Columbia, NY Homes

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  $480,000

  • 2 Beds
  • 1.5 Baths
  • 1,155 Sq Ft

  289 Tunnel Hill Rd, Canaan, NY 12029

  A historic schoolhouse has been converted into a dreamy country home in a picturesque corner of the region bordering both the Hudson Valley and the Berkshires. This half-acre property is full to the brim with flowers & garden beds, butterflies & birds. The home has been reimagined into a 2BD 2BA bungalow with a proper outdoor kitchen & patio, a three-season screened-in porch & detached,

  Annabel Taylor Four Seasons Sotheby's Int.

  289 Tunnel Hill Rd, Canaan, NY 12029
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  /14

  $3,900 per month

  • 3 Beds
  • 2.5 Baths
  • 2,012 Sq Ft
  • House for Rent

  136 Macedonia Rd, Chatham, NY 12037

  Your own Country Retreat! Beautiful Secluded Post and Beam home w/ large spring fed pond on 8 acres. Located only 10 minutes from the Village of Chatham. Open concept w/ rustic cozy feel with 3BR and 2 1/2 BA, large country kitchen, 2 family rooms, glass enclosed sun-room, field stone wood burning fireplace, pellet stove, laundry room with washer and dryer, first floor bedroom w/BA. Views of pond

  Elizabeth Hendler Berkshire Hathaway HomeService

  136 Macedonia Rd, Chatham, NY 12037
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  /13

  $82,000 Sold Jul 18, 2025

  • Land
  • 0.23 Acre
  • $356,522 per Acre

  • 30 Days On Market

  1258 Lakeview Rd, Copake, NY 12516

  A quarter acre of waterfront property ready to build your dream home. Board of Health approved for a 3br house. Public water. DEC approval in place for a dock, fire pit , shed, and shoreline and lot improvements. Current owners have preliminary plans to share for a home that awaits final design and permit submittal.The 110 acres of Robinson Pond is a thriving lake community with 2 community

  John Barbato Compass, Hillsdale

  1258 Lakeview Rd, Copake, NY 12516
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  Not Listed For Sale

  0 - A Fog Hill Rd, Austerlitz, NY 12017

  0 - A Fog Hill Rd, Austerlitz, NY 12017
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  /14

  $215,000

  • 2 Beds
  • 2 Baths
  • 1,426 Sq Ft

  763 New York 217, Hudson, NY 12534

  Discover the charm and potential of this 2-bedroom, 2-bath farmhouse in the heart of Philmont, NY. A true fixer-upper, yet perfectly livable, this home retains much of its original character, including wide-plank floors, detailed banister and railing trim, and vintage windows that bring warmth and history to each room. The spacious layout offers a rear porch for relaxing and enjoying the quiet

  Michael Castellano Gilcrest Properties

  763 New York 217, Hudson, NY 12534
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  /22

  $3,800 per month

  • 1 Bed
  • 1 Bath
  • 780 Sq Ft
  • Apartment for Rent

  238 Kelly Rd, East Chatham, NY 12060

  Looking for a short term rental??It doesn't get much better than this!!A stunning chalet type, bright, sun filled apartment with spectacular views over a detached garage. Includes one bedroom (Queen), Sleeper sofa in the living room,one large bath complete with Jacuzzi and Sauna. Fulling furnished kitchen dinette and living room all with an open floor plan with spectacular views of the Catskill

  Leonard Brown Berkshire Hathaway HomeService

  238 Kelly Rd, East Chatham, NY 12060
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  /36

  $400,000 Sold Jul 18, 2025

  • 3,182 Sq Ft
  • $126/SF
  • 111 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1972

  52 Bowman Rd, Chatham, NY 12037

  Discover this exceptional custom home nestled on 5.97 acres, complete with a serene ponda perfect blend of privacy and convenience. Located in Chatham, this property offers endless potential, whether you're seeking a private retreat or an investment opportunity. Currently configured as a two-unit, it can easily be transformed into a charming single-family residence. Since its purchase in 2020,

