Pine Plains, NY Homes

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  /21

  $599,000

  • 4 Beds
  • 4 Baths
  • 3,928 Sq Ft

  115-133 Mount Ross Rd, Pine Plains, NY 12567

  Historic 1880s Farmhouse with Expansive AcreageAn impressive home of distinction, this spacious 1880s farmhouse, enhanced by 20th-century additions, featuring soaring ceilings and beautiful original woodwork. While the home requires extensive updates, its charm and potential are extraordinary. Set on 65 acres of pristine land, the property offers a pond, a solid barn, an open meadow, and

  

  Larry Havens

  Havens Real Estate

  (518) 671-8313

  115-133 Mount Ross Rd, Pine Plains, NY 12567
• 

  

  

  /31

  $6,500 per month

  • 1 Bed
  • 1.5 Baths
  • 936 Sq Ft
  • House for Rent

  43 Lake Shore Dr, Pine Plains, NY 12567

  Welcome to The Lake Cottage – A Rare Seasonal Retreat on Twin Island LakeDiscover The Lake Cottage, a one-of-a-kind, fully furnished seasonal escape on the shores of Twin Island Lake. This private lakefront compound offers a tranquil and inspiring setting, making it the perfect getaway for artists, writers, creatives, or anyone in search of rest and renewal.Nestled behind lush, mature

  

  SHERI SCEROLER

  Four Seasons Sothebys Intl

  (518) 676-2689

  43 Lake Shore Dr, Pine Plains, NY 12567
• 

  $250,000 Sold Dec 16, 2024

  • Land
  • 9 Acres
  • $28,802 per Acre

  • 87 Days On Market

  3362 New York 199, Pine Plains, NY 12567

  Discover your perfect retreat on this 8.68-acre parcel, nestled in the heart of nature. This land offers a rare combination of privacy, tranquility, and convenience, with all the hard work already done for you.A 1,000-foot driveway leads you through lush woods to the cleared site of your future dream home, where the foundation for a 2,280-square-foot residence and a spacious 1,204-square-foot

  Richard Brenner Rich Brenner Realty, LLC

  3362 New York 199, Pine Plains, NY 12567
• 

  Est $1,222,600 Not Listed For Sale

  454 Bean River Rd, Pine Plains, NY 12567

  454 Bean River Rd, Pine Plains, NY 12567
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  /16

  $535,000

  • 3 Beds
  • 2 Baths
  • 1,768 Sq Ft

  284 Hall Hill Rd-Stop # 18, Ancram, NY 12502

  Spring has sprung and it is such a beautiful time of the year, here in Ancram, New York. The birds are starting to nest and are singing away!This 3 BR, 2 BA, 1768 sf log cabin is sited on 5 acres, and is surrounded by woods and meadows. A full basement below with its own fireplace (never used by these owners with no representation of its condition).There is a separate 3-acre parcel across the

  

  Lindsay Lebrecht

  Copake Lake Realty Corp.

  (518) 217-4718

  284 Hall Hill Rd-Stop # 18, Ancram, NY 12502
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  /47

  $2,311 - $2,800 per month

  Stissing Farm Townhomes

  2 Beds

  51 Hillside Rd, Pine Plains, NY 12567

  Step into the enchanting world of Stissing Farms, where the dream of peaceful living becomes a delightful reality. Starting at just $2,650, these brand-new construction 2 bedroom/2-bathroom rental townhomes in the serene town of Pine Plains offer a charming escape into luxury and comfort.Each home boasts spacious layouts with ceilings soaring over nine feet, creating a breezy, open

  51 Hillside Rd, Pine Plains, NY 12567
• 

  $3,425,000 Sold Apr 16, 2025

  • 5,163 Sq Ft
  • $663/SF
  • 162 Days On Market

  • 6 Beds
  • 4.5 Baths
  • Built 1996

  420 Carpenter Hill Rd, Pine Plains, NY 12567

  This exceptional property offers a unique blend of modern living, luxury and rural tranquility. Fully renovated the estate features a 5100-square-foot main residence, along with a 750-square-foot detached one-bedroom guest apartment located on 13.8 acres. Thoughtfully designed for both comfortable living and entertaining, the home boasts a spacious eat-in kitchen equipped with high-end

  LINDSAY BALDWIN Houlihan Lawrence Inc.

