Chester, NY Homes

• 

  Est $708,764

  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

  Last Listing Agent Robert Addon Keller Williams Realty
• 

  

  

  /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
• 

  $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 $750,250

  Last Listing Agent Alison Orlando KW Hudson Valley United

  507 Bull Mill Rd, Chester, NY 10918
• 

  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

  Last Listing Agent Jacob Matthews Ellis Sotheby's Intl Realty
• 

  

  

  /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

  Sandra Spector Howard Hanna Rand Realty

  651 Lakes Rd, Monroe, NY 10950
• 

  

  /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
• 

  Est $729,386

  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

  Last Listing Agent Philip Szumlaski Keller Williams Realty
• 

  

  /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
• 

  $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 $823,397

  Last Listing Agent David Hopstein Keller Williams Hudson Valley

  10 Spectrum Dr, Chester, NY 10918
• 

  Est $699,737

  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

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group
• 

  

  /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
• 

  $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 $914,613

  Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

  21 Bull Mine Rd, Chester, NY 10918
• 

  Est $759,606

  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

  Last Listing Agent Claudia Lepore Keller Williams Realty
• 

  

  /29

  $389,900

  • 3 Beds
  • 2 Baths
  • 1,393 Sq Ft

  4114 Whispering Hills, Chester, NY 10918

  WOW! Move right into this 3 Bedroom 2 Full bath "all on one level" (almost 1400 sq.ft.) beautifully maintained and updated END UNIT condo style home! You'll love the bright and open concept layout featuring the living room with vaulted ceilings and a gorgeous floor to ceiling fireplace as the focal point of the space. Within this area is easy access to the private deck (with new slider door)

  Gzim Hakanjin Coldwell Banker Realty

  4114 Whispering Hills, Chester, NY 10918
• 

  $385,000

  Sold Aug 04, 2026

  152 Eagleton Dr, Monroe, NY 10950

  • 2 Beds
  • 2.5 Baths
  • 1,490 Sq Ft
  • Built 1987

  Last Sold Summary

  • $258/SF
  • 24 Days On Market

  Current Estimated Value $384,033

  Last Listing Agent Alissa Taylor-Vetell Keller Williams Realty

  152 Eagleton Dr, Monroe, NY 10950
• 

  Est $724,031

  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

  Last Listing Agent Joel Basch eRealty Advisors, Inc
• 

  

  /9

  $79,995

  Pending

  • 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
• 

  $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 $547,089

  Last Listing Agent Courtney Tablante Keller Williams Realty

  13 Tulip Ln Unit 4, Monroe, NY 10950
• 

  Est $648,281

  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

  Last Listing Agent Frank Rivera Hudson Valley Home Connection
• 

  

  /50

  $1,145,000

  $50K PRICE DROP

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

  19 High St, Chester, NY 10918

  Own One of America's Great Equestrian LandmarksSteeped in history and unlike anything else on the market, The Hambletonian House is a magnificent Victorian estate built in the 19th century by William Rysdyk, owner of the legendary Hambletonian 10—the foundation sire of nearly every modern Standardbred racehorse. More than a remarkable home, this is an opportunity to become the next steward of

  Beth Palma Keller Williams Realty

  19 High St, Chester, NY 10918
• 

  $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 $483,704

  Last Listing Agent Lazar Schvimmer Blooming Realty

  3 Hickory Ln, Monroe, NY 10950
• 

  Est $353,447

  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

  Last Listing Agent Patricia Hyer Howard Hanna Rand Realty
• 

  

  /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
• 

  $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 $318,027

  Last Listing Agent Nikki Grzegorzewski Keller Williams Realty

  65 Hudson St, Chester, NY 10918
• 

  Est $504,420

  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

  Last Listing Agent David Kraus MK Realty Inc
• 

  

