5-Bedroom Homes for Sale in Columbia County NY

• 

  

  

  /99

  $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
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  /18

  $395,000

  • 6 Beds
  • 2.5 Baths
  • 4,000 Sq Ft

  3630 Mechanic St, Valatie, NY 12184

  Large farmhouse on one of Valatie's largest village lots of 1.11 A. 4000+ sq ft country home with 6 bedrooms and 2.5 baths. Large meandering rooms suitable for a large extended family or make apartments. There are two large enclosed porches (one with a woodstove) plus a covered outdoor summer patio. Also on the property is a 1000 square foot outbuilding suitable for a studio or workshop. Many

  

  William Laraway

  Val Kin Properties, LLC

  (518) 873-4404

  3630 Mechanic St, Valatie, NY 12184
• 

  

  

  /89

  $3,900,000

  • 5 Beds
  • 6 Baths
  • 4,532 Sq Ft

  520 Ridge Rd, Schodack Landing, NY 12156

  Nestled in the breathtaking Hudson Valley, where rolling hills, lush forests, and sparkling waterways create a picturesque backdrop, this extraordinary 481 acre property offers the perfect balance of outdoor adventure and serene escape. Whether you're seeking a weekend retreat or a permanent residence, this estate presents a unique blend of seclusion, convenience, and boundless possibilities.Step

  

  April Seney

  Core Real Estate Team

  (518) 676-2597

  520 Ridge Rd, Schodack Landing, NY 12156
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  /44

  $1,100,000

  • 6 Beds
  • 6 Baths
  • 5,660 Sq Ft

  77 N 5th St, Hudson, NY 12534

  Fantastic Investment opportunity in upper Hudson, NY! This 5 unit apt bldg has off street parking, and all units have separate utilities. Upgraded in the past 10 yrs include: new heating, a/c,electric, windows and more. Perfect opportunity for an owner occupant unit and have tenants help pay your mortgage, or keep as an investment. Building is centrally located to all that Hudson has to offer,

  

  Patricia Meyers

  Lake and Mountain Realty, LLC

  (518) 539-4775

  77 N 5th St, Hudson, NY 12534
• 

  

  

  /99

  $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
• 

  

  /48

  $1,900,000

  • 7 Beds
  • 3.5 Baths
  • 2,052 Sq Ft

  48 County Route 14 None, Hudson, NY 12534

  Equestrian Hideaway! Welcome to Long View Farm & Stables, a private stable and farm compound just minutes from downtown Hudson, NY and an easy trailer to riding venues in Saratoga and the Berkshires. Nestled away on 24-bucolic acres are rolling pastures with long distant views of the Catskill Mountains, the neighboring Hudson Valley apple and stone fruit orchards and an overlook of two swim

  

  Paul Barrett

  Houlihan Lawrence Inc.

  (518) 600-3409

  48 County Route 14 None, Hudson, NY 12534
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  /104

  $799,000

  • 9 Beds
  • 6 Baths
  • 4,851 Sq Ft

  198 Richmond Rd, Valatie, NY 12184

  Welcome to your dream retreat! This incredible compound offers 9 bedrooms, 6 bathrooms, and nearly 10 acres of pure serenity. The stunning great room is the showstopper—surrounded by windows and boasting a massive open floor plan. Enjoy a chef's kitchen with island, bar stool seating and stainless steel appliances. Enjoy beautiful stone fireplace and wood stoves to keep you and guests nice and

  Kevin Clancy Clancy Real Estate

  198 Richmond Rd, Valatie, NY 12184
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  /45

  $2,550,000

  • 5 Beds
  • 4.5 Baths
  • 3,750 Sq Ft

  0 Schnackenberg Rd, Ghent, NY 12075

  An incredible compound on 47 acres on rolling green hillsides on a beautiful road just minutes to Hudson. Spectacular west facing views make for incredible sunsets over the Catskill Mountains, and a fabulous swimming pond to cool off on a hot summer’s day. The early Dutch farmhouse is set nicely back from the quiet road, a row of privet has been planted for complete privacy. The 2,400 square foot

