1,679

Chester, CT Homes

Section Image Section Image
  • 26 Ferry Rd, Chester, CT 06412
    26 Ferry Rd, Chester, CT 06412
    26 Ferry Rd, Chester, CT 06412
    /21

    $850,000

    • 4 Beds
    • 2 Baths
    • 8,382 Sq Ft

    26 Ferry Rd, Chester, CT 06412

    Located in the Town of Chester, this mixed-use property presents a rare opportunity to acquire a distinctive asset in one of Connecticut's most desirable markets. As it stands, the property consists of approximately 5,000 square feet of commercial space, including one loading dock, three (3) garages, and an oversized on-site parking lot, supporting a wide range of operational and occupancy needs.

    Agent Photo

    Anthony Velez

    VC Property Group, LLC

    (860) 579-1600

    26 Ferry Rd, Chester, CT 06412
  • 15 Liberty St, Chester, CT 06412
    15 Liberty St, Chester, CT 06412
    15 Liberty St, Chester, CT 06412
    /39

    $7,500 total monthly price

    • 4 Beds
    • 4.5 Baths
    • 4,708 Sq Ft
    • House for Rent

    15 Liberty St, Chester, CT 06412

    Exceptional Rental Opportunity in Chester's Quintessential New England Village. Experience refined living in this estate-like setting, exquisitely furnished and thoughtfully remodeled to the highest standards. Offering over 4,000 sq. ft. of light-filled luxury, this stunning home is available October 2025 through mid-May 2026. Property Highlights: 4 Bedrooms | 5 Baths - including an exceptionally

    Lynn Lehrman Re/Max Valley Shore

    15 Liberty St, Chester, CT 06412
  • 15 Gilbert Hill Rd, Chester, CT 06412

    $1,000,050 Sold Jun 25, 2025

    15 Gilbert Hill Rd, Chester, CT 06412

    • 4 Beds
    • 3 Baths
    • 3,054 Sq Ft
    • Built 1950

    Last Sold Summary

    • 22% Above List Price
    • $327/SF
    • 18 Days On Market

    Current Estimated Value $983,646

    Last Listing Agent Angela Ruel Berkshire Hathaway NE Prop.

    15 Gilbert Hill Rd, Chester, CT 06412
    • 10 Old County Rd, Chester, CT 06412

      Est $929,719 Not Listed For Sale

      10 Old County Rd, Chester, CT 06412

      • 4 Beds
      • 3.5 Baths
      • 2,755 Sq Ft
      • Built 1998
      10 Old County Rd, Chester, CT 06412

      Last Sold Summary

      • 3% Above List Price
      • $327/SF
      • 26 Days On Market

      Last Sold Price $900,000

      Last Listing Agent Susan Malan William Pitt

  • 1 Ferry Rd, Chester, CT 06412
    1 Ferry Rd, Chester, CT 06412
    1 Ferry Rd, Chester, CT 06412
    /40

    $650,000

    • 3 Beds
    • 3 Baths
    • 2,752 Sq Ft

    1 Ferry Rd, Chester, CT 06412

    An extraordinary offering in one of Connecticut's most beloved river towns. Stunning sunrises over unobstructed views of Chester Creek sets the tone for this rare piece of Chester history. The Bani Denison homestead dates to 1781 and once served as Chester's first post office. Thoughtfully restored, this classic embankment Colonial with Dutch kick gambrel style roof offers modern amenities while

    Agent Photo

    Jennifer D'Amato

    Real Broker CT, LLC

    (860) 454-6525

    1 Ferry Rd, Chester, CT 06412
  • 28 Hoop Pole Hill Rd, Chester, CT 06412

    $760,000 Sold Nov 03, 2025

    28 Hoop Pole Hill Rd, Chester, CT 06412

    • 4 Beds
    • 3.5 Baths
    • 3,396 Sq Ft
    • Built 2008

    Last Sold Summary

    • 5% Below List Price
    • $224/SF
    • 83 Days On Market

    Current Estimated Value $798,648

    Last Listing Agent Teri Lewis William Pitt Sotheby's Int'l

    28 Hoop Pole Hill Rd, Chester, CT 06412
    • 71 Maple St, Chester, CT 06412

      Est $594,694 Not Listed For Sale

      71 Maple St, Chester, CT 06412

      • 2 Beds
      • 1.5 Baths
      • 2,144 Sq Ft
      • Built 1980
      71 Maple St, Chester, CT 06412

      Last Sold Summary

      • 10% Above List Price
      • $252/SF
      • 172 Days On Market

      Last Sold Price $540,000

      Last Listing Agent Louisa Ketron Berkshire Hathaway Home Services

  • 43 Bokum Rd, Chester, CT 06412
    43 Bokum Rd, Chester, CT 06412
    /2

    $200,000

    • Land
    • 2.25 Acres
    • $88,889 per Acre

    43 Bokum Rd, Chester, CT 06412

    Beautiful potential building lot. Access via Private road, 2.25 acres. Undeveloped.

