Houses for Sale near Chatham High School

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  /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
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  Explore Chatham High School

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  /35

  $695,000 Open Sat 12PM - 2PM

  • 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
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  /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
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  /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
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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
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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
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  /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
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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

  $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
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  /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
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  /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
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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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  /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
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  /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 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
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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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  /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
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  /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
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  /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
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  /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
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  /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
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  /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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  /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
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  /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
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  /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
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  /49

  $598,000

  • 4 Beds
  • 2 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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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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
• 

  

  /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
• 

  

  /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

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