275 West Main Street
Chester, Connecticut 06412
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 2,706
- Acres
- 2.00
- Year Built
- 1971
- 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
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
Active Listings
10
5 under contract
Median List Price
$739,950
10 active listings
Median Closed Price
$550,000
39 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 8, 2026per 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.
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.