Pine Plains, NY Homes

• 

  

  

  /50

  $729,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,971 Sq Ft

  546 Hicks Hill Rd, Stanfordville, NY 12581

  Beautiful Colonial lives like a 4-bedroom featuring a covered porch with wooden rocking bench. Enjoy the beauty of over 5 acres of nature. Long driveway leads to 2 car garage set back off the road. Privacy with convenience and a short ride to the Taconic State Parkway. Inside, enjoy the fantastic layout of a perfectly designed colonial with maximum space and superior design including a spacious

  

  Joseph Iannibelli

  Keller Williams NY Realty

  (845) 444-3630

  546 Hicks Hill Rd, Stanfordville, NY 12581
• 

  

  

  /50

  $2,940 - $3,150 per month

  Stissing Farms

  2 Beds

  51 Hillside Rd, Pine Plains, NY 12567

  Live the way you've always wanted without compromising style or quality. At Stissing Farm Townhomes, our apartment residences are designed with you in mind. Now you really can have it all . . . lifestyle included.Pine Plains was named One of the Best Small Towns in New York by !

  51 Hillside Rd, Pine Plains, NY 12567
• 

  $550,000 Sold Sep 18, 2025

  • 1,774 Sq Ft
  • $310/SF
  • 31 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1800

  4 Skiba Rd, Pine Plains, NY 12567

  A darling country house. 4 Skiba sits on a quiet country lane with a sprawling sunlit lawn. The setting is as peaceful as can be, a little slice of heaven. Abutting very large parcels on either side, the land is just shy of an acre and feels expansive and private. Inside there is a wonderful amount of natural light. You’ll find a newly renovated kitchen and an open floor plan. There is a

  Annabel Taylor Four Seasons Sothebys Intl

  4 Skiba Rd, Pine Plains, NY 12567
• 

  Est $1,520,244 Not Listed For Sale

  454 Bean River Rd, Pine Plains, NY 12567

  454 Bean River Rd, Pine Plains, NY 12567
• 

  

  

  /50

  $3,995,000

  • 4 Beds
  • 4 Baths
  • 4,103 Sq Ft

  476 Carpenter Hill Rd, Pine Plains, NY 12567

  Modern Minimalist Masterpiece on 19 Bucolic Acres in Dutchess County. Welcome to a rare offering in the heart of the Hudson Valley, where striking modern architecture meets timeless pastoral beauty. Completed in late 2024, this extraordinary estate sits on over 19 acres of flat, fenced farmland at the picturesque intersection of Bethel Cross and Carpenter Hill Road. Perfectly sited on a

  

  Rebecca Doh

  William Raveis Lifestyles Rlty

  (518) 594-8655

  476 Carpenter Hill 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
• 

  

  /17

  $695,000 Sold Sep 17, 2025

  • 896 Sq Ft
  • $776/SF
  • 26 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1971

  60 County Route 7, Pine Plains, NY 12567

  ACCEPTED OFFER. Available: 7.5 lush acres on the Roe-Jan! A rustic-style late mid-century three-bedroom, two bath home sits in a beautifully landscaped property with nearly 300 feet of footage on the Roeliff Jansen Kill in Gallatin, New York. You approach this quiet and serene hideaway by a long a private drive through shady woods. The home, built by a local lumber dealer, provides a warm and

  David Norman Hall Houlihan Lawrence Inc.

  60 County Route 7, Pine Plains, NY 12567
• 

  Est $756,216 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
• 

  

  /4

  $145,000

  • Land
  • 5.02 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
  • House for Rent

  1684 County Rd 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

  1684 County Rd 83, Pine Plains, NY 12567
• 

  $100,000 Sold Sep 10, 2025

  • 984 Sq Ft
  • $102/SF
  • 79 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1970

  1691 Jackson Corners Rd, Red Hook, NY 12571

  Unique Opportunity Knocks! Visionaries Wanted! Older manufactured home is serving as living quarters for the current family. A separate foundation, building permit and a fully approved set of stamped plans are included with the property which overlooks a lovely, wooded hillside. Replace the current home with newer model or build your dream home or studio. Infrastructure in place includes well,

  Catherine Mondello Mondello Upstate Properties

  1691 Jackson Corners Rd, Red Hook, NY 12571
• 

  /2

  Est $544,162 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
• 

  

