Chester, NY Homes

• 

  $725,000

  Sold May 27, 2026

  16 Oxford Springs Rd, Chester, NY 10918

  • 3 Beds
  • 3 Baths
  • 2,870 Sq Ft
  • Built 1988

  Last Sold Summary

  • 7% Below List Price
  • $253/SF
  • 117 Days On Market

  Current Estimated Value $716,894

  Last Listing Agent Jennifer Gold RE/MAX Benchmark Realty Group

  16 Oxford Springs Rd, Chester, NY 10918
• 

  Est $528,964

  Not Listed For Sale

  14 Twin Brooks Dr, Chester, NY 10918

  • 4 Beds
  • 1.5 Baths
  • 1,692 Sq Ft
  • Built 1968

  14 Twin Brooks Dr, Chester, NY 10918

  Last Sold Summary

  • 50 Days On Market

  Last Listing Agent Layla Rose Boyles Century 21 Realty Center
• 

  

  

  /16

  $325,000

  $25K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,504 Sq Ft

  151 Main St, Chester, NY 10918

  A Diamond in the Rough! Calling all handymen to bring this Village Charmer back to its' original glory. This home has a large Living Room with a cozy alcove, spacious Dining Room and large Kitchen with sliders to a rear deck and yard. It also features 4 nice sized bedrooms. With a "little love and vision" this home could be a lovely family home! Could be a wonderful opportunity for investors!

  Eveline White Hudson Valley Griffith

  151 Main St, Chester, NY 10918
• 

  $465,000

  Sold Jun 18, 2026

  40 Poplar Dr, Monroe, NY 10950

  • 3 Beds
  • 2 Baths
  • 1,108 Sq Ft
  • Built 1972

  Last Sold Summary

  • 9% Above List Price
  • $420/SF
  • 20 Days On Market

  Current Estimated Value $441,780

  Last Listing Agent Richard Froehlich RE/MAX Benchmark Realty Group

  40 Poplar Dr, Monroe, NY 10950
• 

  Est $614,920

  Not Listed For Sale

  73 Dug Rd, Chester, NY 10918

  • 5 Beds
  • 4 Baths
  • 2,554 Sq Ft
  • Built 1971

  73 Dug Rd, Chester, NY 10918

  Last Sold Summary

  • 69 Days On Market

  Last Listing Agent David Kraus MK Realty Inc
• 

  

  /35

  $524,900

  Pending

  • 4 Beds
  • 2 Baths
  • 2,076 Sq Ft

  85 Surrey Rd, Chester, NY 10918

  Welcome to 85 Surrey Road in Chester, NY, a beautifully updated home that blends modern upgrades with timeless comfort in the heart of the Hudson Valley. This move-in-ready property offers everything today’s buyers are searching for—energy efficiency, stylish finishes, and exceptional indoor-outdoor living.Step inside to discover a fabulously updated kitchen, designed for both everyday living

  Rebecca Matta-Candela Keller Williams Realty

  85 Surrey Rd, Chester, NY 10918
• 

  $365,000

  Sold Nov 14, 2025

  2409 Whispering Hills, Chester, NY 10918

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

  Last Sold Summary

  • 2% Above List Price
  • $274/SF
  • 26 Days On Market

  Current Estimated Value $367,013

  Last Listing Agent Linda Clark Hudson Valley Griffith

  2409 Whispering Hills, Chester, NY 10918
• 

  Est $484,670

  Not Listed For Sale

  559 Laroe Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 1,900 Sq Ft
  • Built 1970

  559 Laroe Rd, Chester, NY 10918

  Last Sold Summary

  • 239 Days On Market

  Last Listing Agent Eliezer Safdie Sage Realty Center LLC
• 

  

  /36

  $419,000

  Pending

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

  332 Heritage Ln, Monroe, NY 10950

  Spacious and well-maintained 3BR/2.5BA townhouse in desirable Windridge community. Features include updated laminate hardwood flooring, fireplace, eat-in kitchen, stainless steel appliances, private balcony off primary bedroom, sliding glass doors to private patio, attached 1-car garage with storage loft, and pull-down attic access. Community amenities include pool, clubhouse, and park.

