1358 South Main Street
Cheshire, CT, 06410 $ 749,000
Bedrooms4 Baths4.2 Sq 3,610 Monthly Estimate*
$ 4,612
for $749,000 with 4 bedrooms and 4 full baths, 2 half baths. This 3,610 square foot home was built in 1900 on a lot size of 0.6.
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.
See more
FeaturesGeneralZoning R-20
Neighborhood N/A
County New Haven
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Under Contract - Continue to Show
Acres 0.6
Directions GPS friendly. On Main St turn right into driveway after light at Cook Hill Rd. Look for sign.
High School Per Board of Ed
City Cheshire
Elementary School Per Board of Ed
Sq Ft Total 3610
DOM 4
Year Built 1900
Style Cape Cod Colonial
Year Built Source Public Records
Pool Description Vinyl Indoor Pool
See more
InteriorCooling System Central Air Wall Unit Zoned
Total Rooms 10
Basement Description Partial Storage Partially Finished Concrete Floor
See more
ExteriorWater Source Public Water Connected
Lot Description Treed Level Lot
See more
* Excluded FeaturesList ByColdwell Banker RealtyBroker
heidi.hoss@cbrealty.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $4,612
- Monthly Property Taxes
- $913
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Cheshire, CT
Average List Price $785,583
Percent of Sale Price 5%
About Cheshire, CT 29,795 Population
4% Since 2002
$ 107,809 Median Income
44.2 Median Age
30% Households with Children
Trends Information provided by ATTOM Data Solutions.
3092524 Elementary School
1232933 Middle School
Per Board of Ed High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 3/31/2026 | $749,000 | | Listed Price |