3436 Winding Oaks Dr #44, Longboat Key


2 Beds
2 Baths
2,112 Sqft
13.82 Acres
2 Garages

With the comfort and convenience of maintenance-free living and the feel of a single-family home, this attached villa in the Winding Oaks section of Bay Isles offers the best of all worlds in an esteemed, tropical mid-key location. Perfectly positioned on a serene lakefront lot, this spacious split plan boasts two bedrooms plus a den and an abundance of privacy for family and guests. A paver drive and walkway take you to the architecturally attractive front entryway, where beyond the threshold unfolds the living area and an expansive setting with vaulted ceilings, tile floors, a cozy wood-burning fireplace, and natural light through sliders on the corners of 2 walls, which lead to the tranquil ambiance on the extended screened deck and spa overlooking the lake. Bathed in the natural light of 5 over-counter windows, the kitchen is both bright and beautiful, with a breakfast bar opening to the family room, white cabinetry, solid surface counters and stainless-steel appliances. Through the privacy of double doors one finds the master suite, which has vaulted ceilings, walk-in closets, 2 sets of sliders to the screened deck, and master bath with shower, garden tub and glass block detail. Additional details include a voluminous 2-car garage, newer water heater and inside laundry room. Delight in a world of resort-style amenities nearby and as a resident of Bay Isles, miles of walking & bike paths, pool, and membership in the Bay Isles Beach Club providing deeded beach and gulf access are included in home ownership.

Essential Information
MLS® #A4474851
Full Baths2
Square Footage2,112
Year Built1988
StyleCape Cod, Custom
Price Per Sqft$269
Community Information
Address3436 Winding Oaks Dr #44
AreaLongboat Key
SubdivisionWinding Oaks
CityLongboat Key
CountySarasota County
Zip Code34228
Max Pet Weight101
Pet Restrictions YNY
Pets Allowed YNY
Pet SizeExtra Large (101+ Lbs.)
Numof Pets1
Minimum Lease3 Months
Community Features

Private Boat Ramp, Security, Buyer Approval Required, Deed Restrictions, Pool, Water Access

# of Garages2
Water ViewLake

Cable Connected, Electricity Connected, Phone Available, Sewer Connected, Underground Utilities, Water Connected


Private Boat Ramp, Security, Buyer Approval Required, Deed Restrictions, Pool, Water Access


Driveway, Garage Door Opener, Ground Level


Under Building Parking, , 2 Car Garage


Flood Insurance Required, FloodZone, Greenbelt View, Water View

Water Access

Beach - Access Deeded, Gulf/Ocean

InteriorCarpet, Ceramic Tile
HeatingCentral, Electric
CoolingCentral Air
# of Stories1
Master Bed Size15x16
Interior Features

Cathedral Ceiling(s), Ceiling Fans(s), Master Bedroom Downstairs, Walk-In Closet(s), Window Treatments


Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer


One, End Unit, Ground Floor Unit

Interior Layout

Bonus Room, Great Room, Inside Utility, Master Bedroom Downstairs, Walk-In Closet(s)

ExteriorBlock, Wood Frame, Wood Siding
WindowsWindow Treatments
Exterior Features

Awning(s), Irrigation System, Sliding Doors, Mature Landscaping, Trees/Landscaped, Patio/Porch Screened

Room Dimensions
Bedroom 213x14
Dining Room12x18
Family Room12x12
Living Room20x16
Master Bedroom15x16
School Information
ElementarySouthside Elementary
MiddleBooker Middle
HighBooker High
Additional Information
Days on Market7
Normal SaleYes
Condo Fees$3,760
Condo Fees TermQuarterly
HOA Fee$568
HOA Payment ScheduleAnnual
Homestead YNYes
Tax Year2019

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Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on September 24th, 2020 at 2:15am EDT.