Chatham, NY Homes for Sale

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  /64

  $828,000

  • 3 Beds
  • 2.5 Baths
  • 2,267 Sq Ft

  23 Frog Aly, Old Chatham, NY 12136

  Timeless farmhouse charm meets modern luxury in the heart of Old Chatham. Set on 1.4 picturesque acres, this beautifully renovated 1875 home has been thoughtfully restored from top to bottom, blending historic character with contemporary comfort. Inside, you'll find sun-filled living spaces, gleaming hardwood floors, a gourmet kitchen featuring a Wolf range, Bosch appliances, quartz countertops,

  

  Richard Byrne

  Four Seasons Sotheby's Int.

  23 Frog Aly, Old Chatham, NY 12136
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  /37

  $3,595,000

  $400K PRICE DROP

  • 6 Beds
  • 5 Baths
  • 12,000 Sq Ft

  147 Rock City Rd, Old Chatham, NY 12136

  A rare offering of scale, privacy, and refinement, Bellavista Country Estate is a magnificent 12,000-square-foot Georgian brick residence set on over 25 secluded acres in the foothills of the Berkshires, perfectly positioned between the Hudson River Valley and the Berkshires. Designed for elegant country living at the highest level, the estate offers six to nine beautifully appointed bedrooms,

  

  Joseph Briggs

  William Pitt Sothebys International Real

  147 Rock City Rd, Old Chatham, NY 12136
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  /31

  $3,995,000

  $500K PRICE DROP

  • 10 Beds
  • 6 Baths
  • 5,000 Sq Ft

  33 Ford Rd, Old Chatham, NY 12136

  CEDAR HILL - Architectural Country Living at its Finest - is the embodiment of 21st-century modern luxury. Elevated on 10 private acres with sweeping mountain views, a gracious mix of open and wooded landscape, a serene spring-fed lily pond, and an organic vegetable garden, this newly expanded and reimagined six-bedroom home is set in Old Chatham, one of the most coveted corners of New York's

  Nancy Felcetto BROWN HARRIS STEVENS HUDSON

  33 Ford Rd, Old Chatham, NY 12136
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  /61

  $1,585,000

  $290K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,908 Sq Ft

  41 Chicory Ln, Chatham, NY 12037

  Welcome to Chicory Hill House, a unique designer home set at the end of a long private driveway on 20 beautiful acres located in Columbia County, prime Hudson Valley. The property features pastoral views, a year-round creek, and a small waterfall woven into the landscape. Following an extensive high-end renovation and infrastructure overhaul, the original 1985 contemporary has been transformed

  Anthony D'Argenzio Houlihan Lawrence Inc

  41 Chicory Ln, Chatham, NY 12037
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  /8

  $108,000

  • 3 Beds
  • 2 Baths
  • 880 Sq Ft

  1903 Route 203 Unit 104, Chatham, NY 12037

  2013 3 bedroom, 2 full bath manufactured home available for sale. $108,000. Edgewood Acres is a quiet neighborhood with an authentic country vibe. You can walk to Chatham Village and find one-of-a-kind retail stores, restaurants and galleries. This rural upstate New York community is open, friendly, and welcoming. Crellin Community park is walking distance from downtown Chatham with playgrounds,

  Darice Joerman Garden Homes Management

  1903 Route 203 Unit 104, Chatham, NY 12037
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  /25

  $399,000

  $51K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,433 Sq Ft

  953 Albany Turnpike, Old Chatham, NY 12136

  Charming 3-Bedroom Ranch on 14 Acres in Old Chatham, NY Discover peaceful country living at its finest in this inviting 3-bedroom ranch-style home, nestled on a sprawling 14-acre parcel in Old Chatham. Offering the perfect blend of comfort, functionality, and outdoor adventure, this property is ideal for horse enthusiasts, nature lovers, and those seeking a private retreat just minutes from

  Tyler Bervy Stone House Properties, LLC

  953 Albany Turnpike, Old Chatham, NY 12136
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  /18

  $560,000

  $75K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 2,862 Sq Ft

  139 Haddock Hill Rd, Old Chatham, NY 12136

  A Grand Dame in Old Chatham. Discover the joy in bringing back a classic. All the bones are solid. Five bedrooms in that rambling feel that makes farmhouses so lovable. The great room fireplace combines stone and real wood panels with views of the pond out the windows. A formal dining with wainscoting leads to a kitchen that leads out back. A second living room that could be it's own apartment.

