Chester, NY Homes

• 

  Est $334,177 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,334 Sq Ft

  1004 Swan Hollow Rd, Monroe, NY 10950

  1004 Swan Hollow Rd, Monroe, NY 10950
• 

  

  

  /22

  $68,900

  • Land
  • 3.37 Acres
  • $20,445 per Acre

  86 Carriage Knoll Rd, Chester, NY 12817

  Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

  Walter Swartz Gallo Realty ADK Inc

  86 Carriage Knoll Rd, Chester, NY 12817
• 

  $350,000 Sold Jul 28, 2025

  2816 Whispering Hills, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Built 1984

  Last Sold Summary

  • $263/SF
  • 23 Days On Market

  Current Estimated Value $354,551

  Last Listing Agent Bernadette Giordano Howard Hanna Rand Realty

  2816 Whispering Hills, Chester, NY 10918
• 

  Est $311,076 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,320 Sq Ft

  902 Swan Hollow Rd, Monroe, NY 10950

  902 Swan Hollow Rd, Monroe, NY 10950
• 

  

  

  /23

  $76,900

  • Land
  • 5.1 Acres
  • $15,078 per Acre

  112 Carriage Knoll Rd, Chester, NY 12817

  Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

  Walter Swartz Gallo Realty ADK Inc

  112 Carriage Knoll Rd, Chester, NY 12817
• 

  $310,000 Sold Jul 21, 2025

  4706 Whispering Hills, Chester, NY 10918

  • 2 Beds
  • 1.5 Baths
  • 1,086 Sq Ft
  • Built 1987

  Last Sold Summary

  • 2% Above List Price
  • $285/SF
  • 18 Days On Market

  Current Estimated Value $309,302

  Last Listing Agent Jessica Evans Keller Williams Hudson Valley

  4706 Whispering Hills, Chester, NY 10918
• 

  Est $323,307 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,334 Sq Ft

  901 Swan Hollow Rd, Monroe, NY 10950

  901 Swan Hollow Rd, Monroe, NY 10950
• 

  

  /8

  $460,000

  • 3 Beds
  • 1.5 Baths
  • 1,728 Sq Ft

  1367 Kings Hwy, Chester, NY 10918

  Historic Colonial Era Home in the Heart of Sugar Loaf, NYLocated just 60 minutes from NYCZoned Residential/CommercialStep into history with this one-of-a-kind 1,750 sq. ft. Colonial era home, where 18th-century charm meets 21st-century opportunity — right in the heart of the artisan hamlet of Sugar Loaf, NY. Original building was built in 1770, this unique property features:• One

  Mark Karten Karten Real Estate Svcs LLC

  1367 Kings Hwy, Chester, NY 10918
• 

  $265,000 Sold Jul 11, 2025

  10 El Dorado Trail, Chester, NY 10918

  • Land
  • 6.3 Acres
  • $42,063 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 152 Days On Market

  Current Estimated Value $261,740

  Last Listing Agent Lisandra Rivera Keller Williams Realty

  10 El Dorado Trail, Chester, NY 10918
• 

  Est $304,250 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,240 Sq Ft

  808 Swan Hollow Rd, Monroe, NY 10950

  808 Swan Hollow Rd, Monroe, NY 10950
• 

  

  /10

  $37,500

  • Land
  • 1.62 Acres
  • $23,148 per Acre

  60 Carriage Knolls Rd, Chester, NY 12817

  Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for

  Walter Swartz Gallo Realty ADK Inc

  60 Carriage Knolls Rd, Chester, NY 12817
• 

  $750,000 Sold May 15, 2025

  16 Spectrum Dr, Chester, NY 10918

  • 3 Beds
  • 4 Baths
  • 2,276 Sq Ft
  • Built 1999

  Last Sold Summary

  • 5% Above List Price
  • $330/SF
  • 16 Days On Market

  Current Estimated Value $758,683

  Last Listing Agent John Olivero Keller Williams Realty

  16 Spectrum Dr, Chester, NY 10918
• 

  Est $345,413 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,840 Sq Ft

  707 Swan Hollow Rd, Monroe, NY 10950

  707 Swan Hollow Rd, Monroe, NY 10950
• 

  

