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
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
Active Listings
8
6 under contract
Median List Price
$772,450
8 active listings
Median Closed Price
$565,000
38 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 1, 2026per 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
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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 10/3/2026. 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.