  Andrea Gabel Gabel Real Estate

  139 Haddock Hill Rd, Old Chatham, NY 12136
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  /19

  $135,000

  $50K PRICE DROP

  • Land
  • 18,295 Sq Ft
  • $321,429 per Acre

  0 Murray St, Chatham, NY 12037

  RARE buildable lot available in the Village of Chatham on just under .5 acre set up and off of private dead-end road with seasonal views of the Catskill Mountains and the Clock Tower in Chatham. Easy, short walk into the village or to Borden's Pond Conservation Area. Loads of space to build within village setbacks. Property has a bit of a grade allowing building site to be up and back with a

  Amber McPhail Illustrated Properties Group

  0 Murray St, Chatham, NY 12037
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  /13

  $275,000

  • Land
  • 37 Acres
  • $7,432 per Acre

  L 70 Richmond Rd, Chatham, NY 12115

  Discover 37 acres of classic Columbia County countryside where open meadows meet a magnificent hardwood forest, creating the perfect balance of sun-drenched fields and peaceful woodland. Wander beneath a canopy of towering oak and maple as sunlight filters through the leaves, illuminating moss-covered stone walls and quiet paths that invite exploration in every season.Nature lovers will

  Michael Castellano Gilcrest Properties

  L 70 Richmond Rd, Chatham, NY 12115
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  /20

  $114,900

  $14K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 998 Sq Ft

  296 New York 295, 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 functional kitchen

  Margaret Guerra Trevett Group LLC

  296 New York 295, Chatham, NY 12037
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  /66

  $1,598,000

  • 3 Beds
  • 2.5 Baths
  • 3,173 Sq Ft

  13 Elm St, Chatham, NY 12037

  OPEN HOUSE SUNDAY AUGUST 9 - 11AM to 1 PM. Refined and classic elegance abounds in this historic and prominent Spencertown hamlet home. Built in 1810 as a fashionable Federal Style home, it featured magnificent details and craftsmanship throughout. Step back in time in this glorious and updated property. The abundance of 19th century luxury features have been lovingly restored and enhanced from

  Peter Newman Beach & Bartolo Realtors

  13 Elm St, Chatham, NY 12037
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  /11

  $56,000

  $14K PRICE DROP

  • Land
  • 7.65 Acres
  • $7,320 per Acre

  L90 County Route 9, East Chatham, NY 12060

  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

  L90 County Route 9, East Chatham, NY 12060
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  /51

  $1,745,000

  $150K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,922 Sq Ft

  160 Beale Rd, Chatham, NY 12037

  Located on one of Columbia County's finest roads in the town of Spencertown, this impeccably-maintained private 2922 sq ft. colonial home on 7.4 acres has all of the modern amenities! A fabulous setting with stunning distant views, the home features an open chef's kitchen and great room plan, which was expanded and redesigned in 2021, with Sub Zero refrigerator, Wolf gas oven and Miele dishwasher

  Janet Kain The Kinderhook Group, Inc.

  160 Beale Rd, Chatham, NY 12037
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  /5

  $499,000

  • Land
  • 63.44 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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  /40

  $899,000

  $180K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,688 Sq Ft

  275 Pitts Rd, Old Chatham, NY 12136

  Recently renovated and thoughtfully updated, the streamside cottage and separate guest studio were once part of the historic Wigton Lester Farm, with origins dating back to the early 1800s. Nestled on 5 acres along one of the most picturesque roads in Old Chatham, the property is surrounded by open meadows, historic stone walls, and a gently winding stream that, over generations, has carved its

  Michael Tellerday Houlihan Lawrence Inc.

  275 Pitts Rd, Old Chatham, NY 12136
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  /27

  $895,000

  • 4 Beds
  • 3 Baths
  • 3,554 Sq Ft

  4259 State Route 203, Chatham, NY 12037

  Set within the historic hamlet of North Chatham, this beautifully restored c.1830 Greek Revival side-hall farmhouse is a wonderful example of the understated elegance that defined rural Columbia County architecture during the period. The home's classic side-hall plan, refined Greek Revival moldings, hand-hewn beams, wide-plank pine floors, and beautifully preserved millwork speak to its early

  Annabel Taylor Four Seasons Sothebys Intl

  4259 State Route 203, Chatham, NY 12037
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  /25

  $675,000

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

  25 Lovers Ln, Valatie, NY 12184

  Welcome to the original early 1800's John Jay van Valkenburgh home in the quaint and historic hamlet of Chatham Center.This three bedroom, charming two-story colonial farmhouse on 1.6 acres features original wood beams, a working fireplace with wood stove insert in the large open living room, hardwood floors and an adjoining dining room with a cast iron wood stove. A modern kitchen with

  Janet Kain The Kinderhook Group, Inc.

