Chester, NY Homes

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  $635,000

  • 3 Beds
  • 2.5 Baths
  • 1,954 Sq Ft

  25 Sugarloaf Mountain Rd, Chester, NY 10918

  MONROE WOODBURY SCHOOLS! BRAND NEW KITCHEN! ABSOLUTE MUST SEE!Welcome to your dream home in the highly sought-after Monroe Woodbury School District. Privately set at the end of a long driveway on just under one acre, this beautifully renovated Colonial offers an incredible balance of peace, privacy, and recent upgrades.From the moment you step inside, you are greeted by a stunning foyer that

  Frank Muccari Cronin & Company Real Estate

  25 Sugarloaf Mountain Rd, Chester, NY 10918
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  $1,950 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Apartment for Rent

  12 Railroad Ave Unit Floor 2, Chester, NY 10918

  Is there a 2-bed apartment in Chester Village with parking, outdoor space, and walkable access to downtown? This newly refreshed second floor rental offers approximately 1,000 square feet, a private covered deck, garage parking, and an updated kitchen, all set in Historic Downtown Chester near dining, shops, and the Heritage Trail. This spacious apartment at 12 Railroad Avenue, Unit Floor 2

  Geoffrey Green BHG Real Estate Green Team

  12 Railroad Ave Unit Floor 2, Chester, NY 10918
• 

  $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 $478,730

  Last Listing Agent Celina Rofer Howard Hanna Rand Realty

  16 Academy Ave, Chester, NY 10918
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  Est $504,337 Not Listed For Sale

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

  26 Maple Ln, Monroe, NY 10950

  26 Maple Ln, Monroe, NY 10950
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  $304,900 Pending

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  2912 Whispering Hills, Chester, NY 10918

  Welcome home to this beautifully renovated 2 bedroom, 1 bathroom condo located in the desirable Whispering Hills community. Every detail has been thoughtfully updated to combine modern comfort with timeless style. Step inside to discover a new kitchen featuring gorgeous countertops, contemporary cabinetry, and beautiful stainless steel appliances - perfect for cooking, entertaining, or enjoying

  Rebecca Matta-Candela Keller Williams Realty

  2912 Whispering Hills, Chester, NY 10918
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  $3,200 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 $611,838

  Last Listing Agent Aoife Freeman Howard Hanna Rand Realty

  12 Bianca Blvd, Chester, NY 10918
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  Est $438,516 Not Listed For Sale

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

  13 Maple Ln, Monroe, NY 10950

  13 Maple Ln, Monroe, NY 10950
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  $699,990

  • 4 Beds
  • 3 Baths
  • 1,867 Sq Ft

  34 Mountainside Dr, Chester, NY 10918

  ONE LEVEL LIVING/ EASY COMMUTE- with additional space upstairs and down! ... Don't miss this beautiful TURN-KEY Arts & Crafts-style FARMHOUSE TO BE BUILT! ..... COME AND FULLY CUSTOMIZE this 4-bdrm, 3 bath, 2,106+/- sq. ft home (including bonus room)! LARGE MAIN FLOOR PRIMARY BEDROOM with ENSUITE BATH & WALK-IN CLOSET plus A SECOND MAIN FLOOR BEDROOM (NURSERY, OFFICE, CRAFT ROOM ETC.). FANTASTIC

  Karen Gauvin Our House Real Estate Group

  34 Mountainside Dr, 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 $424,267

  Last Listing Agent Jennifer DiCostanzo RE/MAX Town & Country

  100 Marian Ct, Warwick, NY 10990
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  Est $505,558 Not Listed For Sale

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

  7 Maple Ln, Monroe, NY 10950

  7 Maple Ln, Monroe, NY 10950
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  $690,000 Pending

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

  23 Renies Rd, Chester, NY 10918

  Escape to your own sanctuary in this stunning 3 bedroom 3 full bath contemporary cedar home, perfectly blending modern comfort with natural charm. Inside you'll find an open-concept layout with soaring ceilings, large windows, and natural wood finishes that create a warm, modern vibe. The spacious kitchen features stainless appliances, hickory cabinets and an island ideal for entertaining. Two

  Kristie Jacques Century 21 Full Service Realty

  23 Renies Rd, 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 $634,592

  Last Listing Agent Jason Madison eXp Realty

  9 June Rd, Chester, NY 10918
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  Est $406,917 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,686 Sq Ft