  /24

  $379,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft

  48 Woodside St, Pine Plains, NY 12567

  Whether you're beginning retirement or planning a weekend escape, 48 Woodside Street is a charming, move-in-ready home. Pine Plains offers attractions like fine dining at the Stissing House and tranquil kayaking on Thompson Pond. Nearby hiking trails include the challenging Stissing Fire Tower and the peaceful Thompson Preserve, ideal for a leisurely walk. Lions Club Park features a recreation

  

  Brad Rebillard

  DUTCHESS COUNTRY REALTY INC. M

  (518) 662-5219

  48 Woodside St, 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

  43 Lake Shore Dr, Pine Plains, NY 12567
• 

  $537,500 Sold Sep 09, 2025

  • 2,605 Sq Ft
  • $206/SF
  • 37 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1860

  5 Myrtle Ave, Pine Plains, NY 12567

  Beautiful Two Story, 4BR/2BA corner lot home with mountain views & quick walk to post office, shops, Stissing Lake & Stissing Mountain hiking trails. Experience the wonderful life of beautiful Pine Plains living! Wonderful large front, side & back yard on quiet sought after Myrtle Ave. Lovely front porch to sit & enjoy the scenery or head into the private back yard for a BBQ. Walk to school, post

  Thomas Zengen Thomas Zengen

  5 Myrtle Ave, Pine Plains, NY 12567
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  /2

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  7604 Route 82, Pine Plains, NY 12567

  7604 Route 82, Pine Plains, NY 12567
• 

  

  /38

  $559,000

  • 3 Beds
  • 2.5 Baths
  • 2,269 Sq Ft

  540 Hicks Hill Rd, Stanfordville, NY 12581

  Charming 3-bedroom, 2.5-bathroom Colonial nestled on 5.58 private acres. Enjoy quiet moments on your wrap-around rocking chair front porch and take in picturesque views of Stissing Mountain. This inviting home features a spacious living room, formal dining room and an eat-in kitchen that flows into a comfortable family room perfect for gatherings. Step out from the family room onto a patio ideal

  

  Rita Longo

  Howard Hanna Rand Realty

  (329) 209-8590

  540 Hicks Hill Rd, Stanfordville, NY 12581
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  /37

  $665,000 Sold Aug 15, 2025

  • 1,640 Sq Ft
  • $405/SF
  • 27 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1810

  2067 County Road 83, Pine Plains, NY 12567

  Welcome to a little slice of upstate magic. Tucked into the quiet hamlet of Pine Plains, this beautifully restored 1810 cottage offers that elusive blend of historic charm and modern comforts. Set on 1.16 acres of lush gardens and mature trees, the property invites you to slow down and stay awhile. The three-bedroom, two-bath home has been lovingly maintained and updated over the years, with

  William Golan Compass Greater NY, LLC

  2067 County Road 83, Pine Plains, NY 12567
• 

  /2

  Not Listed For Sale

  0 County Route 11, Pine Plains, NY 12567

  0 County Route 11, Pine Plains, NY 12567
• 

  

  /28

  $465,000

  • 3 Beds
  • 1 Bath
  • 1,600 Sq Ft

  3807 Route 199, Pine Plains, NY 12567

  Nestled between the villages of Pine Plains and Millerton, in the hamlet of Pulver's Corners, this single-level home exudes country charm and a cozy vibe. The backyard features a stone patio surrounded by perennial and vegetable gardens, with a picturesque view of a pasture. Morning sunlight beautifully illuminates the rolling hills and farmland beyond. Inside, the home boasts natural wood

  

  Brad Rebillard

  DUTCHESS COUNTRY REALTY INC. M

  (518) 941-8819

  3807 Route 199, Pine Plains, NY 12567
• 

  $390,000 Sold Aug 11, 2025

  • Land
  • 24.99 Acres
  • $15,606 per Acre

  • 54 Days On Market

  285 South Rd, Stanfordville, NY 12581

  Welcome to 24.99 Acres of Scenic Tranquility and Endless PossibilitiesDiscover the beauty and serenity of nearly 25 acres of gently rolling, wooded land, featuring captivating natural water elements—including two tranquil ponds and a meandering stream. A constructed driveway and underground electric service lead you deep into the heart of the property, where a charming barn stands

  Michael Tellerday Houlihan Lawrence Inc.