  Martin Remo RE/MAX Prime Properties

  332 Heritage Ln, Monroe, NY 10950
• 

  $460,000

  Sold Aug 28, 2025

  22 Able Noble Dr, Chester, NY 10918

  • 4 Beds
  • 2 Baths
  • 1,770 Sq Ft
  • Built 1968

  Last Sold Summary

  • 8% Below List Price
  • $260/SF
  • 40 Days On Market

  Current Estimated Value $472,547

  Last Listing Agent Robin Kelly Picture It Sold, LLC

  22 Able Noble Dr, Chester, NY 10918
• 

  Est $514,993

  Not Listed For Sale

  4 Stevens Place, Chester, NY 10918

  • 3 Beds
  • 1.5 Baths
  • 1,882 Sq Ft
  • Built 1969

  4 Stevens Place, Chester, NY 10918

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Joan Wortmann Weichert Realtors
• 

  

  /14

  $129,000

  $30K PRICE DROP

  • Land
  • 20,473 Sq Ft
  • $274,468 per Acre

  L31 Clarkson Rd, Chester, NY 12817

  Build Your Adirondack Getaway on Loon Lake!Enjoy beach rights on beautiful Loon Lake with this just-under-half-acre lot, the perfect spot to create your own year-round retreat or seasonal escape. Whether you dream of summer days by the water, paddling and swimming, or cozy winter weekends in the mountains, this property offers an ideal starting point for your Adirondack lifestyle.

  Brooke Clark Four Seasons Sotheby's International Realty

  L31 Clarkson Rd, Chester, NY 12817
• 

  $350,000

  Sold Feb 02, 2026

  264 Heritage Ln, Monroe, NY 10950

  • 3 Beds
  • 1.5 Baths
  • 1,376 Sq Ft
  • Built 1988

  Last Sold Summary

  • $254/SF
  • 98 Days On Market

  Current Estimated Value $353,914

  Last Listing Agent Frank Golio Howard Hanna Rand Realty

  264 Heritage Ln, Monroe, NY 10950
• 

  Est $627,109

  Not Listed For Sale

  46 Ayr Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,784 Sq Ft
  • Built 1971

  46 Ayr Rd, Chester, NY 10918

  Last Sold Summary

  • 70 Days On Market

  Last Listing Agent Eliezer Safdie Sage Realty Center LLC
• 

  

  /44

  $549,000

  $31K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,112 Sq Ft

  150 Lake Region Blvd, Monroe, NY 10950

  Welcome to 150 Lake Region Blvd, a beautifully maintained home in Monroe’s sought-after Lake Region / Walton Park community. Step inside to warm hardwood floors and a thoughtfully designed layout that feels both inviting and functional. The main living spaces flow effortlessly, creating an ideal setting for everyday living and entertaining. Offering 4 spacious bedrooms and 3 full bathrooms, the

  Pete Wolven Hudson Valley Home Connection

  150 Lake Region Blvd, Monroe, NY 10950
• 

  $740,000

  Sold Nov 21, 2025

  48 Brennan Ct, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 3,063 Sq Ft
  • Built 2006

  Last Sold Summary

  • 4% Below List Price
  • $242/SF
  • 29 Days On Market

  Current Estimated Value $750,207

  Last Listing Agent Claude Brischoux Keller Williams Realty

  48 Brennan Ct, Chester, NY 10918
• 

  Est $539,939

  Not Listed For Sale

  16 Ayr Rd, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,716 Sq Ft
  • Built 1972

  16 Ayr Rd, Chester, NY 10918

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent Luanne McGann Century 21 Full Service Realty
• 

  

  /29

  $549,999

  • 4 Beds
  • 2.5 Baths
  • 2,098 Sq Ft

  7 Lakeview Dr, Chester, NY 10918

  This charming updated 4-bedroom beauty in the Warwick School district offers a private and quiet setting featuring an above ground pool surrounded by a freshly painted deck just 3 minutes from Sugar Loaf Arts and Crafts Village. Its' kitchen has been upgraded boasting stainless steel appliances, granite countertops, and cherrywood cabinetry with undermount lighting and a wine/ beverage cooler.

