71

Chester, NY Homes for Sale

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  • 7 Park Place, Chester, NY 10918
    7 Park Place, Chester, NY 10918
    7 Park Place, Chester, NY 10918
    /48

    $730,000

    • 4 Beds
    • 3.5 Baths
    • 2,780 Sq Ft

    7 Park Place, Chester, NY 10918

    Welcome to your private, wooded oasis! This charming home perfectly blends convenience with comfort, featuring an ideal layout for multi-generational living or guests with two bedrooms and a full bathroom on the main floor. A cozy wood insert is the heart of the main living space, creating both warmth and a wonderful ambiance on chilly evenings. Beyond the existing bedrooms, there is additional

    Agent Photo

    Luanne McGann

    Century 21 Full Service Realty

    (845) 447-0221

    7 Park Place, Chester, NY 10918
  • 5 Gabriels Dr, Chester, NY 10918
    5 Gabriels Dr, Chester, NY 10918
    5 Gabriels Dr, Chester, NY 10918
    /49

    $899,000

    • 4 Beds
    • 2.5 Baths
    • 2,722 Sq Ft

    5 Gabriels Dr, Chester, NY 10918

    Exquisite 4 bedroom 3 bath colonial , timeless grandeur meets modern luxury nestled gracefully on a private cul de sac. Amidst meticulously manicured grounds, this colonial style home offers an unparalleled blend of classic elegance and contemporary comfort, from the moment you approach the stately wrought iron fenced property and are greeted by a wrap around porch, you are welcomed by a grand

    Claudia Lepore Keller Williams Realty

    5 Gabriels Dr, Chester, NY 10918
  • 34 Mountainside Dr, Chester, NY 10918
    34 Mountainside Dr, Chester, NY 10918
    34 Mountainside Dr, Chester, NY 10918
    /8

    $699,990

    • 4 Beds
    • 3 Baths
    • 1,867 Sq Ft

    34 Mountainside Dr, Chester, NY 10918

    ONE LEVEL LIVING/ EASY COMMUTE- with additional space upstairs and down! ... Don't miss this beautiful TURN-KEY Arts & Crafts-style FARMHOUSE TO BE BUILT! ..... COME AND FULLY CUSTOMIZE this 4-bdrm, 3 bath, 2,106+/- sq. ft home (including bonus room)! LARGE MAIN FLOOR PRIMARY BEDROOM with ENSUITE BATH & WALK-IN CLOSET plus A SECOND MAIN FLOOR BEDROOM (NURSERY, OFFICE, CRAFT ROOM ETC.). FANTASTIC

    Karen Gauvin Our House Real Estate Group

    34 Mountainside Dr, Chester, NY 10918
  • 2 Garnett Hill Rd, Chester, NY 10918
    2 Garnett Hill Rd, Chester, NY 10918
    2 Garnett Hill Rd, Chester, NY 10918
    /35

    $999,999

    • 5 Beds
    • 3.5 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
  • 2 Pine Hill Rd, Chester, NY 10918
    2 Pine Hill Rd, Chester, NY 10918
    2 Pine Hill Rd, Chester, NY 10918
    /31

    $875,000

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

    2 Pine Hill Rd, Chester, NY 10918

    Listed on the National Register of Historic Places in the Sugar Loaf Historic District, this stunning Victorian is a Circa 1910 Sears Roebuck Kit Home (#118 The Clyde). Not only is this your dream home located in beautiful Sugar Loaf, NY, it is also zoned for extensive commercial use. Just a 1-minute walk to the quaint Sugar Loaf Arts & Crafts Village, cafes and Sugar Loaf Performing Arts Center.

