Chester, NY Homes for Sale with Garage

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  $549,000

  $31K 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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  $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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  $725,000

  • 6 Beds
  • 3.5 Baths
  • 4,204 Sq Ft

  487 Black Meadow Rd, Chester, NY 10918

  A Landmark Farmhouse with a Story to Tell.Standing proudly since 1872, this historic Colonial farmhouse is one of the very first homes built on Black Meadow Road and remains a meaningful piece of Chester’s agricultural past. Once surrounded by hundreds of acres of open farmland and dairy cows, the home still carries the soul of a working farm while offering the comforts of modern living. With

  Dominic Santagato Joseph Baratta Company Realty

  487 Black Meadow 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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  $875,000

  • 4 Beds
  • 2.5 Baths
  • 3,656 Sq Ft

  49 Stone Mountain Trail, Chester, NY 10918

  Escape to your own private retreat at 49 Stone Mountain Trail. Tucked away on more than 7 acres with mountain views, this contemporary home delivers the perfect balance of comfort, space, and outdoor enjoyment. Imagine mornings filled with sunlight streaming through oversized windows, evenings gathered around the stone fireplace, and summers spent relaxing by the in-ground pool surrounded by

  Arya Rabinovits eRealty Advisors, Inc

  49 Stone Mountain Trail, Chester, NY 10918
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  $1,090,000

  • 4 Beds
  • 3.5 Baths
  • 4,130 Sq Ft

  102 Beverly Rd, Chester, NY 10918

  Located in the Warwick School district on a coveted street sits this larger than life home with impressive presence. The curved driveway welcomes you to the wide porch, perfect for rocking chairs and relaxing. The impressive entrance with custom stairway and window seat is just the first of impressive touches in this home. Large kitchen overlooks the yard and is well appointed with Thor

  Kimberly Corkum Keller Williams Realty

  102 Beverly Rd, Chester, NY 10918
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  $785,000

  $14K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 5,403 Sq Ft

  4 Debbie Ct, Chester, NY 10918

  Welcome to this exceptional private retreat nestled on beautifully landscaped grounds in desirable Chester. Offering the perfect blend of space, comfort, privacy, and lifestyle, this impressive property is surrounded by natural beauty while remaining conveniently close to shopping, dining, major highways, and the scenic Stewart State Forest. From the moment you arrive, you’ll appreciate the

  Joseph Rosenfeld Flag Realty Group

  4 Debbie Ct, Chester, NY 10918
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  $675,000

  $40K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,784 Sq Ft

  335 Laroe Rd, Chester, NY 10918

  Set on 3.2 acres within the Monroe-Woodbury School District, 335 Laroe Road offers a rare combination of space, functionality, and a convenient Chester location. Step inside to the welcoming two-story foyer featuring an open staircase and you'll immediately appreciate the size of the home. The main level offers a functional layout with multiple living spaces, including a living room, formal

  Christina D'Altiiio Coldwell Banker Choice Prop.

  335 Laroe Rd, Chester, NY 10918
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  $685,000

  $35K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,718 Sq Ft

  26 Bridle Ln, Chester, NY 10918

  From the moment you arrive, it's clear this is a home whose character and setting are best experienced firsthand. The bright, open-concept living area features vaulted ceilings and abundant natural light, creating an inviting space for everyday living and entertaining. A beautiful den with two walls of windows and a gas fireplace overlooks the pool and surrounding landscape. The thoughtfully

  David White Owner Entry.com

  26 Bridle Ln, Chester, NY 10918
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  $623,900

  $125K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,524 Sq Ft

  17 Woodridge Dr, Chester, NY 10918

  Beautiful Colonial set on just under an acre of meticulously landscaped property, offering breathtaking sunset views from a very private backyard. The taxes may be reduced by up to 20%; however, a tax appeal cannot be filed until 2027. Great spacious front porch! On a quiet cul-de-sac, this home features a stunning in-ground pool with a new heater, cover & pump. Pool filter, and liner are about 4