  25 Lovers Ln, Valatie, NY 12184
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  /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
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  /73

  $2,600,000

  $295K PRICE DROP

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

  311 County Road 13, Old Chatham, NY 12136

  Set in the heart of Old Chatham, this classic Colonial rests on an exceptional 101-acre landscape of rolling pasture, woodland, and wide-open country views. From its elevated vantage point, the home looks out over a 2.5-acre swimmable pond, open fields, and a stretch of Hudson Valley scenery that changes beautifully with the seasons. Flooded with natural light, the seven-bedroom home offers

  Nikki Carchedi STONE HOUSE PROPERTIES, LLC

  311 County Road 13, Old Chatham, NY 12136
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  /20

  $14,000

  $2K PRICE DROP

  • 4 Beds
  • 3.5 Baths

  323 Haddock Hill Rd, Old Chatham, NY 12136

  Welcome to Rock Hill North, an idyllic Upper Hudson Valley rental home in Old Chatham. Situated on 10 private acres, the new build is a modern take on a traditional barn house. The home features open living spaces, 3-4 bedrooms, 3.5 bathrooms, and additional second level rooms for office, studio, or fitness room. The primary suite, with its own patio, has views of the Taconic Foothills. Featuring

  Rachel Haley COMPASS MASSACHUSETTS , LLC GB

  323 Haddock Hill Rd, Old Chatham, NY 12136
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  /22

  $615,000

  $40K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft

  2318 County Route 9, East Chatham, NY 12060

  Tucked down a quiet country road, 2318 County Route 9 is the kind of place that feels like it's been waiting for you. Set on over five acres, this three bedroom, one bath cottage is thoughtfully designed from the inside out, every corner telling a story, every detail chosen with care.Sunlight pours through every window, framing the beauty of lush gardens and the natural world just beyond the

  Shaina Marron Houlihan Lawrence, Inc

  2318 County Route 9, East Chatham, NY 12060
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  /25

  $475,000

  $24K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,300 Sq Ft

  1129 New York 295, East Chatham, NY 12060

  Lucrative income property in the center of a New England hamlet's business district. Minutes to Taconic State Parkway/I90/Berkshire Spur, 15 minutes to Lenox/Tanglewood, 30 minutes Albany/Capital Region. 3 buildings fully occupied incl 2BR/1.5BATH center hall 1930's home w/LG foyer staircase flanked by LG common RMS incl LR w/wood fireplace opposite spacious DR. Wood flrs throughout and leased

  Natalia de Amorim Preferred Country Properties

  1129 New York 295, East Chatham, NY 12060
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  /32

  $510,300

  $26K PRICE DROP

  • Land
  • 63.1 Acres
  • $8,087 per Acre

  L8 Lower Cady Rd, Chatham, NY 12136

  Buyers don't miss out on this one. If looking to build your dream home or a hunting enthusiast , you have found a private country property located near a quiet historic community . Just minutes to the N.Y.S Thruway & Taconic State Parkway and an easy drive to NYC or a short drive to the Berkshires for all seasonal activities. After storing the recreational vehicles, enjoy the wildlife along side

  Barry Shatney Bovair Real Estate

  L8 Lower Cady Rd, Chatham, NY 12136
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  /38

  $559,000

  $40K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,043 Sq Ft

  1501 County Road 28, Valatie, NY 12184

  Light-filled, charming 4 Bedroom/3.5 bath 1800s farmhouse with two ensuites -- including one on the first floor that can, alternatively, serve as a home office. Also on the first floor is a great room with high ceilings, a wood burning fireplace and French doors with access to the 24' x 24' deck. The home is set for entertaining with an easy flow from the eat-in kitchen, to the dining room, or

  Jennifer Wall Anderson Agency

  1501 County Road 28, Valatie, NY 12184
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  /2

  $690,000

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

  1896 County Route 9, Chatham, NY 12037

  Amazing Victorian style investment opportunity in Chatham, NY. Local attractions in area include OomsConservation area at Sutherland Pond or catching a musical at the Mac-Haydn Theatre. This Victorian Style home shows it was built in 1886. Total square footage is showing on tax records at 4,307 sq. ft. An amazing large lot of 918,680 sq. ft. An opportunity as such comes across once in a

  Neven Spralja Realhome Services & Solutions, Inc

  1896 County Route 9, Chatham, NY 12037
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  /51

  $649,900

  $125K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,005 Sq Ft

  2228 New York 203, Chatham, NY 12037

  Located only 30 minutes from the Hudson Amtrak Train Station this 9.5-acre property in Chatham, NY offers exceptional potential one of which could be an organic farm. With multiple structures there are endless possibilities. An amazing 2 story huge barn would work for an artist/actor or musician studio and wouild also work for horses. There is a private pond for swimming, kayajing and fishing.

