Pine Plains, NY Homes

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  /43

  $899,000

  • 5 Beds
  • 3.5 Baths
  • 2,714 Sq Ft

  198 Sigler Rd, Pine Plains, NY 12567

  This architect designed and custom built passive solar home and guest house is sited privately on 17.90 acres with panoramic views of the of the eastern valley plains to Stissing Mountain and beyond. The tree lined driveway leads you to both houses that sit high on the land, facing south over looking the property fields & pond. Perfectly sited for the passive solar design and the solar panel

  Kimberly Baker BHHS Hudson Valley Properties

  198 Sigler Rd, Pine Plains, NY 12567
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  $340,000 Sold Jun 20, 2025

  • 1,728 Sq Ft
  • $197/SF
  • 29 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1800

  712 County Route 7, Pine Plains, NY 12567

  Circa 1800 eyebrow colonial located in the bucolic hamlet of Gallatin. This home was completely renovated down to the studs in 2020 with new mechanicals, plumbing, electrical, mini split units, roof, windows, and was spray foam insulated throughout. The house was just freshly painted. The main floor offers a spacious living room, dining room, kitchen and half bath with wide board pine floors

  PAULA REDMOND Corcoran Country Living

  712 County Route 7, Pine Plains, NY 12567
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  Est $464,281 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,272 Sq Ft

  3469 Route 199, Pine Plains, NY 12567

  3469 Route 199, Pine Plains, NY 12567
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  $1,175,000

  • 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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  $302,000 Sold May 22, 2025

  • 1,370 Sq Ft
  • $220/SF
  • 16 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1958

  84 Cottontail Rd, Ancram, NY 12502

  This darling house received a lot of TLC. The owner renovated almost the entire interior. It has a new kitchen and bath. The floors were refinished and new sconces in LR and DR, new windows throughout and closets in the spacious two bedrooms. The ample and insulated garage is below the 2nd level with an indoor and exterior entrance. Laundry and a great work bench is located in this very dry and

  CATHERINE HOWARD Corcoran Country Living

  84 Cottontail Rd, Ancram, NY 12502
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  /43

  Est $608,280 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,000 Sq Ft

  3327 Route 199, Pine Plains, NY 12567

  3327 Route 199, Pine Plains, NY 12567
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  /36

  $1,499,000

  • 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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  /37

  $1,950,000 Sold May 12, 2025

  • 3,802 Sq Ft
  • $513/SF
  • 42 Days On Market

  • 5 Beds
  • 2.5 Baths
  • Built 1750

  460 Silvernails Rd, Pine Plains, NY 12567

  On just over ten acres of rolling hillside and pasture sits this quintessential Hudson Valley farmhouse. The oldest section of the home dates back to the mid 1700's, quite early for this region, while the Federal Style facade and front rooms were added c1850. The combination is striking the back of the house is both quaint and cozy, while the front of the home has high ceilings, big six-over-six

  Annabel Taylor Four Seasons Sotheby's Int.

  460 Silvernails Rd, Pine Plains, NY 12567
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  /2

  Est $441,320 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,310 Sq Ft

  6 Sheldon Dr, Pine Plains, NY 12567

  6 Sheldon Dr, Pine Plains, NY 12567
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  /11

  $900,000 Pending

  • 5 Beds
  • 2.5 Baths
  • 2,413 Sq Ft

  2365 Route 83, Pine Plains, NY 12567

  Rare opportunity to own 160 breathtaking acres in the heart of Pine Plains, featuring rolling fields, wooded terrain, and scenic wetlands. Anchoring the property is an antique farmhouse awaiting restoration, set within a 7 plus acre residential area offering privacy and pastoral charm. Most of the property is protected under a conservation easement, preserving the natural landscape while allowing

  Richard Brenner Rich Brenner Realty, LLC

  2365 Route 83, Pine Plains, NY 12567
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  /7

  $440,000 Sold May 08, 2025

  • Land
  • 43.53 Acres
  • $10,108 per Acre

  • 202 Days On Market

  0 - TBD County Route 7, Copake, NY 12516

  Here is an amazing opportunity to build on one of the very few large parcels available so close to Copake Lake. This beautiful mix of cleared areas and mature woodland has two building sites with BOH approval served by a driveway already in place. Create a dream compound, or subdivide and sell to offset costs. Either way, the topography offers plenty of privacy.Recently featured in the Wall

  Jeffries Blackerby Houlihan Lawrence Inc.

