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$749,000 Coming Soon

  • For Sale
  • Coming Soon
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 2 Partial Baths
  • 3,610 Sq. Ft.
  • 4 Car Garage
  • Updated 2 hours ago

Next open house:

Open House: 11:00 AM - 2:00 PM

Saturday 4/4 11:00 AM - 2:00 PM

1358 South Main Street,Cheshire, CT 06410

1358 South Main StreetCheshireCT06410

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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!

Full Property Details for 1358 S Main St

General

  • Price: $749,000
  • Taxes: (July 2025-June 2026)
  • Status: Coming Soon
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24159711
  • Updated: Today (3/31/2026)
  • Added to Site: Today
  • Expected Market Date: 4/4/2026

Interior

  • Number of Rooms: 10
  • Rooms/Areas: Exercise Room, Gym
  • Interior Features: Sauna
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Gas Range, Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 6
  • Full Bathrooms: 4
  • Half Bathrooms: 2

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom - Ceiling Fan, Hardwood Floor, Upper
  • Bedroom 1: Bedroom - Ceiling Fan, Full Bath, Laundry Hookup, Other
  • Bedroom 2: Bedroom - Ceiling Fan, Hardwood Floor, Upper
  • Bedroom 3: Bedroom - Ceiling Fan, Hardwood Floor, Upper

Other Rooms

  • Living Room: Living Room, Main
  • Family Room: Family Room, Main
  • Kitchen: Kitchen - Remodeled, Other
  • Eat In Kitchen: Eat-In Kitchen, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Full Bath, Steam/Sauna, Other
  • Rec Room: Full Bath, Steam/Sauna, Other
  • Laundry: Lower Level, Upper Level
  • In-Law/Au Pair Suite: Yes

Additional Information

  • Pool: Yes
  • Pool Description: Vinyl, Indoor Pool

Exterior

  • Color: Green

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 4
  • Parking: Attached Garage, Detached Garage

Location

  • County: New Haven
  • Driving Directions: GPS friendly. On Main St, turn right into driveway after light at Cook Hill Rd. Look for sign.

School Information

  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed

Heating & Cooling

  • Cooling Type: Central Air, Wall Unit, Zoned
  • Heating Type: Gas on Gas, Zoned
  • Water Heater: Natural Gas, Tankless Hotwater

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Cape Cod, Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard, Vinyl Siding
  • Basement Desc.: Partial, Storage, Partially Finished, Concrete Floor
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,610
  • Above Ground: 3,338 Sq. Ft.
  • Below Ground: 272 Sq. Ft.
  • Year Built: 1900

Lot Features

  • Lot Size (Acres): 0.6
  • Zoning: R-20
  • Lot Description: Treed, Level Lot

Financial Considerations

  • Assessment Amount: $368,410
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 1087354
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

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— 1358 S Main St —

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1358 S Main St

School District:Cheshire School District
NameGradesDistance
Highland School, Cheshire, CT
490 Highland Avenue, Cheshire, CT 06410
1-63 mi
Dodd Middle School
100 Park Place, Cheshire, CT 06410
7-83 mi
Cheshire High School
525 South Main Street, Cheshire, CT 06410
9-121.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1358 S Main St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/31/2026
Listed
$749,000
33.75%
MLS
5/12/2022
Sold
$560,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1358 S Main St

Year
Property Taxes
Change
Tax Assessment
Change
2024
$10,957
8%
$368,410
—
2023
$10,117
10%
$368,410
40%
2023
$9,226
2%
$262,930
—
2022
$9,024
2%
$262,930
—
2021
$8,866
1%
$262,930
—
2020
$8,735
—
$262,930
—
2019
$8,735
2%
$262,930
—
2018
$8,592
2%
$263,400
—
2017
$8,413
2%
$263,400
—
2016
$8,215
2%
$263,400
—
2015
$8,084
1%
$263,400
—
2014
$7,968
4%
$263,400
-5%
2011
$7,638
—
$276,740
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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1358 South Main Street, Cheshire, CT 06410 (MLS# 24159711) is a Single Family property with 4 bedrooms, 4 full bathrooms and 2 partial bathrooms. 1358 South Main Street is currently listed for $749,000 and was received on March 31, 2026. This property is listed by Heidi Hoss from our Old Lyme/Old Saybrook/Essex Office.Want to learn more about 1358 South Main Street? Do you have questions about finding other Single Family real estate for sale in Cheshire? You can browse all Cheshire real estate or contact a Coldwell Banker agent to request more information.

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