Isles Parkway. Stop at the Bay Isles security gate. Continue to Winding Oaks Drive. Follow it to 3460 Winding Oaks Drive.
  • Direction Faces: East

Community

  • Community Name: 34228 - Longboat Key
  • Community Features: Buyer Approval Required, Deed Restrictions, Pool
  • Optional Amenities: Maintenance, Pool
  • Assoc. Name: Advanced Management - AMI / Neil Fleet
  • Assoc. Fees Include: 24-Hour Guard, Community Pool, Manager, Private Road
  • 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: Other
  • Architectural Style: Other
  • Exterior Const.: Wood Frame
  • Roof: Tile
  • Windows: Blinds, Window Treatments
  • Stories/Levels: One
  • Square Feet: 2,608
  • Sq. Ft. Source: Public Records
  • Living Area: 2,608 Sq. Ft.
  • Year Built: 1988

Lot Features

  • Property View: Water
  • Street/Road Desc.: Paved

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Access: Yes
  • Water Access Desc: Lake
  • Water Front Desc.: Lake Front

Financial Considerations

  • Condo Fee: $6,685
  • Condo Fee Freq: Quarterly
  • Tax Amount: $10,319.57
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: UNIT 38 WINDING OAKS
  • Flood Zone Info: AE
  • APN: 4121038
  • Property ID: 4121038

Meet the listing agent

Meet the listing agent
— 3460 Winding Oaks Dr #38 —

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 3460 Winding Oaks Dr #38

School District:Sarasota County School District
NameGradesDistance
Southside Elementary School, Sarasota, FL
1901 Webber Street, Sarasota, FL 34239
PK-57.4 mi
Booker Middle School
2250 Myrtle Street, Sarasota, FL 34234
6-86.1 mi
Booker High School
3201 North Orange Avenue, Sarasota, FL 34234
9-125.2 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 3460 Winding Oaks Dr #38

Date
Details
Price
Change
Source
8/31/2026
Sold
$1,135,000
-1.3%
MLS
6/02/2026
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.

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3460 Winding Oaks Drive #38, Longboat Key, FL 34228 (MLS# A4695005) is a Condo property that was sold at $1,135,000 on August 31, 2026. This property was listed by Bruce Myer Group from our Longboat Key Office.Want to learn more about 3460 Winding Oaks Drive #38? 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.