  Allison Rada Stone House Properties, LLC

  52 Bowman Rd, Chatham, NY 12037
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  /5

  Not Listed For Sale

  110 U S Highway 9, Hudson, NY 12534

  110 U S Highway 9, Hudson, NY 12534
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  /9

  $249,000

  • Land
  • 11 Acres
  • $22,133 per Acre

  36 Bacon Dr, Livingston, NY 12523

  A perfect spot to build your dream home or cabin nestled in the Gallatin / Livingston countryside. Meander down the 1200' long gravel driveway, past the newly erected storage building to your prepared build site. The hard work has been done with the driveway and septic for a 3 bedroom home in place. The well is in work so all that is left is to bring electric to the site and park your camper or

  Philip Feiner Country Life Real Estate, LLC

  36 Bacon Dr, Livingston, NY 12523
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  /10

  $2,800 per month

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • Townhouse for Rent

  516 State St Unit 518, Hudson, NY 12534

  Beautiful Hudson Rental!Three level townhouse: Living room and large eat-in-kitchen on the first level with two bedrooms and one bathroom on the second level. Additionally, there is a walkout lower level. In-unit washer/ dryer as well! This townhouse is conveniently located in the vibrant mid-city Armory neighborhood. Stroll to all amenities from this fantastic location! Only one half block to

  Debra Flack Compass Greater NY LLC

  516 State St Unit 518, Hudson, NY 12534
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  /22

  $299,900 Sold Jul 17, 2025

  • 898 Sq Ft
  • $334/SF
  • 25 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1955

  3 Storm Ave, Hudson, NY 12534

  Charming and manageable, this well-maintained home is perfect for buyers looking for a smaller space with great potential. Located on a quiet residential street in the city of Hudson, it's ideal as a full-time residence, weekend retreat, or rental.The main level features two bedrooms and a full bath with a walk-in shower. Downstairs, the finished lower level includes a spacious bed room,

  Elizabeth Hendler Berkshire Hathaway HomeService

  3 Storm Ave, Hudson, NY 12534
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  /4

  Not Listed For Sale

  97 - Approx # Farm Rd, Copake, NY 12516

  97 - Approx # Farm Rd, Copake, NY 12516
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  /28

  $349,900

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft

  532 County Route 32, Kinderhook, NY 12184

  Welcome to 532 County Route 32 in charming North Chatham, where this adorable 3 bedroom home is set on 1.49 picturesque acres with tall pines, a serene pond, and plenty of privacy. This inviting property combines comfort, character, and functionality, making it the perfect full-time residence, weekend escape, or investment.The home features beautiful ash floors, warm cedar siding, and a

  Michael Castellano Gilcrest Properties

  532 County Route 32, Kinderhook, NY 12184
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  /12

  $3,500 per month

  • 2 Beds
  • 1 Bath
  • 1,300 Sq Ft
  • Apartment for Rent

  407 Warren St Unit 2, Hudson, NY 12534

  One of the most grand apartments in all of downtown Hudson, this full-floor space is set in the heart of Warren street. Steps to Opera House, amazing shopping & world class restaurants. The apartment has 12 foot ceilings, parquet floors & original pocket doors creating multiple airy rooms, each w a stunning ornamental fireplace. Nice sunny kitchen, Washer/Dryer. The tall ceilings make great

  Robert Huston Tri Hudson Realty, LLC

  407 Warren St Unit 2, Hudson, NY 12534
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  /16

  $430,000 Sold Jul 17, 2025

  • 1,576 Sq Ft
  • $273/SF
  • 53 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1963

  27 Upper Cady Rd, Old Chatham, NY 12136

  You know what they say about brick houses, "they're mighty, mighty"Super sweet location for this privately situated country home in horse country. Ez one story living with updated kitchen and baths. The gathering rooms are open to each other and the living room offers a brick fireplace. There is a full bath off the hall and a half bath off the primary bedroom.Bring the horses, goats or chickens

