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58 MAIN STREET
WINDERMERE FL 34786 US

$3,725,000

Active Listing ID O6370886
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5 bed
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4.00 Bath (4 Full)
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Lot: 0.58 Acres
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Single Family Residence

$3,725,000

Active Listing ID O6370886
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58 MAIN STREET 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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Property Features

  • Facts
  • Lot Size: 0.58 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 4
  • Cooling System: Central Air
  • Exterior Finish: Fencing, Lighting, Outdoor Grill, Rain Gutters, Sliding Doors, Pool, Dock
  • Floor Covering: Hardwood, Tile, Wood
  • Roof Type: Shingle
  • Heating Fuels: Electric (Heating), Fireplace(s)
  • Additional Features
  • Fireplace
  • Pool
  • Waterfront

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 3725000
  • unparsedaddress: 58 MAIN STREET
  • postalcity: WINDERMERE
  • stateorprovince: FL
  • country: US
  • postalcode: 34786
  • bathroomsfull: 4
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.58
  • lotsizeunits: Acres
  • lotsizearea: 0.58
  • livingarea: 4875
  • livingareaunits: Square Feet
  • latitude: 28.501332
  • longitude: -81.537695
  • listagentfullname: Michelle Ingrassia
  • listagentemail: michelleirealtor@aol.com
  • listagentkey: 3yd-MFRMLSFL-261203585
  • listagentmlsid: 261203585
  • listagentpreferredphone: 4077569164
  • listagentofficephone: 8773662213
  • listofficekey: 3yd-MFRMLSFL-261016803
  • listagentstatelicense: 3231559
  • listofficemlsid: 261016803
  • disclaimer: 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.
  • sourcesystemid: MFRMLSFL
  • yearbuilt: 1953
  • listingcontractdate: 2026-02-05
  • listagenturl: https://www.lpt.com/
  • countyorparish: Orange
  • parcelnumber: 08-23-28-4348-00-080
  • appliances: Dishwasher, Garbage Disposer, Microwave, Oven - Convection, Refrigerator, Washer
  • cooling: Central Air
  • constructionmaterials: Block, Stucco
  • flooring: Hardwood, Tile, Wood
  • heating: Electric (Heating), Fireplace(s)
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • parkingfeatures: Driveway, Garage, Garage - Attached, Golf Cart
  • roof: Shingle
  • waterfrontyn: True
  • interiorfeatures: Ceiling Fans(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
  • exteriorfeatures: Fencing, Lighting, Outdoor Grill, Rain Gutters, Sliding Doors, Pool, Dock
  • waterfrontfeatures: Lake Front, Lake Privileges, Waterfront
  • architecturalstyle: New Traditional
  • rooms: Bathroom 1, Bathroom 2, Bathroom 3, Bathroom 4, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Den, Family Room, Kitchen, Living Room
  • structuretype: Dock
  • dock: True
  • poolprivateyn: True
  • spayn: False
  • fencing: Fenced
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -81.5377, 28.501331
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"LPT Realty, LLC.", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"michelleirealtor@aol.com", "ListBrokerageCity":"Lake Mary", "ListBrokerageCountry":"US", "ListBrokerageEmail":"boards@lpt.com", "ListBrokerageLogoUrl":null, "ListBrokerageName":"LPT Realty, LLC.", "ListBrokeragePhone":"(877) 366-2213", "ListBrokeragePostalCode":"32746", "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"1400 S. International Parkway", "ListBrokerageWebsiteUrl":"https://www.lpt.com/", "ListOfficeAddress1":"1400 South International Parkw", "ListOfficeAddress2":"Suite 1020", "ListOfficeBrokerMlsId":null, "ListOfficeCity":"Lake Mary", "ListOfficeCountry":"US", "ListOfficeEmail":"flbrokers@lptrealty.com", "ListOfficePostalCode":"32746", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"Single Family Residence, Traditional - WINDERMERE, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/58-Main-St_Windermere_FL_34786_M57284-75506?f=listhub&s=MFRMLSFL&m=O6370886&c=rexren", "MLSModificationTimestamp":"2026-02-05T20:09:09Z", "Neighborhoods":[], "PostalCode":null, "RawPropertySubType":"Single Family Residence", "RawPropertyType":"Residential", "RoomCount":10, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":21723.13, "TaxDescription":null, "TaxYear":"2024"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 2/6/2026 3:06:01 AM GMT
Source Updated Date: 2/14/2026 6:53:47 PM GMT

Courtesy of: Michelle Ingrassia, LPT REALTY, LLC, michelleirealtor@aol.com

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.