Chatham, NY Homes

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  /31

  $1,200,000

  • 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 and office

  Alexandra Demetrakis Upstate Down

  23 Lovers Ln, Chatham, NY 12037
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  /5

  $1,200 per month

  • 0.5 Baths
  • 800 Sq Ft
  • House for Rent

  1 Main St, Chatham, NY 12037

  Full-floor office unit for rent on the second floor of Chatham's iconic Clock Tower building. This bright, beautiful space overlooks the village's charming Main St. The main loft-like space is large and lined with windows. There's also a smaller office with door and transom windows, plus a half bathroom. Approx. 800 sq feet total. Historical details abound in the 1875 building, steps from Main

  Jeffries Blackerby Stone House Properties, LLC

  1 Main St, Chatham, NY 12037
• 

  

  

  /22

  $120,000 Sold Apr 30, 2025

  • 1,216 Sq Ft
  • $99/SF
  • 43 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2013

  1903 New York 203 Unit 14, Chatham, NY 12037

  Come and visit this absolutely beautiful Edgewood Acres Champion Home in Ghent that was built new in 2013 and has been in the same family since it was purchased. It features 3 large bedrooms & 2 full baths. This home is 16x76 and has been meticulously maintained since it was purchased. Itbacks up to a private wooded area, with shed included. Lot rent is $547 which includes garbage, taxes water

  Stephen Cole Gilcrest Properties

  1903 New York 203 Unit 14, Chatham, NY 12037
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  /2

  Not Listed For Sale

  • 7 Beds
  • 6 Baths
  • 5,448 Sq Ft

  206 Thomas St, Chatham, NY 12037

  206 Thomas St, Chatham, NY 12037
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  /46

  $895,000

  • 3 Beds
  • 3.5 Baths
  • 3,500 Sq Ft

  874 Co Rte 32, Chatham, NY 12132

  Two newer homes for the price of ONE, situated on almost 30 acres! The stunning chalet built in 2018, consists of 2bedrooms + office/den in basement, offering a spacious and inviting open floor plan perfect for entertaining(indoor & outdoor!), tons of natural sunlight & so much more. Adding to the allure is a newly constructed detached garage, completed in 2023, which includes a 1BED/1BATH

  Paige Ryan Core Real Estate Team

  874 Co Rte 32, Chatham, NY 12132
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  /14

  $2,400 per month

  • 2 Baths
  • 2,100 Sq Ft
  • House for Rent

  15 Dardess Dr, Chatham, NY 12037

  2100 square feet of retail space in Chatham Plaza at the southern end of the Village of Chatham. The available space sits in the center of a healthy and active shopping plaza with ample parking. Convenient location, minutes to Main Street, Chatham, 20 minutes to Hudson. NNN lease.

  Jennifer Sesma Beach & Bartolo Realtors

  15 Dardess Dr, Chatham, NY 12037
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  /26

  $750,000 Sold Mar 27, 2025

  • 1,908 Sq Ft
  • $393/SF
  • 3 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1974

  361 Bushnell Rd Unit 2, Chatham, NY 12037

  On one of the prettiest country roads lies this charming and extremely well-maintained gambrel roof home on almost 8 secluded acres. Across the road, cows meander and one can view the ridges of farmland,while only 10 minutes from downtown Chatham.The home consists of 3 BR, 4 baths (primary ensuite) and is flooded with sunlight! A large stone wood burning fireplace in the living room creates

  Janet Kain The Kinderhook Group, Inc.

  361 Bushnell Rd Unit 2, Chatham, NY 12037
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  /9

  Not Listed For Sale

  1028 County Route 32, Chatham, NY 12115

  1028 County Route 32, Chatham, NY 12115
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  /30

  $750,000

  • 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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  /18

  $230,000 Sold Mar 26, 2025

  • 1,504 Sq Ft
  • $153/SF
  • 16 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1940

  2606 New York 66, Chatham, NY 12037

  If you've been dreaming of a home with character, potential, and a welcoming small-town vibe, this 3 bedroom, 1 bath property is your perfect match. With a large bedroom & sitting area graces the upstairs waiting for your creative touch, The Cape at 2606 could be your next masterpiece. Picture yourself relaxing in the spacious heated Sunroom, a perfect spot for enjoying a morning coffee or

