58 MAIN STREET WINDERMERE FL 34786 MLS #O6370886 | Gary Kusher | Florida Real Estate

58 MAIN STREET
WINDERMERE, FL, 34786
$3,725,000
5 Beds
4 Baths
4,875 SqFt
0.58 Acres
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MLS #O6370886 image #0
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
TraditionalWaterfrontLakefrontPoolPrimary Bedroom Main Floor34786 – Windermere34786windermereLake Butler Park Pt RepLake Butler Wauseon BayWater1-2 Years

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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
Laundry Features
Inside, Laundry Room

Exterior

Architectural Style
Traditional
Construction Materials
Block, Stucco
Exterior Features
Irrigation System, Lighting, Outdoor Grill, Rain Gutters, Sliding Doors
Parking Features
Driveway, Garage Door Opener, Golf Cart Garage
Roof
Shingle

Financial

Tax Year
2024
Taxes
$21,723

Map

Community

Subdivisions in WINDERMERE

Market Summary

Current real estate data for Single Family in WINDERMERE as of Mar 18, 2026
257
Single Family Listed
101
Avg DOM
462
Avg $ / SqFt
$2,229,890
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 $462. The average listing price for Single Family in WINDERMERE is $2,229,890. To schedule a showing of MLS#o6370886 at 58 MAIN STREET in WINDERMERE, FL, contact your CENTURY 21 Carioti agent at 2392986550.

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58 MAIN STREET
WINDERMERE, FL