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$1,150,000

3460 Winding Oaks Drive Longboat Key, FL 34228 Residential - Condominium Active

  • 3460 Winding Oaks Drive, Unit 38, Longboat Key, FL 34228 Main Photo

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Description

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.

Property Highlights

Property Type: Residential - Condominium
Cooling: Central Air
Garage: 2 car attached
Heating: Central, Electric
Roof Type: Tile
Stories: 1.0
Taxes: $10,319
Year Built: 1988

General Information

Bedrooms: 3
Bathrooms: 3 Full 1 Half
Sqft: 2,608
County: Sarasota
Subdivision: WINDING OAKS
Listed By:
Bruce Myer COLDWELL BANKER REALTY 941-383-6411

Amenities

Cathedral Ceiling(s)
Ceiling Fans(s)
Eat-in Kitchen
High Ceilings
Open Floorplan
Primary Bedroom Main Floor
Solid Surface Counters
Thermostat
Walk-In Closet(s)
Window Treatments
Sidewalk
Sliding Doors

Room Information

Living Room: 22x29
Kitchen: 15x23
Balcony/Porch/Lanai: 45x23
Primary Bedroom: 14x17
Bedroom 2: 14x14
Bedroom 3: 15x14
Laundry: 7x5

Property Features

Appliances: Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
Association Amenities: Maintenance, Pool
Community Features: Buyer Approval Required, Deed Restrictions, Pool
Condo Fee: $6685/ Quarterly
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
Exterior: Frame
Fireplace: Gas
Fireplace Y/N: Yes
Flood Zone Code: AE
Flooring: Tile
Foundation: Slab
Frontage Lake: 1
Home Warranty Y/N: No
Listing Terms: Cash, Conventional
Number of Pets: 2
Ownership: Fee Simple
Parking: Garage Door Opener
Parking Notes: Garage Door Opener
Patio/Porch: Rear Porch
Pets Allowed: Yes
Pets Restrictions: See Documents
Pets Size: Extra Large (101+ Lbs.)
Pets Weight (Max): 100
Pool: Heated, In Ground
Property Attached Y/N: No
Property Sub-Type: Condominium
Sewer: Public Sewer
Showing Instructions: Listing Agent Must Accompany, ShowingTime
Spa: Heated, In Ground
Special Sale Provisions: None
Special View Info: Water
Utilities: Electricity Connected, Sewer Connected, Underground Utilities, Water Connected
Vegetation: Mature Landscaping
Water: Public
Water Access: Lake
Water Access Y/N: Yes
Waterfront Features: Lake Front
Water View: Lake
Windows: Blinds, Window Treatments
Zoning: MUC1
$1,150,000
3beds
3.5baths
2,608sqft
2cars
New to the Market Active
BEDS3 BATHS3 full 1 partial SQUARE FEET2,608 MLS#A4695005
STATUSActive PROPERTY TYPEResidential - Condominium SUBDIVISIONWINDING OAKS

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3460 Winding Oaks Drive, Unit 38, Longboat Key, FL 34228.

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Estimated Payment

$ 5,074.09 per month $3,878.76 Principal & Interest $859.92 Property Tax $335.42 Homeowner's Insurance

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About this area

Florida/Longboat Key
Longboat Key

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About Longboat Key

Longboat Key, FL recently was named one of Condé Nast's Top Ten Traveler’s Islands. Longboat Key possesses something uniquely its own. There is a natural beauty and elegance to Longboat Key that entrances visitors and residents, and in many ways it’s the perfect beach getaway. Those that live there have stunning scenery, a luxurious vibe, and easy access to places like Sarasota, Bradenton, and Tampa.


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About this community

Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 06/03/2026. The listing information on this page last changed on 06/03/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Wed 06/03/2026 12:45:58 AM EST) or Stellar MLS (last updated Wed 06/03/2026 12:28:57 AM EST). Real estate listings held by brokerage firms other than Wagner Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.

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