  285 South Rd, Stanfordville, NY 12581
• 

  Est $652,178 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
• 

  

  /24

  $3,600,000

  • Land
  • 228.91 Acres
  • $15,727 per Acre

  0 Skunks Misery Rd Unit KEY860535, Pine Plains, NY 12546

  Sensational vistas of the stunning and unspoiled countryside extending to the Taconic's to the East and from a hidden knoll with an elevation of 1,250' there is a magnificent private setting with incredible Catskill views. The main parcel of 157 acres is offered for the first time in generations and that parcel adjoins a 71.5-acre parcel, this was a family owned and operated farm. Both properties

  

  Larry Havens

  Havens Real Estate

  (518) 676-2868

  0 Skunks Misery Rd Unit KEY860535, Pine Plains, NY 12546
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  /40

  $3,100,000 Sold Aug 07, 2025

  • 3,264 Sq Ft
  • $950/SF
  • 127 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2006

  182 Hill Top Rd, Pine Plains, NY 12567

  Luxurious modern farmhouse on 16.17 acres of pristine conservation land within a protected 660-acre viewshed, two ponds, sweeping mountain and country vistas to savor from the wraparound porch, soaring ceiling heights, clean lines and carefully crafted materials from a 2023 comprehensive design-forward renovation featured in Elle Decor.In the main house, the new chef's kitchen gleams with

  Katherine Wood Patricia A. Hinkein Realty

  182 Hill Top Rd, Pine Plains, NY 12567
• 

  Est $617,637 Not Listed For Sale

  • 3 Beds

  308 Hall Hill Rd, Ancram, NY 12502

  308 Hall Hill Rd, Ancram, NY 12502
• 

  

  /45

  $850,000

  • 3 Beds
  • 3 Baths
  • 1,800 Sq Ft

  717 County Route 7, Pine Plains, NY 12567

  This classic 19th century farmhouse in the quiet country hamlet of Gallatinville has undergone a complete transformation. With a designer's eye, 19th century details of wide board floors and beams are retained and blended with sublime, modern comforts. Soft colors bathe the house throughout, including the spacious light filled living room. The kitchen and dining area is anchored by a large

  Sarah Lipsky William Pitt Sothebys Intn'l

  717 County Route 7, Pine Plains, NY 12567
• 

  

  /13

  $924,500 Sold Aug 07, 2025

  • Land
  • 105.45 Acres
  • $8,767 per Acre

  • 113 Days On Market

  Tbd Woods Dr, Ancramdale, NY 12503

  Welcome to your 105-acre dreamscape in the heart of Columbia County, nestled in charming Ancramdale. This sprawling property offers the perfect blend of natural beauty and tranquil seclusion, with endless opportunities to create your private retreat or agricultural haven.Take in breathtaking views across rolling meadows, fields, and wooded areas, complemented by two serene ponds and the

  Arlena Armstrong Anatole House LLC

  Tbd Woods Dr, Ancramdale, NY 12503
• 

  Est $337,044 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 740 Sq Ft

  44 Conklin Hill Rd, Stanfordville, NY 12581

  44 Conklin Hill Rd, Stanfordville, NY 12581
• 

  

  /7

  $1,995,000

  • 3 Beds
  • 2.5 Baths
  • 2,267 Sq Ft

  820 Cold Spring Rd, Stanfordville, NY 12581

  (To be built) Perfectly sized upstate retreat, Zenith integrates seamlessly with its bucolic setting, minutes from Rhinebeck village. The low pitched angled roof planes intersect in the residence’s great room with clerestory windows to flood the living spaces with light.Zenith is sited on 7 private primarily wooded acres. The residence showcases interiors with natural textures and a

  DOUG MAXWELL Upstate Modernist

  820 Cold Spring Rd, Stanfordville, NY 12581
• 

  $2,510,460 Sold Aug 06, 2025

  • 4,000 Sq Ft
  • $628/SF
  • 300 Days On Market

  • 6 Beds
  • 5.5 Baths
  • Built 1850

  53 Brooks Rd, Pine Plains, NY 12567

  Welcome to Library Valley Estate, a creative 3-home compound in Dutchess County, NY. This serene, terraced property features a lovingly restored 19th-century farmhouse, a spacious barn-style home with a vaulted ceiling and oversized sliding glass doors, and a cozy loft studio, each offering stunning views of the rolling meadows. Enjoy a heated gunite pool, mature gardens, a quaint pond, and

