232

Recently Sold Chester, MD Homes

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  • /53

    $475,000

    Sold Sep 29, 2025

    203 Barren Ridge Rd, Chester, MD 21619

    • 3 Beds
    • 1.5 Baths
    • 2,072 Sq Ft
    • Built 1988

    Last Sold Summary

    • $229/SF
    • 38 Days On Market

    Current Estimated Value $512,204

    Last Listing Agent Beth Bearinger Keller Williams Gateway LLC

    203 Barren Ridge Rd, Chester, MD 21619
  • /43

    $1,025,000

    Sold Nov 26, 2025

    318 Old Point Rd, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,656 Sq Ft
    • Built 2024

    Last Sold Summary

    • $619/SF
    • 6 Days On Market

    Current Estimated Value $1,062,317

    Last Listing Agent Annie Eaton Coldwell Banker Realty

    318 Old Point Rd, Chester, MD 21619
  • /14

    $629,990

    Sold Jul 15, 2026

    102 Boatswain Way Unit 11, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $315/SF
    • 25 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    102 Boatswain Way Unit 11, Chester, MD 21619
  • /2

    $430,000

    Sold Jan 23, 2026

    1407 Calvert Rd, Chester, MD 21619

    • 3 Beds
    • 1.5 Baths
    • 1,693 Sq Ft
    • Built 1966

    Last Sold Summary

    • $254/SF
    • 2 Days On Market

    Current Estimated Value $451,186

    Last Listing Agent Dina Baxter Rosendale Realty

    1407 Calvert Rd, Chester, MD 21619
  • /88

    $624,900

    Sold Sep 19, 2025

    211 Switchgrass Way Unit 1524, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2024

    Last Sold Summary

    • $240/SF
    • 147 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    211 Switchgrass Way Unit 1524, Chester, MD 21619
  • /2

    $445,000

    Sold Jul 31, 2026

    1872 Harbor Dr, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 1,486 Sq Ft
    • Built 1961

    Last Sold Summary

    • 8% Below List Price
    • $299/SF
    • 49 Days On Market

    Current Estimated Value $452,572

    Last Listing Agent Joelle Dolch Cross Street Realtors LLC

    1872 Harbor Dr, Chester, MD 21619
  • /8

    $849,990

    Sold Dec 10, 2025

    117 Redstart Dr, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,010 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $423/SF
    • 7 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Single Family

    117 Redstart Dr, Chester, MD 21619
  • /81

    $787,500

    Sold Aug 07, 2026

    135 Nauset Ln, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 2,795 Sq Ft
    • Built 2020

    Last Sold Summary

    • 3% Below List Price
    • $282/SF
    • 230 Days On Market

    Current Estimated Value $811,120

    Last Listing Agent Riley White Real Broker, LLC - Annapolis

    135 Nauset Ln, Chester, MD 21619
  • /18

    $949,990

    Sold Apr 22, 2026

    110 Boatswain Way Unit 41, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 9% Below List Price
    • $365/SF
    • 35 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    110 Boatswain Way Unit 41, Chester, MD 21619
  • /40

    $640,000

    Sold Jan 05, 2026

    132 Claiborne St, Chester, MD 21619

    • 3 Beds
    • 3.5 Baths
    • 2,400 Sq Ft
    • Built 2011

    Last Sold Summary

    • $267/SF
    • 20 Days On Market

    Current Estimated Value $679,188

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    132 Claiborne St, Chester, MD 21619
  • /40

    $540,656

    Sold Sep 19, 2025

    112 Harbour Sound Dr, Chester, MD 21619

    • 2 Beds
    • 3.5 Baths
    • 2,131 Sq Ft
    • Built 1989

    Last Sold Summary

    • $254/SF
    • 86 Days On Market

    Current Estimated Value $541,200

    Last Listing Agent Carlos Larraz Annapolis Properties LLC

    112 Harbour Sound Dr, Chester, MD 21619
  • /77

    $488,000

    Sold Apr 17, 2026

    1337 Queen Anne Dr, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,128 Sq Ft
    • Built 1973

    Last Sold Summary

    • 2% Above List Price
    • $229/SF
    • 15 Days On Market

    Current Estimated Value $486,594

    Last Listing Agent Caitlin Prossner Long & Foster Real Estate, Inc.

    1337 Queen Anne Dr, Chester, MD 21619
  • /60

    $339,900

    Sold Jan 14, 2026

    30 C Queen Mary Ct, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,440 Sq Ft
    • Built 1999

    Last Sold Summary

    • $236/SF
    • 81 Days On Market

    Last Listing Agent Dori Savani Douglas Realty, LLC

    30 C Queen Mary Ct, Chester, MD 21619
  • /30

    $1,350,000

    Sold Feb 24, 2026

    132 Wheelhouse Way Unit 43, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $711/SF
    • 9,551 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    132 Wheelhouse Way Unit 43, Chester, MD 21619
  • /41

