58 MAIN STREET Windermere, FL $ 3,725,000
58 MAIN STREET
$ 3,725,000
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58 MAIN STREET

Windermere, FL, 34786
$ 3,725,000
Bedrooms5 Baths4.0 Sq 4,875

Monthly Estimate*

$ 22,935

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Single Family Home for sale in Windermere, FL

for $3,725,000 with 5 bedrooms and 4 full baths. This 4,875 square foot home was built in 1953 on a lot size of 0.58.

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.

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Single Family Active

Price

$ 3,725,000

Bedrooms

5

Full Bath

4

Property Type

Single Family

Taxes

$ 21,723

Style

Traditional

Lot Size

0.58

Year Built

1953

Town/City

Windermere

County/Region

Orange

MLS | Web ID

O6370886

Features
General
Sewer Septic Tank
Heating Electric
Cooling Central Air
Utilities BB/HS Internet Available Cable Available Electricity Connected Natural Gas Connected Public Sewer Connected Water Connected
Roof Shingle
Appliances Built-In Oven Convection Oven Dishwasher Disposal Gas Water Heater Microwave Refrigerator
Zoning SFR
Garage Spaces 2
Patio/Porch Features Rear Porch
Architectural Style Traditional
Pool Features Gunite In Ground Salt Water
Construction Materials Block Stucco
Year Built 1953
View Water
Levels Two
Property Subtype Single Family Residence
Tax Year 2024
Ownership Fee Simple
Waterfront Features Lake Front Lake - Chain of Lakes
County Orange
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name LAKE BUTLER PARK PT REP
Facing Direction Northeast
Garage Y/N true
Total Rooms 10
Full Baths 4
Status Active
Directions Main street to North house on the right
City WINDERMERE
Body of Water LAKE BUTLER WAUSEON BAY
Senior Community Y/N false
MLS Area 34786 - Windermere
Lot Size Units Square Feet
Lot Size Square Feet 25329
Carport Y/N false
Listing Terms Cash Conventional
Land Lease Y/N false
Tax Annual Amount 21723.13
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.zillow.com/view-imx/4af921b5-2b32-4097-b584-0cd4bb75d286?wl=true&setAttribution=mls&initialViewType=pano https://property.listinginfo.com/106541/property/232930
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 8
Legal Description REPLAT PART OF LAKE BUTLER PARK R/39 LOTS 8 & 9
Water View Lake Lake - Chain of Lakes
Water Access Type Lake Lake - Chain of Lakes
Minimum Lease 1-2 Years
Water Access Y/N true
Additional Rooms Inside Utility
Water View Y/N true
Flood Zone Code X
DockY/N true
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Interior
Interior Amenities 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
Flooring Engineered Hardwood Tile Hardwood
Furnished Y/N Unfurnished
Fireplace Features Gas
Total Stories 2
Air Conditioning Y/N true
Heating Y/N true
Window Features Blinds Double Pane Windows Shutters Window Treatments
Fireplace Y/N true
Half Baths 0
Laundry Features Inside Laundry Room
Total Bedrooms 5
Total Baths 4
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Exterior
Exterior Amenities Irrigation System Lighting Outdoor Grill Rain Gutters Sliding Doors
Fencing Fenced
Parking Features Driveway Garage Door Opener Golf Cart Garage
Lot Features City Lot Oversized Lot
Water Source Public
Lot Size Area 25329
Foundation Details Slab
Building Area Total 6355
Lot Size Acres 0.58
Road Surface Type Dirt Gravel
Private Pool true
Waterfront Y/N true
Covered Spaces 2
Road Responsibility Public Maintained Road
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* Excluded Features
List By
Lpt Realty, Llc

Broker

michelleirealtor@aol.com

Email

Affordability Calculator

$24,746
Per Month
93%
7%
0%
Monthly Principal & Interest
$22,935
Monthly Property Taxes
$1,810
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
4827338 Elementary School
4827337 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
2/6/2026$3,725,000 Listed Price

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58 MAIN STREET, Windermere, FL, 34786 is a Single Family Home for sale at $3,725,000 with 4,875 sqft and a lot size of 0.58. 58 MAIN STREET has 5 bedrooms, 4.0 baths, and was built in 1953. The property's zip code is 34786 which is in Windermere, FL