  Sheyla Falesto Howard Hanna Rand Realty

  7 Lakeview Dr, Chester, NY 10918
• 

  

  /31

  $55,000

  Sold May 12, 2026

  L7 Macglashan Ln, Chester, NY 12817

  • Land
  • 5.42 Acres
  • $10,148 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 130 Days On Market

  Current Estimated Value $47,500

  Last Listing Agent Walter Swartz Gallo Realty ADK Inc

  L7 Macglashan Ln, Chester, NY 12817
• 

  Est $435,275

  Not Listed For Sale

  13 Mari Rd, Chester, NY 10918

  • 3 Beds
  • 1.5 Baths
  • 1,358 Sq Ft
  • Built 1970

  13 Mari Rd, Chester, NY 10918

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Debbie Goldstein Howard Hanna Rand Realty
• 

  

  /50

  $1,725,000

  • 4 Beds
  • 2.5 Baths
  • 3,348 Sq Ft

  20 Goshen Rd, Chester, NY 10918

  THE ULTIMATE HUDSON VALLEY LEGACY ESTATE | 53 ACRES OF UNMATCHED POTENTIAL Rarely does a property emerge that perfectly balances refined luxury living with raw, untapped opportunity. Nestled in the heart of scenic Chester, New York, 20 Goshen Road offers an expansive 53-acre canvas designed for the visionary. Whether you envision a world-class equestrian facility, a high-potential residential

  Ramanjit Dhanoa eXp Realty

  20 Goshen Rd, Chester, NY 10918
• 

  $330,000

  Sold Aug 15, 2025

  4503 Whispering Hills, Chester, NY 10918

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

  Last Sold Summary

  • 12% Below List Price
  • $248/SF
  • 142 Days On Market

  Current Estimated Value $342,719

  Last Listing Agent Richard Baxter Keller Williams Realty

  4503 Whispering Hills, Chester, NY 10918
• 

  Est $481,178

  Not Listed For Sale

  14 Mari Rd, Chester, NY 10918

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

  14 Mari Rd, Chester, NY 10918

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Martha Randazzo Howard Hanna Rand Realty
• 

  

  /13

  $599,900

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,583 Sq Ft

  50 Hambletonian Ave, Chester, NY 10918

  Located in the heart of the Village of Chester, this beautifully updated home offers the rare combination of modern comfort, privacy, and convenience. Just steps from Chester Academy and the Heritage Trail, this property provides easy access to walking, biking, running, local events, and community amenities while offering the peaceful retreat of your own private acreage. Set on 4 private acres,

  Derek Greene Greene Realty Group

  50 Hambletonian Ave, Chester, NY 10918
• 

  $450,000

  Sold Aug 04, 2026

  5 Roggia Rd, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,882 Sq Ft
  • Built 1951

  Last Sold Summary

  • $239/SF
  • 31 Days On Market

  Current Estimated Value $445,012

  Last Listing Agent Nazma Sooknanan Nazma Real Estate LLC

  5 Roggia Rd, Chester, NY 10918
• 

  Est $470,942

  Not Listed For Sale

  12 Mari Rd, Chester, NY 10918

  • 4 Beds
  • 1.5 Baths
  • 1,842 Sq Ft
  • Built 1970

  12 Mari Rd, Chester, NY 10918

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Ryan Degnan Howard Hanna Rand Realty
• 

  

  /35

  $999,999

  • 5 Beds
  • 2.5 Baths
  • 4,772 Sq Ft

  2 Garnett Hill Rd, Chester, NY 10918

  A Private Suburban Retreat on Prestigious Garnet Hill. This Center Hall Colonial offers an exceptional residence- refined suburban living with the space, privacy, and sophistication sought by discerning buyers—just about an hour from Manhattan. Positioned on a beautifully landscaped 3+ acre property, the home features approximately over 4,700 square feet of elegant living space, offering 5

  Rachel Baruchov Platinum Realty Associates

  2 Garnett Hill Rd, Chester, NY 10918
• 

  $375,000

  Sold Dec 11, 2025

  4309 Whispering Hills Dr, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,355 Sq Ft
  • Built 1989

  Last Sold Summary

  • $277/SF
  • 27 Days On Market

  Current Estimated Value $378,329

  Last Listing Agent Sean Israelski Howard Hanna Rand Realty

  4309 Whispering Hills Dr, Chester, NY 10918
• 

  Est $513,681

  Not Listed For Sale

  62 Surrey Rd, Chester, NY 10918

  • 4 Beds
  • 1.5 Baths
  • 1,872 Sq Ft
  • Built 1968

  62 Surrey Rd, Chester, NY 10918

  Last Sold Summary

  • 37 Days On Market

  Last Listing Agent Valerie Quinn Keller Williams Realty
• 

  

