Chester, NY Homes for Sale

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  /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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  /33

  $295,000

  • 2 Beds
  • 1 Bath
  • 1,084 Sq Ft

  1401 Whispering Hills, Chester, NY 10918

  Discover the perfect blend of comfort, convenience, and community in this 2-bedroom, 1-bath end-unit townhouse. Situated in a quiet corner of the neighborhood, this home offers extra privacy and natural light, along with the added benefit of an attached 1-car garage for secure parking and storage. Inside, you'll find a thoughtfully designed layout that maximizes space and livability - ideal for

  Debbie Goldstein Howard Hanna Rand Realty

  1401 Whispering Hills, 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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  /38

  $500,000

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

  16 Mari Rd, Chester, NY 10918

  Set back on a quiet street, just steps from downtown Sugar Loaf is this large home on almost an acre. Walk into the open living room and dining room, open to the kitchen with stainless steel appliances. The primary bedroom has access to the back deck, perfect for sipping your morning coffee overlooking the large peaceful backyard. Two additional bedrooms and a full bath complete the main floor.

  Kimberly Corkum Keller Williams Realty

  16 Mari Rd, 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.).

  Karen Gauvin Our House Real Estate Group

  34 Mountainside Dr, Chester, NY 10918
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  /28

  $319,000

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft

  3917 Whispering Hills, Chester, NY 10918

  Welcome to Whispering Hills! This beautifully maintained home features a galley kitchen with stainless steel appliances and a convenient in-unit washer and dryer. The first level offers a stylish half bath and well-kept flooring throughout the kitchen, dining room, and living room. Enjoy cozy evenings by the fireplace, and extend your living space outdoors on the private patio. Upstairs, you’ll

  Jie Liu Keller Williams Hudson Valley

  3917 Whispering Hills, Chester, NY 10918
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  /40

  $849,000

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

  4 Debbie Ct, Chester, NY 10918

  DISCOVER THE EPITOME OF LUXURY LIVING! With 5400 sq ft of breathtaking property, where every corner is designed for both elegance and practicality!! With expansive living areas, high-end finishes, and modern amenities, this home is perfect for entertaining or enjoying quiet moments. Embrace a lifestyle of comfort and sophistication in a space that truly feels like a retreat all year

  Joseph Rosenfeld Flag Realty Group

  4 Debbie Ct, Chester, NY 10918
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  /14

  $144,900

  • Land
  • 0.47 Acre
  • $308,298 per Acre

  L31 Clarkson Rd, Chester, NY 12817

  Build Your Adirondack Getaway on Loon Lake!Enjoy beach rights on beautiful Loon Lake with this just-under-half-acre lot, the perfect spot to create your own year-round retreat or seasonal escape. Whether you dream of summer days by the water, paddling and swimming, or cozy winter weekends in the mountains, this property offers an ideal starting point for your Adirondack lifestyle.

  Brooke Clark Four Seasons Sotheby's International Realty

  L31 Clarkson Rd, Chester, NY 12817
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  /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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  /5

  $35,000

  • Land
  • 7.07 Acres
  • $4,950 per Acre

  L30 Lane Rd, Chester, NY 12853

  You won't want to miss out on this opportunity! A little over 7 acres (2 parcels) in the heart of the Adirondacks. Close proximity to all the local lakes (Schroon Lake, Loon Lake, Brant Lake) & 10 minutes from Gore Mountain.

