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299 W 4TH AVENUE
WINDERMERE FL 34786 US

$895,000

Pending Listing ID O6357207
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4 bed
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3.00 Bath (3 Full)
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Lot: 0.38 Acres
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Single Family Residence

$895,000

Pending Listing ID O6357207
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299 W 4TH AVENUE This traditional farmhouse blends Old Florida charm with everyday comfort — a rare opportunity in the heart of Windermere. Full of character inside and out, the home sits on an elevated corner lot, offering room to play and beautiful curb appeal. A welcoming front porch invites you to slow down, relax, and enjoy the neighborhood setting. Step inside to original wood floors that extend throughout the main living areas, enriching the home with warmth and timeless appeal. The family room centers around a charming wood-burning fireplace, surrounded by newly installed windows (2020) that fill the space with natural light. French doors open to a large screened porch — an ideal spot for morning coffee, outdoor dining, or unwinding beneath the shade of mature trees. The island kitchen features granite countertops and generous workspace for cooking and entertaining. The first floor includes a full bedroom and bath, perfect for guests or a home office. Upstairs, the spacious primary suite offers a peaceful retreat, joined by two additional bedrooms and the convenience of a second-floor laundry room. New Septic and drain field 2020, A/C 2024, Well re-sleaved and new pump 2024. A partially air-conditioned, three-car garage provides excellent storage and space for vehicles, golf carts, or weekend adventure gear. Stroll or golf-cart your way to cafes, shops or the local brewery. Spend weekends at town parks, tennis and pickleball courts, or out on the world-famous Butler Chain of Lakes. With no HOA dues, tree-lined streets, and the peace of mind of a dedicated police department, Windermere combines natural beauty, community charm, and everyday convenience.

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Property Features

  • Facts
  • Lot Size: 0.38 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 3
  • Cooling System: Central Air
  • Exterior Finish: Corner Lot, Unpaved, French Doors, Private Mailbox
  • Floor Covering: Laminate, Wood
  • Roof Type: Shingle
  • Heating Fuels: Central, Electric (Heating), Fireplace(s)
  • Additional Features
  • Fireplace

School Information

  • School
  • Windermere Elem(Elementary)
  • Gotha Middle(MiddleSchool)
  • Olympia High(HighSchool)

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 895000
  • unparsedaddress: 299 W 4TH AVENUE
  • postalcity: WINDERMERE
  • stateorprovince: FL
  • country: US
  • postalcode: 34786
  • bathroomsfull: 3
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.38
  • lotsizeunits: Acres
  • lotsizearea: 0.38
  • livingarea: 2410
  • livingareaunits: Square Feet
  • latitude: 28.496439
  • longitude: -81.537672
  • listagentfullname: Judy Black
  • listagentemail: judyblackfla@gmail.com
  • listagentkey: 3yd-MFRMLSFL-261001354
  • listagentmlsid: 261001354
  • listagentpreferredphone: 4078101803
  • listagentofficephone: 4073085750
  • listofficekey: 3yd-MFRMLSFL-261016477
  • listagentstatelicense: 329124
  • listofficemlsid: 261016477
  • disclaimer: Copyright © 2025 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: 1984
  • listingcontractdate: 2025-11-05
  • listagenturl: https://www.upsiderealestategroup.com/
  • countyorparish: Orange
  • parcelnumber: 17-23-28-9336-03-200
  • elementaryschool: Windermere Elem
  • highschool: Olympia High
  • appliances: Cooktop, Dishwasher, Dryer, Garbage Disposer, Microwave, Washer
  • cooling: Central Air
  • constructionmaterials: Wood Siding
  • flooring: Laminate, Wood
  • heating: Central, Electric (Heating), Fireplace(s)
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • parkingfeatures: Driveway, Garage, Garage - Attached, Golf Cart
  • roof: Shingle
  • waterfrontyn: False
  • interiorfeatures: Ceiling Fans(s), Solid Wood Cabinets, Stone Counters, Vaulted Ceiling(s), Walk-in Closet(s)
  • exteriorfeatures: Corner Lot, Unpaved, French Doors, Private Mailbox
  • architecturalstyle: Craftsman
  • rooms: Bathroom 1, Bathroom 2, Bathroom 3, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Kitchen, Living Room
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -81.537674, 28.496439
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Upside Real Estate", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"judyblackfla@gmail.com", "ListBrokerageCity":"Orlando", "ListBrokerageCountry":"US", "ListBrokerageEmail":"jasoncblack1@gmail.com", "ListBrokerageLogoUrl":"http://brokerlogos.listhub.net/MFRMLSFL/9581b7714f1311e9aa480242ac110004/20190325155015571.png", "ListBrokerageName":"Upside Real Estate", "ListBrokeragePhone":"(407) 497-6345", "ListBrokeragePostalCode":"32803", "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":null, "ListBrokerageUnparsedAddress":"2810 Middlesex Rd.", "ListBrokerageWebsiteUrl":"https://www.upsiderealestategroup.com/", "ListOfficeAddress1":"2810 Middlesex", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":null, "ListOfficeCity":"Orlando", "ListOfficeCountry":"US", "ListOfficeEmail":"jasoncblack1@gmail.com", "ListOfficePostalCode":"32803", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"Single Family Residence, Craftsman - WINDERMERE, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/299-W-4th-Ave_Windermere_FL_34786_M56337-52968?f=listhub&s=MFRMLSFL&m=O6357207&c=rexren", "MLSModificationTimestamp":"2025-12-13T06:18:08Z", "Neighborhoods":[], "PostalCode":null, "RawPropertySubType":"Single Family Residence", "RawPropertyType":"Residential", "RoomCount":7, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":10545, "TaxDescription":null, "TaxYear":"2024"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 12/13/2025 1:05:37 PM GMT
Source Updated Date: 12/17/2025 6:45:25 PM GMT

Courtesy of: Judy Black, UPSIDE REAL ESTATE INC, judyblackfla@gmail.com

Copyright © 2025 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.