    $685,000

    Sold May 11, 2026

    1700 Saint Marys Rd, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,898 Sq Ft
    • Built 1977

    Last Sold Summary

    • 1% Above List Price
    • $361/SF
    • 5 Days On Market

    Current Estimated Value $693,905

    Last Listing Agent Dee Dee McCracken Coldwell Banker Realty

    1700 Saint Marys Rd, Chester, MD 21619
  • /38

    $480,000

    Sold Jun 24, 2026

    1848 Harbor Dr, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 1,804 Sq Ft
    • Built 1992

    Last Sold Summary

    • 3% Below List Price
    • $266/SF
    • 35 Days On Market

    Current Estimated Value $483,764

    Last Listing Agent Colleen Smith EXP Realty, LLC

    1848 Harbor Dr, Chester, MD 21619
  • /24

    $224,000

    Sold Sep 04, 2025

    2653 Cox Neck Rd, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 1,560 Sq Ft
    • Built 1975

    Last Sold Summary

    • 52% Below List Price
    • $144/SF
    • 94 Days On Market

    Current Estimated Value $314,903

    Last Listing Agent BJ Kilby Eastern Shore Real Estate, LLC

    2653 Cox Neck Rd, Chester, MD 21619
  • /106

    $630,000

    Sold Oct 30, 2025

    204 Skipper Ln, Chester, MD 21619

    • 6 Beds
    • 3 Baths
    • 3,760 Sq Ft
    • Built 1968

    Last Sold Summary

    • 3% Below List Price
    • $168/SF
    • 40 Days On Market

    Current Estimated Value $665,704

    Last Listing Agent Andy Schweigman Douglas Realty, LLC

    204 Skipper Ln, Chester, MD 21619
  • /71

    $965,000

    Sold May 07, 2026

    102 Carriage Heath, Chester, MD 21619

    • 4 Beds
    • 3.5 Baths
    • 2,940 Sq Ft
    • Built 2015

    Last Sold Summary

    • 2% Above List Price
    • $328/SF
    • 1 Day On Market

    Current Estimated Value $971,932

    Last Listing Agent Tricia Wilson Wilson Realty & Staging LLC

    102 Carriage Heath, Chester, MD 21619
  • /30

    $644,990

    Sold Jan 13, 2026

    630 Warbler Way Unit 33, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • $339/SF
    • 39 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    630 Warbler Way Unit 33, Chester, MD 21619
  • /55

    $500,900

    Sold Sep 05, 2025

    211 Switchgrass Way Unit 1511, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,000 Sq Ft
    • Built 2024

    Last Sold Summary

    • $250/SF
    • 12 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    211 Switchgrass Way Unit 1511, Chester, MD 21619
  • /62

    $699,990

    Sold Jul 01, 2026

    630 Warbler Way Unit 2224, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2025

    Last Sold Summary

    • $269/SF
    • 248 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2224, Chester, MD 21619
  • /38

    $370,000

    Sold Oct 03, 2025

    204 Dominion Ln, Chester, MD 21619

    • 4 Beds
    • 1 Bath
    • 1,492 Sq Ft
    • Built 1965

    Last Sold Summary

    • $248/SF
    • 13 Days On Market

    Current Estimated Value $383,258

    Last Listing Agent James Real Estate Group EXP Realty, LLC

    204 Dominion Ln, Chester, MD 21619
  • /30

    $689,990

    Sold Jun 03, 2026

    110 Boatswain Way Unit 32, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 13% Below List Price
    • $363/SF
    • 22 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    110 Boatswain Way Unit 32, Chester, MD 21619
  • /40

    $969,990

    Sold Jun 16, 2026

    121 Kinglet Ct, Chester, MD 21619

    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 12% Below List Price
    • $301/SF
    • 20 Days On Market

    Current Estimated Value $977,635

    K. Hovnanian Homes Four Seasons at Kent Island - Single Family

    121 Kinglet Ct, Chester, MD 21619
  • /124

    $784,400

    Sold Nov 24, 2025

    129 Kirwans Landing Ln, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,630 Sq Ft
    • Built 1988

    Last Sold Summary

    • $298/SF
    • 23 Days On Market

    Current Estimated Value $817,485

    Last Listing Agent Noah Mumaw Monument Sotheby's International Realty

    129 Kirwans Landing Ln, Chester, MD 21619
  • /71

    $895,000

    Sold Feb 26, 2026

    115 Cedar Rd, Chester, MD 21619

    • 5 Beds
    • 4 Baths
    • 4,275 Sq Ft
    • Built 2006

    Last Sold Summary

    • 3% Below List Price
    • $209/SF
    • 11 Days On Market

    Current Estimated Value $904,532

    Last Listing Agent Kathleen Higginbotham Samson Properties

    115 Cedar Rd, Chester, MD 21619
  • /2

    $338,000

    Sold Jun 18, 2026

    34 Queen Anne Way Unit F, Chester, MD 21619

    • 1 Bed
    • 1 Bath
    • 724 Sq Ft
    • Built 1983

    Last Sold Summary

    • 3% Below List Price
    • $467/SF
    • 52 Days On Market

    Last Listing Agent Joelle Dolch Cross Street Realtors LLC

    34 Queen Anne Way Unit F, Chester, MD 21619
  • /58

    $659,900

    Sold Feb 20, 2026

    121 Wheelhouse Way Unit 2132, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2025

    Last Sold Summary

    • 3% Below List Price
    • $347/SF
    • 26 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    121 Wheelhouse Way Unit 2132, Chester, MD 21619
  • /37

