Chester, NY Homes

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  $879,900

  • 4 Beds
  • 2.5 Baths
  • 3,200 Sq Ft

  1414 Kings Hwy, Chester, NY 10918

  Beautiful custom new homes to be built in Golden Meadows Estates, offering the rare combination of municipal water and sewer, thoughtfully designed floor plans, and stunning lots in a highly desirable location in the Warwick school district. Homes will start at $780,000, with multiple design options available to suit a variety of lifestyles. Lots 1 and 2 will feature custom Bilonial designs with

  Carla Terranova Keller Williams Realty

  1414 Kings Hwy, Chester, NY 10918
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  /10

  $2,200 per month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Townhouse for Rent

  82 High St Unit 5, Chester, NY 10918

  Very bright and spacious top-floor Penthouse apartment! Come see this open layout floorplan. The updated kitchen has a new stainless steel refrigerator and dishwasher. The Primary bedroom has large double closets and can accommodate a king-size bed. The living room/dining room combination is bright and sun-filled, with plenty of windows and an outside deck. You’ll appreciate the convenience of

  Lynda Hoss Weichert Realtors

  82 High St Unit 5, Chester, NY 10918
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  $899,999 Sold Jun 18, 2025

  29 Meadow Ave, Chester, NY 10918

  • 4 Beds
  • 3 Baths
  • 3,167 Sq Ft
  • Built 2023

  Last Sold Summary

  • 8% Below List Price
  • $284/SF
  • 163 Days On Market

  Current Estimated Value $347,337

  Last Listing Agent Nancy Sardo BHG Real Estate Green Team

  29 Meadow Ave, Chester, NY 10918
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  Est $959,167 Not Listed For Sale

  221 Oxford Rd, Chester, NY 10918

  • 4 Beds
  • 3.5 Baths
  • 4,644 Sq Ft
  • Built 2000

  221 Oxford Rd, Chester, NY 10918

  Last Sold Summary

  • 7% Above List Price
  • $194/SF
  • 132 Days On Market

  Last Sold Price $900,000

  Last Listing Agent Donna Brunell RE/MAX Benchmark Realty Group
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  $925,000

  • 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
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  $2,000 per month

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • House for Rent

  1396 Kings Hwy, Chester, NY 10918

  Newly renovated 3 bedroom unit located in the heart of Sugar Loaf and within the Warwick School District. This second-floor walkup features a bright white kitchen with stainless steel appliances, including an in-unit washer/drier, and offers a large private balcony with scenic views of Sugar Loaf Mountain. The unit is situated above a restaurant; music may be audible as late as 11 PM on Friday

  Roxanne Hartman Timothy W. Kramer

  1396 Kings Hwy, Chester, NY 10918
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  $453,000 Sold May 08, 2025

  16 Academy Ave, Chester, NY 10918

  • 3 Beds
  • 2 Baths
  • 2,358 Sq Ft
  • Built 1850

  Last Sold Summary

  • 1% Above List Price
  • $192/SF
  • 21 Days On Market

  Current Estimated Value $489,681

  Last Listing Agent Celina Rofer Howard Hanna Rand Realty

  16 Academy Ave, Chester, NY 10918
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  Est $485,573 Not Listed For Sale

  26 Maple Ln, Monroe, NY 10950

  • 4 Beds
  • 2 Baths
  • 1,956 Sq Ft
  • Built 1964

  26 Maple Ln, Monroe, NY 10950

  Last Sold Summary

  • 11% Above List Price
  • $224/SF
  • 22 Days On Market

  Last Sold Price $439,000

  Last Listing Agent Steven Brown Hudson Valley Realty & Busines
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  $874,400

  • 4 Beds
  • 2 Baths
  • 2,466 Sq Ft

  651 Lakes Rd, Monroe, NY 10950

  Rare opportunity to purchase this gorgeous property that consists of 3 homes nestled on 3.5 beautiful acres. The main Colonial residence has been gutted and will need to be renovated/rebuilt, however, you can live in one of the additional two residences while you renovate! The 2nd residence called the “stone cottage” has 2 fieldstone fireplaces, a full kitchen, a vaulted ceiling in the bedroom, a

  Frank Golio Howard Hanna Rand Realty

  651 Lakes Rd, Monroe, NY 10950
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  /29

  $3,050 per month

  • 4 Beds
  • 1.5 Baths
  • 1,605 Sq Ft
  • House for Rent

  98 Main St, Chester, NY 10918

  Welcome to 98 Main St: a gracious Colonial in the center of the village of Chester!A huge "wrap-around" front porch greets you when you arrive. Once inside, you will be impressed with the "old world" charm of the stained-glass windows, dark wood trim, Hardwood floors and the pocket doors in the Living Room. Many large windows downstairs let in plenty of sunlight! Upstairs there are 4 nice