  /23

  $62,000

  • Land
  • 11.11 Acres
  • $5,581 per Acre

  62 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

  62 Carriage Knolls 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 $531,906

  Last Listing Agent Christine Koenig Keller Williams Realty

  6 Vista Dr, Chester, NY 10918
• 

  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

  Last Listing Agent Leon Klein Keller Williams Hudson Valley
• 

  

  /43

  $430,000

  $20K PRICE DROP Pending

  • 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
• 

  $998,999

  Sold Aug 03, 2026

  53 Odyssey Dr, Chester, NY 10918

  • 4 Beds
  • 3.5 Baths
  • 4,467 Sq Ft
  • Built 1993

  Last Sold Summary

  • 9% Below List Price
  • $224/SF
  • 342 Days On Market

  Current Estimated Value $983,345

  Last Listing Agent Hilary Ryan Goldman Howard Hanna Rand Realty

  53 Odyssey Dr, Chester, NY 10918
• 

  Est $744,863

  Not Listed For Sale

  1689 Kings Hwy, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 2,682 Sq Ft
  • Built 1999

  1689 Kings Hwy, Chester, NY 10918

  Last Sold Summary

  • 158 Days On Market

  Last Listing Agent Rita Geissler ARC Realty 1 in Sales
• 

  

  /25

  $155,000

  $10K PRICE DROP

  • Land
  • 31,798 Sq Ft
  • $212,329 per Acre

  L3 Emily Ln Unit Lot 3, Chester, NY 12817

  Rare opportunity to own a .73-acre vacant building lot with deeded dock and lake rights on beautiful Loon Lake. Located within the small and intimate Lakemont Association--featuring just 8 members--this property offers a unique chance to secure one of the few lake rights parcels with guaranteed docking. The lot is level and has already undergone selective clearing, making it an ideal canvas for

  Saraha Millington Gallo Realty ADK Inc

  L3 Emily Ln Unit Lot 3, Chester, NY 12817
• 

  $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 $530,592

  Last Listing Agent Karen Gauvin Our House Real Estate Group

  40 Mountainside Dr, Chester, NY 10918
• 

  Est $564,899

  Not Listed For Sale

  128 Booth Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,102 Sq Ft
  • Built 1975

  128 Booth Rd, Chester, NY 10918

  Last Sold Summary

  • 179 Days On Market

  Last Listing Agent Tracy McNamara Keller Williams Realty
• 

  

  /42

  $549,000

  $10K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,374 Sq Ft

  44 Wilson Rd, Monroe, NY 10950

  Welcome to this beautifully maintained 3-bedroom, 3-bath ranch nestled on a quiet dead-end street in the Lake Hill Farms community in the Town of Chester, within the Monroe-Woodbury School District. Offering municipal services, central air conditioning, and exceptional pride of ownership, this home is truly move-in ready. Step inside to a bright and inviting floor plan featuring a spacious living

  Claudia Lepore Keller Williams Realty

  44 Wilson Rd, Monroe, NY 10950
• 

  $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 $316,000

  Last Listing Agent Donna Ramundo Keller Williams Valley Realty

  111 Lake Region Blvd, Monroe, NY 10950
• 

  Est $703,305

  Not Listed For Sale

  71 Winding Trail, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,800 Sq Ft
  • Built 1987

  71 Winding Trail, Chester, NY 10918

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
• 

  

  /3

  $750,000

  • 5 Beds
  • 2.5 Baths
  • 2,700 Sq Ft

  2 Boville Ct, Chester, NY 10918

  Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s

  Moshe Kaufman MK Realty Inc

  2 Boville Ct, 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 Real Estate ERA

  L7 Atateka Dr, Chester, NY 12817
• 

  Est $980,714

  Not Listed For Sale

  2 Park Place, Chester, NY 10918

  • 4 Beds
  • 4.5 Baths
  • 4,492 Sq Ft
  • Built 1999

  2 Park Place, Chester, NY 10918

  Last Sold Summary

  • 97 Days On Market

  Last Listing Agent Claudia Lepore Keller Williams Realty

Showing Results 121 - 160, Page 4 of 18