Chester, NY Homes

• 

  Est $288,080 Not Listed For Sale

  808 Swan Hollow Rd, Monroe, NY 10950

  • 3 Beds
  • 1.5 Baths
  • 1,240 Sq Ft
  • Built 1979

  808 Swan Hollow Rd, Monroe, NY 10950

  Last Sold Summary

  • 14% Above List Price
  • $204/SF
  • 32 Days On Market

  Last Sold Price $252,350

  Last Listing Agent Vincent Paolino Keller Williams Hudson Valley
• 

  

  

  /13

  $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
• 

  $290,000 Sold Jun 05, 2025

  4401 Whispering Hills Dr, Chester, NY 10918

  • 2 Beds
  • 1 Bath
  • 1,118 Sq Ft
  • Built 1989

  Last Sold Summary

  • 5% Above List Price
  • $259/SF
  • 30 Days On Market

  Current Estimated Value $297,669

  Last Listing Agent Annmarie Kovacs Howard Hanna Rand Realty

  4401 Whispering Hills Dr, Chester, NY 10918
• 

  Est $351,040 Not Listed For Sale

  707 Swan Hollow Rd, Monroe, NY 10950

  • 3 Beds
  • 2.5 Baths
  • 1,840 Sq Ft
  • Built 1979

  707 Swan Hollow Rd, Monroe, NY 10950

  Last Sold Summary

  • 8% Above List Price
  • $177/SF
  • 78 Days On Market

  Last Sold Price $326,500

  Last Listing Agent Susan Alex Exit Realty Connections
• 

  

  

  /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
• 

  $675,000 Sold Nov 18, 2025

  165 Creamery Pond Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,548 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $265/SF
  • 55 Days On Market

  Current Estimated Value $664,524

  Last Listing Agent Kichka Pascaru Christie's Int. Real Estate

  165 Creamery Pond Rd, Chester, NY 10918
• 

  Est $356,521 Not Listed For Sale

  604 Mountain Laurel Dr, Monroe, NY 10950

  • 3 Beds
  • 2.5 Baths
  • 1,825 Sq Ft
  • Built 1979

  604 Mountain Laurel Dr, Monroe, NY 10950

  Last Sold Summary

  • 5% Above List Price
  • $186/SF
  • 39 Days On Market

  Last Sold Price $340,000

  Last Listing Agent Emmett McDowell Keller Williams Rlty Integrity
• 

  

  /48

  $949,999

  • 5 Beds
  • 4 Baths
  • 5,080 Sq Ft

  4 Camelback Rd, Chester, NY 10918

  Welcome home to 4 Camelback Road. Nestled on a serene cul-de-sac in the executive subdivision of Country Woods, this magnificent home sits on one of the most beautiful streets within the sought-after Monroe-Woodbury School District. Step into perfection as you enter the grand foyer and are immediately welcomed by a light-filled, open floor plan that exudes elegance and sophistication. This

  Alexander Fayn Prominent Properties Sotheby's

  4 Camelback Rd, Chester, NY 10918
• 

  $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 $348,131

  Last Listing Agent Bernadette Giordano Howard Hanna Rand Realty

  2816 Whispering Hills, Chester, NY 10918
• 

  Est $295,711 Not Listed For Sale

  601 Mountain Laurel Dr, Monroe, NY 10950

  • 3 Beds
  • 2.5 Baths
  • 1,334 Sq Ft
  • Built 1979

  601 Mountain Laurel Dr, Monroe, NY 10950

  Last Sold Summary

  • 12% Above List Price
  • $199/SF
  • 29 Days On Market

  Last Sold Price $265,000

  Last Listing Agent Bernadette Corrigan Keller Williams Realty
• 

  

  /29

  $279,900 Pending

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  2913 Whispering Hills Unit 595, Chester, NY 10918

  Welcome to 2913 Whispering Hills Drive – A Move-In Ready End Unit in the Heart of Chester! This bright and spacious 2-bedroom, 1-bath townhouse offers an open-concept layout with soaring vaulted ceilings and an abundance of natural light. As an end unit, you’ll enjoy added privacy along with extra windows that make the space feel even more expansive. The inviting living room features a cozy

