Set on a prominent corner lot in one of Windermere’s most sought-after enclaves, this thoughtfully updated residence blends timeless character with modern upgrades, enormous walk out bottom level, massive multiple garages and a lifestyle that is uniquely local to this area. Relax on the expansive front porch and take in the surroundings as neighbors and nature pass by.
Recent improvements include a new roof, a fully renovated kitchen, a designer-inspired primary bath, fresh interior and exterior paint, and newer engineered wood flooring, creating a cohesive, move-in ready home with a refined, modern feel. The layout offers expansive living spaces filled with natural light, designed for both everyday comfort and effortless entertaining.
The primary suite serves as a true retreat, highlighted by a beautifully reimagined bath featuring a freestanding soaking tub, custom tile work, and a double vanity. Additional living areas and a spacious lower level provide flexibility for a media room, home office, fitness space, or guest accommodations.
A rare offering in this location, the property features an impressive 3 bay, 30′ long garage on one end and an additional garage bay on the opposite end of the home., ideal for collectors, storage, or workshop needs.
Positioned along historic Windermere’s signature tree-lined dirt roads, the setting offers a level of charm and privacy that is increasingly hard to find. Residents enjoy exclusive access to city tennis courts and a private dock with entry to the interconnected lake chain that surrounds this community, delivering a true lake lifestyle just moments from home.
Seller is open to negotiating a closing cost credit, providing added flexibility and value for buyers for closing costs or rate buy down.
A compelling combination of location, scale, and thoughtful updates—this is Windermere living at its best.
Recent improvements include a new roof, a fully renovated kitchen, a designer-inspired primary bath, fresh interior and exterior paint, and newer engineered wood flooring, creating a cohesive, move-in ready home with a refined, modern feel. The layout offers expansive living spaces filled with natural light, designed for both everyday comfort and effortless entertaining.
The primary suite serves as a true retreat, highlighted by a beautifully reimagined bath featuring a freestanding soaking tub, custom tile work, and a double vanity. Additional living areas and a spacious lower level provide flexibility for a media room, home office, fitness space, or guest accommodations.
A rare offering in this location, the property features an impressive 3 bay, 30′ long garage on one end and an additional garage bay on the opposite end of the home., ideal for collectors, storage, or workshop needs.
Positioned along historic Windermere’s signature tree-lined dirt roads, the setting offers a level of charm and privacy that is increasingly hard to find. Residents enjoy exclusive access to city tennis courts and a private dock with entry to the interconnected lake chain that surrounds this community, delivering a true lake lifestyle just moments from home.