  Linnea VanTassel Country Life Real Estate, LLC

  27 Upper Cady Rd, Old Chatham, NY 12136
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  /12

  Not Listed For Sale

  169 Old Shaker Rd, New Lebanon, NY 12125

  169 Old Shaker Rd, New Lebanon, NY 12125
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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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  /36

  $7,000 per month

  • 2 Beds
  • 1.5 Baths
  • 4,200 Sq Ft
  • House for Rent

  1370 Route 9, Tivoli, NY 12583

  Updated and charming expansive Tivoli gem. Perfect for students or family that needs space to spread out. First floor features a large open living room and dining room, a closed door office, large eat in kitchen with loads of storage, and the lounge room featuring a full bar and pool table for entertaining or spending evening in together. Half bathroom on this floor for convenience. Upstairs

  Chelsea Pollard-Seiler Mondello Upstate Properties

  1370 Route 9, Tivoli, NY 12583
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  $450,000 Sold Jul 17, 2025

  • 2,200 Sq Ft
  • $205/SF
  • 43 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1850

  239 Pleasantvale Rd, Tivoli, NY 12583

  Escape to a simpler time with this charming 1850's country farmhouse nestled on 4 acres of picturesque land. This home offers the perfect blend of old-world charm with modern conveniences. The expansive grounds offer endless possibilities for gardening, entertaining, or simply enjoying the beauty of nature. A large outbuilding is perfectly suited as an art studio or hobby room. You will love

  Geraldine Brucale BHHS Hudson Valley Properties

  239 Pleasantvale Rd, Tivoli, NY 12583
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  /8

  Not Listed For Sale

  93 - 94 Honor Rd, Livingston, NY 12523

  93 - 94 Honor Rd, Livingston, NY 12523
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  /35

  $2,250,000

  • 5 Beds
  • 3.5 Baths
  • 3,113 Sq Ft

  480 Taghkanic Churchtown Rd, Craryville, NY 12521

  A classic c1790 Colonial farmhouse, guest house and barns on forty gorgeous acres of rolling hillsides and pasture. Swim in the pond, pick vegetables from the garden, walk the trails. Just ten minutes to Hudson proper, you are right in the heart of the action but feel a world away on this pastoral property. The 3BD 2.5BA farmhouse has kept its best original details in tact, like the wideboard

  Annabel Taylor Four Seasons Sothebys Intl

  480 Taghkanic Churchtown Rd, Craryville, NY 12521
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  /45

  $7,700 per month

  • 9 Beds
  • 5 Baths
  • 12,000 Sq Ft
  • House for Rent

  147 Rock City Rd, Old Chatham, NY 12136

  Escape the city and discover Bellavista Country Estate—a luxurious 12,000 sq. ft. Georgian brick home on 60 private acres in the foothills of the Berkshires, between the Hudson Valley and Berkshires. Perfect for getaways, house-hunting stays, or events, it features 6-9 bedrooms, 5 baths, fireplaces, a stocked kitchen, and formal dining. Enjoy an in-ground pool, gym, home theater, trails, a pond,

  Joseph Briggs William Pitt Sotheby's

  147 Rock City Rd, Old Chatham, NY 12136
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  /24

  $995,000 Sold Jul 16, 2025

  • 2,645 Sq Ft
  • $376/SF
  • 77 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1988

  41 Snydertown Rd, Craryville, NY 12521

  An exceptional, meticulously renovated property, this hilltop retreat blends a modern aesthetic in a natural, private setting for the perfect location to unwind. Escape to this 2,600 sq ft home nestled on your own secluded 4.58 acres minutes to downtown Hudson. This home provides 3 large bedrooms, 2 designer bathrooms, a spacious wrap-around deck and pool. A renovation of this home was

  Beth Cozzolino Gabel Real Estate

  41 Snydertown Rd, Craryville, NY 12521
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  /14

  Not Listed For Sale

  1 - 2 Robinson Rd, Copake, NY 12516

  1 - 2 Robinson Rd, Copake, NY 12516
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  /54

