Chester, NY Homes for Sale with Garage

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  $900,000

  • 4 Beds
  • 2.5 Baths
  • 2,588 Sq Ft

  60 Whitetail Run, Chester, NY 10918

  Beautifully maintained Colonial set on a picturesque and private property offering the perfect blend of comfort, space, This spacious home features an inviting layout with generously sized rooms, hardwood flooring, elegant moldings, and abundant natural light throughout. The heart of the home is the oversized eat-in kitchen with granite countertops, extensive cabinetry, pantry space, and

  Isaac Rottenberg Realty Blue Corp

  60 Whitetail Run, Chester, NY 10918
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  $545,000

  Open Sun 1PM - 3PM $70K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,908 Sq Ft

  11 Chandler Dr, Chester, NY 10918

  Welcome to this beautifully maintained raised ranch, perfectly situated on a desirable corner lot in Chester. This inviting 3-bedroom, 2 full and 1 half bath home blends comfort, style, and modern convenience in a location you'll love.Filled with natural light, the home features spacious living areas and a well-appointed kitchen with stainless steel appliances. The finished basement

  Daniella Restrepo Coldwell Banker Realty

  11 Chandler Dr, Chester, NY 10918
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  $849,900

  • 4 Beds
  • 3 Baths
  • 2,370 Sq Ft

  2 Primrose Ln, Chester, NY 10918

  Welcome to this stunning Colonial, perfectly blending comfort, style, and functionality. Offering 2,370 sq ft plus full walkout basement, this beautifully designed home features 4 spacious bedrooms and 3 full bathrooms, creating an inviting layout ideal for everyday living and entertaining.Step inside to a grand, sun-filled foyer with soaring ceilings that set the tone for the home’s warm and

  Janet Rendle Weichert Realtors

  2 Primrose Ln, Chester, NY 10918
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  $949,000

  $50K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,136 Sq Ft

  12 Damian Ct, Chester, NY 10918

  Welcome to 12 Damian Court, a spacious Colonial set on a quiet cul-de-sac. This well-maintained home offers 5 bedrooms and 4 bathrooms, with four bedrooms on the upper level and one additional bedroom in the finished basement. The main level features generous living and dining areas, perfect for everyday living and entertaining. The finished basement adds excellent flexibility with a second

  Elimelech Kremer MS Realty Group USA, Inc

  12 Damian Ct, Chester, NY 10918
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  $949,000

  • 4 Beds
  • 2.5 Baths
  • 3,332 Sq Ft

  19 Bull Mine Rd, Chester, NY 10918

  Set on 2.3 acres in Chester, this impressive property offers space, versatility, and scenic surroundings. The residence features approximately 3,332 square feet of living space with 4 bedrooms, 2 full baths and 1 half bath, thoughtfully designed for comfortable everyday living and entertaining. Interior highlights include generously sized living areas, a fireplace, abundant natural light, and

  James Cosenza BHG Real Estate Green Team

  19 Bull Mine Rd, Chester, NY 10918
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  $869,900

  New Construction

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

  10 Well Sweep Ln, 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

  10 Well Sweep Ln, Chester, NY 10918
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  /23

  $530,000

  $529K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,676 Sq Ft

  74 Heaton Rd, Monroe, NY 10950

  Step inside to hardwood floors and a welcoming eat-in kitchen featuring stainless steel appliances, ceramic tile flooring and soft-close cabinetry and drawers. Both full bathrooms have been beautifully updated with newer showers, tile and fixtures, plus the everyday luxury of HEATED FLOORS.The major improvements are already done: 200-amp electrical service (2025), rear property-line fencing

  Barbara Bloch Coldwell Banker Realty

  74 Heaton Rd, Monroe, NY 10950
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  /19

  $459,000

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

  63 Hubshop Rd, Chester, NY 10918

  Welcome Home to 63 Hubshop! This charming colonial boasts 2,100 square feet, 4 Bedrooms, 3 Bathrooms and sits on just under an acre of land. With a spacious kitchen, and both a designated living room and dining room, this home offers an easy-flowing layout, making you feel right at home the moment you walk through the door. Off the kitchen you will find a bonus room that can be transformed into a

  Ryan Barrett Keller Williams Realty

  63 Hubshop Rd, Chester, NY 10918
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  $549,999

  • 4 Beds
  • 2.5 Baths
  • 2,098 Sq Ft

  7 Lakeview Dr, Chester, NY 10918

  This charming updated 4-bedroom beauty in the Warwick School district offers a private and quiet setting featuring an above ground pool surrounded by a freshly painted deck just 3 minutes from Sugar Loaf Arts and Crafts Village. Its' kitchen has been upgraded boasting stainless steel appliances, granite countertops, and cherrywood cabinetry with undermount lighting and a wine/ beverage cooler.