  /49

  $699,995

  $25K PRICE DROP

  • 6 Beds
  • 3.5 Baths
  • 4,204 Sq Ft

  487 Black Meadow Rd, Chester, NY 10918

  A Landmark Farmhouse with a Story to Tell.Standing proudly since 1872, this historic Colonial farmhouse is one of the very first homes built on Black Meadow Road and remains a meaningful piece of Chester’s agricultural past. Once surrounded by hundreds of acres of open farmland and dairy cows, the home still carries the soul of a working farm while offering the comforts of modern living. With

  Dominic Santagato Joseph Baratta Company Realty

  487 Black Meadow Rd, Chester, NY 10918
• 

  $299,000

  Sold Apr 07, 2026

  3120 Whispering Hills, Chester, NY 10918

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft
  • Built 1987

  Last Sold Summary

  • 4% Below List Price
  • $279/SF
  • 70 Days On Market

  Current Estimated Value $301,763

  Last Listing Agent Bente Brown Hudson Premium Realty

  3120 Whispering Hills, Chester, NY 10918
• 

  Est $481,301

  Not Listed For Sale

  30 Trotting Dr, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft
  • Built 1968

  30 Trotting Dr, Chester, NY 10918

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent Christine Koenig Keller Williams Realty
• 

  

  /26

  $379,900

  $45K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,026 Sq Ft

  7 Hambletonian Ave, Chester, NY 10918

  Great new price! Come take a look at this 2 bedroom charmer with additional room offers potential 3+ bedrooms. Larger than it looks - need to see. Discover the timeless charm and surprising spaciousness of this delightful carriage house, set on a property rich with character and possibility. Step inside to a generous living room where a wood burning fireplace, hardwood floors, and a large bay

  William Scolza HomeSmart Homes & Estates

  7 Hambletonian Ave, Chester, NY 10918
• 

  

  /11

  $29,000

  Sold Nov 03, 2025

  L27 Carriage Knolls Rd, Chester, NY 12817

  • Land
  • 1.8 Acres
  • $16,111 per Acre

  Last Sold Summary

  • 71% Below List Price
  • 20 Days On Market

  Last Listing Agent Walter Swartz Gallo Realty ADK Inc

  L27 Carriage Knolls Rd, Chester, NY 12817
• 

  Est $629,206

  Not Listed For Sale

  38 Park Dr, Chester, NY 10918

  • 5 Beds
  • 3.5 Baths
  • 2,770 Sq Ft
  • Built 1968

  38 Park Dr, Chester, NY 10918

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Patricia Hyer Howard Hanna Rand Realty
• 

  

  /19

  $74,900

  $19K PRICE INCREASE

  • Land
  • 4.05 Acres
  • $18,494 per Acre

  85 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

  85 Carriage Knoll Rd, Chester, NY 12817
• 

  $382,000

  Sold Sep 29, 2025

  3915 Whispering Hills, Chester, NY 10918

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

  Last Sold Summary

  • 4% Above List Price
  • $287/SF
  • 13 Days On Market

  Current Estimated Value $382,334

  Last Listing Agent Kristie Jacques Century 21 Full Service Realty

  3915 Whispering Hills, Chester, NY 10918
• 

  Est $577,261

  Not Listed For Sale

  77 Surrey Rd, Chester, NY 10918

  • 5 Beds
  • 2.5 Baths
  • 2,136 Sq Ft
  • Built 1968

  77 Surrey Rd, Chester, NY 10918

  Last Sold Summary

  • 43 Days On Market

  Last Listing Agent Pedro Garcia Curasi Realty, Inc.
• 

  

  /21

  $370,000

  • 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
• 

  $305,000

  Sold Aug 22, 2025

  4501 Whispering Hills Dr, Chester, NY 10918

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft
  • Built 1987

  Last Sold Summary

  • 9% Above List Price
  • $281/SF
  • 27 Days On Market

  Last Listing Agent Bernadette Giordano Howard Hanna Rand Realty

  4501 Whispering Hills Dr, Chester, NY 10918

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