Chester, NY Homes for Sale with Acreage

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  /32

  $509,999

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  391 Bull Mill Rd, Chester, NY 10918

  Motivated Seller!! Welcome home to this storybook setting, where a majestic weeping cherry blossom greets you with it's graceful cascade of blossoms each spring. This beautifully preserved historical farmhouse set on 1.7 acres along a scenic country road just down the lane from a local farm where the soft "mooing" adds to the peaceful rural charm. Sitting pretty on a corner lot with a circular

  

  Alexandra Zinko

  Century 21 Realty Center

  (845) 412-9860

  391 Bull Mill Rd, Chester, NY 10918
• Explore Chester

• 

  

  

  /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

  

  Luanne McGann

  Century 21 Full Service Realty

  (845) 447-0221

  7 Park Place, Chester, NY 10918
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  /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
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  /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
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  /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
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  /93

  $1,750,000

  • 6 Beds
  • 7.5 Baths
  • 7,034 Sq Ft

  69 Cedar Pond Ln, Chester, NY 10918

  Set on 10 private acres with sweeping mountain views from nearly every room, 69 Cedar Pond is a five-bedroom, eight-bath estate that exemplifies expansive design and contemporary style. The striking A-frame architecture, double-height windows, and soaring ceilings create dramatic, light-filled interiors where every angle frames the surrounding landscape and sunsets. A three-story entry sets the

  Emily Iason Four Seasons Sotheby's Int.

  69 Cedar Pond Ln, Chester, NY 10918
• 

  

  /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
• 

  

  /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
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  /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
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  /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
• 

  

  /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
• 

  

  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /45

  $1,395,000 Open Sun 12PM - 2PM

  • 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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  /3

  $699,000

  • Land
  • 2 Acres
  • $349,500 per Acre

  50 Elkay Dr, Chester, NY 10918

  Last remaining parcel available on Elkay Drive in the Chester Industrial Park.This 2-acre industrial lot was previously fully approved for a two-story building with loading docks. While approvals expired approximately 10 years ago, the site’s industrial potential remains strong. Both adjacent parcels are currently under development, with 30,000+ SF warehouse facilities being constructed,

  Leib Glanz Point Realty USA

  50 Elkay Dr, Chester, NY 10918
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  /34

  $999,000

  • 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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  /33

  $89,500

  • Land
  • 12.79 Acres
  • $6,998 per Acre

  3-4 Adirondack Heights Rd, Chester, NY 12817

  Seller financing now available. 12.79 acres of mixed forest and wetlands. Perc tests and engineered plot plans have been completed. APA approved building sites with well & septic locations identified. (2-lots can each be built upon or just have one large lot) Power at the road pedestal box. Tons of hemlock, spruce, and pine trees throughout. Close to Chestertown, 20-minutes to Gore Mountain or

  Walter Swartz Gallo Realty ADK Inc

  3-4 Adirondack Heights Rd, Chester, NY 12817
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  /30

  $725,000 Open House 2/21

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

  487 Black Meadow Rd, Chester, NY 10918

  Experience the perfect harmony of 19th-century character and expansive modern living in this grand 1872 Colonial farmhouse. Situated on a lush, level one-acre lot within the prestigious Warwick Valley School District, this 4,204-square-foot residence offers a rare combination of scale, history, and potential. The journey begins in a welcoming foyer that opens into a formal dining room and a

  Dominic Santagato Joseph Baratta Company Realty

  487 Black Meadow Rd, Chester, NY 10918
• 

  

  /19

  $74,900

  • 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
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  /28

  $799,999 Open Sun 1PM - 3:30PM

  • 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
• 

  

  /22

  $68,900

  • 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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  /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
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  /23

  $76,900

  • 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
• 

  

  /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
• 

  

  /25

  $78,900

  • 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
• 

  

  /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
• 

  

  /5

  $74,900

  • Land
  • 1.79 Acres
  • $41,844 per Acre

  L4-5 Marina Rd, Chester, NY 12817

  This is two lots combined for better access and development and has beach rights to two beaches shown on map. HOA Owner's association fee includes beach maintenance. HOA board is working toward the possibility of installing a boat docksystem for the future. Presently there is space for non motorized craft on the beaches. Broker (John R. Palermo) is handling this property for his family's LLC

  John Palermo John R. Palermo

  L4-5 Marina Rd, Chester, NY 12817

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