  Annabel Taylor Four Seasons Sothebys Intl

  0 Schnackenberg Rd, Ghent, NY 12075
• 

  

  /59

  $2,500,000

  • 5 Beds
  • 5.5 Baths
  • 4,645 Sq Ft

  42 Golf Course Rd, Craryville, NY 12521

  A striking modern lake home offering the perfect blend of privacy and community, designed by acclaimed New York architect Gray Davis. Tucked away on a beautifully landscaped, fully fenced property, this home is a hidden sanctuary—yet just beyond the gates, you'll find the region's only high-speed motorboat lake and an award-winning golf course. A study in indoor/outdoor living, the walls of

  John Barbato Compass, Hillsdale

  42 Golf Course Rd, Craryville, NY 12521
• 

  

  /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
• 

  

  /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
• 

  

  /40

  $1,500,000

  • 5 Beds
  • 4 Baths
  • 4,512 Sq Ft

  226 County Route 17, Valatie, NY 12184

  Welcome to historic Surdeval Farm, a spacious 4,500 square-foot, five-bedroom, four-bath homestead on 24.5 acres located between the charming villages of Chatham, Kinderhook, and Valatie. Over the decades the original early 1800’s core home was expanded and rearranged. Now the formal entrance to the home is from the grand tree-lined circular driveway to the side door, to a foyer, which opens to a

  Peggy Lampman Peggy Lampman

  226 County Route 17, Valatie, NY 12184
• 

  

  /43

  $1,350,000

  • 17 Beds
  • 17 Baths
  • 12,984 Sq Ft

  437 Snydertown Rd, Craryville, NY 12521

  437 Snydertown Road is a property designed for those who value space, seclusion, and style without compromising convenience. Just 15 minutes from Hudson's Amtrak station and under two hours from Manhattan by car, this rare Columbia County estate combines the timeless character of an 1820s Greek Revival with an unmatched secluded family compound right behind you. .The 2,588 sq. ft.

  Daniel Mahar Mahar Real Estate, LLC

  437 Snydertown Rd, Craryville, NY 12521
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  /61

  $2,995,000

  • 5 Beds
  • 4.5 Baths
  • 2,400 Sq Ft

  361 Schnackenberg Rd, Ghent, NY 12075

  An incredible 188 acre property on a highly desirable rural road in the heart of the rolling farmlands of Columbia County. Spectacular west facing views make for incredible sunsets over the Catskill Mountains, the Hudson Valley spreads out beneath them. The acreage includes pastoral farm fields, largely maintained by the neighboring biodynamic farm, forest, and a beautiful swimming pond to cool

  Annabel Taylor Four Seasons Sotheby's Int.

  361 Schnackenberg Rd, Ghent, NY 12075
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  /103

  $2,295,000

  • 5 Beds
  • 4.5 Baths
  • 4,484 Sq Ft

  1114 County Route 3, Ancram, NY 12502

  Welcome to Iris Valley Estatea€''a palatial, contemporary estate set on 24 acres with sweeping views of the Berkshire Mountains, thoughtfully designed for year-round living, gathering, and creative pursuits. At its center is a spacious three-level main house featuring an open-concept kitchen, breezeway-connected bedroom wings, a heated gunite pool, and outdoor entertaining areas. A modern guest

  Anthony D'Argenzio Houlihan Lawrence

  1114 County Route 3, Ancram, NY 12502
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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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  /40

  $1,600,000

  • 18 Beds
  • 12 Baths
  • 344,124 Sq Ft

  7951 New York 22, Copake Falls, NY 12517

  This might be one of the most exciting opportunities available in Columbia County right now! Zoned both Commercial and Residential, most recently run as Newman Residence Adult Camp &previously known as 'The Rockledge Motel' on just under 16 acres. Mature landscaping and unique stone walls with 1,130 feet of road frontage on Route 22. Original building Cira 1900, added on (20x20 sq. ft additional

  Margaret Bower Avenia Columbia County RE Specialist

  7951 New York 22, Copake Falls, NY 12517
• 

  