  31 Maple Ln, Monroe, NY 10950

  31 Maple Ln, Monroe, NY 10950
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  $650,000 Pending

  • 5 Beds
  • 3.5 Baths
  • 2,550 Sq Ft

  3 Derose Ln, Chester, NY 10918

  This colonial home is truly designed for both family living and entertaining. Upon entering, a two-story entry provides easy access to all areas without needing to pass through other rooms unnecessarily. The spacious kitchen is a highlight, featuring oak cabinets, a pantry, updated appliances and a tiled backsplash and floor. For more casual gatherings, the family room offers hardwood floors. For

  Donna Gennaro Howard Hanna Rand Realty

  3 Derose Ln, 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

  Last Listing Agent Nikki Grzegorzewski Keller Williams Realty

  3708 Whispering Hills, Chester, NY 10918
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  Est $415,735 Not Listed For Sale

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

  48 Maple Ln, Monroe, NY 10950

  48 Maple Ln, Monroe, NY 10950
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  $875,000

  • 3 Beds
  • 2.5 Baths
  • 2,302 Sq Ft

  2 Pine Hill Rd, Chester, NY 10918

  Listed on the National Register of Historic Places in the Sugar Loaf Historic District, this stunning Victorian is a Circa 1910 Sears Roebuck Kit Home (#118 The Clyde). Not only is this your dream home located in beautiful Sugar Loaf, NY, it is also zoned for extensive commercial use. Just a 1-minute walk to the quaint Sugar Loaf Arts & Crafts Village, cafes and Sugar Loaf Performing Arts Center.

  Debbie Walsh SHAHAR Management LLC

  2 Pine Hill 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 $792,282

  Last Listing Agent Randolph Rogers eXp Realty

  27 Grand View Terrace, Chester, NY 10918
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  Est $398,458 Not Listed For Sale

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

  68 Evan Rd, Warwick, NY 10990

  68 Evan Rd, Warwick, NY 10990
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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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  $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 $404,102

  Last Listing Agent Carol Buchanan BHG Real Estate Green Team

  68 Southside Dr, Monroe, NY 10950
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  Est $352,942 Not Listed For Sale

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

  25 Darin Rd, Warwick, NY 10990

  25 Darin Rd, Warwick, NY 10990
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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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  $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 $833,275

  Last Listing Agent Jayne Mangieri Keller Williams Valley Realty

  284 Bull Mill Rd, Chester, NY 10918
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  Est $832,919 Not Listed For Sale

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

  215 Ridge Rd, Chester, NY 10918

  215 Ridge Rd, Chester, NY 10918
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  $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
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  $475,000 Sold Feb 18, 2025

  14 Twin Brooks Dr, Chester, NY 10918

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

  Last Sold Summary

  • 3% Below List Price
  • $281/SF
  • 50 Days On Market

  Current Estimated Value $499,311

  Last Listing Agent Layla Rose Boyles Century 21 Realty Center

  14 Twin Brooks Dr, Chester, NY 10918
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  Est $498,541 Not Listed For Sale

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

  201 Hambletonian Rd, Chester, NY 10918

  201 Hambletonian Rd, Chester, NY 10918
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  $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
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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 $553,598

  Last Listing Agent Donald Serotta Howard Hanna Rand Realty

  1 Winding Trail, Chester, NY 10918
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  Est $748,089 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,152 Sq Ft

  590 Craigville Rd, Chester, NY 10918

  590 Craigville Rd, Chester, NY 10918
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  $710,000 Pending

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

  1 Hillview Terrace, Chester, NY 10918

  BEAUTIFUL HOME - GREAT LOCATION.

  Sandra Cassio Robert DeFalco Realty, Inc.

  1 Hillview Terrace, Chester, NY 10918
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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 $607,626

  Last Listing Agent Dana Posner Howard Hanna Rand Realty

  411 Prospect Rd, Chester, NY 10918
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  Est $375,426 Not Listed For Sale

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

  4116 Whispering Hills, Chester, NY 10918

  4116 Whispering Hills, Chester, NY 10918
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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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  $525,000 Sold Jul 24, 2025

  11 Vista Dr, Chester, NY 10918

  • 4 Beds
  • 3 Baths
  • 2,122 Sq Ft
  • Built 1998

  Last Sold Summary

  • 2% Above List Price
  • $247/SF
  • 43 Days On Market

  Current Estimated Value $560,759

  Last Listing Agent James Feldhaus eXp Realty

  11 Vista Dr, Chester, NY 10918
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  Est $617,945 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,108 Sq Ft

  13 Townsend Place, Chester, NY 10918

  13 Townsend Place, Chester, NY 10918
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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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