  Devon King HomeSmart Homes & Estates

  2913 Whispering Hills Unit 595, Chester, NY 10918
• 

  $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 $308,107

  Last Listing Agent Jessica Evans Keller Williams Hudson Valley

  4706 Whispering Hills, Chester, NY 10918
• 

  Est $310,025 Not Listed For Sale

  204 Mountain Laurel Dr, Monroe, NY 10950

  • 3 Beds
  • 2.5 Baths
  • 1,334 Sq Ft
  • Built 1979

  204 Mountain Laurel Dr, Monroe, NY 10950

  Last Sold Summary

  • 13% Above List Price
  • $206/SF
  • 87 Days On Market

  Last Sold Price $274,500

  Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales
• 

  

  /24

  $362,900 Open Sun 11AM - 1PM

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

  2203 Whispering Hills, Chester, NY 10918

  Welcome to 2203 Whispering Hills, Chester, NY — Where Comfort Meets ConvenienceThis sun-drenched end-unit townhome offers the perfect blend of space, style, and location in the sought-after Whispering Hills community.Featuring 3 spacious bedrooms and 2.5 bathrooms, this home is designed for both everyday comfort and effortless entertaining. The inviting living room is anchored by a cozy

  Marie Altieri Howard Hanna Rand Realty

  2203 Whispering Hills, 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 $258,515

  Last Listing Agent Lisandra Rivera Keller Williams Realty

  10 El Dorado Trail, Chester, NY 10918
• 

  Est $492,056 Not Listed For Sale

  62 Lincoln Rd, Monroe, NY 10950

  • 4 Beds
  • 2 Baths
  • 1,523 Sq Ft
  • Built 1974

  62 Lincoln Rd, Monroe, NY 10950

  Last Sold Summary

  • 13% Above List Price
  • $286/SF
  • 14 Days On Market

  Last Sold Price $435,000

  Last Listing Agent Erin Connolly Artisan Realty
• 

  

  /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
• 

  $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 $735,464

  Last Listing Agent John Olivero Keller Williams Realty

  16 Spectrum Dr, Chester, NY 10918
• 

  Est $540,129 Not Listed For Sale

  59 Wilson Rd, Monroe, NY 10950

  • 4 Beds
  • 2 Baths
  • 2,134 Sq Ft
  • Built 1977

  59 Wilson Rd, Monroe, NY 10950

  Last Sold Summary

  • 10% Above List Price
  • $229/SF
  • 23 Days On Market

  Last Sold Price $489,250

  Last Listing Agent Keith Sumner John J Lease REALTORS Inc
• 

  

  /50

  $820,000 Open Sun 12:30PM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 3,120 Sq Ft

  558 Pine Hill Rd, Chester, NY 10918

  Beautifully spacious Colonial set on 1.8 private acres on Pine Hill Road, offering 3,120 square feet of rustic, updated charm behind a gated entry and surrounded by magnificent grounds. The main level welcomes you with a spacious eat-in kitchen that flows seamlessly into the dining area, creating an ideal setting for everyday living and effortless entertaining. The massively large living room

  Charnie Guttmann eRealty Advisors, Inc

  558 Pine Hill Rd, Chester, NY 10918
• 

  $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 $801,797

  Last Listing Agent Brian Caplicki Keller Williams Hudson Valley

  118 Murray Dr, Chester, NY 10918
• 

  Est $535,463 Not Listed For Sale

  9 Grant Dr, Monroe, NY 10950

  • 4 Beds
  • 2 Baths
  • 1,644 Sq Ft
  • Built 1987

  9 Grant Dr, Monroe, NY 10950

  Last Sold Summary

  • 7% Above List Price
  • $304/SF
  • 23 Days On Market

  Last Sold Price $500,000

  Last Listing Agent Martin Remo RE/MAX Prime Properties
• 

  

  /42

  $305,000 Open Sun 12PM - 3PM

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  3601 Whispering Hills, Chester, NY 10918

  Welcome to effortless living in the highly sought-after Whispering Hills community! This beautifully maintained 2-bedroom, 1-bath condo with a 1-car garage offers the perfect blend of comfort, style, and convenience.Step inside to discover a warm and inviting space enhanced by custom wall detailing, stylish flooring, and a cozy fireplace, creating the perfect setting for relaxing and

  Janet Rendle Weichert Realtors

  3601 Whispering Hills, 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

  Current Estimated Value $397,099

  Last Listing Agent Gary Silberstein Keller Williams Valley Realty

  451 Meri Ln, Monroe, NY 10950
• 

  Est $511,475 Not Listed For Sale

  1 Grant Dr, Monroe, NY 10950

  • 4 Beds
  • 2 Baths
  • 1,644 Sq Ft
  • Built 1989

  1 Grant Dr, Monroe, NY 10950

  Last Sold Summary

  • 8% Above List Price
  • $288/SF
  • 54 Days On Market

  Last Sold Price $473,000

  Last Listing Agent Joanne Finochio Howard Hanna Rand Realty
• 

  

