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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 $800,000 - $900,000
$900,000 - $1,000,000

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18 Properties Found. Page 1 of 3

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

Secluded, 5.3 Acres Of Lightly Wooded Property ...

Photo of Listing #170249194

$575,000 Active

  • 3 Beds
  • 3 Baths
  • 5.38 Acres
  • 2,180 ft²

Residential

47 Ferry Rd, Chester, CT

MLS® #170249194

Secluded, 5.3 Acres Of Lightly Wooded Property With Over 200 Feet On The Connecticut Riverfront. Located Near The Chester/hadlyme Ferry With Views Of Gillette Castle. Potential For Subdivision If Desired, As Well As Possible Dock On The Connecticut River. ...

William Pitt Sotheby's Int'l

A Stunning & Private True 4 Bedroom + Bonus Roo...

REDUCED 4% Photo of Listing #170237424

$499,999 Active

  • 4 Beds
  • 3/1 Baths
  • 2.01 Acres
  • 3,396 ft²

Residential

28 Hoop Pole Hill Rd, Chester, CT

MLS® #170237424

A Stunning & Private True 4 Bedroom + Bonus Room, Cape/colonial Style Home In Bucolic Chester. With Over $37,000 In Recent Improvements, This Home Has Been Meticulously Maintained By Its Current Stewards To The Highest Standards. Pottery Barn Decor/colors, ...

William Raveis Real Estate

As You Drive Up The Driveway, You Are Captured ...

REDUCED 5% Photo of Listing #170242798

$499,000 Active

  • 3 Beds
  • 2 Baths
  • 9.2 Acres
  • 2,452 ft²

Residential

80 Goose Hill Rd, Chester, CT

MLS® #170242798

As You Drive Up The Driveway, You Are Captured By The Quintessential New England 1850 Colonial Built By A. Webb...and, The View!!!! Gilette's Castle, In Its Full Glory, Can Be Seen Clearly During All Seasons. The Fall Foliage, Sunrises, The Field, And Dur...

William Pitt Sotheby's Int'l

Chester Village Cash Cow! Annual Rental Potenti...

REDUCED 3% Photo of Listing #170192098

$475,000 Show

  • 5 Beds
  • 3/2 Baths
  • 0.19 Acres
  • 3,531 ft²

Residential

45 Main St, Chester, CT

MLS® #170192098

Chester Village Cash Cow! Annual Rental Potential Of $60k Gross. Beautifully Restored 3 Unit Building With Charm And Character Overlooking The Beautiful Pattaconk River. Live For Free In One Unit And Rent Out The Rest Or Rent All Three. The Middle Unit Is...

Coldwell Banker Residential Br

 

©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.