Chatham, NY Homes for Sale with Acreage

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  /36

  $749,000

  • 4 Beds
  • 4 Baths
  • 3,036 Sq Ft

  340 Lower Cady Rd, Old Chatham, NY 12136

  Set on 21 peaceful acres in one of the Hudson Valley's most coveted locations, 'Dawnbreak' is an Adirondack-inspired property offering a rare opportunity to create a beloved retreat. With over 3,200 square feet of living space, this four-bedroom, four-bathroom home combines rustic charm with generous proportions—ready for your vision to bring it to life.At the heart of the home is a dramatic

  

  Christine Hinz

  Coldwell Banker Village Green

  (518) 620-5873

  340 Lower Cady Rd, Old Chatham, NY 12136
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  /24

  $925,000

  • Land
  • 123 Acres
  • $7,508 per Acre

  0 Riders Mills Rd, Old Chatham, NY 12136

  In the heart of Chatham, this 123-acre pristine wooded paradise is a rare gem. With a serene pond and enchanting old stone walls that meander throughout the property it is a harmonious blend of natural beauty and timeless character. The property is a stunning canvas of mature trees, stone outcroppings, and picturesque landscape. Two road access points offers the choice of entry and development

  

  Christine Hinz

  Coldwell Banker Village Green

  (518) 990-2600

  0 Riders Mills Rd, Old Chatham, NY 12136
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  /45

  $299,900

  • 3 Beds
  • 1 Bath
  • 1,234 Sq Ft

  1 County Route 24, East Chatham, NY 12060

  Welcome home! This sweet cape is sure to charm. Enjoy a cozy, well maintained home on an acre of property! Great size kitchen, open to the dining area for ease when entertaining. Bedroom and full bath on the first floor. Two more bedrooms upstairs. Enjoy the convenience of a spacious mudroom to house your shoes and outdoor gear. Great location! Less than 3 hours to NYC, 30 minutes to Albany & 30

  Kevin Clancy Clancy Real Estate

  1 County Route 24, East Chatham, NY 12060
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  /104

  $875,000

  • 9 Beds
  • 6 Baths
  • 4,851 Sq Ft

  198 Richmond Rd, Valatie, NY 12184

  Welcome to your dream retreat! This incredible compound offers 9 bedrooms, 6 bathrooms, and nearly 10 acres of pure serenity. The stunning great room is the showstopper—surrounded by windows and boasting a massive open floor plan. Enjoy a chef's kitchen with island, bar stool seating and stainless steel appliances. Enjoy beautiful stone fireplace and wood stoves to keep you and guests nice and

  Kevin Clancy Clancy Real Estate

  198 Richmond Rd, Valatie, NY 12184
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  /35

  $189,900

  • Land
  • 23 Acres
  • $8,084 per Acre

  00WP Albany Turnpike Rd, Old Chatham, NY 12136

  Welcome to this versatile and picturesque 23.49-acre property located in the charming and historic town of Old Chatham, New York. Nestled in the heart of Columbia County, this buildable and subdividable parcel presents a rare opportunity for those looking to invest, build, or simply enjoy a private natural retreat. Whether you're envisioning a secluded country estate, a family compound, or a

  Mitch Serlin

  00WP Albany Turnpike Rd, Old Chatham, NY 12136
• 

  

  /86

  $2,500,000

  • 4 Beds
  • 4.5 Baths
  • 5,760 Sq Ft

  189 Sutherland Rd, Valatie, NY 12184

  Elegantly poised on 56.47 acres in Chatham, NY, paved driveway leads to a private oasis surrounded by lush, mature flower gardens, fruit and flowering trees, open fields, and a vast organic vegetable garden.This exceptional estate embodies the very essence of luxury living, thoughtfully designed for those who cherish nature. Expansive windows throughout the home frame stunning views at every

  Vera Cohen Vera Cohen Realty, LLC

  189 Sutherland Rd, Valatie, NY 12184
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  /154

  $2,500,000

  • 4 Beds
  • 4.5 Baths
  • 5,760 Sq Ft

  189 Sutherland Rd, Chatham, NY 12132

  Elegantly poised on 56.47-acres, this exceptional estate encapsulates the very essence of luxury living. A pristine pond, versatile outbuildings, organic garden & panoramic mountain views create a magnificent backdrop of natural splendor. The interior unfolds as a symphony of lavish indulgence, boasting the finest appliances, a sauna, 2 executive offices, a wet bar, outdoor kitchen. A sprawling

