Homes for Sale near Chatham High School

• 

  

  

  /100

  $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
• 

  Explore 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
• 

  

  

  /100

  $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
• 

  

  

  /35

  $189,900

  • Land
  • 23.49 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

  $749,000 Open Sun 11AM - 1PM

  • 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
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  /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
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  /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 room w/closet in the 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
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  /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
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  /46

  $875,000

  • 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 MASSACHUSETTS , LLC GB

  18 Old Queechy Rd, Canaan, NY 12029
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  /42

  $840,000

  • 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
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  /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
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  /47

  $699,999

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

  263 Old Hudson Turnpike, Canaan, NY 12029

  PRICE REDUCTION TO SELL!! All brand new eyebrow colonial transformed in to a modern energy efficient home with 3 bedrooms and 2 full baths. New Anderson windows, doors, roof, insulation, 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

  Sharon McArdle Berkshire Hathaway Home Services Blake

  263 Old Hudson Turnpike, Canaan, NY 12029
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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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  /23

  $269,000

  • 4 Beds
  • 1 Bath
  • 1,900 Sq Ft

  767 Rock City Rd, Old Chatham, NY 12136

  This mid renovation home is situated on 6.58 acres where an overgrown pond was the little one's favorite cooling place in the summers of years gone by ... this 1900± sq ft, single floor home is comprised of L style open floor plan incorporating kitchen/dining area/living room---down the hall are 4 bedrooms and full bath. Downstairs is full poured cement basement under original home and crawl

  Natalia de Amorim Preferred Country Properties

  767 Rock City Rd, Old Chatham, NY 12136
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  /36

  $399,000

  • 4 Beds
  • 1.5 Baths
  • 2,020 Sq Ft

  2919 County Route 9, East Chatham, NY 12060

  The sweetest farmhouse—extensively renovated yet brimming with character. This home offers 4 bedrooms and 1.5 bathrooms, thoughtfully updated for comfort and style. A large eat-in kitchen, a fabulous mudroom and a well-kept basement add practicality. Step onto the gorgeous front porch and take in lovely pastoral views, or enjoy the yard with its garden beds, patio, and back deck. A detached

  Kate Lascar Compass Greater NY LLC

  2919 County Route 9, East Chatham, NY 12060
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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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  /4

  $395,000

  • Land
  • 10.03 Acres
  • $39,382 per Acre

  0 Macedonia Rd, Austerlitz, NY

  Hear a pin drop. Southern exposure and not a house in sight. Lovely 10 acre parcel in the Spencertown hills. Gorgeous swim pond and stream to fish. Open fields and gentle woods. A legacy property that has been in the same family for more than half a century.

  Tracy Tassinari Gabel Real Estate

  0 Macedonia Rd, Austerlitz, NY
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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
  • 34.33 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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  /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
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  /5

  $325,000

  • Land
  • 24.32 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
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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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  /72

  $1,395,000

  • 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
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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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  /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
• 

  

  /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

  $279,000

  • 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
  • 228.1 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
• 

  

  /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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