Homes for Sale near Chatham High School

• 

  

  

  /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
• 

  

  

  /38

  $565,000

  • 2 Beds
  • 2 Baths
  • 897 Sq Ft

  214 Fog Hill Rd, Austerlitz, NY 12017

  Tucked away on a country mountain road and set into the bucolic landscape of the Beebe Hill State Forest is Fog Hill Cabin. A modern cottage with a cabin-like feel. Recently the current owners have made significant upgrades to the cabin. These upgrades include an additional living area on the lower level that features its own kitchenette and en suite bathroom. A Mini Spit (heat pump) system

  

  Rachel Levine

  Patricia A. Hinkein Realty

  (518) 759-5502

  214 Fog Hill Rd, Austerlitz, NY 12017
• 

  

  

  /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
• 

  

  

  /28

  $789,000

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

  11549 State Route 22, Austerlitz, NY 12017

  Step back in time with this 1830's period gem set in a postcard setting with seasonal Green River frontage, hidden meadows and private footpaths inviting you to explore the natural beauty of the property. A fabulous screened porch looks out to the lush grounds and distant foothills. This 3 bedroom, 2 bath charmer offers timeless character with wideboard floors, two fireplaces and a rich

  Linnea VanTassel Country Life Real Estate, LLC

  11549 State Route 22, Austerlitz, NY 12017
• 

  

  

  /32

  $949,000

  • 3 Beds
  • 3 Baths
  • 4,377 Sq Ft

  1977 State Route 295, Canaan, NY 12029

  Live, work & play! Impressive post and best beam conversion offers the character of an earlier era while incorporating contemporary amenities.The exposed hand hewn beams exude a warm, rustic charm. There is an en suite primary plus 2 to 3 additional bedrooms and plenty of room forguests. Once a home to artists, the 15 x 38 studio room is perfect to create & display or convert into a yoga

  Philip Feiner Country Life Real Estate

  1977 State Route 295, Canaan, NY 12029
• 

  

  /70

  $699,000

  • 3 Beds
  • 2.5 Baths
  • 2,300 Sq Ft

  2640 New York 203 Unit 50, Valatie, NY 12184

  A rare retreat on 12+ private acres with stunning views of Kinderhook Creek—a Class A Trout stream—rolling farmland, pastures, and open meadows. This custom 2,300 sq ft log home blends rustic charm with modern comfort—featuring soaring ceilings, sunlit rooms, and a warm stone hearth with woodstove for cozy winter nights. The open layout includes a formal dining room, spacious kitchen, and a cool

  Teresa Kippen Field Realty

  2640 New York 203 Unit 50, Valatie, NY 12184
• 

  

  /17

  $782,000

  • 2 Beds
  • 2 Baths
  • 1,616 Sq Ft

  156 Mercer Mountain Rd, East Chatham, NY 12060

  A magical spot 1500' above sea level and offering 75 mile long views of the Catskill Mountains! Modern home with floor to ceiling windows to soak in the views while toasting toes in front of the fireplace. Clean lines and open floor plan. Two bedrooms plus a finished, walk-out basement. A one of a kind property located minutes to the Berkshires, Chatham, Hudson, or Albany.

  Terry Cozzolino Cozzolino Real Estate Inc

  156 Mercer Mountain Rd, East Chatham, NY 12060
• 

  

  /26

  $950,000

  • 5 Beds
  • 3.5 Baths
  • 3,894 Sq Ft

  291 Hennett Rd, Valatie, NY 12184

  Hilltop RefugeOpen, flowing, light filled 4 bedroom 3.5 bath home with en suite principal bedroom on the ground floor. In complete privacy this handsome residence with a beautiful flow offers generous size rooms with stunning views of rolling hills, woods and a big sky. The property was created for seamless entertaining and endless enjoyment. There is a run-in barn for animals and

  Miles Vidor Nicole Vidor Real Estate Inc.

  291 Hennett Rd, Valatie, NY 12184
• 

  

  /46

  $975,000

  • 3 Beds
  • 2 Baths
  • 1,907 Sq Ft

  18 Old Queechy Rd, Canaan, NY 12029

  RENOVATED ANTIQUE COLONIAL situated on expansive rolling bucolic property with mountain views. The house is located on a tree-lined country road, and is conveniently located between the towns of West Stockbridge and Chatham and within close proximity to Lenox and Tanglewood. The first floor of the house has an airy foyer with a wood-stove, formal dining room, fully modernized open-layout kitchen

  Tom Lynch Compass Greater NY LLC

  18 Old Queechy Rd, Canaan, NY 12029
• 

  

  /25

  $765,000

  • 5 Beds
  • 4 Baths
  • 3,165 Sq Ft

  53 Whitings Pond Rd, Canaan, NY 12029

  Step back in time in this sprawling, light filled, spacious gem. Huge front porch to sit in the shade of mature trees and perennials. Center hall branches off into large mostly original rooms with wide plank flooring, high ceilings, original period moldings and built in's. Large main bedroom on the first floor with walk in closet and bath. Country kitchen looking out over the special sun