    Debbie Walsh SHAHAR Management LLC

    2 Pine Hill Rd, Chester, NY 10918
  • 651 Lakes Rd, Monroe, NY 10950
    651 Lakes Rd, Monroe, NY 10950
    651 Lakes Rd, Monroe, NY 10950
    /7

    $874,400

    • 4 Beds
    • 2 Baths
    • 2,466 Sq Ft

    651 Lakes Rd, Monroe, NY 10950

    Rare opportunity to purchase this gorgeous property that consists of 3 homes nestled on 3.5 beautiful acres. The main Colonial residence has been gutted and will need to be renovated/rebuilt, however, you can live in one of the additional two residences while you renovate! The 2nd residence called the “stone cottage” has 2 fieldstone fireplaces, a full kitchen, a vaulted ceiling in the bedroom, a

    Frank Golio Howard Hanna Rand Realty

    651 Lakes Rd, Monroe, NY 10950
  • 53 Odyssey Dr, Chester, NY 10918
    53 Odyssey Dr, Chester, NY 10918
    53 Odyssey Dr, Chester, NY 10918
    /48

    $1,100,000

    • 4 Beds
    • 3.5 Baths
    • 4,467 Sq Ft

    53 Odyssey Dr, Chester, NY 10918

    Welcome to an extraordinary 4,400+ square foot residence in the coveted Warwick School district, where luxury and lifestyle converge to create the ultimate entertainer’s dream. This meticulously maintained and thoughtfully updated home offers breathtaking panoramic views, inviting you to unwind in the serene front atrium or the sun-drenched sunroom at the rear. Step inside to discover a

    Hilary Ryan Goldman Howard Hanna Rand Realty

    53 Odyssey Dr, Chester, NY 10918
  • 101 Oxford Rd, Chester, NY 10918
    101 Oxford Rd, Chester, NY 10918
    /2

    $669,000

    • 3 Beds
    • 1.5 Baths
    • 1,816 Sq Ft

    101 Oxford Rd, Chester, NY 10918

    This nice quiet house is a great place to call home. With almost 11 acres of land, there's a lot of space to enjoy activities and outdoor fun. The first floor of the house offers a nice layout with big living room, family room, kitchen, dining room, and a half bath. and a washer and dryer room . Bedrooms are nice and big making it very comfortable . The house will need some TLC and will need

    Nathan Landau Loop Realty Inc

    101 Oxford Rd, Chester, NY 10918
  • 9 Country Woods Dr, Chester, NY 10918
    9 Country Woods Dr, Chester, NY 10918
    9 Country Woods Dr, Chester, NY 10918
    /30

    $725,000

    • 5 Beds
    • 2.5 Baths
    • 3,124 Sq Ft

    9 Country Woods Dr, Chester, NY 10918

    Thoughtfully repositioned with a nearly $15,000 price adjustment makes this Country Woods colonial an unbeatable value! Now priced to allow for updates while securing a prime location, generous living space, a beautiful setting, and room to add your personal style. Country Woods is one of Chester’s most sought-after neighborhoods. This handsome Colonial sits on 1.7 landscaped acres and offers

    Kimberly Starks Howard Hanna Rand Realty

    9 Country Woods Dr, Chester, NY 10918
  • 487 Black Meadow Rd, Chester, NY 10918
    487 Black Meadow Rd, Chester, NY 10918
    487 Black Meadow Rd, Chester, NY 10918
    /30

    $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
  • 5 Bens Way, Chester, NY 10918
    5 Bens Way, Chester, NY 10918
    5 Bens Way, Chester, NY 10918
    /28

    $744,999 Open Sat 10AM - 12PM

    • 4 Beds
    • 2.5 Baths
    • 2,544 Sq Ft

    5 Bens Way, Chester, NY 10918

    Welcome to 5 Bens Way, a beautifully positioned residence tucked away on a quiet cul-de-sac in the highly sought-after Town of Chester, New York. This property offers an exceptional blend of privacy, space, and convenience, making it an outstanding opportunity for buyers seeking a well-rounded Hudson Valley lifestyle with easy access to modern amenities, commuter routes, and recreational

    Anthony Rivas Keller Williams Hudson Valley

    5 Bens Way, Chester, NY 10918
  • 360 Prospect Rd, Chester, NY 10918
    360 Prospect Rd, Chester, NY 10918
    360 Prospect Rd, Chester, NY 10918
    /50