  0 - TBD County Route 7, Copake, NY 12516
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  Est $2,923,752 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 5,614 Sq Ft

  1990 Route 83, Pine Plains, NY 12567

  1990 Route 83, Pine Plains, NY 12567
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  /34

  $895,000 Pending

  • 2 Beds
  • 1.5 Baths
  • 1,100 Sq Ft

  660 County Route 7, Pine Plains, NY 12567

  The Gallatin House-Small but perfect, this jewel-box home is rich with charm and thoughtful detail.Originally built in the 1850s as a workman’s cottage, this iconic 2-bedroom, 1.5-bath home has been masterfully reimagined by the acclaimed design studio Workstead. Perched high above the Roeliff Jansen Kill and set on over 4 private acres, the property is a refined blend of early American

  SHERI SCEROLER Four Seasons Sothebys Intl

  660 County Route 7, Pine Plains, NY 12567
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  $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
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  Est $670,394 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,640 Sq Ft

  2067 Route 83, Pine Plains, NY 12567

  2067 Route 83, Pine Plains, NY 12567
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  /21

  $749,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,624 Sq Ft

  37 Stissing Mountain Dr, Pine Plains, NY 12567

  Welcome to 37 Stissing Mountain Drive. Perfectly nestled on 6.9 acres of peaceful woodland, this newly built 2-bedroom, 2-bath home is a modern sanctuary that beautifully balances simplicity, sustainability, and style—just minutes from the heart of Pine Plains NY.Inside you will find a sun-filled, open-concept living space with soaring 22-foot vaulted ceilings that frame sweeping views of the

  Jason Nadeau Compass Greater NY, LLC

  37 Stissing Mountain Dr, Pine Plains, NY 12567
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  $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 $353,185 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,250 Sq Ft

  3094 Church St, Pine Plains, NY 12567

  3094 Church St, Pine Plains, NY 12567
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  /35

  $995,000 Under Contract

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

  235 Knob Hill Rd, Stanfordville, NY 12581

  Nestled on 13 private acres of lush landscapes, meandering trails and impressive stone walls, you will find two very special vintage homes, outdoor sauna and shower plus small artist studio. Built in 1850 this two bedroom cottage combines historical character with contemporary amenities, featuring gleaming wood and wide board floors, beamed ceilings, stone fireplace, central air and a gourmet

  Jeannine Simmons Corcoran Country Living

  235 Knob Hill Rd, Stanfordville, NY 12581
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  Sold Apr 07, 2025

  • Land
  • 36.33 Acres

  • 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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  Est $314,205 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,360 Sq Ft

  36 Myrtle Ave, Pine Plains, NY 12567

  36 Myrtle Ave, Pine Plains, NY 12567
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  /11

  $195,000

  • Land
  • 20 Acres
  • $9,750 per Acre

  00-1 New York 82, Pine Plains, NY 12567

  A rare opportunity to turn 20 acres into your next country getaway or full-time residence. A driveway is already roughed in, and soil tests have been done. In a quiet area surrounded by large parcels, this gently sloping and wooded lot offers maximum privacy in a highly desirable central location in southern Columbia County. Just 20 minutes to Hudson and Red Hook, 15 minutes to Millerton and

  Jeffries Blackerby Houlihan Lawrence Inc.

  00-1 New York 82, Pine Plains, NY 12567
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  $370,000 Sold Apr 07, 2025

  • Land
  • 36.66 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
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  Est $520,758 Not Listed For Sale

  • 5 Beds
  • 2 Baths
  • 3,173 Sq Ft

  22 Pine St, Pine Plains, NY 12567

  22 Pine St, Pine Plains, NY 12567
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  /2

  $290,000

  • Land
  • 68.33 Acres
  • $4,244 per Acre

  000 New York 82, Pine Plains, NY 12567

  This beautiful, gently sloping parcel offers the perfect canvas to create your country escape or full-time residence on 68+ private acres. Soil tests have been done on a potential lower building site. A level area at a higher elevation could offer even more privacy and ridgeline views. Dept of Transportation has already approved a driveway. So you're well on your way to building a home that's

  Jeffries Blackerby Houlihan Lawrence Inc.

