Columbia County NY Homes under $500,000

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  /13

  $500,000

  • Land
  • 23.4 Acres
  • $21,368 per Acre

  191 - B Columbia Turnpike, Greenport, NY 12534

  Unusual opportunity to own your own 23.4 acres with a 12+ acre lake! Clay Pond Farms is a centrally located, easily accessible property that blends endless business and recreation opportunities. Just minutes from downtown HUDSON, NY, this unusual property offers a prime opportunity for investors, developers, recreational and sports enthusiasts, or anyone with an outdoorsy vision. Perhaps an In

  

  Paul Barrett

  Houlihan Lawrence Inc.

  (518) 318-9506

  191 - B Columbia Turnpike, Greenport, NY 12534
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  /24

  $475,000

  • 4 Beds
  • 1 Bath
  • 1,488 Sq Ft

  131 Route 82, Hudson, NY 12534

  Welcome to your new home! This 4 bedroom, 1 bath ranch in Hudson offers comfort and convenience with a spacious lot, low taxes and a peaceful back deck- perfect for relaxing or entertaining. Enjoy a full basement for storage or hobbies, all while close to shopping, dining and all the Hudson Valley has to offer! This beautiful 1.4 acre lot includes pear, apple, cherry trees and many perennials.

  Amy Morgan KW Platform

  131 Route 82, Hudson, NY 12534
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  /24

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,540 Sq Ft

  218 Decker Rd, Craryville, NY 12521

  Sited just 10 mins from Hudson's Warren St. historic district this modern open floor plan ranch home offers everything one could want! The house features 3 bedrooms, primary w/en-suite bath and walk-in closet, 2 full baths, living room (w/gas fireplace), dining room & modern gourmet kitchen with granite counter tops and stainless steel appliances. The house has central AC, a generator, alarm

  Martin Salerno The Kinderhook Group, Inc.

  218 Decker Rd, Craryville, NY 12521
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  /24

  $499,000

  • 4 Beds
  • 3 Baths
  • 1,804 Sq Ft

  198 County Route 10, Germantown, NY 12526

  Location - Land - Multiple Bedrooms - ADU - Storage! This home has it all and is just waiting for you to shine it up!Located on a beautiful county road, where the Catskills peek at you on your way home, you'll find this 1952 split level Ranch with an ADU.The main floor the home has a rear facing kitchen/dinette with real wood cabinets that overlooks the back yard, 2 car garage

  Beth Harring Harring Properties, LLC

  198 County Route 10, Germantown, NY 12526
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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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  /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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  /31

  $495,000

  • 2 Beds
  • 2 Baths
  • 1,832 Sq Ft

  117 Spring St, Craryville, NY 12521

  A Modern Retreat with Rustic Charm at the End of a Quiet Road.Nestled at the very end of a peaceful country road, this contemporary home with rustic flair offers the perfect blend of modern comfort and natural warmth. Privately set and surrounded by nature, this home is a tranquil haven ideal for year-round living or a weekend getaway.Step inside to discover thoughtfully crafted

  Maria DiSalvo Coldwell Banker Prime

  117 Spring St, Craryville, NY 12521
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  /36

  $499,900

  • 4 Beds
  • 2 Baths
  • 2,280 Sq Ft

  854 Columbia St, Hudson, NY 12534

  This charming Two-Unit Property in the Heart of Hudson is a versatile gem that awaits you!Welcome to your next investment opportunity or the perfect single-family home! Nestled in the vibrant city of Hudson, this delightful two-unit property offers a unique blend of comfort, convenience, and potential. With both units featuring a spacious living room, large dining room for entertaining,

  Barbara Robinson Red Apple Realty

  854 Columbia St, Hudson, NY 12534
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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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  /33

  $479,000

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  4 Tanners Ln, Hudson, NY 12534

  A true hidden gem in downtown Hudson is available for the first time in over 40 years. This cozy 3 bed, 1 bath home is located at the end of a dead-end lane within walking distance of the Amtrak Station, Basilica, and the Hudson Riverfront. Enjoy your own little private oasis while being close to everything the city of Hudson has to offer. This property is a diamond in the rough with endless

