Chester, NY Homes

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  /23

  $400,000

  • 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
• 

  $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 $384,229

  Last Listing Agent Amanda Dnistrian ARC Realty 1 in Sales

  3816 Whispering Hills, Chester, NY 10918
• 

  Est $620,166 Not Listed For Sale

  243 Bull Mill Rd, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 2,021 Sq Ft
  • Built 1985

  243 Bull Mill Rd, Chester, NY 10918

  Last Sold Summary

  • 3% Above List Price
  • $297/SF
  • 11 Days On Market

  • Last Sold Price $600,000
  • Mar 18, 2024

  Last Listing Agent Debra gay Coldwell Banker Realty
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  /21

  $549,000

  • 3 Beds
  • 1.5 Baths
  • 1,644 Sq Ft

  38 Jefferson Dr, Monroe, NY 10950

  Welcome home! This wonderful quiet neighborhood, Lake Hill Farms, off of Lakes Rd. On the outskirts of Monroe, makes this a great commuter and convenient location, from hiking trails, parks, Woodbury Commons, shopping, train station, and dinning. This home has a nice sized backyard. The deck furniture and gazebo are included, underneath your deck is an enclosed screened in patio which will give

  Lance Gibbs Arrowhead Realty

  38 Jefferson Dr, Monroe, NY 10950
• 

  $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 $623,362

  Last Listing Agent Karen Gauvin Our House Real Estate Group

  40 Mountainside Dr, Chester, NY 10918
• 

  Est $536,585 Not Listed For Sale

  119 Booth Rd, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 1,944 Sq Ft
  • Built 1976

  119 Booth Rd, Chester, NY 10918

  Last Sold Summary

  • 2% Above List Price
  • $270/SF
  • 39 Days On Market

  • Last Sold Price $525,000
  • Nov 20, 2024

  Last Listing Agent Donna Gennaro Howard Hanna Rand Realty
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  /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
• 

  $310,000 Sold Apr 29, 2026

  111 Lake Region Blvd, Monroe, NY 10950

  • 2 Beds
  • 1 Bath
  • 792 Sq Ft
  • Built 1950

  Last Sold Summary

  • $391/SF
  • 43 Days On Market

  Current Estimated Value $308,018

  Last Listing Agent Donna Ramundo Keller Williams Valley Realty

  111 Lake Region Blvd, Monroe, NY 10950
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  Est $713,507 Not Listed For Sale

  61 Nancy Ln, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,700 Sq Ft
  • Built 2002

  61 Nancy Ln, Chester, NY 10918

  Last Sold Summary

  • 10% Above List Price
  • $241/SF
  • 35 Days On Market

  • Last Sold Price $650,000
  • Oct 31, 2023

  Last Listing Agent Martha Randazzo Howard Hanna Rand Realty
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  /39

  $319,900

  • 3 Beds
  • 2.5 Baths
  • 1,320 Sq Ft

  607 Mountain Laurel Dr, Monroe, NY 10950

  Monroe-Woodbury Schools Townhouse with Low Taxes — Zoned for highly sought-after Pine Tree & Sapphire Elementary Schools. Step into this inviting 3-bedroom, 2.5-bath townhouse in the desirable Windridge community where space, light, and thoughtful updates come together. The spacious living room showcases younger laminate flooring that looks beautiful and cleans like a dream, while front-facing

  Rosalie Cook Weichert Realtors

  607 Mountain Laurel Dr, Monroe, NY 10950
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  /2

  $87,500 Sold Aug 18, 2025

  L7 Atateka Dr, Chester, NY 12817

  • Land
  • 6.38 Acres
  • $13,715 per Acre

  Last Sold Summary

  • 47% Below List Price
  • 608 Days On Market

  Last Listing Agent Jill Brady Hunt ERA

  L7 Atateka Dr, Chester, NY 12817
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  Est $605,032 Not Listed For Sale

  88 Nancy Ln, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,768 Sq Ft
  • Built 1992

  88 Nancy Ln, Chester, NY 10918

  Last Sold Summary

  • 10% Above List Price
  • $199/SF
  • 44 Days On Market

  • Last Sold Price $549,675
  • May 20, 2024

  Last Listing Agent Christopher Rose REALHome Services & Solutions
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  /48

  $925,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 3,680 Sq Ft

  21 Bull Mine Rd, Chester, NY 10918

  Welcome to this distinguished colonial residence offering five bedrooms and three and a half baths, gracefully positioned on 2.3 acres of private, scenic grounds. Set back from the road, the home is surrounded by expansive green lawns, providing an unparalleled sense of privacy and sophistication. The inviting front porch presents an ideal space to enjoy your morning coffee while taking in the

