Chester, NY Homes for Sale with Acreage

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  /50

  $799,900

  • 5 Beds
  • 4 Baths
  • 3,418 Sq Ft

  118 Murray Dr, Chester, NY 10918

  Nestled on 2.8 acres of lush, mature landscaping that borders the serene Goosepond Mountain State Park, this custom-designed contemporary ranch showcases a timeless blend of materials, with stone and brick construction lending both character and durability. Crafted by its original owners with meticulous attention to detail, the home offers a harmonious connection to its natural surroundings. A

  

  Brian Caplicki

  Keller Williams Hudson Valley

  (845) 409-8716

  118 Murray Dr, Chester, NY 10918
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  /50

  $859,900 Open Sun 1PM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 4,021 Sq Ft

  157 Creamery Pond Rd, Chester, NY 10918

  Welcome to Creamery Estates of Sugarloaf, where your dream home awaits just an hour’s drive from New York City. Nestled within walking distance of the charming downtown hamlet of Sugarloaf, this lovely residence is minutes away from schools, boutique shops, restaurants, grocery stores, the Sugar Loaf Performing Arts Center, wineries, breweries, apple orchards, the Appalachian trails, local

  Carla Terranova Keller Williams Realty

  157 Creamery Pond Rd, Chester, NY 10918
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  /42

  $719,000

  • 4 Beds
  • 4 Baths
  • 3,626 Sq Ft

  56 Sunset Ridge Rd, Monroe, NY 10950

  Welcome to 56 Sunset Ridge Road which sits by the private cozy cul-de-sac, a Magnificent backdrop on five luscious acres that envelope this tremendous center hall colonial. A beautiful driveway brings you home to your rocking chair front porch. Two story foyer gives way to the main level formal spaces. Living room, Dining Room, & a separate office leads you to an easy flowing, beautiful, recently

  Moses Schreiber MS Realty Group USA, Inc

  56 Sunset Ridge Rd, Monroe, NY 10950
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  /35

  $899,900

  • 4 Beds
  • 4 Baths
  • 4,854 Sq Ft

  4 Camelback Rd, Chester, NY 10918

  Stunning 4-Bedroom Home with Breathtaking Mountain Views!This is the one you've been waiting for! Nestled on a serene, tree-lined cul-de-sac, this luxurious 4-bedroom, 4-bath home offers the perfect blend of elegance, comfort, and spectacular mountain views.Step inside to a sun-drenched living room, where gleaming hardwood floors create an inviting ambiance. The spacious family room

  Veronica Goldzberg 2Win Realty LLC

  4 Camelback Rd, Chester, NY 10918
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  /38

  $747,900

  • 5 Beds
  • 3.5 Baths
  • 3,464 Sq Ft

  65 Oxford Springs Rd, Chester, NY 10918

  One-of-a-kind custom built Country Contemporary Home on 2.3 Acre on top of the hill. This Unique Open Floor plan welcomes bright warm sunlight in each of the 10 rooms. Top of the line hardwood floors and trim throughout the house, Large open kitchen with modern appliances and plenty of counter space including the granite island. 5 Bedrooms, 3.5 Bathrooms. Master bedroom with fireplace and walk

  Yoel Schwarz Glilos

  65 Oxford Springs Rd, Chester, NY 10918
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  /45

  $850,000 Open Sun 1:30PM - 3:30PM

  • 4 Beds
  • 2.5 Baths
  • 3,656 Sq Ft

  49 Stone Mountain Trail, Chester, NY 10918

  Nestled in a peaceful and private cul-de-sac, this stunning three-story contemporary colonial offers the perfect blend of elegance, space, and modern comfort. Set on an over 7 acre expansive lot, this home features a sprawling front and backyard, ideal for outdoor activities year-round—whether it’s summer fun by the pristine inground pool or winter ice sliding across the gentle slopes. A 2-car

  Leon Klein Keller Williams Hudson Valley

  49 Stone Mountain Trail, Chester, NY 10918
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  /7

  $899,900

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

  651 Lakes Rd, Monroe, NY 10950

  Build and Customize your dream home today on this compound in Monroe, Only one of its kind! The owner/builder has three plans for you tochoose from starting at 2600 sq feet - 5000 sq feet. This elegant, multi-family property consists of 3 residences nestled on over 3.5 statelylandscaped acres affording you peace and privacy. Surrounded by the original stone walls of this compound, this

  Frank Golio Howard Hanna Rand Realty

  651 Lakes Rd, Monroe, NY 10950
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  /39

  $650,000

  • 4 Beds
  • 2.5 Baths
  • 2,592 Sq Ft

  2 Laura Dr, Chester, NY 10918

  Fall in love with this stunning updated 4-bedroom Colonial located in Sugar Loaf Heights within the Warwick School District. You will feel like you apparated into the latest issue of Better Homes & Gardens the moment you enter. Agents - better schedule extra long showings as your clients will never want to leave! Step into the inviting living room featuring warm hardwood floors, soft recessed

