Chester, NY Homes

• 

  $367,500 Sold Aug 29, 2025

  3911 Whispering Hills, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Above List Price
  • $279/SF
  • 25 Days On Market

  Current Estimated Value $375,571

  Last Listing Agent Hershel Lowy Master Realty Group Inc.

  3911 Whispering Hills, Chester, NY 10918
• 

  Est $382,441 Not Listed For Sale

  463 Meri Ln, Monroe, NY 10950

  • 3 Beds
  • 2.5 Baths
  • 1,694 Sq Ft
  • Built 2001

  463 Meri Ln, Monroe, NY 10950

  Last Sold Summary

  • 20% Above List Price
  • $189/SF
  • 34 Days On Market

  • Last Sold Price $320,000
  • Jan 24, 2024

  Last Listing Agent Beth Palma Keller Williams Realty
• 

  

  

  /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
• 

  $610,000 Sold Sep 19, 2025

  18 Grant Dr, Monroe, NY 10950

  • 4 Beds
  • 2.5 Baths
  • 2,144 Sq Ft
  • Built 1994

  Last Sold Summary

  • 6% Above List Price
  • $285/SF
  • 27 Days On Market

  Current Estimated Value $628,251

  Last Listing Agent Donna Gennaro Howard Hanna Rand Realty

  18 Grant Dr, Monroe, NY 10950
• 

  Est $380,732 Not Listed For Sale

  301 Heritage Ln, Monroe, NY 10950

  • 3 Beds
  • 2.5 Baths
  • 1,698 Sq Ft
  • Built 1998

  301 Heritage Ln, Monroe, NY 10950

  Last Sold Summary

  • $224/SF
  • 111 Days On Market

  • Last Sold Price $380,000
  • Oct 30, 2024

  Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales
• 

  /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
• 

  $536,000 Sold Aug 06, 2025

  16 Ayr Rd, Chester, NY 10918

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

  Last Sold Summary

  • 9% Above List Price
  • $312/SF
  • 62 Days On Market

  Current Estimated Value $551,471

  Last Listing Agent Luanne McGann Century 21 Full Service Realty

  16 Ayr Rd, Chester, NY 10918
• 

  Est $535,229 Not Listed For Sale

  51 Pewter Cir, Chester, NY 10918

  • 3 Beds
  • 3.5 Baths
  • 2,623 Sq Ft
  • Built 2007

  51 Pewter Cir, Chester, NY 10918

  Last Sold Summary

  • 6% Above List Price
  • $193/SF
  • 67 Days On Market

  • Last Sold Price $505,000
  • Sep 19, 2024

  Last Listing Agent Michele Tobin Keller Williams Realty
• 

  

  /45

  $850,000

  • 4 Beds
  • 2.5 Baths
  • 2,722 Sq Ft

  5 Gabriels Dr, Chester, NY 10918

  Welcome to Blooming Grove NY (Chester) Monroe/Woodbury Schools! Wow! This home has a vibe! Custom built 4 bedroom colonial with a front porch, sitting on 3.2 acres fully fenced green property to protect all the flowers, foliage and specimen plantings. This home features spacious rooms throughout, hardwood floors on the main level, Eat in kitchen with open feel to the family room with a warm

  Naomi Streicher Q Home Sales

  5 Gabriels Dr, Chester, NY 10918
• 

  $520,000 Sold Feb 11, 2026

  80 Pewter Cir, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,946 Sq Ft
  • Built 2006

  Last Sold Summary

  • 3% Below List Price
  • $267/SF
  • 25 Days On Market

  Current Estimated Value $519,306

  Last Listing Agent Julie Klein BHG Real Estate Green Team

  80 Pewter Cir, Chester, NY 10918
• 

  Est $538,269 Not Listed For Sale

  53 Pewter Cir, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 2,210 Sq Ft
  • Built 2007

  53 Pewter Cir, Chester, NY 10918

  Last Sold Summary

  • 4% Above List Price
  • $235/SF
  • 33 Days On Market

  • Last Sold Price $520,000
  • May 28, 2024

  Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales
• 

  