  Claudia Zucker Living Structures

  2228 New York 203, Chatham, NY 12037
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  /65

  $1,599,000

  • 6 Beds
  • 5 Baths
  • 5,738 Sq Ft

  20 Stony Knoll, Valatie, NY 12184

  Tucked away on 10 private acres in the heart of Chatham, this stunning country estate offers over 5,700+square feet of beautifully designed living space with the perfect balance of luxury, comfort, and privacy. Set far back from the road, the property welcomes you with peaceful surroundings, a scenic pond, and room to truly spread out and enjoy country living. Inside, the home features 6 spacious

  Thomas Trevett Trevett Group LLC

  20 Stony Knoll, Valatie, NY 12184
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  /28

  $349,000

  • 4 Beds
  • 1.5 Baths
  • 1,214 Sq Ft

  1976 State Route 203, Chatham, NY 12037

  Set along scenic Route 203, this four-bedroom home enjoys easy access to the vibrant Village of Chatham, where beloved restaurants, local shops, farmers markets, and cultural attractions create one of Columbia County's most sought-after communities. Inside, the home offers a practical floor plan with comfortable living spaces and abundant potential for updates and personalization. Whether you're

  Nikki Carchedi Stone House Properties, LLC

  1976 State Route 203, Chatham, NY 12037
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  /35

  $725,000

  • 3 Beds
  • 2 Baths
  • 2,357 Sq Ft

  8 Chapel Dr, Valatie, NY 12184

  Perched above the tranquil waters of Kinderhook Lake, The Lady of the Lake is one of Columbia County's most unforgettable homes--a thoughtfully restored former church transformed into a design-forward retreat where historic architecture meets modern luxury.Rich with character and reimagined with an exceptional eye for design, this three-bedroom, two-bath residence effortlessly blends original

  Catherine Quintard Compass Greater NY, LLC

  8 Chapel Dr, Valatie, NY 12184
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  /29

  $3,000,000

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

  189 Sutherland Rd, Chatham, NY 12132

  Welcome to Sutherland Estate, a private country compound set on more than 56 acres of rolling meadows, gardens, ponds, with Catskill Mountain views. A long paved drive leads to this elegantly designed 5,760-square-foot home, inspired by classic Greek Revival architecture and recently renovated from top to bottom with refined, high-end craftsmanship. The home features a standing-seam metal roof,

  Macarena Tracey Rouse + Co Real Estate

  189 Sutherland Rd, Chatham, NY 12132
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  /69

  $1,499,000

  $100K PRICE DROP

  • 6 Beds
  • 5 Baths
  • 5,364 Sq Ft

  20 Stony Knoll, North Chatham, NY 12132

  Tucked away on 10 private acres in the heart of Chatham, this stunning country estate offers over 5,700+ square feet of beautifully designed living space with the perfect balance of luxury, comfort, and privacy. Set far back from the road, the property welcomes you with peaceful surroundings, a scenic pond, and room to truly spread out and enjoy country living. Inside, the home features 6

  Margaret Guerra Trevett Group LLC

  20 Stony Knoll, North Chatham, NY 12132
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  /32

  $599,000

  $150K PRICE DROP

  • 9 Beds
  • 6 Baths
  • 6,935 Sq Ft

  1121 New York 295, East Chatham, NY 12060

  2-Story/5-Apartment/9BR/6BA building PLUS 2BR/1BA Ranch home on about a half acre. Fully occupied, leases, both structures fully up to date and move-in condition. Tenants pay all utils. Landlord provides maintenance, snow/trash removal, water/sewer, off-street parking, fridge/stove each unit. 2 SBL lot numbers - properties not sold separately. Assessment/tax figures herein reflect total due for

  Natalia de Amorim PREFERRED COUNTRY PROPERTIES

  1121 New York 295, East Chatham, NY 12060
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  /20

  $495,000

  $100K PRICE DROP

  • 5 Beds
  • 2 Baths
  • 1,872 Sq Ft

  52 Church St, Chatham, NY 12037

  Welcome to 52 Church Street, a c.1900 home set on a generously-sized quarter acre lot in the Village of Philmont. Enter through a large mudroom flanked with windows. A stylish living room flows seamlessly to a large kitchen overlooking the yard. Numerous windows and a door leading to the backyard flood the kitchen space with light. A hall leads to a second kitchen, bedroom and full bath, perfect