  Eveline White Hudson Valley Griffith

  98 Main St, Chester, NY 10918
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  $575,000 Sold Sep 23, 2025

  12 Bianca Blvd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 3,200 Sq Ft
  • Built 1987

  Last Sold Summary

  • 2% Below List Price
  • $180/SF
  • 126 Days On Market

  Current Estimated Value $610,674

  Last Listing Agent Aoife Freeman Howard Hanna Rand Realty

  12 Bianca Blvd, Chester, NY 10918
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  Est $445,926 Not Listed For Sale

  13 Maple Ln, Monroe, NY 10950

  • 4 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Built 1962

  13 Maple Ln, Monroe, NY 10950

  Last Sold Summary

  • 1% Below List Price
  • $290/SF
  • 36 Days On Market

  Last Sold Price $452,000

  Last Listing Agent Nicole Isaacs Century 21 Full Service Realty
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  $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
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  $2,850 per month

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Townhouse for Rent

  4321 Whispering Hills, Chester, NY 10918

  This is a beautiful rental, If you are looking to rent, here it is!! plenty of room,3 bedrooms 2.5 baths, 2 car garage, close to amenities, new bathrooms, close to shopping, close to major highways and rail for commuters. Freshly painted, new carpets, hardwood floors redone. Must see if you are looking to rent!!! Additional Information: ParkingFeatures:1 Car Attached.

  Dan Neil Field Pointe Realty LLC

  4321 Whispering Hills, Chester, NY 10918
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  $411,000 Sold Jul 08, 2025

  100 Marian Ct, Warwick, NY 10990

  • 3 Beds
  • 2.5 Baths
  • 1,528 Sq Ft
  • Built 1986

  Last Sold Summary

  • 4% Above List Price
  • $269/SF
  • 26 Days On Market

  Current Estimated Value $422,936

  Last Listing Agent Jennifer DiCostanzo RE/MAX Town & Country

  100 Marian Ct, Warwick, NY 10990
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  Est $506,788 Not Listed For Sale

  7 Maple Ln, Monroe, NY 10950

  • 3 Beds
  • 2 Baths
  • 2,104 Sq Ft
  • Built 1961

  7 Maple Ln, Monroe, NY 10950

  Last Sold Summary

  • 6% Above List Price
  • $228/SF
  • 30 Days On Market

  Last Sold Price $479,000

  Last Listing Agent Jason Madison eXp Realty
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  $639,000

  • 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
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  $2,850 per month

  • 3 Beds
  • 2.5 Baths
  • 1,331 Sq Ft
  • Townhouse for Rent

  2104 Whispering Hills, Chester, NY 10918

  Experience the best of Whispering Hills in this expansive 3-bedroom, 2.5-bathroom townhouse—the largest model available in the community! Currently undergoing a fresh renovation, this home will be move-in ready by April 15, 2026. The layout features a spacious master suite complete with a private walk-in closet, perfect for your wardrobe needs. Located just minutes from premier shopping, dining,

  Jayne M. Prechtel Keller Williams Valley Realty

  2104 Whispering Hills, Chester, NY 10918
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  $620,000 Sold Oct 29, 2025

  9 June Rd, Chester, NY 10918

  • 4 Beds
  • 2.5 Baths
  • 2,402 Sq Ft
  • Built 1999

  Last Sold Summary

  • 4% Below List Price
  • $258/SF
  • 52 Days On Market

  Current Estimated Value $629,360

  Last Listing Agent Jason Madison eXp Realty

  9 June Rd, Chester, NY 10918
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  Est $442,226 Not Listed For Sale

  31 Maple Ln, Monroe, NY 10950

  • 3 Beds
  • 1 Bath
  • 1,686 Sq Ft
  • Built 1969

  31 Maple Ln, Monroe, NY 10950

  Last Sold Summary

  • 4% Above List Price
  • $253/SF
  • 18 Days On Market

  Last Sold Price $426,000

  Last Listing Agent Donna Gennaro Howard Hanna Rand Realty
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  $725,000 Pending

  • 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
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  $310,000 Sold Nov 10, 2025

  3708 Whispering Hills, Chester, NY 10918

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft
  • Built 1990

  Last Sold Summary

  • 5% Above List Price
  • $289/SF
  • 26 Days On Market

  Current Estimated Value $315,549

  Last Listing Agent Nikki Grzegorzewski Keller Williams Realty

  3708 Whispering Hills, Chester, NY 10918
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  Est $420,846 Not Listed For Sale