  /25

  $78,900

  • Land
  • 5.76 Acres
  • $13,698 per Acre

  106 Carriage Knoll Rd, Chester, NY 12817

  Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

  Walter Swartz Gallo Realty ADK Inc

  106 Carriage Knoll Rd, Chester, NY 12817
• 

  $800,000 Sold Jun 06, 2025

  118 Murray Dr, Chester, NY 10918

  • 5 Beds
  • 4 Baths
  • 3,418 Sq Ft
  • Built 1978

  Last Sold Summary

  • 6% Below List Price
  • $234/SF
  • 110 Days On Market

  Current Estimated Value $820,393

  Last Listing Agent Brian Caplicki Keller Williams Hudson Valley

  118 Murray Dr, Chester, NY 10918
• 

  Est $352,724 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,825 Sq Ft

  604 Mountain Laurel Dr, Monroe, NY 10950

  604 Mountain Laurel Dr, Monroe, NY 10950
• 

  

  /48

  $750,000

  • 3 Beds
  • 3 Baths
  • 2,870 Sq Ft

  16 Oxford Springs Rd, Chester, NY 10918

  Discover modern living at its best in this beautifully designed 2,870 sq ft contemporary home with flexible floor plan and wonderful tranquility! Set on 4.1 private acres and featuring its own pond and seasonal babbling brook, 16 Oxford Springs Road is perfect for those seeking a full-time residence or Hudson Valley getaway. This home offers retreat-like privacy yet is only minutes to all

  Jennifer Gold RE/MAX Benchmark Realty Group

  16 Oxford Springs Rd, Chester, NY 10918
• 

  $429,000 Sold Feb 06, 2026

  451 Meri Ln, Monroe, NY 10950

  • 3 Beds
  • 3.5 Baths
  • 1,698 Sq Ft
  • Built 2001

  Last Sold Summary

  • 8% Above List Price
  • $253/SF
  • 20 Days On Market

  Last Listing Agent Gary Silberstein Keller Williams Valley Realty

  451 Meri Ln, Monroe, NY 10950
• 

  Est $315,338 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,334 Sq Ft

  601 Mountain Laurel Dr, Monroe, NY 10950

  601 Mountain Laurel Dr, Monroe, NY 10950
• 

  

  /5

  $74,900

  • Land
  • 1.79 Acres
  • $41,844 per Acre

  L4-5 Marina Rd, Chester, NY 12817

  This is two lots combined for better access and development and has beach rights to two beaches shown on map. HOA Owner's association fee includes beach maintenance. HOA board is working toward the possibility of installing a boat docksystem for the future. Presently there is space for non motorized craft on the beaches. Broker (John R. Palermo) is handling this property for his family's LLC

  John Palermo John R. Palermo

  L4-5 Marina Rd, Chester, NY 12817
• 

  $560,000 Sold Jul 01, 2025

  92 Pickerel Rd, Monroe, NY 10950

  • 3 Beds
  • 2 Baths
  • 2,016 Sq Ft
  • Built 1969

  Last Sold Summary

  • 2% Below List Price
  • $278/SF
  • 148 Days On Market

  Current Estimated Value $571,466

  Last Listing Agent Richard Wawrynek Howard Hanna Rand Realty

  92 Pickerel Rd, Monroe, NY 10950
• 

  Est $327,749 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,334 Sq Ft

  204 Mountain Laurel Dr, Monroe, NY 10950

  204 Mountain Laurel Dr, Monroe, NY 10950
• 

  

  /23

  $68,900

  • Land
  • 3.05 Acres
  • $22,590 per Acre

  82 Carriage Knoll Rd, Chester, NY 12817

  Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

  Walter Swartz Gallo Realty ADK Inc

  82 Carriage Knoll Rd, Chester, NY 12817
• 

  $369,900 Sold Jan 22, 2026

  18 Oakland Ave, Chester, NY 10918

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft
  • Built 1955

  Last Sold Summary

  • $341/SF
  • 24 Days On Market

  Last Listing Agent Claude Brischoux Keller Williams Realty

  18 Oakland Ave, Chester, NY 10918
• 

  Est $491,797 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,523 Sq Ft

  62 Lincoln Rd, Monroe, NY 10950

  62 Lincoln Rd, Monroe, NY 10950
• 

  

  /31

  $59,500

  • Land
  • 5.42 Acres
  • $10,978 per Acre

  L7 Macglashan Ln, Chester, NY 12817

  Very nice 5.42 acres of property with plenty of secluded building options. Gently sloping topography with mixed hardwood and conifers throughout. An abundance of wildlife signs from end to end of this parcel. This property is zoned ''Rural Use'' and would be used ideally for a home or cabin (one-primary single family residence) with garage or other auxiliary building. Seller financing possible

  Walter Swartz Gallo Realty ADK Inc

  L7 Macglashan Ln, Chester, NY 12817
• 

  