  Sheyla Falesto Howard Hanna Rand Realty

  7 Lakeview Dr, Chester, NY 10918
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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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  $699,995

  $25K PRICE DROP

  • 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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  $379,900

  $45K 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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  $370,000

  • 3 Beds
  • 1 Bath
  • 1,561 Sq Ft

  33 Meadow Ave, Chester, NY 10918

  One floor living at it best! Walk out your front door, sit on your rocking chair front porch with your morning coffee & enjoy the mountain views! This 3 bedroom 1 bath ranch offers hardwood flooring throughout main living area & newly update kitchen and bath. Kitchen with plenty of cabinet & counter space. Entertain or BBQ on your private private deck. Plenty of parking in your 1 car garage. Walk

  Ernie Acampora River Realty Services, Inc.

  33 Meadow 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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  $675,000

  Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 3,202 Sq Ft

  188 Creamery Pond Rd, Chester, NY 10918

  The search for your DREAM HOME ends when you visit this property, since it will check all your boxes ! LOCATION which is perfect for commuters, just a few feet away from the charming Sugar Loaf Craft Village, situated between Warwick and Chester for your enjoyment and convenience of both town's amenities and activities. Corner lot, vinyl siding, deck overlooking the private backyard with a raised

  Patricia Brady Keller Williams Realty

  188 Creamery Pond 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

  Joseph Rosenfeld Flag Realty Group

  4 Debbie Ct, Chester, NY 10918
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  $300,000

  • 2 Beds
  • 1 Bath
  • 1,396 Sq Ft

  102 Hillcrest Ave, Monroe, NY 10950

  Situated in a quiet neighborhood on level corner property. House is in need of complete renovation. A suitable project for experienced contractor/builder.

  Rosy Wansor Wansor Realty

  102 Hillcrest Ave, Monroe, NY 10950
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  $799,000

  • 4 Beds
  • 2.5 Baths
  • 3,070 Sq Ft

  197 Oxford Rd, Chester, NY 10918

  Welcome to this beautifully charming Center Hall Colonial, privately set back from the road on a picturesque property with a tranquil man-made pond, fountain, and inviting wrap-around front porch. This spacious home offers the perfect balance of classic elegance and comfortable everyday living. The thoughtfully designed floor plan features a formal living room that flows seamlessly into the warm

  Regina Carmel Howard Hanna Rand Realty

  197 Oxford Rd, Chester, NY 10918
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  $799,000

  • 4 Beds
  • 2.5 Baths
  • 2,516 Sq Ft

  3 Garnett Hill Rd, Chester, NY 10918

  This well-maintained 4-bedroom, 2.5-bath home on 3 private acres is anchored by an expansive 3-tier Trex deck system and an on ground pool with 8-foot deep end, complemented by a sun deck and pool-surround walkway. The 2,516 square-foot home features 9-foot ceilings with wood molding, with hardwood floors and tile throughout the main floor. The main floor flows from a welcoming foyer through the

  Jacob Fried Keller Williams Realty

  3 Garnett Hill Rd, Chester, NY 10918
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  $575,000

  • 6 Beds
  • 2 Baths

  68 Conklingtown Rd Unit 1&2, Chester, NY 10918

  Rare opportunity. Come in and see this multi-family property in Chester, NY, and very close to main highways. This features 2 separate structures with their own utilities and natural gas. The main house presents 4 bedrooms, a kitchen, a dining room, and a living room with 1 full bath. main house is fully professional painted recently and now floors and roof on this house is 2 years old. The

  Moses Schreiber MS Realty Group USA, Inc

  68 Conklingtown Rd Unit 1&2, Chester, NY 10918
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  $550,000

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

  56 Poplar Dr, Monroe, NY 10950

  BiLevel/Raised Ranch on Quiet Street with Room to Grow! Come home and relax on the upper level deck overlooking state land that offers additional privacy. This well-maintained home clearly shows the pride of ownership. Open concept living room and dining room features many windows that fill the home with natural sunlight. Enjoy the convenience of the updated full bathroom and three comfortable

  Jeffrey Jacobsen Terrie OConnor

  56 Poplar Dr, Monroe, NY 10950
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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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  $699,900

  $77K PRICE DROP

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

  176 Beverly Rd, Chester, NY 10918

  Highly sought-after Warwick Schools, this Colonial offers curb appeal with custom stone entrance pillars featuring illuminated house numbers, an inlaid driveway address, professionally landscaped grounds accented by natural stone and in-ground lighting, and an insulated two-car carriage-style garage with glass doors. A grand two-story foyer with soaring ceilings, elegant wainscoting, and abundant

  David White Owner Entry.com

  176 Beverly Rd, Chester, NY 10918
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  $369,000

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

  2522 Whispering Hills Unit 518, Chester, NY 10918

  Welcome to Whispering Hills! Discover easy living, comfort and privacy while living within a neighborhood community. Perfect for first time home buyers or if you're downsizing for care free, low maintenance living. Enjoy this spacious 3 bedroom, 3 bath townhouse with lots of storage and your private garage with direct entry into your home. Comfortable and spacious bedroom layouts with baths and

  Ann Marie Silvani Howard Hanna Rand Realty

  2522 Whispering Hills Unit 518, 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

  • 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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  $570,000

  $9K PRICE DROP

  • 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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