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Chester Homes For Sale

Chester is part of what the locals call the “Tri-Town Area” made up of Deep River, Essex, and Chester. With a population of about 3,800 and consisting of 16.8 square miles, Chester is located on the Western Bank of the Connecticut River in Middlesex County. Downtown Chester is picturesque and offers 19th century charm with a melody of shops, eateries and a creative spirit that is captured by the artists, artisans and neighbors alike. The town of Chester also has lakes, ponds, cascading waterfalls, a state forest, marinas, and even a small airport. Students attend these Chester Schools: Chester Elementary School, John Winthrop Middle School and Valley Regional High School.

Property Results

All Listings $100,000 - $200,000 $200,000 - $300,000
$300,000 - $400,000 $400,000 - $500,000 $500,000 - $600,000
$600,000 - $700,000 $700,000 - $800,000 Over $1,000,000

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12 Properties Found. Page 1 of 2

Resort Like Lifestyle Available In This Spectac...

REDUCED 10% Photo of Listing #170410397

$1,299,000 Under Contract - Continue To Show

  • 3 Beds
  • 3 Baths
  • 48.6 Acres
  • 2,893 ft²

Residential

81 Turkey Hill Rd, Chester, CT

MLS® #170410397

Resort Like Lifestyle Available In This Spectacular Cedar Clapboard Colonial On 48.6 Acres With A Salt Water Pool, Pool House With Covered Patio, Stone Pizza Oven, Hot Tub, Stone Patios, 1792 Sq Ft Barn, Basketball Hoop, & Even Its Own Ball Field. Situated ...

Kristian J Cole

Own A Piece Of History!!! Rare Opportunity To O...

Photo of Listing #170450411

$799,000 Active

  • 5 Beds
  • 2 Baths
  • 1.7 Acres
  • 21,433 ft²

Residential

33 Liberty St, Chester, CT

MLS® #170450411

Own A Piece Of History!!! Rare Opportunity To Own 21,000 Plus Sq. Ft. Building Situated On The Picturesque Great River-tranquility & Privacy In An Area Of Exquisite Homes. Liberty Street Is Minutes To The Quaint, Historic Town Of Chester, Ct. M.s. Brooks & ...

Derek Eisenberg

This Custom Built Home Should Check Most Of You...

Photo of Listing #170454200

$665,000 Active

  • 4 Beds
  • 2/1 Baths
  • 3.01 Acres
  • 2,812 ft²

Residential

11 High Field Ln, Chester, CT

MLS® #170454200

This Custom Built Home Should Check Most Of Your Boxes! This Home Is Located On A Quiet Cul-de-sac Lane. Back Of Property Borders 103 Acres Of Watershed Property, Never To Be Built On. There Are So Many Options For You On 3 Level Acres. Enjoy Every Aspe...

Michelle Macneil

Amazing Opportunity To Own Over 24 Acres Of Pri...

REDUCED 3% Photo of Listing #170439447

$549,900 Active

  • 4 Beds
  • 2/1 Baths
  • 24.89 Acres
  • 3,617 ft²

Residential

107 West Main St, Chester, CT

MLS® #170439447

Amazing Opportunity To Own Over 24 Acres Of Private Property In Chester Set High And Dry Above A Windy Babbling Brook! Sought After Pretty Barn Style Home With Open Floor Plan, Country Kitchen With Antique Brick Wood-fired Oven & 2 Car Garage. This 4 Bedroo...

Jodi Lisitano

This Unique Property, Once A Cider Mill And Orc...

Photo of Listing #170342243

$498,000 Under Contract

  • 5 Beds
  • 3/1 Baths
  • 6.26 Acres
  • 3,273 ft²

Residential

96 Middlesex Ave, Chester, CT

MLS® #170342243

This Unique Property, Once A Cider Mill And Orchard, Includes A Barn Style Home, Circa 1830, On 6 Open And Landscaped Acres. Perfect Getaway With Multiple Outdoor Living Areas Including A Wrap Around Deck With Outdoor Kitchen, Patios, And 2 Gazebos. The P...

Donn Holland

So Much Charm Throughout This Absolutely Stunni...

REDUCED 2% Photo of Listing #170456071

$479,900 Active

  • 5 Beds
  • 2 Baths
  • 0.74 Acres
  • 2,000 ft²

Residential

76 Middlesex Ave, Chester, CT

MLS® #170456071

So Much Charm Throughout This Absolutely Stunning, Completely Remodeled Farmhouse/colonial. Home Is Set Back From The Road And Walking Distance To Downtown Chester. Home Features 4 /5 Bedrooms And 2 Full Baths. Almost Everything In This Spectacular Home I...

Tracey A Precourt

 

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed.
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Listing information last updated on January 25th, 2022 at 5:53pm EST.