Pine Plains, NY Homes

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  /50

  $3,495,000

  • 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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  /50

  $2,760 - $2,940 per month

  Stissing Farms

  2 Beds

  51 Hillside Rd, Pine Plains, NY 12567

  Discover effortless living at Stissing Farms Townhomes, where modern comfort meets small-town charm. These beautifully designed homes feature open floor plans, two spacious bedrooms, two full baths, full basements, and two car parking (one garage, one driveway)thoughtfully crafted for both style and convenience. Enjoy high ceilings, modern kitchens, in-unit laundry, central air, and a private

  51 Hillside Rd, Pine Plains, NY 12567
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  $415,000 Sold Oct 14, 2025

  1601 Route 199, Red Hook, NY 12571

  • 3 Beds
  • 2 Baths
  • 1,097 Sq Ft
  • Built 1972

  Last Sold Summary

  • 3% Below List Price
  • $378/SF
  • 30 Days On Market

  Current Estimated Value $437,000

  Last Listing Agent Jason Schobert eXp Realty

  1601 Route 199, Red Hook, NY 12571
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  Est $1,677,672 Not Listed For Sale

  454 Bean River Rd, Pine Plains, NY 12567

  454 Bean River Rd, Pine Plains, NY 12567

  Last Sold Summary

  • 11% Below List Price
  • 194 Days On Market

  • Last Sold Price $1,895,000
  • Dec 18, 2023

  Last Listing Agent PAULA REDMOND Corcoran Country Living
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  /35

  $899,900

  • 3 Beds
  • 2.5 Baths
  • 2,352 Sq Ft

  521 Hall Hill Rd Unit 18, Ancram, NY 12502

  OPEN HOUSE: Saturday, April 18th 1:00-3:00 p.m. This home is perfect for entertaining, with multiple indoor and outdoor spaces. The custom-designed kitchen, complete with an ice maker, two separate ovens, and a gas stove, is ideal for hosting large holiday gatherings. The open living room and kitchen layout make it easy for conversation to flow. Upstairs, you'll find three oversized bedrooms,

  

  Tracy Boomhower

  Country Views Realty, Inc.

  (518) 299-5749

  521 Hall Hill Rd Unit 18, Ancram, NY 12502
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  /15

  $2,850 per month

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Townhouse for Rent

  59 Hillside Rd, Pine Plains, NY 12567

  Discover effortless living at Stissing Farms Townhomes, where modern comfort meets small-town charm. These beautifully designed homes feature open floor plans, two spacious bedrooms, two full baths, full basements, and one-car garages—thoughtfully crafted for both style and convenience. Enjoy high ceilings, modern kitchens, in-unit laundry, central air, and a private ensuite primary bath that

  MICHELLE FRANCESE Corcoran Country Living

  59 Hillside Rd, Pine Plains, NY 12567
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  /13

  $924,500 Sold Aug 07, 2025

  Tbd Woods Dr, Ancramdale, NY 12503

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

  Last Sold Summary

  • 5% Below List Price
  • 113 Days On Market

  Last Listing Agent Arlena Armstrong Anatole House LLC

  Tbd Woods Dr, Ancramdale, NY 12503
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  /38

  Est $2,021,307 Not Listed For Sale

  88 Friar Tuck Rd, Ancramdale, NY 12503

  • 6 Beds
  • 3.5 Baths
  • 3,804 Sq Ft
  • Built 1880

  88 Friar Tuck Rd, Ancramdale, NY 12503

  Last Sold Summary

  • 1% Above List Price
  • $526/SF
  • 202 Days On Market

  • Last Sold Price $2,000,000
  • Dec 19, 2024

  Last Listing Agent Ann Simmons Compass Greater NY, LLC d/b/a
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  /23

  $665,000

  • 7 Beds
  • 5 Baths
  • 3,500 Sq Ft

  80 County Route 7, Pine Plains, NY 12567

  This beautifully updated legal 2-family home seamlessly blends vintage charm with modern convenience, offering exceptional flexibility for multigenerational living, rental income, or guest accommodations. Located just 7 minutes from Pine Plains Village and set on a scenic lot with sweeping countryside views and a neighboring 200-acre farm, the property features meticulously maintained grounds,

  

  Margaret Mondello

  Margaret Mondello Real Estate

  (518) 608-3993

  80 County Route 7, Pine Plains, NY 12567
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  /28

  $12,000 per month

  • 4 Beds
  • 4 Baths
  • 3,029 Sq Ft
  • House for Rent

  231 Lake Rd, Pine Plains, NY 12567

  Ideal Summer Retreat. This 4 bedroom (all ensuite), is a perfect blend of chic furnishings and modern conveniences, located in a quiet lakeside community in the heart of Pine Plains but also removed and private. A stones-throw away from Stissing Pond, where you can swim, launch SUP’s and go fishing for trophy Bass, or take a leisurely bike ride around the lake, 3-5 mile loop (local traffic

