Chester, NY Homes

• 

  $419,999

  Sold Jan 07, 2026

  354 Rande Rd Unit 354, Monroe, NY 10950

  • 3 Beds
  • 2.5 Baths
  • 1,698 Sq Ft
  • Built 1999

  Last Sold Summary

  • $247/SF
  • 28 Days On Market

  Current Estimated Value $415,378

  Last Listing Agent Joel Ayala HomeSmart Homes & Estates

  354 Rande Rd Unit 354, Monroe, NY 10950
• 

  Est $816,870

  Not Listed For Sale

  118 Murray Dr, Chester, NY 10918

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

  118 Murray Dr, Chester, NY 10918

  Last Sold Summary

  • 110 Days On Market
• 

  

  

  /19

  $74,900

  $19K PRICE INCREASE

  • Land
  • 4.17 Acres
  • $17,962 per Acre

  77 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

  77 Carriage Knoll Rd, Chester, NY 12817
• 

  $389,000

  Sold Jul 09, 2025

  19 Taurus Ave, Monroe, NY 10950

  • 3 Beds
  • 1.5 Baths
  • 1,288 Sq Ft
  • Built 1954

  Last Sold Summary

  • 4% Above List Price
  • $302/SF
  • 30 Days On Market

  Current Estimated Value $386,145

  Last Listing Agent Christian Baez KW Hudson Valley Untied

  19 Taurus Ave, Monroe, NY 10950
• 

  Est $674,071

  Not Listed For Sale

  142 Laroe Rd, Chester, NY 10918

  • 5 Beds
  • 3.5 Baths
  • 3,385 Sq Ft
  • Built 1981

  142 Laroe Rd, Chester, NY 10918

  Last Sold Summary

  • 107 Days On Market
• 

  

  /42

  $499,900

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,888 Sq Ft

  4 Oak St, Chester, NY 10918

  SPRAWLING BRICK RANCH!!! VILLAGE OF CHESTER! ALMOST 1900 SQ. FT. ON THE MAIN LEVEL!!! X- LARGE 1/2 ACRE LOT!!! Welcome to 4 Oak Street, nestled in the charming Village of Chester, NY. Offered for the very first time, this exceptional home was custom built for its original owners and has been lovingly maintained ever since—a true testament to quality craftsmanship and pride of ownership. Set on a

  Frank Muccari Cronin & Company Real Estate

  4 Oak St, Chester, NY 10918
• 

  $675,000

  Sold Feb 18, 2026

  507 Bull Mill Rd, Chester, NY 10918

  • 5 Beds
  • 2.5 Baths
  • 3,115 Sq Ft
  • Built 2003

  Last Sold Summary

  • 4% Below List Price
  • $217/SF
  • 134 Days On Market

  Current Estimated Value $698,087

  Last Listing Agent Alison Orlando KW Hudson Valley Untied

  507 Bull Mill Rd, Chester, NY 10918
• 

  Est $714,188

  Not Listed For Sale

  3 Overlook Trail, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 2,592 Sq Ft
  • Built 1985

  3 Overlook Trail, Chester, NY 10918

  Last Sold Summary

  • 35 Days On Market
• 

  

  /5

  $759,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,250 Sq Ft

  90 Pewter Cir, Chester, NY 10918

  This beautiful custom home is planned to be built in the highly sought-after Sugar Loaf area, offering the convenience of municipal water and sewer. The main level welcomes you with warm hardwood floors and a kitchen featuring a choice of elegant granite or quartz countertops, a stainless steel appliance package, a center island perfect for meal preparation, and a spacious dining area with a

  Carla Terranova Keller Williams Realty

  90 Pewter Cir, Chester, NY 10918
• 

  

  /20

  $155,000

  Sold Apr 01, 2026

  L2 Friends Lake Rd, Chester, NY 12817

  • Land
  • 22.6 Acres
  • $6,858 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 607 Days On Market

  Last Listing Agent Walter Swartz Gallo Realty ADK Inc

  L2 Friends Lake Rd, Chester, NY 12817
• 

  Not Listed For Sale

  282 Laroe Rd, Chester, NY 10918

  • 6 Beds
  • 5 Baths
  • 6,622 Sq Ft
  • Built 1900

  282 Laroe Rd, Chester, NY 10918

  Last Sold Summary

  • 112 Days On Market
• 

  

