Homes for Sale near Chatham High School

• 

  

  

  /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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• 

  

  

  /42

  $855,000

  • 3 Beds
  • 2.5 Baths
  • 2,623 Sq Ft

  25 Ridge Rd, East Chatham, NY 12060

  Exceptional Views & Elevated ComfortPerched high above Mercer Road at the top of Ridge, this stunning 2,600+ sq ft contemporary home offers panoramic views that stretch across the valley to the Catskills—some of the best in the region. Set on 10 private acres, the home pairs modern ease with total tranquility.The vaulted great room, anchored by a floor-to-ceiling wood-burning

  Baris Demirel Serhant LLC

  25 Ridge Rd, East Chatham, NY 12060
• 

  

  

  /38

  $850,000

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  35 Jilroy Ln, Spencertown, NY 12165

  Spencertown Pond House: Your Private Sanctuary AwaitsTucked away on over 5 picturesque acres, the Spencertown Pond House offers an idyllic escape, where nature and comfort converge. With its own private, spring-fed pond visible from every room, this home is the epitome of serene, lakeside living. Imagine waking up each morning to breathtaking views of shimmering water, framed by lush greenery

  Dina Palin Houlihan Lawrence Inc.

  35 Jilroy Ln, Spencertown, NY 12165
• 

  

  

  /19

  $485,000

  • Land
  • 60 Acres
  • $8,066 per Acre

  0 County Route 5 & I90 Unit 202517807, Canaan, NY 12060

  Nestled in the coveted Taconic Mountains, known for their rugged beauty, rich wildlife, clear streams, and hidden ponds, this double parcel boasts over 60 acres in Canaan, NY offering both accessibility and seclusion. The Taconics create a tranquil, less-traveled alternative to the busier Berkshires, offering privacy, natural beauty, and easy access to state forests and rural charm. The front 15+

  Jessica Coutsonikas KW Platform

  0 County Route 5 & I90 Unit 202517807, Canaan, NY 12060
• 

  

  

  /16

  $485,000

  • Land
  • 60 Acres
  • $8,066 per Acre

  0 County Rte 5 & I90 Unit 20251524, Canaan, NY 12029

  Nestled in the coveted Taconic Mountains, known for their rugged beauty, rich wildlife, clear streams, and hidden ponds, this double parcel boasts over 60-acres in Canaan, NY offering both accessibility and seclusion. The Taconics create a tranquil, less-traveled alternative to the busier Berkshires, offering privacy, natural beauty, and easy access to state forests and rural charm. The front 15+

  Jessica Coutsonikas KW Platform

  0 County Rte 5 & I90 Unit 20251524, Canaan, NY 12029
• 

  

  /30

  $499,000

  • 2 Beds
  • 2.5 Baths
  • 1,650 Sq Ft

  11351 New York 22, Austerlitz, NY 12017

  Timeless Charm Meets Thoughtful Modernity on the Banks of the Green RiverNestled in the storybook hills of Austerlitz, NY—just 15 minutes from the heart of Chatham and 20 minutes to the cultural riches of Great Barrington—this fully renovated Cape Cod offers a rare blend of historic character and contemporary comfort. Set on 2.4 private acres with lush lawns, expansive planting beds, and

  John Barbato Compass, Hillsdale

  11351 New York 22, Austerlitz, NY 12017
• 

  

  /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
• 

  

  /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
• 

  

  /34

  $545,000

  • 6 Beds
  • 6 Baths
  • 2,816 Sq Ft

  19 - 21 Moore, Chatham, NY 12037

  Chatham Village Income Gem! This tastefully updated Craftsman two-family offers substantial investment return and steady income. Situated on a quiet village street, this meticulously maintained property with two spacious, side-by-side units, each featuring 3 bedrooms, an office area, sunroom, and large enclosed entryway. Enjoy a large yard, four-car garage, and storage/workshop. Recent

  Rachel Haley Houlihan Lawrence Inc.