  CATHERINE HOWARD Corcoran Country Living

  231 Lake Rd, Pine Plains, NY 12567
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  $4,970,000 Sold Mar 09, 2026

  310 Carpenter Hill Rd, Pine Plains, NY 12567

  • 5 Beds
  • 5.5 Baths
  • 6,310 Sq Ft
  • Built 1993

  Last Sold Summary

  • 11% Below List Price
  • $788/SF
  • 239 Days On Market

  Current Estimated Value $2,948,116

  Last Listing Agent PAULA REDMOND Corcoran Country Living

  310 Carpenter Hill Rd, Pine Plains, NY 12567
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  /2

  Est $557,568 Not Listed For Sale

  7795 S Main St, Pine Plains, NY 12567

  • Studio
  • 4,032 Sq Ft
  • Built 1979

  7795 S Main St, Pine Plains, NY 12567

  Last Sold Summary

  • 14% Below List Price
  • $121/SF

  • Last Sold Price $489,000

  Last Listing Agent Jo-Ann Campagiorni
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  /34

  $4,495,000

  • 7 Beds
  • 4 Baths
  • 5,481 Sq Ft

  8032-8060 New York 82, Pine Plains, NY 12567

  Cedar Ridge Farm is a premier 246-acre equestrian estate set in the heart of Dutchess County, offering exceptional land quality, extensive infrastructure, and the rare scale required for a top tier equestrian operation or private country estate. The farm encompasses approximately 110 acres of fenced paddocks supported by thoughtfully designed facilities that ensure efficiency, functionality, and

  George Langa Houlihan Lawrence Inc.

  8032-8060 New York 82, Pine Plains, NY 12567
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  /17

  $2,250 per month

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

  3004 W Church St Unit Cottage, Pine Plains, NY 12567

  Fully renovated two-bedroom cottage in the hamlet of Pine Plains, offering the convenience of in-town living just steps from the center of this charming Hudson Valley community. The home features a bright, welcoming interior with an updated kitchen and bath, two well-proportioned bedrooms, and the convenience of an in-home washer and dryer. Modern updates throughout blend cottage charm with

  Jennifer Enloe Four Seasons Sotheby's Int.

  3004 W Church St Unit Cottage, Pine Plains, NY 12567
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  $390,000 Sold Aug 11, 2025

  285 South Rd, Stanfordville, NY 12581

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

  Last Sold Summary

  • 18% Below List Price
  • 54 Days On Market

  Current Estimated Value $391,380

  Last Listing Agent Michael Tellerday Houlihan Lawrence Inc.

  285 South Rd, Stanfordville, NY 12581
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  Not Listed For Sale

  7604 Route 82, Pine Plains, NY 12567

  • 5 Beds
  • 3.5 Baths
  • 3,712 Sq Ft
  • Built 1970

  7604 Route 82, Pine Plains, NY 12567

  Last Sold Summary

  • $131/SF
  • 346 Days On Market

  • Last Sold Price $485,000
  • Jun 02, 2023

  Last Listing Agent MICHELLE FRANCESE Corcoran Country Living
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  /36

  $1,499,000 Pending

  • 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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  /19

  $5,500 per month

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

  156 County Route 7, Pine Plains, NY 12567

  All you can say when entering The Barn is AMAZING! Converted 1800's three level barn with original beams and reclaimed wood for flooring and elsewhere. The dramatic open living room and dining areas have walls of glass and soaring ceilings. The upper floor is an open bedroom suite with space for an office, sitting area and has an outside balcony. There is geothermal radiant heat and A/C.

  ANN SIMMONS Compass Greater NY, LLC

  156 County Route 7, Pine Plains, NY 12567
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  /12

  $55,000 Sold Oct 27, 2025

  0 County Route 8 Unit 20252154, Gallatin, NY 12567

  • Land
  • 1.1 Acres
  • $50,000 per Acre

  Last Sold Summary

  • 15% Below List Price
  • 46 Days On Market

  Last Listing Agent Joel Craig Coldwell Banker Village Green

  0 County Route 8 Unit 20252154, Gallatin, NY 12567
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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

  Last Sold Summary

  • 69 Days On Market

  • Last Sold Price $28,000
  • Dec 29, 2023

  Last Listing Agent Melissa Vooris Past Member
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  /26

  $4,250,000

  • 6 Beds
  • 5 Baths
  • 6,146 Sq Ft

  468 Tripp Rd, Pine Plains, NY 12567

  We welcome this 1834 restored farm into our Luxury Collection of Hudson Valley properties. This magnificent property makes the perfect country compound. Completely updated, restored and improved to also include a new addition on the main house. This 200 acre farm has all the privacy and beauty of a true country retreat. With such amenities as a converted dairy barn to an indoor tennis court

  George Langa Houlihan Lawrence Inc.