  /69

  $1,590,000

  • 7 Beds
  • 5.5 Baths
  • 7,316 Sq Ft

  126 Shaker Ridge Dr, Canaan, NY 12029

  Berkshire/New York Contemporary Estate CHECK OUT VIRTUAL TOURS #2, & #3. 4616 sf Main Home (3100 + 1516 +storage) + 2700sf Guest Residence on 20 private acres (3 lots) in Shaker Ridge. Soaring spaces and beautiful stone fireplaces, master suite w. fireplace, plus junior suite and third BR or studio with sink. Large kitchen with informal dining area & lounge with fireplace, plus, great room with

  David Birch Barns & Farms Realty, LLC

  126 Shaker Ridge Dr, Canaan, NY 12029
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  /32

  $200,000

  • 7 Beds
  • 2 Baths
  • 2,300 Sq Ft

  682 New York 217, Hudson, NY 12534

  Your Perfect Investment Awaits!Welcome to your next real estate opportunity! This two-family income property offers the perfect blend of affordable living and investment potential. Whether you're looking to reside in one unit while generating rental income from the other or seeking a multi-generational living arrangement, this property has it all!Property Highlights include

  Barbara Robinson Red Apple Realty

  682 New York 217, Hudson, NY 12534
• 

  

  /30

  $1,795,000

  • 5 Beds
  • 4 Baths
  • 3,280 Sq Ft

  320 Allen St, Hudson, NY 12534

  The John C. Dubois House - Historic 1870 Italianate Brick Brownstone Step into history with this stately brick Brownstone, majestically positioned on one of Hudson's most prestigious tree-lined blocks. The John C. Dubois House, built in 1870, exemplifies the grandeur of Italianate-era architecture while offering modern luxury throughout its thoughtfully restored interiors. This

  Chris Getman Houlihan Lawrence Inc.

  320 Allen St, Hudson, NY 12534
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  /36

  $259,000

  • 6 Beds
  • 2.5 Baths
  • 2,664 Sq Ft

  41 Prospect St, Philmont, NY 12565

  Welcome into possibility with this 1900 duplex in the Village of Philmont — a property with history, updates, and so much potential. Spanning 2,664 sq ft, both apartments offer 3 bedrooms each, with Apartment B featuring 1.5 baths.While it invites your creative touch, key improvements are already in place:All brand-new windows throughout the building bring in light and

  Heather Davala Davala Real Estate

  41 Prospect St, Philmont, NY 12565
• 

  

  /55

  $1,150,000

  • 6 Beds
  • 4 Baths
  • 3,930 Sq Ft

  455 Post Hill Rd, Craryville, NY 12521

  An Historic, Solar-Powered home on 11 Private Acres in the Hudson Valley.Set on a quiet hilltop at the end of a long drive, this private property offers timeless craftsmanship, modern comfort, and a rare sense of seclusion — all within two hours of New York City.Originally an 1880s Pennsylvania barn, the main house was meticulously dismantled and reassembled beam by beam, blending

  John Barbato Compass, Hillsdale

  455 Post Hill Rd, Craryville, NY 12521
• 

  

  /39

  $895,000

  • 5 Beds
  • 3.5 Baths
  • 2,834 Sq Ft

  11 Cold Water St, Hillsdale, NY 12529

  This handsome Greek Revival sits on a quiet street occupying a generous village lot in the historic Hamlet of Hillsdale. Built around 1848, the home feels historic and fresh with plenty of room to spread out. A wide front porch with Doric columns welcomes you inside to a central foyer. To one side, a front parlor opens to a spacious dining room with elegant moldings. The kitchen is a highlight,

  MATTHEW CAREY Rouse + Co Real Estate, LLC

  11 Cold Water St, Hillsdale, NY 12529
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  /35

  $699,900

  • 12 Beds
  • 4 Baths
  • 4,032 Sq Ft

  59 Dodge St, Hudson, NY 12534

  Welcome to your next investment opportunity to own this 4 family house on Dodge Street in City of Hudson, the place to live! We have great music, Antiques, renowned art galleries and elegant restaurants. These key industries have made Hudson the third busiest train destination in the north east corridor for the Amtrak. In the heart of Hudson is 59 Dodge Street, a real charming 4 family building