  19 - 21 Moore, Chatham, NY 12037
• 

  

  /30

  $421,000

  • 4 Beds
  • 2.5 Baths
  • 1,850 Sq Ft

  1108 State Rt 295, East Chatham, NY 12037

  Come see this one. Kitchen is in and gorgeous. All brand new.Was on the market before as just a shell. You have to see it now that it is redone and finished. New everything inside and out. New septic and well, new front landscaping, new siding, roof, furnace, hot water heater, insulation, wiring, plumbing, hardwood floors downstairs, windows and doors. Downstairs bedroom ensuite with

  Leonard Brown Berkshire Hathaway HomeService

  1108 State Rt 295, East Chatham, NY 12037
• 

  

  /33

  $421,000

  • 4 Beds
  • 2.5 Baths
  • 1,846 Sq Ft

  1108 State Route 295 St, East Chatham, NY 12060

  Come see this one. Kitchen is in and gorgeous. All brand new.Was on the market before as just a shell. You have to see it now that it is redone and finished. New everything inside and out. New septic and well, new front landscaping, new siding, roof, furnace, hot water heater, insulation, wiring, plumbing, hardwood floors downstairs, windows and doors. Downstairs bedroom ensuite with

  Sharon McArdle Berkshire Hathaway Home Services Blake

  1108 State Route 295 St, East Chatham, NY 12060
• 

  

  /35

  $450,000

  • 2 Beds
  • 2 Baths
  • 1,634 Sq Ft

  2262 Rt 66, Ghent, NY 12075

  Clean, updated, turnkey and the location....directly next to The Bartlett House. This property is zoned Hamlet Business so you have options! Live and earn rental income or add this property to your investment portfolio. Each light filled unit consists of one BR, located in the rear of the house, a full bath, laundry, two ample sized closets, an open kitchen with plenty of room for a dining area,

  Melissa Dimassimo Stone House Properties, LLC

  2262 Rt 66, Ghent, NY 12075
• 

  

  /34

  $450,000

  • 2 Beds
  • 2 Baths
  • 1,634 Sq Ft

  2262 Rt 66 --, Ghent, NY 12075

  Clean, updated, turnkey and the location...directly next to The Bartlett House. This property is zoned Hamlet Business so you have options! Live and earn rental income or add this property to your investment portfolio. Each light filled unit consists of one BR, located in the rear of the house, a full bath, laundry, two ample sized closets, an open kitchen with plenty of room for a dining area,

  Melissa Dimassimo STONE HOUSE PROPERTIES, LLC

  2262 Rt 66 --, Ghent, NY 12075
• 

  

  /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
• 

  

  /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
• 

  

  /21

  $639,000

  • 3 Beds
  • 1.5 Baths
  • 1,700 Sq Ft

  477 Fog Hill Rd, Austerlitz, NY 12017

  Wonderful farmhouse with the best of all worlds. Renovated for modern use and function with old world charm. Pine floors. Great working kitchen with eating area. Large dining area for entertaining friends and family. Great room with high ceilings and Vermont Castings propane stove to warm the cooler spring nights, wrapped in windows to bring nature in. French doors off the eating area to large

  Tracy Tassinari Gabel Real Estate

  477 Fog Hill Rd, Austerlitz, NY 12017
• 

  

  /17

  $99,000

  • Land
  • 8 Acres
  • $12,532 per Acre

  2320 Route 295, Canaan, NY 12060

  Building lot with views of Queechy Lake on almost eight acres! Coveted lake rights accompany this mostly wooded lot with an old road meandering up to potential build sites. This is a perfect place to build a weekend getaway or your dream home. Nature abounds in this rural setting with mature trees, stone walls and wildlife everywhere. Surrounded on two sides by protected land, the location could

  Ryan Lane Gilcrest Properties

  2320 Route 295, Canaan, NY 12060
• 

  

  /42

  $475,000

  • 3 Beds
  • 2 Baths
  • 2,236 Sq Ft

  23 Leggett Rd, Ghent, NY 12075

  Welcome to this spacious ranch-style home, nestled on 1.5 acres of picturesque countryside. Offering three bedrooms and two and a quarter baths, this home is designed for comfort and versatility. The expansive primary suite includes a private en-suite bath, making it an excellent option for an in-law suite or a luxurious retreat. The heart of the home is the open-concept dining and family room,

  Dennis Wheeler, CBR, AHWD,SRES Berkshire Hathaway HomeService

  23 Leggett Rd, Ghent, NY 12075
• 

  

  /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
• 

  

  /23

  $2,500,000

  • Land
  • 101 Acres
  • $24,752 per Acre

  0 Iron Hill Rd, Austerlitz, NY 12037

  A perfect mix of rolling hills, open fields, tranquil woodland and stunning Catskill views. Centrally located, five minutes from the Chatham exit off the Taconic Parkway, 20 min to Hudson, Lenox, and Great Barrington.