  Vera Cohen Vera Cohen Realty, LLC

  189 Sutherland Rd, Chatham, NY 12132
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  /78

  $1,500,000

  • 4 Beds
  • 4.5 Baths
  • 2,658 Sq Ft

  788 White Mills Rd, Valatie, NY 12184

  Step back in time without sacrificing modern amenities in this fully renovated 1850's farmhouse, nestled on an expansive 163+ acre estate set within serene woods. This exceptional property offers a rare combination of historic charm and contemporary convenience, featuring 4 bedrooms and 4.5 modern baths - each designed during a down to the studs renovation completed within the last 10 years. The

  Faith Adamec RE/MAX Capital

  788 White Mills Rd, Valatie, NY 12184
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  /97

  $1,700,000

  • 9 Beds
  • 9.5 Baths
  • 5,195 Sq Ft

  632 Albany Turnpike, Old Chatham, NY 12136

  Own a piece of Old Chatham history with the distinguished Samuel Wilbor House. Built circa 1770 and listed on the National Register of Historic Places, the estate includes a beautifully updated main house, three stylishly renovated apartments, and a converted barn. The main house features white pine woodwork, four fireplaces, an original Palladian window, and a large kitchen with floor-to-ceiling

  Anthony D'Argenzio Houlihan Lawrence

  632 Albany Turnpike, Old Chatham, NY 12136
• 

  

  /39

  $995,000

  • 4 Beds
  • 2.5 Baths
  • 4,590 Sq Ft

  23 Lovers Ln, Chatham, NY 12037

  At the heart of this timeless hamlet sits The Chatham House, offering a poetic blend of early American architecture and modern ease. Thoughtfully evolved over centuries, the home preserves its soul while embracing the comforts of today.Inside, light spills through elegant original windows and into the sweeping central hall and formal sitting rooms on either side of the house. A library

  Alexandra Demetrakis Upstate Down

  23 Lovers Ln, Chatham, NY 12037
• 

  

  /64

  $2,500,000

  • 4 Beds
  • 2.5 Baths
  • 4,243 Sq Ft

  5015 Crow Hill Rd, Chatham, NY 12037

  The Waterfall House is a modernist masterpiece, uniquely defined by its own cascading waterfall--a view you can enjoy from every room. Wade in the serene swimming hole below or wander through the exquisitely landscaped gardens that surround the home. Cozy up by the living room fire and admire the waterfall through a dramatic wall of glass.Designed to exist in perfect harmony with its natural

  Lisa Bouchard Hoe The Kinderhook Group, Inc.

  5015 Crow Hill Rd, Chatham, NY 12037
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  /8

  $989,000

  • 5 Beds
  • 4 Baths
  • 4,307 Sq Ft

  1896 County Route 9, Chatham, NY 12037

  Welcome to Bezalel Gables, where history meets elegance in this Queen Anne Victorian home, built in 1873 for a State Senator and nestled on an expansive 21 acres. This home boasts an impressive layout, featuring spacious living areas perfect for both intimate gatherings and grand entertaining. Venture outside, and you'll discover your own private oasis. The lush 21 acres are adorned with mature

  Tammy Molinski Coldwell Banker Advisor Realty

  1896 County Route 9, Chatham, NY 12037
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  /27

  $479,000

  • 5 Beds
  • 3 Baths
  • 2,740 Sq Ft

  4269 State Route 203, North Chatham, NY 12132

  Step back in time with this charming Queen Anne-style Victorian home, built in 1904. The home features many original details, moldings, and hardware. The first floor offers a kitchen with a butler's pantry, an oversized den with a built-in daybed in the window, a dining room, a living room with a fireplace, and a first-floor bedroom that could also serve as an office. Additionally, there are two

