Property
ActiveResidential
1/60
$965,000

1002 OAKDALE STREET

Windermere, FL 34786
4
Beds
3
Baths
3,516
SqFt
0.29
Acres
STELLAR
#TB8495717
Updated: Jun 23, 2026, 1:08pm

Property Description

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.
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Included Appliances
DishwasherMicrowaveRangeRefrigerator

Property Details

Interior
Additional Rooms
Den/Library/OfficeFamily Room
Appliances
DishwasherMicrowaveRangeRefrigerator
Basement
Finished
Bathrooms Total Decimal
3
Building Area Total
5720
Cooling
Central Air
Fireplace Features
Family Room
Flooring
CarpetEngineered HardwoodTile
Furnished
Unfurnished
Heating
Electric
Interior Features
ThermostatWalk-In Closet(s)
Laundry Features
Inside
Living Area
3516
Rooms Total
12
Construction
Building Area Source
Public Records
Building Area Units
Square Feet
Construction Materials
Stucco
Direction Faces
Southwest
Foundation Details
Slab
Levels
One
Living Area Source
Public Records
Living Area Units
Square Feet
Roof
Shingle
Year Built
1973
Site & Exterior
Covered Spaces
4
Exterior Features
Balcony
Flood Zone Code
X
Garage Spaces
4
I D X Participation
Yes
Lot Features
Corner Lot
Lot Size Acres
0.29
Lot Size Area
12801
Lot Size Square Feet
12801
Lot Size Units
Square Feet
Patio And Porch Features
CoveredDeckFront Porch
Public Survey Range
28
Public Survey Section
17
Road Surface Type
Dirt
Sewer
Septic Tank
Total Acreage
1/4 to less than 1/2
Utilities
Public
Water Source
Public
Zoning
SFR
Financials
Calculated List Price By Calculated Sq Ft
274.46
Contract Status Change Date
2026-04-14
Current Price
965000
Feed Types
BBO
Lease Considered
Yes
Minimum Lease
No Minimum
Owner Name
HAPRO HOLDINGS LLC
Ownership
Fee Simple
Parcel Number
172328933600550
Public Survey Township
23
Tax Annual Amount
8799
Tax Block
36
Tax Book Number
G-36
Tax Legal Description
PLAT OF WINDERMERE G/36 LOT 55
Tax Lot
55
Tax Year
2025

Neighborhood & Lifestyle

Community & Association
Additional Lease Restrictions
Buyer/Buyer agent responsible to verify with Orange county rules and regulations.
Lease Restrictions
Yes
M L S Area Major
34786 - Windermere
Subdivision Name
WINDERMERE TOWN
Listing provided courtesy of STELLAR via IDX. Updated: Jun 23, 2026, 1:08pm.
Frank Smith

Listing Agent

KELLER WILLIAMS SUBURBAN TAMPA

Call Agent