  48 Maple Ln, Monroe, NY 10950

  • 3 Beds
  • 2 Baths
  • 1,003 Sq Ft
  • Built 1963

  48 Maple Ln, Monroe, NY 10950

  Last Sold Summary

  • 1% Below List Price
  • $426/SF
  • 99 Days On Market

  Last Sold Price $427,000

  Last Listing Agent Franky Garcia Howard Hanna Rand Realty
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  /28

  $305,000

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

  3917 Whispering Hills, Chester, NY 10918

  Welcome to Whispering Hills! This beautifully maintained home features a galley kitchen with stainless steel appliances and a convenient in-unit washer and dryer. The first level offers a stylish half bath and well-kept flooring throughout the kitchen, dining room, and living room. Enjoy cozy evenings by the fireplace, and extend your living space outdoors on the private patio. Upstairs, you’ll

  Jie Liu Keller Williams Hudson Valley

  3917 Whispering Hills, Chester, NY 10918
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  $644,000 Sold Feb 12, 2026

  23 Renies Rd, Chester, NY 10918

  • 3 Beds
  • 3 Baths
  • 3,200 Sq Ft
  • Built 1990

  Last Sold Summary

  • 7% Below List Price
  • $201/SF
  • 100 Days On Market

  Current Estimated Value $683,906

  Last Listing Agent Kristie Jacques Century 21 Full Service Realty

  23 Renies Rd, Chester, NY 10918
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  Est $392,862 Not Listed For Sale

  68 Evan Rd, Warwick, NY 10990

  • 3 Beds
  • 2.5 Baths
  • 1,452 Sq Ft
  • Built 1995

  68 Evan Rd, Warwick, NY 10990

  Last Sold Summary

  • 1% Above List Price
  • $269/SF
  • 39 Days On Market

  Last Sold Price $390,000

  Last Listing Agent Antonette Vogel BHG Real Estate Green Team
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  $699,000

  • 3 Beds
  • 3 Baths
  • 3,000 Sq Ft

  360 Prospect Rd, Chester, NY 10918

  B"H Grab this opportunity!!! Cozy Home in great condition sitting on a 3.2 ACER Property!!! Enjoy the above ground pool !!!Wonderful neighborhood and calm area. Open living room with wood burning fireplace, The kitchen offers a breakfast bar, Center island, Stainless steel appliances, Multiple counter space and cabinets. Finished lower level with a Den/office, Family room and full bathroom.

  Joseph Mendlowitz eRealty Advisors, Inc

  360 Prospect Rd, Chester, NY 10918
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  $780,000 Sold Aug 15, 2025

  27 Grand View Terrace, Chester, NY 10918

  • 5 Beds
  • 3.5 Baths
  • 4,490 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Above List Price
  • $174/SF
  • 43 Days On Market

  Current Estimated Value $802,068

  Last Listing Agent Randolph Rogers eXp Realty

  27 Grand View Terrace, Chester, NY 10918
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  Est $346,954 Not Listed For Sale

  27 Darin Rd, Warwick, NY 10990

  • 2 Beds
  • 2.5 Baths
  • 1,276 Sq Ft
  • Built 1987

  27 Darin Rd, Warwick, NY 10990

  Last Sold Summary

  • 14% Above List Price
  • $239/SF
  • 28 Days On Market

  Last Sold Price $305,000

  Last Listing Agent Lauren Donati Homes By Yara Realty Group LLC
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  /17

  $309,900 Pending

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

  1503 Whispering Hills, Chester, NY 10918

  Lowest priced 3 Bedroom in the complex! This 3 bedroom 2.1 bath end unit is move in with some tlc needed to make it shine! Put your DIY skills to good use! 2 car garage, private patio, central air. Community pool, tennis, playground. close to bus stop, pool and amenities. Easy access to highways Route 17 and the NYS Thruway.