  /7

  $900,000

  • 4 Beds
  • 2 Baths
  • 2,466 Sq Ft

  651 Lakes Rd, Monroe, NY 10950

  Rare opportunity to purchase this gorgeous property that consists of 3 homes nestled on 3.5 beautiful acres. The main Colonial residence has been gutted and will need to be renovated/rebuilt, however, you can live in one of the additional two residences while you renovate! The 2nd residence called the “stone cottage” has 2 fieldstone fireplaces, a full kitchen, a vaulted ceiling in the bedroom, a

  Frank Golio Howard Hanna Rand Realty

  651 Lakes Rd, Monroe, NY 10950
• 

  $800,000

  Sold Sep 15, 2025

  10 Spectrum Dr, Chester, NY 10918

  • 5 Beds
  • 4 Baths
  • 4,496 Sq Ft
  • Built 1991

  Last Sold Summary

  • 11% Below List Price
  • $178/SF
  • 24 Days On Market

  Current Estimated Value $833,089

  Last Listing Agent David Hopstein eRealty Advisors, Inc

  10 Spectrum Dr, Chester, NY 10918
• 

  Est $586,514

  Not Listed For Sale

  412 Laroe Rd, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • Built 1995

  412 Laroe Rd, Chester, NY 10918

  Last Sold Summary

  • 19 Days On Market
• 

  

  /48

  $1,299,900

  New Construction $150K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 4,508 Sq Ft

  145 Kings Highway Bypass, Chester, NY 10918

  Set gracefully on 3.8 private acres within the highly coveted Warwick School District, this exceptional custom home offers a rare blend of architectural elegance and refined living. Surrounded by a collection of equally distinguished residences, the property provides an expansive, park-like sanctuary while remaining nestled in the heart of one of the region’s most sought-after communities.

  Courtney Tablante Keller Williams Realty

  145 Kings Highway Bypass, Chester, NY 10918
• 

  $905,000

  Sold Jun 18, 2026

  21 Bull Mine Rd, Chester, NY 10918

  • 5 Beds
  • 3.5 Baths
  • 3,680 Sq Ft
  • Built 2002

  Last Sold Summary

  • 2% Below List Price
  • $246/SF
  • 44 Days On Market

  Current Estimated Value $924,715

  Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

  21 Bull Mine Rd, Chester, NY 10918
• 

  Est $721,960

  Not Listed For Sale

  76 Restdale Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,838 Sq Ft
  • Built 1997

  76 Restdale Rd, Chester, NY 10918

  Last Sold Summary

  • 20 Days On Market
• 

  

  /47

  $650,000

  $40K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,636 Sq Ft

  10 Hidden Dr, Monroe, NY 10950

  Tucked away on over an acre with serene lake views and deeded lake rights, this spacious Monroe retreat offers the perfect blend of privacy, comfort, and lifestyle. Wake up to natural light pouring through oversized windows and start your day on the deck overlooking the water. Inside, you’ll find 4 generously sized bedrooms and 3 full baths, along with an updated kitchen and baths that bring a

  rosemary mcginn Century 21 Full Service Realty

  10 Hidden Dr, Monroe, NY 10950
• 

  $555,000

  Sold Sep 18, 2025

  13 Tulip Ln Unit 4, Monroe, NY 10950

  • 3 Beds
  • 2 Baths
  • 1,844 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Above List Price
  • $301/SF
  • 87 Days On Market

  Current Estimated Value $540,571

  Last Listing Agent Courtney Tablante Keller Williams Realty

  13 Tulip Ln Unit 4, Monroe, NY 10950
• 

  Est $708,383

  Not Listed For Sale

  53 Elvis Blvd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,838 Sq Ft
  • Built 1999

  53 Elvis Blvd, Chester, NY 10918

  Last Sold Summary

  • 39 Days On Market
• 

  

  /19

  $429,000

  • 3 Beds
  • 1.5 Baths
  • 1,460 Sq Ft

  4 Maple Ln, Monroe, NY 10950

  Welcome to this beautifully updated Monroe home, ideally located just about 50 minutes from New York City. Set on a lush, well-kept property with mature trees and excellent curb appeal, this move-in-ready home offers a fresh modern look inside and out. The exterior features gray siding, white trim, a black front door, manicured landscaping, a newly paved driveway, and a spacious rear deck

