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Active Condo

3435 WINDING OAKS DRIVE 18

Longboat Key, FL 34228

STELLAR #A4680403 Updated: Jun 2, 2026, 1:08pm
$949,000
3 Beds • 3 Baths • 2,555 SqFt
Property
ActiveCondo
1/60
$949,000

3435 WINDING OAKS DRIVE 18

Longboat Key, FL 34228
3
Beds
3
Baths
2,555
SqFt
13.84
Acres
STELLAR
#A4680403
Updated: Jun 2, 2026, 1:08pm

Property Description

Own your own slice of tropical paradise on Longboat Key with this beautiful two bedroom two and on half bath Villa in the exclusive Winding Oaks Community located behind the gates of Bay Isles Association. Sweeping views of the Longboat Key Club Harbourside Golf Course and a sparkling inland waterway from your primary bedroom and expansive living/dining room combo that both exit through sliders to a fully enclosed wrap around deck to further enhance your tropical lifestyle. Open floor plan with soaring ceilings and enclosed atrium help to maximize the natural light and make the 2,555 sq feet feel even larger.

Beautifully updated eat in kitchen with striking tray ceiling, ample pantry storage, bright white cabinets, quartz countertops and stainless steel appliances.

Primary owners suite includes an designer walk in closet, updated bath with ceramic tile, walk in shower, double sinks and quartz counter tops.
Split layout offers a private guest suite, with walk in closet, updated ensuite bathroom with ceramic tile, walk in shower and quartz counter tops. Large office with desk nook could easily be converted to another bedroom. Laundry room with storage and sink adjacent to large 2 car garage with epoxy floors and storage cabinets.

Meticulously maintained, Impact Windows and sliders throughout, low maintenance mature plantings in private enclosed front courtyard.

Dog friendly community. Beautiful updated community pool with bathrooms. Beach access via Bay Isles Beach Club which offers a private pavilion with bathrooms, volleyball, picnic tables, grills and ample parking. Low maintenance community where all exteriors and court yards are maintained by the association.

Conveniently located mid key, one mile from Publix and CVS and a short drive to the restaurants and shops of St Armand’s and Downtown Sarasota.
Included Appliances
Built-In OvenDishwasherDisposalDryerElectric Water HeaterMicrowaveRangeRefrigeratorWasher

Property Details

Highlights
View
Yes
Interior
Additional Rooms
Den/Library/OfficeInside Utility
Appliances
Built-In OvenDishwasherDisposalDryerElectric Water HeaterMicrowaveRangeRefrigeratorWasher
Bathrooms Total Decimal
2.5
Building Area Total
3270
Cooling
Central AirHumidity Control
Fireplace Features
Living Room
Flooring
CarpetTileVinylHardwood
Furnished
Furnished
Heating
CentralElectric
Interior Features
Ceiling Fan(s)Eating Space In KitchenLiving Room/Dining Room ComboOpen FloorplanPrimary Bedroom Main FloorSplit BedroomTray Ceiling(s)
Laundry Features
InsideLaundry Room
Living Area
2555
Rooms Total
10
Security Features
Gated CommunitySecurity GateSecurity SystemSecurity System LeasedSmoke Detector(s)
Window Features
BlindsWindow Treatments
Construction
Building Area Source
Public Records
Building Area Units
Square Feet
Common Walls
Corner Unit
Construction Materials
HardiPlank Type
Direction Faces
Southwest
Foundation Details
BlockSlab
Levels
One
Living Area Source
Public Records
Living Area Units
Square Feet
Num Of Own Years Prior To Lse
2
Num Timesper Year
2
Roof
Tile
Stories Total
Yes
Year Built
1988
Site & Exterior
Covered Spaces
2
Exterior Features
Awning(s)CourtyardGardenLightingPrivate EntrancePrivate YardSliding Doors
Fencing
Masonry
Flood Zone Code
AE
Garage Spaces
2
I D X Participation
Yes
Lot Size Acres
13.84
Lot Size Area
13.8417
Lot Size Square Feet
602945
Lot Size Units
Acres
Parking Features
Garage Door Opener
Patio And Porch Features
PatioRear PorchScreened
Public Survey Range
17E
Public Survey Section
05
Road Surface Type
Asphalt
Sewer
Public Sewer
Total Acreage
10 to less than 20
Utilities
BB/HS Internet AvailableCable AvailableElectricity ConnectedPublicSewer ConnectedUnderground UtilitiesWater Connected
View
Golf CourseWater
Water Access
Yes
Water Source
Public
Water View
Yes
Waterfront Features
Gulf/Ocean Front
Zoning
MUC1
Financials
Association Fee Includes
24-Hour GuardCable TVCommon Area TaxesCommunity PoolEscrow Reserves FundFidelity BondMaintenance StructureMaintenance GroundsPool MaintenanceRecreational FacilitiesTrash
Calculated List Price By Calculated Sq Ft
371.43
Condo Fees
6271
Condo Fees Term
Quarterly
Contract Status Change Date
2026-02-26
Current Price
949000
Feed Types
BBO
Lease Considered
Yes
Minimum Lease
3 Months
Monthly Condo Fee Amount
2090
Owner Name
ON RECORD
Ownership
Condominium
Parcel Number
0004121018
Public Survey Township
36S
Tax Annual Amount
8564.88
Tax Book Number
27-27
Tax Legal Description
UNIT 18 WINDING OAKS
Tax Lot
18
Tax Year
2025
Total Annual Fees
26006
Total Monthly Fees
2167.17
Yrs Of Owner Prior To Leasing Req
Yes

Neighborhood & Lifestyle

Community & Association
Additional Lease Restrictions
See Rules
Association Amenities
PoolVehicle Restrictions
Association Approval Required
Yes
Association Email
nfleet@amiwra.com
Association Fee2
922
Association Fee2 Frequency
Annually
Association Name
Neil Fleet
Association Name2
Bay Isle Association
Association Phone
941-383-3200
Association U R L
www.bayisles.com
Association2
Yes
Community Features
Gulf/Ocean FrontAssociation Recreation - OwnedBuyer Approval RequiredDeed RestrictionsGated Community - GuardPool
Lease Restrictions
Yes
M L S Area Major
34228 - Longboat Key
Max Pet Weight
100
Number Of Pets
2
Pet Size
Large (61-100 Lbs.)
Pets Allowed
Dogs OKSize LimitYes
S W Subdiv Community Name
Winding Oaks
Subdivision Name
WINDING OAKS
Schools
Ratings
Elementary
Southside Elementary
Middle
Booker Middle
High
Booker High
Listing provided courtesy of STELLAR via IDX. Updated: Jun 2, 2026, 1:08pm.
Sean Clark

Listing Agent

MICHAEL SAUNDERS & COMPANY

Call Agent
Call