Chester, NY Homes

• 

  $125,000 Sold Oct 03, 2025

  0 William Hill Rd, Chester, NY 12817

  • Land
  • 45.83 Acres
  • $2,727 per Acre

  Last Sold Summary

  • 11% Below List Price
  • 99 Days On Market

  Last Listing Agent Jason Minch William Raveis-New York LLC

  0 William Hill Rd, Chester, NY 12817
• 

  Est $944,000 Not Listed For Sale

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

  121 Conklingtown Rd, Chester, NY 10918

  121 Conklingtown Rd, Chester, NY 10918
• 

  

  

  /31

  $875,000

  • 3 Beds
  • 2.5 Baths
  • 2,302 Sq Ft

  2 Pine Hill Rd, Chester, NY 10918

  Listed on the National Register of Historic Places in the Sugar Loaf Historic District, this stunning Victorian is a Circa 1910 Sears Roebuck Kit Home (#118 The Clyde). Not only is this your dream home located in beautiful Sugar Loaf, NY, it is also zoned for extensive commercial use. Just a 1-minute walk to the quaint Sugar Loaf Arts & Crafts Village, cafes and Sugar Loaf Performing Arts Center.

  Debbie Walsh SHAHAR Management LLC

  2 Pine Hill Rd, Chester, NY 10918
• 

  $617,000 Sold May 19, 2025

  1301 Kings Hwy, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,676 Sq Ft
  • Built 1835

  Last Sold Summary

  • 10% Below List Price
  • $231/SF
  • 146 Days On Market

  Current Estimated Value $632,926

  Last Listing Agent Susan Walski Keller Williams Hudson Valley

  1301 Kings Hwy, Chester, NY 10918
• 

  Est $625,377 Not Listed For Sale

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

  79 Conklingtown Rd, Chester, NY 10918

  79 Conklingtown Rd, Chester, NY 10918
• 

  

  /78

  $699,900

  • Land
  • 337 Acres
  • $2,077 per Acre

  L 13.2 Friends Lake Rd, Chester, NY 12817

  2,200 feet of frontage along the Upper Hudson River, a wild, whitewater backcountry river, and immediate access to nearly 1,600 acres of State Forest Preserve, the Hudson River Woods & Wildwater property is the ''complete package'' of Adirondack property. With over 4,500 feet of road frontage (with electric) on Friends Lake Road, it's an ideal location for a camp, second home, or subdivision.

  John O'Donnell Timberland Realty

  L 13.2 Friends Lake Rd, Chester, NY 12817
• 

  $763,750 Sold Jun 20, 2025

  3 Woodridge Dr, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • Built 1995

  Last Sold Summary

  • 4% Below List Price
  • $306/SF
  • 69 Days On Market

  Current Estimated Value $774,213

  Last Listing Agent Gina Dudgeon Howard Hanna Rand Realty

  3 Woodridge Dr, Chester, NY 10918
• 

  Est $371,905 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 835 Sq Ft

  70 Conklingtown Rd, Chester, NY 10918

  70 Conklingtown Rd, Chester, NY 10918
• 

  

  /18

  $39,500

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

  22 Carriage Rd, Chester, NY

  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 steeper 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

  22 Carriage Rd, Chester, NY
• 

  $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 $375,648

  Last Listing Agent Christian Baez Keller Williams Hudson Valley

  19 Taurus Ave, Monroe, NY 10950
• 

  Est $549,302 Not Listed For Sale

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

  3976 Summerville Way, Chester, NY 10918

  3976 Summerville Way, Chester, NY 10918
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  $874,900

  • 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
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  /16

  $60,000 Sold Jun 12, 2025

  116 Carriage Knoll Rd, Chester, NY 12817

  • Land
  • 5.34 Acres
  • $11,236 per Acre

  Last Sold Summary

  • 4% Below List Price
  • 30 Days On Market

  Last Listing Agent Walter Swartz Gallo Realty ADK Inc

  116 Carriage Knoll Rd, Chester, NY 12817
• 

  Est $678,506 Not Listed For Sale

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

  3966 Summerville Way, Chester, NY 10918

  3966 Summerville Way, Chester, NY 10918
• 

  /2

  $324,000 Pending

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

  3 Hickory Ln, Monroe, NY 10950

  A spacious ranch style home offering incredible potential and plenty of living space. Features an open concept main level with a large living/dining area, updated flooring, and sliding doors leading to a generous rear deck. The renovated full bathroom adds a modern touch. Lower level includes multiple finished rooms, ideal for extra bedrooms, office space, or storage, needing some TLC. Set on a

