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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 $200,000 - $300,000 $300,000 - $400,000
$400,000 - $500,000 $500,000 - $600,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000

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30 Properties Found. Page 1 of 5

Waterfront Living At The Jennings Pond Estate -...

Photo of Listing #170227181

$950,000 Active

  • 3 Beds
  • 3 Baths
  • 0.75 Acres
  • 3,545 ft²

Residential

19 West Main St, Chester, CT

MLS® #170227181

Waterfront Living At The Jennings Pond Estate - A True Hidden Gem! A Phenomena Of History, Nature, And Architecture Privately Tucked Away In Historic Chester Village. This Charming Contemporary French Country Retreat Built In 1999 Overlooks Jennings Pond A...

Coldwell Banker Residential Br

Brimming With Charm & Character, This Custom Bu...

Photo of Listing #170227195

$899,900 Active

  • 4 Beds
  • 4/2 Baths
  • 5.86 Acres
  • 6,350 ft²

Residential

134 Pinnacle Ln, Chester, CT

MLS® #170227195

Brimming With Charm & Character, This Custom Built And Well Maintained Adirondack Shingle Style Home Offers The Perfect Blend Of Traditional Architecture And Modern Home Design. Meticulous Craftsmanship, Quality Materials And Vaulted Ceilings Throughout Add...

Coldwell Banker Residential Br

Luxury Home Set High Above The Picturesque Vill...

REDUCED 4% Photo of Listing #170190700

$899,900 Active

  • 5 Beds
  • 5/2 Baths
  • 2.75 Acres
  • 6,054 ft²

Residential

18 East Liberty St, Chester, CT

MLS® #170190700

Luxury Home Set High Above The Picturesque Village Of Chester, Ct With It's Upscale Restaurants And Country Shops. The Approach Down This Driveway Gives You The Feeling Of A Country Estate. The Moment You Enter This Home You'll Be In Awe Of The Elegance, It...

William Raveis Real Estate

This Beautiful Two Floor Custom Design Home By ...

Photo of Listing #170092064

$799,900 Active

  • 4 Beds
  • 3/1 Baths
  • 4.1 Acres
  • 3,307 ft²

Residential

201 Pinnacle Ln, Chester, CT

MLS® #170092064

This Beautiful Two Floor Custom Design Home By Asw Incorporates The Attributes Of A Home Built For Entertaining With Main Floor Master Suite And Laundry To Suit An Age-in-place Lifestyle. The Interior Has Nine Foot Ceilings Atop An Impressive Open- Concept ...

Williams Realty Services

Oakfield Farm, You'll First Notice The Beautifu...

REDUCED 3% Photo of Listing #170164589

$599,000 Active

  • 3 Beds
  • 2/1 Baths
  • 25.6 Acres
  • 1,644 ft²

Residential

42 Winthrop Rd, Chester, CT

MLS® #170164589

Oakfield Farm, You'll First Notice The Beautiful Stone Walls And Entry. Running Horse Sculptures Adorn The First Pasture As You Head Into The Rest Of This 25 Acre Horse Farm. Sitting Back Off The Road Is A 1644 Sf 3 Bedroom 2.1 Bath Home With Master Bedr...

William Raveis Real Estate

Sun-filled Contemporary Home In One Of Chester’...

Photo of Listing #170206129

$595,000 Show

  • 3 Beds
  • 2/2 Baths
  • 0.79 Acres
  • 3,277 ft²

Residential

26 Spring St, Chester, CT

MLS® #170206129

Sun-filled Contemporary Home In One Of Chester’s Most Beautiful Settings Where Jennings Pond Flows Over A Stunning Waterfall Into The Pattaconk Brook. The Home Is Integrated Into The Spectacular Setting, With Room Placement, Windows, Decks And Terraces Des...

William Pitt Sotheby's Int'l

 

©2019 Listings courtesy of the Connecticut Multiple Listing Service, Inc.

IDX information is provided exclusively for consumers' personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Listing data is deemed reliable but is not guaranteed accurate by the MLS.