  /45

  $899,900

  • 5 Beds
  • 3 Baths
  • 3,846 Sq Ft

  2 Heidi Ln, Chester, NY 10918

  Set at the end of a quiet executive cul-de-sac, this refined modern colonial offers a rare blend of quality, scale, and effortless livability on over two acres of level, park-like grounds framed by mature trees. Designed for both everyday comfort and elevated entertaining, the home unfolds with a sense of openness and intention, where natural light and thoughtful craftsmanship define every

  Frank Muccari Cronin & Company Real Estate

  2 Heidi Ln, Chester, NY 10918
• 

  /2

  $75,000 Sold Nov 10, 2025

  6 E Shore Dr, Chester, NY 12817

  • Land
  • 29,185 Sq Ft
  • $111,940 per Acre

  Last Sold Summary

  • 36% Above List Price
  • 5 Days On Market

  Current Estimated Value $118,500

  Last Listing Agent Michelle Decoteau KW Platform

  6 E Shore Dr, Chester, NY 12817
• 

  Est $693,702 Not Listed For Sale

  15 Pewter Cir, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 3,223 Sq Ft
  • Built 1999

  15 Pewter Cir, Chester, NY 10918

  Last Sold Summary

  • 8% Above List Price
  • $200/SF
  • 218 Days On Market

  • Last Sold Price $645,000
  • Jun 13, 2024

  Last Listing Agent Jennifer Connolly BHHS Gross & Jansen
• 

  

  /50

  $3,400,000

  • 4 Beds
  • 4 Baths
  • 7,750 Sq Ft

  19 Greentree Ln, Chester, NY 10918

  Set behind a gated entrance with a private guard house and unfolding across 8.4 private acres, The Retreat at Greentree is a true estate in every sense, engineered for privacy, designed for lifestyle, and positioned as one of the most unique offerings in the Hudson Valley. A cascading waterfall greets you on arrival, establishing a sense of calm and separation from the outside world. From that

  Jake Garay Serhant LLC

  19 Greentree Ln, Chester, NY 10918
• 

  

  /3

  $710,000 Sold Feb 24, 2026

  1 Hillview Terrace, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • Built 1997

  Last Sold Summary

  • $355/SF
  • 21 Days On Market

  Current Estimated Value $711,144

  Last Listing Agent Sandra Cassio Robert DeFalco Realty, Inc.

  1 Hillview Terrace, Chester, NY 10918
• 

  Est $595,065 Not Listed For Sale

  11 Pewter Cir, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,156 Sq Ft
  • Built 1999

  11 Pewter Cir, Chester, NY 10918

  Last Sold Summary

  • 24% Above List Price
  • $223/SF
  • 102 Days On Market

  • Last Sold Price $480,000
  • Oct 12, 2023

  Last Listing Agent Jorge Vasquez Vasquez Realty
• 

  /2

  $37,900

  • Land
  • 2.7 Acres
  • $14,037 per Acre

  0 Joan's Ct, Chester, NY 12817

  Own 2.70 wooded acres (Lot 10) in Chestertown, NY, offering a peaceful setting surrounded by the natural beauty of the Adirondacks. Enjoy easy access to Loon Lake, Gore Mountain for skiing, and endless opportunities for hiking, boating, and year-round outdoor adventure. The area is known for its quiet charm and fresh mountain air, while still being about an hour from Albany for shopping, dining,

  Derek Greene The Greene Realty Group

  0 Joan's Ct, Chester, NY 12817
• 

  $310,000 Sold Dec 10, 2025

  3107 Whispering Hills, Chester, NY 10918

  • 2 Beds
  • 1.5 Baths
  • 1,086 Sq Ft
  • Built 1987

  Last Sold Summary

  • 5% Below List Price
  • $285/SF
  • 143 Days On Market

  Current Estimated Value $315,863

  Last Listing Agent Hershel Lowy Master Realty Group Inc.