    $699,000

    • 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
  • 34 Booth Rd, Chester, NY 10918
    34 Booth Rd, Chester, NY 10918
    34 Booth Rd, Chester, NY 10918
    /42

    $720,000

    • 4 Beds
    • 2.5 Baths
    • 2,506 Sq Ft

    34 Booth Rd, Chester, NY 10918

    Updated 4BR Colonial in Chester – Monroe-Woodbury Schools! Welcome home to this beautifully maintained 4-bedroom, 3-bath Colonial offering timeless style, functional space, and significant updates in the highly sought-after Monroe-Woodbury Central School District! A grand two-story entry foyer with a dramatic cathedral ceiling makes an impressive first impression, filling the home with natural

    Kristie Jacques Century 21 Full Service Realty

    34 Booth Rd, Chester, NY 10918
  • 16 Oxford Springs Rd, Chester, NY 10918
    16 Oxford Springs Rd, Chester, NY 10918
    16 Oxford Springs Rd, Chester, NY 10918
    /48

    $750,000

    • 3 Beds
    • 3 Baths
    • 2,870 Sq Ft

    16 Oxford Springs Rd, Chester, NY 10918

    Discover modern living at its best in this beautifully designed 2,870 sq ft contemporary home with flexible floor plan and wonderful tranquility! Set on 4.1 private acres and featuring its own pond and seasonal babbling brook, 16 Oxford Springs Road is perfect for those seeking a full-time residence or Hudson Valley getaway. This home offers retreat-like privacy yet is only minutes to all

    Jennifer Gold RE/MAX Benchmark Realty Group

    16 Oxford Springs Rd, Chester, NY 10918
  • 83 Lake Region Blvd, Monroe, NY 10950
    83 Lake Region Blvd, Monroe, NY 10950
    83 Lake Region Blvd, Monroe, NY 10950
    /42

    $725,890

    • 3 Beds
    • 2.5 Baths
    • 1,793 Sq Ft

    83 Lake Region Blvd, Monroe, NY 10950

    A gardeners and vacationers paradise. Look no further than a vacation in your backyard with a fully 6ft fenced in yard throughout most and a 4ft fenced in section behind thee greenhouse with 4 gates of access. Two driveways with plenty of parking! A small pond with frogs, a wooden bridge, water lilies, rocks and beautiful landscape that will soothe your soul. Over 20 fruit trees and bushes

    Wendy Todoric Keller Williams Realty

    83 Lake Region Blvd, Monroe, NY 10950
  • 108 Pine Hill Rd, Chester, NY 10918
    108 Pine Hill Rd, Chester, NY 10918
    108 Pine Hill Rd, Chester, NY 10918
    /37

    $449,000

    • 4 Beds
    • 1.5 Baths
    • 1,780 Sq Ft

    108 Pine Hill Rd, Chester, NY 10918

    Welcome to your dream home at 108 Pine Hill Rd, Chester, NY, where comfort meets elegance in a spacious single-family abode. This charming home offers a thoughtfully designed layout, featuring a welcoming kitchen with direct outdoor access, perfect for morning coffees or entertaining. The first floor also hosts a cozy living room and a bright family room, both filled with natural light. Upstairs,

    Avi Samet Avion

    108 Pine Hill Rd, Chester, NY 10918
  • 15 Deer Run, Chester, NY 12817
    15 Deer Run, Chester, NY 12817
    15 Deer Run, Chester, NY 12817
    /5

    $54,900

    • Land
    • 10.14 Acres
    • $5,414 per Acre

    15 Deer Run, Chester, NY 12817

    10+ Acre recreational vacation location in the Town of Chester. Private maintained road with nice camps and homes. The lot feels as if its set in the heart of a wildlife preserve. Small non salvageable cabin on the property that had electric to the site. 6 miles to North Creek the home of Gore Mountain Ski Center. Build your vacation home here in the Adirondacks.

