Chester, NY Homes

• 

  Est $362,456 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 835 Sq Ft

  70 Conklingtown Rd, Chester, NY 10918

  70 Conklingtown Rd, Chester, NY 10918
• 

  

  

  /19

  $74,900

  • 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
• 

  $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 $775,477

  Last Listing Agent Gina Dudgeon Howard Hanna Rand Realty

  3 Woodridge Dr, Chester, NY 10918
• 

  Est $538,238 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
• 

  

  

  /3

  $199,000 Pending

  • Land
  • 1.85 Acres
  • $107,568 per Acre

  0 Renies Rd, Chester, NY 10918

  Seize the opportunity to own this serene, buildable lot nestled in a quiet, desirable location. Perfect for your dream home. This parcel offers privacy, natural beauty, and close to everything! Convenient access yet tucked away for peace and quiet. Don’t miss out—schedule your visit today!

  Kristie Jacques Century 21 Full Service Realty

  0 Renies Rd, Chester, NY 10918
• 

  $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 $378,688

  Last Listing Agent Christian Baez Keller Williams Hudson Valley

  19 Taurus Ave, Monroe, NY 10950
• 

  Est $698,231 Not Listed For Sale

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

  3966 Summerville Way, Chester, NY 10918

  3966 Summerville Way, Chester, NY 10918
• 

  

  /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
• 

  

  /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 $765,977 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
• 

  

  /38

  $449,000

  • 3 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  71 Greycourt Rd, Chester, NY 10918

  Discover comfort, privacy, and convenience in this beautifully maintained home set on a 2 acre property. Located in a peaceful area, this residence offers a warm and inviting layout with a nicely sized kitchen, three comfortable bedrooms, and two well kept bathrooms.The outdoors is offering a stunning fenced backyard, lots of playground space for entertainment. Minutes to all major highways

  Lazar Schvimmer Blooming Realty

  71 Greycourt Rd, Chester, NY 10918
• 

  $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 $304,452

  Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

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

  Est $577,220 Not Listed For Sale

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

  128 Booth Rd, Chester, NY 10918

  128 Booth Rd, Chester, NY 10918
• 

  

  /11

  $261,250

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

  503 Mountain Laurel Dr, Monroe, NY 10950

  Two story center unit with full basement located in Windridge community. Primary bedroom has large sitting area which can be used as home office. Sliders to rear patio with lake views!! Large living and dining area. Beautiful complex with mountain views.

  Margaret Galatro ARC Realty 1 in Sales

  503 Mountain Laurel Dr, Monroe, NY 10950
• 

  $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 $541,692

  Last Listing Agent Rosalie Cook Weichert Realtors

  3 Grant Dr, Monroe, NY 10950
• 

  Est $707,884 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
• 

  

  /23

  $430,000

  • 3 Beds
  • 1 Bath
  • 1,561 Sq Ft

  33 Meadow Ave, Chester, NY 10918

  One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ranch offers hardwood flooring throughout main living area & newly update kitchen and bath. Kitchen with plenty of cabinet & counter space.Entertain or BBQ on your private private deck. Plenty of parking in your 1 car garage. Walk

  Ernie Acampora River Realty Services, Inc.

  33 Meadow Ave, 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 $491,753

  Last Listing Agent Kathy Dawson Howard Hanna Rand Realty

  220 Glenmere Rd, Chester, NY 10918
• 

  Est $698,866 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
• 

  

  /47

  $525,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,928 Sq Ft

  219 Bull Mill Rd, Chester, NY 10918

  Welcome to your private oasis in Chester, NY!Immaculately maintained and move-in ready, this beautiful 4-bedroom, 2-full-bath ranch sits on one acre of level, fenced-in land offering privacy, comfort, and endless possibilities. Pride of ownership rings through in every detail. A stunning covered porch graces the front of the property and provides an inviting space to savor your morning cup of

  Claudia Lepore Keller Williams Realty

  219 Bull Mill Rd, Chester, NY 10918
• 

  $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 $986,921

  Last Listing Agent David White Owner Entry.com

  46 Brookview Dr, Monroe, NY 10950
• 

  Est $799,951 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
• 

  

  /7

  $49,500

  • Land
  • 3.36 Acres
  • $14,732 per Acre

  20 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

  20 Carriage Knolls Rd, Chester, NY 12817
• 

  $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 $831,565

  Last Listing Agent David Hopstein eRealty Advisors, Inc

  10 Spectrum Dr, Chester, NY 10918
• 

  Est $877,080 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

  $169,500 Pending

  • Land
  • 22.6 Acres
  • $7,500 per Acre

  L2 Friends Lake Rd, Chester, NY 12817

  Seller financing now available with decent deposit and good credit. Previously approved 4-lot subdivision with beach rights to Murphy Beach on Friends Lake. 8.6 acre lot, 7.5 acre lot, 3.2 acre lot, and a 3 acre lot. Rough house and septic locations have been approved. (reference survey map) Possible views from the upper areas of the property with some select clearing. Make arrangements to walk

  Walter Swartz Gallo Realty ADK Inc

  L2 Friends Lake Rd, Chester, NY 12817
• 

  $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 $651,279

  Last Listing Agent Peter Persaud HomeSmart Homes & Estates

  142 Laroe Rd, Chester, NY 10918
• 

  Est $634,745 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
• 

  

  /28

  $1,498,888

  • 4 Beds
  • 4 Baths
  • 7,308 Sq Ft

  37 Main St, Chester, NY 10918

  Prime Investment Opportunity in the Heart of Chester Village – 37-39 Main Street & 9 Bank Street Nestled in the charming and historic Village of Chester, this fully updated mixed-use property presents an exceptional investment opportunity. Originally built in 1935, this rustic yet modernized building seamlessly blends timeless character with contemporary upgrades. The property features:•

  James Feldhaus eXp Realty

  37 Main St, Chester, NY 10918
• 

  

  /12

  $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 $554,884 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
• 

  

  /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
• 

  $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
• 

  Est $620,181 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

  $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
• 

  $420,000 Sold Mar 14, 2025

  18 Academy Ave, Chester, NY 10918

  • 1,371 Sq Ft
  • Built 1900

  Last Sold Summary

  • 1% Below List Price
  • $306/SF
  • 52 Days On Market

  Current Estimated Value $436,971

  Last Listing Agent Jason Dillon eXp Realty

  18 Academy Ave, Chester, NY 10918
• 

  Est $669,860 Not Listed For Sale

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

  61 Nancy Ln, Chester, NY 10918

  61 Nancy Ln, Chester, NY 10918
• 

  

  /24

  $345,000 Pending

  • 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
• 

  

  /51

  $810,000 Sold Mar 11, 2025

  16 Heritage Ln, Chester, NY 12817

  • 5 Beds
  • 5 Baths
  • 5,000 Sq Ft
  • Built 2006

  Last Sold Summary

  • 7% Below List Price
  • $162/SF
  • 25 Days On Market

  Current Estimated Value $858,994

  Last Listing Agent Catherine Delf KW Platform

  16 Heritage Ln, Chester, NY 12817
• 

  Est $612,050 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,768 Sq Ft

  88 Nancy Ln, Chester, NY 10918

  88 Nancy Ln, Chester, NY 10918

Showing Results 121 - 160, Page 4 of 18