Chester, NY Homes

• 

  Est $658,738 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
• 

  

  

  /41

  $425,000 Pending

  • 4 Beds
  • 1.5 Baths
  • 1,386 Sq Ft

  47 Greycourt Ave, Chester, NY 10918

  Classic farmhouse feel with contemporary updates on a generous 1.3-acre lot, with this home you get it all! This 3/4bedroom, 1.5-bath home combines classic warmth with modern comforts, including a kitchen featuring granite countertops, hardwood flooring and a spacious island perfect for prep and entertaining. along with a huge sunken living room with recessed lighting and a pellet stove to save

  Pedro Garcia Curasi Realty, Inc.

  47 Greycourt Ave, Chester, NY 10918
• 

  $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 $436,042

  Last Listing Agent Jason Dillon eXp Realty

  18 Academy Ave, Chester, NY 10918
• 

  Est $634,020 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
• 

  

  /2

  $669,000

  • 3 Beds
  • 1.5 Baths
  • 1,816 Sq Ft

  101 Oxford Rd, Chester, NY 10918

  This nice quiet house is a great place to call home. With almost 11 acres of land, there's a lot of space to enjoy activities and outdoor fun. The first floor of the house offers a nice layout with big living room, family room, kitchen, dining room, and a half bath. and a washer and dryer room . Bedrooms are nice and big making it very comfortable . The house will need some TLC and will need

  Nathan Landau Loop Realty Inc

  101 Oxford Rd, 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 $853,156

  Last Listing Agent Catherine Delf KW Platform

  16 Heritage Ln, Chester, NY 12817
• 

  Est $591,107 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,910 Sq Ft

  38 Rebecca Rd, Chester, NY 10918

  38 Rebecca Rd, Chester, NY 10918
• 

  

  /11

  $349,999

  • Land
  • 4.9 Acres
  • $71,428 per Acre

  8 Camelback Rd, Chester, NY 10918

  Nestled at the end of a private cul-de-sac, this 5 acre homesite offers breathtaking mountain and valley views in the sought-after Bull Mill Road area of Monroe/Chester, NY. The property’s gentle slopes create the perfect opportunity for a walkout lower level, allowing you to capture spectacular sunsets. This shovel-ready, fully approved, and engineered building lot features Belgian block

  James Feldhaus eXp Realty

  8 Camelback Rd, Chester, NY 10918
• 

  $550,000 Sold Apr 23, 2025

  16 Fernglade Ct, Chester, NY 10918

  • 4 Beds
  • 3 Baths
  • 3,327 Sq Ft
  • Built 1973

  Last Sold Summary

  • 13% Above List Price
  • $165/SF
  • 12 Days On Market

  Current Estimated Value $644,581

  Last Listing Agent Kim Chiapperino RE/MAX Benchmark Realty Group

  16 Fernglade Ct, Chester, NY 10918
• 

  Est $615,715 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,411 Sq Ft

  32 Rebecca Rd, Chester, NY 10918

  32 Rebecca Rd, Chester, NY 10918
• 

  

  /12

  $39,500

  • Land
  • 1.82 Acres
  • $21,703 per Acre

  34 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

  34 Carriage Rd, Chester, NY
• 

  

  /3

  $58,450 Sold Feb 06, 2025

  L26 Marina Rd Unit Subdivision Lot 3, Chester, NY 12817

  • Land
  • 0.89 Acre
  • $65,674 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 16 Days On Market

  Last Listing Agent John Palermo John R. Palermo

  L26 Marina Rd Unit Subdivision Lot 3, Chester, NY 12817
• 

  Est $668,638 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,861 Sq Ft

  8 Valerie Dr, Chester, NY 10918

  8 Valerie Dr, Chester, NY 10918
• 

  

  /20

  $68,900

  • Land
  • 3.26 Acres
  • $21,135 per Acre

  98 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

  98 Carriage Knoll Rd, Chester, NY 12817
• 

  $602,000 Sold Feb 13, 2025

  19 Mount Ridge Ct, Monroe, NY 10950

  • 4 Beds
  • 2.5 Baths
  • 2,698 Sq Ft
  • Built 2000

  Last Sold Summary

  • 9% Above List Price
  • $223/SF
  • 15 Days On Market

  Current Estimated Value $624,462

  Last Listing Agent Christian Baez Keller Williams Hudson Valley

  19 Mount Ridge Ct, Monroe, NY 10950
• 

  Est $684,036 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,904 Sq Ft

  3 Stacey Ln, Chester, NY 10918

  3 Stacey Ln, Chester, NY 10918
• 

  