  MATTHEW CAREY Rouse + Co Real Estate

  52 Church St, Chatham, NY 12037
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  /61

  $375,000

  • 5 Beds
  • 3 Baths
  • 3,146 Sq Ft

  22 Spring St, Chatham, NY 12037

  Fully Rented Income Property in the heart of Chatham Village NY. 3 non-owner-occupied units. All photos taken pre-occupancy. 5BRS total, 3 full baths. Municipal water/sewer. Private off-street parking. Total acreage for 2 parcels (66.6-1-45 is 0.23 acre and 66.6-1-48 is 0.24 acre). Total tax figures below include both parcels. A minute drive to Main St and all shops, theater, pubs, restaurants,

  Natalia de Amorim Preferred Country Properties

  22 Spring St, Chatham, NY 12037
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  /5

  $150,000

  • Land
  • 15.5 Acres
  • $9,677 per Acre

  L53 New York 66, Chatham, NY 12115

  Discover the possibilities on this 15.5-acre parcel in the desirable hamlet of Malden Bridge. Once home to grazing dairy cows, this open and fertile land is ready for its next chapter. Whether you're looking to start a small farm, establish a homestead, raise livestock, grow crops, or simply invest in agricultural land, this property offers plenty of opportunity.The gently rolling landscape

  Michael Castellano Gilcrest Properties

  L53 New York 66, Chatham, NY 12115
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  /24

  $299,000

  $26K PRICE DROP

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

  1135 New York 295, East Chatham, NY 12060

  1800's Hamlet icon. 1st floor retail, 2nd floor 3BR Apt. 3000sqft total incl 50x25' open retail space w/ 3/4 bath (incl shower), 2 storage rms and walkout to rear yard. 2nd flr features residential apt w/50' great rm LR/DR/Kitchen, 3 BRS, full bath. Detached 1.5-car garage plus parking on site and across the street. 8 miles to Berkshires, 5 to Chatham Village and I90/Taconic Parkway. High

  Natalia de Amorim Preferred Country Properties

  1135 New York 295, East Chatham, NY 12060
• 

  

  /21

  $575,000

  $75K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 825 Sq Ft

  896 County Route 13, Old Chatham, NY 12136

  Nestled within the serene hamlet of Old Chatham, this exceptional country home offers 43 private acres with stream frontage and abundant wildlife. Thoughtfully renovated and impeccably maintained, the residence seamlessly blends timeless rural character with modern comfort. Recent enhancements include a beautifully redesigned kitchen and bath, upgraded sound attenuation for enhanced privacy, a

  Mary Turoci Keyology

  896 County Route 13, Old Chatham, NY 12136
• 

  

  /50

  $7,995,000

  $4M PRICE DROP

  • 8 Beds
  • 10 Baths
  • 8,000 Sq Ft

  47 White Bridge Rd, Old Chatham, NY 12136

  Where History Breathes and Beauty Dwells: WHITE BRIDGE FARM c1775 Welcome to White Bridge Farm, an exquisite historic18th century estate restored and designed honoring and preserving the history with imagination and perfection. White Bridge Farm will take your breath away at every turn from the original restored iron main gate to magical stonewalls, pathways and gardens landscaped to intrigue all

  Nancy Felcetto Brown Harris Stevens HV LLC

  47 White Bridge Rd, Old Chatham, NY 12136
• 

  

  /77

  $2,600,000

  $295K PRICE DROP

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

  311 County Route 13, Old Chatham, NY 12136

  Set in the heart of Old Chatham, this classic Colonial rests on an exceptional 101-acre landscape of rolling pasture, woodland, and wide-open country views. From its elevated vantage point, the home looks out over a 2.5-acre swimmable pond, open fields, and a stretch of Hudson Valley scenery that changes beautifully with the seasons. Flooded with natural light, the seven-bedroom home offers

  Nikki Carchedi Stone House Properties, LLC

  311 County Route 13, Old Chatham, NY 12136
• 

  

  /40

  $1,995,000

  $305K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,500 Sq Ft

  300 Dugway Rd, Chatham, NY 12037

  Camp DugwayA home that evokes the great camps of the Adirondacks within 2 hours of Manhattan. Cross the bridge over a babbling brook to a setting straight out of a Cooper novel. Three cascading waterfalls frame the view. The pond sits just off the bluestone patio. Inside a blend of craftsman style and great camp ambiance in every room. The fieldstone in the fireplace came from the land as did

  Andrea Gabel Gabel Real Estate

  300 Dugway Rd, Chatham, NY 12037

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