  Savannah Delaney Weichert Realtors Fontaine

  4 Tanners Ln, Hudson, NY 12534
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  /20

  $479,000

  • 2 Beds
  • 1 Bath
  • 770 Sq Ft

  13 Tremper Property Assn Rd, Canaan, NY 12029

  Vintage 1920 Queechy Lake cottage with deeded right of way to the lake shore. Enjoy complete privacy here at your 4-season getaway. Magical tree-house setting on one full acre with cozy front porch. Turn-key property with hardwood floors, great room with cathedral ceiling, kitchen with dishwasher and washer & dryer, two bedrooms, one bath. Room to expand. A sweet shed for your kayak and bike. A

  Nancy Cuddihy STONE HOUSE PROPERTIES, LLC

  13 Tremper Property Assn Rd, Canaan, NY 12029
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  /47

  $479,900

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  88 County Route 26a, Stuyvesant, NY 12173

  Charming, well-maintained ranch-style home in peaceful Stuyvesant! Offers 3 bedrooms and 2.5 baths on the main floor, plus 2 additional potential bedrooms with full egress windows and an office space in the partially finished basement. Enjoy a bright, open layout, ample storage, and a spacious yard. Includes electric car charging station, on-demand generator, and radon mitigation

  Dayton King KW Platform

  88 County Route 26a, Stuyvesant, NY 12173
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  /42

  $475,000 Open Sun 1PM - 3PM

  • 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
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  /44

  $485,000

  • 2 Beds
  • 1 Bath
  • 1,124 Sq Ft

  390 County Route 22, Hudson, NY 12534

  Conveniently located just 10 minutes from the shop restaurants, and Antique Boutiques of Warren Street.''Nestled in the picturesque Hudson Ny! 390 County Route 22 in Hudson Ny, offers a tranquil retreat with stunning views and your very own In-Ground Pool. This charming property is set on a spacious, well-maintained lot , providing privacy and the perfect escape from the hustle and

  Manga Mwazi Corcoran Country Living

  390 County Route 22, Hudson, NY 12534
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  /25

  $425,000

  • 1 Bed
  • 1 Bath
  • 1,100 Sq Ft

  220 W Pond Lily Rd, Elizaville, NY 12523

  Charming Hudson Valley Weekender — Affordable, Easy, and Full of Character!Once one of Gallatin’s original schoolhouses, this unique property is rich with history and creative energy. Thoughtfully maintained by a scholar and artist, it features an open floor plan with exposed beams, skylights, and beautifully preserved woodwork, all filled with natural light.An airy sleeping loft

  Margaret Niekrewicz Margaret Mondello Real Estate

  220 W Pond Lily Rd, Elizaville, NY 12523
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  /33

  $445,000

  • 3 Beds
  • 2 Baths
  • 1,258 Sq Ft

  8 Hover Rd, Claverack, NY 12513

  Welcome home to this beautifully renovated mid-century ranch, perfectly situated on a generous 0.35-acre corner lot. This stunning residence seamlessly blends classic charm with modern comfort, providing an idyllic retreat for today's lifestyle.Step inside to discover a completely transformed interior featuring brand new siding, stylish flooring, and a state-of-the-art heating and air

  Barbara Robinson Red Apple Realty

  8 Hover Rd, Claverack, NY 12513
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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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  /29

  $449,000

  • 4 Beds
  • 4 Baths
  • 2,112 Sq Ft

  316 State St, Hudson, NY 12534

  This Hudson gem is set on the bustling 300 block of State St with new townhouse construction and remodels all around! 316 State is a charming 3-unit, semi-attached rental building that offers many options to the buyer/investor. The building currently has 2, 1-bedroom apartments and 1, 2-bedroom apartment. Live in one unit and rent out the other 2 or remodel into a stylish townhouse with many of

  Alan Weaver Alan Weaver, Lic. RE Broker

  316 State St, Hudson, NY 12534
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  /4

  $499,000

  • 8 Beds
  • 4 Baths
  • 2,700 Sq Ft

  7 S 7th St, Hudson, NY 12534

  Prime redevelopment opportunity in the heart of Hudson!! This vacant 4-unit building is located in the Central Commercial District, allowing for a wide range of uses including retail, office, hospitality, or residential. This structure will need extensive work and you should consult your own engineer. Situated at the corner of South 7th Street and Cherry Alley—just steps from Warren

  Elizabeth Hendler Berkshire Hathaway HomeService

  7 S 7th St, Hudson, NY 12534
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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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  /32

  $418,000

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  18 McGrath Hill Rd, East Chatham, NY 12060

