45

Recently Sold Chester, CT Homes

Section Image
  • 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 $821,156

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

    28 Hoop Pole Hill Rd, Chester, CT 06412
  • 15 Hazen St, Chester, CT 06412

    $220,000

    Sold Apr 21, 2026

    15 Hazen St, Chester, CT 06412

    • 3 Beds
    • 1 Bath
    • 748 Sq Ft
    • Built 1900

    Last Sold Summary

    • 10% Above List Price
    • $294/SF
    • 14 Days On Market

    Current Estimated Value $217,610

    Last Listing Agent Anthony La Penna Exceptional Real Estate LLC

    15 Hazen St, 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 $440,797

    Last Listing Agent Ian Sacks Coldwell Banker Realty

    14 Ferry Rd, Chester, CT 06412
  • 16 Sypher Rd, Chester, CT 06412

    $616,000

    Sold Jul 14, 2026

    16 Sypher Rd, Chester, CT 06412

    • 2 Beds
    • 2.5 Baths
    • 1,726 Sq Ft
    • Built 2004

    Last Sold Summary

    • 5% Above List Price
    • $357/SF
    • 42 Days On Market

    Current Estimated Value $602,323

    Last Listing Agent Peg Mitchel Coldwell Banker Realty

    16 Sypher Rd, Chester, CT 06412
  • 42 Straits Rd, Chester, CT 06412

    $460,000

    Sold Aug 21, 2026

    42 Straits Rd, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 2,068 Sq Ft
    • Built 2003

    Last Sold Summary

    • 7% Below List Price
    • $222/SF
    • 6 Days On Market

    Current Estimated Value $498,378

    Last Listing Agent Stephanie Stone William Raveis/First Town RE

    42 Straits 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 $560,917

    Last Listing Agent Craig Milton Re/Max Valley Shore

    7 Hickory Hill Dr, Chester, CT 06412
  • 3 Kirtland Ave, Chester, CT 06412

    $233,600

    Sold Jul 23, 2026

    3 Kirtland Ave, Chester, CT 06412

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2025

    Last Sold Summary

    • 17% Below List Price
    • $174/SF
    • 52 Days On Market

    Current Estimated Value $271,329

    Last Listing Agent Sherry Price Realhome Services & Solutions

    3 Kirtland Ave, Chester, CT 06412
  • 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 $326,843

    Last Listing Agent Craig Milton Re/Max Valley Shore

    12 Deep Hollow Rd, Chester, CT 06412
  • 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 $439,430

    Last Listing Agent Max Gill Puorro Realty Group

    30 Bokum Rd, Chester, CT 06412
  • 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 $830,257

    Last Listing Agent Deborah Rowe William Raveis Real Estate

    14 Maple St, Chester, CT 06412
  • 6 Jagger Ln, Chester, CT 06412

    $805,000

    Sold Sep 01, 2026

    6 Jagger Ln, Chester, CT 06412

    • 2 Beds
    • 2.5 Baths
    • 2,428 Sq Ft
    • Built 1901

    Last Sold Summary

    • $332/SF
    • 89 Days On Market

    Current Estimated Value $787,222

    Last Listing Agent Maddy Mattson Coldwell Banker Realty

    6 Jagger Ln, Chester, CT 06412
  • 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
  • 23 Spring St, Chester, CT 06412