  Jahorul Liton Red Apple Realty

  59 Dodge St, Hudson, NY 12534
• 

  

  /33

  $549,000

  • 7 Beds
  • 3 Baths
  • 2,684 Sq Ft

  214 Robinson St, Hudson, NY 12534

  Robinson Street is a tucked away haven in downtown Hudson and 214 Robinson is the big kid on the block. A unique, 3-story apartment building, 214 has 3 full-floor apartments. The first floor has a 2 bedroom, one bath unit with living room and an eat-in kitchen. The second floor was recently remodeled into a 2 bedroom, 3/4 bath unit with living room and eat-in kitchen. The top floor unit has 3

  Alan Weaver Alan Weaver, Lic. RE Broker

  214 Robinson St, Hudson, NY 12534
• 

  

  /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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  /5

  $310,000

  • 5 Beds
  • 2 Baths
  • 2,350 Sq Ft

  225 1/2 Columbia St, Hudson, NY 12534

  Fantastic investment or starter opportunity in the heart of Hudson! This two-family home sits on a double lot offering endless possibilities. Each spacious apartment is approximately 1,200 sq ft, perfect for owner-occupants to live in one unit and have rental income to cover expenses. There is an additional structure next to the 2 family. This was a former neighborhood store. Both buildings need

  Elizabeth Hendler Berkshire Hathaway HomeService

  225 1/2 Columbia St, Hudson, NY 12534
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  /51

  $638,900

  • 5 Beds
  • 2.5 Baths
  • 2,268 Sq Ft

  61 Park Place N, Valatie, NY 12184

  Tucked away on 2.5 wooded acres, this spacious tri-level chalet offers 5 bedrooms, 2.5 baths, and sweeping views of the surrounding pines. Beautifully updated and move-in ready, the home features a brand new kitchen, finished lower level, newer windows, newer doors, and fresh interior paint. The contemporary design with a modern, airy feel opens to a generous family/media room on the lower

  Kathryn Kole Coldwell Banker Prime Properti

  61 Park Place N, Valatie, NY 12184
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  /74

  $1,385,000

  • 8 Beds
  • 5 Baths
  • 4,854 Sq Ft

  16 Hudson St, Kinderhook, NY 12106

  Introducing The Kinderhook Guild, a beautifully restored circa 1787 Federal-style landmark in Kinderhook's vibrant village center offering 10 flexible units and a parking lot with room for 17 cars. Original wide-plank floors, hand-hewn beams, Rumford fireplaces, and wavy-glass windows have been preserved, with upgrades including a commercial-grade kitchen and ADA-compliant restroom. The ground

  Anthony D'Argenzio Houlihan Lawrence

  16 Hudson St, Kinderhook, NY 12106
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  /45

  $449,000 Open Sun 11AM - 1PM

  • 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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  /46

  $975,000

  • 5 Beds
  • 3.5 Baths
  • 2,622 Sq Ft

  823 Warren St, Hudson, NY 12534

  Exceptional opportunity to own a fully vacant, three-unit multi-family property in the heart of Hudson's vibrant Warren Street. This charming building offers a unique blend of investment potential and personal use, with a proven track record as a successful short-term rental and owner use property. Featuring three distinct units, this property is ideal for investors, or live in owners. Prime

  Austin Urban Copake Lake Realty Corp.