  Joseph Rosenfeld Flag Realty Group

  4 Maple Ln, Monroe, NY 10950
• 

  $294,000

  Sold Feb 10, 2026

  3 Hickory Ln, Monroe, NY 10950

  • 4 Beds
  • 2 Baths
  • 1,760 Sq Ft
  • Built 1961

  Last Sold Summary

  • 9% Below List Price
  • $167/SF
  • 23 Days On Market

  Current Estimated Value $403,278

  Last Listing Agent Lazar Schvimmer Blooming Realty

  3 Hickory Ln, Monroe, NY 10950
• 

  Est $765,665

  Not Listed For Sale

  47 Valley View Dr, Chester, NY 10918

  • 5 Beds
  • 3.5 Baths
  • 3,812 Sq Ft
  • Built 1998

  47 Valley View Dr, Chester, NY 10918

  Last Sold Summary

  • 72 Days On Market
• 

  

  /48

  $795,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,780 Sq Ft

  1071 Craigville Rd, Chester, NY 10918

  This standout 2,780 sq ft Colonial sits on 3 private acres in a prime location, offering space, comfort, and strong value. The upgraded kitchen features granite countertops and a center island, flowing into a bright, functional layout perfect for everyday living.A renovated basement adds flexible bonus space, while the outdoor patio overlooks expansive property—ideal for relaxing or

  Jacob Katz MS Realty Group USA, Inc

  1071 Craigville Rd, Chester, NY 10918
• 

  $305,000

  Sold Feb 20, 2026

  65 Hudson St, Chester, NY 10918

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft
  • Built 1930

  Last Sold Summary

  • 12% Below List Price
  • $272/SF
  • 57 Days On Market

  Current Estimated Value $315,530

  Last Listing Agent Nikki Grzegorzewski Keller Williams Realty

  65 Hudson St, Chester, NY 10918
• 

  Est $673,616

  Not Listed For Sale

  121 Conklingtown Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,599 Sq Ft
  • Built 2000

  121 Conklingtown Rd, Chester, NY 10918

  Last Sold Summary

  • 22 Days On Market
• 

  

  /18

  $189,000

  • Land
  • 3.14 Acres
  • $60,191 per Acre

  2 Dixon Rd, Chester, NY 12817

  Fish, Paddle, Build! Own an incredible 509' of private frontage on the Schroon River, complete with your very own mini island and over 3 buildable acres to create your Adirondack escape. Driveway is already in place with power available at the road, making your future plans even easier. Located just south of the dam (no direct access to Schroon Lake), this peaceful setting is ideal for fishing,

  Angie Mead Gallo Realty ADK Inc

  2 Dixon Rd, Chester, NY 12817
• 

  $515,000

  Sold Mar 09, 2026

  6 Vista Dr, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,934 Sq Ft
  • Built 1998

  Last Sold Summary

  • 3% Above List Price
  • $266/SF
  • 41 Days On Market

  Current Estimated Value $527,032

  Last Listing Agent Christine Koenig Keller Williams Realty

  6 Vista Dr, Chester, NY 10918
• 

  Est $640,256

  Not Listed For Sale

  79 Conklingtown Rd, Chester, NY 10918

  • 4 Beds
  • 3 Baths
  • 2,636 Sq Ft
  • Built 1988

  79 Conklingtown Rd, Chester, NY 10918

  Last Sold Summary

  • 13 Days On Market
• 

  

  /9

  $79,995

  • Land
  • 20.26 Acres
  • $3,948 per Acre

  1.2 Cobble Creek Rd Unit 2, Chester, NY 12853

  Escape to the mountains with this beautiful 20-acre property in Chester, NY, ideally situated along a year-round maintained town road. The terrain gently climbs from the road, leading to multiple APA-approved building sites for an off-grid cabin or hunting camp offering excellent privacy in a quiet woodland setting. The property features a healthy forest of Northern hardwoods including maple,