  Lazar Schvimmer Blooming Realty

  3 Hickory Ln, Monroe, NY 10950
• 

  $285,000 Sold Mar 31, 2025

  101 Mountain Laurel Dr Unit 1A, Monroe, NY 10950

  • 2 Beds
  • 2.5 Baths
  • 1,344 Sq Ft
  • Built 1979

  Last Sold Summary

  • $212/SF
  • 57 Days On Market

  Current Estimated Value $303,354

  Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

  101 Mountain Laurel Dr Unit 1A, Monroe, NY 10950
• 

  Est $736,825 Not Listed For Sale

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

  1689 Kings Hwy, Chester, NY 10918

  1689 Kings Hwy, Chester, NY 10918
• 

  

  /24

  $345,000

  • 3 Beds
  • 1 Bath
  • 1,120 Sq Ft

  65 Hudson St, Chester, NY 10918

  A truly rare opportunity to secure over two acres of prime land in the highly desirable and rapidly appreciating town of Chester. This charming property isn't just a home; it's a foundation for your future and a strategic long-term investment. Set on a sprawling 2.1+ acre lot, this property offers the space and privacy that is simply unmatched in today's market. The current single-level structure

  Nikki Grzegorzewski Keller Williams Realty

  65 Hudson St, Chester, NY 10918
• 

  $530,000 Sold May 19, 2025

  3 Grant Dr, Monroe, NY 10950

  • 3 Beds
  • 2 Baths
  • 1,932 Sq Ft
  • Built 1989

  Last Sold Summary

  • 6% Above List Price
  • $274/SF
  • 21 Days On Market

  Current Estimated Value $540,869

  Last Listing Agent Rosalie Cook Weichert Realtors

  3 Grant Dr, Monroe, NY 10950
• 

  Est $703,455 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,504 Sq Ft

  272 Bull Mill Rd, Chester, NY 10918

  272 Bull Mill Rd, Chester, NY 10918
• 

  

  /45

  $499,900

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

  6 Vista Dr, Chester, NY 10918

  Stunning Chester Home with Pool, Pond & Private Backyard Oasis! Discover your own private retreat in this meticulously maintained 3-bedroom, 2.5-bath home in Chester. Perfectly positioned for privacy on a scenic lot featuring its own backyard pond, this property offers a rare combination of comfort and outdoor amenities. Step inside to a bright and airy main level where hardwood floors connect

  Christine Koenig Keller Williams Realty

  6 Vista Dr, Chester, NY 10918
• 

  $490,900 Sold Feb 13, 2025

  220 Glenmere Rd, Chester, NY 10918

  • 3 Beds
  • 1.5 Baths
  • 1,268 Sq Ft
  • Built 1972

  Last Sold Summary

  • $387/SF
  • 159 Days On Market

  Current Estimated Value $495,995

  Last Listing Agent Kathy Dawson Howard Hanna Rand Realty

  220 Glenmere Rd, Chester, NY 10918
• 

  Est $680,874 Not Listed For Sale

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

  71 Winding Trail, Chester, NY 10918

  71 Winding Trail, Chester, NY 10918
• 

  

  /27

  $129,000

  • Land
  • 13.33 Acres
  • $9,677 per Acre

  L9 Bird Pond Rd, Chester, NY 12853

  Private 13+ acres of gently sloping land just minutes from Gore Mountain. Roughed-in driveway/Road leading from Bird Pond Rd. Several nice building locations around the property. One house-site staked-out for reference. Possible views from higher on the property with some select clearing. Listing agent will provide one set of existing preliminary building plans for the future homeowner from

  Walter Swartz Gallo Realty ADK Inc

  L9 Bird Pond Rd, Chester, NY 12853
• 

  $869,000 Sold May 05, 2025

  46 Brookview Dr, Monroe, NY 10950

  • 5 Beds
  • 5 Baths
  • 4,200 Sq Ft
  • Built 1993

  Last Sold Summary

  • 3% Below List Price
  • $207/SF
  • 146 Days On Market

  Current Estimated Value $897,033

  Last Listing Agent David White Owner Entry.com

  46 Brookview Dr, Monroe, NY 10950
• 

  Est $793,151 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,923 Sq Ft

  11 Park Place, Chester, NY 10918

  11 Park Place, Chester, NY 10918
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  /48

  $1,100,000

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

  53 Odyssey Dr, Chester, NY 10918

  Welcome to an extraordinary 4,400+ square foot residence in the coveted Warwick School district, where luxury and lifestyle converge to create the ultimate entertainer’s dream. This meticulously maintained and thoughtfully updated home offers breathtaking panoramic views, inviting you to unwind in the serene front atrium or the sun-drenched sunroom at the rear. Step inside to discover a