  Angela Lanuto Coldwell Banker Village Green

  2606 New York 66, Chatham, NY 12037
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  /29

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  1384 Arnolds Mills Rd, Chatham, NY 12037

  1384 Arnolds Mills Rd, Chatham, NY 12037
• 

  

  /27

  $895,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,900 Sq Ft

  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
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  /24

  $425,000 Sold Mar 11, 2025

  • 2,900 Sq Ft
  • $147/SF
  • 15 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1987

  185 Hogle Hill, Chatham, NY 12037

  Beautiful panoramic views and just minutes from Chatham Village, this three bedroom, three bath house on almost four acres has much to offer. Enter into the main living area that has great views. The open concept large kitchen, dining and living areas have ample space for cooking & entertaining inside or out on the large deck. Enjoy expansive eastern, southern & western views throughout the day

  Sarah Lipsky Peggy Lampman Real Estate

  185 Hogle Hill, Chatham, NY 12037
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  /4

  Est $203,229 Not Listed For Sale

  3053 State Route 66, Chatham, NY 12037

  3053 State Route 66, Chatham, NY 12037
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  /44

  $784,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,850 Sq Ft

  26 Braley-Gleason Rd, Chatham, NY 12037

  This beautifully crafted post-and-beam house on 8.22 acres, can accommodate large gatherings but is equally suited to small family living. The main floor features a Great Room with Kitchen and Newly constructed Butler's Pantry, which are all laid out perfectly to enjoy the Views, or access the large Wraparound Deck. This floor also includes the Primary Bedroom w/ Ensuite, plus two additional

  Jeffrey McKinney Beach & Bartolo Realtors

  26 Braley-Gleason Rd, Chatham, NY 12037
• 

  $480,000 Sold Mar 07, 2025

  • 2,368 Sq Ft
  • $203/SF
  • 94 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1920

  55 Woodbridge Ave, Chatham, NY 12037

  Chatham two-family in the heart of the Village ready for investors. The lower unit has a spacious entry, leading into a light filled family room and dining area. A large modern kitchen and laundry area give room for additional dining. Two bedrooms and two baths comprise the rear of the unit. The upper unit utilizes a large entry landing as a mudroom and private entrance. Also outfitted with a

  Rachel Haley Houlihan Lawrence, Inc

  55 Woodbridge Ave, Chatham, NY 12037
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  /8

  Est $212,796 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,032 Sq Ft

  56 Church St, Chatham, NY 12037

  56 Church St, Chatham, NY 12037
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  /30

  $895,000 Under Contract

  • 4 Beds
  • 5 Baths
  • 2,563 Sq Ft

  230 Scannell Rd, Chatham, NY 12037

  Eden personified. A true country fairyland. Quiet dirt road leading to a dead quiet spot. Meander up the long private drive past the tennis court and swimming pond to a classic country shake and stone farmhouse. Walk through the gated garden to the front entry. High ceilings and views rolling over the pond. Flowering trees and gorgeous perennial gardens. Beamed ceilings and stone fireplace.

  230 Scannell Rd, Chatham, NY 12037
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  /36

  $577,000 Sold Mar 05, 2025

  • 2,800 Sq Ft
  • $206/SF
  • 76 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 2004

  1421 Albany Turnpike, Chatham, NY 12115

  One of a kind French Chateau style home with copper covered turrets sitting in the Hamlet of Malden Bridge. Along with the stone Chateau is the 1300 sq ft LOG GUEST HOME with 2 bd/2bath, living room w/fp, wood countertops in kitchen. The Chateau's first floor has stone floors with radiant heat, upstairs floors are wood, 25 stained glass windows. If you love to cook, you will appreciate this

  Karen Westman Berkshire Hathaway HomeServices Blake, REALTORS

  1421 Albany Turnpike, Chatham, NY 12115
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  /18

  Est $394,275 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft

  25 Church St, Chatham, NY 12037

  25 Church St, Chatham, NY 12037
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  /34

  $535,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 1.5 Baths
  • 1,375 Sq Ft