    $550,000

    Sold Oct 15, 2025

    23 Spring St, Chester, CT 06412

    • 2 Beds
    • 1.5 Baths
    • 1,104 Sq Ft
    • Built 1920

    Last Sold Summary

    • 17% Above List Price
    • $498/SF
    • 15 Days On Market

    Current Estimated Value $554,677

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

    23 Spring St, Chester, CT 06412
  • 50 Bokum Rd, Chester, CT 06412

    $375,000

    Sold Nov 13, 2025

    50 Bokum Rd, Chester, CT 06412

    • 2 Beds
    • 1.5 Baths
    • 807 Sq Ft
    • Built 1912

    Last Sold Summary

    • 12% Below List Price
    • $465/SF
    • 59 Days On Market

    Current Estimated Value $382,365

    Last Listing Agent Cynthia Sigurdson William Pitt Sotheby's Int'l

    50 Bokum Rd, Chester, CT 06412
  • 9 Hickory Hill Dr, Chester, CT 06412

    $750,000

    Sold Feb 20, 2026

    9 Hickory Hill Dr, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 2,888 Sq Ft
    • Built 1985

    Last Sold Summary

    • 6% Below List Price
    • $260/SF
    • 101 Days On Market

    Current Estimated Value $771,916

    Last Listing Agent Kathy Schellens William Pitt Sotheby's Int'l

    9 Hickory Hill Dr, Chester, CT 06412
  • 131 Middlesex Ave, Chester, CT 06412

    $530,000

    Sold Feb 26, 2026

    131 Middlesex Ave, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 1,664 Sq Ft
    • Built 1930

    Last Sold Summary

    • 18% Below List Price
    • $319/SF
    • 158 Days On Market

    Current Estimated Value $531,330

    Last Listing Agent Claudia O'Connell William Raveis Real Estate

    131 Middlesex Ave, Chester, CT 06412
  • 81 Main St, Chester, CT 06412

    $618,000

    Sold Jun 11, 2026

    81 Main St, Chester, CT 06412

    • 2 Beds
    • 2 Baths
    • 1,128 Sq Ft
    • Built 1950

    Last Sold Summary

    • 12% Above List Price
    • $548/SF
    • 4 Days On Market

    Current Estimated Value $601,739

    Last Listing Agent Sue Woods William Pitt Sotheby's Int'l

    81 Main St, Chester, CT 06412
  • 21 E Liberty St, Chester, CT 06412

    $252,500

    Sold Nov 17, 2025

    21 E Liberty St, Chester, CT 06412

    • 2 Beds
    • 1 Bath
    • 1,012 Sq Ft
    • Built 1954

    Last Sold Summary

    • 28% Below List Price
    • $250/SF
    • 26 Days On Market

    Current Estimated Value $287,920

    Last Listing Agent Rachel Welch William Raveis Real Estate

    21 E Liberty St, Chester, CT 06412
  • 19 Castle View Dr, Chester, CT 06412

    $470,000

    Sold Jun 12, 2026

    19 Castle View Dr, Chester, CT 06412

    • 3 Beds
    • 1.5 Baths
    • 1,092 Sq Ft
    • Built 1960

    Last Sold Summary

    • 2% Above List Price
    • $430/SF
    • 13 Days On Market

    Current Estimated Value $440,748

    Last Listing Agent Donna Genovese Great Estates, CT

    19 Castle View Dr, Chester, CT 06412
  • 11 Kings Hwy, Chester, CT 06412

    $225,000

    Sold Jun 10, 2026

    11 Kings Hwy, Chester, CT 06412

    • Land
    • 1.5 Acres
    • $150,000 per Acre

    Last Sold Summary

    • 13% Above List Price
    • 1,286 Days On Market

    Last Listing Agent Rachel Welch William Raveis Real Estate

    11 Kings Hwy, Chester, CT 06412
  • 95 Cedar Swamp Rd, Chester, CT 06412

    $1,017,000

    Sold Oct 20, 2025

    95 Cedar Swamp Rd, Chester, CT 06412

    • 4 Beds
    • 3.5 Baths
    • 4,341 Sq Ft
    • Built 1999

    Last Sold Summary

    • $234/SF
    • 53 Days On Market

    Current Estimated Value $1,056,990

    Last Listing Agent Rachel Welch William Raveis Real Estate

    95 Cedar Swamp Rd, Chester, CT 06412
  • 1 Ferry Rd, Chester, CT 06412

    $635,000

    Sold Apr 30, 2026

    1 Ferry Rd, Chester, CT 06412

    • 3 Beds
    • 3 Baths
    • 2,752 Sq Ft
    • Built 1790

    Last Sold Summary

    • 7% Below List Price
    • $231/SF
    • 86 Days On Market

    Current Estimated Value $637,746

    Last Listing Agent Jennifer D'Amato Real Broker CT, LLC

    1 Ferry Rd, Chester, CT 06412
  • 59 Wig Hill Rd, Chester, CT 06412

    $695,000

    Sold Jul 02, 2026

    59 Wig Hill Rd, Chester, CT 06412

