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Recently Sold Chester, CT Homes

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  • 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 $984,414

    Last Listing Agent Angela Ruel Berkshire Hathaway NE Prop.

    15 Gilbert Hill 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

    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

    $540,000 Sold Mar 20, 2025

    71 Maple St, Chester, CT 06412

    • 2 Beds
    • 1.5 Baths
    • 2,144 Sq Ft
    • Built 1980

    Last Sold Summary

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

    Current Estimated Value $580,536

    Last Listing Agent Louisa Ketron Berkshire Hathaway NE Prop.

    71 Maple 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

    Last Listing Agent Ian Sacks Coldwell Banker Realty

    14 Ferry Rd, 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 $192,229

    Last Listing Agent Kelly Puorro Puorro Realty Group

    93 W Main St, 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 $973,672

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

    6 Old County Rd, Chester, CT 06412
  • 15 Kirtland Terrace, Chester, CT 06412

    $280,000 Sold Mar 07, 2025

    15 Kirtland Terrace, Chester, CT 06412

    • 3 Beds
    • 1.5 Baths
    • 1,170 Sq Ft
    • Built 1951

    Last Sold Summary

    • 24% Above List Price
    • $239/SF
    • 3 Days On Market

    Current Estimated Value $246,406

    Last Listing Agent Kristina Quinones William Pitt Sotheby's Int'l

    15 Kirtland Terrace, 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 $1,276,643

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

    16 Waterhouse Ln, Chester, CT 06412
  • 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 $864,178

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

    25 Spring St, 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

    Last Listing Agent Max Gill Puorro Realty Group

    30 Bokum Rd, Chester, CT 06412
  • 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 $778,230

    Last Listing Agent Mary Jean Agostini RE/MAX Right Choice

    80 W Main St, 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

    Last Listing Agent Deborah Rowe William Raveis Real Estate

    14 Maple St, Chester, CT 06412
  • 2 Sypher Rd, Chester, CT 06412

    $450,000 Sold Jan 24, 2025

    2 Sypher Rd, Chester, CT 06412

    • 4 Beds
    • 2.5 Baths
    • 2,278 Sq Ft
    • Built 1970

    Last Sold Summary

    • 2% Below List Price
    • $198/SF
    • 66 Days On Market

    Current Estimated Value $496,789

    Last Listing Agent Stacey Wyeth William Pitt Sotheby's Int'l

    2 Sypher Rd, Chester, CT 06412
  • 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 $684,916

    Last Listing Agent Rachel Welch William Raveis Real Estate

    69 Spring St, Chester, CT 06412
  • 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
  • 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 $475,659

    Last Listing Agent Bonnie Fillion Berkshire Hathaway NE Prop.

