Chatham, NY Homes

• 

  

  

  /30

  Est $472,246 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,564 Sq Ft

  49 E Shore Dr, Valatie, NY 12184

  49 E Shore Dr, Valatie, NY 12184
• 

  

  

  /27

  $379,000

  • 2 Beds
  • 1 Bath
  • 1,040 Sq Ft

  336 Ashley Hill Rd, Brainard, NY 12024

  Hidden Gem~This well-maintained, two- bedroom ranch-style home has so much to offer. It features a spacious living room with a wood burning fireplace and a large picture window, a light filled dining room and a well appointed kitchen.Outdoor living too with a charming front porch, a back deck perfect for dining and a hill top gazebo for quiet time. Over ten acres of wooded wonderland

  Lenore Packet Stone House Properties, LLC

  336 Ashley Hill Rd, Brainard, NY 12024
• 

  

  

  /91

  $1,300,000 Sold Aug 22, 2025

  • 3,940 Sq Ft
  • $330/SF
  • 46 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1800

  3 Pratt Rd, Nassau, NY 12123

  The Joseph A Pratt House in Malden Bridge, NY is the ideal Hudson Valley retreat. Built circa 1800, it is nestled on 67 acres of tranquil green lawns and wooded hills. In pristine condition, the property contains the stately, 3900 square foot main house, a 986 square foot guest house and a large barn (circa 1800) containing a two-car garage, a workshop and a four-season, finished studio with

  Richard Byrne Four Seasons Sotheby's Int.

  3 Pratt Rd, Nassau, NY 12123
• 

  

  

  /26

  Est $314,308 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,206 Sq Ft

  3875 State Route 203, Valatie, NY 12184

  3875 State Route 203, Valatie, NY 12184
• 

  

  

  /14

  $350,000

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

  3 Maiden Ln, Chatham, NY 12037

  Steps to town, this Chatham Village multi family features three generous one bedroom apartments. The well maintained building spins off a strong positive cash flow and and has undergone significant renovations such as new high efficient heating units in each apartment and a new boiler. The roof was replaced in 2014.

  Philip Feiner Country Life Real Estate, LLC

  3 Maiden Ln, Chatham, NY 12037
• 

  

  /31

  $679,000 Sold Aug 21, 2025

  • 2,050 Sq Ft
  • $331/SF
  • 95 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2006

  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
• 

  

  /38

  Est $592,611 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,452 Sq Ft

  99 Electric Park Rd, Valatie, NY 12184

  99 Electric Park Rd, Valatie, NY 12184
• 

  

  /30

  $445,000

  • 3 Beds
  • 1 Bath
  • 1,700 Sq Ft

  173 Hudson Ave, Chatham, NY 12037

  Unique opportunity to own an 1892 Colonial in Chatham. Handcrafted cherry kitchen made by local artisans. Extensive countertops with seating perfect for cooking for holidays and dinner parties. Large dining room and living room with high ceilings, original floors, and moldings. Large windows to bring the light in.Three bedrooms on the second floor. Laundry on the second floor. Finished third

  Tracy Tassinari Gabel Real Estate

  173 Hudson Ave, Chatham, NY 12037
• 

  

  /27

  $870,000 Sold Aug 08, 2025

  • 3,900 Sq Ft
  • $223/SF
  • 231 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2011

  170 Loomis Rd, Chatham, NY 12037

  Custom designed and built country contemporary in a very quiet setting. This light filled home offers almost 4000 sq ft of spacious, one level living. The finished living area is ADA compliant with open floor plan and wide passages. The Great room is central to the home and leads to additional gathering rooms, breakfast area, screened porch and stone terrace. There is an en suite master, with 3

  Linnea VanTassel Country Life Real Estate, LLC

  170 Loomis Rd, Chatham, NY 12037
• 

  

  /46

  Est $1,095,345 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 4,421 Sq Ft

  127 Crestview Dr, Valatie, NY 12184

  127 Crestview Dr, Valatie, NY 12184
• 

  