  77 Austerlitz St, Chatham, NY 12037

  This updated mid-century ranch offers significant improvements, including brand new wood floors, Marmoleum, and tile. Enjoy modern comfort with a new wood-burning insert, heat pump cooling/heating system, heat pump water heater, and two additional ductless split units. The home also features new appliances, a renovated basement, enhanced attic insulation, a backyard fence, a fabulous sunroom, and

  Kirsten Stoltmann Beach & Bartolo Realtors

  77 Austerlitz St, Chatham, NY 12037
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  /43

  $1,275,801 Sold Feb 28, 2025

  • 2,688 Sq Ft
  • $475/SF
  • 20 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2001

  801 Dugway Rd Unit 50, Chatham, NY 12037

  Follow a private drive through lakeside woods to 801 Dugway Road, a renovated country home nestled in 13.9 acres of sprawling lawns, woods, and old stone walls. Formerly used as the live-in studio of a well-known painter, this site boasts the potential for a myriad lifestyles and uses, be it an artists studio, wellness retreat, family country home or some combination of the three. The main house,

  Dina Palin Houlihan Lawrence Inc.

  801 Dugway Rd Unit 50, Chatham, NY 12037
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  /37

  Est $833,059 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,699 Sq Ft

  225 Slate Hill Rd, Chatham, NY 12037

  225 Slate Hill Rd, Chatham, NY 12037
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  /58

  $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 Kinderhook Group, Inc.

  5015 Crow Hill Rd, Chatham, NY 12037
• 

  $1,275,801 Sold Feb 28, 2025

  • 2,688 Sq Ft
  • $475/SF
  • 25 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2001

  801 Dugway Rd, Chatham, NY 12037

  Follow a private drive through lakeside woods to 801 Dugway Road, an airy country home nestled in 13.9 acres of sprawling lawns, woods, and old stone walls. Formerly used as the live-in studio of a well-known painter, this site boasts the potential for a myriad lifestyles and uses, be it an artists studio, wellness retreat, family country home or some combination of the three. The twenty eight

  Dina Palin Houlihan Lawrence, Inc

  801 Dugway Rd, Chatham, NY 12037
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  /19

  Est $267,058 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 966 Sq Ft

  35 Houseman Ave, Chatham, NY 12037

  35 Houseman Ave, Chatham, NY 12037
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  /6

  $370,000

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

  L8 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.

  Barry Shatney Bovair Real Estate

  L8 Cady Rd, Chatham, NY 12136
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  /3

  $195,975 Sold Feb 12, 2025

  • Land
  • 10 Acres
  • $19,082 per Acre

  • 171 Days On Market

  L.81.4 & 5 Pitts Rd, Chatham, NY 12136

  L.81.4 & L.81.5 Pitts Road - These two neighboring parcels, 5.27 acres (Tax ID 15.-1-81.4) and 5 acres (Tax ID 15.-1-81.5), offer a combined opportunity to create your custom dream home on a total of 10.27 acres. Both cleared and fully approved building lots boast stunning views from every angle. With stone walls and trees lining the properties, you'll experience the peace and privacy of your own

  Edith Kelly McCurdy Real Estate Group, Inc

  L.81.4 & 5 Pitts Rd, Chatham, NY 12136
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  /22

  Est $298,741 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,300 Sq Ft

  47 Houseman Ave, Chatham, NY 12037

  47 Houseman Ave, Chatham, NY 12037
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  /6

  $89,000

  • Land
  • 1.00 Acre
  • $89,000 per Acre

  0 County Route 9 Unit 156643, Chatham, NY 12037

  A little slice of heaven. Situated between the hamlets of New Concord and Red Rock this lot is ready for its future owners home. Percolation test has been done for a BOHA letter. There is an existing well on the property. Less than 10 minutes to Chatham with easy access to the Taconic state parkway from the East Chatham exit. Less than 30 minutes to Jiminy Peak, Hudson, Pittsfield, Lenox and

