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$779,999 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2,706 Sq. Ft.
  • 2 Car Garage
  • Updated 21 hours ago
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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.

Full Property Details for 275 W Main St

General

  • Price: $779,999
  • Taxes: (July 2026-June 2027)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24211368
  • Updated: 10/2/2026
  • Added to Site: 2 day(s) ago

Interior

  • Number of Rooms: 10
  • Interior Features: Auto Garage Door Opener, Cable - Available, Open Floor Plan, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Electric Range, Microwave, Range Hood, Refrigerator, Freezer, Icemaker, Dishwasher, Disposal

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Full Bath: Main
  • Partial Bath: Lower

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom - Fireplace, Jack & Jill Bath, Upper
  • Bedroom 1: Bedroom, Lower
  • Bedroom 2: Bedroom, Upper
  • Bedroom 3: Bedroom, Upper

Other Rooms

  • Living Room: Living Room, Main
  • Eat In Kitchen: Eat-In Kitchen, Main
  • Dining Room: Dining Room, Main
  • Laundry: Lower Level

Exterior

  • Exterior Features: Shed, Deck, Gutters, Garden Area

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: Middlesex
  • Driving Directions: GPS Friendly

School Information

  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Zoned
  • Water Heater: Electric, 80 Gallon Tank

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Full, Fully Finished
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 2,706
  • Above Ground: 1,906 Sq. Ft.
  • Below Ground: 800 Sq. Ft.
  • Year Built: 1971

Lot Features

  • Lot Size (Acres): 2
  • Zoning: R-2
  • Lot Description: Professionally Landscaped

Financial Considerations

  • Assessment Amount: $343,420
  • Tax Year: July 2026-June 2027

Disclosures and Reports

  • Property ID: 941547

Listed by Great Estates, CT, Shirley Tapper

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Listing agent

— 275 W Main St —

  • Shirley Tapper

    Great Estates, CT

Agent Contact: (475) 202-2586 Office Contact: (203) 200-7030

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Price & Sales History for 275 W Main St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/01/2026
Listed
$779,999
57.58%
MLS
6/17/2026
Sold
$495,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 275 W Main St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$7,471
11%
$275,870
—
2023
$6,745
16%
$275,870
40%
2023
$5,838
1%
$196,570
—
2022
$5,799
—
$196,570
—
2021
$5,799
3%
$196,570
—
2020
$5,626
-1%
$196,570
—
2019
$5,659
5%
$196,570
-1%
2018
$5,384
3%
$198,580
—
2017
$5,235
3%
$198,580
—
2016
$5,078
1%
$198,580
—
2015
$5,028
2%
$198,580
—
2014
$4,929
2%
$198,580
-10%
2011
$4,852
—
$221,030
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Great Estates, CT, Shirley Tapper

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275 West Main Street, Chester, CT 06412 (MLS# 24211368) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 275 West Main Street is currently listed for $779,999 and was received on October 01, 2026. Want to learn more about 275 West Main Street? Do you have questions about finding other Single Family real estate for sale in Chester? You can browse all Chester real estate or contact a Coldwell Banker agent to request more information.

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