Chester Homes for Sale

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  $460,000

  • 3 Beds
  • 1.5 Baths
  • 1,728 Sq Ft

  1367 Kings Hwy, Chester, NY 10918

  Historic Colonial Era Home in the Heart of Sugar Loaf, NYLocated just 60 minutes from NYCZoned Residential/CommercialStep into history with this one-of-a-kind 1,750 sq. ft. Colonial era home, where 18th-century charm meets 21st-century opportunity — right in the heart of the artisan hamlet of Sugar Loaf, NY. Original building was built in 1770, this unique property features:• One

  Mark Karten Karten Real Estate Svcs LLC

  1367 Kings Hwy, Chester, NY 10918
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  $875,000

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

  2 Pine Hill Rd, Chester, NY 10918

  The Conklin House: A Masterpiece of History & Modern Luxury. Experience the perfect blend of early 20th-century charm and 21st-century comfort. The Conklin House, a classic 1908 Queen Anne Victorian, stands as a commanding presence at the edge of the historic Village of Sugar Loaf. The home has always been used residentially but zoning permits commercial usage as well. Originally ordered from the

  Richard Ellis Ellis Sotheby's Intl Realty

  2 Pine Hill Rd, Chester, NY 10918
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  $425,000

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

  40 Poplar Dr, Monroe, NY 10950

  -----Best Value in Monroe — Updated Ranch on Quiet Street with Room to Grow! There may be no better house for the money in Monroe. This adorable, well-maintained ranch clearly shows the pride of ownership from 16 years of loving care. A brand-new front entrance door welcomes you into a bright foyer and spacious living room featuring a large picture window that fills the home with natural

  Richard Froehlich RE/MAX Benchmark Realty Group

  40 Poplar Dr, Monroe, NY 10950
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  $1,195,000 Open Sun 11AM - 1PM

  • 9 Beds
  • 6 Baths
  • 4,965 Sq Ft

  19 High St, Chester, NY 10918

  Own a true piece of American history with the iconic Hambletonian House, a one-of-a-kind Victorian estate built in the 19th century by William Rysdyk, original owner of Hambletonian 10—the legendary sire that shaped nearly all modern Standardbred racehorses. Perfectly positioned on nearly three private acres atop a knoll in the heart of Chester, New York, this meticulously maintained property

  Beth Palma Keller Williams Realty

  19 High St, Chester, NY 10918
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  $599,000

  • 4 Beds
  • 2 Baths
  • 2,056 Sq Ft

  6 Adams Ct, Monroe, NY 10950

  Stunning Split Ranch with Pool and Gorgeous Curb Appeal, Located in the Town of Chester within the Monroe-Woodbury School District Welcome to this beautifully maintained 4-bedroom, 2 full bath split ranch offering the perfect blend of comfort, style, and functionality. The upper level features a spacious and sun-filled eat-in kitchen, ideal for everyday living, with direct access to a big Trex

  Ida Payne Keller Williams Realty

  6 Adams Ct, Monroe, NY 10950
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  $299,000

  • Land
  • 5.7 Acres
  • $52,456 per Acre

  552 Pine Hill Rd, Chester, NY 10918

  Beautiful 5.7-acre residential parcel located in the Town of chester, offering an exceptional opportunity to build your custom dream home in a peaceful, private setting. With ample space for a spacious residence and outdoor living areas (subject to town approvals), this property combines natural surroundings with convenient access to nearby amenities, schools, and major roadways. Adjacent to 558

  Charnie Guttmann eRealty Advisors, Inc

  552 Pine Hill Rd, Chester, NY 10918
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  $485,000

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

  35 Maple Ln, Monroe, NY 10950

  Is there a 3-bed ranch in Monroe NY under $500K with a finished basement, pool, and commuter convenience? 35 Maple Ln is a 3-bedroom, 2-bathroom ranch offered at $499,999 with 1,460 sq ft of living space, including 960 sq ft above grade and a 500 sq ft finished basement. Built in 1964, this single family residence offers true single level living plus flexible lower level space ideal for

  Kewin Garabito eXp Realty

  35 Maple Ln, Monroe, NY 10950
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  $849,900

  • 4 Beds
  • 2.5 Baths
  • 2,603 Sq Ft

  32 Mountainside Dr, Chester, NY 10918

  A RARE OPPORTUNITY to build your CUSTOM DREAM HOME on over 20 private acres in the sought-after Cooper's Ridge sub-division! This will truly be a lovely property with land, privacy and wonderful mountain views! This modern farm house cape features over 2,600 sq ft. and is completely CUSTOM and DELIVERED TURN-KEY ... build this home, or bring your own dream plans/ideas! This ONE LEVEL living

  Karen Gauvin Our House Real Estate Group

  32 Mountainside Dr, Chester, NY 10918
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  $344,900

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

  1311 Whispering Hills Unit 96, Chester, NY 10918

  Experience Elevated Living: Your Private Hudson Valley Retreat at 1311 Whispering Hills Welcome to a home that offers more than just square footage—it offers a lifestyle change. Nestled in the scenic rolling hills of Orange County, 1311 Whispering Hills is a masterclass in modern suburban living. This meticulously maintained residence captures the essence of "home" from the moment you step

  Michael Jenney Keller Williams Realty

  1311 Whispering Hills Unit 96, Chester, NY 10918
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  $735,000

  • 4 Beds
  • 3.5 Baths
  • 3,356 Sq Ft

  55 Beverly Rd, Chester, NY 10918

  Welcome to 55 Beverly Road, Chester—A Stunning, Move-In Ready Home This beautifully updated 3,156 square-foot home blends timeless charm with modern upgrades, offering space, comfort, and style throughout. The expansive floor plan features bright, inviting living areas with soaring vaulted ceilings, gleaming hardwood floors throughout, and a cozy masonry fireplace that serves as a perfect focal

  Jay Himelson Howard Hanna Rand Realty

  55 Beverly Rd, Chester, NY 10918
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  $225,000

  • Land
  • 1 Acre
  • $225,000 per Acre

  34 Mountainside Dr, Chester, NY 10918

  Lovely 1-Acre lot w/MOUNTAIN VIEWS & NATURAL GAS in a beautiful newly built SUB-DIVISION. Build out this nearly completely built lovely sub-division, curb-cuts, paved road sloping lot perfect for a WALK-OUT BASEMENT and DECKS FOR BEAUTIFUL VIEWS ... FULLY APPROVED LOT, ESTABLISHED NEIGHBORHOOD, VERY COMMUTABLE location! Close to the vibrant shopping, restaurants, nightlife, shows/events at Sugar

  Karen Gauvin Our House Real Estate Group

  34 Mountainside Dr, Chester, NY 10918

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