  /43

  $750,000 Pending

  • 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
• 

  $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 $568,646

  Last Listing Agent Richard Wawrynek Howard Hanna Rand Realty

  92 Pickerel Rd, Monroe, NY 10950
• 

  Est $578,047 Not Listed For Sale

  9 Adams Ct, Monroe, NY 10950

  • 3 Beds
  • 2 Baths
  • 2,298 Sq Ft
  • Built 1973

  9 Adams Ct, Monroe, NY 10950

  Last Sold Summary

  • 10% Above List Price
  • $228/SF
  • 21 Days On Market

  Last Sold Price $525,000

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
• 

  

  /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
• 

  $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

  Current Estimated Value $367,483

  Last Listing Agent Claude Brischoux Keller Williams Realty

  18 Oakland Ave, Chester, NY 10918
• 

  Est $570,609 Not Listed For Sale

  59 Washington Rd, Monroe, NY 10950

  • 4 Beds
  • 2 Baths
  • 1,894 Sq Ft
  • Built 1973

  59 Washington Rd, Monroe, NY 10950

  Last Sold Summary

  • 11% Above List Price
  • $272/SF
  • 27 Days On Market

  Last Sold Price $515,000

  Last Listing Agent Rebecca Kane Keller Williams Hudson Valley
• 

  /2

  $350,000

  • Land
  • 5.7 Acres
  • $61,404 per Acre

  552 Pine Hill Rd, Chester, NY 10918

  Beautiful 5.7-acre residential parcel located in the Town of chester, offering an exceptional opportunity to build your custom dream home in a peaceful, private setting. With ample space for a spacious residence and outdoor living areas (subject to town approvals), this property combines natural surroundings with convenient access to nearby amenities, schools, and major roadways. Adjacent to 558

  Charnie Guttmann eRealty Advisors, Inc

  552 Pine Hill Rd, Chester, NY 10918
• 

  

  /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 $319,204

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

  13 Dewey Rd, Chester, NY 12860
• 

  Est $533,462 Not Listed For Sale

  26 Harding Way, Monroe, NY 10950

  • 4 Beds
  • 2 Baths
  • 1,744 Sq Ft
  • Built 1979

  26 Harding Way, Monroe, NY 10950

  Last Sold Summary

  • 7% Above List Price
  • $287/SF
  • 58 Days On Market

  Last Sold Price $500,000

  Last Listing Agent Carmela Lopez Borrazas Serhant LLC
• 

  

  /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
• 

  

  /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 $525,183 Not Listed For Sale

  67 Washington Rd, Monroe, NY 10950

  • 5 Beds
  • 2 Baths
  • 2,088 Sq Ft
  • Built 1973

  67 Washington Rd, Monroe, NY 10950

  Last Sold Summary

  • 27% Above List Price
  • $199/SF
  • 25 Days On Market

  Last Sold Price $415,000

  Last Listing Agent Matthew Gibbs Keller Williams Hudson Valley
• 

  

  /20

  $489,000

  • 4 Beds
  • 2 Baths
  • 1,760 Sq Ft

  3 Hickory Ln, Monroe, NY 10950

  Welcome to this beautifully fully renovated 4-bedroom, 2-bath home, thoughtfully updated in 2026 with modern finishes throughout. This spacious property offers a bright open-concept layout featuring a large living room, dining area, and a stunning modern kitchen complete with a skylight and abundant natural light. Enjoy new flooring and moldings throughout, freshly painted interiors, and

  Pearl Ungar eRealty Advisors, Inc

  3 Hickory Ln, Monroe, NY 10950
• 

  $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 $478,069

  Last Listing Agent Juan Bautista Serhant LLC

  397 Bellvale Rd, Chester, NY 10918
• 

  Est $567,608 Not Listed For Sale

  2 Tyler Place, Monroe, NY 10950

  • 4 Beds
  • 2 Baths
  • 1,944 Sq Ft
  • Built 1973

  2 Tyler Place, Monroe, NY 10950

  Last Sold Summary

  • 9% Above List Price
  • $267/SF
  • 36 Days On Market

  Last Sold Price $520,000

  Last Listing Agent Claudia Lepore Keller Williams Realty

Showing Results 241 - 280, Page 7 of 18