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58 Main Street

Windermere, FL 34786
  • $3,725,000
  • STATUS: Active
  • ON SITE: 74 Days
  • MLS #: O6370886
UPDATED: 15 min ago
$3,725,000
  • 5
    BEDS
  • 0.58
    ACRES
  • 4
    BATHS
  • 0
    1/2 BATHS
  • 4,875
    SQFT
  • $764
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1953
County:
Area:

School Ratings & Info

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 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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© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-04-21T11:47:56.02.
www.realestategroupcentralflorida.com/homes/172792205
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58 Main Street Windermere, FL 34786

  • Price: $3,725,000
  • Status: Active
  • On Site: 74 Days
  • Updated: 15 min ago
  • MLS #: O6370886
5
Beds
4
Baths
0
½ Baths
0.58
Acres
4,875
SQFT
$764
$/SQFT
1953
Built
Neighborhood:
Lake Butler Park Pt Rep
County:
Orange
Area:
Windermere
Property 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 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.
Exterior Features

Additional Water Information Located on the Wauseon Bay of Lake Butler Chain of Lakes Architectural Style Traditional Attached Garage Yn Yes Carport Yn No Construction Materials BlockStucco Covered Spaces 3 Direction Faces Northeast Exterior Features Irrigation SystemLightingOutdoor GrillRain GuttersSliding Doors Fencing Fenced Foundation Details Slab Lot Features City LotOversized Lot Open Parking YN Yes Parking Features DrivewayGarage Door OpenerGolf Cart Garage Patio And Porch Features Rear Porch Pool Features GuniteIn GroundSalt Water Pool Private Yn Yes Road Surface Type DirtGravel Roof Shingle View Water Water Access LakeLake - Chain of Lakes Water Access Yn Yes Water Body Name LAKE BUTLER WAUSEON BAY Water Extras LiftLift - Covered Water Extras Yn Yes Water View LakeLake - Chain of Lakes Water View Yn Yes Waterfront Features Lake FrontLake - Chain of Lakes Waterfront Feet Total 120 Waterfront Yn Yes

Interior Features

Additional Rooms Inside Utility Appliances Built-In OvenConvection OvenDishwasherDisposalGas Water HeaterMicrowaveRefrigerator Building Area Total 6355 Cooling Central Air Cooling YN Yes Fireplace Features Gas Fireplace Yn Yes Flooring Engineered HardwoodTileHardwood Furnished Unfurnished Heating Electric Heating YN Yes Interior Features Ceiling Fan(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 Laundry Features InsideLaundry Room Levels Two Rooms Bedroom 5 (En Suite BathroomWalk-In Closet(s)) Sewer Septic Tank Stories Total 2 Water Source Public Window Features BlindsDouble Pane WindowsShuttersWindow Treatments

Property Features

Association Approval Required Yn No Association Yn No Cdd Yn No Down Payment Resource No Flood Zone Code X Garage Yn Yes Homestead Yn Yes Lease Considered YN Yes Lease Restrictions YN No Listing Terms CashConventional Minimum Lease 1-2 Years New Construction Yn No Ownership Fee Simple Property Sub Type Single Family Residence Realtor Info As-Is Senior Community Yn No Special Listing Conditions None Tax Annual Amount 21723.13 Total Annual Fees 0 Total Monthly Fees 0 Utilities BB/HS Internet AvailableCable AvailableElectricity ConnectedNatural Gas ConnectedPublicSewer ConnectedWater Connected Yrs Of Owner Prior To Leasing Re No Zoning SFR


Listing information © 2026 My Florida Regional MLS DBA Stellar MLS..
Listing provided courtesy of LPT REALTY, LLC: 877-366-2213.



© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-04-21T11:47:56.02.
 
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