  Virginia Corbett eXp Realty

  2 Laura Dr, Chester, NY 10918
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  /38

  $585,000

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

  12 Bianca Blvd, Chester, NY 10918

  Charming Colonial with Endless Potential – Priced to Sell!This stately Colonial is bursting with character and waiting for the right owner to bring it back to life! Nestled in a desirable neighborhood, this home offers classic architectural details, generous living spaces, and a layout perfect for modern living. While it needs some TLC, the potential here is undeniable—original hardwood

  Aoife Freeman Howard Hanna Rand Realty

  12 Bianca Blvd, Chester, NY 10918
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  /33

  $699,000

  • 4 Beds
  • 2.5 Baths
  • 2,452 Sq Ft

  138 Dug Rd, Chester, NY 10918

  Welcome home to this beautifully maintained Dutch Colonial situated on 2.6 serene acres within the desirable Monroe-Woodbury School District. This inviting home offers 4 spacious bedrooms, 2.5 bathrooms, and 2,452 square feet of well-appointed living space, thoughtfully designed for both comfort and functionality. Upon entering, you'll notice the natural light accentuating the gleaming hardwood

  Jake Garay Serhant LLC

  138 Dug Rd, Chester, NY 10918
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  /5

  $46,900

  • Land
  • 7 Acres
  • $6,634 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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  /49

  $1,900,000

  206 Greycourt Rd Unit 190, Chester, NY 10918

  **Endless Opportunities Await on This Rare 3.2-Acre Property!** For the first time in over 50 years, this prime piece of real estate is hitting the market! Nestled right off Route 17 with unbeatable exposure, this unique 3.2-acre property offers **unlimited potential** for investors, developers, or those looking for a special place to call home. Featuring **four structures**—a

  Susan McMullen eXp Realty

  206 Greycourt Rd Unit 190, Chester, NY 10918
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  /50

  $490,000

  • 3 Beds
  • 2.5 Baths
  • 1,716 Sq Ft

  16 Ayr Rd, Chester, NY 10918

  3/31/25 Multiple offers received. Please submit your highest and best by Wednesday, April 2, at 5:00. Include in your offer how any potential appraisal gap will be handled. Thank you for your interest in this home.This beautifully situated ranch style home offers amazing views, privacy, and convenience. The kitchen window displays a huge backyard with beautiful greenery in the spring and

  Luanne McGann Century 21 Full Service Realty

  16 Ayr Rd, Chester, NY 10918
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  /7

  $120,000

  • Land
  • 8 Acres
  • $16,000 per Acre

  31 Leone Ln, Chester, NY 10918

  7.5 acres located in Leone Industrial Park in Chester. This is raw land and buyer will have to perform their due diligence regarding permits, etc. with town. There are some wetlands on this property, so there will be limitations on what can be built. Due diligence is a must.

  Carole McCann Hudson Heritage Realty

  31 Leone Ln, Chester, NY 10918
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  /36

  $624,242

  • 4 Beds
  • 2.5 Baths
  • 2,236 Sq Ft

  20 Hubshop Rd, Chester, NY 10918

  CAPTIVATING CAPE COD! 1.5 Private Acres! 4 Bedrooms! 2 1/2 Bathrooms! 1 Car Garage! Gorgeous Updated Eat In Kitchen with Granite Counter Tops, Stainless Steel Appliances & Breakfast Nook! Master Bedroom Suite with Walk In Closet Located on the First Floor! Living Room with Double Sided Fireplace! Gleaming Hard Wood Floors! New Carpeting! Recessed Lighting! Laundry Room! Full Basement! Rocking

  Amanda Dnistrian ARC Realty 1 in Sales

  20 Hubshop Rd, Chester, NY 10918
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  /33

  $89,500

  • Land
  • 13 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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  /27

  $319,000

  • 4 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  156 Hardscrabble Rd, Chester, NY 10918

  Attention Skiers and/or Lovers of the Adirondacks -- Enjoy this spacious and warm 4 bedroom home. Natural light enhances the beauty of this home. Master bedroom on main floor, country eat-in kitchen and dining room, new washer and dryer, garage doors. Attic above the mudroom with stairs going up to spacious storage area. Running and play fenced-in area for pets. Screened-in porch and

  Carol Monroe Najer Realty

  156 Hardscrabble Rd, Chester, NY 10918
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  /2

  $57,500

  • Land
  • 1.73 Acres
  • $33,237 per Acre

  L37 Blue Bay Rd Unit Lakeview Pt. Lot 40, Chester, NY 12817

  This property has beach rights to two separate beaches. HOA Fee includes maintenance of beaches and road.Blue Bay Road is a Private Road.

