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About This Home
This 5-bedroom, 4-bathroom single family at 58 MAIN STREET in Windermere, FL is listed for $3,725,000 ($764 per sqft). Built in 1953, the home offers 4,875 sqft of living space on a 0.58 acres lot.
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 cabin
etry, 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.
Key Features
- Built in 1953
- 0.58 acre lot
- Private pool
- Fireplace
- Waterfront
Property Details
Amenities
Monthly Cost Estimate
$19,922/mo
20% down · 6.5% · 30 years
Estimates only. Actual payments may vary.
Location
58 MAIN STREET
Windermere, FL 34786
LAKE BUTLER PARK PT REP
Features & Amenities
Interior Features
Exterior Features
Property Details
Flooring
Construction
Parking
Heating
Cooling
Appliances
Questions & Answers
This 5-bedroom, 4-bathroom single family at 58 MAIN STREET is listed at $3,725,000 ($764/sqft). The estimated monthly payment is $16,142 based on 20% down at 6.5% interest.
Key features include: Built in 1953, 0.58 acre lot, Private pool, Fireplace, Waterfront. Interior Features: Ceiling Fans(s), High Ceilings, Kitchen/Family Room Combo. Exterior Features: Fencing, Lighting, Outdoor Grill.
This property is listed by Michelle Ingrassia and can be reached at 4077569164 or michelleirealtor@aol.com.








