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1358 S Main Street

Cheshire, CT 06410
  • $749,000
  • STATUS: Active Under Contract
  • ON SITE: 44 Days
  • MLS #: 24159711
Under Contract
UPDATED: 69 min ago
$749,000
  • 4
    BEDS
  • 0.6
    ACRES
  • 4
    BATHS
  • 2
    1/2 BATHS
  • 3,610
    SQFT
  • $207
    $/SQFT
Type:
Single-Family Home
Built:
1900
County:
Area:

School Information

Elementary School:
High School:

Description

Don't miss this rare opportunity to own a truly one-of-a-kind property offering exceptional space, flexibility, and amenities. This 3,600+ SF home features 4 bedrooms, 4.5 baths, including a versatile in-law apartment, home gym, plus two garages with plenty of room for multiple cars. The original 1900 colonial main house blends classic charm with modern updates, offering three bedrooms, 1.5 baths, an updated eat-in kitchen, fireplace with pellet stove, and flexible living space. The attached in-law apartment has vaulted ceilings, a full bath, kitchen, office or workshop, and spacious living room. The spiral staircase leads to a private second-floor bedroom loft with another full bath and laundry area. With a separate entrance, this space is ideal for multi-generational living, guests, or a home office/business. A standout feature of the property is the detached building, currently a fully equipped home fitness center with endless pool, sauna, and full bath. Car enthusiasts will appreciate the additional 32-foot-deep two-car garage with tandem parking for up to four cars and ample storage. Conveniently located in prime southern Cheshire near shopping, dining, and everyday amenities. Schedule your showing today to see this amazing property! The in-law addition was completed in 1986 and the fitness/pool building and additional garage were added in 2012. Sellers updated the oil heat to natural gas furnace in 2023. The hot tub was removed and sauna installed in 2024. Each section (main house, in-law unit and gym) offers its own heating and cooling system with on-demand hot water for maximum comfort and efficiency.

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The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc. Data last updated: 2026-05-15T21:10:16.937.
www.lowerhudsonvalleyproperties.com/homes/174602029
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1358 S Main Street Cheshire, CT 06410

  • Price: $749,000
  • Status: Active Under Contract
  • On Site: 44 Days
  • Updated: 69 min ago
  • MLS #: 24159711
4
Beds
4
Baths
2
½ Baths
0.6
Acres
3,610
SQFT
$207
$/SQFT
1900
Built
County:
New Haven
Area:
Cheshire
Elementary School:
per board of ed
High School:
per board of ed
Property Description
Don't miss this rare opportunity to own a truly one-of-a-kind property offering exceptional space, flexibility, and amenities. This 3,600+ SF home features 4 bedrooms, 4.5 baths, including a versatile in-law apartment, home gym, plus two garages with plenty of room for multiple cars. The original 1900 colonial main house blends classic charm with modern updates, offering three bedrooms, 1.5 baths, an updated eat-in kitchen, fireplace with pellet stove, and flexible living space. The attached in-law apartment has vaulted ceilings, a full bath, kitchen, office or workshop, and spacious living room. The spiral staircase leads to a private second-floor bedroom loft with another full bath and laundry area. With a separate entrance, this space is ideal for multi-generational living, guests, or a home office/business. A standout feature of the property is the detached building, currently a fully equipped home fitness center with endless pool, sauna, and full bath. Car enthusiasts will appreciate the additional 32-foot-deep two-car garage with tandem parking for up to four cars and ample storage. Conveniently located in prime southern Cheshire near shopping, dining, and everyday amenities. Schedule your showing today to see this amazing property! The in-law addition was completed in 1986 and the fitness/pool building and additional garage were added in 2012. Sellers updated the oil heat to natural gas furnace in 2023. The hot tub was removed and sauna installed in 2024. Each section (main house, in-law unit and gym) offers its own heating and cooling system with on-demand hot water for maximum comfort and efficiency.
Exterior Features

Color Green Direct Waterfront YN No Exterior Siding ClapboardVinyl Siding Garage And Parking Attached GarageDetached Garage Lot Description TreedLevel Lot Nearby Amenities Basketball CourtMedical FacilitiesParkPublic Rec Facilities Pool Description VinylIndoor Pool Roof Information Asphalt Shingle Style Cape CodColonial Swimming Pool YN Yes Waterfront Description Not Applicable

Interior Features

Appliances Included Gas RangeOven/RangeMicrowaveRefrigeratorDishwasherWasherDryer Attic Description Access Via Hatch Attic YN Yes Basement Description PartialStoragePartially FinishedConcrete Floor Cooling System Central AirWall UnitZoned Fireplaces Total 1 Heat Type Gas on GasZoned In Law Access First FloorSeparate Entry In Law Apartment Yes Interior Features Sauna Laundry Room Info Lower LevelUpper Level Laundry Room Location Main house-basement & apartment-loft Living Area SQFTPer Public Record 0 Rooms Bedroom (Upper Level Ceiling FanHardwood Floor) Bedroom (Upper Level Ceiling FanHardwood Floor) Bedroom (Other Level Ceiling FanFull BathLaundry Hookup) Primary Bedroom (Upper Level Ceiling FanHardwood Floor) Living Room (Main Level) Eat-In Kitchen (Main Level) Family Room (Main Level) Rec/Play Room (Other Level Full BathSteam/Sauna) Kitchen (Other Level Remodeled) Living Room (Other Level) Rooms Additional Exercise RoomGym Sq Ft Est Heated Above Grade 3338 Sq Ft Est Heated Below Grade 272 Total Rooms 10

Property Features

Acceptable Financing FHAVACHFA Agent Owner YN No Bank Owned Property No Financing Used Conventional Fixed Foundation Type ConcreteStone Home Owners Assocation No Home Warranty Offered YN No Hot Water Description Natural GasTankless Hotwater New Construction Type No/Resale Potential Short Sale No Sewage System Public Sewer Connected Tax Year July 2025-June 2026 Under Agreement Yn No Water Source Public Water Connected Zoning R-20

Listing information © 2026 Smart MLS
Listing provided courtesy of Heidi Hoss of Coldwell Banker Realty: (860) 434-8600.


The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc. Data last updated: 2026-05-15T21:10:16.937.
 
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