  Julia Pucciarelli Gallo Realty ADK Inc

  L30 Lane Rd, Chester, NY 12853
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  /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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  /13

  $37,500

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

  13 Carriage Rd, Chester, NY

  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 steeper 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

  13 Carriage Rd, Chester, NY
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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
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  /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
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  /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
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  /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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  /23

  $68,900

  • 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
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  /9

  $49,500

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

  20 Carriage Rd, Chester, NY

  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 steeper 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

  20 Carriage Rd, Chester, NY
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  /31

  $65,000

  • Land
  • 5.42 Acres
  • $11,993 per Acre

  L7 Macglashan Ln, Chester, NY 12817

  Very nice 5.42 acres of property with plenty of secluded building options. Gently sloping topography with mixed hardwood and conifers throughout. An abundance of wildlife signs from end to end of this parcel. This property is zoned ''Rural Use'' and would be used ideally for a home or cabin (one-primary single family residence) with garage or other auxiliary building. Seller financing possible

  Walter Swartz Gallo Realty ADK Inc

  L7 Macglashan Ln, Chester, NY 12817
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  /8

  $849,900

  • 4 Beds
  • 2.5 Baths
  • 2,603 Sq Ft

  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 will truly be a lovely property with land, privacy and wonderful mountain views! This modern farm house cape features over 2,600 sq ft. and is completely CUSTOM and DELIVERED TURN-KEY ... build this home, or bring your own dream plans/ideas! This ONE LEVEL living

  Karen Gauvin Our House Real Estate Group

  32 Mountainside Dr, Chester, NY 10918
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  /4

  $350,000

  • Land
  • 5.1 Acres
  • $68,627 per Acre

  0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918

  Very private lot in mature subdivision of large homes. Home site has been cleared and driveway base laid down. With a small amount of brush-clearing in the tree line there can be views of the valley and watershed lands.

  Theresa Powers Keller Williams Realty

  0 Odyssey Dr Unit KEY858370, Chester Town, NY 10918
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  /18

  $310,000

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft

  3120 Whispering Hills, Chester, NY 10918

  Welcome to this charming 2-bedroom condo in the desirable Whispering Hills community! This unit faces green space and trees for added privacy as well as comfortable living spaces. The home features a cozy living room with a fireplace, a dining area, and a full kitchen ready for everyday meals or weekend entertaining. Enjoy the convenience of having your own in-unit washer and dryer, plus a

  Bente Brown John J Lease REALTORS Inc

  3120 Whispering Hills, Chester, NY 10918
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  /37

  $569,999

  • 4 Beds
  • 2.5 Baths
  • 2,040 Sq Ft

  78 Pickerel Rd, Monroe, NY 10950

  Welcome to this charming Colonial set in the desirable Trout Brook ll subdivision of Monroe. This lovely home offers the perfect balance of privacy and convenience—just minutes to local shops and the village, and a short 10–15 minute drive to all major highways. Plus, you're only an hour from NYC, making it ideal for commuters or weekend getaways. Outdoor enthusiasts will love the close proximity

  Lauren Kelly Howard Hanna Rand Realty

  78 Pickerel Rd, Monroe, NY 10950
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  /8

  $225,000

  • Land
  • 1 Acre
  • $225,000 per Acre

  34 Mountainside Dr, Chester, NY 10918

  Lovely 1-Acre lot w/MOUNTAIN VIEWS & NATURAL GAS in a beautiful newly built SUB-DIVISION. Build out this nearly completely built lovely sub-division, curb-cuts, paved road sloping lot perfect for a WALK-OUT BASEMENT and DECKS FOR BEAUTIFUL VIEWS ... FULLY APPROVED LOT, ESTABLISHED NEIGHBORHOOD, VERY COMMUTABLE location! Close to the vibrant shopping, restaurants, nightlife, shows/events at

  Karen Gauvin Our House Real Estate Group

  34 Mountainside Dr, Chester, NY 10918
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  /24

  $74,900

  • Land
  • 4.31 Acres
  • $17,378 per Acre

  102 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

  102 Carriage Knoll Rd, Chester, NY 12817
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  /17

  $309,900

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

  1503 Whispering Hills, Chester, NY 10918

  Big price reduction! Come see it before it's gone. Nice end unit 3 bedroom 2.5 bath condo with 2 car garage in whispering hills. Primary bedroom with private full bath and 2 nice size extra bedrooms plus a hall bath on the 2nd floor. Warm up on those cold nights with the fireplace in the living room. Enjoy a quiet moment on your private patio sipping your coffee. Great location with playground