  $560,000

  • 3 Beds
  • 2 Baths
  • 1,917 Sq Ft

  19 Aitken Ave, Hudson, NY 12534

  Charming Arts & Crafts Bungalow - A Perfect Retreat on the Outskirts of Hudson! Discover the perfect blend of vintage charm and modern convenience in this stunning 1927 Arts and Crafts bungalow, ideally located just a stroll away from Greenport's convenience shops and the vibrant downtown Hudson, known for its antique shops, art galleries, and delightful restaurants. Set on a lush 0.14-acre lot,

  Barbara Robinson Red Apple Realty

  19 Aitken Ave, Hudson, NY 12534
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  /20

  $9,500 per month

  • 3 Beds
  • 2.5 Baths
  • 4,000 Sq Ft
  • House for Rent

  387 Tishauser Rd, Hudson, NY 12534

  Enjoy the summer in this beautiful mid-century home high on a hill with expansive Catskill views, 10 minutes to Hudson.Originally built in 1957, to the highest standards, this completely updated home has been stylishly renovated and furnished by the new owner (a prominent professional design expert) using the best interpretation of mid-century modern style. Located high above a quiet country

  Peggy Lampman Peggy Lampman

  387 Tishauser Rd, Hudson, NY 12534
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  $610,000 Sold Jul 15, 2025

  • 1,670 Sq Ft
  • $365/SF
  • 24 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1950

  161 Camp Rd, Red Hook, NY 12571

  A cozy, light-filled cottage tucked away at the end of a quiet country cul-de-sac in Columbia County. Surrounded by trees, a meandering stream, and the gentle sounds of birds chirping in the woods - this adorable cottage is the kind of place you settle into and never want to leave.This home lives simply and beautifully, with natural sunlight pouring in through every window. The main floor

  Craig Smith Compass Greater NY, LLC

  161 Camp Rd, Red Hook, NY 12571
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  Not Listed For Sale

  0 Mitchell St Unit 132496, Hillsdale, NY 12529

  0 Mitchell St Unit 132496, Hillsdale, NY 12529
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  /7

  $275,000

  • 2 Beds
  • 2 Baths
  • 1,232 Sq Ft

  394 Peaceful Valley Rd, Canaan, NY 12029

  Cozy, light-filled 2-bedroom country cottage on 4.75 private acres in Canaan. With a little elbow grease, this property can become a true gem. Just minutes from all the shops, dining, and events in Chatham Village, it's also close to the Berkshires and offers an easy commute to Albany.

  Kelly Harrison Taconic Valley Real Estate

  394 Peaceful Valley Rd, Canaan, NY 12029
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  /27

  $2,500 per month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • House for Rent

  1423 County Route 7, Ancram, NY 12502

  SEASONAL RENTAL ~ Cozy 2 bedroom Cottage in private, quiet location, right in the heart of the Hudson Valley, just off the Taconic Parkway. Nestled in the rolling hills of Columbia County. 20 minutes from Hudson New York, 20 mins from the Berkshires, and 10mins from Bash-Bish Falls. Seasonal rental consists of a loft bedroom with adjoining deck on the upper floor of an Art Studio. On the ground

  Margaret Bower Avenia Columbia County RE Specialist

  1423 County Route 7, Ancram, NY 12502
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  /30

  $348,000 Sold Jul 15, 2025

  • 1,570 Sq Ft
  • $222/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1973

  2226 County Route 27, Hudson, NY 12534

  Wonderful 3 bedroom, 2 full bath Claverack raised ranch set back from the road on 1.53 acres - ready for a new family to love. First floor boasts open concept kitchen (updated in last 10 years) that extends to the dining room and living room. Smaller bedroom off of the living room is currently used as an at home office. Two remaining large bedrooms with primary having full updated bath. No

  Karen Westman Berkshire Hathaway HomeService

  2226 County Route 27, Hudson, NY 12534
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  /4

  Not Listed For Sale

  31 - 33 Spring St, Hudson, NY 12534

  31 - 33 Spring St, Hudson, NY 12534
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  /26