  823 Warren St, Hudson, NY 12534
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  /66

  $1,695,000

  • 5 Beds
  • 5 Baths
  • 7,290 Sq Ft

  45-49 8th St, Hudson, NY 12534

  This six-unit mixed-use building, located one block from Warren Street, is an absolute must see property for anyone interested in investing in Hudson, NY. Home of Cafe Mutton, twice recognized by the James Beard Awards, and by Bon Appetit magazine, this beautiful building boasts a yearly pro forma gross rent of 159,000 dollars, against yearly pro forma carrying charges (taxes, insurance, water &

  William Jackson Anderson Agency

  45-49 8th St, Hudson, NY 12534
• 

  

  /31

  $1,400,000

  • 14 Beds
  • 7 Baths
  • 6,490 Sq Ft

  6045 New York 9g, Hudson, NY 12534

  Incredible opportunity for serious investors! 7 residential units- all NEWLY RENOVATED! Totally vacant for the new buyer to bring on his or her own tenants. 3 bay detached garage, 4 storage units on site, plus a workshop that is rented by a local contractor. All units except for 1 building have in-house washer/dryer. Pro-forma gross rents are 174,600 with annual expenses of 26,741 leaves a

  Michael Castellano Gilcrest Properties

  6045 New York 9g, Hudson, NY 12534
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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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  /42

  $635,000

  • 5 Beds
  • 4 Baths
  • 3,248 Sq Ft

  19 Lovers Ln, New Lebanon, NY 12125

  Large home with room for everyone! This 5 bed 4 bath (2 full, 2 half-both half baths are on the first floor) home features 2 full kitchens, 2 living rooms, and 2 dining rooms as it was once a 2 family home. Convert it back and have rental income, make it a seasonal rental, or just enjoy it the way it is. It's spacious, bright, has a beautiful wrap around rocking chair porch, two enclosed

  Melissa Dimassimo Stone House Properties, LLC

  19 Lovers Ln, New Lebanon, NY 12125
• 

  

  /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
• 

  

  /41

  $779,000

  • 5 Beds
  • 2.5 Baths
  • 2,860 Sq Ft

  1754 Harlemville Rd, Chatham, NY 12037

  5.79 acres in beautiful location w/privacy off secondary rd w/woods on all sides. Pond stocked w/lg mouth bass, landscaping, att one car garage, separate storage shed. Low maintenance Colonial style house w/brick & vinyl siding. Second floor en-suite primary on one end & three BRs + full bath on other end. Can be a five BR if needed. Revel in the tranquility of this 2,860 sq. ft. residence by the

  Frances Ingraham Heins Howard Hanna Capital Inc

  1754 Harlemville Rd, Chatham, NY 12037
• 

  

  /50

  $8,475,000

  • 6 Beds
  • 7.5 Baths
  • 12,418 Sq Ft

  367 Prospect Hill Rd, Ancramdale, NY 12503

  First time on the market! This magnificent 170-acre Modern Adirondack-styled estate near Millbrook, designed by architect Lloyd Taft, features a main house and three elegant guest cabins. Built by a third-generation builder of camps in upstate New York and the Thousand Islands, the cabin serves as the centerpiece of the compound. Meticulously maintained and tailor-made for year-round recreation,

  George Langa Houlihan Lawrence Inc.

  367 Prospect Hill Rd, Ancramdale, NY 12503
• 

  

  /64

  $4,500,000

  • 6 Beds
  • 4.5 Baths
  • 5,600 Sq Ft

  340 Northern Blvd, Germantown, NY 12526

  Nestled near the meeting point of the Hudson & Camp Creek on 3.5 splendidly landscaped acres, Peary Homestead is a well-preserved & abundantly charming example of the 19th-century Gothic Revival country manor. The current owners continued expanding the bountiful gardens, while also undertaking, with the help of architect Chip Bohl & interior designer Louise Copeland, a complete interior

  Raj Kumar Four Seasons Sotheby's International Realty

  340 Northern Blvd, Germantown, NY 12526
• 

  

  /18

  $345,000

  • 6 Beds
  • 4 Baths
  • 6,046 Sq Ft

  170 County Route 7a Unit 1, Copake, NY 12516

  BRING ALL OFFERS! Put A Fork in Us, We're Done!! It's time for the next chapter of the Copake Inn. With a long-standing history in the center of Copake -- ahh, if only the walls could talk, the stories that could be told.The Horse Shoe bar remains, along with room for dining tables, dancing and a pool table on the main floor. Living space on the upper level includes single rooms with a hallway

  Lindsay Lebrecht Copake Lake Realty Corp.

  170 County Route 7a Unit 1, Copake, NY 12516

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