Dutchess, NY Homes

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  /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
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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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  /68

  $2,510,460 Sold Aug 06, 2025

  • 4,000 Sq Ft
  • $628/SF
  • 270 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

  53 Brooks 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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  /50

  $729,000

  • 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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  /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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  $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 $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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  /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
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  /20

  $2,300 per month

  • 2 Beds
  • 1 Bath
  • Condo 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

  525 Lake Rd Unit 4, Pine Plains, NY 12567
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  /40

  $8,350,000 Sold Jul 03, 2025

  • 5,484 Sq Ft
  • $1523/SF
  • 305 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 2023

  25 Winchell Trail, Pine Plains, NY 12567

  Stretching across the top of 29 wildflower-blanketed acres on the southern ridge of Winchell Mountain, w/commanding Catskills views, lies High View Farm. Inspired by the rolling farmland & expansive blue skies of this very special part of the Hudson Valley, the Architectural & Interior Design duo HallidayGreer collaborated with Architect Graydon Yearick & LaGuardia Design Group Landscape

  Gary DiMauro Four Seasons Sotheby's Int.

  25 Winchell Trail, Pine Plains, NY 12567
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  /2

  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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  /24

  $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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  $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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  /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
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  /14

  $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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  $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 $456,453 Not Listed For Sale

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

  272 Bean River Rd, Pine Plains, NY 12567

  272 Bean River Rd, 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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  $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 $436,112 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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  /38

  $579,000

  • 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

  540 Hicks Hill Rd, Stanfordville, NY 12581
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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 $453,116 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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  /30

  $595,000

  • 4 Beds
  • 2.5 Baths
  • 3,180 Sq Ft

  30 N Main St, Pine Plains, NY 12567

  Grand 1880 Colonial Estate Sale - Historic Fixer-Upper with Original Features and Garden Oasis Near Town CenterThis rare 1880 Grand Colonial is a dream opportunity for restoration enthusiasts and anyone searching for a historic fixer-upper near the heart of town. Situated on a flat, tree-lined lot, this estate sale is being sold as is and is filled with authentic charm—from original

  Arleen Shepley Elyse Harney Real Estate

  30 N Main St, Pine Plains, NY 12567
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  /3

  $335,000 Sold Jan 30, 2025

  • 1,296 Sq Ft
  • $258/SF
  • 53 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1950

  599 Bean River Rd, Millerton, NY 12546

  Set on a spacious 1.69-acre parcel with captivating farm and mountain views, 3 bedrooms and 2 full baths, this cozy home also includes a cozy wood-burning fireplace and hardwood floors throughout ground floor. The upper-level hosts a 2-bedroom loft space and a second full bath. With a little TLC, this property and location make it ideal for buyers looking to create their own dream home in a

  Christopher Virtuoso Keller Williams Realty HV Nort

  599 Bean River Rd, Millerton, NY 12546
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  /2

  Est $436,813 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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  $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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  /16

  Sold Jan 13, 2025

  • 1,416 Sq Ft
  • 52 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1870

  3066 Church St, Pine Plains, NY 12567

  Personalize it to your taste, as much of the groundwork has been laid for an ideal home or business. This property is situated in the H-MS (Hamlet - Main Street Zone), a tranquil area governed by a 35 MPH speed limit. The yard is flat and inviting, featuring a detached garage and an enclosed space perfect for pets or gardening.

  Brad Rebillard Dutchess Country Realty, Inc.

  3066 Church St, Pine Plains, NY 12567
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  Est $3,060,437 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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  $595,000

  • 4 Beds
  • 2 Baths
  • 2,605 Sq Ft

  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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  $2,200,000 Sold Dec 19, 2024

  • 4,207 Sq Ft
  • $523/SF
  • 377 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2023

  570 Bean River Rd, Pine Plains, NY 12567

  The approach to this spectacular contemporary barn-style home takes you up a long, winding private driveway past open fields & woods that are part of this special 22+ acre property. At the top of the hill, sits this incredibly private, recently completed, custom, stick built, 3-bedroom, 3.5-bath, contemporary home boasting approximately 4,000 sf of total square footage. This stunning home is

  Ann Stettner Neil Charles Real Estate, LLC

  570 Bean River Rd, Pine Plains, NY 12567
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  Est $638,586 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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  /11

  $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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  /16

  $62,000 Sold Nov 21, 2024

  • Land
  • 4.04 Acres
  • $15,347 per Acre

  • 133 Days On Market

  00WP Hoffman Rd, Pine Plains, NY 12567

  This BOH approved 4 acre lot has great potential to build your primary home or country home on acreage. The Approval has been extended until April of 2027 for a 3 Bedroom Dwelling. The land has a beautiful view of the Catskill mountains and is situated on a quiet town road just outside the quaint village of Pine Plains. It is in close proximity to many great places to eat visit and enjoy. Some

  Mitchell Serlin WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

  00WP Hoffman Rd, Pine Plains, NY 12567
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  /2

  Est $324,692 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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  /25

  $589,000

  • 2 Beds
  • 2 Baths
  • 1,336 Sq Ft

  618 Bean River Rd, Millerton, NY 12546

  PINE PLAINS 2-3 LOT DEVELOPMENT, 15+ acres for Family Compound or upscale development between Pine Plains Village and Millerton on quiet road off Route 199. The Development includes a 1400 SF 2BR/2BA RANCH with new well, w/2 large decks, all wood floors, wood siding + detached 2 car garage on 7+ acres subdividable into 4 acres with house and 3 acre vacant lot. Included is additional approved 8

  David Birch Barns and Farms Realty LLC

  618 Bean River Rd, Millerton, NY 12546
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  $590,000 Sold Nov 15, 2024

  • 1,643 Sq Ft
  • $359/SF
  • 19 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  7760 S Main St, Pine Plains, NY 12567

  Mid-Century Perfection This chic reimagination of a 1960 ranch with 3 bedrooms, two baths, and elegant living on one floor is move-in ready. The buyer can throw a party on the day of the closing. This rare find is a fully renovated, meticulously designed 1,788-square-foot modern home in the country. New Italian Bertazzoni stainless steel appliances including induction cook top, wall oven and

  CHRISTINE BATES William Pitt Sotheby's Int'l

  7760 S Main St, Pine Plains, NY 12567
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  Est $303,476 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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  /29

  $599,000

  • 3 Beds
  • 1.5 Baths
  • 1,862 Sq Ft

  43 Stissing Mountain Dr, Pine Plains, NY 12567

  Welcome to 43 Stissing Mountain Drive — a peaceful and private retreat set on 2 beautifully wooded acres in the heart of the Hudson Valley. This great contemporary home offers 3 bedrooms and 2 bathrooms across 1,862 square feet of comfortable living space. With an open-concept layout, cathedral ceilings, and abundant natural light, the home blends style and function. A cozy fireplace anchors the

  Richard Brenner Rich Brenner Realty, LLC

  43 Stissing Mountain Dr, Pine Plains, NY 12567

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