Chatham, NY Homes for Sale

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  /99

  $850,000

  • 6 Beds
  • 4 Baths

  2 High St, Chatham, NY 12037

  Step into these two beautifully restored historic homes where timeless character blends seamlessly with today's modern conveniences. Every detail has been thoughtfully updated, from new heating/Central air systems and high-end finishes to spacious, light-filled living areas designed for comfort and style. Enjoy two inviting porches - perfect for morning coffee, evening relaxation, or entertaining

  

  Joseph Cardinale

  HOWARD HANNA CAPITAL INC

  (518) 806-7476

  2 High St, Chatham, NY 12037
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  /35

  $695,000

  • 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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  /99

  $850,000

  • 6 Beds
  • 4 Baths

  30 Austerlitz St, Chatham, NY 12037

  Step into these two beautifully restored historic homes where timeless character blends seamlessly with today's modern conveniences. Every detail has been thoughtfully updated, from new heating/Central air systems and high-end finishes to spacious, light-filled living areas designed for comfort and style. Enjoy two inviting porches - perfect for morning coffee, evening relaxation, or entertaining

  

  Joseph Cardinale

  HOWARD HANNA CAPITAL INC

  (518) 299-5964

  30 Austerlitz St, Chatham, NY 12037
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  /104

  $799,000

  • 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
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  /46

  $1,250,000

  • 8 Beds
  • 3.5 Baths
  • 3,325 Sq Ft

  2659 County Route 9, East Chatham, NY 12060

  Situated on 19.5 serene acres in the historic hamlet of New Concord, Knollcroft is an exceptional and rare offering of historical significance. Listed on the National Register of Historic Places, Knollcroft is a showcase of late-Victorian craftsmanship and rural estate planning. Thoughtfully designed for both durability and grace, the home offers approximately 3,325 finished square feet, with 8

  Kelcey Otten Compass Greater NY, LLC d/b/a

  2659 County Route 9, East Chatham, NY 12060
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  /40

  $1,500,000

  • 5 Beds
  • 4 Baths
  • 4,512 Sq Ft

  226 County Route 17, Valatie, NY 12184

  Welcome to historic Surdeval Farm, a spacious 4,500 square-foot, five-bedroom, four-bath homestead on 24.5 acres located between the charming villages of Chatham, Kinderhook, and Valatie. Over the decades the original early 1800’s core home was expanded and rearranged. Now the formal entrance to the home is from the grand tree-lined circular driveway to the side door, to a foyer, which opens to a

  Peggy Lampman Peggy Lampman

  226 County Route 17, Valatie, NY 12184
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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
• 

  

  /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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  /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

  $1,200,000

  • 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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  /8

  $899,900

  • 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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  /14

  $375,000

  • 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
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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 -perfect for morning coffee or quiet evenings. The land is a highlight in itself: a seasonal stream runs along the back edge, groomed trails wind through the woods,

  Rebecca Sullivan Miranda Real Estate Group, Inc

  3041 State Route 66, Chatham, NY 12037
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  /50

  $565,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,681 Sq Ft

  4253 State Route 203, North Chatham, NY 12132

  Introducing Woodbine Cottage, a storybook Colonial built circa 1800 in the heart of North Chatham's historic district. Wide-plank floors, timber beams, and an original mantle recall its heritage, while a refreshed kitchen, renovated baths, and new appliances add modern ease. Outside, sweet dormer windows, columns, and a classic metal roof evoke an English country cottage. Two front porches invite

  Anthony D'Argenzio Houlihan Lawrence

  4253 State Route 203, North Chatham, NY 12132
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  /11

  $445,000

  • 3 Beds
  • 1 Bath
  • 1,700 Sq Ft

  173 Hudson Ave, Chatham, NY 12037

  1892 Colonial thoughtfully renovated with hand crafted cherry kitchen. High ceilings, and large windows. Wood floors. Original detail. Three good sized bedrooms. Full attic finished off with plumbing ready for another bath. Wonderful location with private yard. Two car garage. Level land and seasonal stream. Walk to the village.

  Tracy Tassinari Gabel Real Estate

  173 Hudson Ave, Chatham, NY 12037
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  /16

  $575,000

  • Land
  • 34 Acres
  • $16,749 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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  /37

  $549,000

  • 3 Beds
  • 3 Baths
  • 1,953 Sq Ft

  28 Green Brook Dr, Brainard, NY 12024

  Timeless country elegance best describes this charming custom-built Cape, set on 2.6 acres along the Green Brook in the Town of Chatham, just outside the hamlet of Malden Bridge. Built with craftsmanship and rich character, the home blends tradition with modern comfort, featuring solid wood doors, cherry hardwood floors, custom kitchen and lighting, tiled baths, and a welcoming living room with a

  Joseph Briggs William Pitt Sothebys Int Rlty

  28 Green Brook Dr, Brainard, NY 12024
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  /37

  $250,000

  • 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
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  /119

  $4,860,000

  • 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 3 separately deeded properties: The Main House, is a 1800's historic salt box combo center hall colonial. Hosting: 3 beds, 3.5 baths, 5 fireplaces, custom gourmet kitchen, finely detailed moldings, original wide plank