  Anthony D'Argenzio Houlihan Lawrence, Inc

  53 Brooks Rd, Pine Plains, NY 12567
• 

  Est $974,710 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,568 Sq Ft

  140 Mountain Rd, Stanfordville, NY 12581

  140 Mountain Rd, Stanfordville, NY 12581
• 

  

  /37

  $1,225,000

  • 4 Beds
  • 2 Baths
  • 1,888 Sq Ft

  174 County Route 11, Pine Plains, NY 12567

  Expansive 55+ Acre Multi-Home Compound. A rare opportunity to own a one-of-a-kind compound set on 57.44 private, picturesque acres—ideal for multi-generational living or a unique investment. The main residence offers 1,888 square feet of rustic charm and comfort, featuring 4 bedrooms and 2 full baths. Enjoy cozy evenings in the living room with pegged oak floors, pine paneling, and a classic

  Paula Redmond Corcoran Country Living - Mill

  174 County Route 11, Pine Plains, NY 12567
• 

  

  /32

  $280,000 Sold Aug 01, 2025

  • 1,368 Sq Ft
  • $205/SF
  • 73 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1880

  1283 County Route 7, Ancram, NY 12502

  Own a piece of history with this one of a kind 3BR, 2Bath, charming 1800's farmhouse right in the center of the historic district of Ancram. Large eat-in kitchen complete with newer stainless steel appliances, radiant heated flooring, spacious pantry, efficient wood burning stove, and first bathroom. Open living room has an abundance of natural light and beautiful views of the neighboring hills.

  Margaret Clarke Corcoran Country Living

  1283 County Route 7, Ancram, NY 12502
• 

  

  /33

  Est $837,053 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,486 Sq Ft

  218 Mountain Rd, Stanfordville, NY 12581

  218 Mountain Rd, Stanfordville, NY 12581
• 

  

  /38

  $875,000

  • 4 Beds
  • 1.5 Baths
  • 2,709 Sq Ft

  7668 Route 82, Pine Plains, NY 12567

  Looking for a property that offers an opportunity for a homestead lifestyle in the Hudson Valley? Situated in the Town of Pine Plains, this early colonial farmhouse is now offered for sale on 15+ acres. Appointed with wide-plank floors, the main level features sun-lit, well-proportioned rooms. On the second floor, there is a primary bedroom with a dressing room, 3 additional bedrooms, an

  Susan Whalen George T Whalen Real Estate

  7668 Route 82, Pine Plains, NY 12567
• 

  $520,000 Sold Jul 28, 2025

  • 3,928 Sq Ft
  • $132/SF
  • 285 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1880

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

  My client wants this property to continue to be shown. There is an accepted offer. 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

  Larry Havens Havens Real Estate

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

  Est $329,179 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,506 Sq Ft

  196 Mountain Rd, Stanfordville, NY 12581

  196 Mountain Rd, Stanfordville, NY 12581
• 

  

  /30

  $925,000

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

  1388 Route 83, Pine Plains, NY 12567

  This c. 1880 three-story farmhouse seamlessly blends historic charm with modern luxury, meticulously cared for and thoughtfully curated to offer both timeless elegance and contemporary comfort.Step inside and be greeted by the inviting, light-filled living room. This spacious area exudes classic sophistication, centered around a warming wood-burning fireplace and boasting large windows that

  Jill Rose Houlihan Lawrence Inc.

  1388 Route 83, Pine Plains, NY 12567
• 

  $290,000 Sold Jun 30, 2025

  • Land
  • 9.25 Acres
  • $31,351 per Acre

  • 91 Days On Market

  15 Ferris Ln, Red Hook, NY 12571

  Situated on a charming country road in Dutchess County is this board of health approved 9.25 acre parcel and is ready to be built on. The property has a meadow that rises to the proposed house site with far reaching views of the rolling hills and surrounding farmland. There is road frontage on both Academy Hill and Ferris Lane. Conveniently located between Pine Plains and Rhinebeck, and just

  PAULA REDMOND Corcoran Country Living

  15 Ferris Ln, Red Hook, NY 12571
• 

  Est $453,813 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,268 Sq Ft

  459 Schultz Hill Rd, Pine Plains, NY 12567

  459 Schultz Hill Rd, Pine Plains, NY 12567

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