  Kari Van Buren Berkshire Hathaway HomeService

  4269 State Route 203, North Chatham, NY 12132
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  /36

  $535,000

  • 3 Beds
  • 2 Baths
  • 1,506 Sq Ft

  104 Eberle Rd, Valatie, NY 12184

  Are you dreaming of the perfect lakeside home? Look no further! This charming cottage sits on nearly an acre of land and has been carefully rebuilt and maintained by its current owner. Inside, you'll find three levels of cozy, functional living space. The main floor includes a lovely primary bedroom, a living room with a wood stove, dining area, a bright kitchen with vaulted ceilings and a

  Kari Van Buren Berkshire Hathaway HomeService

  104 Eberle Rd, Valatie, NY 12184
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  /36

  $525,000

  • 2 Beds
  • 1.5 Baths
  • 1,212 Sq Ft

  3041 State Route 66, Chatham, NY 12037

  On 12.5 acres in the hills of Chatham, this gem is equal parts peaceful escape & creative opportunity. The 2BR, 1 & half BA home is full of charm, w/ HW floors, a creek stone wood-burning FP, & 2 light-filled 3SR. A screened-in porch overlooks a stocked pond-perfect for morning coffee or quiet evenings. The land is a highlight in itself: a seasonal stream runs along the back edge, groomed trails

  Rebecca Sullivan Miranda Real Estate Group Inc

  3041 State Route 66, Chatham, NY 12037
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  /41

  $799,900

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft

  307 Pratt Hill Rd, Chatham, NY 12037

  Fall in Love with This Private Saltbox Retreat on 21+ AcresWelcome to your own secluded paradise—this charming Saltbox-style home is perfectly nestled on 21.4 private acres, offering complete privacy and beautiful views of the Catskill Mountains and Hudson Valley.Thoughtfully positioned so that no neighbors are in sight, this home is tucked away in nature where the only sounds

  Jason Walch Coldwell Banker Advisor Realty

  307 Pratt Hill Rd, Chatham, NY 12037
• 

  

  /96

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,088 Sq Ft

  4520 New York 66, Malden Bridge, NY 12115

  A Lovely 3 to 4 Bedroom, 2 Bath Home with a 2 Car Garage on 8.8 Acres! The 1st floor features 3 bedrooms, 1 bath, a kitchen, a dining area, a living room with a fireplace, and a sunroom. The living room has a beautiful stone fireplace with a Jotul Wood Stove insert. The kitchen has a breakfast bar. The dining area walks out to a charming sunroom. The basement features partially finished living

  Theodore Banta III RVW Select Properties

  4520 New York 66, Malden Bridge, NY 12115
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  /17

  $4,700,000

  • Land
  • 412 Acres
  • $11,408 per Acre

  69 County Rte 24, Chatham, NY 12037

  412 acre rare and enchanting paradise. A long gated driveway framed by mature maples & ancient stonewalls lead you over a bridge gently ascending through the woods and breaking open to rolling fields and stunning Catskill Mountain views. A perfect quiet spot to watch the firey evening sunsets while reflecting on the days end. Follow the path a bit further - winding through the Birch grove and

  Anne Harrison Country Life Real Estate, LLC

  69 County Rte 24, Chatham, NY 12037
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  /26

  $2,700,000

  • Land
  • 90 Acres
  • $30,000 per Acre

  190 Mallory Rd, Chatham, NY 12037

  90 acres with spectacular, full range, jaw- dropping Catskill & Berkshire & Taconic Mountain views in every direction! Totally private, quiet & secluded. Long gated driveway, beautiful pond, garage, well and electric in place. Just a few minutes from Chatham & TSP, 20 minutes to Hudson and 2 hours from NYC Relax, Enjoy & Get away from it all!.

