275 West Main Street, Chester, CT 06412 - Photo 1

1/1

$495,000

Sold
Closed
Single Family
4 Beds
2 Full Baths
1,906 Sq. Ft.
2 Car Garage

1/1

Property Description

***Multiple offers received. Seller has asked for best and final by Monday 5/18 5pm*** Set on an exceptional 2-acre parcel in the charming Connecticut River town of Chester, this 4-bedroom, 2-bath Colonial offers endless potential in a truly special setting. Being offered for the first time in 55 years, this well-loved home is filled with warmth and character throughout, featuring hardwood floors and three fireplaces, including one in the spacious primary bedroom. Mature plantings surround the property, creating a peaceful outdoor backdrop complete with a pond perfect for relaxing and enjoying nature. Additional highlights include an attached 2-car garage, two shed/barn outbuildings, and newer major mechanical updates including the roof, furnace, and oil tank. The home also offers finished space in the basement complete with a fireplace, ideal for entertaining, a home office, or flexible additional living space. Located directly across the street from Cockaponset State Forest, this property is ideal for those who appreciate outdoor recreation and nature. Whether you're looking to preserve its timeless charm or add your own finishing touches, this is an exceptional opportunity to make it your own. Enjoy all that Chester has to offer, including acclaimed restaurants, art galleries, unique local shops, and the charm of one of Connecticut's most beloved river towns.

Full Property Details

Full Property Details for 275 W Main St

General

Sold For: $495,000
Taxes: (July 2025-June 2026)
Status: Closed
Type: Single Family
Source: SMARTMLS
MLS ID: 24173958
Added to Site: 57 day(s) ago

Interior

Number of Rooms: 10
Rooms/Areas: Laundry Room
Fireplace: Yes
Number of Fireplaces: 3
Appliances: Oven/Range, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

Total Bathrooms: 2
Full Bathrooms: 2
Full Bath: 7.5 x 11.7, Main

Bedrooms

Total Bedrooms: 4
Primary Bedroom: Primary Bedroom - Fireplace, Hardwood Floor, 16.1 x 11.7, Upper
Bedroom 1: Bedroom - Hardwood Floor, 11.1 x 10.9, Upper
Bedroom 2: Bedroom - Hardwood Floor, 11.8 x 11.7, Upper
Bedroom 3: Bedroom - Hardwood Floor, 11.9 x 10.8, Upper

Other Rooms

Living Room: Living Room - Fireplace, Hardwood Floor, 19.5 x 11.7, Main
Family Room: Family Room - French Doors, Hardwood Floor, 12.1 x 10.9, Main
Kitchen: Kitchen - Hardwood Floor, 11.5 x 10.8, Main
Dining Room: Dining Room - Hardwood Floor, 11.6 x 10.9, Main
Game room: Yes
Game Room: Rec/Play Room - Fireplace, 22.11 x 22.5, Lower
Rec Room: Fireplace, 22.11 x 22.5, Lower
Laundry: Lower Level
Other Room 1: Other, 9.1 x 14.6, Main

Exterior

Exterior Features: Shed, 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: Chester
Middle School: Winthrop
High School: Valley

Heating & Cooling

Cooling Type: Window Unit
Heating Type: Hot Water, Oil
Heating Fuel: Oil
Water Heater: Domestic

Utilities

Sewer: Septic
Water: Private Well

Structural Information

Architectural Style: Colonial
Construction Status: No/Resale
Exterior Const.: Wood
Basement Desc.: Full, Partially Finished
Roof: Asphalt Shingle
Attic: Yes
Square Feet: 1,906
Above Ground: 1,906 Sq. Ft.
Year Built: 1971

Lot Features

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

Financial Considerations

Assessment Amount: $275,870
Tax Year: July 2025-June 2026

Disclosures and Reports

Property ID: 941547

Listed by Puorro Realty Group, Kelly Puorro and Puorro Realty Group, Brandon Puorro
Sold by Great Estates, CT, Donna Genovese

What's Your Home Worth?

* Indicates a required field

For a complimentary comparative market analysis, please contact us so we can discuss your home's value.

Your Property Information

Address optional

City *State *

Zip Code optional

Your Contact Information

First Name *Last Name *

Email Address *

Phone Number *

Location of interest

Comment *

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 Submit, 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.