  OPEN HOUSE SUNDAY AUGUST 31, 11 AM TO 1 PM Easy country living in a private setting and all on one level. Move in and enjoy on day one this 2003 built home with 3 bedrooms, 2 and 1/2 baths. The sun filled 2.3 acres provides privacy and room for the garden enthusiast, animals and a the front porch is perfect for relaxing and viewing the picturesque country property. (Currently, there are

  Peter Newman Beach & Bartolo Realtors

  18 McGrath Hill Rd, East Chatham, NY 12060
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  /24

  $425,000

  • 3 Beds
  • 1 Bath
  • 1,422 Sq Ft

  7 Knickerbocker Ave, Hudson, NY 12534

  🏡 A Peace of Hudson - Modern Home with Airbnb Setup & Expansion Potential!This fully updated 1,293 sq. ft. two-level home in Hudson blends modern comfort with flexibility and income potential. The main level features sleek finishes, all newer appliances, and a smart layout with 3 bedrooms and a full bath all on the first floor. Interior access leads to a clean, dry

  Elizabeth Hendler Berkshire Hathaway HomeService

  7 Knickerbocker Ave, Hudson, NY 12534
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  /45

  $434,000

  • 5 Beds
  • 3 Baths
  • 2,740 Sq Ft

  4269 State Route 203, North Chatham, NY 12132

  Step back in time with this charming Queen Anne-style Victorian home, built in 1904. The home features many original details, moldings, and hardware. The first floor offers a kitchen with a butler's pantry, an oversized den with a built-in daybed in the window, a dining room, a living room with a fireplace, and a first-floor bedroom that could also serve as an office. Additionally, there are two

  Kari Van Buren Berkshire Hathaway HomeService

  4269 State Route 203, North Chatham, NY 12132
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  /28

  $499,000

  • 4 Beds
  • 2 Baths
  • 2,142 Sq Ft

  95 Albany Ave, Kinderhook, NY 12106

  UPDATE! New carpet installed last month, floors have been refinished, and many rooms have been freshly repainted. Welcome to this bright and beautifully updated split-level ranch, nestled in the charming Village of Kinderhook. The main level offers an open-concept layout that seamlessly connects the kitchen, dining, and living areas—perfect for entertaining or everyday living. Enjoy the

  Beau Piorkowski Empire Real Estate Firm LLC

  95 Albany Ave, Kinderhook, NY 12106
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  /36

  $499,900

  • 3 Beds
  • 2 Baths
  • 1,803 Sq Ft

  55-59 Fairview Ave, Hudson, NY 12534

  Welcome to this beautifully fully renovated 3-bedroom, 2-bath ranch in the heart of Hudson, NY! Just a short stroll to Warren Street, this home offers a tastefully updated aesthetic and one-floor living. Other key features include a timeless functional layout, LVP flooring throughout, a STUNNING modern kitchen, and freshly updated bathrooms. It is truly move-in ready! Step outside to a spacious

  Emma Schaeffer Empire Real Estate Firm LLC

  55-59 Fairview Ave, Hudson, NY 12534
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  /22

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,323 Sq Ft

  15 Birch Rd, Copake, NY 12516

  Welcome to this 3 BR, 2 BA home sited on .45 acre at Taconic Shores. Near to Beach 3 on Robinson Pond (the natural part of the lake). With updated kitchen, bathrooms and a fresh coat of paint, this home is ready for its' next owner. These sellers have enjoyed campfires and BBQ's in the back yard, after a swim in the lake. Taconic Shores is a private lake community and surrounds

  Theresa Westlake Copake Lake Realty Corp.

  15 Birch Rd, Copake, NY 12516
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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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  /41

  $499,900

  • 3 Beds
  • 1 Bath
  • 1,133 Sq Ft

  135 Millbrook Rd, Hudson, NY 12534

  Nestled on 6.67 secluded acres, this charming 1935 Cape Cod home offers a perfect blend of privacy and nature! Wake up to the stunning vistas of the Catskill Mountains, where nature's beauty surrounds you, creating a tranquil retreat away from the hustle and bustle of everyday life.As you step inside, you'll be greeted by a warm and inviting living room featuring a cozy fireplace with a

  Barbara Robinson Red Apple Realty

  135 Millbrook Rd, Hudson, NY 12534
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  /35

  $499,000

  • Land
  • 50 Acres
  • $9,980 per Acre

  00 Mambert Rd, Livingston, NY 12534

  Discover your own 50-acre sanctuary in the Hudson Valley, a landscape of rolling meadows, a peaceful pond, a winding stream, and two timeless period barns that set the stage for a truly picturesque retreat. With nearly 4,000 feet of road frontage, this expansive property offers unmatched privacy while still placing you just minutes from the cultural and culinary treasures of Hudson, Catskill, and

  Michael Tellerday Houlihan Lawrence, Inc.