  468 Tripp Rd, Pine Plains, NY 12567
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  /15

  $2,610 per month

  • 2 Beds
  • 2 Baths
  • 1,147 Sq Ft
  • Townhouse for Rent

  32 Town Centre Rd, Pine Plains, NY 12567

  Discover effortless living at Stissing Farms Townhomes, where modern comfort meets small-town charm. These beautifully designed homes feature open floor plans, two spacious bedrooms, two full baths, full basements, and one-car garages—thoughtfully crafted for both style and convenience. Enjoy high ceilings, modern kitchens, in-unit laundry, central air, and a private ensuite primary bath that

  MICHELLE FRANCESE Corcoran Country Living

  32 Town Centre Rd, Pine Plains, NY 12567
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  $270,000 Sold Jan 08, 2026

  34 Myrtle Ave, Pine Plains, NY 12567

  • 5 Beds
  • 2.5 Baths
  • 2,100 Sq Ft
  • Built 1900

  Last Sold Summary

  • 7% Below List Price
  • $129/SF
  • 17 Days On Market

  Current Estimated Value $280,362

  Last Listing Agent Blake Michaud BHHS Hudson Valley Properties

  34 Myrtle Ave, Pine Plains, NY 12567
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  Not Listed For Sale

  0 County Route 7 Unit 144952, Pine Plains, NY 12567

  0 County Route 7 Unit 144952, Pine Plains, NY 12567

  Last Sold Summary

  • 659 Days On Market

  • Last Sold Price $809,000
  • Nov 01, 2024

  Last Listing Agent Ann Simmons Compass Greater NY, LLC d/b/a
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  /40

  $1,575,000

  • 3 Beds
  • 3 Baths
  • 2,433 Sq Ft

  617 Bean River Rd, Pine Plains, NY 12567

  Experience this stunning sanctuary where rustic charm meets modern luxury on over 19 meticulously manicured acres of pure magic! This elevated 3-bedroom, 3-bath masterpiece captures your heart the moment you arrive, drawing you toward an expansive wood deck and a stunning screened-in gazebo with a built-in fire-pit - the ultimate "entertainment perch" for soaking in breathtaking, panoramic valley

  Diana Bisselle William Pitt Sotheby's Int'l

  617 Bean River Rd, Pine Plains, NY 12567
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  /15

  $2,750 per month

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft
  • Townhouse for Rent

  20 Town Centre Rd, Pine Plains, NY 12567

  Discover effortless living at Stissing Farms Townhomes, where modern comfort meets small-town charm. These beautifully designed homes feature open floor plans, two spacious bedrooms, two full baths, full basements, and one-car garages—thoughtfully crafted for both style and convenience. Enjoy high ceilings, modern kitchens, in-unit laundry, central air, and a private ensuite primary bath that

  MICHELLE FRANCESE Corcoran Country Living

  20 Town Centre Rd, Pine Plains, NY 12567
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  /49

  $545,000 Sold Mar 03, 2026

  1301 County Route 7, Ancram, NY 12502

  • 3 Beds
  • 3 Baths
  • 2,184 Sq Ft
  • Built 1894

  Last Sold Summary

  • 13% Below List Price
  • $250/SF
  • 112 Days On Market

  Current Estimated Value $570,586

  Last Listing Agent Anthony D'Argenzio Houlihan Lawrence Inc.

  1301 County Route 7, Ancram, NY 12502
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  Not Listed For Sale

  0 Dewitt Ln Unit KEYM418621, Ancramdale, NY 12503

  • 4 Beds
  • 3 Baths
  • 4,144 Sq Ft
  • Built 2000

  0 Dewitt Ln Unit KEYM418621, Ancramdale, NY 12503

  Last Sold Summary

  • $477/SF
  • 428 Days On Market

  • Last Sold Price $1,975,000
  • Mar 17, 2025

  Last Listing Agent Neil Charles Neil Charles Real Estate, LLC
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  /37

  $1,225,000 Pending

  • 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
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  /17

  $2,850 per month

  • 2 Beds
  • 1 Bath
  • 1,232 Sq Ft
  • House for Rent

  119 Righters Corners Rd, Pine Plains, NY 12567

  Welcome to 119 Righters Corners Rd, a charming and well-maintained two-bedroom, one-bathroom home located in the scenic Town of Pine Plains, New York. This inviting residence features hardwood floors throughout, creating a warm and cohesive living space. The kitchen and bathroom have been tastefully renovated, offering modern finishes while maintaining the home’s comfortable, classic feel. The

  Richard Brenner Rich Brenner Realty, LLC

  119 Righters Corners Rd, Pine Plains, NY 12567
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  $2,153,550 Sold Mar 04, 2026