Seller is open to negotiating a closing cost credit, providing added flexibility and value for buyers for closing costs or rate buy down.
A compelling combination of location, scale, and thoughtful updates—this is Windermere living at its best.
Property Details
Price:
$965,000
MLS #:
TB8495717
Status:
Active
Beds:
4
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
WINDERMERE TOWN
Neighborhood:
34786windermere
Listed Date:
Apr 14, 2026
Finished Sq Ft:
3,516
Total Sq Ft:
5,720
Lot Size:
12,801 sqft / 0.29 acres (approx)
Year Built:
1973
See this Listing
Schools
Interior
Appliances
Dishwasher, Microwave, Range, Refrigerator
Bathrooms
3 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Engineered Hardwood, Tile
Heating
Electric
Interior Features
Thermostat, Walk-In Closet(s)
Laundry Features
Inside
Levels
One
Exterior
Attached Garage YN
1
Construction Materials
Stucco
Covered Spaces
4
Direction Faces
Southwest
Exterior Features
Balcony
Garage Spaces
4
Lot Features
Corner Lot
Patio And Porch Features
Covered, Deck, Front Porch
Roof
Shingle
Financial
Tax Year
2025
Taxes
$8,799
Map
Community
- Address1002 OAKDALE STREET WINDERMERE FL
- SubdivisionWINDERMERE TOWN
- CityWINDERMERE
- CountyOrange
- Zip Code34786
Subdivisions in WINDERMERE
- ACREAGE AND UNREC
- ALADAR ON LAKE BUTLER
- ASHLIN FARK PH 2
- ASHLIN PARK PH 1
- ASHLIN PARK PH 2
- BELLA VITA ESTATES
- BELLARIA
- BELMERE VILLAGE
- BELMERE VILLAGE G-5
- BELMERE VILLAGE G2 48 65
- BELMERE VILLAGE G4 50 58
- BELMERE VILLAGE G5
- BELMERE VLG G2
- BUTLER BAY
- BUTLER RIDGE
- CARRINGTON
- CASA DEL LAGO REP
- CASABELLA
- CASABELLA PH 2
- CHAINE DE LAC
- CHAINE DU LAC
- CREEKS RUN
- DAVIS SHORES
- DOWN ACRES ESTATES
- DOWN POINT SUB
- DOWNS COVE CAMP SITES
- EDEN ISLE
- EDENS HAMMOCK
- ENCLAVE
- ENCLAVE AT WINDERMERE LANDING
- ENCLAVE/BERKSHIRE PARK B G H I
- ESTATES AT WINDERMERE
- FARMS
- GLENMUIR
- GLENMUIR 48 39
- GLENMUIR UT 02 51 42
- GOTHA TOWN
- ISLEWORTH
- ISLEWORTH 01 AMD
- KEENE’S POINTE
- KEENES POINTE
- KEENES POINTE 46/104
- KEENES POINTE UNIT 01
- KEENES POINTE UNIT 03 46/104
- KEENES POINTE UNIT 2
- KEENES POINTE UNIT 7
- KEENES POINTE UNIT 9
- KEENES POINTE UT 04 SEC 31 48 82
- KEENES POINTE UT 06 50 95
- LAKE BURDEN
- LAKE BURDEN SOUTH PH 2
- LAKE BURDEN SOUTH PH 2 #35 36
- LAKE BURDEN SOUTH PH I
- LAKE BUTLER ESTATES
- LAKE BUYNAK ESTATES
- LAKE CAWOOD ESTATES
- LAKE CAWOOD ESTS REP
- LAKE CRESENT RESERVE
- LAKE CYPRESS COVE PH 02
- LAKE DAVIS RESERVE
- LAKE DOWN COVE
- LAKE DOWN ESTATES
- LAKE HANCOCK SHORES
- LAKE ROPER POINTE
- LAKE SAWYER SOUTH
- LAKE SAWYER SOUTH PH 01
- LAKE SAWYER SOUTH PH 02
- LAKE SAWYER SOUTH PH 03
- LAKE SAWYER SOUTH PH 04
- LAKE SAWYER SOUTH PH 3
- LAKES
- LAKES OF WINDERMERE PH 1
- LAKES OF WINDERMERE PH 2A
- LAKES WINDERMERE PH 01 49 108
- LAKES/WINDERMERE PH 02A
- LAKES/WINDERMERE PH 04
- LAKES/WINDERMERE PH 3
- LAKES/WINDERMERE-LK REAMS TWHM
- LAKES/WINDERMERE-LK REAMS TWNH
- LAKES/WINDERMERE-PEACHTREE
- LAKESIDE VILLAGE TWNHMS
- LAKESIDE VILLAS
- LAKESIDE/LKS/WINDERMERE
- LAKESIDE/LKS/WINDERMERE CONDO
- LAKESIDE/LKS/WINDERMERE PH 10
- LAKESIDE/LKS/WINDERMERE PH 4
- LEGADO
- MARINA BAY ESTATES