  /40

  $320,000 Sold Oct 03, 2025

  13 Dewey Rd, Chester, NY 12860

  • 2 Beds
  • 1 Bath
  • 1,155 Sq Ft
  • Built 2004

  Last Sold Summary

  • 10% Below List Price
  • $277/SF
  • 92 Days On Market

  Current Estimated Value $324,139

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

  13 Dewey Rd, Chester, NY 12860
• 

  Est $535,248 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,134 Sq Ft

  59 Wilson Rd, Monroe, NY 10950

  59 Wilson Rd, Monroe, NY 10950
• 

  

  /7

  $39,500

  • Land
  • 2.38 Acres
  • $16,597 per Acre

  22 Carriage Knolls Rd, Chester, NY 12817

  Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for a

  Walter Swartz Gallo Realty ADK Inc

  22 Carriage Knolls Rd, Chester, NY 12817
• 

  

  /8

  $110,000 Sold Dec 18, 2025

  L1.1 Elk Glade Rd, Chester, NY 12817

  • Land
  • 1.24 Acres
  • $88,710 per Acre

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Saraha Millington Gallo Realty ADK Inc

  L1.1 Elk Glade Rd, Chester, NY 12817
• 

  Est $531,558 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,644 Sq Ft

  9 Grant Dr, Monroe, NY 10950

  9 Grant Dr, Monroe, NY 10950
• 

  

  /8

  $849,900

  • 4 Beds
  • 2.5 Baths
  • 2,603 Sq Ft

  32 Mountainside Dr, Chester, NY 10918

  A RARE OPPORTUNITY to build your CUSTOM DREAM HOME on over 20 private acres in the sought-after Cooper's Ridge sub-division! This will truly be a lovely property with land, privacy and wonderful mountain views! This modern farm house cape features over 2,600 sq ft. and is completely CUSTOM and DELIVERED TURN-KEY ... build this home, or bring your own dream plans/ideas! This ONE LEVEL living

  Karen Gauvin Our House Real Estate Group

  32 Mountainside Dr, Chester, NY 10918
• 

  $475,000 Sold Apr 22, 2025

  397 Bellvale Rd, Chester, NY 10918

  • 2 Beds
  • 2 Baths
  • 1,452 Sq Ft
  • Built 1983

  Last Sold Summary

  • $327/SF
  • 45 Days On Market

  Current Estimated Value $500,113

  Last Listing Agent Juan Bautista Serhant LLC

  397 Bellvale Rd, Chester, NY 10918
• 

  Est $491,134 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,644 Sq Ft

  1 Grant Dr, Monroe, NY 10950

  1 Grant Dr, Monroe, NY 10950
• 

  

  /16

  $37,500

  • Land
  • 2 Acres
  • $18,750 per Acre

  13 Carriage Knolls Rd, Chester, NY 12817

  Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for a

  Walter Swartz Gallo Realty ADK Inc

  13 Carriage Knolls Rd, Chester, NY 12817
• 

  $270,000 Sold Apr 28, 2025

  1213 Whispering Hills, Chester, NY 10918

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft
  • Built 1984

  Last Sold Summary

  • 4% Below List Price
  • $249/SF
  • 94 Days On Market

  Current Estimated Value $285,450

  Last Listing Agent Nicholas D'Aloisio Keller Williams Rlty Integrity

  1213 Whispering Hills, Chester, NY 10918
• 

  Est $565,337 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,298 Sq Ft

  9 Adams Ct, Monroe, NY 10950

  9 Adams Ct, Monroe, NY 10950
• 

  

  /4

  $350,000

  • Land
  • 5.1 Acres
  • $68,627 per Acre

  0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918

  Very private lot in mature subdivision of large homes. Home site has been cleared and driveway base laid down. With a small amount of brush-clearing in the tree line there can be views of the valley and watershed lands.

  Theresa Powers Keller Williams Realty

  0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
• 

  

  /13

  $79,500 Sold Dec 09, 2025

  L12 Adirondack Heights Rd Unit Lot 6, Chester, NY 12817

  • Land
  • 14.7 Acres
  • $5,408 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 110 Days On Market

  Last Listing Agent Julia Pucciarelli Gallo Realty ADK Inc

  L12 Adirondack Heights Rd Unit Lot 6, Chester, NY 12817
• 

  Est $517,913 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,894 Sq Ft

  59 Washington Rd, Monroe, NY 10950

  59 Washington Rd, Monroe, NY 10950

Showing Results 241 - 280, Page 7 of 18