  Donna Gennaro Howard Hanna Rand Realty

  21 Bull Mine Rd, Chester, NY 10918
• 

  $460,000 Sold Apr 01, 2026

  391 Bull Mill Rd, Chester, NY 10918

  • 2 Beds
  • 2 Baths
  • 1,714 Sq Ft
  • Built 1900

  Last Sold Summary

  • 25% Below List Price
  • $268/SF
  • 217 Days On Market

  Current Estimated Value $488,704

  Last Listing Agent Alexandra Zinko Century 21 Realty Center

  391 Bull Mill Rd, Chester, NY 10918
• 

  Est $572,523 Not Listed For Sale

  38 Rebecca Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 1,910 Sq Ft
  • Built 1990

  38 Rebecca Rd, Chester, NY 10918

  Last Sold Summary

  • 3% Above List Price
  • $291/SF
  • 30 Days On Market

  • Last Sold Price $555,000
  • Dec 12, 2024

  Last Listing Agent Steve Esposito HomeSmart Homes & Estates
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  /31

  $389,000

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

  1221 Whispering Hills, Chester, NY 10918

  Update: Last buyers financing fell through so this wonderful property can be yours!! This is a must see! Will not last! Welcome to this beautifully renovated, spacious 3-bedroom, 2.5-bathroom, end-unit condo offering privacy, comfort, and elevated living in the desirable Whispering Hills community in picturesque Chester, NY! Perfectly positioned at the end of the row for added privacy and natural

  Malia Leonard BUY NY REALTY LLC

  1221 Whispering Hills, Chester, NY 10918
• 

  $334,900 Sold Jun 20, 2025

  1610 Whispering Hills, Chester, NY 10918

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

  Last Sold Summary

  • 6% Below List Price
  • $252/SF
  • 185 Days On Market

  Current Estimated Value $345,572

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  1610 Whispering Hills, Chester, NY 10918
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  Est $591,341 Not Listed For Sale

  32 Rebecca Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,411 Sq Ft
  • Built 2000

  32 Rebecca Rd, Chester, NY 10918

  Last Sold Summary

  • 11% Above List Price
  • $222/SF
  • 38 Days On Market

  • Last Sold Price $535,000
  • Dec 05, 2023

  Last Listing Agent Rosalie Cook Weichert Realtors
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  /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
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  $320,000 Sold Dec 12, 2025

  2317 Whispering Hills, Chester, NY 10918

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft
  • Built 1984

  Last Sold Summary

  • 7% Above List Price
  • $299/SF
  • 20 Days On Market

  Current Estimated Value $317,531

  Last Listing Agent Jeffrey Morrissey Epique Realty

  2317 Whispering Hills, Chester, NY 10918
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  Est $688,388 Not Listed For Sale

  3 Stacey Ln, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 2,904 Sq Ft
  • Built 1988

  3 Stacey Ln, Chester, NY 10918

  Last Sold Summary

  • 14% Above List Price
  • $208/SF
  • 20 Days On Market

  • Last Sold Price $605,000
  • Aug 27, 2023

  Last Listing Agent Abraham Schwartz Priority Management
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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
• 

  $415,000 Sold Jan 23, 2026

  47 Greycourt Ave, Chester, NY 10918

  • 4 Beds
  • 1.5 Baths
  • 1,386 Sq Ft
  • Built 1959

  Last Sold Summary

  • 8% Below List Price
  • $299/SF
  • 81 Days On Market

  Current Estimated Value $417,904

  Last Listing Agent Pedro Garcia Curasi Realty, Inc.

  47 Greycourt Ave, Chester, NY 10918
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  Est $557,213 Not Listed For Sale

  56 Goosepond Mountain Rd, Chester, NY 10918

  • 3 Beds
  • 3 Baths
  • 3,080 Sq Ft
  • Built 1996

  56 Goosepond Mountain Rd, Chester, NY 10918

  Last Sold Summary

  • 4% Above List Price
  • $174/SF
  • 34 Days On Market

  • Last Sold Price $535,000
  • Jul 19, 2024

  Last Listing Agent Linda Ross Linda C Ross Real Estate Inc
• 

  

  /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
• 

  $845,000 Sold Dec 18, 2025

  11 Saddle Hill Rd, Chester, NY 10918

  • 4 Beds
  • 4 Baths
  • 3,489 Sq Ft
  • Built 2006

  Last Sold Summary

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

  Current Estimated Value $860,399

  Last Listing Agent Alissa Taylor-Vetell Keller Williams Realty

  11 Saddle Hill Rd, Chester, NY 10918
• 

  Est $780,654 Not Listed For Sale

  137 Creamery Pond Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,822 Sq Ft
  • Built 2002

  137 Creamery Pond Rd, Chester, NY 10918

  Last Sold Summary

  • 4% Above List Price
  • $266/SF
  • 53 Days On Market

  • Last Sold Price $750,000
  • Apr 25, 2025

  Last Listing Agent John Stika Keller Williams Realty
• 

  