  /19

  $94,900

  • Land
  • 10.4 Acres
  • $9,125 per Acre

  0 Albany Turnpike, Old Chatham, NY 12136

  Here's your chance to secure a unique assignment opportunity on a beautiful wooded lot with endless potential. Tucked away in a quiet and private setting, this land is perfect for anyone seeking a peaceful retreat surrounded by nature. The property offers plenty of options - build your dream home in a serene location, create a hunting getaway, or hold it as an investment for the future. With

  John O’Neill-Knasick EXP REALTY

  0 Albany Turnpike, Old Chatham, NY 12136
• 

  

  /32

  $750,000 Sold Jul 31, 2025

  • 1,874 Sq Ft
  • $400/SF
  • 35 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1880

  14 Bushnell Ave, Chatham, NY 12037

  Step into The Bushnell House, a stately Victorian gem nestled on nearly an acre of lush, private land in the heart of Chatham Village. This four-bedroom, two-bath home effortlessly marries 19th-century charm with modern comfort, featuring original moldings, a grand fireplace mantel in the dining room, and a clawfoot bathtub that whispers of its timeless character. Sunlight pours through wide

  Alex Alvarez Compass Greater NY LLC

  14 Bushnell Ave, Chatham, NY 12037
• 

  /2

  Est $1,122,210 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,807 Sq Ft

  142 Riders Mills Rd, Old Chatham, NY 12136

  142 Riders Mills Rd, Old Chatham, NY 12136
• 

  

  /28

  $235,000

  • 2 Beds
  • 1.5 Baths
  • 900 Sq Ft

  3814 State Route 203, Valatie, NY 12184

  Perched on a hill, this cozy, walk-up hideaway has a western view of Kinderhook Lake, reminiscent of the Berkeley Hills or Cinque Terre. Enjoy the lake community and the year round lake views from the deck, enclosed porch or dining room. The home has a primary bedroom and one smaller bedroom, 1.5 BA, a central LR/DR, kitchen and an enclosed/heated front porch. Offers a nice degree of privacy

  Thomas Jan Van Alstyne Anderson Agency

  3814 State Route 203, Valatie, NY 12184
• 

  

  /33

  $550,000 Sold Jul 19, 2025

  • 2,173 Sq Ft
  • $253/SF
  • 11 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1865

  9 Fairview Ave, Chatham, NY 12037

  Tucked away at the peaceful end of a quiet street, this uniquely charming home is a rare find—offering a lifestyle of serenity, creativity, and community just steps from the heart of town. A wraparound veranda and screened-in gazebo welcome you into a world of natural beauty and artisanal detail, where wide board pine floors, reclaimed leaded glass windows, and a sunlit bay window create warmth

  Joseph Briggs William Pitt Sotheby's Int'l

  9 Fairview Ave, Chatham, NY 12037
• 

  

  /37

  Est $584,749 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 2,300 Sq Ft

  973 Albany Turnpike, Old Chatham, NY 12136

  973 Albany Turnpike, Old Chatham, NY 12136
• 

  

  /72

  $3,710,000

  • 3 Beds
  • 3.5 Baths
  • 4,104 Sq Ft

  249 Bashford Rd, Valatie, NY 12184

  ''Sweet Dreams Farm'' in the heart of Chatham Center referred to as ''Horse Country'' is an equestrian/gentlemen's farm adjacent to the Old Chatham Hunt Club trails. Possessing 2 separately deeded properties: The 1st, The Main House, is a 1800's historic salt box combo center hall colonial on 5.62 ac. Hosting: 3 beds, 3.5 baths, 5 fireplaces, custom gourmet kitchen, finely detailed moldings,

  Harold Reiser Julie & Co Realty LLC

  249 Bashford Rd, Valatie, NY 12184
• 

  

  /36

  $400,000 Sold Jul 18, 2025

  • 3,182 Sq Ft
  • $126/SF
  • 111 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1972

  52 Bowman Rd, Chatham, NY 12037

  Discover this exceptional custom home nestled on 5.97 acres, complete with a serene ponda perfect blend of privacy and convenience. Located in Chatham, this property offers endless potential, whether you're seeking a private retreat or an investment opportunity. Currently configured as a two-unit, it can easily be transformed into a charming single-family residence. Since its purchase in 2020,