  Hilary Ryan Goldman Howard Hanna Rand Realty

  53 Odyssey Dr, Chester, NY 10918
• 

  $185,000 Sold Jan 16, 2025

  115 Green Meadows Way, Chester, NY 10918

  • 1 Bed
  • 1.5 Baths
  • 747 Sq Ft
  • Built 1987

  Last Sold Summary

  • 10% Above List Price
  • $248/SF
  • 13 Days On Market

  Current Estimated Value $193,498

  Last Listing Agent Guy Cusumano Howard Hanna Rand Realty

  115 Green Meadows Way, Chester, NY 10918
• 

  Est $887,294 Not Listed For Sale

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

  2 Park Place, Chester, NY 10918

  2 Park Place, Chester, NY 10918
• 

  

  /20

  $599,000 Pending

  • 3 Beds
  • 1.5 Baths

  4 Greycourt Rd, Chester, NY 10918

  Magnificent sprawling ranch situated on a park like setting with 2.80 acres with mature landscaping. This home features a spacious 2014 renovated EIK for entertaining with soft close cabinets, granite countertops, stainless steel appliances and an island cook top. Kitchen leads to an open concept large living /dining room combo with a large bay window for natural light with newly refinished

  Scott Loyer Coldwell Banker American Homes

  4 Greycourt Rd, Chester, NY 10918
• 

  $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 $826,414

  Last Listing Agent David Hopstein eRealty Advisors, Inc

  10 Spectrum Dr, Chester, NY 10918
• 

  Est $613,626 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,021 Sq Ft

  243 Bull Mill Rd, Chester, NY 10918

  243 Bull Mill Rd, Chester, NY 10918
• 

  

  /4

  $479,900

  • Land
  • 8.38 Acres
  • $57,250 per Acre

  30 Harding Way, Chester, NY 10950

  Opportunity is knocking on the door for all builders/investors in the Town Of Chester, Monroe - Woodbury School District. You buy 2 lots for the price of one. 30 Harding Way is SOLD TOGETHER with the lot next to it of 8.2 acres which is located in Section 15, Block 1, Lot 32. Subdivision potential.

  Ida Payne Keller Williams Realty

  30 Harding Way, Chester, NY 10950
• 

  $607,700 Sold Apr 29, 2025

  142 Laroe Rd, Chester, NY 10918

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

  Last Sold Summary

  • 3% Below List Price
  • $180/SF
  • 107 Days On Market

  Current Estimated Value $655,868

  Last Listing Agent Peter Persaud HomeSmart Homes & Estates

  142 Laroe Rd, Chester, NY 10918
• 

  Est $551,004 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,944 Sq Ft

  119 Booth Rd, Chester, NY 10918

  119 Booth Rd, Chester, NY 10918
• 

  

  /20

  $525,000 Pending

  • 4 Beds
  • 1.5 Baths
  • 1,792 Sq Ft

  32 Poplar Dr, Monroe, NY 10950

  GREAT house! If you are looking for move in ready this is IT!!! New kitchen and baths! Either new floors or redone hardwood. Freshly painted. Beautiful paver walkway! New Boiler 2023, Water Heater 2023, Ductless 2022, Roof 10 years old.

  Ann Marie Hahr Keller Williams Realty

  32 Poplar Dr, Monroe, NY 10950
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  $189,500 Sold Jun 02, 2025

  L47 Cobble Creek Rd, Chester, NY 12853

  • Land
  • 97.28 Acres
  • $1,948 per Acre

  Last Sold Summary

  • 5% Below List Price
  • 11 Days On Market

  Last Listing Agent Sara Gallipo-Sammis Century 21 - Adirondacks

  L47 Cobble Creek Rd, Chester, NY 12853
• 

  Est $620,317 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,130 Sq Ft

  6 Reilly Rd, Chester, NY 10918

  6 Reilly Rd, Chester, NY 10918
• 

  /2

  $500,000

  • Land
  • 0.83 Acre
  • $603,355 per Acre

  0 Main St, Chester, NY 10918

  Open commercial lot directly behind the existing Cumberland Farms and just to the east of the former Brookside carwash. Good use may be for a parking lot for a building built on 42 Brookside.

  Claude Brischoux Keller Williams Realty

  0 Main St, Chester, NY 10918
• 

  $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 $545,287

  Last Listing Agent Courtney Tablante Keller Williams Realty

  13 Tulip Ln Unit 4, Monroe, NY 10950

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