  Harold Reiser Julie & Co Realty, LLC

  249 Bashford Rd, Valatie, NY 12184
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  /36

  $429,000

  • 3 Beds
  • 2 Baths
  • 1,806 Sq Ft

  11 Washington Ave, Chatham, NY 12037

  This charming Chatham home has it all, whether you're looking for a weekend retreat or a convenient year-round residence. Pride of ownership featuring three bedrooms, two full bathrooms with a full basement for extra storage and workspace. You'll love the screened in front porch, perfect for relaxing while enjoying your morning coffee. This bright and sunny home has an updated kitchen,

  Ann Marie Silvani Howard Hanna Rand Realty

  11 Washington Ave, 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
• 

  

  /17

  $469,000

  • 3 Beds
  • 2 Baths
  • 1,308 Sq Ft

  16 Middlebrook Ln, Chatham, NY 12037

  Set privately high on a hill in Chatham Center. Long driveway to a perfect country retreat with gorgeous stonewalls. Huge random bluestone patio with stone fireplace and built in BBQ perfect for outside entertaining. Gorgeous in-ground pool with perfect stonewalls leading to a stone courtyard area perfect for lounge chairs and summer picnics. Meticulously maintained home with open kitchen to

  Tracy Tassinari Gabel Real Estate

  16 Middlebrook Ln, Chatham, NY 12037
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  /11

  $499,000

  • 3 Beds
  • 3 Baths
  • 2,264 Sq Ft

  7 Railroad Ave, Chatham, NY 12037

  MIXED USE POTENTIAL IN CHATHAM'S HISTORIC DISTRICT This striking Greek Revival, circa 1850 sits proudly in the historic district of Chatham Village. It was lovingly renovated in 2004, with special attention to preserving the building's period details and historic charm.A boxwood-lined walkway leads to the welcoming interior. The front door opens to a side hall with a graceful

  Lenore Packet Stone House Properties, LLC

  7 Railroad Ave, Chatham, NY 12037
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  /45

  $449,000 Open Sun 11AM - 1PM

  • 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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  /22

  $480,000

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

  2 Locust St, Chatham, NY 12037

  Village Charm Meets Modern Luxury: Historic Chatham Home for SaleAn 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

  Rachel Haley Houlihan Lawrence Inc.

  2 Locust St, Chatham, NY 12037
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  /36

  $529,000

  • 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, 1904 sq.ft. of 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

  Kari Van Buren Berkshire Hathaway HomeService

  104 Eberle Rd, Valatie, NY 12184
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  /40

  $595,000

  • 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
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  /96

  $374,900

  • 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

  Ted Banta RVW Select Properties

  4520 New York 66, Malden Bridge, NY 12115
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  /14

  $375,000

  • 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
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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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  /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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  /28

  $133,900

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft

  296 New York 295 Unit Lot 19, Chatham, NY 12037

  Charming 2-Bed, 2-Bath Single-Wide Mobile Home in Sought-After Chatham - No Age Restrictions!Don't miss this rare opportunity to own a beautifully maintained 2-bedroom, 2-full-bath single-wide mobile home in the highly desirable area of Chatham—and best of all, it's located in a non-55+ community!This home offers a bright, open-concept layout with a spacious living area, a

  Margaret Guerra Gilcrest Properties

  296 New York 295 Unit Lot 19, 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
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  /28

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,630 Sq Ft

  50 Payn Ave, Chatham, NY 12037

  A True Chatham Charmer: DIVE INTO SUMMER! Welcome to Dogwood Cottage, a village retreat with a backyard to swoon over. Built in 1945 with the strength and character of a Victory Cottage, this storybook home has been lovingly cared for with so much potential to update exactly as you would likeInside, gorgeous original hardwood floors and a custom-designed kitchen anchors the heart of the home,

  Brittany Craig Houlihan Lawrence Inc.

  50 Payn Ave, 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
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  /50

  $598,000

  • 4 Beds
  • 4 Baths
  • 3,050 Sq Ft

  635 Albany Turnpike, Old Chatham, NY 12136

  In the heart of Old Chatham, is this rare opportunity to purchase a historic, well maintained, 3 unit property with views of breathtaking, cascading waterfalls. The Old Chatham Post Office currently occupies one unit (3 years remain on the lease) and, there are 2 updated, currently vacant apartments to rent, live in or use as office space. The two level, 2 bedroom apartment and a 1 (could be 2)

  Peter Newman Beach & Bartolo Realtors

  635 Albany Turnpike, Old Chatham, NY 12136
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  /36

  $599,000

  • 4 Beds
  • 2 Baths
  • 2,402 Sq Ft

  662 Albany Turnpike, Old Chatham, NY 12136

  Step back in time with this enchanting 1820s village Colonial, a true jewel box filled with original details and timeless charm. This home exudes warmth and tranquility, featuring high ceilings, wide plank floors, and both front and back staircases leading to three generously sized bedrooms. A hidden ''secret'' nook offers the perfect space for hide-and-seek, quiet reflection, or a cozy

  Jonathan Hallam The Kinderhook Group, Inc.

  662 Albany Turnpike, Old Chatham, NY 12136

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