    Patricia Seitz McAlonen Pearsall Realty

    15 Deer Run, Chester, NY 12817
  • 72 Carriage Knoll Rd, Chester, NY 12817
    72 Carriage Knoll Rd, Chester, NY 12817
    72 Carriage Knoll Rd, Chester, NY 12817
    /23

    $68,900

    • Land
    • 3.11 Acres
    • $22,154 per Acre

    72 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

    72 Carriage Knoll Rd, Chester, NY 12817
  • 70 Main St, Chester, NY 10918
    70 Main St, Chester, NY 10918
    70 Main St, Chester, NY 10918
    /23

    $475,000

    • 4 Beds
    • 2.5 Baths
    • 1,357 Sq Ft

    70 Main St, Chester, NY 10918

    Discover the perfect blend of versatility and charm with this exceptional property. The main house offers three levels of comfortable living, including four bedrooms, three baths, and a spacious kitchen ideal for gathering and entertaining. The thoughtfully renovated barn extends your options with beautifully finished space that carries rustic character alongside modern updates. Whether you

    Kassandra Mott Keller Williams Hudson Valley

    70 Main St, Chester, NY 10918
  • 71 Carriage Knoll Rd, Chester, NY 12817
    71 Carriage Knoll Rd, Chester, NY 12817
    71 Carriage Knoll Rd, Chester, NY 12817
    /17

    $59,900

    • Land
    • 1.89 Acres
    • $31,693 per Acre

    71 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

    71 Carriage Knoll Rd, Chester, NY 12817
  • 32 Mountainside Dr, Chester, NY 10918
    32 Mountainside Dr, Chester, NY 10918
    32 Mountainside Dr, Chester, NY 10918
    /5

    $259,000

    • Land
    • 20.18 Acres
    • $12,834 per Acre

    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 can truly be a mini-estate with near full privacy plus MOUNTAIN VIEWS!! FULLY ENGINEERED with NATURAL GAS, curb cuts! .... Site map in photos. This is one of only two remaining lots. Some wet-lands on the property. Drive way is not shared - it will be side-by-side with

    Karen Gauvin Our House Real Estate Group

    32 Mountainside Dr, Chester, NY 10918
  • 77 Carriage Knoll Rd, Chester, NY 12817
    77 Carriage Knoll Rd, Chester, NY 12817
    77 Carriage Knoll Rd, Chester, NY 12817
    /19

    $74,900

    • Land
    • 4.17 Acres
    • $17,962 per Acre

    77 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

    77 Carriage Knoll Rd, Chester, NY 12817
  • 62 Carriage Knolls Rd, Chester, NY 12817
    62 Carriage Knolls Rd, Chester, NY 12817
    62 Carriage Knolls Rd, Chester, NY 12817
    /23

    $62,000

    • Land
    • 11.11 Acres
    • $5,581 per Acre

    62 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

    62 Carriage Knolls Rd, Chester, NY 12817
  • 71 Greycourt Rd, Chester, NY 10918
    71 Greycourt Rd, Chester, NY 10918
    71 Greycourt Rd, Chester, NY 10918
    /38

    $449,000

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft

    71 Greycourt Rd, Chester, NY 10918

    Discover comfort, privacy, and convenience in this beautifully maintained home set on a 2 acre property. Located in a peaceful area, this residence offers a warm and inviting layout with a nicely sized kitchen, three comfortable bedrooms, and two well kept bathrooms.The outdoors is offering a stunning fenced backyard, lots of playground space for entertainment. Minutes to all major highways

    Lazar Schvimmer Blooming Realty

    71 Greycourt Rd, Chester, NY 10918
  • 503 Mountain Laurel Dr, Monroe, NY 10950
    503 Mountain Laurel Dr, Monroe, NY 10950
    503 Mountain Laurel Dr, Monroe, NY 10950
    /11

    $261,250

    • 2 Beds
    • 1.5 Baths
    • 1,240 Sq Ft

    503 Mountain Laurel Dr, Monroe, NY 10950

    Two story center unit with full basement located in Windridge community. Primary bedroom has large sitting area which can be used as home office. Sliders to rear patio with lake views!! Large living and dining area. Beautiful complex with mountain views.