Listing agents

— 275 W Main St —

Kelly Puorro

Puorro Realty Group
Brandon Puorro

Puorro Realty Group

Agent Contact: (860) 575-8666 Office Contact: (860) 558-9740

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender

NMLS#: 1598647

Get Pre-Approved

Schools

Schools serving 275 W Main St

School Districts:Chester School District, Regional High School District 04

Name	Grades	Distance
Chester Elementary School, Chester, CT 23 Ridge Road, Chester, CT 06412	K-6	4.4 mi
John Winthrop Middle School 1 Winthrop Road, Deep River, CT 06417	7-8	3.6 mi
Valley Regional High School 256 Kelsey Hill Road, Deep River, CT 06417	9-12	3.9 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 275 W Main St

Date

Details

Price

Change

Source

6/05/2026

Sold

$495,000

2.06%

MLS

5/13/2026

Listed

$485,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

89 Falls Landing Rd, Deep River, CT 06417 - Photo 1

Just Listed

$749,900

Open House

89 Falls Landing Rd Deep River, CT 06417

Single Family
Active
Updated 3 hours ago

4
Beds
3
Total Baths
3,204
Sq. Ft.

Listed by William Raveis Real Estate

79 River St, Deep River, CT 06417 - Photo 1

Just Listed

$399,900

79 River St Deep River, CT 06417

Single Family
Active
Updated 3 days ago

2
Beds
1
Total Bath
1,817
Sq. Ft.

Listed by Compass Connecticut, LLC

614 Route 81, Killingworth, CT 06419 - Photo 1

Just Listed

$839,000

Open House

614 Route 81 Killingworth, CT 06419

Single Family
Active
Updated 2 days ago

4
Beds
3
Total Baths
3,012
Sq. Ft.

Listed by Shelly Cumpstone (860) 434-8600

302 Route 81, Killingworth, CT 06419 - Photo 1

Just Listed

$695,000

302 Route 81 Killingworth, CT 06419

Single Family
Active
Updated 1 day ago

3
Beds
3
Total Baths
1,726
Sq. Ft.

Listed by Shelly Cumpstone (860) 434-8600

93 Book Hill Rd, Essex, CT 06426 - Photo 1

Price Reduced

-$10,000 (-2.44%)

$400,000

93 Book Hill Rd Essex, CT 06426

Single Family
Active
Updated 6 days ago

3
Beds
3
Total Baths
1,572
Sq. Ft.

Listed by Innovation Propeties, LLC

Price Reduced

-$450,000 (-10.47%)

$3,850,000

7 Hanna Ln Essex, CT 06426

Single Family
Active
Updated 21 hours ago

3
Beds
4
Total Baths
4,383
Sq. Ft.

Listed by William Pitt Sotheby's Int'l

46 School Hill Ln, Westbrook, CT 06498 - Photo 1

Price Reduced

-$10,000 (-1.76%)

$559,000

46 School Hill Ln Westbrook, CT 06498

Single Family
Active
Updated 1 day ago

4
Beds
3
Total Baths
2,594
Sq. Ft.

Listed by Derek Greene

48 Grove Way, Clinton, CT 06413 - Photo 1

Price Reduced

-$110,000 (-8.63%)

$1,165,000

48 Grove Way Clinton, CT 06413

Single Family
Active
Updated 2 days ago

3
Beds
4
Total Baths
1,603
Sq. Ft.

Listed by Lyman Real Estate

42 Parker Hill Rd, Killingworth, CT 06419 - Photo 1

Sold

$518,000

42 Parker Hill Rd Killingworth, CT 06419

Single Family
Closed
Updated 12 days ago

3
Beds
2
Total Baths
1,842
Sq. Ft.

Listed by Shelly Cumpstone
Sold by William Raveis Real Estate

7 Hickory Hill Dr, Chester, CT 06412 - Photo 1

Sold

$549,000

7 Hickory Hill Dr Chester, CT 06412

Single Family
Closed

3
Beds
3
Total Baths
2,202
Sq. Ft.

Listed by Re/Max Valley Shore
Sold by William Raveis Real Estate

545 N Roast Meat Hill Rd, Killingworth, CT 06419 - Photo 1

Sold

$430,000

545 N Roast Meat Hill Rd Killingworth, CT 06419

Single Family
Closed

3
Beds
2
Total Baths
2,226
Sq. Ft.

Listed by William Raveis Real Estate
Sold by William Raveis Real Estate

172 Parker Hill Rd, Killingworth, CT 06419 - Photo 1

Sold

$535,000

172 Parker Hill Rd Killingworth, CT 06419

Single Family
Closed

4
Beds
3
Total Baths
2,815
Sq. Ft.

Listed by Exceptional Real Estate LLC
Sold by Bishop, Edward & Roberts, LLC

275 West Main Street, Chester, CT 06412 (MLS# 24173958) is a Single Family property that was sold at $495,000 on June 05, 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.

275 W Main St Chester, CT 06412