Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$715,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2,706 Sq. Ft.
  • 2 Car Garage
  • Updated 55 minutes ago
See This Home
Save This Home
See This Home
Save 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!

Full Property Details for 275 W Main St

General

  • Price: $715,000
  • Taxes: (July 2026-June 2027)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24213774
  • Updated: Today (10/12/2026)
  • Added to Site: Today

Interior

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

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 4
  • Primary Suite: Remodeled, Bedroom Suite, Full Bath, Upper
  • Bedroom 1: Bedroom, Main
  • Bedroom 2: Bedroom, Upper
  • Bedroom 3: Bedroom - Remodeled, Upper

Other Rooms

  • Living Room: Living Room - Remodeled, Fireplace, Hardwood Floor, Main
  • Family Room: Family Room - Remodeled, Fireplace, Vinyl Floor, Lower
  • Eat In Kitchen: Eat-In Kitchen - Remodeled, Quartz Counters, Main
  • Dining Room: Dining Room - Remodeled, Balcony/Deck, Sliders, Hardwood Floor, Main
  • Laundry: Lower Level

Exterior

  • Exterior Features: Deck, Garden Area
  • Color: Cream

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 9
  • Parking: Attached Garage, Driveway

Location

  • County: Middlesex
  • Driving Directions: GPS Friendly

School Information

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

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Zoned, Other
  • 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
  • Driveway/Sidewalk: Private, Paved
  • Zoning: R-2
  • Lot Description: Level Lot

Water Features

  • Water Front Desc.: Walk to Water

Green Features

  • Energy Features: Energy Star Rated, Programmable Thermostat, Thermopane Windows

Financial Considerations

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

Disclosures and Reports

  • Property ID: 941547
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Meet the listing agent

Meet the listing agent
— 275 W Main St —

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
10/12/2026
Listed
$715,000
44.44%
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.

Estimate the Cost for 275 W Main St

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Similar Properties near 275 W Main St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

42 Straits Rd, Chester, CT 06412 - Photo 1 Just Listed
$699,000

42 Straits Rd  Chester, CT 06412

  • Single Family
  • Active
  • Updated 5 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,882
    Sq. Ft.
Listed by Great Estates, CT
77 Falls Landing Rd, Deep River, CT 06417 - Photo 1
$699,900

77 Falls Landing Rd  Deep River, CT 06417

  • Single Family
  • Active
  • 4
    Beds
  • 3
    Total Baths
  • 3,143
    Sq. Ft.
Listed by William Raveis Real Estate
13 High Field Ln, Chester, CT 06412 - Photo 1
$764,900

13 High Field Ln  Chester, CT 06412

  • Single Family
  • Active
  • 4
    Beds
  • 3
    Total Baths
  • 2,662
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l
502 Killingworth-Durham Rd, Killingworth, CT 06419 - Photo 1
$689,000
Open House

502 Killingworth-Durham Rd  Killingworth, CT 06419

  • Single Family
  • Active
  • 5
    Beds
  • 4
    Total Baths
  • 2,518
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l

Just Listed near 275 W Main St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

16 Country Club Trail, Killingworth, CT 06419 - Photo 1 Just Listed
$106,000

16 Country Club Trail  Killingworth, CT 06419

  • Mobile Home
  • Active
  • Updated 5 hours ago
  • 1
    Bed
  • 1
    Total Bath
  • 720
    Sq. Ft.
Listed by The Hometown Team at Coldwell Banker Realty (860) 434-8600
46 Sima Rd, Haddam, CT 06441 - Photo 1 Just Listed
$374,900

46 Sima Rd  Haddam, CT 06441

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,908
    Sq. Ft.
Listed by The Hometown Team at Coldwell Banker Realty (860) 434-8600
6 High St, Haddam, CT 06441 - Photo 1 Just Listed
$130,000

6 High St  Haddam, CT 06441

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,085
    Sq. Ft.
Listed by Michael Hvizdo (917) 721-1332
400 Hidden Lake Rd, Haddam, CT 06441 - Photo 1 Just Listed
$379,900

400 Hidden Lake Rd  Haddam, CT 06441

  • Single Family
  • Active
  • Updated 3 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,656
    Sq. Ft.
Listed by Re/Max Valley Shore

Price Reduced near 275 W Main St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

24 Long Hill Rd, Deep River, CT 06417 - Photo 1 Price Reduced
-$19,600 (-3.77%)
$499,900

24 Long Hill Rd  Deep River, CT 06417

  • Single Family
  • Active
  • Updated 5 hours ago
  • 4
    Beds
  • 2
    Total Baths
  • 2,523
    Sq. Ft.
Listed by Puorro Realty Group
79 Chestnut Hill Rd, Killingworth, CT 06419 - Photo 1 Price Reduced
-$75,000 (-9.09%)
$749,900

79 Chestnut Hill Rd  Killingworth, CT 06419

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,069
    Sq. Ft.
Listed by William Raveis Real Estate
38 Little City Rd, Killingworth, CT 06419 - Photo 1 Price Reduced
-$14,000 (-4.32%)
$310,000

38 Little City Rd  Killingworth, CT 06419

  • Single Family
  • Active
  • Updated 9 hours ago
  • 3
    Beds
  • 1
    Total Bath
  • 1,082
    Sq. Ft.
Listed by Margaret Bennett Realty
25 Whitewood Rd, Killingworth, CT 06419 - Photo 1 Price Reduced
-$25,900 (-22.35%)
$90,000

25 Whitewood Rd  Killingworth, CT 06419

  • Mobile Home
  • Active
  • Updated 4 days ago
  • 2
    Beds
  • 1
    Total Bath
  • 672
    Sq. Ft.
Listed by Property Works New England

Recent Sales near 275 W Main St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

16 Sypher Rd, Chester, CT 06412 - Photo 1 Sold
$616,000

16 Sypher Rd  Chester, CT 06412

  • Single Family
  • Closed
  • 2
    Beds
  • 3
    Total Baths
  • 1,726
    Sq. Ft.
Listed by Peg Mitchel and Kyle Hinding
Sold by Berkshire Hathaway NE Prop.
226 Middlesex Ave, Chester, CT 06412 - Photo 1 Sold
$695,000

226 Middlesex Ave  Chester, CT 06412

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,029
    Sq. Ft.
Listed by Peg Mitchel and Kyle Hinding
Sold by The Hometown Team at Coldwell Banker Realty
11 Parker Hill Rd, Killingworth, CT 06419 - Photo 1 Sold
$737,000

11 Parker Hill Rd  Killingworth, CT 06419

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 2,349
    Sq. Ft.
Listed by Century 21 Classic Homes
Sold by Realty ONE Group Connect
29 Welsch Farms Rd, Killingworth, CT 06419 - Photo 1 Sold
$775,000

29 Welsch Farms Rd  Killingworth, CT 06419

  • Single Family
  • Closed
  • 5
    Beds
  • 4
    Total Baths
  • 4,145
    Sq. Ft.
Listed by William Raveis Real Estate
Sold by The Hometown Team at Coldwell Banker Realty

275 West Main Street, Chester, CT 06412 (MLS# 24213774) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 275 West Main Street is currently listed for $715,000 and was received on October 12, 2026. This property is listed by Nancy Bullis from our Old Lyme/Old Saybrook/Essex Office.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.

Tour this property