To schedule a showing of 3460 Winding Oaks Drive UNIT #38, Longboat Key, Florida, Call David Shippey at 863-521-4517 TODAY!
$1,150,000 | 3 beds | 3 full baths | 1 half baths | 2,608 sqft
Longboat Key, FL 34228
- 3Beds
- 4.00Total Baths
- 3 Full, 1 HalfBaths
- 2,608SqFt
- 1988Year Built
- 0.00Acres
- MLS# A4695005
- Residential
- Condominium
- Active
- Approx Time on Market14 days
- Area34228 - Longboat Key
- CountySarasota
- Subdivision Winding Oaks
Overview
Tucked within Winding Oaks, one of Longboat Keys 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.
Agriculture / Farm
Association Fees / Info
Community Features: Pool, Sidewalks
Pets Allowed: Yes
Hoa Fees Frequency: Quarterly
Association Amenities: MaintenanceGrounds, Pool
Association Fee Includes: AssociationManagement, Pools, RoadMaintenance, Security
Hoa Fees: 6685
Bathroom Info
Total Baths: 4.00
Fullbaths: 3
Building Info
Window Features: Blinds, WindowTreatments
Roof: Tile
Building Area Source: PublicRecords
Buyer Compensation
Exterior Features
Style: Other
Pool Features: Heated, InGround, Association, Community
Patio: RearPorch
Fees / Restrictions
Association Fee: 1522.96
Association Fee Frequency: Annually
Financial
Original Price: $1,150,000
Disclosures: CovenantsRestrictionsDisclosure
Garage / Parking
Parking Features: Garage, GarageDoorOpener
Attached Garage: Yes
Garage: Yes
Green / Env Info
Interior Features
Fireplace Desc: Gas
Fireplace: Yes
Floors: Tile
Levels: One
Spa: Yes
Laundry Features: LaundryRoom
Interior Features: CeilingFans, CathedralCeilings, EatInKitchen, HighCeilings, MainLevelPrimary, OpenFloorplan, SolidSurfaceCounters, WalkInClosets, WindowTreatments
Appliances: Dryer, Dishwasher, Disposal, GasWaterHeater, Microwave, Range, Refrigerator, RangeHood, TanklessWaterHeater, WineRefrigerator, Washer
Spa Features: Heated, InGround
Lot Info
Direction Remarks: 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.
Lot Size Units: Acres
Lot Desc: BuyerApprovalRequired, Landscaped
Misc
Other
Special Conditions: None
Other Rooms Info
Property Info
Section: 05
Class Type: Condominium
Property Sub Type: Condominium
Property Condition: NewConstruction
Construction Materials: WoodFrame
Stories: 1
Total Stories: 1
Foundation: Slab
Human Modified: Yes
Room Info
Total Rooms: 7
Sqft Info
Sqft: 2,608
Bulding Area Sqft: 3,323
Living Area Units: SquareFeet
Living Area Source: PublicRecords
Tax Info
Tax Year: 2,025
Tax Lot: 38
Tax Legal Description: UNIT 38 WINDING OAKS
Tax Annual Amount: 10319.57
Tax Book Number: 27-27
Unit Info
Unit: 38
Utilities / Hvac
Heating: Central, Electric
Water Source: Public
Sewer: PublicSewer
Cool System: CentralAir, CeilingFans
Cooling: Yes
Heating: Yes
Utilities: ElectricityConnected, SewerConnected, UndergroundUtilities, WaterConnected
Waterfront / Water
Waterfront: Yes
Waterfront Features: LakeFront, LakePrivileges
View: Yes
View: Lake, Water
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.This listing courtesy of Coldwell Banker Realty
MLS# A4675109 
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MLS IDX data last updated on 06-16-2026 7:58 PM EST.
If you have any questions on 3460 Winding Oaks Drive UNIT #38, Longboat Key, Florida, please call David Shippey at 863-521-4517.
MLS# A4695005 located at 3460 Winding Oaks Drive UNIT #38, Longboat Key, Florida is brought to you by David Shippey REALTOR®
3460 Winding Oaks Drive UNIT #38, Longboat Key, Florida has 3 Beds, 3 Full Bath, and 1 Half Bath.
The MLS Number for 3460 Winding Oaks Drive UNIT #38, Longboat Key, Florida is A4695005.
The price for 3460 Winding Oaks Drive UNIT #38, Longboat Key, Florida is $1,150,000.
The status of 3460 Winding Oaks Drive UNIT #38, Longboat Key, Florida is Active.
The subdivision of 3460 Winding Oaks Drive UNIT #38, Longboat Key, Florida is Winding Oaks.
The home located at 3460 Winding Oaks Drive UNIT #38, Longboat Key, Florida was built in 2026.