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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 $900,000 - $1,000,000

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15 Properties Found. Page 1 of 3

Ct River Waterfront! Well Maintained Three Bedr...

Photo of Listing #170383743

$995,000 Active

  • 3 Beds
  • 2 Baths
  • 3.87 Acres
  • 1,888 ft²


9 Parkers Point Rd, Chester, CT

MLS® #170383743

Ct River Waterfront! Well Maintained Three Bedroom Cape With Charming Guest Cottage On Nearly 4 Acres Gently Sloping To The Ct River. Over 300 Ft Of Frontage In A No Wake Zone. Beautiful Views And Setting! The Main House Has Two First Floor Bedrooms Includi...

Craig Milton

Welcome Home To 16 Gilbert Hill. This Light An...

Photo of Listing #170394688

$650,000 Under Contract - Continue To Show

  • 4 Beds
  • 2/1 Baths
  • 1.01 Acres
  • 4,100 ft²


16 Gilbert Hill Rd, Chester, CT

MLS® #170394688

Welcome Home To 16 Gilbert Hill. This Light And Bright Custom Colonial Welcomes You With An Open Floor Plan, Soaring Ceilings And Walls Of Windows. Spaces Flow Seamlessly From One Room To The Next. The Great-room Truly Is The Heart Of The Home With A Gas...

Kyle S Hinding

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


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

This Charming Colonial Is Nestled In A Quiet Cu...

Photo of Listing #170394230

$496,500 Under Contract

  • 3 Beds
  • 2/1 Baths
  • 1.36 Acres
  • 2,256 ft²


3 Brooks Ln, Chester, CT

MLS® #170394230

This Charming Colonial Is Nestled In A Quiet Cul-de-sac Conveniently Located By The Picturesque Village Of Chester. Light, Bright And Meticulously Maintained, This Home Checks All The Boxes. Beautiful, Open Floor Plan, With Many Upgrades, Plenty Of Space To...

Dean A. Mitchell

Wonderful Chester Village Home Steps To Everyth...

REDUCED 1% Photo of Listing #170395379

$489,900 Under Contract - Continue To Show

  • 3 Beds
  • 2/1 Baths
  • 1.11 Acres
  • 2,302 ft²


24 Pleasant St, Chester, CT

MLS® #170395379

Wonderful Chester Village Home Steps To Everything - New Roof Just Add In 2021 And Home Is In Excellent Move In Condition. Located On 1.11 Acres In The Quintessential Chester Village, This 1850's Federal Colonial Was Remodeled From The Studs Out In 2004. Th...

Joel Lucas


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 June 13th, 2021 at 10:08am EDT.