  Leonard Brown Berkshire Hathaway HomeService

  53 Whitings Pond Rd, Canaan, NY 12029
• 

  

  /30

  $1,175,000

  • 4 Beds
  • 2 Baths
  • 2,505 Sq Ft

  54 Fowler Lake Rd, Ghent, NY 12075

  Tucked away on a quiet country road, this peaceful farmhouse sits on fifteen acres of native gardens, expansive lawns, wildflower meadows, blue stone patio and porches, and private forest with trails leading to the second spring-fed pond. Enter the house through an airy mudroom, then the Great Room lays out before you. The patio and pond draw you to the far end of the room, where French doors

  Annabel Taylor Four Seasons Sotheby's Int.

  54 Fowler Lake Rd, Ghent, NY 12075
• 

  

  /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
• 

  

  /47

  $745,000

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  263 Old Hudson Turnpike, Canaan, NY 12029

  PRICE CUT! All new eyebrow colonial transformed in to a modern efficient home with 3 bedrooms and 2 full baths. New Anderson windows, doors, roof, Smart siding. All new lighting throughout the house, new floors. All brand new appliances. Literally Brand new everything. New hot water heater tank with heat pump, water purification system. New Radon system.New wrap around deck to enjoy your

  Sharon McArdle Berkshire Hathaway Home Services Blake

  263 Old Hudson Turnpike, Canaan, NY 12029
• 

  

  /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
• 

  

  /21

  $149,900

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  158 Middle Rd, Austerlitz, NY 12017

  A Country Retreat!Discover your slice of paradise in this1972 vintage mobile home, nestled on a spacious 1.5-acre lot that is perfect for those seeking a peaceful country lifestyle.This home offers a large living room, kitchen with dining area, 2 bedrooms and full bath with laundry located in the hallway. There's a front deck to relax upon and the 1.5 acres means no close-by

  Barbara Robinson Red Apple Realty

  158 Middle Rd, Austerlitz, NY 12017
• 

  

  /45

  $1,290,000

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

  409 W Hill Rd, Austerlitz, NY 12017

  Meander through old growth trees down a paved private driveway to find a home with 360 degrees of privacy and 30 acres of lawns, perennial beds, meadows and forest. The main home boasts three bedrooms plus two large offices, a finished basement that can act as a playroom, media room or library. High ceilings and an open flow make the interior of the home abundant with natural light and serene

  Beth Cozzolino Gabel Real Estate

  409 W Hill Rd, Austerlitz, NY 12017
• 

  

  /5

  $325,000

  • Land
  • 24 Acres
  • $13,363 per Acre

  0 W Hill Rd Unit 20253831, Austerlitz, NY 12017

  Wonderful private parcel of land with wooded glens, open fields and Green River frontage. Views of Harvey Mountain. Usable land, close to the Berkshires. Frontage on two roads. Subdividable. Level land with mature trees. Great location close to the Berkshires, Hawthorne Valley School, Hudson and Chatham.

  Tracy Tassinari Gabel Real Estate

  0 W Hill Rd Unit 20253831, Austerlitz, NY 12017
• 

  

  /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
• 

  

  /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
• 

  

  /72

  $1,395,000 Open Sat 11AM - 1PM

  • 4 Beds
  • 2.5 Baths
  • 3,118 Sq Ft

  1185 County Route 22, Ghent, NY 12075

  Whispering Acres. An absolute Eden. A piece of land that grabs your heart. Usable land and undulating fields, a bridge over the Fitting Creek and past the springfed pond. 1790s colonial with all the original features. Wide pine floors with a gleaming patina of centuries past. Huge country kitchen leading to a large enclosed porch overlooking the grounds and flowering trees. Large center

  Tracy Tassinari Gabel Real Estate

  1185 County Route 22, Ghent, NY 12075
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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 overlooks a stocked pond-perfect for morning coffee or quiet evenings. The land is a highlight in itself: a seasonal stream runs along the back edge, groomed trails

  Rebecca Sullivan Miranda Real Estate Group Inc

  3041 State Route 66, Chatham, NY 12037
• 

  

  /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
• 

  

  /29

  $290,000

  • 2 Beds
  • 1 Bath
  • 1,099 Sq Ft

  28 Upper Queechy Rd, Canaan, NY 12029

  The home you've been looking for! This charming cottage with Queechy Lake rights offers comfortable living with modern amenities! The spacious chef's kitchen is the heart of the home, complemented by a separate living room, dining area, sunroom and bathroom on the first floor. Upstairs, you'll find a primary bedroom with ample space (including a cedar-lined walk-in closet,) a second bedroom, and

