Chestertown, NY Homes

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  /31

  $285,000 Sold Dec 08, 2025

  251 Stock Farm Rd, Chestertown, NY 12817

  • 2 Beds
  • 1 Bath
  • 1,320 Sq Ft
  • Built 1980

  Last Sold Summary

  • 5% Below List Price
  • $216/SF
  • 25 Days On Market

  Last Listing Agent Mary Cummings KW Platform

  251 Stock Farm Rd, Chestertown, NY 12817
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  /44

  Not Listed For Sale

  1 Pine St, Chestertown, NY 12817

  • 6 Beds
  • 3.5 Baths
  • 3,300 Sq Ft
  • Built 1870

  1 Pine St, Chestertown, NY 12817

  Last Sold Summary

  • $102/SF
  • 122 Days On Market

  Last Sold Price $337,500

  Last Listing Agent Julia Pucciarelli Gallo Realty ADK Inc
• 

  

  

  /51

  $215,000 Sold Oct 14, 2025

  25 Schroon River Forest, Chestertown, NY 12817

  • 3 Beds
  • 1 Bath
  • 920 Sq Ft
  • Built 1977

  Last Sold Summary

  • 9% Below List Price
  • $234/SF
  • 325 Days On Market

  Current Estimated Value $235,086

  Last Listing Agent Angie Mead Gallo Realty ADK Inc

  25 Schroon River Forest, Chestertown, NY 12817
• 

  

  

  /20

  Est $268,118 Not Listed For Sale

  21 Laflure Ln, Chestertown, NY 12817

  • 3 Beds
  • 2 Baths
  • 1,673 Sq Ft
  • Built 1975

  21 Laflure Ln, Chestertown, NY 12817

  Last Sold Summary

  • 22% Above List Price
  • $132/SF
  • 18 Days On Market

  Last Sold Price $220,000

  Last Listing Agent Julia Pucciarelli Gallo Realty ADK Inc
• 

  

  

  /3

  $565,000 Sold Dec 12, 2025

  180 E Kelm Pond Rd, Chestertown, NY 12817

  • 2 Beds
  • 3 Baths
  • 864 Sq Ft
  • Built 1978

  Last Sold Summary

  • $654/SF

  Current Estimated Value $559,374

  Last Listing Agent Kevin Truax Davies-Davies & Assoc Real Est

  180 E Kelm Pond Rd, Chestertown, NY 12817
• 

  

  /69

  Est $373,294 Not Listed For Sale

  8 Katy Brooke Ln, Chestertown, NY 12817

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft
  • Built 1988

  8 Katy Brooke Ln, Chestertown, NY 12817

  Last Sold Summary

  • 17% Above List Price
  • $179/SF
  • 13 Days On Market

  Last Sold Price $320,000

  Last Listing Agent Sherrill Hazelton Hunt Real Estate
• 

  

  /36

  $320,000 Sold Jul 11, 2025

  1007 Friends Lake Rd, Chestertown, NY 12817

  • 5 Beds
  • 2.5 Baths
  • 1,166 Sq Ft
  • Built 1975

  Last Sold Summary

  • 24% Below List Price
  • $274/SF
  • 147 Days On Market

  Current Estimated Value $359,695

  Last Listing Agent Saraha Millington Gallo Realty ADK Inc

  1007 Friends Lake Rd, Chestertown, NY 12817
• 

  

  /49

  Est $606,026 Not Listed For Sale

  53 Pine Notch Rd, Chestertown, NY 12817

  • 4 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1974

  53 Pine Notch Rd, Chestertown, NY 12817

  Last Sold Summary

  • 3% Above List Price
  • $318/SF
  • 23 Days On Market

  Last Sold Price $588,000

  Last Listing Agent Walter Swartz Gallo Realty ADK Inc
• 

  

  /26

  $258,000 Sold Jun 11, 2025

  16 B Evergreen Rd, Chestertown, NY 12817

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft
  • Built 1984

  Last Sold Summary

  • 6% Below List Price
  • $207/SF
  • 27 Days On Market

  Last Listing Agent Terry Weinman Coldwell Banker Prime Properties

  16 B Evergreen Rd, Chestertown, NY 12817
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  /22

  Not Listed For Sale

  10 High Pines Terrace Unit 10 D, Chestertown, NY 12817

  • 1 Bed
  • 1.5 Baths
  • 715 Sq Ft
  • Built 1950

  10 High Pines Terrace Unit 10 D, Chestertown, NY 12817

  Last Sold Summary

  • $178/SF
  • 4 Days On Market

  Last Sold Price $127,297

  Last Listing Agent James Nester Cork Nester's True North Prop
• 

  