    24 E Liberty St, 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

    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

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

    50 Bokum Rd, Chester, CT 06412
  • 32 Gilbert Hill Rd, Chester, CT 06412

    $952,397 Sold Jul 10, 2025

    32 Gilbert Hill Rd, Chester, CT 06412

    • 3 Beds
    • 3 Baths
    • 3,788 Sq Ft
    • Built 1986

    Last Sold Summary

    • 17% Below List Price
    • $251/SF
    • 70 Days On Market

    Current Estimated Value $963,205

    Last Listing Agent Steve Q Exclusive Properties

    32 Gilbert Hill Rd, Chester, CT 06412
  • 31 Parkers Point Rd, Chester, CT 06412

    $3,100,000 Sold Jun 10, 2025

    31 Parkers Point Rd, Chester, CT 06412

    • 3 Beds
    • 3.5 Baths
    • 4,727 Sq Ft
    • Built 2010

    Last Sold Summary

    • 11% Below List Price
    • $656/SF
    • 27 Days On Market

    Current Estimated Value $3,301,919

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

    31 Parkers Point Rd, Chester, CT 06412
  • 67 W Main St, Chester, CT 06412

    $637,500 Sold Jan 31, 2025

    67 W Main St, Chester, CT 06412

    • 3 Beds
    • 1.5 Baths
    • 1,916 Sq Ft
    • Built 1917

    Last Sold Summary

    • $333/SF
    • 8 Days On Market

    Current Estimated Value $675,370

    Last Listing Agent Kyle Hinding Coldwell Banker Realty

    67 W Main St, Chester, CT 06412
  • 5 Marina View Dr, Chester, CT 06412

    $500,000 Sold Jan 17, 2025

    5 Marina View Dr, Chester, CT 06412

    • 3 Beds
    • 3.5 Baths
    • 2,037 Sq Ft
    • Built 1993

    Last Sold Summary

    • 17% Below List Price
    • $245/SF
    • 81 Days On Market

    Current Estimated Value $553,717

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

    5 Marina View Dr, Chester, CT 06412
  • 79 Cedar Lake Rd, Chester, CT 06412

    $875,000 Sold Jul 25, 2025

    79 Cedar Lake Rd, Chester, CT 06412

    • 4 Beds
    • 3 Baths
    • 3,206 Sq Ft
    • Built 2004

    Last Sold Summary

    • 8% Below List Price
    • $273/SF
    • 83 Days On Market

    Current Estimated Value $870,717

    Last Listing Agent Bill Heenan William Raveis Real Estate

    79 Cedar Lake Rd, 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

    Last Listing Agent Rachel Welch William Raveis Real Estate

    21 E Liberty St, 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

    Last Listing Agent Rachel Welch William Raveis Real Estate

    95 Cedar Swamp Rd, Chester, CT 06412
  • 14 Straits Rd, Chester, CT 06412

    $285,000 Sold Apr 09, 2025

    14 Straits Rd, Chester, CT 06412

    • 3 Beds
    • 1 Bath
    • 1,519 Sq Ft
    • Built 1702

    Last Sold Summary

    • 5% Below List Price
    • $188/SF
    • 4 Days On Market

    Current Estimated Value $294,552

    Last Listing Agent Kelly Puorro Puorro Realty Group

    14 Straits Rd, Chester, CT 06412
  • 67 Maple St, Chester, CT 06412

    $575,000 Sold May 29, 2025

    67 Maple St, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 1,803 Sq Ft
    • Built 2005

    Last Sold Summary

    • 10% Above List Price
    • $319/SF
    • 44 Days On Market

    Current Estimated Value $585,364

    Last Listing Agent Laura Cariati William Raveis Real Estate

    67 Maple St, 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

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

    7 Old Depot Rd, Chester, CT 06412
  • 11 Bishop Rd, Chester, CT 06412

    $350,000 Sold Apr 07, 2025

    11 Bishop Rd, Chester, CT 06412

    • 3 Beds
    • 1.5 Baths
    • 1,188 Sq Ft
    • Built 1964

    Last Sold Summary

    • $295/SF
    • 6 Days On Market

    Current Estimated Value $367,097

    Last Listing Agent Craig Milton Re/Max Valley Shore

    11 Bishop 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

    Last Listing Agent Mary Poola William Raveis Real Estate

    47 Ferry Rd, Chester, CT 06412
  • 10 Old County Rd, Chester, CT 06412

    $900,000 Sold Mar 24, 2025

    10 Old County Rd, Chester, CT 06412

    • 4 Beds
    • 3.5 Baths
    • 2,755 Sq Ft
    • Built 1998

    Last Sold Summary

    • 7% Above List Price
    • $327/SF
    • 26 Days On Market

    Current Estimated Value $903,365

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

    10 Old County Rd, Chester, CT 06412
  • 108 Middlesex Ave, Chester, CT 06412

    $675,000 Sold May 01, 2025

    108 Middlesex Ave, Chester, CT 06412

    • 4 Beds
    • 4.5 Baths
    • 4,056 Sq Ft
    • Built 2002

    Last Sold Summary

    • 3% Below List Price
    • $166/SF
    • 65 Days On Market

    Current Estimated Value $697,541

    Last Listing Agent Trever Smith Chiarito Real Estate LLC

    108 Middlesex Ave, Chester, CT 06412
  • 96 Middlesex Ave, Chester, CT 06412

    $1,300,000 Sold Jan 31, 2025

    96 Middlesex Ave, Chester, CT 06412

    • 4 Beds
    • 3.5 Baths
    • 3,153 Sq Ft
    • Built 1830

    Last Sold Summary

    • 7% Below List Price
    • $412/SF
    • 162 Days On Market

    Current Estimated Value $1,331,173

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

    96 Middlesex Ave, Chester, CT 06412
  • 261 Middlesex Ave, Chester, CT 06412

    $360,000 Sold Feb 25, 2025

    261 Middlesex Ave, Chester, CT 06412

    • 3 Beds
    • 1 Bath
    • 1,248 Sq Ft
    • Built 1935

    Last Sold Summary

    • 13% Above List Price
    • $288/SF
    • 36 Days On Market

    Current Estimated Value $376,965

    Last Listing Agent Theresa Bitondo Berkshire Hathaway NE Prop.

    261 Middlesex Ave, 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

    Last Listing Agent Curtiss 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

    Last Listing Agent Craig Milton Re/Max Valley Shore

    36 Kings Hwy, Chester, CT 06412
  • 39 Castle View Dr, Chester, CT 06412

    $419,900 Sold Jan 07, 2025

    39 Castle View Dr, Chester, CT 06412

    • 3 Beds
    • 3.5 Baths
    • 2,208 Sq Ft
    • Built 2013

    Last Sold Summary

    • $190/SF
    • 95 Days On Market

    Current Estimated Value $468,615

    Last Listing Agent Gene Pica RE/MAX Alliance

    39 Castle View Dr, Chester, CT 06412
  • 42 W Main St, Chester, CT 06412

    $651,500 Sold May 16, 2025

    42 W Main St, Chester, CT 06412

    • 4 Beds
    • 2 Baths
    • 1,766 Sq Ft
    • Built 1925

    Last Sold Summary

    • $369/SF
    • 35 Days On Market

    Current Estimated Value $647,137

    Last Listing Agent Pardi & Zucco Team William Pitt Sotheby's Int'l

    42 W Main St, Chester, CT 06412
  • 25 Gilbert Hill Rd, Chester, CT 06412

    $1,135,000 Sold Jun 30, 2025

    25 Gilbert Hill Rd, Chester, CT 06412

    • 4 Beds
    • 4.5 Baths
    • 3,351 Sq Ft
    • Built 1987

    Last Sold Summary

    • 3% Above List Price
    • $339/SF
    • 16 Days On Market

    Current Estimated Value $1,132,770

    Last Listing Agent Robin Linares William Pitt Sotheby's Int'l

    25 Gilbert Hill Rd, 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 $779,676.
What is the average time to sell a house in Chester, CT?
The houses for sale in Chester, CT spend an average of 54 days on the market.
What is the number of active homes for sale in Chester, CT?
There are 6 active homes for sale in Chester, CT.
How many homes have sold over the last 12 months in Chester, CT?
45 homes have sold in Chester, CT over the last 12 months.

Home Trends in Chester, CT

Housing Trends

Median Sale Price
$610,000
Median Single Family Sale Price
$610,000
Average Price Per Sq Ft
$334
Number of Homes for Sale
6
Last 12 months Home Sales
45
Months of Supply
1.60
Median List Price
$649,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
46%
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