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You are here: Home / 3435 WINDING OAKS DRIVE 18, LONGBOAT KEY, FL, 34228

3435 WINDING OAKS DRIVE 18, LONGBOAT KEY, FL, 34228

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$1,150,000
New Listing

3435 WINDING OAKS DRIVE 18
LONGBOAT KEY, FL 34228

For Sale|Townhouse|Active
2
Beds
3
Total Baths
2
Full Baths
1
Partial Bath
2,555
SqFt
$450
/SqFt
1988
Built
Subdivision:
WINDING OAKS
County:
Sarasota
Call Now: 941-421-7375
Is this the listing for you? We can help make it yours.
941-421-7375
3435 WINDING OAKS DRIVE 183435 WINDING OAKS DRIVE 183435 WINDING OAKS DRIVE 183435 WINDING OAKS DRIVE 18
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Monthly Payment (Est.)

$5,247
Calculator powered by Showcase IDX, a Constellation1 Company. Copyright ©2026 Information is deemed reliable but not guaranteed.
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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.

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Listing Snapshot
Price 
$1,150,000
Days On Site 
0 Days
Bedrooms 
2
Inside Area (SqFt) 
2,555 sqft
Total Baths 
3
Full Baths 
2
Partial Baths 
1
Lot Size 
13.84 Acres
Year Built 
1988
MLS® Number 
A4680403
Status 
Active
Property Tax 
$8,564.88
HOA/Condo/Coop Fees 
$6,271
Sq Ft Source 
Public Records
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What's This?
Private
Recent Activity
10 hours agoListing updated with changes from the MLS®
10 hours agoListing first seen on site
General Features
Acres 
13.84
Attached Garage 
Yes
Direction Faces 
Southwest
Foundation 
BlockSlab
Garage 
Yes
Garage Spaces 
2
Levels 
One
Number Of Stories 
1
Parking 
Garage Door OpenerAttached
Pets 
Dogs OKSize LimitYes
Property Sub Type 
Townhouse
Security 
Gated CommunitySecurity GateSecurity SystemSecurity System LeasedSmoke Detector(s)
Sewer 
Public Sewer
SqFt Total 
3270
Utilities 
Cable AvailableElectricity ConnectedSewer ConnectedUnderground UtilitiesWater Connected
Water Source 
Public
Zoning 
MUC1
Interior Features
Appliances 
DishwasherDisposalDryerElectric Water HeaterMicrowaveRangeRefrigeratorWasher
Cooling 
Central AirHumidity Control
Fireplace 
Yes
Fireplace Features 
Living Room
Flooring 
CarpetTileVinylWood
Furnished 
Furnished
Heating 
CentralElectric
Interior 
Eat-in KitchenOpen FloorplanTray Ceiling(s)
Laundry Features 
InsideLaundry Room
Window Features 
Window CoveringsBlindsWindow Treatments
Bathroom 1 
Dimensions - 12x10Level - First
Bathroom 2 
Dimensions - 5x5Level - First
Bedroom 2 
Dimensions - 13x13Level - First
Den 
Dimensions - 12x14Level - First
Dining Room 
Dimensions - 11x19Level - First
Kitchen 
Dimensions - 11x15Level - FirstFeatures - Breakfast Bar
Laundry 
Dimensions - 5x10Level - First
Living Room 
Dimensions - 16x19Level - FirstFeatures - Ceiling Fan(s)
Master Bedroom 
Dimensions - 18x14Level - First
Office 
Dimensions - 18x7Level - First
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Exterior Features
Construction Details 
HardiPlank Type
Exterior 
Awning(s)CourtyardGardenLightingPrivate EntrancePrivate Yard
Fencing 
Masonry
Patio And Porch 
PatioRear PorchScreened
Roof 
Tile
View 
PondWaterGolf Course
Waterfront Features 
Beach Access
Waterview 
PondWaterGolf Course
Windows/Doors 
Window CoveringsBlindsWindow Treatments
Community Features
Association Amenities 
Pool
Association Dues 
922
Community Features 
GatedPool
Financing Terms Available 
CashConventional
HOA Fee Frequency 
Annually
MLS Area 
34228 - Longboat Key
Roads 
Asphalt
Township 
36S
Schools
School District
Unknown
Elementary School
Southside Elementary
Middle School
Booker Middle
High School
Booker High
Listing courtesy of MICHAEL SAUNDERS & COMPANY (941) 312-1146



Listing information is provided by Participants of the Stellar MLS. IDX information is provided exclusively for 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 is deemed reliable but not guaranteed. Properties displayed may be listed or sold by various participants in the MLS Copyright 2026, Stellar MLS.
Last checked: 2026-02-27 02:35 AM EST

Neighborhood & Commute
Source: Walkscore
Disclosure: Community information and market data powered by Constellation Data Labs. Information is deemed reliable but not guaranteed.
Powered by Showcase IDX, a Constellation1 Company
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The Wendy Lynn Group Sarasota exp Realty

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The Wendy Lynn Group Sarasota exp Realty

  • 1300 Main Street, Sarasota, FL 34236
  • 941-421-7375
  • info@sunnysarasotahomes.com

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