  Marc Christmas CHRISTMAS AND ASSOCIATES INC

  1.2 Cobble Creek Rd Unit 2, Chester, NY 12853
• 

  $380,000

  Sold Jul 30, 2025

  3816 Whispering Hills, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Built 1987

  Last Sold Summary

  • 4% Above List Price
  • $285/SF
  • 28 Days On Market

  Current Estimated Value $382,958

  Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

  3816 Whispering Hills, Chester, NY 10918
• 

  Est $361,178

  Not Listed For Sale

  70 Conklingtown Rd, Chester, NY 10918

  • 3 Beds
  • 1 Bath
  • 835 Sq Ft
  • Built 1945

  70 Conklingtown Rd, Chester, NY 10918

  Last Sold Summary

  • 22 Days On Market
• 

  

  /50

  $1,195,000

  • 9 Beds
  • 6.5 Baths
  • 4,965 Sq Ft

  19 High St, Chester, NY 10918

  Own a true piece of history with the iconic Hambletonian House, a one-of-a-kind Victorian estate built in the 19th century by William Rysdyk, original owner of Hambletonian 10—the legendary sire that shaped nearly all modern Standardbred racehorses. Perfectly positioned on nearly three private acres atop a knoll in the heart of Chester, New York, this meticulously maintained property offers a

  Beth Palma Keller Williams Realty

  19 High St, Chester, NY 10918
• 

  $799,900

  Sold Sep 15, 2025

  40 Mountainside Dr, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • Built 2024

  Last Sold Summary

  • $320/SF
  • 47 Days On Market

  Current Estimated Value $542,412

  Last Listing Agent Karen Gauvin Our House Real Estate Group

  40 Mountainside Dr, Chester, NY 10918
• 

  Est $511,822

  Not Listed For Sale

  3976 Summerville Way, Chester, NY 10918

  • 3 Beds
  • 1.5 Baths
  • 1,474 Sq Ft
  • Built 1955

  3976 Summerville Way, Chester, NY 10918

  Last Sold Summary

  • 32 Days On Market
• 

  

  /28

  $500,000

  • 3 Beds
  • 2 Baths
  • 2,688 Sq Ft

  5 N Hudson St Unit N, Chester, NY 10918

  3 bedroom 2 bath contemporary home tucked away on a quiet street. Modern renovation already started, put your finishing touches on it. Home sold as is. Open concept living, spacious kitchen, private primary suite on 2nd floor with 2 additional bedrooms on 1st floor. Peaceful setting and still close to all amenities. 1,000 sq ft 2 car detached garage.

  Bernadette Corrigan Keller Williams Realty

  5 N Hudson St Unit N, Chester, NY 10918
• 

  $310,000

  Sold Apr 29, 2026

  111 Lake Region Blvd, Monroe, NY 10950

  • 2 Beds
  • 1 Bath
  • 792 Sq Ft
  • Built 1950

  Last Sold Summary

  • $391/SF
  • 43 Days On Market

  Current Estimated Value $309,597

  Last Listing Agent Donna Ramundo Keller Williams Valley Realty

  111 Lake Region Blvd, Monroe, NY 10950
• 

  Not Listed For Sale

  3966 Summerville Way, Chester, NY 10918

  • 5 Beds
  • 3 Baths
  • 2,882 Sq Ft
  • Built 1945

  3966 Summerville Way, Chester, NY 10918

  Last Sold Summary

  • 6 Days On Market
• 

  

  /43

  $430,000

  $20K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,177 Sq Ft

  151 Laroe Rd, Chester, NY 10918

  What a remarkable property in the town of Chester, NY-a highly sought after town in the southern Hudson Valley, only 45 minutes from the GW Bridge! This 3 bedroom, 2 bathroom house boasts tons of modern and energy efficient features. A massive renovation done only 5 years ago leaves you with nothing to maintain except to pick your paint colors and finishes. 1st floor main bedroom and additional

  Todd Sullivan Keller Williams Realty

  151 Laroe Rd, Chester, NY 10918
• 

  /2

  $87,500

  Sold Aug 18, 2025

  L7 Atateka Dr, Chester, NY 12817

  • Land
  • 6.38 Acres
  • $13,715 per Acre

  Last Sold Summary

  • 47% Below List Price
  • 608 Days On Market

  Last Listing Agent Jill Brady Hunt ERA

  L7 Atateka Dr, Chester, NY 12817

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