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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 $300,000 - $400,000
$400,000 - $500,000 $500,000 - $600,000 $800,000 - $900,000
Over $1,000,000

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14 Properties Found. Page 1 of 3

This Remarkable Country Home Becomes Available ...

Photo of Listing #170358328

$1,350,000 Deposit

  • 3 Beds
  • 5 Baths
  • 7.08 Acres
  • 3,876 ft²

Residential

260 Middlesex Ave, Chester, CT

MLS® #170358328

This Remarkable Country Home Becomes Available For The First Time In Over 30 Years. Until Recently The Rural Retreat Of A Renowned Journalist, It Is Located In The Charming Small Town Of Chester, Connecticut. New York City And Boston Are Just Over Two Hours...

William Pitt Sotheby's Int'l

Waterfront Living At The Jennings Pond Estate -...

REDUCED 2% Photo of Listing #170227181

$875,000 Show

  • 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 Realty

This Is What Waterfront Living Is Supposed To B...

REDUCED 4% Photo of Listing #170304526

$859,000 Active

  • 3 Beds
  • 2/1 Baths
  • 2.83 Acres
  • 1,978 ft²

Residential

71 Dock Rd, Chester, CT

MLS® #170304526

This Is What Waterfront Living Is Supposed To Be About. Accept No Substitutes. You Cannot Get Much Closer To The Water, Unless You're In A Boat! A Turnkey Ct River Dream Escape From Any And All Of Life's Cares. Lovingly Remodeled From Top To Bottom. Spacio...

William Pitt Sotheby's Int'l

Located On 1.11 Acres In The Quintessential Che...

REDUCED 2% Photo of Listing #170347170

$549,900 Active

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

Residential

24 Pleasant St, Chester, CT

MLS® #170347170

Located On 1.11 Acres In The Quintessential Chester Village, This 1850's Federal Colonial Was Remodeled From The Studs Out In 2004. The Kitchen Has Custom Cherry Cabinets, Granite Countertops And New Mosaic Glass Backsplash. The Cabinets Carry Through Into ...

Coldwell Banker Realty

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

Photo of Listing #170342243

$498,000 Deposit

  • 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...

William Pitt Sotheby's Int'l

With A Fabled History And Successful Present, 5...

REDUCED 4% Photo of Listing #170305943

$475,000 Deposit

  • 1 Beds
  • 1 Baths
  • 0.08 Acres
  • 2,177 ft²

Residential

59 -61 Main St, Chester, CT

MLS® #170305943

With A Fabled History And Successful Present, 59-60 Main Street Is A Prominent Building In The Sought After Village Of Chester. With A Truly Charming Studio Apartment On The Second Floor Befit For A True Entrepreneur, You Can Live Where You Work (or Rental ...

William Pitt Sotheby's Int'l

 

©2021 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.