Chester, NY Homes for Sale

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  /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
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  /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
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  /44

  $599,000

  • 4 Beds
  • 2 Baths
  • 2,056 Sq Ft

  6 Adams Ct, Monroe, NY 10950

  Stunning Split Ranch with Pool and Gorgeous Curb Appeal, Located in the Town of Chester within the Monroe-Woodbury School District Welcome to this beautifully maintained 4-bedroom, 2 full bath split ranch offering the perfect blend of comfort, style, and functionality. The upper level features a spacious and sun-filled eat-in kitchen, ideal for everyday living, with direct access to a big Trex

  Ida Payne Keller Williams Realty

  6 Adams Ct, Monroe, NY 10950
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  /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
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  /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
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  /19

  $83,500

  • Land
  • 2.84 Acres
  • $29,401 per Acre

  38 Granite Ridge Rd, Chester, NY 12817

  Private 2.84-acre partially cleared, buildable lot in a peaceful setting with proposed home and septic locations. Property features a gravel driveway with camper pad, Amish-built shed on gravel base, fire pit, and walking trail. Infrastructure in place includes 200-amp underground electric service plus 30-amp and 50-amp RV hookups. Conveniently located minutes from Cronin's Golf Resort, Friends

  Nicholas Khachadourian KW Platform

  38 Granite Ridge Rd, Chester, NY 12817
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  /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
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  /8

  $849,900

  $100K PRICE DROP

  • 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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  /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
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  /45

  $529,000

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

  63 Hubshop Rd, Chester, NY 10918

  Nestled on a quiet road off the beaten path, this serene 4-bedroom, 2.5-bathroom Colonial offers the perfect blend of secluded tranquility and commuter convenience. The main level features a traditional layout with a spacious living room, formal dining room, and a cozy recreation room perfect for relaxing. The functional eat-in kitchen serves as the heart of the home, while all four bedrooms are

  Charles Moore Keller Williams Realty

  63 Hubshop Rd, Chester, NY 10918
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  /32

  $344,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft

  1311 Whispering Hills Unit 96, Chester, NY 10918

  AOExperience Elevated Living: Your Private Hudson Valley Retreat at 1311 Whispering Hills Welcome to a home that offers more than just square footage—it offers a lifestyle change. Nestled in the scenic rolling hills of Orange County, 1311 Whispering Hills is a masterclass in modern suburban living. This meticulously maintained residence captures the essence of "home" from the moment you step

  Michael Jenney Keller Williams Realty

  1311 Whispering Hills Unit 96, Chester, NY 10918
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  /8

  $225,000

  $25K PRICE DROP

  • 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 Sugar

  Karen Gauvin Our House Real Estate Group

  34 Mountainside Dr, Chester, NY 10918
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  /37

  $405,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,392 Sq Ft

  58 Darin Rd, Warwick, NY 10990

  Welcome to this beautifully renovated townhome offering the perfect blend of modern upgrades, natural light, and low-maintenance living in one of the Hudson Valley’s most desirable communities. Step inside to discover gleaming hardwood floors, an open and inviting layout, and a sun-filled living space designed for both comfort and entertaining. The updated kitchen features stainless steel

  Melissa Forsyth Hudson Valley Home Connection

  58 Darin Rd, Warwick, NY 10990
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  /23

  $315,000

  • 2 Beds
  • 1 Bath
  • 736 Sq Ft

  301 Mountain Ave, Monroe, NY 10950

  Move right into this beautifully renovated 2 bedroom 1 bathroom home which has been fully updated for modern living. Upon entry you will find an open dining and kitchen area with new stainless steel appliances, quartz countertops and ample cooking space. The living room leads into the updated bathroom and two spacious bedrooms. Find new oak floors, new paint and tons of natural light throughout

  Samantha McCrory Exit Realty Connections

  301 Mountain Ave, Monroe, NY 10950

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