  /30

  $725,000

  • 5 Beds
  • 2.5 Baths
  • 3,124 Sq Ft

  9 Country Woods Dr, Chester, NY 10918

  Thoughtfully repositioned with a nearly $15,000 price adjustment makes this Country Woods colonial an unbeatable value! Now priced to allow for updates while securing a prime location, generous living space, a beautiful setting, and room to add your personal style. Country Woods is one of Chester’s most sought-after neighborhoods. This handsome Colonial sits on 1.7 landscaped acres and offers

  Kimberly Starks Howard Hanna Rand Realty

  9 Country Woods Dr, Chester, NY 10918
• 

  $720,000 Sold Feb 05, 2025

  14 Country Woods Dr, Chester, NY 10918

  • 5 Beds
  • 3.5 Baths
  • 3,955 Sq Ft
  • Built 2002

  Last Sold Summary

  • 3% Below List Price
  • $182/SF
  • 62 Days On Market

  Current Estimated Value $776,963

  Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

  14 Country Woods Dr, Chester, NY 10918
• 

  Est $554,509 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,080 Sq Ft

  56 Goosepond Mountain Rd, Chester, NY 10918

  56 Goosepond Mountain Rd, Chester, NY 10918
• 

  /2

  $350,000

  • Land
  • 2 Acres
  • $175,000 per Acre

  220 Oxford Rd, Chester, NY 10918

  A rare opportunity in Blooming Grove! This beautiful and flat 2-acre property offers endless potential in a calm and peaceful setting with a road frontage. Conveniently located just minutes from Prospect Garden, the land sits within the Monroe-Woodbury School District. With easy access to permits, this property is ideal for building your dream home or future investment. The neighborhood holds

  Chaim Weiss Exit Realty Venture

  220 Oxford Rd, Chester, NY 10918
• 

  $565,000 Sold Jan 23, 2025

  86 Brimstone Mountain Rd, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,817 Sq Ft
  • Built 1980

  Last Sold Summary

  • 4% Above List Price
  • $311/SF
  • 91 Days On Market

  Current Estimated Value $602,084

  Last Listing Agent Kimberly Starks Howard Hanna Rand Realty

  86 Brimstone Mountain Rd, Chester, NY 10918
• 

  Est $751,507 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,740 Sq Ft

  149 Creamery Pond Rd, Chester, NY 10918

  149 Creamery Pond Rd, Chester, NY 10918
• 

  

  /49

  $534,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,946 Sq Ft

  80 Pewter Cir, Chester, NY 10918

  Welcome to the Villas at Sugar Loaf — an unbeatable location that rarely sees homes come on the market! Just half a mile from the charming hamlet of Sugar Loaf, this beautifully maintained move-in ready townhome is in the highly sought-after Warwick School District. With easy access to major highways and train stations, this home is ideal for commuters. Inside, you’ll love the bright, open floor

  Julie Klein BHG Real Estate Green Team

  80 Pewter Cir, Chester, NY 10918
• 

  $960,000 Sold Jun 05, 2025

  53 Gibson Hill Rd, Chester, NY 10918

  • 5 Beds
  • 4 Baths
  • 5,312 Sq Ft
  • Built 2010

  Last Sold Summary

  • 4% Below List Price
  • $181/SF
  • 45 Days On Market

  Current Estimated Value $1,005,421

  Last Listing Agent Roxanne Hartman Timothy W. Kramer

  53 Gibson Hill Rd, Chester, NY 10918
• 

  Est $700,191 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,436 Sq Ft

  169 Creamery Pond Rd, Chester, NY 10918

  169 Creamery Pond Rd, Chester, NY 10918
• 

  

  /25

  $39,000

  • Land
  • 2.48 Acres
  • $15,726 per Acre

  37 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

  37 Carriage Rd, Chester, NY
• 

  $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 $386,408

  Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

  3816 Whispering Hills, Chester, NY 10918
• 

  Est $559,541 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,136 Sq Ft

  7 Mount Ridge Ct, Monroe, NY 10950

  7 Mount Ridge Ct, Monroe, NY 10950
• 

  