  00 Mambert Rd, Livingston, NY 12534
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  /17

  $499,900

  • 3 Beds
  • 2 Baths
  • 1,972 Sq Ft

  1626 Route 9, Tivoli, NY 12583

  Discover peaceful living just minutes from Red Hook and Hudson in this warm and welcoming 3-bedroom*, 2-bath* country home. Nestled on a private lot with its own pond, this property blends modern comfort with timeless charm. Inside, you'll find sun-filled rooms, gleaming hardwood floors, and a cozy, inviting atmosphere. A brand-new heat pump and central air keep you comfortable year-round,

  Lindsay Schultz JFIVE HOMES REALTY LLC

  1626 Route 9, Tivoli, NY 12583
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  /9

  $449,000

  • Land
  • 11.65 Acres
  • $38,541 per Acre

  0 County Route 7 Unit 20252252, Ancram, NY 12502

  Build your dream estate on 11.65 private acres in the heart of Ancram, NY—one of Columbia County's most sought-after locations. This prime Hudson Valley homesite sits at the end of a quiet, shared drive and includes a professionally installed driveway and Board of Health approval, offering a seamless start to your vision.Enjoy sweeping views of rolling farmland and the distant Taconic

  John Panzer Elyse Harney Real Estate

  0 County Route 7 Unit 20252252, Ancram, NY 12502
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  /9

  $449,000

  • Land
  • 11.15 Acres
  • $40,269 per Acre

  0 County Route 7 Unit 20252251, Ancram, NY 12502

  Build your dream estate on 11.15 private acres in the heart of Ancram, NY—one of Columbia County's most sought-after locations. This prime Hudson Valley homesite sits at the end of a quiet, shared drive and includes a professionally installed driveway and Board of Health approval, offering a seamless start to your vision.Enjoy sweeping views of rolling farmland and the distant Taconic

  John Panzer Elyse Harney Real Estate

  0 County Route 7 Unit 20252251, Ancram, NY 12502
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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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  /27

  $419,000

  • 3 Beds
  • 3 Baths
  • 1,460 Sq Ft

  33 Dermody Rd, Canaan, NY 12029

  How about some privacy! This three bedroom, three bath home has lots of privacy and elbow room to play and relax. There is a cathedral ceiling flooding light into the kitchen. A country setting tucked away yet close the Berkshires, Tanglewood, skiing and all the culture this area has to offer. A Finished lower level adds great space for movie watching or quiet contemplation as well as a 12ft by

  Ryan Lane Gilcrest Properties

  33 Dermody Rd, Canaan, NY 12029
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  /50

  $400,000

  • 5 Beds
  • 3 Baths
  • 2,496 Sq Ft

  20 Shore Dr, Elizaville, NY 12523

  Imagine waking up to the gentle sounds of lake life, stepping out onto your expansive corner lot where morning coffee tastes better surrounded by the promise of mature gardens waiting to bloom again. This 5-bedroom, 3-bathroom ranch estate sits on TWO SEPARATE PARCELS in the coveted Twin Lakes community, offering savvy investors and visionary developers a rare opportunity to resurrect a

  Michele Marina Atlantica East Associates LLC

  20 Shore Dr, Elizaville, NY 12523
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  /19

  $485,000

  • Land
  • 60.13 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
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  /16

  $485,000

  • Land
  • 60.13 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
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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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  /17

  $499,000

  • Land
  • 83.22 Acres
  • $5,996 per Acre

  50 - 61 Dugway Rd, Hillsdale, NY 12529

  Two Large Parcels Combine Offering Serenity & Great Potential. Located between the charming towns of Chatham, NY, and Great Barrington, MA, this 83 acre parcel offers you exceptional potential awaiting your vision, and ideal escape.Two adjoining proprieties come together to form this large property that is a unique blend of privacy and accessibility. Enjoy impressive road frontage on two roads

  Jeffrey McKinney Beach & Bartolo Realtors

  50 - 61 Dugway Rd, Hillsdale, NY 12529
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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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