  420 Carpenter Hill Rd, Pine Plains, NY 12567
• 

  Est $738,171 Not Listed For Sale

  • 1 Bed
  • 0.5 Baths
  • 3,204 Sq Ft

  3007 Church St, Pine Plains, NY 12567

  3007 Church St, Pine Plains, NY 12567
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  /4

  $145,000

  • Land
  • 5 Acres
  • $28,884 per Acre

  0 Mount Ross Rd, Pine Plains, NY 12567

  Every once in a while, an exceptional opportunity like this turns up. Located in rural Pine Plains this 5.02-acres is a pair of vacant building lots that offers privacy and serenity. These two contiguous parcels are completely wooded and accessed via a shared driveway. Your dream home is only limited by your imagination these parcels will invigorate that imagination. The Town center and the

  

  Larry Havens

  Havens Real Estate

  (518) 672-6676

  0 Mount Ross Rd, Pine Plains, NY 12567
• 

  

  /19

  $2,750 per month

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

  1684 Route 83, Pine Plains, NY 12567

  Newly renovated 1790's barn is set at the edge of the woods with a terraced view of a rising valley. Wild life roams freely through the property. Birds and butterfly flit about. Solace and privacy abounds. Free to roam the land, use a portion of the garden or sit at the water's edge, the sunlit hill or the meadow for contemplation. This home is fully furnished with the finest furniture, antiques

  CATHERINE HOWARD Corcoran Country Living

  1684 Route 83, Pine Plains, NY 12567
• 

  $810,000 Sold Apr 08, 2025

  • 2,208 Sq Ft
  • $367/SF
  • 61 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1911

  2854 Church St, Pine Plains, NY 12567

  Introducing "Alwynds" ~ a quintessential 1911 Craftsman-style residence, proudly situated in the center of Pine Plains in the enchanting Hudson Valley region of NYS. This impressive home has been lovingly maintained by its owners for over four decades, a testament to its enduring appeal and solid construction. Alwynds exudes classic Craftsman charm, with its distinctive combination of stone and

  Diana Bisselle William Pitt Sothebys Int Rlty

  2854 Church St, Pine Plains, NY 12567
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  /2

  Est $531,177 Not Listed For Sale

  • Studio
  • 4,032 Sq Ft

  7795 S Main St, Pine Plains, NY 12567

  7795 S Main St, Pine Plains, NY 12567
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  /43

  $1,300,000

  • 5 Beds
  • 3 Baths
  • 2,482 Sq Ft

  303 Hicks Hill Rd, Stanfordville, NY 12581

  Nestled on a country road in West Pine Plains, the Historic Hanlon Hill Farmstead offers a rare opportunity to own a piece of history. This 87-acre property, spanning five parcels, has been in the Hanlon family for six generations. The centerpiece is an 1840s eyebrow colonial home, set back from the road for ultimate privacy. As you enter the farm, you'll pass a serene pond and a charming

  HOMER STALEY JR. Staley Real Estate, LLC

  303 Hicks Hill Rd, Stanfordville, NY 12581
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  /20

  $4,000 per month

  • 2 Beds
  • 3 Baths
  • House for Rent

  1495 County Rd 83, Pine Plains, NY 12567

  Fabulous, scenic and private guest house rental on a 14-acre country estate located in the peaceful Shekomeko Valley with pond and pastoral views. An open kitchen, dining, and living area with a wood stove and sliding doors that lead out to your stone patio and the stunning views. Pet is allowed with owner approval. The home is available in early June. Tenant pays heat, electric, internet,

  1495 County Rd 83, Pine Plains, NY 12567
• 

  $370,000 Sold Apr 07, 2025

  • Land
  • 37 Acres
  • $10,093 per Acre

  • 85 Days On Market

  0 Hill Top Rd Unit ONEH6333617, Gallatin, NY 12502

  Rare estate parcel which has commanding views of the Catskills and overlooks protected Scenic Hudson Conservation land.

  Andrew Gates Houlihan Lawrence Inc.