  Darlene Provino Century 21 E & M Williams Rlty

  1503 Whispering Hills, Chester, NY 10918
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  /50

  $1,775,000

  • 4 Beds
  • 2.5 Baths
  • 3,348 Sq Ft

  20 Goshen Rd, Chester, NY 10918

  Discover a rare opportunity to own a one-of-a-kind estate set on 53 sprawling acres in the heart of Chester, NY—perfectly suited for luxury living, farming, or future development with subdivision potential. This impressive property features a 3-car garage with 10-foot doors, outdoor wood-burning furnace, and two 250-gallon oil tanks for efficient heating.Nature lovers and hobby farmers

  Ramanjit Dhanoa eXp Realty

  20 Goshen Rd, Chester, NY 10918
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  /71

  $299,900

  • Land
  • 165.92 Acres
  • $1,807 per Acre

  L9 Atateka Rd, Chester, NY 12817

  This is a fantastic opportunity to own your own patch of beautiful Adirondack woods, nearly 166 acres, complete with a perennial stream, beaver pond, mature timber, and plenty of wild game. Use this property as your own recreational playground or build your dream home or camp in this peaceful, wooded retreat. Property is access by a right of way from Atateka Rd. Proceed ~400 feet to property

  John O'Donnell Timberland Realty

  L9 Atateka Rd, Chester, NY 12817
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  /48

  $920,000

  • 4 Beds
  • 2.5 Baths
  • 2,969 Sq Ft

  23 W Meadow Way, Warwick, NY 10990

  Views abound from this stunning colonial in the Warwick Ridge Sub-Division. Don't miss out on this custom built colonial.includes Chefs kitchen, quartz counters, extensive trim package, custom tile, hardwood the worksAccepted Offer 12/1

  Robert Valentine BHG Real Estate Green Team

  23 W Meadow Way, Warwick, NY 10990
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  /20

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 1,384 Sq Ft

  99 Evan Rd, Warwick, NY 10990

  Welcome in to this beautifully maintained 3-bed, 2.5-bath townhouse offering the perfect blend of comfort, space, and convenience. The main level welcomes you with gleaming hardwood floors and a formal dining room—ideal for gatherings and everyday meals alike. The bright, spacious living areas flow effortlessly, creating a warm and inviting atmosphere.Upstairs, the primary bedroom features

  Brittany Barry HV Premier Properties Realty

  99 Evan Rd, Warwick, NY 10990
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  /24

  $530,000

  • 4 Beds
  • 2 Baths
  • 1,322 Sq Ft

  5 Berkley Terrace, Monroe, NY 10950

  Lake Rights! Low Taxes! Welcome home to this lovely cape, beautifully situated on a double lot allowing for plenty of yard space for peace and privacy. This home features 4 bedrooms and 2 full bathrooms with a large eat-in kitchen, wood floors and a spacious unfinished, walk-out basement. Walk-out from the kitchen onto a lovely deck for grilling, dining and relaxing as you take in the tree-top

  Layla Rose Boyles Century 21 Realty Center

  5 Berkley Terrace, Monroe, NY 10950
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  /27

  $395,000

  • 2 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  36 Marian Ct, Warwick, NY 10990

  Turnkey Townhome with Scenic Views – No HOA – Warwick School District. Welcome to your newly renovated 2-bedroom, 1.5-bath townhome in the heart of Warwick, just 60 minutes from NYC. This beautifully updated home is perfect for first-time buyers or anyone seeking a stylish, low-maintenance lifestyle in a quiet, commuter-friendly setting—without the restrictions of an HOA. Set against a backdrop

  Courtney Tablante Keller Williams Realty

  36 Marian Ct, Warwick, NY 10990

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