  $175,000

  • 3 Beds
  • 2 Baths
  • 2,016 Sq Ft

  978 U S 20 Unit 18, New Lebanon, NY 12125

  Step in to this sweet 1999 double wide in a well kept park. A massive dining room steps down to a living room/kitchen open space. Brand new carpeting. Three bedrooms including a main bedroom ensuite with a walk in closet and an oversized bath with two sinks, shower and jetted tub. Enjoy your beautiful yard overlooking a pond in the back. Monthly lot rent is $540. Right off of route 20 with

  Sharon McArdle Berkshire Hathaway Home Services Blake

  978 U S 20 Unit 18, New Lebanon, NY 12125
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  /36

  $5,450 per month

  • 5 Beds
  • 3.5 Baths
  • 2,900 Sq Ft
  • House for Rent

  138 Cr 10, Germantown, NY 12526

  Charming center hall farmhouse, with exceptionally well-preserved architectural details. The expansive and light-filled home has been appropriately modernized without losing its abundance of character. The original doors, hardware, and wide-plank hardwood floors have been carefully restored. There are four bedrooms on the second floor and an additional room downstairs with an en-suite full

  Antonio Parrotta Coldwell Banker Village GreenN

  138 Cr 10, Germantown, NY 12526
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  /43

  $890,000 Sold Jul 15, 2025

  • 2,245 Sq Ft
  • $396/SF
  • 239 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2001

  192 Old Queechy Rd, Canaan, NY 12029

  Nestled on 8.6 private acres, surrounded by nature conservancy and historic preservation land, this architect-designed compound offers the perfect blend of understated elegance and contemporary comfort. Located just minutes from Tanglewood, Jacob's Pillow, Kripalu, and world-class skiing in NY, MA, and Vermont, this serene escape is also within walking distance of one of the cleanest lakes in New

  Jean Howard RE/MAX Solutions - Troy

  192 Old Queechy Rd, Canaan, NY 12029
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  Not Listed For Sale

  • 1 Bed
  • 7,514 Sq Ft

  1547 Route 9, Tivoli, NY 12583

  1547 Route 9, Tivoli, NY 12583
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  /42

  $1,450,000

  • 2 Beds
  • 2 Baths
  • 1,475 Sq Ft

  1701 Harlemville Rd, Chatham, NY 12037

  HIGH FIELDS, the perfect hilltop retreat. Up a long, private driveway, this contemporary home offer complete privacy on 14.7 acres of light woods, trails and meadows below. Designed by architect Warren Temple Smith, this contemporary design is thoughtfully integrated to the surrounding nature. High ceilings and glass walled rooms fill the home with natural light. Breathtaking, long distance

  Beth Cozzolino Gabel Real Estate

  1701 Harlemville Rd, Chatham, NY 12037
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  /11

  $2,500 per month

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Apartment for Rent

  339 State St, Hudson, NY 12534

  Stunning, light-filled 2nd floor apartment with ALL UTILITIES (inc. share of internet) included in rental price. Minutes from the heart of Warren Street, this spacious accommodation offers approx. 1,050 sf of living space, including 2 bedrooms, large reception / kitchen and rear deck with panoramic views.The 2-apartment building is set back from State Street in a quiet location, but is only a

  Peter Darrell Tri Hudson Realty, LLC

  339 State St, Hudson, NY 12534
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  /27

  $420,000 Sold Jul 15, 2025

  • 1,824 Sq Ft
  • $230/SF
  • 21 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1979

  29 Viewmont Rd, Copake, NY 12516

  Meticulously maintained with a sense of timeless elegance. Discover this beautiful and peaceful 3-bedroom, 3-bath home nestled on just under an acre of land and located on a quiet cul-de-sac of well maintained homes. This classic raised-ranch style home has an abundance of light streaming in every window that will captivate your senses and leave you inspired.This spacious home offers 1,824

  Margaret Bower Avenia Columbia County RE Specialist

  29 Viewmont Rd, Copake, NY 12516
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  /26

  Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 6,800 Sq Ft

  235 McCagg Rd, Kinderhook, NY 12106

  235 McCagg Rd, Kinderhook, NY 12106

Showing Results 241 - 280, Page 7 of 18