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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
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21 Properties Found. Page 1 of 4

This Remarkable Country Home Becomes Available ...

Photo of Listing #170339824

$1,450,000 Show

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

Residential

260 Middlesex Ave, Chester, CT

MLS® #170339824

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

Ct River Waterfront! Well Maintained Three Bedr...

REDUCED 11% Photo of Listing #170331511

$1,150,000 Active

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

Residential

9 Parkers Point Rd, Chester, CT

MLS® #170331511

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...

REMAX Valley Shore Genovali RE

Waterfront Living At The Jennings Pond Estate -...

REDUCED 2% Photo of Listing #170227181

$875,000 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 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

Grand Designer Home Will Impress Everyone Who E...

Photo of Listing #170344207

$778,000 Deposit

  • 4 Beds
  • 3/1 Baths
  • 5.07 Acres
  • 4,862 ft²

Residential

248 Middlesex Ave, Chester, CT

MLS® #170344207

Grand Designer Home Will Impress Everyone Who Enters With It's Soaring Ceilings, Detailed Millwork, And Sweeping Meadow Views All Tucked Away In A Private Compound. The First Floor Plan Is A Total Open Concept And Includes The Formal Dining Room, Cathedral ...

Berkshire Hathaway NE Prop.

Prominently Set On 2.2 Acres Of Professionally ...

Photo of Listing #170351686

$649,000 Active

  • 3 Beds
  • 2/1 Baths
  • 2.2 Acres
  • 3,802 ft²

Residential

22 Waterhouse Ln, Chester, CT

MLS® #170351686

Prominently Set On 2.2 Acres Of Professionally Landscaped Grounds This Custom Built & Thoughtfully Designed Home With A Spacious Open Floor Plan Allows Interior Spaces To Blend Beautifully With The Natural Surroundings. A Gracious Entrance With Charming Per...

Coldwell Banker Realty

 

©2020 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.