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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 Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $800,000 - $900,000
$900,000 - $1,000,000

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33 Properties Found. Page 1 of 6

Vermont In Connecticut! This Timeless Gem Boost...

REDUCED 6% Photo of Listing #N10223217

$999,995 Active

  • 4 Beds
  • 5/2 Baths
  • 5.86 Acres
  • 6,350 ft²

Residential

134 Pinnacle Ln, Chester, CT

MLS® #N10223217

Vermont In Connecticut! This Timeless Gem Boosts A Large First Floor Master-suite With Private Terrace And 4 Additional Bedrooms. Situated Nicely On Over 4 Acres - The Home Is A 6200+ Sq Ft Masterpiece Built In 2007 With A Focus On Casual Luxury Living. Fea...

Coldwell Banker Residential Br

Designed For The Ultimate In One Level Living, ...

Open House Photo of Listing #170053745

$995,000 Active

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

Residential

18 East Liberty St, Chester, CT

MLS® #170053745

Designed For The Ultimate In One Level Living, This Superb Home Was Completely Renovated With The Finest Craftsmanship In 2004, All While Restoring And Preserving The Historical Elements. A Bright Open Kitchen, With An Informal Dining Area, Has High Coffere...

Open House Dates & Times

May 20th 12:00 PM - 3:00 PM
William Pitt Sotheby's Int'l

This Stunning 14-acre Gentleman’s Estate Is Bou...

Photo of Listing #170053736

$890,000 Active

  • 4 Beds
  • 4/1 Baths
  • 14.29 Acres
  • 6,200 ft²

Residential

88 Goose Hill Rd, Chester, CT

MLS® #170053736

This Stunning 14-acre Gentleman’s Estate Is Bounded By Stone Walls And Crossed By Intersecting Brooks. Truly A Lifestyle Property Accented By A Long Gradually Ascending Driveway With The 3900 S.f. Home Perched Near The Highest Point And At Exactly The Same ...

William Pitt Sotheby's Int'l

Up A Long Winding Drive, This Exquisitely Lands...

REDUCED 6% Photo of Listing #170058860

$820,000 Active

  • 3 Beds
  • 2/1 Baths
  • 19.07 Acres
  • 3,840 ft²

Residential

67-2,73 Wig Hill Rd, Chester, CT

MLS® #170058860

Up A Long Winding Drive, This Exquisitely Landscaped Property Punctuated By Stone Walls, Terraces, And Specimen Plantings Is A Perfect Private Estate. In Addition To The 2.70 Landscaped Acres, There Is A Separate 16.37 Acre Building Lot That Is Included At ...

William Pitt Sotheby's Int'l

Unlock The Potential Of This Historically Signi...

Photo of Listing #170053208

$676,000 Active

  • 6 Beds
  • 5 Baths
  • 2.28 Acres
  • 2,758 ft²

Residential

9 Story Hill Rd, Chester, CT

MLS® #170053208

Unlock The Potential Of This Historically Significant Chester Treasure To Suit Your Specific Needs. Kitchen And Main Level In-law Suite Renovated In 2014. Would Make A Perfect In-home Office With Private Entrance & Bath. Master Suite Redone In 2008 As Well ...

William Pitt Sotheby's Int'l

Up A Long Winding Drive, This Exquisitely Lands...

REDUCED 7% Photo of Listing #170053000

$660,000 Active

  • 3 Beds
  • 2/1 Baths
  • 2.7 Acres
  • 3,840 ft²

Residential

67-2 Wig Hill Rd, Chester, CT

MLS® #170053000

Up A Long Winding Drive, This Exquisitely Landscaped Property Punctuated By Stone Walls, Terraces, And Specimen Plantings Is A Perfect Private Retreat. The Stunning Architect Designed European Home Offers Wonderful Living Spaces With A Well Appointed Living...

William Pitt Sotheby's Int'l

 

©2018 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.