    • 5 Beds
    • 2.5 Baths
    • 3,862 Sq Ft
    • Built 1977

    Last Sold Summary

    • 4% Below List Price
    • $180/SF
    • 43 Days On Market

    Current Estimated Value $742,051

    Last Listing Agent Joseph Kelly William Pitt Sotheby's Int'l

    59 Wig Hill Rd, Chester, CT 06412
  • 1 Kirtland Ave, Chester, CT 06412

    $452,000

    Sold Aug 25, 2026

    1 Kirtland Ave, Chester, CT 06412

    • 3 Beds
    • 1.5 Baths
    • 1,198 Sq Ft
    • Built 1968

    Last Sold Summary

    • 3% Above List Price
    • $377/SF
    • 44 Days On Market

    Current Estimated Value $433,443

    Last Listing Agent Craig Milton Re/Max Valley Shore

    1 Kirtland Ave, Chester, CT 06412
  • 7 Old Depot Rd, Chester, CT 06412

    $975,000

    Sold Nov 17, 2025

    7 Old Depot Rd, Chester, CT 06412

    • 4 Beds
    • 2.5 Baths
    • 3,149 Sq Ft
    • Built 1908

    Last Sold Summary

    • 25% Below List Price
    • $310/SF
    • 236 Days On Market

    Current Estimated Value $987,781

    Last Listing Agent Colette Harron William Pitt Sotheby's Int'l

    7 Old Depot Rd, Chester, CT 06412
  • 12 Meadow Ln, Chester, CT 06412

    $515,000

    Sold Jul 27, 2026

    12 Meadow Ln, Chester, CT 06412

    • 3 Beds
    • 3 Baths
    • 2,971 Sq Ft
    • Built 1984

    Last Sold Summary

    • 2% Below List Price
    • $173/SF
    • 31 Days On Market

    Current Estimated Value $519,589

    Last Listing Agent Kelly Puorro Puorro Realty Group

    12 Meadow Ln, Chester, CT 06412
  • 275 W Main St, Chester, CT 06412

    $495,000

    Sold Jun 05, 2026

    275 W Main St, Chester, CT 06412

    • 4 Beds
    • 2 Baths
    • 1,906 Sq Ft
    • Built 1971

    Last Sold Summary

    • 2% Above List Price
    • $260/SF
    • 6 Days On Market

    Current Estimated Value $500,163

    Last Listing Agent Kelly Puorro Puorro Realty Group

    275 W Main St, Chester, CT 06412
  • 22 Goose Hill Rd, Chester, CT 06412

    $500,000

    Sold Sep 02, 2026

    22 Goose Hill Rd, Chester, CT 06412

    • 3 Beds
    • 3 Baths
    • 1,714 Sq Ft
    • Built 1970

    Last Sold Summary

    • 11% Above List Price
    • $292/SF
    • 47 Days On Market

    Current Estimated Value $455,340

    Last Listing Agent Kelly Puorro Puorro Realty Group

    22 Goose Hill Rd, Chester, CT 06412
  • 47 Ferry Rd, Chester, CT 06412

    $1,275,000

    Sold Dec 12, 2025

    47 Ferry Rd, Chester, CT 06412

    • 3 Beds
    • 3 Baths
    • 2,664 Sq Ft
    • Built 1939

    Last Sold Summary

    • 16% Above List Price
    • $479/SF
    • 9 Days On Market

    Current Estimated Value $1,246,861

    Last Listing Agent Mary Poola William Raveis Real Estate

    47 Ferry Rd, Chester, CT 06412
  • 35 Maple St, Chester, CT 06412

    $780,000

    Sold Jan 15, 2026

    35 Maple St, Chester, CT 06412

    • 3 Beds
    • 2 Baths
    • 1,772 Sq Ft
    • Built 1765

    Last Sold Summary

    • 2% Below List Price
    • $440/SF
    • 52 Days On Market

    Current Estimated Value $764,157

    Last Listing Agent Deborah Rowe William Raveis Real Estate

    35 Maple St, Chester, CT 06412
  • 226 Middlesex Ave, Chester, CT 06412

    $695,000

    Sold May 15, 2026

    226 Middlesex Ave, Chester, CT 06412

    • 4 Beds
    • 2.5 Baths
    • 2,029 Sq Ft
    • Built 1976

    Last Sold Summary

    • $343/SF
    • 30 Days On Market

    Current Estimated Value $688,202

    Last Listing Agent Peg Mitchel Coldwell Banker Realty

    226 Middlesex Ave, Chester, CT 06412
  • 6 Pelton Hill Rd, Chester, CT 06412

    $813,500

    Sold Apr 30, 2026

    6 Pelton Hill Rd, Chester, CT 06412

    • 3 Beds
    • 1.5 Baths
    • 1,982 Sq Ft
    • Built 1865

    Last Sold Summary

    • 10% Above List Price
    • $410/SF
    • 23 Days On Market

    Current Estimated Value $782,240

    Last Listing Agent John Zubretsky Century 21 AllPoints Realty

    6 Pelton Hill Rd, Chester, CT 06412
  • 25 Goose Hill Rd, Chester, CT 06412

    $430,000

    Sold Sep 11, 2026

    25 Goose Hill Rd, Chester, CT 06412

    • 2 Beds