  3107 Whispering Hills, Chester, NY 10918
• 

  Est $675,540 Not Listed For Sale

  16 Pewter Cir, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,849 Sq Ft
  • Built 1998

  16 Pewter Cir, Chester, NY 10918

  Last Sold Summary

  • 1% Below List Price
  • $240/SF
  • 60 Days On Market

  • Last Sold Price $685,000
  • Oct 15, 2024

  Last Listing Agent Lisa McAteer Scranton Wilkes Barre Regional
• 

  

  /13

  $640,000

  • 3 Beds
  • 1.5 Baths
  • 2,136 Sq Ft

  4 Greycourt Rd, Chester, NY 10918

  Welcome to 4 Greycourt Road, your dream home awaits! This delightful residence boasts a spacious 6-room layout, featuring 3 generous bedrooms and 1.5 baths, all nestled on over 2.5 acres of stunning greenery. Imagine whipping up culinary masterpieces in the well-appointed kitchen, complete with ample cabinetry and modern appliances—perfect for any cooking enthusiast! Each bedroom is a serene

  Nathen Singer MK Realty Inc

  4 Greycourt Rd, Chester, NY 10918
• 

  $700,000 Sold Jul 08, 2025

  138 Dug Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,452 Sq Ft
  • Built 1974

  Last Sold Summary

  • $285/SF
  • 49 Days On Market

  Current Estimated Value $706,723

  Last Listing Agent Jake Garay Serhant LLC

  138 Dug Rd, Chester, NY 10918
• 

  Est $341,395 Not Listed For Sale

  274 Heritage Ln, Monroe, NY 10950

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

  274 Heritage Ln, Monroe, NY 10950

  Last Sold Summary

  • 2% Above List Price
  • $243/SF
  • 39 Days On Market

  • Last Sold Price $335,000
  • Dec 27, 2024

  Last Listing Agent Jeffrey Freundlich Howard Hanna Rand Realty
• 

  

  /7

  $500,000

  • Land
  • 9.78 Acres
  • $51,125 per Acre

  30 Harding Way, Chester, NY 10950

  An exceptional opportunity for builders and investors in the highly desirable Town of Chester and Town of Monroe, within the Monroe–Woodbury School District. This offering includes four contiguous lots for the price of one, providing significant development potential. The assemblage consists of 30 Harding Way (0.18 acres; Section 27, Block 3, Lot 11), sold together with the adjoining parcels: Lot

  Ida Payne Keller Williams Realty

  30 Harding Way, Chester, NY 10950
• 

  $290,000 Sold Jun 05, 2025

  4401 Whispering Hills Dr, Chester, NY 10918

  • 2 Beds
  • 1 Bath
  • 1,118 Sq Ft
  • Built 1989

  Last Sold Summary

  • 5% Above List Price
  • $259/SF
  • 30 Days On Market

  Current Estimated Value $307,139

  Last Listing Agent Annmarie Kovacs Howard Hanna Rand Realty

  4401 Whispering Hills Dr, Chester, NY 10918
• 

  Est $361,925 Not Listed For Sale

  245 Heritage Ln, Monroe, NY 10950

  • 3 Beds
  • 2.5 Baths
  • 1,585 Sq Ft
  • Built 1989

  245 Heritage Ln, Monroe, NY 10950

  Last Sold Summary

  • 19% Above List Price
  • $192/SF
  • 17 Days On Market

  • Last Sold Price $305,000
  • Aug 18, 2023

  Last Listing Agent Anita S. Cristiano Five Star Realty Group Intl
• 

  

  /3

  $75,000 Pending

  • 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
• 

  $675,000 Sold Nov 18, 2025

  165 Creamery Pond Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,548 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $265/SF
  • 55 Days On Market

  Current Estimated Value $676,672

  Last Listing Agent Kichka Pascaru Christie's Int. Real Estate

  165 Creamery Pond Rd, Chester, NY 10918
• 

  Est $369,797 Not Listed For Sale

  225 Eagleton Dr, Monroe, NY 10950

  • 3 Beds
  • 2.5 Baths
  • 1,694 Sq Ft
  • Built 1997

  225 Eagleton Dr, Monroe, NY 10950

  Last Sold Summary

  • 9% Above List Price
  • $201/SF
  • 30 Days On Market

  • Last Sold Price $340,000
  • Aug 04, 2023

  Last Listing Agent Theresa Budich Howard Hanna Rand Realty
• 

  

