1251 South Main Street
Cheshire, Connecticut 06410
Reduced from $599,900
- Beds
- 4
- Baths
- 3
- SqFt
- 3,368
- Acres
- 0.46
- Year Built
- 1968
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
- 45 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
Active Listings
25
38 under contract
Median List Price
$599,000
25 active listings
Median Closed Price
$580,000
252 sales
Median Days on Market
19
25 active listings
Median $ / Sq Ft
$271
25 active listings
Sale-to-List Ratio
102.5%
252 sales
How this home compares
List Price
$575,000
vs $599,000 median
In line with median
Price / Sq Ft
$171
vs $271 median
36.9% below median
Days on Market
45 days
vs 19 days median
26 days longer than median
Based on 25 active and 252 closed sales (trailing 12 mo) of single family in Cheshire. Source: SmartMLS · As of October 10, 2026.
Location
1251 South Main Street, Cheshire, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 8, 2026per month
- Principal & Interest$3,185
- Property Taxes$727
- Insurance$192
- 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
- YesLower 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
- 45
- MLS #
- 24201800
- MLS Status
- Under Contract - Continue to Show
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/10/2026. 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 10/10/2026 at 11:40 PM UTC.