Chester, NY Homes for Sale

• 

  

  

  /29

  $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
• 

  

  

  /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
• 

  

  

  /35

  $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
• 

  

  

  /49

  $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
• 

  

  

  /26

  $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
• 

  

  /19

  $74,900

  $19K PRICE INCREASE

  • Land
  • 4.05 Acres
  • $18,494 per Acre

  85 Carriage Knoll Rd, Chester, NY 12817

  Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

  Walter Swartz Gallo Realty ADK Inc

  85 Carriage Knoll Rd, Chester, NY 12817
• 

  

  /21

  $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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  /35

  $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
• 

  

  /18

  $360,000

  • 3 Beds
  • 2.5 Baths
  • 1,585 Sq Ft

  154 Eagleton Dr, Monroe, NY 10950

  New Pics!Welcome to easy, low-maintenance living in this beautifully maintained 3-bedroom, 2.5-bath condo townhouse offering 1,585 square feet of comfortable living space in a peaceful community. Wake up to tranquil views overlooking a picturesque lake and enjoy the perfect blend of privacy, convenience, and amenities. The bright and spacious layout features central air conditioning, generous

  Bernadette Corrigan Keller Williams Realty

  154 Eagleton Dr, Monroe, NY 10950
• 

  

  /22

  $68,900

  $19K PRICE INCREASE

  • Land
  • 3.37 Acres
  • $20,445 per Acre

  86 Carriage Knoll Rd, Chester, NY 12817

  Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

  Walter Swartz Gallo Realty ADK Inc

  86 Carriage Knoll Rd, Chester, NY 12817
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  /10

  $119,995

  • Land
  • 30.95 Acres
  • $3,877 per Acre

  1.3 Cobble Creek Rd Unit 3, Chester, NY 12853

  Rarely does a property combine privacy, natural beauty and convenience as well as this 30-acre tract in Chester, New York. Located on a year-round town road, the land offers easy access while maintaining the peaceful feeling of a true Adirondack forest retreat. Several elevated APA-approved building sites are scattered throughout the property, offering ideal locations for an off-grid cabin or

  Marc Christmas CHRISTMAS AND ASSOCIATES INC

  1.3 Cobble Creek Rd Unit 3, Chester, NY 12853
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  /5

  $850,000

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

  5 Hilltop Ln, Chester, NY 10918

  Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new colonial-style residence invites you in with 12 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s kitchen. Every detail

  Moshe Kaufman MK Realty Inc

  5 Hilltop Ln, Chester, NY 10918
• 

  /2

  $750,000

  • 5 Beds
  • 2.5 Baths
  • 2,700 Sq Ft

  1 Hilltop Ln, Chester, NY 10918

  Welcome to your dream home in the exclusive Greens At Chester development! This stunning, brand new ready to move in colonial-style residence invites you in with 10 bright and airy rooms, soaring tall doors, and oversized windows that fill the space with natural light. Entertain guests in the beautiful dining room, relax in the expansive living area, and create memories in the updated chef’s

  Moshe Kaufman MK Realty Inc

  1 Hilltop Ln, Chester, NY 10918
• 

  /2

  $1,700,000

  • Land
  • 46.5 Acres
  • $36,559 per Acre

  0 Route 94 Unit KEY1023037, Blooming Grove, NY 10914

  Incredible opportunity to own approximately 55 acres of land being offered as a package with two adjoining parcels. This expansive property offers endless potential for investors, builders, or those seeking a private estate or recreational retreat. Preliminary information suggests the property may have the potential for approximately 400,000 square feet of warehouse space. Both parcels are being

  Lazar Schvimmer Mount Realty

  0 Route 94 Unit KEY1023037, Blooming Grove, NY 10914
• 

  

  /23

  $76,900

  $14K PRICE INCREASE

  • Land
  • 5.1 Acres
  • $15,078 per Acre

  112 Carriage Knoll Rd, Chester, NY 12817

  Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

  Walter Swartz Gallo Realty ADK Inc

  112 Carriage Knoll Rd, Chester, NY 12817
• 

  

  /4

  $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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  /10

  $37,500

  • Land
  • 1.62 Acres
  • $23,148 per Acre

  60 Carriage Knolls Rd, Chester, NY 12817

  Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for

  Walter Swartz Gallo Realty ADK Inc

  60 Carriage Knolls Rd, Chester, NY 12817
• 

  

  /36

  $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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  /49

  $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
• 

  

  /25

  $125,000

  • Land
  • 13.33 Acres
  • $9,377 per Acre

  L9 Byrd Pond, Chester, NY 12853

  Open walking trail around the property and very easy to navigate. Private 13+ acre building parcel just minutes from Gore Mountain and the conveniences of North Creek. The land is gently sloping with a roughed-in driveway/road already leading in from Bird Pond Road, offering a great head start for future access and site planning. Several attractive building locations can be found throughout the

  Walter Swartz Gallo Realty ADK Inc

  L9 Byrd Pond, Chester, NY 12853
• 

  

  /25

  $78,900

  $14K PRICE INCREASE

  • Land
  • 5.76 Acres
  • $13,698 per Acre

  106 Carriage Knoll Rd, Chester, NY 12817

  Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

  Walter Swartz Gallo Realty ADK Inc

  106 Carriage Knoll Rd, Chester, NY 12817
• 

  

  /4

  $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
• 

  

  /36

  $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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  /50

  $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
• 

  /2

  $649,999

  Coming Soon

  • 3 Beds
  • 3 Baths
  • 2,902 Sq Ft

  3561 State Route 94, Chester, NY 10918

  Showings begin on 8/28. More information and pics coming soon.