  /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
• 

  $560,000 Sold Aug 19, 2025

  21 Jeffrey Dr, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft
  • Built 1993

  Last Sold Summary

  • 6% Above List Price
  • $250/SF
  • 37 Days On Market

  Current Estimated Value $584,766

  Last Listing Agent Kevin Tuhy Keller Williams Realty

  21 Jeffrey Dr, Chester, NY 10918
• 

  Est $661,299 Not Listed For Sale

  169 Creamery Pond Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,436 Sq Ft
  • Built 2002

  169 Creamery Pond Rd, Chester, NY 10918

  Last Sold Summary

  • 13% Above List Price
  • $240/SF
  • 16 Days On Market

  • Last Sold Price $585,000
  • Dec 13, 2023

  Last Listing Agent Michele Tobin Keller Williams Realty
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  /2

  $500,000 Pending

  • Land
  • 36,098 Sq Ft
  • $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
• 

  $500,000 Sold Oct 20, 2025

  15 Mari Rd, Chester, NY 10918

  • 4 Beds
  • 2 Baths
  • 1,888 Sq Ft
  • Built 1971

  Last Sold Summary

  • $265/SF
  • 56 Days On Market

  Current Estimated Value $510,543

  Last Listing Agent Nicholas Carbone HomeSmart Homes & Estates

  15 Mari Rd, Chester, NY 10918
• 

  Est $606,868 Not Listed For Sale

  19 Mount Ridge Ct, Monroe, NY 10950

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

  19 Mount Ridge Ct, Monroe, NY 10950

  Last Sold Summary

  • 1% Above List Price
  • $223/SF
  • 15 Days On Market

  • Last Sold Price $602,000
  • Feb 13, 2025

  Last Listing Agent Christian Baez Keller Williams Hudson Valley
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  /50

  $849,900

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

  149 Creamery Pond Rd, Chester, NY 10918

  Welcome to the highly sought-after Creamery Estate! This inviting waterfront Colonial-style home offers the perfect blend of comfort, charm, and scenic beauty, set on an acre of beautifully maintained grounds with peaceful views of Creamery Pond. This 3-bedroom, 3 full bath home features hardwood floors throughout and a spacious, easy-flow layout designed for everyday living. The updated kitchen,

  Carla Terranova Keller Williams Realty

  149 Creamery Pond Rd, Chester, NY 10918
• 

  $400,000 Sold Jul 28, 2025

  7 Garden St, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 1,435 Sq Ft
  • Built 1900

  Last Sold Summary

  • $279/SF
  • 25 Days On Market

  Current Estimated Value $407,522

  Last Listing Agent Harmoni VanEtten eXp Realty

  7 Garden St, Chester, NY 10918
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  Est $574,794 Not Listed For Sale

  7 Mount Ridge Ct, Monroe, NY 10950

  • 4 Beds
  • 2.5 Baths
  • 2,136 Sq Ft
  • Built 2002

  7 Mount Ridge Ct, Monroe, NY 10950

  Last Sold Summary

  • 5% Above List Price
  • $257/SF
  • 10 Days On Market

  • Last Sold Price $550,000
  • Aug 06, 2024

  Last Listing Agent Rosalie Cook Weichert Realtors
• 

  

  /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
• 

  $690,000 Sold Jul 09, 2025

  2 Laura Dr, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,592 Sq Ft
  • Built 1986

  Last Sold Summary

  • 6% Above List Price
  • $266/SF
  • 31 Days On Market

  Current Estimated Value $702,931

  Last Listing Agent Virginia Corbett eXp Realty

  2 Laura Dr, Chester, NY 10918
• 

  Est $406,369 Not Listed For Sale

  465 Meri Ln, Monroe, NY 10950

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

  465 Meri Ln, Monroe, NY 10950

  Last Sold Summary

  • 2% Above List Price
  • $236/SF
  • 55 Days On Market

  • Last Sold Price $400,000
  • Sep 08, 2023

  Last Listing Agent Wenpeng Guan Keller Williams Hudson Valley
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  /9

  $149,900

  • Land
  • 8,873 Sq Ft
  • $735,886 per Acre

  2 Imperial Park, Chester, NY 10918

  Large 2 story storage barn approx 80' x 30' with silo for sale in the Town of Chester. 5 garage doors - 4 are 6 feet high, 1 door is 7 foot high with loading dock. Plenty of storage on first and second level. Small office. Has electric, but is turned off. Has well water, but no septic - lot is too small - only .20 acre. Not a buildable lot. Barn was subdivided off from neighboring farm. Has loft

  William Scolza HomeSmart Homes & Estates

  2 Imperial Park, Chester, NY 10918

Showing Results 161 - 200, Page 5 of 18