    Nicholas Tomanelli Coldwell Banker Realty

    43 Bokum Rd, Chester, CT 06412
  • 14 Ferry Rd, Chester, CT 06412

    $420,000 Sold Sep 24, 2025

    14 Ferry Rd, Chester, CT 06412

    • 4 Beds
    • 1.5 Baths
    • 2,025 Sq Ft
    • Built 1950

    Last Sold Summary

    • 5% Above List Price
    • $207/SF
    • 35 Days On Market

    Current Estimated Value $408,946

    Last Listing Agent Ian Sacks Coldwell Banker Realty

    14 Ferry Rd, Chester, CT 06412
    • 75 Pinnacle Ln, Chester, CT 06412

      Est $930,783 Not Listed For Sale

      75 Pinnacle Ln, Chester, CT 06412

      • 4 Beds
      • 3 Baths
      • 3,033 Sq Ft
      • Built 2006
      75 Pinnacle Ln, Chester, CT 06412

      Last Sold Summary

      • 13% Above List Price
      • $272/SF
      • 20 Days On Market

      Last Sold Price $825,000

      Last Listing Agent Kristen Butts Century 21 Clemens Group

  • 15 Hazen St, Chester, CT 06412
    15 Hazen St, Chester, CT 06412
    15 Hazen St, Chester, CT 06412
    /33

    $199,900 Pending

    • 3 Beds
    • 1 Bath
    • 748 Sq Ft

    15 Hazen St, Chester, CT 06412

    **FINAL AND BEST OFFERS DUE BY WEDNESDAY 3/4/26 BY 5PM** Fantastic condo alternative with year-round charm and lake lifestyle appeal! Enjoy scenic views of Cedar Lake and take advantage of the easy walk to nearby beaches from this inviting 4-season cottage. Situated on a large corner lot framed by classic New England stone walls, this property offers privacy, character, and outdoor enjoyment.

    Anthony La Penna Exceptional Real Estate LLC

    15 Hazen St, Chester, CT 06412
  • 93 W Main St, Chester, CT 06412

    $180,000 Sold May 09, 2025

    93 W Main St, Chester, CT 06412

    • 1 Bed
    • 1 Bath
    • 752 Sq Ft
    • Built 1955

    Last Sold Summary

    • 5% Below List Price
    • $239/SF
    • 32 Days On Market

    Current Estimated Value $193,296

    Last Listing Agent Kelly Puorro Puorro Realty Group

    93 W Main St, Chester, CT 06412
    • 22 Hickory Hill Dr, Chester, CT 06412

      Est $549,731 Not Listed For Sale

      22 Hickory Hill Dr, Chester, CT 06412

      • 3 Beds
      • 2.5 Baths
      • 1,838 Sq Ft
      • Built 1985
      22 Hickory Hill Dr, Chester, CT 06412

      Last Sold Summary

      • 29% Above List Price
      • $232/SF
      • 49 Days On Market

      Last Sold Price $426,250

      Last Listing Agent John Oliveri Property Works New England

  • 11 Kings Hwy, Chester, CT 06412
    11 Kings Hwy, Chester, CT 06412
    11 Kings Hwy, Chester, CT 06412
    /11

    $238,500

    • Land
    • 1.5 Acres
    • $159,000 per Acre

    11 Kings Hwy, Chester, CT 06412

    1.5+ acre lot, clear cut, open, sunny, with a clean air flow. SE facing with 4-mile view down CT River Valley to Deep River, and Lyme Hills; seasonal partial view of Gillette Castle in Hadlyme. Excellent solar, passive or active potential; 220 volts available at street. Ready to build with approvals in place for 3-bedroom septic, town building department, with Connecticut Water Co. supply line

    Rachel Welch William Raveis Real Estate

    11 Kings Hwy, Chester, CT 06412
  • 6 Old County Rd, Chester, CT 06412

    $975,000 Sold Apr 30, 2025

    6 Old County Rd, Chester, CT 06412

    • 4 Beds
    • 2.5 Baths
    • 2,680 Sq Ft
    • Built 2002

    Last Sold Summary

    • 12% Above List Price
    • $364/SF
    • 5 Days On Market

    Current Estimated Value $995,093

    Last Listing Agent Susan Malan William Pitt Sotheby's Int'l

    6 Old County Rd, Chester, CT 06412
    • 8 Winthrop Rd, Chester, CT 06412

      Est $420,579 Not Listed For Sale

      8 Winthrop Rd, Chester, CT 06412

      • 3 Beds
      • 1.5 Baths
      • 1,344 Sq Ft
      • Built 1953
      8 Winthrop Rd, Chester, CT 06412

