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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.

Agent 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 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

4 full
1953

Amenities

PoolFireplaceWaterfrontHardwood

Monthly Cost Estimate

$19,922/mo

20% down · 6.5% · 30 years

Principal$2,694
Interest$16,142
Insurance$1,086

Estimates only. Actual payments may vary.

Location

58 MAIN STREET

Windermere, FL 34786

LAKE BUTLER PARK PT REP

Features & Amenities

Interior Features

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

Exterior Features

FencingLightingOutdoor GrillRain GuttersSliding DoorsPoolDock

Property Details

Flooring

HardwoodTileWood

Construction

BlockStucco

Parking

DrivewayGarageGarage - AttachedGolf Cart

Heating

Electric (Heating)Fireplace(s)

Cooling

Central Air

Appliances

DishwasherGarbage DisposerMicrowaveOven - ConvectionRefrigeratorWasher

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.

MI

Michelle Ingrassia

Agent at LPT REALTY, LLC

(407) 756-9164

Listed by LPT REALTY, LLC · View on Broker Site

MLS# O6370886· Source: listhub· Updated 116 days ago

Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

58 MAIN STREET, Windermere, FL 34786

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