  Tyler Bervy Stone House Properties, LLC

  0 Iron Hill Rd, Austerlitz, NY 12037
• 

  

  /55

  $589,000

  • 5 Beds
  • 3 Baths
  • 3,180 Sq Ft

  105 McNamee Rd, Canaan, NY 12029

  2024 Renovation of Queechy Lake Year Round Private Recreational Retreat on 3 Levels with own private boat launch & beach and minutes to Ski Jiminy. Currently operating as successful Air BNB with separate owner living space. Brand new furnishings included: ready to go!! Be Sure to Check Out Virtual Media Tour. 3rd floor recently finished with new bath. Other floors recently renovated. Organized to

  David Birch Barns & Farms Realty

  105 McNamee Rd, Canaan, NY 12029
• 

  

  /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
• 

  

  /16

  $5,100,000

  • Land
  • 517 Acres
  • $9,865 per Acre

  0 W Hill Rd Unit 155309, Austerlitz, NY 12017

  517 ACRES. Country living and hunter's paradise within a stone's throw of the famous Berkshire and Catskill Mountains. This property is the perfect location for the active outdoorsman or nature enthusiast. With miles of forestry, trails, and privacy, excellent fishing, ATV, and Snowmobile trails in the area, making this a haven for year-round recreation. Private, level, sloping, and wooded, this

  Michael Tellerday Houlihan Lawrence, Inc.

  0 W Hill Rd Unit 155309, Austerlitz, NY 12017
• 

  

  /27

  $545,000

  • 6 Beds
  • 4 Baths
  • 2,816 Sq Ft

  21 Moore Ave, Chatham, NY 12037

  Chatham Village two-family with substantial investment return and steady income producer available. The tastefully updated craftsman is set on a quiet village street with a large yard, two car garage, and storage/workshop area. The side by side two-level units both have 3 bedrooms, office area, sunroom, and large enclosed entryway. Recent improvements include; chimney rebuild and cap,

  Rachel Haley Houlihan Lawrence, Inc

  21 Moore Ave, Chatham, NY 12037
• 

  

  /4

  $299,000

  • Land
  • 11 Acres
  • $27,182 per Acre

  0 Engel Rd Unit 154439, Austerlitz, NY 12037

  Quiet Lot on a Dead End RoadIts the perfect building lot to make a home for yourself. Private and quiet.

  Emma French Gabel Real Estate

  0 Engel Rd Unit 154439, Austerlitz, NY 12037
• 

  

  /4

  $299,000

  • Land
  • 11 Acres
  • $27,182 per Acre

  L59.100 Engel Rd, Austerlitz, NY 12037

  Quiet Lot on a Dead End RoadIts the perfect building lot to make a home for yourself. Private and quiet.

  Andrea Gabel Gabel Real Estate

  L59.100 Engel Rd, Austerlitz, NY 12037
• 

  

  /20

  $499,000

  • 2 Beds
  • 1.5 Baths
  • 1,200 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
• 

  

  /6

  $219,000

  • Land
  • 5.00 Acres
  • $43,800 per Acre

  0 Reed Rd Unit 153134, Austerlitz, NY 12037

  Punsit Valley and Catskill Mountain views from this usable 5 acre parcel. Privately tucked on one of Spencertown's prettiest roads. Usable land, easy to build on. Close to town, yet totally private and quiet. Western sunsets and valley views. Great spot for a spec house. Wonderful value.