  0 Hill Top Rd Unit ONEH6333617, Gallatin, NY 12502
• 

  Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,712 Sq Ft

  7604 Route 82, Pine Plains, NY 12567

  7604 Route 82, Pine Plains, NY 12567
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  /36

  $1,699,000

  • 5 Beds
  • 3.5 Baths
  • 4,176 Sq Ft

  1598 Jackson Corners Rd, Red Hook, NY 12571

  Welcome to Fallkill Farm, an incredible 37 acre oasis with expansive meadows, wooded buffers, mountain backdrop and Roeliff Jansen Kill frontage. Historic significance and modern amenities converge with the impeccably restored circa 1800 farmhouse featuring updated kitchen w/center island, designer cabinetry, Subzero refrigerator, Wolfe range and soapstone counters. Loaded with period features

  Dan Axtmann BHHS Hudson Valley Properties

  1598 Jackson Corners Rd, Red Hook, NY 12571
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  /23

  $4,000 per month

  • 2 Beds
  • 2.5 Baths
  • 2,160 Sq Ft
  • House for Rent

  1495 Route 83, Pine Plains, NY 12567

  Fabulous, scenic 2 bedroom guest home on a 14 acre country estate located in the peaceful Shekomeko Valley with a pond and pastoral views. Enjoy an open kitchen, dining, and living area with a wood stove and sliding doors that lead out to your stone patio with stunning views. The home has a separate driveway from the main estate house and plenty of privacy. A pet is allowed with the owners

  Jane Kelly Corcoran Country Living - Mill

  1495 Route 83, Pine Plains, NY 12567
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  /4

  $370,000 Sold Apr 07, 2025

  • Land
  • 36 Acres
  • $10,184 per Acre

  • 85 Days On Market

  0 Hill Top Rd Unit 155018, Gallatin, NY 12502

  Rare estate parcel which has commanding views of the Catskills and overlooks protected Scenic Hudson Conservation land.

  Andrew Gates Houlihan Lawrence, Inc.

  0 Hill Top Rd Unit 155018, Gallatin, NY 12502
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  /9

  Not Listed For Sale

  0 County Route 11, Pine Plains, NY 12567

  0 County Route 11, Pine Plains, NY 12567
• 

  

  /37

  $1,595,000

  • 4 Beds
  • 3 Baths
  • 3,980 Sq Ft

  235 Knob Hill Rd, Stanfordville, NY 12581

  Nestled on 56 private acres of lush landscapes, meandering trails and impressive stone walls, you will find two very special vintage homes, sizeable barn, outdoor sauna and shower plus small artist studio. Built in 1850 this two bedroom farmhouse combines historical character with contemporary amenities, featuring gleaming wood and wide board floors, beamed ceilings, stone fireplace, central air

  Jeannine Simmons Corcoran Country Living

  235 Knob Hill Rd, Stanfordville, NY 12581
• 

  

  /20

  $30,000 per month

  • 5 Beds
  • 4 Baths
  • House for Rent

  28 Conklin Hill Rd, Stanfordville, NY 12581

  SUMMER RENTAL - Available July 1, 2025 - August 31, 2025 for $30,000 per month. Exquisite 1790's country house completely restored and beautifully furnished. There are period moldings, five fireplaces, five bedrooms, four baths, and a generator. Also, a 20' x 50' gunite salt water pool with pool house fully equipped with full kitchen and bath. There is a separate building near the pool with a

  28 Conklin Hill Rd, Stanfordville, NY 12581
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  /38

  $390,000 Sold Apr 04, 2025

  • 1,850 Sq Ft
  • $211/SF
  • 46 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1870

  717 County Route 7, Pine Plains, NY 12567

  Gallatinville, in Gallatin, Columbia County, NY, is known for its rich history and picturesque landscapes. Formed in 1830 and named after Albert Gallatin, it remains a quaint and peaceful community, surrounded by the natural beauty of the Roeliff Jansen Kill and rolling hills. Originally rumored to the :Gallatinville Hotel, this renovated 1830s charmer has been transformed into a very enchanting

  Brad Rebillard Dutchess Country Realty, Inc.