  000 New York 82, Pine Plains, NY 12567
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  /7

  $130,000 Sold Apr 04, 2025

  • 1,153 Sq Ft
  • $113/SF
  • 118 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
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  Est $359,948 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,703 Sq Ft

  3018 Church St, Pine Plains, NY 12567

  3018 Church St, Pine Plains, NY 12567
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  /7

  $150,000

  • Land
  • 0.93 Acre
  • $161,290 per Acre

  58 Britton St, Pine Plains, NY 12567

  Two lots sold together totaling just under 1 acre. 1000 gallon concrete septic tank and leach fields already in place. Drilled well complete. Under ground 200 amp electric service installed. Current mobile home will be removed. Flat lot with all utilities in a well established residential area just waiting for a new home.

  Richard Brenner Rich Brenner Realty, LLC

  58 Britton St, Pine Plains, NY 12567
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  $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
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  Est $446,237 Not Listed For Sale

  • 6 Beds
  • 2,550 Sq Ft

  17 Smith St, Pine Plains, NY 12567

  17 Smith St, Pine Plains, NY 12567
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  /7

  $139,000

  • Land
  • 4.24 Acres
  • $32,783 per Acre

  620 Bean River Rd, Pine Plains, NY 12567

  Great opportunity for 1 residence (property is in Hamlet Zone and possibly subdividable). Approved Septic design and existing shared driveway. (May need improvement). Newly renovated home on North and vacant 8 acre lot for 225,000 on South. Owner financing possible.

  David Birch Barns & Farms Realty, LLC

  620 Bean River Rd, Pine Plains, NY 12567
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  $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
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  Est $401,549 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,165 Sq Ft

  17 Farview Ave, Pine Plains, NY 12567

  17 Farview Ave, Pine Plains, NY 12567
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  $575,000

  • 4 Beds
  • 2.5 Baths
  • 2,580 Sq Ft

  143 Ryan Rd, Pine Plains, NY 12567

  This 4 Bedroom, 2.5 Bath Classy Contemporary Colonial emulates "Pride of Ownership" and has so much to offer anyone looking for a turnkey home in a wonderful town. As you enter the airy Center Hall you will immediately fall in love with the gleaming Cherry Hardwood Floors that run abundantly through the whole home. Appreciate the Crown Molding that accentuates each room. Marvel at the lofty

  Catherine Mondello Mondello Upstate Properties

  143 Ryan Rd, Pine Plains, NY 12567
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  $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
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  Est $531,205 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,999 Sq Ft

  55 Birch Dr, Pine Plains, NY 12567

  55 Birch Dr, Pine Plains, NY 12567
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  /17

  $295,000

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

  46 Myrtle Ave, Pine Plains, NY 12567

  Check out this charming two family home in the Town of Pine Plains. Live in one unit and keep the other unit rented OR rent out the entire building. One unit was recently updated. Separate utilities and each unit has its own driveway and storage shed. Covered porch, screened-in porch, large backyard. Convenient location, walk to shops & local attractions.

  Susan Whalen George T Whalen Real Estate

  46 Myrtle Ave, Pine Plains, NY 12567
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  /29

  $840,000 Sold Mar 14, 2025

  • 2,092 Sq Ft
  • $402/SF
  • 58 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1968

  348 Willow Glen Rd, Red Hook, NY 12571

  This gorgeous A-frame—featured in both Dwell and Vogue magazines—combines countryside charm with mid-century modernism in the heart of the Hudson Valley. The Red Hook home sits on six wooded acres, around the corner from a natural swimming hole, yet only minutes away from the Taconic State Parkway. A welcoming, cottage-like exterior opens into a thoughtfully designed, architectural home

  Sarah Finch The Kinderhook Group, Inc.

  348 Willow Glen Rd, Red Hook, NY 12571
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  Est $444,346 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,220 Sq Ft

  44 Pine St, Pine Plains, NY 12567

  44 Pine St, Pine Plains, NY 12567
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  /15

  $1,995,000

  • Land
  • 150.48 Acres
  • $13,258 per Acre

  1533-1539 Route 83, Pine Plains, NY 12567

  Discover a rare 150-acre estate in one of the Hudson Valley’s most coveted farmland corridors. This property offers a private building site accessed by a scenic driveway and showcases the best of Hudson Valley living where nature meets luxury. Enjoy panoramic views of protected farmland, Shekomeko Creek, and wooded mountains. Surrounded by conservation land, this estate ensures lasting privacy

  John Panzer Elyse Harney Real Estate

  1533-1539 Route 83, Pine Plains, NY 12567

Showing Results 41 - 80, Page 2 of 18