  Brian Wagner Beach & Bartolo Realtors

  28 Upper Queechy Rd, Canaan, NY 12029
• 

  

  /41

  $449,000

  • 3 Beds
  • 2 Baths
  • 2,259 Sq Ft

  638 Fog Hill Rd, Austerlitz, NY 12017

  Mid-century vibe with large light filled spaces creates the perfect setting to let your creativity flow. The expansive multiple purpose room off of the main living area is perfectly suited as a dance, yoga, music, or art studio space. Let your imagination run wild. First floor also includes two bedrooms and a full bath. On the lower level you will find an additional large bedroom with a wood

  Jennifer Capala WILLIAM PITT SOTHEBY'S - LENOX

  638 Fog Hill Rd, Austerlitz, NY 12017
• 

  

  /42

  $585,000

  • 3 Beds
  • 1.5 Baths
  • 1,482 Sq Ft

  230 Middle Rd, Austerlitz, NY 12017

  Welcome to Sugarwood Homestead, an adorable Cape-style home on 2 quiet acres in Austerlitz. This well-kept 3 bed, 1.5 bath property has a large living room with wood burning fireplace, a four-season sun porch, renovated kitchen, dining room, and 2-car garage. Upstairs there's a spacious primary bedroom, two smaller bedrooms, an updated full bath, and a 320 sq foot finished space that can serve as

  Anthony D'Argenzio Houlihan Lawrence

  230 Middle Rd, Austerlitz, NY 12017
• 

  

  /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
• 

  

  /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
• 

  

  /27

  $3,700,000

  • Land
  • 228 Acres
  • $16,221 per Acre

  120 Route 203, Austerlitz, NY 12017

  228 +/- acres with an Adirondack feel. Spectacular Catskill Mountain views with a 4 +/- acre crystal clear pond. A wonderful mix of open and wooded land with trails cut throughout. Bordered by protected NY State land and appointed with an equipment shed for storage. Perfect for the nature enthusiast. Convenient location just minutes to the TSP and Chatham, 20 minutes to Hudson & Gt Barrington and

  Anne Harrison Country Life Real Estate, LLC

  120 Route 203, Austerlitz, NY 12017
• 

  

  /20

  $75,000

  • Land
  • 4.74 Acres
  • $15,823 per Acre

  0 New York 22, Austerlitz, NY 12017

  Beautiful wooded lot on the Green River is a great spot to build your new home. The lot is 4.74 acres gently sloping upwards towards the east with the Green River running across the southwestern corner, so no bridge will be needed to access the land. Less than 5 mins to Beebe Hill State Forest, Harvey Mountain State Forest, Austerlitz Historical Society and Steepletop (the Edna St. Vincent

  Jennifer Sesma Beach & Bartolo Realtors

  0 New York 22, Austerlitz, NY 12017
• 

  

  /31

  $525,000

  • 3 Beds
  • 2 Baths
  • 1,430 Sq Ft

  797 State Route 203, Spencertown, NY 12165

  Charming 1923 Sears Arts & Crafts Bungalow - Timeless Elegance Meets Modern Comfort a rare and beautifully preserved home that radiates character, craftsmanship, and warmth. Nestled in the peaceful Spencertown hamlet this Sears home holds historic charm with thoughtful updates for today's lifestyle. Step inside through the inviting front porch(enclosed for year-round enjoyment) and experience the

  Qizhan Yao Realmart Realty, LLC

  797 State Route 203, Spencertown, NY 12165
• 

  

  /33

  $599,000

  • 4 Beds
  • 1.5 Baths
  • 1,968 Sq Ft

  9 Jones Ave, Chatham, NY 12037

  Welcome home!This thoughtfully restored 1880's village residence maintains its original integrity. The home has been meticulously renovated, featuring spacious rooms with lofty ceilings, abundant natural sunlight, and beautiful hardwood floors throughout.A beautiful front entryway opens to an elegantly curved staircase and parlor. Just beyond the French doors an inviting dining

  Lenore Packet Stone House Properties, LLC

  9 Jones Ave, 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
• 

  

  /12

  $160,000

  • Land
  • 8 Acres
  • $20,833 per Acre

  400 Mercer Mountain Rd, East Chatham, NY 12060

  Welcome to Mercer Mountain—an exclusive enclave of million-dollar-plus homes nestled in the rolling Taconic Mountains of Columbia County. Perfectly situated between the world-class cultural offerings of the Berkshires and the awe-inspiring Catskill Mountains, this remarkable 7.68-acre parcel offers a rare opportunity to build your dream estate in one of the Hudson Valley’s most sought-after

  Callan Bergmann Compass Greater NY, LLC

  400 Mercer Mountain Rd, East Chatham, NY 12060
• 

  

  /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
• 

  

  /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

Showing Results 1 - 40, Page 1 of 2