  820 Cold Spring Rd, Stanfordville, NY 12581

  • 3 Beds
  • 2.5 Baths
  • 2,267 Sq Ft
  • Built 2025

  Last Sold Summary

  • 8% Above List Price
  • $950/SF
  • 166 Days On Market

  Last Listing Agent DOUG MAXWELL Upstate Modernist

  820 Cold Spring Rd, Stanfordville, NY 12581
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  Not Listed For Sale

  0 Hill Top Rd Unit ONEH6333617, Gallatin, NY 12502

  0 Hill Top Rd Unit ONEH6333617, Gallatin, NY 12502

  Last Sold Summary

  • 85 Days On Market

  • Last Sold Price $370,000
  • Apr 07, 2025

  Last Listing Agent Andrew Gates Houlihan Lawrence Inc.
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  /39

  $3,995,000

  • 10 Beds
  • 6.5 Baths
  • 6,994 Sq Ft

  1515-1517 County Road 83, Pine Plains, NY 12567

  Set far back from one of the Hudson Valley’s most prestigious and scenic roads, this stunningly restored 1830s colonial farmhouse is a masterclass in combining historic charm with sophisticated living. Situated in the heart of the pastoral Shekomeko Valley on just under 10 pristine acres, this property offers ultimate privacy surrounded by large, rolling farms and protected acreage. Classic white

  OLIVER BROWN Houlihan Lawrence Inc.

  1515-1517 County Road 83, Pine Plains, NY 12567
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  $732,000 Sold Oct 09, 2025

  546 Hicks Hill Rd, Stanfordville, NY 12581

  • 3 Beds
  • 2.5 Baths
  • 2,971 Sq Ft
  • Built 2003

  Last Sold Summary

  • $246/SF
  • 33 Days On Market

  Current Estimated Value $734,342

  Last Listing Agent Joseph Iannibelli Keller Williams NY Realty

  546 Hicks Hill Rd, Stanfordville, NY 12581
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  Not Listed For Sale

  0 Hill Top Rd Unit 155018, Gallatin, NY 12502

  0 Hill Top Rd Unit 155018, Gallatin, NY 12502

  Last Sold Summary

  • 85 Days On Market

  • Last Sold Price $370,000
  • Apr 07, 2025

  Last Listing Agent Andrew Gates Houlihan Lawrence, Inc.
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  /36

  $2,600,000

  • 3 Beds
  • 3.5 Baths
  • 4,247 Sq Ft

  3778 New York 82, Ancramdale, NY 12503

  Set up a hillside on over 76 acres, this architectural gem looks over a magnificent valley nestled in gentle rolling hills, meadows and woodlands with views to distant mountains. It's a private artist's retreat and gardener's dream and on the market for the first time in over 35 years. The overall design was conceived by the owner/architect Sam Brody, FAIA, for his family and features a 4,250 SF

  Michael Stasi Corcoran Country Living

  3778 New York 82, Ancramdale, NY 12503
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  $290,000 Sold Jun 30, 2025

  15 Ferris Ln, Red Hook, NY 12571

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

  Last Sold Summary

  • 11% Below List Price
  • 91 Days On Market

  Last Listing Agent PAULA REDMOND Corcoran Country Living

  15 Ferris Ln, Red Hook, NY 12571
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  Est $3,020,699 Not Listed For Sale

  420 Carpenter Hill Rd, Pine Plains, NY 12567

  • 6 Beds
  • 4.5 Baths
  • 5,163 Sq Ft
  • Built 1996

  420 Carpenter Hill Rd, Pine Plains, NY 12567

  Last Sold Summary

  • 12% Below List Price
  • $663/SF
  • 162 Days On Market

  • Last Sold Price $3,425,000
  • Apr 16, 2025

  Last Listing Agent LINDSAY BALDWIN Houlihan Lawrence Inc.
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  /34

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,635 Sq Ft

  3838 Route 199, Pine Plains, NY 12567

  Sweet and solid, one level Ranch home on a bucolic setting with rolling hills and farmland framing your homestead. Walk into your open living room with built ins and lovely bay window. Through to the dining room and eat in kitchen, perfect for hosting with ease. Sliders to the back covered porch off the dining room allows for al fresco living and enjoying your coffee while watching the sunrise.

  Chelsea Pollard-Seiler Mondello Upstate Properties

  3838 Route 199, Pine Plains, NY 12567
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  $820,000 Sold Jan 16, 2026

  1388 Route 83, Pine Plains, NY 12567

  • 4 Beds
  • 4.5 Baths
  • 3,000 Sq Ft
  • Built 1880

  Last Sold Summary

  • 11% Below List Price
  • $273/SF
  • 169 Days On Market

  Current Estimated Value $802,978

  Last Listing Agent Jill Rose Houlihan Lawrence Inc.

  1388 Route 83, Pine Plains, NY 12567

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