3444 Winding Oaks Dr #42, Longboat Key


3 Beds
2 Baths
2,189 Sqft
0 Acres
2 Garages

Words can’t describe this stunning, completely remodeled 3brm (or 2brm/den) 2 Bath, 2 car garage home in Winding Oaks, a maintenance-free community of 56 Nantucket-style villas located behind the gates of the renowned Longboat Key Club in beautiful Bay Isles. A private courtyard and walkway lead to the entrance, where you’ll experience WOW factor the moment you walk in: spacious, light and airy living room with a stunning floor-to-ceiling silver tiled fireplace wall and expansive, sliding glass doors that lead to the deck, vaulted ceilings, open floor plan, high-end finishes, LED recessed lighting throughout, and remote controlled fans make this home perfect for relaxed living and entertaining. The large, sleek kitchen offers gorgeous cabinets and counters, stainless appliances and is open to the living and dining areas. You enter the spacious master wing through beautiful, double glass doors that lead to the large bedroom suite with vaulted ceilings, an abundance of custom closets and a wall of sliders to the deck. The beautifully appointed, soothing spa-like master bath with over sized shower and storage completes your oasis. Relax in peaceful privacy on your newly rebuilt, over sized composite deck with retractable awnings while enjoying soothing water and fountain views and where tropical bird life abounds. A gorgeous, canopied community pool and deck are just a few steps away. Residents also have access to the Bay Isles' private, deeded beach/club pavilion.

Essential Information
MLS® #A4474298
Full Baths2
Square Footage2,189
Year Built1988
Price Per Sqft$345
Community Information
Address3444 Winding Oaks Dr #42
AreaLongboat Key
SubdivisionWinding Oaks
CityLongboat Key
CountySarasota County
Zip Code34228
Max Pet Weight99
Pet RestrictionsSee condominium restrictions
Pet Restrictions YNY
Pets Allowed YNY
Pet SizeLarge (61-100 Lbs.)
Numof Pets1
Minimum Lease3 Months
Community Features

Gated, Maintenance, Deed Restrictions, Gated Community, Pool

# of Garages2
Is WaterfrontYes
WaterfrontLagoon, Lake
Water AccessBeach - Private, Lagoon, Lake
Water ViewLagoon, Lake

Cable Available, Electricity Connected, Public


Gated, Maintenance, Deed Restrictions, Gated Community, Pool


Garage Door Opener, Parking Pad


Under Building Parking, , 2 Car Garage


Corner Lot, Sidewalk, Street Private, Garden View, Pool View, Water View

InteriorCarpet, Ceramic Tile
CoolingCentral Air
FireplacesLiving Room, Wood Burning
Kitchen FeaturesBreakfast Bar, Closet Pantry
Master Bed Size15x16
Interior Features

Cathedral Ceiling(s), Ceiling Fans(s), Living Room/Dining Room Combo, Split Bedroom, Vaulted Ceiling(s), Walk-In Closet(s)


Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer


One, End Unit, Ground Floor Unit

Interior Layout

Attic, Family Room, Inside Utility, Living Room/Dining Room Combo, Split Bedroom, Walk-In Closet(s)

Master Bath Features

Dual Sinks, Tub with Separate Shower Stall

ExteriorWood Frame
Lot DescriptionNon-Applicable
Exterior Features

Balcony/Sun Deck, Hurricane Shutters, Irrigation System, Rain Gutters, Sliding Doors, Sprinkler Metered, Mature Landscaping, Patio/Porch Covered

Room Dimensions
Bedroom 213x14
Dining Room12x18
Family Room12x15
Living Room20x15
Master Bedroom15x16
School Information
ElementarySouthside Elementary
MiddleBooker Middle
HighBooker High
Additional Information
Days on Market5
Normal SaleYes
Condo Fees$3,760
Condo Fees TermQuarterly
HOA Fee$735
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 3:30am EDT.