Chester, NY Homes for Sale with Garage

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  $499,900

  $19K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft

  11 Oxford Depot, Chester, NY 10918

  Welcome to 11 Oxford Depot Rd, Chester, NY — a unique 3-bedroom, 2-bath home that perfectly blends charm, space, and modern updates. Featuring beautiful hardwood floors throughout, multiple living and entertaining areas, spacious bedrooms, updated bathrooms, and flexible bonus space ideal for a home office, playroom, or guest setup. The finished lower level adds even more versatility with

  Aneudy Rosa Keller Williams Realty

  11 Oxford Depot, Chester, NY 10918
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  $569,000

  $11K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,112 Sq Ft

  150 Lake Region Blvd, Monroe, NY 10950

  Welcome to 150 Lake Region Blvd, a beautifully maintained home in Monroe’s sought-after Lake Region / Walton Park community. Step inside to warm hardwood floors and a thoughtfully designed layout that feels both inviting and functional. The main living spaces flow effortlessly, creating an ideal setting for everyday living and entertaining. Offering 4 spacious bedrooms and 3 full bathrooms, the

  Pete Wolven Hudson Valley Home Connection

  150 Lake Region Blvd, Monroe, NY 10950
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  /50

  $1,725,000

  • 4 Beds
  • 2.5 Baths
  • 3,348 Sq Ft

  20 Goshen Rd, Chester, NY 10918

  THE ULTIMATE HUDSON VALLEY LEGACY ESTATE | 53 ACRES OF UNMATCHED POTENTIAL Rarely does a property emerge that perfectly balances refined luxury living with raw, untapped opportunity. Nestled in the heart of scenic Chester, New York, 20 Goshen Road offers an expansive 53-acre canvas designed for the visionary. Whether you envision a world-class equestrian facility, a high-potential residential

  Ramanjit Dhanoa eXp Realty

  20 Goshen Rd, Chester, NY 10918
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  $999,999

  • 5 Beds
  • 2.5 Baths
  • 4,772 Sq Ft

  2 Garnett Hill Rd, Chester, NY 10918

  A Private Suburban Retreat on Prestigious Garnet Hill. This Center Hall Colonial offers an exceptional residence- refined suburban living with the space, privacy, and sophistication sought by discerning buyers—just about an hour from Manhattan. Positioned on a beautifully landscaped 3+ acre property, the home features approximately over 4,700 square feet of elegant living space, offering 5

  Rachel Baruchov Platinum Realty Associates

  2 Garnett Hill Rd, Chester, NY 10918
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  $399,900

  $25K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,026 Sq Ft

  7 Hambletonian Ave, Chester, NY 10918

  Great new price! Come take a look at this 2 bedroom charmer with additional room offers potential 3+ bedrooms. Larger than it looks - need to see. Discover the timeless charm and surprising spaciousness of this delightful carriage house, set on a property rich with character and possibility. Step inside to a generous living room where a wood burning fireplace, hardwood floors, and a large bay

  William Scolza HomeSmart Homes & Estates

  7 Hambletonian Ave, Chester, NY 10918
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  $689,000

  $10K PRICE DROP

  • 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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  $319,900

  $4K PRICE INCREASE

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

  2820 Whispering Hills, Chester, NY 10918

  Lovely, Light and Airy 2 Bedroom 1 and 1/2 Bath Unit in Desireable Whispering Hills! Updated Kitchen and Bath, New Carpet and Freshly Painted. Downstairs has a Comfy Living Room with a Wood Burning Fireplace , Sunny Dining Room with Slider to a Patio, Convenient Galley Kitchen, Laundry Area and 1/2 Bath. Upstairs are a Spacious Primary Bedroom , Walkthrough Closet to Full Bath and a Roomy Second

  Anne Marie Scouarnec R2M Realty Inc.

  2820 Whispering Hills, 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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  $849,900

  $100K PRICE DROP

  • 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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  $529,000

  • 4 Beds
  • 2.5 Baths
  • 2,060 Sq Ft

  63 Hubshop Rd, Chester, NY 10918

  Nestled on a quiet road off the beaten path, this serene 4-bedroom, 2.5-bathroom Colonial offers the perfect blend of secluded tranquility and commuter convenience. The main level features a traditional layout with a spacious living room, formal dining room, and a cozy family room perfect for relaxing. The functional eat-in kitchen serves as the heart of the home, while all four bedrooms are

  Charles Moore Keller Williams Realty

  63 Hubshop Rd, Chester, NY 10918
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  $344,900

  $10K PRICE DROP

  • 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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