  Anne Harrison Country Life Real Estate, LLC

  190 Mallory Rd, Chatham, NY 12037
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  /41

  $779,000

  • 5 Beds
  • 2.5 Baths
  • 2,860 Sq Ft

  1754 Harlemville Rd, Chatham, NY 12037

  5.79 acres in beautiful location w/privacy off secondary rd w/woods on all sides. Pond stocked w/lg mouth bass, landscaping, att one car garage, separate storage shed. Low maintenance Colonial style house w/brick & vinyl siding. Second floor en-suite primary on one end & three BRs + full bath on other end. Can be a five BR if needed. Revel in the tranquility of this 2,860 sq. ft. residence by the

  Frances Ingraham Heins Howard Hanna Capital Inc

  1754 Harlemville Rd, Chatham, NY 12037
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  /28

  $189,900

  • Land
  • 23 Acres
  • $8,084 per Acre

  00WP Albany Turnpike, Old Chatham, NY 12136

  Welcome to this versatile and picturesque 23.49-acre property located in the charming and historic town of Old Chatham, New York. Nestled in the heart of Columbia County, this buildable and subdividable parcel presents a rare opportunity for those looking to invest, build, or simply enjoy a private natural retreat. Whether you're envisioning a secluded country estate, a family compound, or a

  Mitchell Serlin WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

  00WP Albany Turnpike, Old Chatham, NY 12136
• 

  

  /18

  $695,000

  • 5 Beds
  • 4 Baths
  • 2,731 Sq Ft

  20 Depot Ln, Old Chatham, NY 12136

  Depot LaneNestled at the end of a quiet country lane, this charming historic home in the hamlet of Old Chatham offers the perfect blend of rural tranquility and warm community connections. Surrounded by sprawling gardens and quiet woods, the first floor of this peaceful retreat offers a spacious living room, complete with a wood-burning fireplace, an inviting eat-in kitchen perfect for family

  Andrea Gabel Gabel Real Estate

  20 Depot Ln, Old Chatham, NY 12136
• 

  

  /17

  $265,000

  • 3 Beds
  • 2 Baths
  • 1,594 Sq Ft

  1900 New York 203, Chatham, NY 12037

  Contractor Special: Office building ready for transformation to many possibilities. Common areas can accommodate open living/dining/kitchen concepts. Wideboard floors throughout. Attached shed serves as ample storage. A detached three bay garage is also on this 1.5 acre lot. Bring your vision for single-floor living to this blank slate just outside of Chatham Village.

  Jennifer Wall Anderson Agency

  1900 New York 203, Chatham, NY 12037
• 

  

  /16

  $695,000

  • Land
  • 34 Acres
  • $20,245 per Acre

  10 Thomas Rd, Valatie, NY 12184

  Magnificent opportunity to own a large barn in great condition on 34+ acres with a two-bedroom apartment and a massive office space. Views of the Catskill mountains with two ponds and 20 acres of pasture. Direct access to the property from Thomas Rd, Boice Rd. and Route 66. The barn has 15 stalls, concrete floors, and water spigots. The smaller of the two horse stall wings would make a great

  Patrick Lilly Patrick Lilly Team, LLC

  10 Thomas Rd, Valatie, NY 12184
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  /11

  $390,000

  • Land
  • 45 Acres
  • $8,667 per Acre

  0 County Route 28-A Unit 20251992, Chatham Center, NY 12184

  Commanding panoramic views in the heart of Chatham Center span the Helderbergs, Jiminy Peak and the Berkshires, and into Village of Chatham — all visible from the top of this dramatic hilltop parcel. With 5-acre zoning, the property has potential for subdivision, or the perfect opportunity to build a striking home on the hill, surrounded by sweeping, bucolic landscapes. A rare and spectacular

  Scott Paladino Chatham Properties

  0 County Route 28-A Unit 20251992, Chatham Center, NY 12184
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  /40

  $169,000

  • 3 Beds
  • 1 Bath
  • 2,048 Sq Ft

  2907 County Route 9, East Chatham, NY 12060

  Calling all Barn Lovers and Period Home Restorers! Come reimagine a legacy. Nestled on nearly 2 rolling acres of meadow and sky, This Old East Chatham Farmhouse invites you to revive a piece of Columbia County's earliest roots. Built in 1820 and rumored to be one of the area's oldest homes, this storied brick farmhouse still holds echoes of its past—wide-plank heart pine floors (milled from

  Brittany Craig Houlihan Lawrence Inc.

