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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 $600,000 - $700,000
$700,000 - $800,000 $900,000 - $1,000,000

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19 Properties Found. Page 1 of 4

Vermont In Connecticut! This Timeless Gem Boost...

REDUCED 3% Open House Photo of Listing #N10223217

$949,500 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...

Open House Dates & Times

Feb 24th 1:00 PM - 3:00 PM
Coldwell Banker Residential Br

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

Looking For A Home With Room For Everyone.... T...

Photo of Listing #170096296

$695,000 Active

  • 4 Beds
  • 3 Baths
  • 3.86 Acres
  • 2,758 ft²

Residential

9-11 Story Hill Rd, Chester, CT

MLS® #170096296

Looking For A Home With Room For Everyone.... This Is It! This Circa 1860 Stately Country Estate, Rich In History, Sits On 2+ Acres With Sweeping Lawn And Serene Views. This Listing Includes A 1.58 Acre Additional Lot Abutting This Property In This Price. T...

William Pitt Sotheby's Int'l

One Of Chester’s Finest Homes Is Majestically S...

Photo of Listing #170140350

$694,500 Active

  • 4 Beds
  • 4/1 Baths
  • 1.01 Acres
  • 4,051 ft²

Residential

25 Gilbert Hill Rd, Chester, CT

MLS® #170140350

One Of Chester’s Finest Homes Is Majestically Sited With Striking Views Of The Ct River, The Hills Of Lyme And Expansive Valley Views. An Absolutely Immaculate Home Along With Meticulously Manicured Grounds Of Lush Lawns And Gardens Favor A Peaceful Feeling...

William Pitt Sotheby's Int'l

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

NEW Photo of Listing #170164589

$619,000 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 To 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 B...

William Raveis Real Estate

'the Bow House' Is A Captivating Waterfront Dre...

REDUCED 14% Photo of Listing #170134601

$599,000 Show

  • 3 Beds
  • 4/1 Baths
  • 0.91 Acres
  • 3,031 ft²

Residential

16 Spring St, Chester, CT

MLS® #170134601

'the Bow House' Is A Captivating Waterfront Dream House Set Steps From Bustling Chester Village, Yet A World Apart! Perched Just Above Jennings Pond, You Will Enjoy Views Of The Pond, Waterfall And Your Dock; From Which You Can Launch Your Kayak, Canoe Or S...

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.