Under contract-accepting backup offers. Welcome to 2053 Woody Drive, where timeless Windermere charm meets modern updates. From the moment you arrive, you’ll appreciate the mature trees, spacious homesite, and the peaceful lifestyle this sought-after community offers. Through Windermere Downs HOA you will have access to a private beach -Chain of Lakes-
Step inside and you’ll find a beautifully updated kitchen that’s truly the heart of the home—perfect for everyday living and entertaining family and friends.
The generous living spaces, oversized lot and mature landscaping, with a prime location make this home an incredible opportunity for anyone looking to enjoy everything- Windermere.
ROOF: 2020 NEW ELECTRIC PANEL (2026)-AC 2019
Step inside and you’ll find a beautifully updated kitchen that’s truly the heart of the home—perfect for everyday living and entertaining family and friends.
The generous living spaces, oversized lot and mature landscaping, with a prime location make this home an incredible opportunity for anyone looking to enjoy everything- Windermere.
ROOF: 2020 NEW ELECTRIC PANEL (2026)-AC 2019
Property Details
Price:
$679,000
MLS #:
O6421738
Status:
Active Under Contract
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINDERMERE DOWNS
Neighborhood:
34786windermere
Listed Date:
Aug 11, 2026
Finished Sq Ft:
2,177
Total Sq Ft:
2,778
Lot Size:
16,352 sqft / 0.38 acres (approx)
Year Built:
1973
See this Listing
Schools
Elementary School:
Thornebrooke Elem
Middle School:
Gotha Middle
High School:
Olympia High
Interior
Appliances
Dishwasher, Microwave, Refrigerator
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Tile
Heating
Central, Electric
Interior Features
Primary Bedroom Main Floor, Thermostat
Laundry Features
Inside
Levels
One
Exterior
Architectural Style
Ranch
Association Amenities
Park, Tennis Court(s), Vehicle Restrictions
Attached Garage YN
1
Community Features
Dock, Lake, Special Community Restrictions
Construction Materials
Wood Frame
Covered Spaces
2
Direction Faces
West
Exterior Features
Lighting
Fencing
Fenced, Wood
Garage Spaces
2
Open Parking YN
1
Parking Features
Driveway, Garage Faces Side
Patio And Porch Features
Porch
Roof
Shingle
View
Garden
Waterfront Features
Lake
Financial
HOA Fee
$1,058
HOA Fee Frequency
Annually
HOA Includes
Manager
HOA Name
Windermere Downs Assn Mgmt/Trident Assn
HOA Phone
4072976396
Tax Year
2025
Taxes
$4,023
Map
Community
- Address2053 WOODY DRIVE WINDERMERE FL
- SubdivisionWINDERMERE DOWNS
- CityWINDERMERE
- CountyOrange
- Zip Code34786
Market Summary
Current real estate data for Single Family in WINDERMERE as of Aug 29, 2026
247
Single Family Listed
117
Avg DOM
460
Avg $ / SqFt
$2,331,259
Avg List Price
Property Summary
- Located in the WINDERMERE DOWNS subdivision, 2053 WOODY DRIVE WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $679,000 and features 3 beds, 3 baths, and has approximately 2,177 square feet of living space, and was originally constructed in 1973. The current price per square foot is $312. The average price per square foot for Single Family listings in WINDERMERE is $460. The average listing price for Single Family in WINDERMERE is $2,331,259. To schedule a showing of MLS#o6421738 at 2053 WOODY DRIVE in WINDERMERE, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of LPT REALTY, LLC. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 2053 WOODY DRIVE
WINDERMERE, FL