58 MAIN STREET, Windermere, FL 34786

• 5 beds |
• 4 baths |
• 4,875 sqft

Property Description

Nestled in the heart of Old Town Windermere, this exceptional lakefront residence offers direct access to the Butler Chain of Lakes from the tranquil waters of Wauseon Bay, prized for its reduced boat traffic and peaceful setting. Set on an oversized waterfront lot with western exposure, the home captures breathtaking lake views from nearly every room—delivering spectacular sunsets and a seamless indoor-outdoor lifestyle. Over 4800sq 5 bedrooms, 4 full bathrooms, Recently enhanced by renovations completed in 2020, the residence now features a newly added owner’s retreat with spa-inspired bathroom, thoughtfully designed to maximize comfort, privacy, and sweeping lake views. Additional updated interior in 2022 showcases refined craftsmanship and high-end finishes, including Provenza engineered hardwood flooring, vaulted tongue-and-groove ceilings, cedar beams, updated bathrooms, custom drapery, and plantation shutters. The large open kitchen is designed for both everyday living and entertaining, featuring 42-inch cabinetry, two oversized kitchen islands, a GE Profile refrigerator, and an Advantium double oven, all seamlessly connected to the main living areas. The great room opens effortlessly to the outdoor living spaces through fully retractable sliding doors, creating an ideal setting for gatherings of any size. Outdoor amenities rival those of a private resort, featuring a saltwater pool with pebble-tech finish and shallow lounging shelf, summer kitchen with natural gas Artisan grill, motorized patio screens, indoor/outdoor surround sound, and a luxury boat dock with electric cradle and Trex decking—perfect for enjoying the Butler Chain lifestyle year-round. Additional highlights include interior and exterior security systems, natural gas, city water, roof 2020, and a newer septic tank. Located just steps from downtown Windermere, residents enjoy a charming small-town atmosphere with farmers markets, cafés, local shops, and dining, while remaining only minutes from Restaurant Row and Orlando’s premier amenities. A rare opportunity to own a fully updated lakefront retreat in one of Central Florida’s most coveted communities.

Listing Status:

Active

Date Added:

February 5, 2026

Data Last Updated:

February 9, 2026 at 12:21PM

Listing Office:

LPT REALTY, LLC : 877-366-2213

Listing Agent:

Michelle Ingrassia : 407-756-9164

MLS ID:

O6370886

Interior

• General: Ceiling Fans(s)High CeilingsKitchen/Family Room ComboLiving Room/Dining Room ComboOpen FloorplanPrimary Bedroom Main FloorSolid Wood CabinetsSplit BedroomStone CountersThermostatVaulted Ceiling(s)Walk-In Closet(s)Window Treatments
• Rooms: Inside Utility
• Appliances: Built-In OvenConvection OvenDishwasherDisposalGas Water HeaterMicrowaveRefrigerator
• Laundry: InsideLaundry Room
• Flooring: HardwoodTileWood
• A/C: Central Air
• Heating: Electric
• Fireplace: GasFireplace

Exterior

• General: LightingOutdoor GrillRain GuttersSliding Doors
• Style: Traditional
• Other Structures: Rear Porch
• Pool: GuniteIn GroundSalt Water
• Parking: DrivewayGarage Door OpenerGolf Cart Garage

Construction

• Roofing: Shingle
• Windows: BlindsDouble Pane WindowsShuttersWindow Treatments
• General: BlockStuccoTwoSlab

Location

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

Lot

• Zoning: SFRREPLAT PART OF LAKE BUTLER PARK R/39 LOTS 8 & 908-23-28-4348-00-080
• View: Water
• Fencing: Fenced

Utilities

• Utilities: BB/HS Internet AvailableCable AvailableElectricity ConnectedNatural Gas ConnectedPublicSewer ConnectedWater Connected
• Water: Public
• Sewer: Septic Tank

Financial

• Source: Stellar MLS
• Ownership: Fee Simple