  Gina Dudgeon Howard Hanna Rand Realty

  3561 State Route 94, Chester, NY 10918
• 

  

  /38

  $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
• 

  

  /27

  $469,000

  • 3 Beds
  • 3 Baths
  • 1,357 Sq Ft

  70 Main St, Chester, NY 10918

  Welcome to 70 Main Street, a village gem situated right in the heart of historic Chester! This versatile 4-bedroom, 2.5-bathroom home combines classic architectural character with generous living spaces and modern convenience. The main residence features an inviting floor plan with bright, sunlit rooms and comfortable living areas throughout. A standout highlight of this property is the separate

  Pedro Garcia Curasi Realty, Inc.

  70 Main St, Chester, NY 10918
• 

  

  /29

  $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
• 

  /2

  $299,000

  $51K PRICE DROP

  • 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
• 

  

  /23

  $68,900

  $19K PRICE INCREASE

  • Land
  • 3.05 Acres
  • $22,590 per Acre

  82 Carriage Knoll Rd, Chester, NY 12817

  Seller financing now available with good credit!!! Beautiful park-like subdivision in a quiet neighborhood 5-minutes outside of Chestertown. Mostly wooded lots with each having unique ADK topography. Some fairly level with others being sloped or having raised areas perfect for a home or cabin. Must walk the properties to appreciate the beauty and serenity. Power and cable available at front of

  Walter Swartz Gallo Realty ADK Inc

  82 Carriage Knoll Rd, Chester, NY 12817
• 

  

  /7

  $39,500

  • Land
  • 2.38 Acres
  • $16,597 per Acre

  22 Carriage Knolls Rd, Chester, NY 12817

  Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for a

  Walter Swartz Gallo Realty ADK Inc

  22 Carriage Knolls Rd, Chester, NY 12817
• 

  

  /41

  $380,000

  • 2 Beds
  • 2 Baths
  • 1,350 Sq Ft

  4827 New York 8, Chester, NY 12817

  The perfect cottage for your Adirondack getaway or year-round living. Like new , move in condition. Features a cozy living room with electric fireplace, eat in kitchen w/ solid surface countertops & sliding doors opening to back deck, overlooking the large private backyard, Enjoy the evenings by the firepit. Radiant heated floors,. Full bath downstairs. Upstairs features a spacious primary

  Vickie Reed Hunt ERA

  4827 New York 8, Chester, NY 12817
• 

  

  /33

  $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
• 

  

  /39

  $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
• 

  

  /46

  $299,000

  • 3 Beds
  • 2.5 Baths
  • 1,320 Sq Ft

  607 Mountain Laurel Dr, Monroe, NY 10950

  Monroe-Woodbury Schools Townhouse with Low Taxes — Zoned for highly sought-after Pine Tree & Sapphire Elementary Schools. Step into this inviting 3-bedroom, 2.5-bath townhouse in the desirable Windridge community where space, light, and thoughtful updates come together. The spacious living room showcases younger laminate flooring that looks beautiful and cleans like a dream, while front-facing

  Rosalie Cook Weichert Realtors

  607 Mountain Laurel Dr, Monroe, NY 10950
• 

  

  /16

  $37,500

  • Land
  • 2 Acres
  • $18,750 per Acre

  13 Carriage Knolls Rd, Chester, NY 12817

  Seller financing available with good credit. These APA-approved lots are located in a beautiful, park-like subdivision just 5 minutes outside of Chestertown. Site plans and perc tests are complete, with electric and cable available at the road. The mostly wooded parcels each offer unique Adirondack topography—some fairly level, others featuring gentle slopes or elevated building areas ideal for a

  Walter Swartz Gallo Realty ADK Inc

  13 Carriage Knolls Rd, Chester, NY 12817
• 

  

  /49

  $389,000

  • 3 Beds
  • 1 Bath
  • 1,062 Sq Ft

  185 Oxford Rd, Chester, NY 10918

  Welcome to 185 Oxford Road, Chester! •••••This charming 3-bedroom Ranch home is now available for $389,000. Offering 1,062 sqft of comfortable one-level living on a generous 0.95-acre lot in the Monroe-Woodbury School District, this 1952-built home has been freshly painted and is move-in ready. •••••The interior features an open floorplan with beautiful knotted hardwood flooring, cathedral

  William Philip Keller Williams Hudson Valley

  185 Oxford Rd, Chester, NY 10918
• 

  

  /35

  $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
• 

  

  /50

  $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
• 

  /2

  $39,000

  • Land
  • 1.32 Acres
  • $29,545 per Acre

  L20 Granite Ridge Rd, Chester, NY 12817

  Beautiful 1.32 acre parcel in Adirondack Heights! APA approved Subdivision of Adirondack Heights with proposed home location that is already cleared with underground power! Close proximity to all your local lakes, hiking trails, Gore Mountain & Chestertown. Your Adirondack adventure awaits!

  Nancy Freebern Gallo Realty ADK Inc

  L20 Granite Ridge Rd, Chester, NY 12817

Showing Results 81 - 120, Page 3 of 4