  717 County Route 7, Pine Plains, NY 12567
• 

  Est $4,220,417 Not Listed For Sale

  • 5 Beds
  • 6 Baths
  • 5,956 Sq Ft

  112 N Farm Way, Stanfordville, NY 12581

  112 N Farm Way, Stanfordville, NY 12581
• 

  

  /34

  $1,575,000

  • 3 Beds
  • 3 Baths
  • 3,833 Sq Ft

  617 Bean River Rd, Millerton, NY 12546

  Major Update! Meticulously Maintained ELEVATED 3 BEDROOM/3 BATH Log Cabin-Style home and horse barns on 19+ acres with BREATHTAKING views. Set off a quiet country road, this stunning setting with impeccably manicured grounds captures one's attention upon arrival. One is immediately drawn to the expansive wood deck complete with built-in grill and impressive screened-in gazebo with fire-pit. This

  Diana Bisselle William Pitt Sothebys Int Rlty

  617 Bean River Rd, Millerton, NY 12546
• 

  

  /31

  $3,995 per month

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft
  • House for Rent

  1517 Route 83, Pine Plains, NY 12567

  This is your peaceful Hudson Valley retreat. Charming Picardy Farm, located on 10 quiet acres in the bucolic Shekomoko Valley is ready for immediate experiences and exploration. The sophisticated, fully furnished barn conversion includes 3 bedrooms, a stunning Great Room with dining, cathedral beamed ceiling, eat- in country kitchen, charming windowed porch and more. You enter the property off a

  Steve Bruman Corcoran Country Living

  1517 Route 83, Pine Plains, NY 12567
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  /7

  $130,000 Sold Apr 04, 2025

  • 1,153 Sq Ft
  • $113/SF
  • 119 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1870

  10 Academy St, Pine Plains, NY 12567

  Great Investment Opportunity. House has good bones and has been cleared out. Located in Historic Town of Pine Plains within walking distance to center of Town. House is being sold as is.

  Libby McKee Berkshire Hathaway HomeService

  10 Academy St, Pine Plains, NY 12567
• 

  

  /32

  Not Listed For Sale

  • 4 Beds
  • 2,892 Sq Ft

  3004 Church St Unit 30, Pine Plains, NY 12567

  3004 Church St Unit 30, Pine Plains, NY 12567
• 

  

  /37

  $1,575,000

  • 3 Beds
  • 3 Baths
  • 3,833 Sq Ft

  617 Bean River Rd, Pine Plains, NY 12567

  Major Update! Meticulously Maintained ELEVATED 3 BEDROOM/3 BATH Log Cabin-Style home and horse barns on 19+ acres with BREATHTAKING views. Set off a quiet country road, this stunning setting with impeccably manicured grounds captures one's attention upon arrival. One is immediately drawn to the expansive wood deck complete with built-in grill and impressive screened-in gazebo with fire-pit. This

  Diana Bisselle William Pitt Sotheby's Int'l

  617 Bean River Rd, Pine Plains, NY 12567
• 

  

  /20

  $3,995 per month

  • 3 Beds
  • 1 Bath
  • House for Rent

  1517 County Rd 83, Pine Plains, NY 12567

  This is your peaceful Hudson Valley retreat. Charming Picardy Farm, located on 10 quiet acres in the bucolic Shekomoko Valley is ready for immediate experiences and exploration. The sophisticated, fully furnished barn conversion includes 3 bedrooms, a stunning Great Room with dining, cathedral beamed ceiling, eat- in country kitchen, charming windowed porch and more. You enter the property off a

  1517 County Rd 83, Pine Plains, NY 12567
• 

  $250,000 Sold Apr 01, 2025

  • 1,248 Sq Ft
  • $200/SF
  • 77 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1951

  97 North Rd, Red Hook, NY 12571

  Utilized as a weekend retreat for decades, this two-bedroom, two-bathroom home is available for the first time in a long time. The house sits on 1.8 acres and is set back off the roadway and surrounded by trees for privacy. There are two garages and two more storage sheds . A large deck welcomes you to the front door. Centrally situated between Red Hook, Rhinebeck, Pine Plains, Millbrook and

  Richard Brenner Rich Brenner Realty, LLC

  97 North Rd, Red Hook, NY 12571
• 

  

  /64

  Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,250 Sq Ft

  65 Lake Shore Dr Unit 69, Pine Plains, NY 12567

  65 Lake Shore Dr Unit 69, Pine Plains, NY 12567
• 

  