    • 1.5 Baths
    • 1,454 Sq Ft
    • Built 1965

    Last Sold Summary

    • 12% Above List Price
    • $296/SF
    • 30 Days On Market

    Current Estimated Value $387,692

    Last Listing Agent Janet Mashia William Pitt Sotheby's Int'l

    25 Goose Hill Rd, Chester, CT 06412
  • 13 Cross Rd, Chester, CT 06412

    $610,000

    Sold Dec 01, 2025

    13 Cross Rd, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 2,324 Sq Ft
    • Built 2005

    Last Sold Summary

    • 6% Below List Price
    • $262/SF
    • 90 Days On Market

    Current Estimated Value $638,189

    Last Listing Agent Curt Clemens Jr. Century 21 Clemens Group

    13 Cross Rd, Chester, CT 06412
  • 36 Kings Hwy, Chester, CT 06412

    $469,900

    Sold Dec 18, 2025

    36 Kings Hwy, Chester, CT 06412

    • 4 Beds
    • 2 Baths
    • 1,516 Sq Ft
    • Built 1930

    Last Sold Summary

    • $310/SF
    • 37 Days On Market

    Current Estimated Value $473,941

    Last Listing Agent Craig Milton Re/Max Valley Shore

    36 Kings Hwy, Chester, CT 06412
  • 8 Butter Jones Rd, Chester, CT 06412

    $715,000

    Sold Mar 06, 2026

    8 Butter Jones Rd, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 2,139 Sq Ft
    • Built 1984

    Last Sold Summary

    • 10% Below List Price
    • $334/SF
    • 175 Days On Market

    Current Estimated Value $704,494

    Last Listing Agent Amy Graham William Pitt Sotheby's Int'l

    8 Butter Jones Rd, Chester, CT 06412
  • 79 Middlesex Ave, Chester, CT 06412

    $410,000

    Sold Apr 30, 2026

    79 Middlesex Ave, Chester, CT 06412

    • 2 Beds
    • 1 Bath
    • 1,470 Sq Ft
    • Built 1952

    Last Sold Summary

    • 22% Below List Price
    • $279/SF
    • 196 Days On Market

    Current Estimated Value $412,075

    Last Listing Agent Gigi Giordano Taylor Compass Connecticut, LLC

    79 Middlesex Ave, Chester, CT 06412
  • 26 Ferry Rd, Chester, CT 06412

    $600,000

    Sold Jul 10, 2026

    26 Ferry Rd, Chester, CT 06412

    • 4 Beds
    • 2 Baths
    • 8,382 Sq Ft
    • Built 1930

    Last Sold Summary

    • 29% Below List Price
    • $72/SF
    • 127 Days On Market

    Last Listing Agent Anthony Velez VC Property Group, LLC

    26 Ferry Rd, Chester, CT 06412
  • 16 Hickory Hill Dr, Chester, CT 06412

    $755,000

    Sold Nov 19, 2025

    16 Hickory Hill Dr, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 1,896 Sq Ft
    • Built 1986

    Last Sold Summary

    • 4% Below List Price
    • $398/SF
    • 48 Days On Market

    Current Estimated Value $751,490

    Last Listing Agent Suzanne McConville William Raveis Real Estate

    16 Hickory Hill Dr, Chester, CT 06412
  • 19 Castle View Dr, Chester, CT 06412

    $214,000

    Sold Feb 04, 2026

    19 Castle View Dr, Chester, CT 06412

    • 3 Beds
    • 1 Bath
    • 1,092 Sq Ft
    • Built 1960

    Last Sold Summary

    • 2% Above List Price
    • $196/SF
    • 15 Days On Market

    Current Estimated Value $440,748

    Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.

    19 Castle View Dr, Chester, CT 06412

Showing Results 1 - 40, Page 1 of 2

Frequently Asked Questions

What is the average home price in Chester, CT?
Homes for sale in Chester, CT have an average home price of $667,543.
What is the average time to sell a house in Chester, CT?
The houses for sale in Chester, CT spend an average of 63 days on the market.
What is the number of active homes for sale in Chester, CT?
There are 9 active homes for sale in Chester, CT.
How many homes have sold over the last 12 months in Chester, CT?
38 homes have sold in Chester, CT over the last 12 months.

Home Price Trends

Median Sale Price
$549,500
Median Single Family Sale Price
$550,000
Median 2 Bedroom Sale Price
$490,000
Median 1 Bedroom Sale Price
$269,900
Average Price Per Sq Ft
$339
Number of Homes for Sale
45
Last 12 months Home Sales
38
Months of Supply
2.80
Median List Price
$550,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
2%
How to Buy a Home How to Finance a Home How to Sell a Home