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37-39 Main Street
Chester NY 10918 US

$1,498,888

Active Listing ID 873541
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4 bed
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4.00 Bath (4 Full)
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Lot: 0.06 Acres
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Triplex

$1,498,888

Active Listing ID 873541
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37-39 Main Street Prime Investment Opportunity in the Heart of Chester Village – 37-39 Main Street & 9 Bank Street Nestled in the charming and historic Village of Chester, this fully updated mixed-use property presents an exceptional investment opportunity. Originally built in 1935, this rustic yet modernized building seamlessly blends timeless character with contemporary upgrades. The property features: • Fully Leased Commercial Space: Home to the popular Rustic Wheelhouse Restaurant, a well-established local favorite offering consistent foot traffic and long-term stability. • Three Leased Apartments: Spacious and updated residential units providing reliable rental income. • Bonus Rear Lot at 9 Bank Street: Included with the purchase, this additional parcel offers endless potential—ideal for building a garage, apartment, patio, or deck to further enhance the value and utility of the property. • Ample Municipal Parking: Convenient and plentiful public parking surrounds the property, ensuring ease of access for tenants, patrons, and guests. This historic gem is located on Main Street, within walking distance to shops, parks, and community amenities. Whether you’re seeking a turn-key investment or a hybrid commercial-residential property in a thriving village setting, 37-39 Main Street & 9 Bank Street deliver charm, income, and growth potential. Don’t miss your chance to own a piece of Chester’s history—fully updated and income-producing from day one.

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Property Features

  • Facts
  • Lot Size: 0.06 Acres
  • Property Type: Residential Multi Family
  • Property Sub-type: Triplex
  • Features
  • Full Bathrooms: 4
  • Cooling System: Ductless
  • Floor Covering: Vinyl, Wood
  • Heating Fuels: Natural Gas

School Information

  • School
  • Chester Elementary School(Elementary)
  • Chester Academy-Middle/High School(MiddleSchool)
  • Chester Academy-Middle/High School(HighSchool)

Property

  • propertytype: Residential Multi Family
  • propertysubtype: Triplex
  • listprice: 1498888
  • unparsedaddress: 37-39 Main Street
  • postalcity: Chester
  • stateorprovince: NY
  • country: US
  • postalcode: 10918
  • bathroomsfull: 4
  • bathroomshalf: 0
  • bathroomsonequarter: 0
  • bathroomsthreequarter: 0
  • lotsizeacres: 0.055
  • lotsizeunits: Acres
  • lotsizearea: 0.055
  • livingarea: 7308
  • livingareaunits: Square Feet
  • listagentfullname: James Feldhaus
  • listagentemail: jamesfeldhausrealty@gmail.com
  • listagentkey: 3yd-MLSLINY-59107
  • listagentmlsid: 59107
  • listagentpreferredphone: 8452488008
  • listagentofficephone: 8882760630
  • listofficekey: 3yd-MLSLINY-EXPRLT
  • listagentstatelicense: 10401348240
  • listofficemlsid: EXPRLT
  • disclaimer: Copyright © 2025 OneKey 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: MLSLINY
  • yearbuilt: 1935
  • listingcontractdate: 2025-06-05
  • countyorparish: Orange County
  • parcelnumber: 332201-102-000-0001-026.000-0000
  • elementaryschool: Chester Elementary School
  • highschool: Chester Academy-Middle/High School
  • elementaryschooldistrict: Chester
  • middleorjuniorschooldistrict: Chester
  • highschooldistrict: Chester
  • cooling: Ductless
  • constructionmaterials: Frame
  • flooring: Vinyl, Wood
  • heating: Natural Gas
  • numberofunitstotal: 4
  • fireplaceyn: False
  • transactiontype: ForSale
  • storiestotal: 0
  • parkingtotal: 0
  • parkingfeatures: On Street
  • waterfrontyn: False
  • interiorfeatures: Beamed Ceilings, Chefs Kitchen, High Ceilings, Primary Bathroom, Open Floorplan, Washer/Dryer Hookup
  • architecturalstyle: Other
  • rooms: Basement, Bathroom 1, Bathroom 2, Bathroom 3, Bathroom 4, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4
  • dock: False
  • poolprivateyn: False
  • spayn: False
  • internetaddressdisplayyn: True
  • internetautomatedvaluationdisplayyn: False
  • internetconsumercommentyn: False
  • customfields: {"AdditionalInformation":{}, "AlternatePrices":[], "BrokerName":"eXp Realty", "BuilderEmail":null, "BuilderFax":null, "BuilderPhone":null, "City":null, "Country":null, "Expenses":[], "GeocodeOptions":null, "LeadRoutingEmail":"jamesfeldhausrealty@gmail.com", "ListBrokerageCity":"Hauppauge", "ListBrokerageCountry":"US", "ListBrokerageEmail":"kim.canavan@exprealty.net", "ListBrokerageLogoUrl":"http://brokerlogos.listhub.net/104/470253/20240314175529848.png", "ListBrokerageName":"eXp Realty", "ListBrokeragePhone":"(888) 276-0630", "ListBrokeragePostalCode":"11788", "ListBrokerageStateOrProvince":"NY", "ListBrokerageUnitNumber":"Suite 145", "ListBrokerageUnparsedAddress":"400 Townline Rd.", "ListBrokerageWebsiteUrl":null, "ListOfficeAddress1":"777 Westchester Ave, Ste 101", "ListOfficeAddress2":null, "ListOfficeBrokerMlsId":"48675", "ListOfficeCity":"White Plains", "ListOfficeCountry":"US", "ListOfficeEmail":"ny.broker@exprealty.net", "ListOfficePostalCode":"10604", "ListOfficeStateOrProvince":"NY", "ListPriceCurrencyType":"USD", "ListingTitle":"Barndominium, Triplex - Chester, NY", "ListingURL":"https://www.realtor.com/realestateandhomes-detail/37-Main-St_Chester_NY_10918_M38546-71317?f=listhub&s=MLSLINY&m=873541&c=rexren", "MLSModificationTimestamp":"2025-10-22T11:25:45Z", "Neighborhoods":[], "PostalCode":null, "RawPropertySubType":"Triplex", "RawPropertyType":"Residential Income", "RoomCount":null, "StateOrProvince":null, "Taxes":[{"TaxAnnualAmount":12067.42, "TaxDescription":null, "TaxYear":"2024"}], "UnitNumber":null, "UnparsedAddress":null}
Listing Changed: 10/22/2025 5:08:35 PM GMT
Source Updated Date: 12/13/2025 6:47:22 PM GMT

Courtesy of: James Feldhaus, eXp Realty, jamesfeldhausrealty@gmail.com

Copyright © 2025 OneKey MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.