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1421 CHESTNUT Avenue
WINTER PARK FL 32789 US

$750,000

Active Listing ID O6442587
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3 bed
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1,325 square feet
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1.00 Bath (1 Full)
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Lot: 0.17 Acres
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Single Family Residence

$750,000

Active Listing ID O6442587
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1421 CHESTNUT Avenue Prime Winter Park builder and luxury custom home opportunity with rare dual access! Nestled in this Winter Park enclave just one block from the Via Streets, this location offers a massive competitive advantage and features a dedicated rear easement providing direct vehicle or construction access to the adjacent side street (Sunset). Whether you are an investor looking for a high-end project or designing your private sanctuary, this unique dual-access point is a designer's dream-opening up incredible architectural flexibility, private rear-loading/garage options, or seamless construction staging. The property boasts an unobstructed view of the serene park setting at the intersection of Chestnut and Sunset, providing a picturesque backdrop for custom luxury home architecture. Surrounding properties are rapidly redeveloping into spectacular modern estates. Bring your custom builder and your vision to claim one of Winter Park's unique footprints. Property is being sold As-Is with value in the land. One car garage at rear of property with access thru deeded easement. Shed next to garage.

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Property Features

  • Facts
  • Lot Size: 0.17 Acres
  • Property Type: Residential
  • Property Sub-type: Single Family Residence
  • Features
  • Full Bathrooms: 1
  • Cooling System: Central Air
  • Exterior Finish: Sidewalk
  • Floor Covering: Wood
  • Roof Type: Shingle
  • Heating Fuels: Electric (Heating)
  • Additional Features
  • Fireplace

Property

  • propertytype: Residential
  • propertysubtype: Single Family Residence
  • listprice: 750000
  • unparsedaddress: 1421 CHESTNUT Avenue
  • postalcity: WINTER PARK
  • stateorprovince: FL
  • country: US
  • postalcode: 32789
  • bathroomsfull: 1
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.17
  • lotsizeunits: Acres
  • lotsizearea: 0.17
  • livingarea: 1325
  • livingareaunits: Square Feet
  • latitude: 28.61386
  • longitude: -81.334242
  • listagentfullname: Barry Sanford PA
  • listagentemail: barrypsanford@aol.com
  • listagentkey: 3yd-MFRMLSFL-261009260
  • listagentmlsid: 261009260
  • listagentpreferredphone: 4076945598
  • listagentofficephone: 4076945598
  • listofficekey: 3yd-MFRMLSFL-50096
  • listofficemlsid: 50096
  • 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: 1952
  • listingcontractdate: 2026-09-18
  • listagentfax: 4076442032
  • listagenturl: http://crrmove.com
  • countyorparish: Orange
  • parcelnumber: 32-21-30-4536-01-250
  • appliances: Range
  • cooling: Central Air
  • constructionmaterials: Brick
  • flooring: Wood
  • heating: Electric (Heating)
  • fireplaceyn: True
  • transactiontype: ForSale
  • storiestotal: 1
  • parkingtotal: 0
  • roof: Shingle
  • waterfrontyn: False
  • franchiseaffiliation: None
  • interiorfeatures: Ceiling Fans(s)
  • exteriorfeatures: Sidewalk
  • architecturalstyle: Other
  • rooms: Bedroom 1, Bedroom 3, Bathroom 1, Bedroom 2
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: True
  • internetconsumercommentyn: True
  • location: -81.33424, 28.61386
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"Charles Rutenberg Realty Orlando LLC", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "CustomSourceId":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"barrypsanford@aol.com", "ListBrokerageCity":"Winter Park", "ListBrokerageCountry":"US", "ListBrokerageEmail":"monica@crrmove.com", "ListBrokerageLogoUrl":"http://lh.rdcpix.com/5c855fd03c1311e8b5180242ac110005k-c2775226819r.png", "ListBrokerageName":"Charles Rutenberg Realty Orlando LLC", "ListBrokeragePhone":"(407) 622-2122", "ListBrokeragePostalCode":"32789", "ListBrokerageStateOrProvince":"FL", "ListBrokerageUnitNumber":"Suite 200", "ListBrokerageUnparsedAddress":"631 S Orlando Avenue", "ListBrokerageWebsiteUrl":"http://crrmove.com", "ListOfficeAddress1":"631 S Orlando Avenue Suite 200 Suite 200", "ListOfficeAddress2":"Suite 200", "ListOfficeBrokerMlsId":"50096", "ListOfficeCity":"Winter Park", "ListOfficeCountry":"US", "ListOfficeEmail":"monica@crrmove.com", "ListOfficePostalCode":"32789", "ListOfficeStateOrProvince":"FL", "ListPriceCurrencyType":"USD", "ListingTitle":"Residential, WINTER PARK, FL", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/1421-Chestnut-Ave_Winter-Park_FL_32789_M67206-84374?f=listhub&s=MFRMLSFL&m=O6442587&c=rexren", "MLSModificationTimestamp":"2026-09-19 10:51:26", "Neighborhoods":[{"Description":null, "Name":"LAKE KNOWLES TERRACE"}], "PostalCode":null, "RoomCount":3, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":1882, "TaxDescription":"LAKE KNOWLES TERRACE K/4 LOT 25 BLK 1", "TaxYear":"2025"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 9/19/2026 10:53:53 AM GMT
Source Updated Date: 9/21/2026 12:38:05 PM GMT

Courtesy of: Barry Sanford PA, CHARLES RUTENBERG REALTY ORLANDO, barrypsanford@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.