    $510,000

    Sold Mar 27, 2026

    112 Chessie Ct, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,066 Sq Ft
    • Built 2000

    Last Sold Summary

    • $247/SF
    • 85 Days On Market

    Current Estimated Value $503,953

    Last Listing Agent Carol Delayo Chaney Homes, LLC

    112 Chessie Ct, Chester, MD 21619
  • /58

    $669,900

    Sold Nov 17, 2025

    201 Switchgrass Way Unit 1433, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2025

    Last Sold Summary

    • $353/SF
    • 26 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    201 Switchgrass Way Unit 1433, Chester, MD 21619
  • /86

    $545,000

    Sold Sep 04, 2025

    24 D Queen Elizabeth Ct, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,680 Sq Ft
    • Built 1985

    Last Sold Summary

    • $324/SF
    • 36 Days On Market

    Last Listing Agent The Williams Home Team Douglas Realty, LLC

    24 D Queen Elizabeth Ct, Chester, MD 21619
  • /87

    $1,300,000

    Sold Jul 17, 2026

    1719 Harbor Dr, Chester, MD 21619

    • 3 Beds
    • 5 Baths
    • 4,208 Sq Ft
    • Built 2006

    Last Sold Summary

    • 13% Below List Price
    • $309/SF
    • 28 Days On Market

    Current Estimated Value $1,374,153

    Last Listing Agent Samantha Grimes Chesapeake Real Estate Associates, LLC

    1719 Harbor Dr, Chester, MD 21619
  • /35

    $519,900

    Sold May 21, 2026

    1921 Harbor Dr, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,000 Sq Ft
    • Built 2026

    Last Sold Summary

    • $260/SF
    • 3 Days On Market

    Current Estimated Value $504,527

    Last Listing Agent DJ Dauses Coldwell Banker Waterman Realty

    1921 Harbor Dr, Chester, MD 21619
  • /87

    $989,000

    Sold Aug 18, 2025

    132 Wheelhouse Way Unit 21, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2023

    Last Sold Summary

    • $380/SF
    • 27 Days On Market

    Last Listing Agent Kathleen Higginbotham Samson Properties

    132 Wheelhouse Way Unit 21, Chester, MD 21619
  • /22

    $699,900

    Sold Aug 28, 2025

    509 Warbler Way, Chester, MD 21666

    • 2 Beds
    • 2 Baths
    • 1,993 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $351/SF
    • 5 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Single Family

    509 Warbler Way, Chester, MD 21666
  • /2

    $205,000

    Sold Dec 26, 2025

    1905 Keister Dr, Chester, MD 21619

    • 3 Beds
    • 1 Bath
    • 1,600 Sq Ft
    • Built 1968

    Last Sold Summary

    • $128/SF

    Current Estimated Value $352,844

    Last Listing Agent Elaina Bellas LPT Realty, LLC

    1905 Keister Dr, Chester, MD 21619
  • /50

    $915,000

    Sold Apr 10, 2026

    635 Dominion Rd, Chester, MD 21619

    • 3 Beds
    • 5 Baths
    • 2,818 Sq Ft
    • Built 2011

    Last Sold Summary

    • $325/SF
    • 27 Days On Market

    Current Estimated Value $934,693

    Last Listing Agent Constance Golihew Coldwell Banker Realty

    635 Dominion Rd, Chester, MD 21619
  • /41

    $853,000

    Sold Mar 10, 2026

    162 Kirwans Landing Ln, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,404 Sq Ft
    • Built 1988

    Last Sold Summary

    • $355/SF
    • 104 Days On Market

    Current Estimated Value $1,225,605

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    162 Kirwans Landing Ln, Chester, MD 21619
  • /19

    $949,990

    Sold Mar 02, 2026

    110 Boatswain Way Unit 34, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 3% Below List Price
    • $365/SF
    • 11 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    110 Boatswain Way Unit 34, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 6

Frequently Asked Questions

What is the average home price in Chester, MD?
Homes for sale in Chester, MD have an average home price of $709,943.
What is the average time to sell a house in Chester, MD?
The houses for sale in Chester, MD spend an average of 371 days on the market.
What is the number of active homes for sale in Chester, MD?
There are 95 active homes for sale in Chester, MD.
How many homes have sold over the last 12 months in Chester, MD?
216 homes have sold in Chester, MD over the last 12 months.

Home Price Trends

Median Sale Price
$669,900
Median Single Family Sale Price
$744,500
Median Townhouse Sale Price
$369,950
Median 2 Bedroom Sale Price
$618,750
Median 1 Bedroom Sale Price
$289,000
Average Price Per Sq Ft
$306
Number of Homes for Sale
95
Last 12 months Home Sales
216
Months of Supply
5.30
Median List Price
$699,995
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
17%
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