  2907 County Route 9, East Chatham, NY 12060
• 

  

  /31

  $679,000

  • 3 Beds
  • 3.5 Baths
  • 2,050 Sq Ft

  1582 State Route 203, Chatham, NY 12037

  A Chatham farm property with endless possibilities. Anchoring this 7-acre parcel is a 3BR, 3-1/2 BA home surrounded by fields, paddocks and woodlands. Set off from the home is an amazing barn complex and spring-fed pond. All less than a minute to downtown Chatham and equally close to the Taconic Pkwy. The property abuts the 65-acre Borden Pond conservation land - a hiker's paradise. The barn

  Jason Karadus Corcoran Country Living

  1582 State Route 203, Chatham, NY 12037
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  /49

  $3,995,000

  • 5 Beds
  • 3.5 Baths
  • 4,100 Sq Ft

  2705 County Route 9, East Chatham, NY 12060

  Welcome to The Anson Pratt House, a masterfully restored Federal Adams-style residence located in the historic hamlet of New Concord in East Chatham, NY. Built in 1793 atop a marble clad foundation, this architectural jewel is honored in the Library of Congress as part of the Historic American Buildings Survey. Featured in numerous architectural and design publications, The Anson Pratt House is

  Rachel Haley Houlihan Lawrence Inc.

  2705 County Route 9, East Chatham, NY 12060
• 

  

  /21

  $1,395,000

  • 4 Beds
  • 4 Baths
  • 4,000 Sq Ft

  524 County Route 17, North Chatham, NY 12132

  Introducing Hickory Hollow Farm to our roster of high value listings in Columbia County and located in the much sought after Kinderhook to Chatham corridor, this 1997 quality built full colonial Adam with a 3 car garage and sweeping front porch is available for our Spring market inventory. The 4000 square foot residence has 4 bedrooms, 4 bathrooms and is situated on 10 acres including its post

  Parker Meyer Four Seasons Sotheby's Int.

  524 County Route 17, North Chatham, NY 12132
• 

  

  /13

  $370,000

  • Land
  • 43 Acres
  • $8,585 per Acre

  L8 Lower Cady Rd, Chatham, NY 12136

  Enjoy this private country property located near a rural historic community. Located just a short drive to the NYS thruway and Mass Pike. Enjoy a short drive to the beautiful Berkshires and Jiminy Peak ski resort. Located minutes to the Taconic State Parkway for a scenic drive to NYC. There are two power poles on property located to the right of the meadow.

  Barry Shatney Bovair Real Estate

  L8 Lower Cady Rd, Chatham, NY 12136
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  /91

  $3,100,000

  • 7 Beds
  • 4 Baths
  • 5,188 Sq Ft

  311 County Route 13, Old Chatham, NY 12136

  Tucked into the heart of the Hudson Valley, where life slows and nature flourishes, lies Foxglove & Fern a breathtaking 101-acre sanctuary. As you follow the circular driveway, rolling meadows, ancient trees, and a shimmering private pond welcome you to a world of serenity.More than a home, this estate is a legacya place where generations gather, and every sunrise brings new adventures. The main

  Heather Etzel Four Seasons Sotheby's Int.

  311 County Route 13, Old Chatham, NY 12136
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  /31

  $719,000

  • 3 Beds
  • 2 Baths
  • 1,958 Sq Ft

  326 Pratt Hill Rd, Chatham, NY 12037

  Nestled in a serene, wooded setting, 326 Pratt Hill Road is a thoughtfully designed Cape-style home that blends rustic charm with modern comforts. Originally a quaint cabin, it has been carefully expanded over the years and now offers three bedrooms, two full bathrooms, and 8.1 private acres – perfect for a weekend escape or year-round living. The oversized living area features hardwood floors, a

  Callan Bergmann Compass Greater NY, LLC

  326 Pratt Hill Rd, Chatham, NY 12037
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  /34

  $1,250,000

  • 3 Beds
  • 3.5 Baths
  • 2,600 Sq Ft

  23 Raccoon Forks Rd, Old Chatham, NY 12136

  A post and beam barn on a dead end road in Old Chatham. Cathedral ceilings, walls wrapped in windows, bring in light and views from every angle. In the great room a brick fireplace with a chestnut mantle. Open floor plan makes it easy for entertaining. Shaker cabinets, soapstone counters, and hand crafted lighting. First floor primary bedroom ensuite with walk in closet. Two additional bedrooms

  Emma French Gabel Real Estate

  23 Raccoon Forks Rd, Old Chatham, NY 12136
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  /5

  $499,000

  • Land
  • 63 Acres
  • $7,866 per Acre

  325 Albany Turnpike, Nassau, NY 12115

  Potential Catskill ViewsThis 60+ acre parcel has a bit of everything and with a wee bit of clearing you'll be staring straight in to the entire Catskill Mountain range.