  Allison Rada Stone House Properties, LLC

  52 Bowman Rd, Chatham, NY 12037
• 

  

  /68

  Est $1,434,019 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 5,655 Sq Ft

  540 County Route 17, Valatie, NY 12184

  540 County Route 17, Valatie, NY 12184
• 

  

  /44

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,930 Sq Ft

  2 Locust St, Chatham, NY 12037

  Village Charm Meets Modern Luxury: Historic Chatham Home for Sale An impeccably remodeled 3-bedroom, 2-bath home, originally built in 1863 is available now. Nestled on a semi-private lot in the heart of Chatham Village, this property offers an unparalleled blend of classic charm and contemporary living, all within walking distance of the area's vibrant amenities. Every system in the home has been

  Rachel Haley Houlihan Lawrence, Inc

  2 Locust St, Chatham, NY 12037
• 

  

  /16

  $430,000 Sold Jul 17, 2025

  • 1,576 Sq Ft
  • $273/SF
  • 53 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1963

  27 Upper Cady Rd, Old Chatham, NY 12136

  You know what they say about brick houses, "they're mighty, mighty"Super sweet location for this privately situated country home in horse country. Ez one story living with updated kitchen and baths. The gathering rooms are open to each other and the living room offers a brick fireplace. There is a full bath off the hall and a half bath off the primary bedroom.Bring the horses, goats or chickens

  Linnea VanTassel Country Life Real Estate, LLC

  27 Upper Cady Rd, Old Chatham, NY 12136
• 

  

  /33

  Est $334,162 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,492 Sq Ft

  50 Kinderhook St, Chatham, NY 12037

  50 Kinderhook St, Chatham, NY 12037
• 

  

  /40

  $545,000

  • 3 Beds
  • 1.5 Baths
  • 1,442 Sq Ft

  533 Shaker Museum Rd, Old Chatham, NY 12136

  In the heart of Chatham's historic hamlet of Malden Bridge, this 19th century three bedroom Colonial house, on almost an acre of land, is the ideal country home with modern updates on one of the most bucolic roads in Columbia County. The light filled living room opens directly into the dining room with lovely French doors that lead to a screened porch, ideal for relaxing or evening dining. The

  Sarah Lipsky William Pitt Sothebys Intn'l

  533 Shaker Museum Rd, Old Chatham, NY 12136
• 

  

  /19

  $422,500 Sold Jul 15, 2025

  • 2,400 Sq Ft
  • $176/SF
  • 32 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1850

  29 Thomas St, Chatham, NY 12037

  Charming 1850 two-family home in the heart of Chatham Village, renovated by a nationally known writer. Live on one side and rent the other, or use as a pure investment. Just a short trip to Main Street, with its classic Crandell Theatre, award-winning brewery, Bimi's Canteen, and all the small-town energy you want. Out front of the home is a deep front yard, wild berries, and a rocking chair

  Daniel Mahar Mahar Real Estate, LLC

  29 Thomas St, Chatham, NY 12037
• 

  

  /34

  Est $688,883 Not Listed For Sale

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

  65 Austerlitz St, Chatham, NY 12037

  65 Austerlitz St, Chatham, NY 12037
• 

  

  /13

  $342,000

  • 4 Beds
  • 4 Baths
  • 1,976 Sq Ft

  36 Spring St, Chatham, NY 12037

  This well-maintained multi-unit building offers a strong investment opportunity, with numerous updates, upgrades, and consistent maintenance over the years. The perfect opportunity to live and invest simultaneously, with three units that cater to both owner-occupants and investors.As of July 1st, 2025, Apt #3 with 2 Bedrooms will be available, making it perfect for those looking to owner

  Melinda Barbanti Davala Real Estate, LLC

  36 Spring St, Chatham, NY 12037
• 

  

  /65

  $899,000 Sold Jul 01, 2025

  • 4,602 Sq Ft
  • $195/SF
  • 246 Days On Market

  • 6 Beds
  • 6 Baths
  • Built 1999

  186 Richmond Rd, Valatie, NY 12184

  Welcome to 186 Richmond Rd, a remarkable family compound nestled in the heart of Hunt Country. The countryside's beauty is matched only by the elegance of the homes that dot the landscape. It's not uncommon for horses to share the road with passing autos, adding charm and tranquility to this rural setting. Surrounded by exquisite estates, this property offers an unparalleled opportunity to