  /18

  $145,000 Sold Oct 30, 2025

  97 Riverside Dr, Chestertown, NY 12817

  • 2 Beds
  • 2 Baths
  • 2,016 Sq Ft
  • Built 1850

  Last Sold Summary

  • 3% Below List Price
  • $72/SF
  • 20 Days On Market

  Current Estimated Value $145,968

  Last Listing Agent Marina Feeney Howard Hanna

  97 Riverside Dr, Chestertown, NY 12817
• 

  

  /20

  Not Listed For Sale

  1058 Landon Hill Rd, Chestertown, NY 12817

  • 2 Beds
  • 1 Bath
  • 1,108 Sq Ft
  • Built 1951

  1058 Landon Hill Rd, Chestertown, NY 12817

  Last Sold Summary

  • $131/SF
  • 5 Days On Market

  Last Sold Price $145,000

  Last Listing Agent Mary Sullivan Hunt Real Estate
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  /52

  $490,000 Sold Mar 18, 2026

  367 Potter Brook Rd, Chestertown, NY 12817

  • 3 Beds
  • 1.5 Baths
  • 2,752 Sq Ft
  • Built 1970

  Last Sold Summary

  • 17% Below List Price
  • $178/SF
  • 115 Days On Market

  Current Estimated Value $586,490

  Last Listing Agent Sean Rogge Howard Hanna

  367 Potter Brook Rd, Chestertown, NY 12817
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  /38

  Est $371,790 Not Listed For Sale

  27 Balsam Crest Ln Unit C, Chestertown, NY 12817

  • 2 Beds
  • 2.5 Baths
  • 1,988 Sq Ft
  • Built 2005

  27 Balsam Crest Ln Unit C, Chestertown, NY 12817

  Last Sold Summary

  • 11% Above List Price
  • $169/SF
  • 107 Days On Market

  Last Sold Price $335,000

  Last Listing Agent Maureen Iglewski Howard Hanna Capital Inc
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  /51

  $310,000 Sold Dec 22, 2025

  5 Overlook Ln N Unit B & D, Chestertown, NY 12817

  • 4 Beds
  • 4 Baths
  • 840 Sq Ft
  • Built 1940

  Last Sold Summary

  • 5% Below List Price
  • $369/SF
  • 0 Days On Market

  Last Listing Agent Joseph Cardinale Howard Hanna Capital, Inc. (Clifton Park)

  5 Overlook Ln N Unit B & D, Chestertown, NY 12817
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  /11

  Not Listed For Sale

  L6 State Route 9, Chestertown, NY

  L6 State Route 9, Chestertown, NY

  Last Sold Summary

  • 14 Days On Market

  Last Sold Price $172,000

  Last Listing Agent Frank Morehouse Najer Realty
• 

  

  /53

  $1,213,000 Sold Oct 20, 2025

  972 Friends Lake Rd, Chestertown, NY 12817

  • 3 Beds
  • 2 Baths
  • 2,316 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Above List Price
  • $524/SF
  • 4 Days On Market

  Current Estimated Value $1,181,869

  Last Listing Agent Mark Pawlows Bonafide Realty Group

  972 Friends Lake Rd, Chestertown, NY 12817
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  /29

  Est $746,025 Not Listed For Sale

  3 Loon Lake Heights Rd, Chestertown, NY 12817

  • 3 Beds
  • 3 Baths
  • 2,001 Sq Ft
  • Built 2005

  3 Loon Lake Heights Rd, Chestertown, NY 12817

  Last Sold Summary

  • 8% Below List Price
  • $407/SF
  • 33 Days On Market

  Last Sold Price $815,000

  Last Listing Agent Sandi Engle-pratt Gore Mountain Real Estate Company
• 

  

  /30

  $250,000 Sold Sep 04, 2025

  94 Clarkson Rd, Chestertown, NY 12817

  • 2 Beds
  • 1 Bath
  • 560 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Below List Price
  • $446/SF
  • 0 Days On Market

  Current Estimated Value $252,574

  Last Listing Agent Walter Swartz Gallo Realty ADK Inc

  94 Clarkson Rd, Chestertown, NY 12817
• 

  

  /20

  Est $325,719 Not Listed For Sale

  21 White Schoolhouse Rd, Chestertown, NY 12817

  • 2 Beds
  • Built 1930

  21 White Schoolhouse Rd, Chestertown, NY 12817

  Last Sold Summary

  • 365% Above List Price
  • $86/SF
  • 73 Days On Market

  Last Sold Price $70,000

  Last Listing Agent Walter Swartz Gallo Realty ADK Inc
• 

  