  Darlene Provino Century 21 E & M Williams Rlty

  1503 Whispering Hills, Chester, NY 10918
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  $380,000 Sold Sep 15, 2025

  68 Southside Dr, Monroe, NY 10950

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft
  • Built 1940

  Last Sold Summary

  • 15% Below List Price
  • $233/SF
  • 49 Days On Market

  Current Estimated Value $403,532

  Last Listing Agent Carol Buchanan BHG Real Estate Green Team

  68 Southside Dr, Monroe, NY 10950
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  Est $345,830 Not Listed For Sale

  25 Darin Rd, Warwick, NY 10990

  • 2 Beds
  • 2.5 Baths
  • 1,276 Sq Ft
  • Built 1987

  25 Darin Rd, Warwick, NY 10990

  Last Sold Summary

  • 3% Above List Price
  • $263/SF
  • 96 Days On Market

  Last Sold Price $336,000

  Last Listing Agent Michelle Cameron-Isaacs Keller Williams Realty
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  $1,375,000 Pending

  • 11 Beds
  • 6.5 Baths
  • 4,327 Sq Ft

  10 Damian Ct, Chester, NY 10918

  Welcome to 10 Damian Court — a stunning custom Colonial set on 2.6 acres of beautifully landscaped grounds in a peaceful Chester cul-de-sac. Built in 2004, this impressive home offers over 4,300 sq ft of elegant living space, featuring 11 bedrooms and 6.5 baths designed for comfort and flexibility. Enjoy a spacious eat-in kitchen with granite counters and pantry, a formal dining area, and a

  Elimelech Kremer MS Realty Group USA, Inc

  10 Damian Ct, Chester, NY 10918
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  $850,000 Sold Oct 22, 2025

  284 Bull Mill Rd, Chester, NY 10918

  • 5 Beds
  • 3 Baths
  • 3,485 Sq Ft
  • Built 1997

  Last Sold Summary

  • $244/SF
  • 20 Days On Market

  Current Estimated Value $854,739

  Last Listing Agent Jayne M. Prechtel Keller Williams Valley Realty

  284 Bull Mill Rd, Chester, NY 10918
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  Est $784,515 Not Listed For Sale

  215 Ridge Rd, Chester, NY 10918

  • 3 Beds
  • 3 Baths
  • 3,005 Sq Ft
  • Built 1848

  215 Ridge Rd, Chester, NY 10918

  Last Sold Summary

  • 1% Below List Price
  • $262/SF
  • 119 Days On Market

  Last Sold Price $788,500

  Last Listing Agent Deborah Marks Keller Williams Realty
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  $360,000

  • 3 Beds
  • 1.5 Baths
  • 1,460 Sq Ft

  4 Maple Ln, Monroe, NY 10950

  If you possess talent and intelligence, this is your moment! Attention First time homebuyers and astute investors! Seize this opportunity to improve this charming Fixer upper home. With a little tender loving care, it can be wonderful once more. Situated in a fantastic area, with all amenities nearby. With some effort you can enjoy the benefits forever!

  Joseph Rosenfeld Flag Realty Group

  4 Maple Ln, Monroe, NY 10950
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  $540,000 Sold Aug 28, 2025

  1 Winding Trail, Chester, NY 10918

  • 3 Beds
  • 2.5 Baths
  • 2,040 Sq Ft
  • Built 1991

  Last Sold Summary

  • 10% Below List Price
  • $265/SF
  • 35 Days On Market

  Current Estimated Value $555,905

  Last Listing Agent Donald Serotta Howard Hanna Rand Realty

  1 Winding Trail, Chester, NY 10918
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  Est $507,923 Not Listed For Sale

  201 Hambletonian Rd, Chester, NY 10918

  • 3 Beds
  • 1.5 Baths
  • 1,342 Sq Ft
  • Built 1966

  201 Hambletonian Rd, Chester, NY 10918

  Last Sold Summary

  • 11% Above List Price
  • $340/SF
  • 19 Days On Market

  Last Sold Price $456,000

  Last Listing Agent Kimberly Corkum Keller Williams Realty
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  /5

  $54,900

  • Land
  • 10.14 Acres
  • $5,414 per Acre

  15 Deer Run, Chester, NY 12817

  10+ Acre recreational vacation location in the Town of Chester. Private maintained road with nice camps and homes. The lot feels as if its set in the heart of a wildlife preserve. Small non salvageable cabin on the property that had electric to the site. 6 miles to North Creek the home of Gore Mountain Ski Center. Build your vacation home here in the Adirondacks.

  Patricia Seitz McAlonen Pearsall Realty

  15 Deer Run, Chester, NY 12817
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  $610,000 Sold Aug 25, 2025

  411 Prospect Rd, Chester, NY 10918

  • 4 Beds
  • 2 Baths
  • 1,987 Sq Ft
  • Built 1973

  Last Sold Summary

  • 2% Above List Price
  • $307/SF
  • 39 Days On Market

  Current Estimated Value $616,497

  Last Listing Agent Dana Posner Howard Hanna Rand Realty

  411 Prospect Rd, Chester, NY 10918

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