  /8

  $39,500

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

  34 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

  34 Carriage Knolls Rd, Chester, NY 12817
• 

  $350,000 Sold Jul 28, 2025

  2816 Whispering Hills, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Built 1984

  Last Sold Summary

  • $263/SF
  • 23 Days On Market

  Current Estimated Value $361,818

  Last Listing Agent Bernadette Giordano Howard Hanna Rand Realty

  2816 Whispering Hills, Chester, NY 10918
• 

  Est $363,995 Not Listed For Sale

  152 Eagleton Dr, Monroe, NY 10950

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

  152 Eagleton Dr, Monroe, NY 10950

  Last Sold Summary

  • 4% Below List Price
  • $254/SF
  • 20 Days On Market

  • Last Sold Price $379,000
  • Oct 22, 2024

  Last Listing Agent Alissa Taylor-Vetell Keller Williams Realty
• 

  

  /45

  $1,300,000

  • 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
• 

  $310,000 Sold Jul 21, 2025

  4706 Whispering Hills, Chester, NY 10918

  • 2 Beds
  • 1.5 Baths
  • 1,086 Sq Ft
  • Built 1987

  Last Sold Summary

  • 2% Above List Price
  • $285/SF
  • 18 Days On Market

  Current Estimated Value $316,753

  Last Listing Agent Jessica Evans Keller Williams Hudson Valley

  4706 Whispering Hills, Chester, NY 10918
• 

  Est $586,865 Not Listed For Sale

  14 Jeffrey Dr, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 2,117 Sq Ft
  • Built 1987

  14 Jeffrey Dr, Chester, NY 10918

  Last Sold Summary

  • 6% Above List Price
  • $261/SF
  • 37 Days On Market

  • Last Sold Price $552,000
  • Jun 08, 2024

  Last Listing Agent Savannah Miceli Century 21 Alliance Rlty Group
• 

  

  /33

  $260,000

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  1401 Whispering Hills, Chester, NY 10918

  Discover the perfect blend of comfort, convenience, and community in this 2-bedroom, 1-bath end-unit townhouse. Situated in a quiet corner of the neighborhood, this home offers extra privacy and natural light, along with the added benefit of an attached 1-car garage for secure parking and storage. Inside, you'll find a thoughtfully designed layout that maximizes space and livability - ideal for

  Debbie Goldstein Howard Hanna Rand Realty

  1401 Whispering Hills, Chester, NY 10918
• 

  $265,000 Sold Jul 11, 2025

  10 El Dorado Trail, Chester, NY 10918

  • Land
  • 6.3 Acres
  • $42,063 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 152 Days On Market

  Current Estimated Value $254,092

  Last Listing Agent Lisandra Rivera Keller Williams Realty

  10 El Dorado Trail, Chester, NY 10918
• 

  Est $484,454 Not Listed For Sale

  19 Well Sweep Ln, Chester, NY 10918

  • 2 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1987

  19 Well Sweep Ln, Chester, NY 10918

  Last Sold Summary

  • 31% Above List Price
  • $224/SF
  • 52 Days On Market

  • Last Sold Price $369,000
  • Feb 23, 2024

  Last Listing Agent Donna Brunell RE/MAX Benchmark Realty Group
• 

  

  /3

  $650,000

  • Land
  • 2 Acres
  • $325,000 per Acre

  50 Elkay Dr, Chester, NY 10918

  Last remaining parcel available on Elkay Drive in the Chester Industrial Park.This 2-acre industrial lot was previously fully approved for a two-story building with loading docks. While approvals expired approximately 10 years ago, the site’s industrial potential remains strong. Both adjacent parcels are currently under development, with 30,000+ SF warehouse facilities being constructed,

  Leib Glanz Point Realty USA

  50 Elkay Dr, Chester, NY 10918
• 

  $750,000 Sold May 15, 2025

  16 Spectrum Dr, Chester, NY 10918

  • 3 Beds
  • 4 Baths
  • 2,276 Sq Ft
  • Built 1999

  Last Sold Summary

  • 5% Above List Price
  • $330/SF
  • 16 Days On Market

  Current Estimated Value $764,723

  Last Listing Agent John Olivero Keller Williams Realty

  16 Spectrum Dr, Chester, NY 10918

Showing Results 201 - 240, Page 6 of 18