  Tracy Tassinari Gabel Real Estate

  0 Reed Rd Unit 153134, Austerlitz, NY 12037
• 

  

  /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
• 

  

  /12

  $795,000

  • Land
  • 63 Acres
  • $12,619 per Acre

  0 Old Macedonia Rd Unit 153065, Austerlitz, NY 12107

  Top of world surrounded by State Forest for forever privacy. 63 acres of western sunsets, Berkshire Hills and the valley below. Trails and roughed in driveway to start your building project. Perfect for hunting, riding and all outdoor activities. See Albany through to the Shawangunk Mountains. An expanse rarely found today. Pin drop quiet. Close to State Forest for additional hiking or mountain

  Tracy Tassinari Gabel Real Estate

  0 Old Macedonia Rd Unit 153065, Austerlitz, NY 12107
• 

  

  /16

  $599,999

  • Land
  • 70 Acres
  • $8,571 per Acre

  1 W Hill Rd, Austerlitz, NY 12017

  70 ACRES Surrounded by the beauty and serenity of nature, this parcel is perfect for the active outdoorsman, hunter, nature lover, or hiking enthusiast, as there are trails galore available for use. Or, build your dream home on this private, level, sloping, and wooded parcel with topography that lends to potential views to the east and south with clearing. There are two possible access points,

  Michael Tellerday Houlihan Lawrence, Inc.

  1 W Hill Rd, Austerlitz, NY 12017
• 

  

  /13

  $369,000

  • Land
  • 22 Acres
  • $16,773 per Acre

  0 Amy's Ln Unit 152415, Austerlitz, NY 12017

  22 Acres on quiet byway with striking view of Berkshires. Adjoins other luxury properties. Easy commute to Tanglewood and the Berkshires. BOHA private building site with driveway and views of Berkshire Mountains. Close to Hillsdale, Chatham and Canaan and not far from Hudson. Please look at the approved plans for a Gatehouse/garage, under category "other" Complete approved plans are available.

  David Birch Barns & Farms Realty, LLC

  0 Amy's Ln Unit 152415, Austerlitz, NY 12017
• 

  

  /20

  $1,995,000

  • Land
  • 275 Acres
  • $7,255 per Acre

  3 W Hill Rd, Austerlitz, NY 12017

  275 ACRES. Country living and hunter's paradise within a stone's throw of the famous Berkshire and Catskill Mountains. This property is the perfect location for the active outdoorsman or nature enthusiast. With miles of forestry, trails, and privacy, this is the place you envision those trophy Whitetails hiding out. When you're not hunting, you'll find excellent fishing, ATV, and Snowmobile

  Joy Lombardo

  3 W Hill Rd, Austerlitz, NY 12017
• 

  

  /15

  $1,500,000

  • Land
  • 205 Acres
  • $7,317 per Acre

  2 W Hill Rd, Austerlitz, NY 12017

  205 ACRES Among the vast expanse of trees lies the serenity and peacefulness of nature on this fantastic parcel of land. View the panoramic beauty on this 205-acre lot of pure bliss. Topography lends spectacular potential views to the south, west (Catskills), and north. Private, level, sloping, and wooded, this parcel has all the right specs for building your dream home or family compound.

  Joy Lombardo

  2 W Hill Rd, Austerlitz, NY 12017
• 

  /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
• 

  

  /29

  $525,000 New Construction

  • 1 Bath
  • 600 Sq Ft

  208 E East Hill Rd, Austerlitz, NY 12017

  Your Private Waterfall Retreat: New Cabin Backing State ForestDiscover unparalleled tranquility at this newly built, top-quality cabin. Tucked away on a quiet dirt road, a private drive leads you past your own stream and picturesque waterfall, right to your door.This beautifully designed cabin features an open floor plan with a comfortable sleeping loft, and a huge deck perfect for

  Rachel Haley Houlihan Lawrence Inc.

  208 E East Hill Rd, Austerlitz, NY 12017
• 

  

  /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
• 

  

  /48

  $1,250,000 Coming Soon

  • 4 Beds
  • 3 Baths
  • 2,500 Sq Ft

  21C County Route, Ghent, NY 12075

  This picturesque four-bedroom, three-bath 1800's farmhouse has been lovingly restored and thoughtfully updated, blending timeless historic farmhouse charm with modern comfort, including fiber-optic internet. Set on 18.5 acres of pure serenity, it offers a storybook setting with two meandering streams, an enchanting spring-fed pond, and a rolling lawn that opens to forests and trails. The

  Nancy Felcetto Brown Harris Stevens HV LLC

  21C County Route, Ghent, NY 12075
• 

  

  /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

Showing Results 41 - 79, Page 2 of 2