  Emma French Gabel Real Estate

  325 Albany Turnpike, Nassau, NY 12115
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  /32

  $529,000

  • 2 Beds
  • 1.5 Baths
  • 1,000 Sq Ft

  33 River Rd, Chatham, NY 12037

  At the end of a dead end road. Close to Chatham yet a world of privacy. 1874 gem with a post and beam barn to drool over. Historic cottage with original floors. Handcrafted features. Cherry kitchen with great storage and workspace. Dining area open to a deck overlooking the blooming bulbs, ornamental trees, flowering shrubs and picture perfect vegetable and cutting garden. Two bedrooms. Huge

  Tracy Tassinari Gabel Real Estate

  33 River Rd, Chatham, NY 12037
• 

  

  /19

  $260,000

  • Land
  • 27 Acres
  • $9,555 per Acre

  400 Pitts Rd, Chatham, NY 12136

  Hilltop land so close to Malden Bridge and Old Chatham? Here's an opportunity to own a parcel of land and nature in one of the most beautiful towns in the Hudson River Valley, Chatham NY. Private and secluded 27+ acre parcel nestled between the hamlet of Malden Bridge and Riders Mills Road and situated on a town-maintained, paved road. This wooded parcel has a combination of deciduous, coniferous

  Thomas Jan Van Alstyne Anderson Agency, Inc.

  400 Pitts Rd, Chatham, NY 12136
• 

  

  /23

  $699,000

  • Land
  • 66 Acres
  • $10,623 per Acre

  0 Cotter Rd, Chatham, NY 12136

  Nestled along a tranquil country road, discover 65 breathtaking acres of pristine land, offering a harmonious blend of open fields, enchanting woodlands, and serene stream. This idyllic parcel invites you to build your dream home amidst nature's splendor, providing ample space to roam, explore, and unwind.Imagine mornings spent wandering along picturesque stone walls and scenic walking paths, or

  Nikki Carchedi STONE HOUSE PROPERTIES, LLC

  0 Cotter Rd, Chatham, NY 12136
• 

  /2

  $199,900

  • Land
  • 14 Acres
  • $14,279 per Acre

  L34.111 County Route 9, New Lebanon, NY 12062

  Land is partially cleared for a building lot and it percs. South-West exposure, with potential views. Nice homes all around. So come build your dream home on your own piece of paradise. Conveniently located within 30 minutes of Albany, Berkshires, Chathams, TSP, Thruway.

  Sharon McArdle Berkshire Hathaway Home Services Blake

  L34.111 County Route 9, New Lebanon, NY 12062
• 

  

  /33

  $4,935,000 New Construction

  • 6 Beds
  • 4.5 Baths
  • 5,019 Sq Ft

  33 Ford Rd, Old Chatham, NY 12136

  CEDAR HILL - A HOUSE for all SEASONSBathed in sunlight, this graceful architectural masterwork is perfectly sited on ten private acres with awe-inspiring panoramic southern mountain views stretching endlessly, offering an ever-changing magical canvas of light and landscape. A home for all seasons, this newly re-built and expanded cedar house stands as if it rose from the

  Nancy Felcetto Brown Harris Stevens Hudson

  33 Ford Rd, Old Chatham, NY 12136
• 

  

  /6

  $40,000

  • Land
  • 2.22 Acres
  • $18,018 per Acre

  0 County Route 13, New Lebanon, NY 12060

  Hill-Top Views and an Open Field are Ready for Your Dream Home (manufactured or conventional). This recently subdivided lot of land is being sold for the first time. Featuring a large cleared field with road frontage on Rt 13 and Thompson Lane. The lot is less than 5 miles to Old Chatham, and less than 10 minutes drive to New Lebanon with restaurants, farmers market, and more.

  Susan Wendelboe Beach & Bartolo Realtors

  0 County Route 13, New Lebanon, NY 12060

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