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:
Jul 6, 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
Subdivisions in WINDERMERE
- ACREAGE
- ALADAR ON LAKE BUTLER
- ASHLIN FARK PH 2
- ASHLIN PARK PH 1
- ASHLIN PARK PH 2
- ASHLIN PK PH 2
- BELLARIA
- BELMERE VILLAGE G-5
- BELMERE VILLAGE G2 48 65
- BUTLER BAY
- CARRINGTON
- CASA DEL LAGO REP
- CASABELLA
- CASABELLA PH 2
- CHAINE DE LAC
- CHAINE DU LAC
- CREEKS RUN
- DAVIS SHORES
- DIAMONDHEAD
- DOWN POINT SUB
- EDEN’S HAMMOCK
- EDENS HAMMOCK
- ENCLAVE
- ENCLAVE AT BERKSHIRE PARK
- ESTANCIA/WINDERMERE
- ESTATES AT WINDERMERE
- FARMS
- GARDENS OF ISLEWORTH
- GLENMUIR
- GLENMUIR 48 39
- GLENMUIR UNIT 1
- GLENMUIR UT 02 51 42
- GOTHA TOWN
- HARBOR ISLE
- ISLEWORTH
- ISLEWORTH WEST
- KEENE’S POINTE
- KEENES POINTE
- KEENES POINTE 46/104
- KEENES POINTE UNIT 01
- KEENES POINTE UNIT 1
- KEENES POINTE UNIT 7
- KEENES POINTE UNIT 9
- KEENES POINTE UT 04 SEC 31 48 82
- KEENES POINTE UT 06 50 95
- KELSO ON LAKE BUTLER
- LAKE BURDEN SOUTH PH 2
- LAKE BURDEN SOUTH PH 2 #35 36
- LAKE BURDEN SOUTH PH I
- LAKE BUTLER ESTATES
- LAKE BUTLER PARK PT REP
- LAKE BUYNAK ESTATES
- LAKE CAWOOD ESTATES
- LAKE CRESCENT RESERVE
- LAKE DAVIS RESERVE A & B
- LAKE DOWN ESTATES
- LAKE DOWN POINTE 50 42
- LAKE DOWN RESERVE
- LAKE DOWN SHORES REP
- LAKE ROPER POINTE
- LAKE SAWYER SOUTH PH 01
- LAKE SAWYER SOUTH PH 02
- LAKE SAWYER SOUTH PH 03
- LAKE SAWYER SOUTH PH 05
- LAKE SAWYER SOUTH PH 1
- LAKE SAWYER SOUTH PH 3
- LAKES
- LAKES OF WINDERMERE
- LAKES OF WINDERMERE PH 2A
- LAKES WINDERMERE PH 01 49 108
- LAKES/WINDERMERE
- LAKES/WINDERMERE LAKE REAMS
- LAKES/WINDERMERE LAKE REAMS TWNH
- LAKES/WINDERMERE PH 02A
- LAKES/WINDERMERE PH 03 P & Q
- LAKES/WINDERMERE PH 04
- LAKES/WINDERMERE-LK REAMS TWHM
- LAKES/WINDERMERE-LK REAMS TWNH
- LAKES/WINDERMERE-PEACHTREE
- LAKESIDE VILLAS
- LAKESIDE/LKS/WINDERMERE
- LAKESIDE/LKS/WINDERMERE A CONDO
- LAKESIDE/LKS/WINDERMERE PH 3
- LANDINGS AT LAKE SAWYER
- LEGADO
- MARINA BAY ESTATES
- MERRICK LANDING
- MERRICK LNDG
- METCALF PARK REP
- OASIS COVE 2 AT LAKESIDE VILAGE
- OASIS COVE AT LAKE SIDE
- OASIS COVE I/LAKESIDE VILLAGE PH 01
- OASIS COVE II/LAKESIDE VILLAGE PH
- PALMS AT WINDERMERE
- PEACHTREE PARK
- PRESTON SQUARE
- PROVIDENCE
- PROVIDENCE PH 01 50 03
- PROVIDENCE PH 02
- RESERVE AT BELMERE
- RESERVE AT BELMERE PH 02 48 144
- RESERVE AT BELMERE PHASE IV
- RESERVE AT LAKE BUTLER SOUND
- RESERVE AT LAKE BUTLER SOUND UNIT 2
- RESERVE AT WINDERMERE
- ROBERTS LANDING
- ROSSER RESERVE REP
- ROYAL ESTATE
- ROYAL ESTATES
- SADDLECREST AT WINDERMERE
- SANCTUARY/LKS/WINDERMERE
- SAWYER SHORES SUB
- SAWYER SOUND
- SILVER WOODS
- SILVER WOODS PH 03
- SILVER WOODS PH 04
- STILLWATER XINGS PRCL SC-13 #2
- SUMMERPORT
- SUMMERPORT BEACH
- SUMMERPORT PH 03
- SUMMERPORT PH 05
- SUMMERPORT PH 1
- SUMMERPORT PHASE 4
- SUNSET BAY
- THE LAKES
- TILDENS GROVE
- TILDENS GROVE PH 01 47/65
- TUSCANY RIDGE 50 141
- VINEYARDS/HORIZONS WEST PH 1A
- VINEYARDS/HORIZONS WEST PH 1B
- VINEYARDS/HORIZONS WEST PH 2A
- VINEYARDS/HORIZONS WEST PH 2B
- VINEYARDS/HORIZONS WEST PH 4
- WATERFORD POINTE
- WATERSTONE
- WAUSEON RIDGE
- WEATHERSTONE ON LAKE OLIVIA
- WESTOVER CLUB PH 01 44/139
- WESTOVER RESERVE PH 02
- WESTSIDE VILLAGE
- WHITNEY ISLES/BELMERE PH 02
- WICKHAM PARK
- WICKHAM PARK 04 05 06 09 10 11 12 01
- WILLOWS AT LAKE RHEA PH 02
- WINDEMERE SOUND PH 2
- WINDEMERE TRLS PH 3B
- WINDERMERE
- WINDERMERE ISLE
- WINDERMERE ISLE PH 2
- WINDERMERE ISLE-PH 2
- WINDERMERE LANDINGS
- WINDERMERE LANDINGS PH 2
- WINDERMERE LNDGS FD-1
- WINDERMERE LNDGS PH 02
- WINDERMERE OAKS
- WINDERMERE POINTE
- WINDERMERE REP
- WINDERMERE SOUND
- WINDERMERE SOUND PH 2
- WINDERMERE TERRACE
- WINDERMERE TOWN
- WINDERMERE TOWN REP
- WINDERMERE TRAILS PHASE 5A 80/102 LOT 39
- WINDERMERE TRLS PH 1A
- WINDERMERE TRLS PH 1B
- WINDERMERE TRLS PH 1C
- WINDERMERE TRLS PH 3A
- WINDERMERE TRLS PH 3B
- WINDERMERE TRLS PH 4B
- WINDERMERE TRLS PH 5A
- WINDERMERE TRLS PRCL 3
- WINDSOR HILL
- WINDSTONE
Market Summary
Current real estate data for Single Family in WINDERMERE as of Jul 23, 2026
269
Single Family Listed
109
Avg DOM
466
Avg $ / SqFt
$2,460,680
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 $466. The average listing price for Single Family in WINDERMERE is $2,460,680. To schedule a showing of MLS#o6421738 at 2053 WOODY DRIVE in WINDERMERE, FL, contact your CENTURY 21 Carioti agent at 2392986550.
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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 CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti 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