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3460 WINDING OAKS DR #38,  LONGBOAT KEY, FL 34228

MLS# A4695005.  3 beds.  3.5 baths.  Condo.  Active

$10,320 in taxes (2025)

$1,150,000

 

Remarks:

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.

Quick Info:

  • Listing is courtesy Of: COLDWELL BANKER REALTY ((941-383-6411))
  • Listing Agent: Bruce Myer ((941-376-5311))
  • Days on yellowkey: 8
  • Property Type: Condo
  • Beds: 3
  • Baths: 3.5
  • Living Area Square Feet: 2608
  • Built 1988
  • Taxes: $10,320 (2025)
  • Spa: Yes
  • Garage Spaces:2 ()
  • Square Feet: 3323
  • Fees: $0
  • Sarasota County
  • Terms: Cash, Conventional
  • Subdivision Info:
  • Occupancy Information: Owner
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  • Subdivision Name: WINDING OAKS
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  • Interior Features: 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
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  • Parking Description: Garage Door Opener
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  • View:Water
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History:

DateListing TypeDays on yellowkeyMLS#EventPrice% Chg$/sqftSource
6/2/2026Sale8A4695005listed for sale$1,150,000-346.0728MLS




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