45

Recently Sold Chester, CT Homes

Section Image
  • 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 $1,008,711

    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

    Current Estimated Value $792,640

    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 $221,489

    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 $433,384

    Last Listing Agent Ian Sacks Coldwell Banker Realty

    14 Ferry 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 $555,432

    Last Listing Agent Craig Milton Re/Max Valley Shore

    7 Hickory Hill Dr, 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 $839,641

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

    25 Spring St, 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 $326,405

    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 $441,973

    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 $801,669

    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

    Current Estimated Value $825,576

    Last Listing Agent Deborah Rowe William Raveis Real Estate

    14 Maple St, 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 $718,000

    Last Listing Agent Rachel Welch William Raveis Real Estate

    69 Spring 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

    Current Estimated Value $558,614

    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 $377,762

    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 $998,799

    Last Listing Agent Steve Q Exclusive Properties

    32 Gilbert Hill 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 $758,428

    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 $536,643

    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 $441,074

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

    81 Main St, 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 $895,237

    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

    Current Estimated Value $284,839

    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 $226,606

    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 $1,049,338

    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 $648,689

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

    1 Ferry Rd, 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 $982,305

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

    7 Old Depot Rd, 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 $563,324

    Last Listing Agent Kelly Puorro Puorro Realty Group

    275 W Main St, 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 $1,256,108

    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 $786,000

    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 $677,262

    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 $745,320

    Last Listing Agent John Zubretsky Century 21 AllPoints Realty

    6 Pelton 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 $638,217

    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 $475,465

    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 $704,473

    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 $423,882

    Last Listing Agent Gigi Giordano Taylor Compass Connecticut, LLC

    79 Middlesex Ave, 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 $1,165,873

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

    25 Gilbert Hill Rd, Chester, CT 06412
  • 6 Ridge Rd, Chester, CT 06412

    $345,000

    Sold Aug 20, 2025

    6 Ridge Rd, Chester, CT 06412

    • 3 Beds
    • 2 Baths
    • 1,472 Sq Ft
    • Built 1980

    Last Sold Summary

    • 5% Above List Price
    • $234/SF
    • 31 Days On Market

    Current Estimated Value $359,267

    Last Listing Agent Craig Milton Re/Max Valley Shore

    6 Ridge 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 $759,693

    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 $226,606

    Last Listing Agent Sharon Linder Berkshire Hathaway NE Prop.

    19 Castle View Dr, Chester, CT 06412
  • 96 Goose Hill Rd, Chester, CT 06412

    $370,000

    Sold Jul 09, 2025

    96 Goose Hill Rd, Chester, CT 06412

    • 1 Bed
    • 1 Bath
    • 642 Sq Ft
    • Built 2017

    Last Sold Summary

    • 12% Above List Price
    • $576/SF
    • 3 Days On Market

    Current Estimated Value $378,074

    Last Listing Agent Jason Archer PMI Southeast CT

    96 Goose Hill Rd, Chester, CT 06412
  • 4 Sypher Rd, Chester, CT 06412

    $525,000

    Sold Jul 25, 2025

    4 Sypher Rd, Chester, CT 06412

    • 3 Beds
    • 2.5 Baths
    • 2,272 Sq Ft
    • Built 1969

    Last Sold Summary

    • 5% Above List Price
    • $231/SF
    • 29 Days On Market

    Current Estimated Value $573,154

    Last Listing Agent Kelly Puorro Puorro Realty Group

    4 Sypher 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 $739,085.
What is the average time to sell a house in Chester, CT?
The houses for sale in Chester, CT spend an average of 64 days on the market.
What is the number of active homes for sale in Chester, CT?
There are 5 active homes for sale in Chester, CT.
How many homes have sold over the last 12 months in Chester, CT?
40 homes have sold in Chester, CT over the last 12 months.

Home Price Trends

Median Sale Price
$614,000
Median Single Family Sale Price
$618,000
Median 2 Bedroom Sale Price
$410,000
Median 1 Bedroom Sale Price
$370,000
Average Price Per Sq Ft
$352
Number of Homes for Sale
5
Last 12 months Home Sales
40
Months of Supply
1.50
Median List Price
$649,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
23%
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