Dutchess, NY Homes

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  $729,000 Open Sun 11AM - 2PM

  • 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
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  $2,800 - $2,850 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 $2,800, 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
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  $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
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  Est $1,522,823 Not Listed For Sale

  454 Bean River Rd, Pine Plains, NY 12567

  454 Bean River Rd, Pine Plains, NY 12567
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  $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
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  /41

  $5,750 per month

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

  422 County Route 7, Pine Plains, NY 12567

  An attractive Cape Cod style farmhouse that offers outstanding views of beautiful rolling farmland and Stissing Mountain. This year-round rental features a comfortable floor plan with a wonderful country kitchen that opens to a dining area with access to a screened in porch overlooking pleasant views of sweeping meadow. The dining area flows beautifully into the spacious living room with a new

  Susan Whalen George T Whalen Real Estate

  422 County Route 7, Pine Plains, NY 12567
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  $290,000 Sold Jun 30, 2025

  • Land
  • 9 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
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  Est $740,010 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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  $3,600,000

  • Land
  • 229 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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  $2,300 per month

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft
  • Apartment for Rent

  525 Lake Rd Unit 4, Pine Plains, NY 12567

  BEAUTIFUL LAKE VIEW FROM YOUR FRONT DOOR !! Newly updated Kitchen, All new Floors, Freshly Cleaned and Painted two bedroom apartment. Situated up a hill with a great view of the beautiful Twin Island Lake - some lake rights included. The fishing is excellent ! Landlord pays heat, hot water, snow removal, lawn mowing & trash collection. Also has covered patio, off street parking and circular

  MICHELLE FRANCESE Corcoran Country Living

  525 Lake Rd Unit 4, 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 $532,500 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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  $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
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  /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
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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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  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
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  $285,000

  • Land
  • 9 Acres
  • $32,872 per Acre

  3362 New York 199, Pine Plains, NY 12567

  Here is an opportunity for you to build your dream home.8.67 acres of land in Pine Plain in Dutchess County, New York is for sale. This exceptional property is situated behind a 70-foot road frontage on Route 199.Key Features:Location: Pine Plains in Dutchess County, New YorkLand Size: 8.67 acresAccess: 70 feet of road frontage on Route 199Amenities: Cleared

  Community Lands

  3362 New York 199, Pine Plains, NY 12567
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  /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
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  $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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  Not Listed For Sale

  0 County Route 11, Pine Plains, NY 12567

  0 County Route 11, Pine Plains, NY 12567
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  /21

  $749,000

  • 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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  $440,000 Sold May 08, 2025

  • Land
  • 44 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 $777,169 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
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  $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
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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 $599,156 Not Listed For Sale

  • 3 Beds

  308 Hall Hill Rd, Ancram, NY 12502

  308 Hall Hill Rd, Ancram, NY 12502
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  $900,000

  • 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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  $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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  Est $319,414 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
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  $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
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  Sold Apr 07, 2025

  • Land
  • 36 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 $1,322,166 Not Listed For Sale

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

  140 Mountain Rd, Stanfordville, NY 12581

  140 Mountain Rd, Stanfordville, NY 12581
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  $995,000

  • 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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  $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
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  Est $820,912 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
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  $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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  $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 $254,472 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,506 Sq Ft

  196 Mountain Rd, Stanfordville, NY 12581

  196 Mountain Rd, Stanfordville, NY 12581
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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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  $390,000 Sold Apr 04, 2025

  • 1,850 Sq Ft
  • $211/SF
  • 49 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

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