  Sharon Kushner eXp Realty

  17 Woodridge Dr, Chester, NY 10918
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  $185,000

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft

  28 Olmstedville Rd, Chester, NY 12817

  Older home in a completely private location - in the center of a Hamlet. Trees and bushes make the home invisible from the road. The back border is Town land with Public beach area on Trout Brook Good for canoeing. Covered porch is on two sides of the house. The interior has beautiful real wood floors. Main level is kitchen, dining room, living room, full bath and laundry area. Upstairs are 3

  Heidemarie Lane Big Hat Realty

  28 Olmstedville Rd, Chester, NY 12817
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  $499,000

  $30K PRICE DROP

  • 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 recreation 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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  $799,900

  Open Sun 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,715 Sq Ft

  176 Beverly Rd, Chester, NY 10918

  Welcome to 176 Beverly Road, Colonial-style nestled on 2.5 beautifully landscaped acres in the highly sought-after Warwick Valley School District. From the moment you arrive, you'll appreciate the home's curb appeal featuring custom stone entrance pillars with illuminated house numbers, a beautifully inlaid driveway address, professionally landscaped grounds accented by natural stone and

  Jocelyn Rivera

  176 Beverly Rd, Chester, NY 10918
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  $1,195,000

  • 4 Beds
  • 3.5 Baths
  • 4,281 Sq Ft

  22 Goshen Rd, Chester, NY 10918

  Welcome to an unparalleled expression of luxury living in the Town of Chester. Built in 2003, this custom-built Cape May/Colonial estate designed by award winning architect Larry Belk estate spans 4,281 square feet of meticulously designed living space, masterfully balancing grand entertaining spaces with intimate everyday comfort. From the moment you arrive, exceptional craftsmanship is on

  Martha Randazzo Howard Hanna Rand Realty

  22 Goshen Rd, Chester, NY 10918
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  $635,000

  Open Sun 2PM - 4PM

  • 4 Beds
  • 3 Baths
  • 3,636 Sq Ft

  10 Hidden Dr, Monroe, NY 10950

  Tucked away on over an acre with serene lake views and deeded lake rights, this spacious Monroe retreat offers the perfect blend of privacy, comfort, and lifestyle. Wake up to natural light pouring through oversized windows and start your day on the deck overlooking the water. Inside, you’ll find 3/4 generously sized bedrooms and 3 full baths, along with an updated kitchen and baths that bring a

  rosemary mcginn Century 21 Full Service Realty

  10 Hidden Dr, Monroe, NY 10950
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  $999,900

  $200K PRICE DROP

  • 4,032 Sq Ft

  206 Greycourt Rd, Chester, NY 10918

  INCREDIBLE PROPERTY!!! MUNICIPAL WATER!!! MONROE WOODBURY SCHOOL DISTRICT!!! Welcome to 206 Greycourt Road, Chester, NY A truly rare and remarkable offering in the heart of Orange County, Presenting an extraordinary opportunity to acquire a standout property with exceptional visibility, flexible “ OP” zoning, multiple structures, and limitless potential. Positioned on one of Chester's most highly

  Frank Muccari Cronin & Company Real Estate

  206 Greycourt Rd, Chester, NY 10918
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  $579,000

  Open Sat 11AM - 1PM

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

  152 Highland Ave, Monroe, NY 10950

  Impeccably maintained and lovingly cared for, this spacious 3-bedroom, 2-bath , 48 foot bi-level ranch offers comfort, functionality, and timeless appeal in one of Monroe’s desirable private cul-de-sac settings.Step inside to find bright, welcoming living spaces, generous room sizes, and beautiful hardwood floors that add warmth and character throughout much of the home. The inviting main

  Aja Marshall Krumpfer Realty Group, LLC

  152 Highland Ave, Monroe, NY 10950

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