    Margaret Galatro ARC Realty 1 in Sales

    503 Mountain Laurel Dr, Monroe, NY 10950
  • 33 Meadow Ave, Chester, NY 10918
    33 Meadow Ave, Chester, NY 10918
    33 Meadow Ave, Chester, NY 10918
    /23

    $430,000

    • 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
  • 20 Carriage Knolls Rd, Chester, NY 12817
    20 Carriage Knolls Rd, Chester, NY 12817
    20 Carriage Knolls Rd, Chester, NY 12817
    /7

    $49,500

    • Land
    • 3.36 Acres
    • $14,732 per Acre

    20 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

    20 Carriage Knolls Rd, Chester, NY 12817
  • 607 Mountain Laurel Dr, Monroe, NY 10950
    607 Mountain Laurel Dr, Monroe, NY 10950
    607 Mountain Laurel Dr, Monroe, NY 10950
    /39

    $339,900

    • 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
  • 37 Main St, Chester, NY 10918
    37 Main St, Chester, NY 10918
    37 Main St, Chester, NY 10918
    /28

    $1,498,888

    • 4 Beds
    • 4 Baths
    • 7,308 Sq Ft

    37 Main St, Chester, NY 10918

    Prime Investment Opportunity in the Heart of Chester Village – 37-39 Main Street & 9 Bank Street Nestled in the charming and historic Village of Chester, this fully updated mixed-use property presents an exceptional investment opportunity. Originally built in 1935, this rustic yet modernized building seamlessly blends timeless character with contemporary upgrades. The property features:•

    James Feldhaus eXp Realty

    37 Main St, Chester, NY 10918
  • L 13.2 Friends Lake Rd, Chester, NY 12817
    L 13.2 Friends Lake Rd, Chester, NY 12817
    L 13.2 Friends Lake Rd, Chester, NY 12817
    /78

    $699,900

    • Land
    • 337 Acres
    • $2,077 per Acre

    L 13.2 Friends Lake Rd, Chester, NY 12817

    2,200 feet of frontage along the Upper Hudson River, a wild, whitewater backcountry river, and immediate access to nearly 1,600 acres of State Forest Preserve, the Hudson River Woods & Wildwater property is the ''complete package'' of Adirondack property. With over 4,500 feet of road frontage (with electric) on Friends Lake Road, it's an ideal location for a camp, second home, or subdivision.

    John O'Donnell Timberland Realty

    L 13.2 Friends Lake Rd, Chester, NY 12817
  • L9 Bird Pond Rd, Chester, NY 12853
    L9 Bird Pond Rd, Chester, NY 12853
    L9 Bird Pond Rd, Chester, NY 12853
    /27

    $129,000

    • Land
    • 13.33 Acres
    • $9,677 per Acre

    L9 Bird Pond Rd, Chester, NY 12853

    Private 13+ acres of gently sloping land just minutes from Gore Mountain. Roughed-in driveway/Road leading from Bird Pond Rd. Several nice building locations around the property. One house-site staked-out for reference. Possible views from higher on the property with some select clearing. Listing agent will provide one set of existing preliminary building plans for the future homeowner from

    Walter Swartz Gallo Realty ADK Inc

    L9 Bird Pond Rd, Chester, NY 12853
  • 111 Lake Region Blvd, Monroe, NY 10950
    111 Lake Region Blvd, Monroe, NY 10950
    111 Lake Region Blvd, Monroe, NY 10950
    /22

    $309,900

    • 2 Beds
    • 1 Bath
    • 792 Sq Ft

    111 Lake Region Blvd, Monroe, NY 10950

    Charming 2BR/1BA ranch on a level lot featuring an oversized detached 2-car garage and rear deck. Bright eat-in kitchen with ample cabinetry and vinyl plank flooring. Rear deck overlooks a spacious, usable yard—ideal for outdoor enjoyment. Convenient location close to shopping, schools, and major commuter routes. Great opportunity for owner-occupants or investors alike.

