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.
Property Details
Price:
$3,725,000
MLS #:
O6370886
Status:
Active
Beds:
5
Baths:
4
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
LAKE BUTLER PARK PT REP
Neighborhood:
34786windermere
Listed Date:
Feb 5, 2026
Finished Sq Ft:
4,875
Total Sq Ft:
6,355
Lot Size:
25,329 sqft / 0.58 acres (approx)
Year Built:
1953
See this Listing
Schools
Interior
Appliances
Built-In Oven, Convection Oven, Dishwasher, Disposal, Gas Water Heater, Microwave, Refrigerator
Bathrooms
4 Full Bathrooms
Cooling
Central Air
Flooring
Engineered Hardwood, Tile, Hardwood
Heating
Electric
Interior Features
Ceiling Fan(s), High Ceilings, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Vaulted Ceiling(s), Walk-In Closet(s), Window Treatments
Laundry Features
Inside, Laundry Room
Levels
Two
Exterior
Architectural Style
Traditional
Attached Garage YN
1
Construction Materials
Block, Stucco
Covered Spaces
3
Direction Faces
Northeast
Exterior Features
Irrigation System, Lighting, Outdoor Grill, Rain Gutters, Sliding Doors
Fencing
Fenced
Garage Spaces
3
Lot Features
City Lot, Oversized Lot
Open Parking YN
1
Parking Features
Driveway, Garage Door Opener, Golf Cart Garage
Patio And Porch Features
Rear Porch
Roof
Shingle
View
Water
Waterfront Features
Lake Front, Lake – Chain of Lakes
Window Features
Blinds, Double Pane Windows, Shutters, Window Treatments
Financial
Tax Year
2024
Taxes
$21,723
Map
Community
- Address58 MAIN STREET WINDERMERE FL
- SubdivisionLAKE BUTLER PARK PT REP
- CityWINDERMERE
- CountyOrange
- Zip Code34786
Market Summary
Current real estate data for Single Family in WINDERMERE as of May 23, 2026
268
Single Family Listed
98
Avg DOM
488
Avg $ / SqFt
$2,527,990
Avg List Price
Property Summary
- Located in the LAKE BUTLER PARK PT REP subdivision, 58 MAIN STREET WINDERMERE FL is a Single Family for sale in WINDERMERE, FL, 34786. It is listed for $3,725,000 and features 5 beds, 4 baths, and has approximately 4,875 square feet of living space, and was originally constructed in 1953. The current price per square foot is $764. The average price per square foot for Single Family listings in WINDERMERE is $488. The average listing price for Single Family in WINDERMERE is $2,527,990. To schedule a showing of MLS#o6370886 at 58 MAIN STREET in WINDERMERE, FL, contact your LPT Realty agent at 813.694.8061.
Similar Listings Nearby
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 LPT Realty include the name of the listing broker. Neither the listing company nor LPT Realty 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. 58 MAIN STREET
WINDERMERE, FL
