Skip to main content

327 West Main Street

Cheshire, Connecticut 06410

ACTIVE - NEW$595,000
Beds
4
Baths
1 | 1
SqFt
2,123
Acres
0.56
Year Built
1850
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

Request a private showing and get Matt's read on price, condition, and next steps.

Call Matt
Pool3-Car Garage

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,072

per 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

Homes with a close match in area, property type, and price.

Listed By

Dave Jones

(203) 910-2638

Dave Jones Realty, LLC

(203) 758-0264

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.