  /41

  $725,000 Sold Jan 22, 2026

  5387-5391 New York 8, Chestertown, NY 12817

  • 4 Beds
  • 2 Baths
  • 1,768 Sq Ft
  • Built 1860

  Last Sold Summary

  • $410/SF
  • 3 Days On Market

  Current Estimated Value $735,777

  Last Listing Agent Ashley Nagy Davies-Davies & Assoc Real Est

  5387-5391 New York 8, Chestertown, NY 12817
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  /26

  Est $129,900 Not Listed For Sale

  27 White Schoolhouse Rd, Chestertown, NY 12817

  • 1 Bed
  • Built 1930

  27 White Schoolhouse Rd, Chestertown, NY 12817

  Last Sold Summary

  • 73% Above List Price
  • $122/SF
  • 299 Days On Market

  Last Sold Price $75,000

  Last Listing Agent Walter Swartz Gallo Realty ADK Inc
• 

  

  /26

  $220,000 Sold Oct 28, 2025

  23 Theriot Ave, Chestertown, NY 12817

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Built 1930

  Last Sold Summary

  • $183/SF
  • 23 Days On Market

  Current Estimated Value $212,693

  Last Listing Agent Walter Swartz Gallo Realty ADK Inc

  23 Theriot Ave, Chestertown, NY 12817
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  /49

  Est $372,647 Not Listed For Sale

  28 Balsam Crest Ln Unit B, Chestertown, NY 12817

  • 3 Beds
  • 2.5 Baths
  • 1,988 Sq Ft
  • Built 2005

  28 Balsam Crest Ln Unit B, Chestertown, NY 12817

  Last Sold Summary

  • 6% Above List Price
  • $176/SF
  • 8 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Maureen Iglewski Howard Hanna Capital Inc
• 

  

  /36

  $570,000 Sold Dec 10, 2025

  22 Memory Ln, Chestertown, NY 12817

  • 3 Beds
  • 1 Bath
  • 1,156 Sq Ft
  • Built 1985

  Last Sold Summary

  • $493/SF
  • 4 Days On Market

  Current Estimated Value $553,897

  Last Listing Agent Barbara Kearney Hunt ERA

  22 Memory Ln, Chestertown, NY 12817
• 

  

  /37

  Est $141,440 Not Listed For Sale

  3 High Pines Terrace Unit A, Chestertown, NY 12817

  • 1 Bed
  • 1.5 Baths
  • 848 Sq Ft
  • Built 1910

  3 High Pines Terrace Unit A, Chestertown, NY 12817

  Last Sold Summary

  • 4% Above List Price
  • $160/SF
  • 4 Days On Market

  Last Sold Price $136,000

  Last Listing Agent Joseph Cardinale Howard Hanna Capital Inc
• 

  

  /38

  $192,000 Sold Dec 04, 2025

  11 Overlook Ln N Unit L, Chestertown, NY 12817

  • 3 Beds
  • 2 Baths
  • 840 Sq Ft
  • Built 1940

  Last Sold Summary

  • 4% Below List Price
  • $229/SF
  • 56 Days On Market

  Current Estimated Value $191,312

  Last Listing Agent Joseph Cardinale Howard Hanna Capital Inc

  11 Overlook Ln N Unit L, Chestertown, NY 12817
• 

  

  /49

  Est $777,224 Not Listed For Sale

  17 Kingsley Ln, Chestertown, NY 12817

  • 3 Beds
  • 2.5 Baths
  • 2,486 Sq Ft
  • Built 2020

  17 Kingsley Ln, Chestertown, NY 12817

  Last Sold Summary

  • 7% Above List Price
  • $292/SF
  • 6 Days On Market

  Last Sold Price $725,000

  Last Listing Agent Jill Brady Hunt ERA
• 

  /2

  $135,000 Sold Jun 17, 2025

  112 Green Mansions Rd Unit 1A, Chestertown, NY 12817

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft
  • Built 1958

  Last Sold Summary

  • $150/SF
  • 2 Days On Market

  Last Listing Agent Catherine Combs Julie & Co Realty LLC

  112 Green Mansions Rd Unit 1A, Chestertown, NY 12817
• 

  

  /4

  Est $474,131 Not Listed For Sale

  2 Vanderwalker Rd, Chestertown, NY 12817

  • 3 Beds
  • Built 1990

  2 Vanderwalker Rd, Chestertown, NY 12817

  Last Sold Summary

  • 1,535% Above List Price
  • $16/SF
  • 4 Days On Market

  Last Sold Price $29,000

  Last Listing Agent Angie Mead Gallo Realty ADK Inc
• 

  