    Donna Ramundo Keller Williams Valley Realty

    111 Lake Region Blvd, Monroe, NY 10950
  • 0 Main St, Chester, NY 10918
    0 Main St, Chester, NY 10918
    /2

    $500,000

    • Land
    • 0.83 Acre
    • $603,355 per Acre

    0 Main St, Chester, NY 10918

    Open commercial lot directly behind the existing Cumberland Farms and just to the east of the former Brookside carwash. Good use may be for a parking lot for a building built on 42 Brookside.

    Claude Brischoux Keller Williams Realty

    0 Main St, Chester, NY 10918
  • 8 Camelback Rd, Chester, NY 10918
    8 Camelback Rd, Chester, NY 10918
    8 Camelback Rd, Chester, NY 10918
    /11

    $349,999

    • Land
    • 4.9 Acres
    • $71,428 per Acre

    8 Camelback Rd, Chester, NY 10918

    Nestled at the end of a private cul-de-sac, this 5 acre homesite offers breathtaking mountain and valley views in the sought-after Bull Mill Road area of Monroe/Chester, NY. The property’s gentle slopes create the perfect opportunity for a walkout lower level, allowing you to capture spectacular sunsets. This shovel-ready, fully approved, and engineered building lot features Belgian block

    James Feldhaus eXp Realty

    8 Camelback Rd, Chester, NY 10918
  • 98 Carriage Knoll Rd, Chester, NY 12817
    98 Carriage Knoll Rd, Chester, NY 12817
    98 Carriage Knoll Rd, Chester, NY 12817
    /20

    $68,900

    • Land
    • 3.26 Acres
    • $21,135 per Acre

    98 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

    98 Carriage Knoll Rd, Chester, NY 12817
  • 220 Oxford Rd, Chester, NY 10918
    220 Oxford Rd, Chester, NY 10918
    /2

    $350,000

    • Land
    • 2 Acres
    • $175,000 per Acre

    220 Oxford Rd, Chester, NY 10918

    A rare opportunity in Blooming Grove! This beautiful and flat 2-acre property offers endless potential in a calm and peaceful setting with a road frontage. Conveniently located just minutes from Prospect Garden, the land sits within the Monroe-Woodbury School District. With easy access to permits, this property is ideal for building your dream home or future investment. The neighborhood holds

    Chaim Weiss Exit Realty Venture

    220 Oxford Rd, Chester, NY 10918
  • 30 Harding Way, Chester, NY 10950
    30 Harding Way, Chester, NY 10950
    30 Harding Way, Chester, NY 10950
    /7

    $500,000

    • Land
    • 9.78 Acres
    • $51,125 per Acre

    30 Harding Way, Chester, NY 10950

    An exceptional opportunity for builders and investors in the highly desirable Town of Chester and Town of Monroe, within the Monroe–Woodbury School District. This offering includes four contiguous lots for the price of one, providing significant development potential. The assemblage consists of 30 Harding Way (0.18 acres; Section 27, Block 3, Lot 11), sold together with the adjoining parcels: Lot

    Ida Payne Keller Williams Realty

    30 Harding Way, Chester, NY 10950
  • L62.2 Moffitt Rd, Chester, NY 12817
    L62.2 Moffitt Rd, Chester, NY 12817
    L62.2 Moffitt Rd, Chester, NY 12817
    /3

    $75,000

    • Land
    • 12 Acres
    • $6,250 per Acre

    L62.2 Moffitt Rd, Chester, NY 12817

    12-acre parcel offering beautiful terrain and privacy, yet on a town-maintained road. Plenty of options for a home setting. A very desirable property for your future home construction. Only 15 minutes to Gore Mountain Ski Area, 3 miles to Loon Lake and within a mile of the Hudson River. A wonderful opportunity to enjoy the Adirondack experience. $75,000

    Carol Monroe Najer Realty

    L62.2 Moffitt Rd, Chester, NY 12817
  • 34 Carriage Knolls Rd, Chester, NY 12817
    34 Carriage Knolls Rd, Chester, NY 12817
    34 Carriage Knolls Rd, Chester, NY 12817
    /8

