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275 West Main Street

Chester, Connecticut 06412

ACTIVE - NEW$715,000
Beds
4
Baths
3 | 1
SqFt
2,706
Acres
2.00
Year Built
1971
Matt Caiola

Matt Caiola

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2-Car Garage3 Fireplaces

About This Home

Discover move-in-ready living in desirable Chester, one of the Connecticut River Valley's most charming towns! Set on two picturesque acres across from Cockaponset State Forest, this beautifully renovated 4-bedroom, 3.5-bath home blends classic New England character with modern comfort, approximately three miles from Chester Village and Cedar Lake. Inside, refinished hardwood floors, multiple fireplaces, and inviting living spaces create a warm welcome, all updated & freshly painted. The stunning new kitchen features, beautiful cabinets, quartz countertops and premium THOR Gordon Ramsay Collection appliances. A first-floor bedroom & full bath offer flexibility for guests or main-level living. Upstairs, the primary suite boasts a fireplace, 6-foot walk-in closet, a spa-inspired bath with a rain shower and soaking tub! Two more bedrooms & yet another newly remodeled full bathroom complete this level. Approximately 800 square feet of permitted finished lower-level space, complete with a fireplace and bathroom adds room to relax, work, or entertain. Major improvements include a NEW SEPTIC SYSTEM, new plumbing, updated electrical with 200-amp service, new windows, siding, and gutters, plus three-zone central heating and air conditioning. Outside, enjoy a new 12' x 12' wood deck, landscaped grounds, and a private pond along the scenic rear approach. Two access points add convenience to this peaceful setting. Beautifully updated & ready to enjoy at an amazing price. Welcome home!

Key Facts

City/Town
Chester
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1971
Days on Market
0 days
Beds
4
Baths
3 full · 1 half
Living Area
2,706 sq ft
Lot Size
2.00 acres
Garage / Parking
2 garage · 9 total
Property Taxes
$9,540 / Annually

Market Snapshot

The Chester Market

Single Family · trailing 12 months

Median Days on Market

33

10 active listings

Median $ / Sq Ft

$279

10 active listings

Sale-to-List Ratio

100.0%

39 sales

How this home compares

List Price

$715,000

vs $739,950 median

In line with median

Price / Sq Ft

$264

vs $279 median

5.4% below median

Days on Market

0 days

vs 33 days median

33 days fresher than median

Based on 10 active and 39 closed sales (trailing 12 mo) of single family in Chester. Source: SmartMLS · As of October 12, 2026.

Location

275 West Main Street, Chester, Connecticut

Property + 4 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,993

per month

  • Principal & Interest$3,960
  • Property Taxes$795
  • Insurance$238
  • HOA$0

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

Location

City/Town
Chester
Neighborhood
N/A
County
Middlesex

Residence

Property Type
Single Family
Style
Colonial
Year Built
1971
New Construction
No/Resale
Living Area
2,706 sq ft
Below Grade
800 sq ft

Schools

Elementary
Per Board of Ed
High
Per Board of Ed

Interior

Heating
ZonedOther
Cooling
Central Air
Fireplaces
3
Laundry
Lower Level
Appliances
Electric RangeMicrowaveRange HoodRefrigeratorFreezerDishwasherDisposal
Basement
FullFully Finished
In-Law Apartment
PossibleLower Level
Interior Features
Cable - AvailableOpen Floor PlanSecurity System

Exterior & Lot

Lot Size
2.00 acres
Zoning
R-2
Garage / Parking
2 garage spaces9 total parking spacesAttached GarageDrivewayPrivatePaved
Waterfront Details
Walk to Water
Water Source
Private Well
Sewer
Septic
Flood Zone
No
Construction
Vinyl Siding
Color
Cream
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
DeckGarden Area
Lot Description
Level Lot

Listing & Financials

Property Taxes
$9,540 / Annually
Days on Market
0
MLS #
24213774
MLS Status
Active
Financing
FHA,VA,CHFA

Similar Properties

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

Listed By

Nancy Bullis

(203) 856-9060

Coldwell Banker Realty

(860) 434-8600

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

The IDX display contains information sourced from SmartMLS, Inc. as of 10/12/2026. 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 10/12/2026 at 9:25 PM UTC.