LONGBOAT KEY, FL 34228 3466 WINDING OAKS DRIVE 35

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Presented By: COLDWELL BANKER REALTY with 941-383-6411. - 941-383-6411
  • MLS# A4686581
  • 04/07/2026
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Disclaimer: The information contained in this listing has not been verified by Homepride Group at EXP Realty and should be verified by the buyer.
  • Beds • 2
  • Baths • 2
  • SQFT • 2,039
  • Garage • 2

Home Details

Located in one of the most sought-after villa communities on Longboat Key, this well-kept 2-bedroom, 2-bath home in Winding Oaks lives more like a single-family residence—without all the upkeep. Behind the gates of Bay Isles, it offers a great opportunity to enjoy a quiet, established neighborhood known for its natural beauty and relaxed feel. A paver driveway and walkway, surrounded by mature landscaping, lead you to the front door. Inside, high ceilings and warm wood floors immediately make the space feel open and inviting. The finishes are neutral and timeless, and the natural light really does the rest. Impact glass throughout adds both comfort and peace of mind. The main living area flows easily, with a striking corner of sliding glass doors that brings the outdoors in and opens to a spacious, screened, deck. It’s the kind of space you’ll actually use—whether that’s for entertaining, relaxing, or just enjoying the greenery around you. The kitchen is nicely laid out with stone countertops, stainless appliances, a tray ceiling, and a large window that keeps things bright. Both bedrooms are generously sized. The primary suite feels like a true retreat, with vaulted ceilings, a walk-in closet, and sliding doors that open to the deck with peaceful nature views. The bathroom is spacious, featuring dual vanities, a Jacuzzi tub, walk-in shower, and well-done tile details. Additional highlights include a two-car garage and a floor plan that offers a nice balance of openness and privacy. Winding Oaks is part of the Bay Isles Harbourside golf course community and offers a gated entrance, community pool, and access to Bay Isles amenities—including deeded beach access through the private Bay Isles Beach Club. It’s an easy, comfortable lifestyle in one of Longboat Key’s most desirable communities.
Presented By: COLDWELL BANKER REALTY with 941-383-6411. - 941-383-6411

Interior Features for 3466 WINDING OAKS DRIVE 35

Bedrooms

Total Bedrooms2

Bathrooms

Half Baths0
Total Baths2

Other Interior Features

LivingAreaSourcePublic Records
Air Conditioning Y/NYes
Fireplace Y/NNo
FlooringTile, Hardwood
Furnished Y/NNegotiable
Heating Y/NYes
Interior AmenitiesBuilt-in Features, Ceiling Fan(s), Eating Space In Kitchen, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Stone Counters, Thermostat, Window Treatments
Laundry FeaturesLaundry Room
Total Stories1

General for 3466 WINDING OAKS DRIVE 35

Additional Parcels Y/NNo
AppliancesBuilt-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
Architectural StyleOther
Association AmenitiesPool
Association Fee IncludesCommunity Pool, Escrow Reserves Fund, Insurance, Maintenance Structure, Maintenance Grounds, Pest Control, Pool Maintenance, Private Road, Sewer, Trash, Water
Association NameAdvanced Management / AMIA
AssociationName2Bay Isles Homeowners Association
Attached Garage Yes
Building Area UnitsSquare Feet
Carport Y/NNo
CityLONGBOAT KEY
Community FeaturesDeed Restrictions, Pool
Construction MaterialsBlock, Stucco
CoolingCentral Air
CountySarasota
DirectionsFrom St. Armands Circle - North to Gulf of Mexico Dr, turn right at south gate for Bay Isles (Harbourside Dr), turn right to 2020 Harbourside Dr.
DockY/NNo
Facing DirectionEast
Flood Zone CodeAE*
Full Baths2
Garage Spaces2
Garage Y/NYes
HOA Fee 2791.03
HOA Fee 2 FrequencyAnnually
HOA Monthly Maintenance
HeatingCentral, Electric
Home Warranty Y/NNo
Land Lease Y/NNo
Lease Considered Y/NYes
Legal DescriptionUNIT 35 WINDING OAKS
LevelsOne
Listing TermsCash, Conventional
Living Area UnitsSquare Feet
Lot Size Square Feet602945
Lot Size UnitsAcres
MLS Area34228 - Longboat Key
Minimum Lease3 Months
Monthly Condo Fee Amount2228
New ConstructionNo
Occupancy TypeOwner
OwnershipFee Simple
Patio/Porch FeaturesCovered, Deck, Rear Porch
Pet Size LimitLarge (61-100 Lbs.)
Pets AllowedYes
Pool FeaturesHeated, In Ground
Property ConditionCompleted
Property SubtypeCondominium
Property TypeResidential
RoofOther
STELLAR_InLawSuiteYNNo
Senior Community Y/NNo
SewerPublic Sewer
Standard StatusActive
StatusActive
Subdivision NameWINDING OAKS
Tax Annual Amount4918.69
Tax Lot0
Tax Year2025
Total Rooms7
Unit Number35
UtilitiesElectricity Connected, Public, Sewer Connected, Underground Utilities, Water Connected
ViewWater
Virtual TourClick here
Water Access Y/NNo
Water View Y/NNo
Year Built1988
ZoningMUC1

Exterior for 3466 WINDING OAKS DRIVE 35

Building Area Total2568
Covered Spaces2
Exterior AmenitiesIrrigation System, Lighting, Sidewalk, Sliding Doors, Storage
Foundation DetailsSlab
Lot Size Acres13.84
Lot Size Area13.8417
Parking FeaturesDriveway, Garage Door Opener
Private PoolNo
Road ResponsibilityPrivate Maintained Road
Road Surface TypePaved
VegetationMature Landscaping
Water SourcePublic
Waterfront Y/NNo

Additional Details

Price History

Schools

High School Hubert H Humphrey Middle School
Middle School N/A
Elementary School Big Hollow Elementary School

Steven Pugh

Broker Associate | Team Leader
Price $795,000
MLS#A4686581
List Date 04/07/2026
Property Type Condos
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