327 West Main Street
Cheshire, Connecticut 06410
- Beds
- 4
- Baths
- 1 | 1
- SqFt
- 2,123
- Acres
- 0.56
- Year Built
- 1850
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
A TRUE SHOWSTOPPER IN CHESHIRE! Welcome to 327 West Main Street, where timeless New England charm meets modern updates! This beautifully refreshed 4-bedroom, 2-full-bath home offers the character and craftsmanship you love in an older home, with the updates and conveniences today's buyers are looking for. From the moment you arrive, you'll appreciate the attention to detail throughout. Recent improvements include new windows, gutters, fresh interior paint, an on-demand hot water system, and a new mini-split system for year-round comfort and efficiency. Step outside and get ready to enjoy your own backyard retreat, complete with a brand-new above-ground pool and deck, perfect for summer entertaining! You'll also love the covered front and rear porches, ideal for enjoying your morning coffee or unwinding at the end of the day. And just when you think you've seen it all, there's MORE! The detached 3-car garage is an incredible bonus, featuring an epoxy floor and finished loft space above. Whether you're looking for a home office, fitness space, art studio, workshop, or simply extra room for your hobbies, the possibilities are endless! Homes offering this much character, versatility, and modern convenience don't come along every day. Move right in and start enjoying everything this unique Cheshire property has to offer!
Key Facts
- City/Town
- Cheshire
- Neighborhood
- N/A
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1850
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 1 full · 1 half
- Living Area
- 2,123 sq ft
- Lot Size
- 0.56 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $7,242 / Annually
Market Snapshot
The Cheshire Market
Single Family · trailing 12 months
Active Listings
24
47 under contract
Median List Price
$637,000
24 active listings
Median Closed Price
$585,000
243 sales
Median Days on Market
34
24 active listings
Median $ / Sq Ft
$292
24 active listings
Sale-to-List Ratio
103.0%
243 sales
How this home compares
List Price
$595,000
vs $637,000 median
6.6% below median
Price / Sq Ft
$280
vs $292 median
In line with median
Days on Market
0 days
vs 34 days median
34 days fresher than median
Based on 24 active and 243 closed sales (trailing 12 mo) of single family in Cheshire. Source: SmartMLS · As of October 29, 2026.
Location
327 West Main Street, Cheshire, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 22, 2026per month
- Principal & Interest$3,270
- Property Taxes$604
- Insurance$198
- 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
- Cape Cod
- Year Built
- 1850
- New Construction
- No/Resale
- Living Area
- 2,123 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- Natural Gas
- Cooling
- Central AirSplit System
- Laundry
- Main Level
- Appliances
- Oven/RangeRefrigeratorDishwasherWasherDryer
- Basement
- PartialUnfinished
- In-Law Apartment
- No
Exterior & Lot
- Lot Size
- 0.56 acres
- Zoning
- R-20
- Garage / Parking
- 3 garage spacesDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Pool
- VinylAbove Ground Pool
- Construction
- Vinyl Siding
- Color
- yellow
- Roof
- Asphalt Shingle
- Foundation
- ConcreteStone
- Lot Description
- Level LotCleared
Listing & Financials
- Property Taxes
- $7,242 / Annually
- Days on Market
- 0
- MLS #
- 24217571
- MLS Status
- Active
Similar Properties
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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 10/29/2026. 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 10/29/2026 at 2:50 AM UTC.