  /56

  $549,900 Sold Nov 21, 2025

  20 Marina Rd, Chestertown, NY 12817

  • 3 Beds
  • 2 Baths
  • 968 Sq Ft
  • Built 2022

  Last Sold Summary

  • $568/SF
  • 4 Days On Market

  Current Estimated Value $545,081

  Last Listing Agent Jennifer Ball Hunt ERA

  20 Marina Rd, Chestertown, NY 12817
• 

  

  /40

  Not Listed For Sale

  7232 U S 9, Chestertown, NY 12817

  • 4 Beds
  • 2 Baths
  • 2,536 Sq Ft
  • Built 2004

  7232 U S 9, Chestertown, NY 12817

  Last Sold Summary

  • $487/SF
  • 12 Days On Market

  Last Sold Price $1,235,000

  Last Listing Agent Barbara Kearney Najer Realty
• 

  

  /69

  $561,000 Sold Mar 19, 2026

  4895 New York 8, Chestertown, NY 12817

  • 4 Beds
  • 2 Baths
  • 2,640 Sq Ft
  • Built 1955

  Last Sold Summary

  • 17% Above List Price
  • $212/SF
  • 10 Days On Market

  Last Listing Agent Walter Swartz Gallo Realty ADK Inc

  4895 New York 8, Chestertown, NY 12817
• 

  

  /22

  Est $234,848 Not Listed For Sale

  22 Balsam Crest Ct Unit C, Chestertown, NY 12817

  • 3 Beds
  • 2 Baths
  • 1,052 Sq Ft
  • Built 1993

  22 Balsam Crest Ct Unit C, Chestertown, NY 12817

  Last Sold Summary

  • 24% Above List Price
  • $181/SF
  • 105 Days On Market

  Last Sold Price $190,000

  Last Listing Agent Anna Bennett Lafontaine Selling ADK
• 

  

  /22

  $290,000 Sold Apr 28, 2025

  650 Landon Hill Rd, Chestertown, NY 12817

  • 3 Beds
  • 2 Baths
  • 2,128 Sq Ft
  • Built 1980

  Last Sold Summary

  • $136/SF
  • 8 Days On Market

  Current Estimated Value $291,163

  Last Listing Agent Carol Monroe Najer Realty

  650 Landon Hill Rd, Chestertown, NY 12817
• 

  

  /52

  Est $371,420 Not Listed For Sale

  29 Balsam Crest Ln Unit C, Chestertown, NY 12817

  • 3 Beds
  • 2.5 Baths
  • 1,466 Sq Ft
  • Built 2007

  29 Balsam Crest Ln Unit C, Chestertown, NY 12817

  Last Sold Summary

  • 6% Above List Price
  • $239/SF
  • 3 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Brenda Ziegler Howard Hanna Capital Inc
• 

  

  /28

  $72,500 Sold Apr 11, 2025

  432 White Schoolhouse Rd, Chestertown, NY 12817

  • 3 Beds
  • 1.5 Baths
  • 860 Sq Ft
  • Built 1963

  Last Sold Summary

  • 39% Below List Price
  • $84/SF
  • 153 Days On Market

  Current Estimated Value $117,667

  Last Listing Agent Walter Swartz Gallo Realty ADK Inc

  432 White Schoolhouse Rd, Chestertown, NY 12817
• 

  

  /16

  Not Listed For Sale

  15 B Evergreen Rd Unit 15B, Chestertown, NY 12817

  • 2 Beds
  • 1.5 Baths
  • 1,248 Sq Ft
  • Built 1985

  15 B Evergreen Rd Unit 15B, Chestertown, NY 12817

  Last Sold Summary

  • $224/SF
  • 101 Days On Market

  Last Sold Price $280,000

  Last Listing Agent John Palermo John R. Palermo
• 

  

  /20

  $225,000 Sold Oct 06, 2025

  11 Overlook Ln S Unit A, Chestertown, NY 12817

  • 2 Beds
  • 1.5 Baths
  • 1,020 Sq Ft
  • Built 1980

  Last Sold Summary

  • 6% Below List Price
  • $221/SF
  • 33 Days On Market

  Last Listing Agent Barbara Kearney Hunt ERA

  11 Overlook Ln S Unit A, Chestertown, NY 12817
• 

  

  /21

  Est $314,338 Not Listed For Sale

  97 Jones Rd, Chestertown, NY 12817

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 2000

  97 Jones Rd, Chestertown, NY 12817

  Last Sold Summary

  • 24% Above List Price
  • $222/SF
  • 52 Days On Market

  Last Sold Price $253,575

  Last Listing Agent Julia Pucciarelli Gallo Realty ADK Inc

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