  /50

  $650,000

  • 5 Beds
  • 3.5 Baths
  • 3,617 Sq Ft

  65 Oxford Springs Rd, Chester, NY 10918

  Welcome to 65 Oxford Springs Road, Chester, NY a custom-built Country Contemporary set on a private, 2.3-acre hilltop. This property offers the perfect mix of privacy, space, and convenience, all just minutes from the NYS Thruway, local state parks, and about 50 minutes from NYC. Inside, the home features a bright, open floor plan with plenty of natural light. You’ll find rich hardwood floors,

  Ammar Iqbal eXp Realty

  65 Oxford Springs Rd, Chester, NY 10918
• 

  $370,000 Sold Dec 31, 2024

  22 Trotting Dr, Chester, NY 10918

  • 3 Beds
  • 1 Bath
  • 1,024 Sq Ft
  • Built 1968

  Last Sold Summary

  • $361/SF
  • 29 Days On Market

  Current Estimated Value $379,379

  Last Listing Agent Diane Blanton Howard Hanna Rand Realty

  22 Trotting Dr, Chester, NY 10918
• 

  Est $402,289 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,694 Sq Ft

  465 Meri Ln, Monroe, NY 10950

  465 Meri Ln, Monroe, NY 10950
• 

  

  /49

  $1,500,000

  206 Greycourt Rd Unit 190, Chester, NY 10918

  **Endless Opportunities Await on This Rare 3.2-Acre Property!** ZONED COMMMERCIAL INDUSTRIAL USEFor the first time in over 50 years, this prime piece of real estate is hitting the market! Nestled right off Route 17 with unbeatable exposure, this unique 3.2-acre property offers **unlimited potential** for investors, developers, or those looking for a special place to call home.

  Susan McMullen eXp Realty

  206 Greycourt Rd Unit 190, Chester, NY 10918
• 

  $460,000 Sold Mar 24, 2025

  14 Mari Rd, Chester, NY 10918

  • 3 Beds
  • 1.5 Baths
  • 1,926 Sq Ft
  • Built 1970

  Last Sold Summary

  • 10% Above List Price
  • $239/SF
  • 12 Days On Market

  Current Estimated Value $482,354

  Last Listing Agent Martha Randazzo Howard Hanna Rand Realty

  14 Mari Rd, Chester, NY 10918
• 

  Est $388,622 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,694 Sq Ft

  463 Meri Ln, Monroe, NY 10950

  463 Meri Ln, Monroe, NY 10950
• 

  

  /3

  $75,000

  • Land
  • 12 Acres
  • $6,250 per Acre

  L62.2 Moffitt Rd, Chester, NY 12817

  12-acre parcel offering beautiful terrain and privacy, yet on a town-maintained road. Plenty of options for a home setting. A very desirable property for your future home construction. Only 15 minutes to Gore Mountain Ski Area, 3 miles to Loon Lake and within a mile of the Hudson River. A wonderful opportunity to enjoy the Adirondack experience. $75,000

  Carol Monroe Najer Realty

  L62.2 Moffitt Rd, 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 $650,375

  Last Listing Agent Karen Gauvin Our House Real Estate Group

  40 Mountainside Dr, Chester, NY 10918
• 

  Est $397,003 Not Listed For Sale

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

  321 Heritage Ln, Monroe, NY 10950

  321 Heritage Ln, Monroe, NY 10950
• 

  

  /45

  $1,395,000

  • 4 Beds
  • 2.5 Baths
  • 3,866 Sq Ft

  2948 State Route 94, Chester, NY 10918

  Set atop a gentle hill with sweeping eastern views of Round Hill and Schunnemunk Ridge, this pristine 1860 farmhouse blends preserved historic character with thoughtful modern updates. Originally part of the Sears family dairy pasture, the 3,866 sq ft home has been meticulously maintained and features original wide-plank hardwood floors, a striking hand-carved banister, five fireplaces with

  Elizabeth Broderick Tuxedo Hudson Realty Corp

  2948 State Route 94, Chester, NY 10918
• 

  $565,000 Sold Feb 27, 2025

  9 Laroc Rd, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,810 Sq Ft
  • Built 1973

  Last Sold Summary

  • 1% Above List Price
  • $312/SF
  • 11 Days On Market

  Current Estimated Value $592,787

  Last Listing Agent Nathen Singer MK Realty Inc

  9 Laroc Rd, Chester, NY 10918
• 

  Est $397,014 Not Listed For Sale

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

  301 Heritage Ln, Monroe, NY 10950

  301 Heritage Ln, Monroe, NY 10950

Showing Results 161 - 200, Page 5 of 18