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275 West Main Street

Chester, Connecticut 06412

ACTIVE - NEW$779,999
Beds
4
Baths
3 | 1
SqFt
2,706
Acres
2.00
Year Built
1971
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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About This Home

Completely Reimagined * 4 Bedrooms * 3.5 Bathrooms * 2 Acres * Luxury Primary Suite * Finished Lower Level Welcome to 275 W Main Street, where classic New England charm meets a stunning, comprehensive renovation. Set on 2 beautiful acres directly across from Cockaponset State Forest, this exceptional Chester home has been thoughtfully transformed to deliver modern luxury, comfort, and effortless turnkey living. From the moment you step inside, you'll notice the attention to detail. Beautifully refinished hardwood floors flow throughout the home, complementing bright, open living spaces designed for both everyday comfort and entertaining. Multiple fireplaces preserve the warmth and character of the original home while the extensive upgrades bring it firmly into the modern era. At the heart of the home is a show-stopping new kitchen, beautifully appointed with quartz countertops and premium THOR Gordon Ramsay Collection appliances. Whether you're hosting family and friends or enjoying a quiet evening at home, this kitchen was designed to impress. Retreat upstairs to the luxurious primary suite, complete with a 6-foot walk-in closet and custom closet system. The spa-inspired primary bathroom creates your own private escape, featuring a custom rain shower and freestanding soaking tub-the perfect place to unwind. And the living space doesn't stop upstairs. The approximately 800-square-foot permitted finished lower level has been transformed.

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
Property Taxes
$9,540 / Annually

Market Snapshot

The Chester Market

Single Family · trailing 12 months

Median Days on Market

32

8 active listings

Median $ / Sq Ft

$288

8 active listings

Sale-to-List Ratio

100.0%

38 sales

How this home compares

List Price

$779,999

vs $772,450 median

In line with median

Price / Sq Ft

$288

vs $288 median

In line with median

Days on Market

0 days

vs 32 days median

32 days fresher than median

Based on 8 active and 38 closed sales (trailing 12 mo) of single family in Chester. Source: SmartMLS · As of October 3, 2026.

Location

275 West Main Street, Chester, Connecticut

Property + 3 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,324

per month

  • Principal & Interest$4,269
  • Property Taxes$795
  • Insurance$260
  • 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
Zoned
Cooling
Central Air
Fireplaces
3
Laundry
Lower Level
Appliances
Electric RangeMicrowaveRange HoodRefrigeratorFreezerIcemakerDishwasherDisposal
Basement
FullFully Finished
Interior Features
Auto Garage Door OpenerCable - AvailableOpen Floor PlanSecurity System

Exterior & Lot

Lot Size
2.00 acres
Zoning
R-2
Garage / Parking
2 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
ShedDeckGuttersGarden Area
Lot Description
Professionally Landscaped

Listing & Financials

Property Taxes
$9,540 / Annually
Days on Market
0
MLS #
24211368
MLS Status
Active

Similar Properties

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Listed By

Shirley Tapper

(475) 202-2586

Great Estates, CT

(203) 200-7030

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

The IDX display contains information sourced from SmartMLS, Inc. as of 10/3/2026. 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 10/3/2026 at 12:20 AM UTC.