  Michael Castellano Gilcrest Properties

  186 Richmond Rd, Valatie, NY 12184
• 

  

  /44

  Est $623,859 Not Listed For Sale

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

  944 Dugway Rd, Chatham, NY 12037

  944 Dugway Rd, Chatham, NY 12037
• 

  

  /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
• 

  

  /45

  $655,000 Sold Jun 30, 2025

  • 1,600 Sq Ft
  • $409/SF
  • 4 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2006

  53 Ten Broeck Rd, Chatham, NY 12037

  Only a few minutes outside of charming, vibrant Chatham, NY a magical stream side hideaway awaits. This clean, crisp, lofty contemporary home is all buttoned up and ready to move right in. Upon entering, the wonderful expanse of space created by cathedral ceilings and many windows and skylights will delight, while the generous ''mudroom'' entrance provides plenty of storage. The first

  Jennifer Capala William Pitt Sothebys Intn'l

  53 Ten Broeck Rd, Chatham, NY 12037
• 

  

  /16

  Est $567,272 Not Listed For Sale

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

  170 Macedonia Rd, Chatham, NY 12037

  170 Macedonia Rd, Chatham, NY 12037
• 

  

  /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
• 

  

  /45

  $655,000 Sold Jun 30, 2025

  • 1,600 Sq Ft
  • $409/SF
  • 16 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2006

  53 10 Broeck Rd, Chatham, NY 12037

  Only a few minutes outside of charming, vibrant Chatham, NY a magical stream side hideaway awaits. This clean, crisp, lofty contemporary home is all buttoned up and ready to move right in. Upon entering, the wonderful expanse of space created by cathedral ceilings and many windows and skylights will delight while the generous ''mudroom'' entrance provides plenty of storage. The first floor

  Jennifer Capala WILLIAM PITT SOTHEBY'S - LENOX

  53 10 Broeck Rd, Chatham, NY 12037
• 

  

  /32

  Est $1,419,168 Not Listed For Sale

  • 4 Beds
  • 5 Baths
  • 3,296 Sq Ft

  86 Stonewall Rd, Chatham, NY 12037

  86 Stonewall Rd, Chatham, NY 12037
• 

  

  /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
• 

  

  /34

  $495,000 Sold Jun 27, 2025

  • 1,624 Sq Ft
  • $305/SF
  • 47 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1920

  41 E Shore Dr, Valatie, NY 12184

  Spend the summer watching sunsets over Kinderhook Lake, dine under the gazebo & cook out on the ample deck area. Located near the deepest part of the lake, there is 50 feet of water frontage. Enter the home from the deck entrance, to an open concept kitchen recently renovated with granite counters & stainless steel appliances. The dining area has a wall of windows overlooking the lake & adjacent

  Kim Voltz Anderson Agency, Inc.

  41 E Shore Dr, Valatie, NY 12184
• 

  

  /42

  Est $2,200,469 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 4,350 Sq Ft

  284 Reed Rd, Chatham, NY 12037

  284 Reed Rd, Chatham, NY 12037
• 

  

  /97

  $1,650,000

  • 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
• 

  

  /35

  $335,000 Sold Jun 04, 2025

  • 1,400 Sq Ft
  • $239/SF
  • 27 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1920

  5 Washington Ave, Chatham, NY 12037

  Nice three story Village home on a side street. The street level has a garage, laundry area, guest space and bathroom or finish the rest of the first level for a studio or in law apartment. The second level has a kitchen, dining area, living room, two bedrooms, full bath and an enclosed sunny front porch to enjoy your morning coffee or your afternoon cocktail. The third level has a primary

  Karen Van Buren Berkshire Hathaway HomeService

  5 Washington Ave, Chatham, NY 12037
• 

  

  /72

  Est $2,017,796 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,637 Sq Ft

  114 Beale Rd, Chatham, NY 12037

  114 Beale Rd, Chatham, NY 12037

Showing Results 81 - 120, Page 3 of 18