      Last Sold Summary

      • 34% Above List Price
      • $234/SF
      • 12 Days On Market

      Last Sold Price $315,000

      Last Listing Agent Carly Luciér Our Home Realty Advisors

  • 6 Pelton Hill Rd, Chester, CT 06412
    6 Pelton Hill Rd, Chester, CT 06412
    6 Pelton Hill Rd, Chester, CT 06412
    /40

    $738,500 Under Contract

    • 3 Beds
    • 1.5 Baths
    • 1,982 Sq Ft

    6 Pelton Hill Rd, Chester, CT 06412

    Nestled at the end of a peaceful, dead-end street, this beautifully maintained Carpenter Gothic home offers the perfect blend of historic charm and modern comforts. With its unique architectural style and serene private setting, this property is truly a hidden gem. The three Bedrooms are spacious and bright, each bedroom offers a cozy retreat with plenty of natural light and charming details that

    John Zubretsky Century 21 AllPoints Realty

    6 Pelton Hill Rd, Chester, CT 06412
  • 7 Hickory Hill Dr, Chester, CT 06412

    $549,000 Sold Mar 24, 2026

    7 Hickory Hill Dr, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 2,202 Sq Ft
    • Built 1984

    Last Sold Summary

    • $249/SF
    • 6 Days On Market

    Current Estimated Value $565,929

    Last Listing Agent Craig Milton Re/Max Valley Shore

    7 Hickory Hill Dr, Chester, CT 06412
    • 41 Railroad Ave, Chester, CT 06412

      Est $445,202 Not Listed For Sale

      41 Railroad Ave, Chester, CT 06412

      • 2 Beds
      • 1 Bath
      • 1,771 Sq Ft
      • Built 1952
      41 Railroad Ave, Chester, CT 06412

      Last Sold Summary

      • 14% Above List Price
      • $220/SF
      • 46 Days On Market

      Last Sold Price $390,000

      Last Listing Agent Philip Warner William Pitt

  • 79 Middlesex Ave, Chester, CT 06412
    79 Middlesex Ave, Chester, CT 06412
    79 Middlesex Ave, Chester, CT 06412
    /32

    $425,000

    • 2 Beds
    • 1 Bath
    • 1,470 Sq Ft

    79 Middlesex Ave, Chester, CT 06412

    Charming Cape just steps from Chester Village! This inviting 2-bed, 1-bath home blends timeless New England character with everyday comfort and walk-to-village convenience. Warm newly refinished hardwood floors flow throughout the light-filled living room into the updated kitchen with its beautiful bow window and dining area. The kitchen is replete with ample granite counters, perfect for the

    Gigi Giordano Taylor Compass Connecticut, LLC

    79 Middlesex Ave, Chester, CT 06412
  • 16 Waterhouse Ln, Chester, CT 06412

    $1,250,000 Sold May 02, 2025

    16 Waterhouse Ln, Chester, CT 06412

    • 4 Beds
    • 4.5 Baths
    • 4,661 Sq Ft
    • Built 1988

    Last Sold Summary

    • $268/SF
    • 24 Days On Market

    Current Estimated Value $1,285,295

    Last Listing Agent Teri Lewis William Pitt Sotheby's Int'l

    16 Waterhouse Ln, Chester, CT 06412
    • 248 Middlesex Ave, Chester, CT 06412

      Est $1,134,760 Not Listed For Sale

      248 Middlesex Ave, Chester, CT 06412

      • 4 Beds
      • 3.5 Baths
      • 4,862 Sq Ft
      • Built 2007
      248 Middlesex Ave, Chester, CT 06412

      Last Sold Summary

      • 11% Above List Price
      • $211/SF
      • 21 Days On Market

      Last Sold Price $1,025,000

      Last Listing Agent Tammy Tinnerello William Pitt

  • 25 Spring St, Chester, CT 06412

    $860,000 Sold Sep 17, 2025

    25 Spring St, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 2,344 Sq Ft
    • Built 1860

    Last Sold Summary

    • 4% Below List Price
    • $367/SF
    • 38 Days On Market

    Current Estimated Value $849,614

    Last Listing Agent Susan Malan William Pitt Sotheby's Int'l

    25 Spring St, Chester, CT 06412
    • 37 Castle View Dr, Chester, CT 06412

      Est $450,436 Not Listed For Sale

      37 Castle View Dr, Chester, CT 06412

      • 3 Beds
      • 2.5 Baths
      • 1,820 Sq Ft
      • Built 1972
      37 Castle View Dr, Chester, CT 06412