  Tyler Bervy Stone House Properties, LLC

  0 County Route 9 Unit 156643, Chatham, NY 12037
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  /18

  $700,000 Sold Jan 29, 2025

  • 2,472 Sq Ft
  • $283/SF
  • 17 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1840

  346 Fire Hill Rd, Chatham, NY 12037

  The E. Montross House was part of the original Falling Waters farm dating back to 1792 with the house built in the 1840s.. Set on 11 acres on one of the prettiest and quietest roads in the county. The history of the house comes through in the hand carved mouldings, wood panels and the patina in the floors. There are a number of King Boards in the flooring measuring over 12 wide. An enormous

  Emma French Gabel Real Estate

  346 Fire Hill Rd, Chatham, NY 12037
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  /27

  Est $866,630 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,608 Sq Ft

  43 Shufelt Rd, Chatham, NY 12037

  43 Shufelt Rd, Chatham, NY 12037
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  /25

  $379,000

  • 5 Beds
  • 4 Baths
  • 2,268 Sq Ft

  10 School St Unit 12, Chatham, NY 12037

  Discover this charming 1920's two-family home nestled off a quiet one-way side street in the Village of Chatham. This well-maintained duplex has so much to offer- lots of natural light, hardwood floors, updated kitchens & baths, vinyl clad Thermopane windows, vinyl siding, spacious living & dining rooms, a large back yard and each side offers an enclosed sunporch & laundry room. A smart

  Anne Harrison Country Life Real Estate, LLC

  10 School St Unit 12, Chatham, NY 12037
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  /6

  $715,000 Sold Jan 24, 2025

  • 2,700 Sq Ft
  • $265/SF
  • 0 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1776

  741 County Route 32, Chatham, NY 12037

  Two-story beauty situated in the hamlet of North Chatham, NY. This property boasts a rich history. The thoughtful upgrades, completed by the home's current occupants (one being a NYC-based architect), have allowed for greater conveniences and aesthetic appeal, without compromising integrity, Original white pine floors throughout the living and sleeping spaces have been refinished, fully

  741 County Route 32, Chatham, NY 12037
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  /31

  Est $418,530 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,240 Sq Ft

  1 Roxbury Rd, Chatham, NY 12037

  1 Roxbury Rd, Chatham, NY 12037
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  /86

  $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, and panoramic mountain views create a magnificent backdrop of natural splendor. The interior unfolds as a symphony of lavish indulgence, boasting the finest stainless steel appliances, a sumptuous sauna, 2 executive offices and a stunning wet bar within

  Vera Cohen Vera Cohen Realty, LLC

  189 Sutherland Rd, Chatham, NY 12132
• 

  $2,875,000 Sold Jan 10, 2025

  • 5,367 Sq Ft
  • $536/SF
  • 23 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2016

  247 Reed Rd, Chatham, NY 12037

  Follow a long drive through woods of pines and wildflowers to 247 Reed Road, a designer renovated contemporary home built to frame stunning views of the Hudson Valley hills and the Catskill Mountains beyond. The home sits on ten acres of sprawling green lawn and forest with a pool & open-air pool house. The site is as private as it is picturesque, exceptionally quiet yet just minutes to town.

  Annabel Taylor Four Seasons Sothebys Intl

  247 Reed Rd, Chatham, NY 12037
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  /16

  Est $421,539 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,757 Sq Ft

  18 Woodbridge Ave, Chatham, NY 12037

  18 Woodbridge Ave, Chatham, NY 12037
• 

  

  /162

  $2,500,000

  • 4 Beds
  • 3.5 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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  /30

  $675,000 Sold Dec 30, 2024

  • 2,660 Sq Ft
  • $254/SF
  • 70 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1972

  118 Loomis Rd, Chatham, NY 12037

  Experience a quiet country lifestyle in this 5 bedroom Colonial house on over ten acres and only 5 minutes from the vibrant Chatham Village. This house has it all with a first floor primary suite with en suite bath with walk-in shower, a large walk in closet, laundry room & very spacious bedroom with radiant heated floors, air conditioning & doors opening to a private outdoor deck with a vaulted

  Sarah Lipsky Peggy Lampman Real Estate

  118 Loomis Rd, Chatham, NY 12037

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