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1251 South Main Street

Cheshire, Connecticut 06410

ACTIVE - NEW$599,900
Beds
4
Baths
3
SqFt
3,368
Acres
0.46
Year Built
1968
Matt Caiola

Matt Caiola

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2-Car Garage1 Fireplace

About This Home

Exceptional in-law potential with over 3,300 sq ft of finished interior space! Expansive and versatile home offering an ideal setup for extended living, along with numerous updates and amenities. Main level features a sun-filled living room with HW floors and large picture window, dining room with HW flooring and decorative chair rail. Very spacious eat-in kitchen features HW floors, island with cooktop, newer refrigerator and dishwasher, double oven, skylight, garden and Palladian-style window, recessed lighting, wine rack, and direct access to the deck. Primary bedroom offers hardwood flooring, a generous size closet, and private bath, plus two additional upper-level bedrooms. The sizeable lower level provides incredible flexibility with French doors leading to a sunroom/game room, pellet stove, skylights, bonus room with walk-in closet, den with brick wood-burning fireplace, bedroom, full bath, and laundry (newer washer + dryer). The separate in-law-style living area features a full kitchen, tile flooring, pellet stove, full bath, and convenient access to the two-car garage. Exterior highlights include a large, level lot, partially fenced backyard, patio, newer roof, gutters, and garage doors. Additional features include 200-amp electrical service, two pellet stoves, public water + public sewer. A unique opportunity offering space, flexibility, and exceptional potential for multigenerational living! Convenient to the new Norton Blue Ribbon School, shopping + restaurants.

Key Facts

City/Town
Cheshire
Neighborhood
N/A
Property / Style
Single Family · Raised Ranch
Year Built
1968
Days on Market
0 days
Beds
4
Baths
3 full
Living Area
3,368 sq ft
Lot Size
0.46 acres
Garage / Parking
2 garage · 3 total
Property Taxes
$8,726 / Annually

Market Snapshot

The Cheshire Market

Single Family · trailing 12 months

Median Days on Market

44

19 active listings

Median $ / Sq Ft

$271

19 active listings

Sale-to-List Ratio

101.8%

246 sales

How this home compares

List Price

$599,900

vs $669,000 median

10.3% below median

Price / Sq Ft

$178

vs $271 median

34.3% below median

Days on Market

0 days

vs 44 days median

44 days fresher than median

Based on 19 active and 246 closed sales (trailing 12 mo) of single family in Cheshire. Source: SmartMLS · As of August 26, 2026.

Location

1251 South Main Street, Cheshire, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,008

per month

  • Principal & Interest$3,081
  • Property Taxes$727
  • Insurance$200
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Cheshire
Neighborhood
N/A
County
New Haven

Residence

Property Type
Single Family
Style
Raised Ranch
Year Built
1968
New Construction
No/Resale
Living Area
3,368 sq ft
Below Grade
1,789 sq ft

Schools

Elementary
Norton
Middle
Per Board of Ed
High
Cheshire

Interior

Heating
Baseboard
Heat Fuel
Electric
Cooling
Central Air
Fireplaces
1
Laundry
Lower Level
Laundry Location
Laundry room
Appliances
Oven/RangeWall OvenRefrigeratorDishwasherWasherDryer
Basement
FullFully FinishedGarage AccessWalk-out
In-Law Apartment
PossibleLower Level
Interior Features
Cable - Available

Exterior & Lot

Lot Size
0.46 acres
Zoning
R-20A
Garage / Parking
2 garage spaces3 total parking spacesAttached GaragePavedDrivewayPrivateCircularPaved
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Flood Zone
No
Construction
BrickWood
Color
Blue, brick
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
DeckStone WallPatio
Lot Description
Level LotOpen Lot

Listing & Financials

Property Taxes
$8,726 / Annually
Days on Market
0
MLS #
24201800
MLS Status
Active

Similar Properties

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Listed By

Stacey Deangelis

(203) 494-7068

Calcagni Real Estate

(203) 272-1821

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 8/26/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 8/26/2026 at 5:20 PM UTC.