      Last Sold Summary

      • 5% Above List Price
      • $236/SF
      • 21 Days On Market

      Last Sold Price $429,900

      Last Listing Agent Nancy Bullis Coldwell Banker Realty

  • 12 Deep Hollow Rd, Chester, CT 06412

    $319,900 Sold Jan 20, 2026

    12 Deep Hollow Rd, Chester, CT 06412

    • 3 Beds
    • 1 Bath
    • 912 Sq Ft
    • Built 1960

    Last Sold Summary

    • $351/SF
    • 52 Days On Market

    Current Estimated Value $316,053

    Last Listing Agent Craig Milton Re/Max Valley Shore

    12 Deep Hollow Rd, Chester, CT 06412
    • 25 Deep Hollow Rd, Chester, CT 06412

      Est $566,982 Not Listed For Sale

      25 Deep Hollow Rd, Chester, CT 06412

      • 3 Beds
      • 2.5 Baths
      • 1,710 Sq Ft
      • Built 1993
      25 Deep Hollow Rd, Chester, CT 06412

      Last Sold Summary

      • 8% Above List Price
      • $307/SF
      • 18 Days On Market

      Last Sold Price $525,000

      Last Listing Agent Craig Milton RE/MAX

  • 30 Bokum Rd, Chester, CT 06412

    $442,500 Sold Oct 20, 2025

    30 Bokum Rd, Chester, CT 06412

    • 3 Beds
    • 2 Baths
    • 1,198 Sq Ft
    • Built 1930

    Last Sold Summary

    • 4% Above List Price
    • $369/SF
    • 59 Days On Market

    Current Estimated Value $434,094

    Last Listing Agent Max Gill Puorro Realty Group

    30 Bokum Rd, Chester, CT 06412
    • 16 Ridge Rd, Chester, CT 06412

      Est $627,961 Not Listed For Sale

      16 Ridge Rd, Chester, CT 06412

      • 4 Beds
      • 2.5 Baths
      • 2,722 Sq Ft
      • Built 1928
      16 Ridge Rd, Chester, CT 06412

      Last Sold Summary

      • 13% Above List Price
      • $204/SF
      • 38 Days On Market

      Last Sold Price $555,000

      Last Listing Agent Linda Conchado Century 21 AllPoints Realty

  • 80 W Main St, Chester, CT 06412

    $795,000 Sold Jul 31, 2025

    80 W Main St, Chester, CT 06412

    • 3 Beds
    • 2 Baths
    • 2,389 Sq Ft
    • Built 1835

    Last Sold Summary

    • 14% Above List Price
    • $333/SF
    • 3 Days On Market

    Current Estimated Value $777,878

    Last Listing Agent Mary Jean Agostini RE/MAX Right Choice

    80 W Main St, Chester, CT 06412
    • 12 Liberty St, Chester, CT 06412

      Est $705,238 Not Listed For Sale

      12 Liberty St, Chester, CT 06412

      • 3 Beds
      • 2.5 Baths
      • 2,713 Sq Ft
      • Built 1925
      12 Liberty St, Chester, CT 06412

      Last Sold Summary

      • 1% Below List Price
      • $264/SF
      • 3 Days On Market

      Last Sold Price $715,000

      Last Listing Agent Rick Weiner William Pitt

  • 14 Maple St, Chester, CT 06412

    $810,000 Sold Nov 14, 2025

    14 Maple St, Chester, CT 06412

    • 3 Beds
    • 3.5 Baths
    • 2,322 Sq Ft
    • Built 1755

    Last Sold Summary

    • 1% Above List Price
    • $349/SF
    • 6 Days On Market

    Current Estimated Value $797,863

    Last Listing Agent Deborah Rowe William Raveis Real Estate

    14 Maple St, Chester, CT 06412
    • 230 W Main St, Chester, CT 06412

      Est $427,328 Not Listed For Sale

      230 W Main St, Chester, CT 06412

      • 2 Beds
      • 1.5 Baths
      • 1,530 Sq Ft
      • Built 1986
      230 W Main St, Chester, CT 06412

