1358 South Main Street, Cheshire, Connecticut

$760,000

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4

Beds

4/2

Baths

3,610

Square feet

0.60

Acres

About 1358 South Main Street

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!

Features of 1358 South Main Street

MLS® # 24159711
Price $760,000
Bedrooms 4
Bathrooms 4/2
Full Baths 4
Half Baths 2
Square Footage 3,610
Acres 0.60
Type Single Family For Sale
Style Cape Cod, Colonial
Status Closed

Community Information

Address 1358 South Main Street
Area N/A
City Cheshire
County New Haven
State Connecticut
Zip Code 06410

Amenities

Parking Attached Garage, Detached Garage
Garage Spaces 4
Is Waterfront No
Waterfront Not Applicable
Has Pool Yes
Pool Vinyl, Indoor Pool

Interior

Interior Features Sauna
Appliances Gas Range, Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer
Heating Gas on Gas, Zoned
Cooling Central Air, Wall Unit, Zoned
Fireplace Yes
# of Fireplaces 1

Exterior

Exterior Clapboard, Vinyl Siding
Lot Description Treed, Level Lot
Roof Asphalt Shingle
Foundation Concrete, Stone

School Information

Elementary Per Board of Ed
High Per Board of Ed

Additional Information

Date Listed March 31st, 2026
Days on Market 3
Zoning R-20
RE / Bank Owned No

Listing Details

Listing Map

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