58 Main Street, WINDERMERE, FL

$3,725,000

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5

Beds

4

Baths

4,875

Square feet

0.58

Acres

About 58 Main Street

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.

Features of 58 Main Street

MLS® # O6370886
Price $3,725,000
Bedrooms 5
Bathrooms 4.00
Full Baths 4
Square Footage 4,875
Acres 0.58
Year Built 1953
Type Residential
Sub-Type Single Family Residence
Style Traditional
Status Active

Community Information

Address 58 Main Street
Area Windermere
Subdivision LAKE BUTLER PARK PT REP
City WINDERMERE
County Orange
State FL
Zip Code 34786-8640

Amenities

Parking Driveway, Garage Door Opener, Golf Cart Garage
# of Garages 3
View Water
Is Waterfront Yes
Waterfront Lake Front, Lake - Chain of Lakes
Has Pool Yes

Interior

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
Appliances Built-In Oven, Convection Oven, Dishwasher, Disposal, Gas Water Heater, Microwave, Refrigerator
Heating Electric
Cooling Central Air
Fireplace Yes
Fireplaces Gas
# of Stories 2

Exterior

Exterior Features Irrigation System, Lighting, Outdoor Grill, Rain Gutters, Sliding Doors
Lot Description City Lot, Oversized Lot
Roof Shingle
Foundation Slab

Additional Information

Date Listed February 5th, 2026
Days on Market 38
Zoning SFR
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Details

OfficeLPT REALTY, LLC

Listing Map

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