- MARSH SUB
- MERRICK LANDING
- METCALF PARK REP
- OASIS COVE I/LAKESIDE VILLAGE PH 01
- OASIS COVE II/LAKESIDE VILLAGE
- OASIS COVE II/LAKESIDE VILLAGE PH
- OXFORD MOOR 47/30
- PALMS AT WINDERMERE
- PEACHTREE PARK
- PRESTON SQUARE
- PROVIDENCE
- PROVIDENCE PH 01 50 03
- PROVIDENCE PH 02
- PROVIDENCE PH 2
- RESERVE AT BELMERE PH 02 48 144
- RESERVE AT BELMERE PH 03 51 01
- RESERVE AT LAKE BUTLER
- RESERVE AT LAKE BUTLER SOUND
- RESERVE AT LAKE BUTLER SOUND 45/120
- RESERVE AT LAKE BUTLER SOUND UNIT 02
- RESERVE AT LAKE BUTLER SOUND UNIT 2
- RESERVE AT WINDERMERE
- RESERVE/BELMERE PH 04
- ROBERTS LANDING
- SADDLECREST AT WINDERMERE
- SANCTUARY/LKS/WINDERMERE
- SAWYER SHORES SUB
- SILVER WOODS
- SILVER WOODS PH 01
- SILVER WOODS PH 02
- SILVER WOODS PH 03A
- SILVER WOODS PH 04
- SILVER WOODS PH 3
- SOUTHBRIDGE VILLAGE
- STILLWATER XINGS PRCL SC-13 #2
- SUMMERPORT
- SUMMERPORT BEACH
- SUMMERPORT PH 02
- SUMMERPORT PH 03
- SUMMERPORT PH 04 C E F & G
- SUMMERPORT PH 05
- SUMMERPORT TRL
- SUNSET BAY
- TENNYSON PK/SUMMERPORT
- TILDENS GROVE
- TILDENS GROVE PH 01 47/65
- TUSCANY RIDGE 50 141
- VINEYARDS/HORIZON WEST PH 2A
- VINEYARDS/HORIZONS WEST PH 4
- WATERFORD POINTE
- WATERSIDE
- WATERSTONE
- WATERSTONE A D E F G H J L
- WAUSEON RIDGE
- WEATHERSTONE ON LAKE OLIVIA
- WEST LAKE BUTLER ESTATES
- WEST POINT COMMONS
- WESTOVER CLUB
- WESTOVER CLUB PH 02 47/71
- WESTOVER CLUB PH 02 REP
- WESTOVER RESERVE PH 02
- WESTSIDE VILLAGE
- WHITNEY ISLES / BELMERE PH 02
- WHITNEY ISLES AT BELMERE
- WHITNEY ISLES/BELMERE PH 02
- WICKHAM PARK
- WICKHAM PARK 04 05 06 09 10 11 12 01
- WINDDERMERE POINTE
- WINDERMERE
- WINDERMERE DOWNS
- WINDERMERE GRANDE
- WINDERMERE ISLE
- WINDERMERE ISLE PH 2
- WINDERMERE ISLE-PH 2
- WINDERMERE LNDGS PH 02
- WINDERMERE RESERVE
- WINDERMERE SOUND
- WINDERMERE SOUND PH 2
- WINDERMERE TERRACE
- WINDERMERE TOWN
- WINDERMERE TOWN REP
- WINDERMERE TRAILS
- WINDERMERE TRAILS PHASE 1C 80/15 LOT 113
- WINDERMERE TRAILS PHASE 4A
- WINDERMERE TRLS PH 1B
- WINDERMERE TRLS PH 1C
- WINDERMERE TRLS PH 3A
- WINDERMERE TRLS PH 3B
- WINDERMERE TRLS PH 4B
- WINDERMERE TRLS PH IA
- WINDERMERE TRLS PRCL 3
- WINDSOR HILL
Market Summary
Current real estate data for Single Family in WINDERMERE as of Jul 01, 2026
276
Single Family Listed
103
Avg DOM
479
Avg $ / SqFt
$2,504,079
Avg List Price
Property Summary
- Located in the WINDERMERE TOWN subdivision, 1002 OAKDALE STREET WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $965,000 and features 4 beds, 3 baths, and has approximately 3,516 square feet of living space, and was originally constructed in 1973. The current price per square foot is $274. The average price per square foot for Single Family listings in WINDERMERE is $479. The average listing price for Single Family in WINDERMERE is $2,504,079. To schedule a showing of MLS#tb8495717 at 1002 OAKDALE STREET in WINDERMERE, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
Similar Listings Nearby
Courtesy of KELLER WILLIAMS SUBURBAN TAMPA. 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. 1002 OAKDALE STREET
WINDERMERE, FL

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