  /22

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,037 Sq Ft

  22-28 Ryan Rd, Pine Plains, NY 12567

  Looking for a value opportunity to acquire a piece of property, for a great low price? Looking for two homes for the price of one? Here is a great opportunity for you to acquire one manufactured home, and one mobile home, both on the same plot of land with 2.30 acres! Investors will consider this property for rental income. Those interested in home ownership will consider this property as well,

  JORGE LUGO BHHS Hudson Valley Properties

  22-28 Ryan Rd, Pine Plains, NY 12567
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  /34

  $4,995 per month

  • 3 Beds
  • 2.5 Baths
  • 1,600 Sq Ft
  • House for Rent

  1515 Route 83 Unit 15, Pine Plains, NY 12567

  Hudson Valley experiences await you with this bucolic setting at Picardy Farm. Once the home of one of the finest jazz musicians, composer, bandleader, actor and author, Artie Shaw, the 19th Century Greek Revival property includes The Garden House now available for lease. This 3 bedroom, 2.5 bath home is FULLY FURNISHED and ready for you to realign with nature and all that upstate New York has to

  Steve Bruman Corcoran Country Living

  1515 Route 83 Unit 15, Pine Plains, NY 12567
• 

  $307,500 Sold Mar 20, 2025

  • 2,328 Sq Ft
  • $132/SF
  • 43 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1872

  3088 Church St, Pine Plains, NY 12567

  Located at the edge of the town center on about a third of an acre, this 3 bedroom, 2 bathroom colonial style home is waiting for a fresh start. The side entrance from the driveway finds a mud room and laundry room. From there you’ll find a spacious kitchen attached to a nicely sized dining room. Pass through the center hall to a large living room adorned by a gas fireplace. The center hall

  Richard Brenner Rich Brenner Realty, LLC

  3088 Church St, Pine Plains, NY 12567
• 

  Est $780,064 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  114 Maple Hill Ln, Pine Plains, NY 12567

  114 Maple Hill Ln, Pine Plains, NY 12567
• 

  

  /23

  $299,000

  • 4 Beds
  • 1.5 Baths
  • 1,328 Sq Ft

  6 Carla Terrace, Pine Plains, NY 12567

  Welcome to 6 Carla Terrace! This 4-bedroom ranch nestled on a quiet tree lined cul-de-sac is well situated on nearly a half-acre level lot featuring a large private driveway for multiple vehicles. The dining area features sliding glass doors to the rear deck. Conveniently located just a short distance to downtown Pine Plains and its great shops, restaurants, schools, and of course, the Stissing

  Theodore Weinstein REO Edge LLC

  6 Carla Terrace, Pine Plains, NY 12567
• 

  

  /20

  $4,995 per month

  • 3 Beds
  • 3 Baths
  • House for Rent

  1504 County Rd 83, Pine Plains, NY 12567

  Hudson Valley private hillside retreat with south western mountain views. Quiet and special, this is located in the desirable Shekomeko Valley. This contemporary country home is on over 30 bucolic acres. Set well off the beautiful country road, the driveway leads to this renovated haven. Gorgeous vistas of countryside farms and mountains, the landscaping allows for relaxing exploration and

  1504 County Rd 83, Pine Plains, NY 12567
• 

  $1,975,000 Sold Mar 17, 2025

  • 4,144 Sq Ft
  • $477/SF
  • 428 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2000

  0 Dewitt Ln Unit KEYM418621, Ancramdale, NY 12503

  The options are endless for this very special 120-acre property on a spectacular country road in beautiful Ancramdale, NY. The property, which has been a family compound for multiple generations, begins with a very long private driveway that leads to the original 1850's farmhouse and guest cottage overlooking a gorgeous 4+ acre pond. As you continue down the driveway, past lovely rolling hills,

  Neil Charles Neil Charles Real Estate, LLC

  0 Dewitt Ln Unit KEYM418621, Ancramdale, NY 12503
• 

  Est $607,383 Not Listed For Sale

  • 3 Beds

  308 Hall Hill Rd, Ancram, NY 12502

  308 Hall Hill Rd, Ancram, NY 12502

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