    $39,500

    • Land
    • 1.82 Acres
    • $21,703 per Acre

    34 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

    34 Carriage Knolls Rd, Chester, NY 12817
  • 2948 State Route 94, Chester, NY 10918
    2948 State Route 94, Chester, NY 10918
    2948 State Route 94, Chester, NY 10918
    /45

    $1,395,000

    • 4 Beds
    • 2.5 Baths
    • 3,866 Sq Ft

    2948 State Route 94, Chester, NY 10918

    Set atop a gentle hill with sweeping eastern views of Round Hill and Schunnemunk Ridge, this pristine 1860 farmhouse blends preserved historic character with thoughtful modern updates. Originally part of the Sears family dairy pasture, the 3,866 sq ft home has been meticulously maintained and features original wide-plank hardwood floors, a striking hand-carved banister, five fireplaces with

    Elizabeth Broderick Tuxedo Hudson Realty Corp

    2948 State Route 94, Chester, NY 10918

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New York Orange County Chester

Real Estate & Homes for Sale in Chester, NY

Why Live in Chester

Chester, NY, is a rural town with a rich history in the dairy industry, famously known as the birthplace of Philadelphia-style cream cheese. Located minutes from Hudson Valley attractions and retail centers in Woodbury, Chester offers a mix of small-town single-family homes and larger farmhouses on multi-acre lots. The town is accessible via Route 17, making it a convenient location with relatively lower home prices compared to nearby towns like Monroe. Chester features diverse recreational options, including the family-friendly Castle Fun Center with carnival rides, mini golf, and an indoor roller-skating rink. Carpenter Community Park serves as the town's central green space, offering a playground, picnic pavilion, and sports courts, while Goosepond Mountain State Park provides 1,500 acres of trails for hiking and horseback riding. The Orange Heritage Trail, accessible from the historic Erie Depot, runs almost 20 miles through the county. Local attractions include Legoland in nearby Goshen and the Capelli Sports Complex. Chester Mall offers grocery shopping at ShopRite and movies at Flagship Premium Cinemas, while the Chester Agricultural Center provides farm-fresh produce. Dining options include the Rustic Wheelhouse Restaurant, known for its Italian cuisine. Homes in Chester range from older, smaller houses to larger contemporary and Craftsman-style homes on spacious lots. The Windridge Mews condo subdivision offers two to three-bedroom units. The Chester Union Free School District serves the town, with Chester Elementary and Chester Academy providing various after-school activities. Commuters can reach New York City or Newark in about an hour and a half via Interstate 87 or Coach USA buses.

Learn more about living in Chester

Frequently Asked Questions

What is the average home price in Chester, NY?
Homes for sale in Chester, NY have an average home price of $603,425.
How many homes have sold over the last 12 months in Chester, NY?
101 homes have sold in Chester, NY over the last 12 months.
What are the most popular zip codes in Chester, NY?
The most popular zip codes in Chester, NY include 10918, 10990, 10950, 10924 and 10921.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $541,950. If you put a 20% down payment of $108,400 and had a 30-year fixed mortgage with an interest rate of 6.01%, your estimated principal and interest payment would be $2,600 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $111K a year to afford the median home price in Chester. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Chester, NY?
Chester, NY has highly rated public and private schools. Some of the best schools in Chester based on Niche Grades are Greenwood Lake Elementary School, Warwick Valley High School and Warwick Valley Middle School. Browse all the schools in Chester, NY to learn more.

Home Trends in Chester, NY

On average, homes in Chester, NY sell after 58 days on the market compared to the national average of 54 days. The median sale price for homes in Chester, NY over the last 12 months is $520,000, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$520,000
Median Single Family Sale Price
$655,000
Median Townhouse Sale Price
$327,500
Median 2 Bedroom Sale Price
$310,000
Average Price Per Sq Ft
$268
Number of Homes for Sale
28
Last 12 months Home Sales
101
Months of Supply
3.30
Median List Price
$541,950
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
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