  John Palermo John R. Palermo

  L37 Blue Bay Rd Unit Lakeview Pt. Lot 40, Chester, NY 12817
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  /20

  $169,500

  • Land
  • 23 Acres
  • $7,500 per Acre

  L2 Friends Lake Rd, Chester, NY 12817

  Seller financing now available with decent deposit and good credit. Previously approved 4-lot subdivision with beach rights to Murphy Beach on Friends Lake. 8.6 acre lot, 7.5 acre lot, 3.2 acre lot, and a 3 acre lot. Rough house and septic locations have been approved. (reference survey map) Possible views from the upper areas of the property with some select clearing. Make arrangements to walk

  Walter Swartz Gallo Realty ADK Inc

  L2 Friends Lake Rd, Chester, NY 12817
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  /24

  $1,900,000

  • 6 Beds
  • 4.5 Baths
  • 3,512 Sq Ft

  17 Bonnie Brook Rd, Monroe, NY 10950

  PICTURE-PERFECT MINI-ESTATE ON 20.6 ACRES - Nestled on a sprawling 20.6-acre parcel, this remarkable mini-estate offers the perfect blend of tranquility and opportunity. The property includes a newly renovated home, a charming older house primed for renovation, and a classic 1900s barn, all set against the backdrop of your own private lake and stunning grounds. Step inside the beautifully

  Michael Canter Keller Williams Hudson Valley

  17 Bonnie Brook Rd, Monroe, NY 10950
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  /10

  $289,900

  • Land
  • 6 Acres
  • $46,016 per Acre

  10 El Dorado Trail, Chester, NY 10918

  Amazing opportunity to own this 6.3 Acre Lot in Monroe School District, Drilled Well and Electric on site, drilled well in place, Level lot with panoramic views surrounded by exclusive homes. Come build your dream home only 60 Miles to NYC/Minutes to RT17/17M/I87

  Lisandra Rivera Keller Williams Realty

  10 El Dorado Trail, Chester, NY 10918
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  /14

  $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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  /16

  $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
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  /16

  $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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  /20

  $76,900

  • Land
  • 5 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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  /22

  $78,900

  • Land
  • 6 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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  /21

  $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

  $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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  /19

  $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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  /19

  $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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  /70

  $329,900

  • Land
  • 166 Acres
  • $1,988 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. The Potter Brook Timberlands property has abundant large, mature native tree

  John O'Donnell Timberland Realty

  L9 Atateka Rd, Chester, NY 12817
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  /20

  $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
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  /2

  $150,000

  • Land
  • 6 Acres
  • $23,511 per Acre

  L7 Atateka Dr, Chester, NY 12817

  Adirondack acres waiting for your next adventure to be built. Parcel comes with water access to put a boat in and out on the private Friends Lake in Chestertown, NY. Located on the East side of Friends Lake near all that the Adirondacks has to offer no matter what season it is. Just minutes to hiking, skiing at Gore Mountain, boating and enjoying the fresh mountain air.

  Jill Brady Hunt ERA

  L7 Atateka Dr, Chester, NY 12817
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  /11

  $1,379,000

  • 3 Beds
  • 1.5 Baths
  • 1,965 Sq Ft

  24 Durland Dr, Chester, NY 10918

  Discover a local opportunity - a spacious flat house situated on top of a large 23-acre property offering a serene and picturesque country living experience. This property presents an exciting chance for a lucrative investment, with the potential for future subdivision development. Conveniently located on Durland Road, just behind the main section of Route 17M in the Monroe Chester neighborhood,

  David Katina ESTMAX REALTY

  24 Durland Dr, Chester, NY 10918
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  /13

  $499,999

  • Land
  • 2.20 Acres
  • $227,272 per Acre

  6 Lookout Terrace, Chester, NY 10918

  Looking for just the right spot to build your dream home? Close to everything but also tucked away for peace and privacy. Spread out at the end of a cul de sac lies the land that can be the footprint for your new home. Make this your personal paradise or subdivide (7 lot potential) and sell as an investment. This 2.2 acre lot will be able to have municipal water and sewer. Conveniently located

  Gina Dudgeon Howard Hanna Rand Realty

  6 Lookout Terrace, Chester, NY 10918
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  /5

  $279,999

  • Land
  • 20 Acres
  • $13,875 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! ... Log and Go to walk lot... Site map in photos. This is one of only two remaining lots. Some wet-lands on the property. Drive way is not

  Karen Gauvin Our House Real Estate Group

  32 Mountainside Dr, Chester, NY 10918
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  /8

  $225,900

  • Land
  • 1.00 Acre
  • $225,900 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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  /5

  $55,000

  • Land
  • 1.30 Acres
  • $42,308 per Acre

  0 Route 94 Unit ONEH6315248, Blooming Grove, NY 10914

  This 1.3 acre lot lies just outside the Village of Washingtonville, making it conveniently located to all local amenities, as well as commuter options. No engineering has been done, and buyer will need to check with town officials for needed approvals.

  Carole McCann Hudson Heritage Realty

  0 Route 94 Unit ONEH6315248, Blooming Grove, NY 10914
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  /15

  $75,500

  • Land
  • 1.80 Acres
  • $41,944 per Acre

  L27 Carriage Knolls Rd, Chester, NY 12817

  Seller financing now available! This property has been cleared and excavated in preparation for a new home. Site-plans are complete, perc tests are complete, septic plans have been completed, an electric pedestal has been installed, building plans have been engineered and completed for a new house and garage. Buyer can build whatever house they would like on this parcel...does not need to be this

  Walter Swartz Gallo Realty ADK Inc

  L27 Carriage Knolls 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

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