1002 OAKDALE STREET, Windermere, FL 34786

• 4 beds |
• 3 baths |
• 3,516 sqft

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.

Listing Status:

Active

Date Added:

April 14, 2026

Data Last Updated:

June 26, 2026 at 4:23AM

Listing Office:

KELLER WILLIAMS SUBURBAN TAMPA : 813-684-9500

Listing Agent:

Frank Smith : 401-644-4762

MLS ID:

TB8495717

Interior

• General: ThermostatWalk-In Closet(s)
• Rooms: Den/Library/OfficeFamily Room
• Appliances: DishwasherMicrowaveRangeRefrigerator
• Laundry: Inside
• Basement: Finished
• Flooring: CarpetHardwoodTile
• A/C: Central Air
• Heating: Electric
• Fireplace: Family RoomFireplace

Exterior

• General: Balcony
• Other Structures: Front PorchDeckCovered

Construction

• Roofing: Shingle
• General: StuccoOneSlab

Location

• Road/Access: Dirt
• Originating MLS: Stellar MLS
• County: Orange

Lot

• Zoning: SFRPLAT OF WINDERMERE G/36 LOT 5517-23-28-9336-00-550

Utilities

• Utilities: Public
• Water: Public
• Sewer: Septic Tank

Financial

• Source: Stellar MLS
• Ownership: Fee Simple