      Last Sold Summary

      • 6% Above List Price
      • $265/SF
      • 24 Days On Market

      Last Sold Price $405,000

      Last Listing Agent Siobhan McLaughlin William Raveis Real Estate

  • 69 Spring St, Chester, CT 06412

    $715,000 Sold Jul 25, 2025

    69 Spring St, Chester, CT 06412

    • 3 Beds
    • 1.5 Baths
    • 1,702 Sq Ft
    • Built 1883

    Last Sold Summary

    • 10% Above List Price
    • $420/SF
    • 30 Days On Market

    Current Estimated Value $684,125

    Last Listing Agent Rachel Welch William Raveis Real Estate

    69 Spring St, Chester, CT 06412
    • 7 Pine Knoll Dr, Chester, CT 06412

      Est $665,466 Not Listed For Sale

      7 Pine Knoll Dr, Chester, CT 06412

      • 3 Beds
      • 2.5 Baths
      • 2,607 Sq Ft
      • Built 2002
      7 Pine Knoll Dr, Chester, CT 06412

      Last Sold Summary

      • 15% Above List Price
      • $222/SF
      • 4 Days On Market

      Last Sold Price $580,000

      Last Listing Agent Jamie Franco Coldwell Banker

  • 19 W Main St, Chester, CT 06412

    $1,363,500 Sold Apr 15, 2025

    19 W Main St, Chester, CT 06412

    • 4 Beds
    • 3.5 Baths
    • 4,205 Sq Ft
    • Built 1999

    Last Sold Summary

    • 9% Below List Price
    • $324/SF
    • 136 Days On Market

    Last Listing Agent Michael Marsden Compass Connecticut, LLC

    19 W Main St, Chester, CT 06412
    • 22 Waterhouse Ln, Chester, CT 06412

      Est $927,235 Not Listed For Sale

      22 Waterhouse Ln, Chester, CT 06412

      • 3 Beds
      • 2.5 Baths
      • 3,802 Sq Ft
      • Built 1999
      22 Waterhouse Ln, Chester, CT 06412

      Last Sold Summary

      • 31% Above List Price
      • $187/SF
      • 69 Days On Market

      Last Sold Price $710,000

      Last Listing Agent Craig Milton RE/MAX

  • 24 E Liberty St, Chester, CT 06412

    $450,000 Sold May 14, 2025

    24 E Liberty St, Chester, CT 06412

    • 4 Beds
    • 2 Baths
    • 1,926 Sq Ft
    • Built 1790

    Last Sold Summary

    • 7% Above List Price
    • $234/SF
    • 13 Days On Market

    Current Estimated Value $485,495

    Last Listing Agent Bonnie Fillion Berkshire Hathaway NE Prop.

    24 E Liberty St, Chester, CT 06412
    • 19 Hickory Hill Dr, Chester, CT 06412

      Est $789,101 Not Listed For Sale

      19 Hickory Hill Dr, Chester, CT 06412

      • 3 Beds
      • 3 Baths
      • 2,646 Sq Ft
      • Built 1984
      19 Hickory Hill Dr, Chester, CT 06412

      Last Sold Summary

      • 17% Above List Price
      • $255/SF
      • 5 Days On Market

      Last Sold Price $675,000

      Last Listing Agent Mark Capsalors Select Realty Associates, LLC

  • 28 S Wig Hill Rd, Chester, CT 06412

    $580,000 Sold Dec 10, 2025

    28 S Wig Hill Rd, Chester, CT 06412

    • 2 Beds
    • 3 Baths
    • 3,091 Sq Ft
    • Built 1770

    Last Sold Summary

    • 10% Below List Price
    • $188/SF
    • 138 Days On Market

    Last Listing Agent Andrew O'Reilly Seaport Real Estate Services

    28 S Wig Hill Rd, Chester, CT 06412
    • 2 Sypher Rd, Chester, CT 06412

      Est $523,203 Not Listed For Sale

      2 Sypher Rd, Chester, CT 06412

      • 4 Beds
      • 2.5 Baths
      • 2,278 Sq Ft
      • Built 1970
      2 Sypher Rd, Chester, CT 06412

      Last Sold Summary

      • 16% Above List Price
      • $198/SF
      • 66 Days On Market

      Last Sold Price $450,000

      Last Listing Agent Stacey Wyeth William Pitt

Showing Results 1 - 40, Page 1 of 18

Connecticut Middlesex County Chester

Real Estate & Homes

Home Trends in Chester, CT

On average, homes in Chester, CT sell after 57 days on the market compared to the national average of 55 days. The median sale price for homes in Chester, CT over the last 12 months is $651,500, up 40% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$651,500
Median Single Family Sale Price
$650,000
Average Price Per Sq Ft
$331
Number of Homes for Sale
2
Last 12 months Home Sales
43
Months of Supply
0.60
Median List Price
$649,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
40%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group