Homes for Sale near Stissing Mountain High School

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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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  Explore Stissing Mountain High School

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  /5

  $949,000

  • 4 Beds
  • 2.5 Baths
  • 2,380 Sq Ft

  Beilke Road Beilke Rd, Millerton, NY 12546

  4 Bedroom 3 Bath Barn style home To Be Built on 21 acre hilltop property in the town of Northeast bordering the Village of Millerton. Super energy efficient home with low cost heat pump technology that will provide heating and cooling. Geo thermal and Solar are also possibilities for this home. 21 acre parcel residential zoning allows for further sub-division if buyer wishes to do so. A current

  

  Brad Rebillard

  DUTCHESS COUNTRY REALTY INC. M

  (518) 864-1527

  Beilke Road Beilke Rd, Millerton, NY 12546
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  /10

  $229,000

  • Land
  • 5 Acres
  • $45,800 per Acre

  0 Smithfield Rd Unit KEY879008, North East, NY 12546

  An exceptional location! This Smithfield Road setting is a combination of open meadow, with extraordinary vistas of the splendid pastoral countryside, light woodland and a patch that is overgrown. The potential increases enormously with a careful thinning of the excessive weeds etc. With 5 acres that is BOHA your dream home is much closer to a reality. This place is heaven on

  

  Larry Havens

  Havens Real Estate

  (518) 594-8105

  0 Smithfield Rd Unit KEY879008, North East, NY 12546
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  /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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  /26

  $379,000

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

  48 Woodside St, Pine Plains, NY 12567

  Whether for starting out retirement or weekend use, 48 Woodside Street is an efficient, move-in-ready home. Pine Plains offers a number of attractions from fine dining at the Stissing House, or a relaxing kayak paddle on Thompson Pond. Nearby hiking trails offer options such as the Stissing Fire Tower, a challenging local favorite, and the Thompson Preserve an easy woodland stroll around a

  

  Brad Rebillard

  Dutchess Country Realty, Inc.

  (518) 662-5219

  48 Woodside St, Pine Plains, NY 12567
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  /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
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  /38

  $559,000 Open Sun 12PM - 2PM

  • 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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  /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
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  /50

  $849,000

  • 4 Beds
  • 3.5 Baths
  • 2,345 Sq Ft

  172 Shields Rd, Red Hook, NY 12571

  Set along a quiet, picturesque dirt road, this private escape delivers the kind of peace you didn’t know you needed—until now. A wide, grassy yard flows to a meandering stream, while a heated saltwater pool turns every day into a vacation. Whether you're seeking a full-time sanctuary or a weekend retreat, this home strikes the perfect balance between comfort, privacy, and style.Inside,

  

  Michael Kahns

  Compass Greater NY, LLC

  (845) 640-5219

  172 Shields Rd, Red Hook, NY 12571
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  /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
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  /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
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  /29

  $1,475,000

  • 4 Beds
  • 4.5 Baths
  • 3,090 Sq Ft

  36 Market Ln, Clinton Corners, NY 12514

  Originally built in 1836, this beautifully renovated Federal-style farmhouse is rich with history and character, once part of the Underground Railroad and also used as a Quaker meeting hall. Set on over four acres with Willow Brook meandering through, this one-of-a-kind property offers a peaceful, storied setting with modern comfort woven throughout.Inside, original wide board floors,

  PATRICIA HINKEIN Patricia A. Hinkein Realty

  36 Market Ln, Clinton Corners, NY 12514
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  /35

  $899,000

  • 3 Beds
  • 3 Baths
  • 2,450 Sq Ft

  5 Willow Brook Ridge, Clinton Corners, NY 12514

  Set down a long private drive, this classic cape cod style home offers exceptional privacy on a 5 acre wooded lot within a beautiful residential pocket just 15 minutes from Rhinebeck Village. A true retreat, the property offers multiple outdoor areas of enjoyment including a large heated, gunite pool, rear deck, front porch, and expansive lawn.Wide plank pine wood floors flow throughout

  Jonathan Berry Upstate Down

  5 Willow Brook Ridge, Clinton Corners, NY 12514
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  /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
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  /26

  $935,000

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft

  420 Roche Dr, Ancramdale, NY 12503

  Set in the historic farming community of Ancram, this picture-perfect Cape sits gracefully on 20 pastoral acres surrounded by protected farmland. With timeless curb appeal, the home is complemented by a classic barn with two stalls and an oversized detached two-car garage, ideal for equestrian or hobby farm enthusiasts.A wraparound front porch evokes the charm of traditional farmhouse living,

  Jill Rose Houlihan Lawrence Inc.

  420 Roche Dr, Ancramdale, NY 12503
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  /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
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  /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
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  /36

  $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 farmhouse combines historical character with contemporary amenities, featuring gleaming wood and wide board floors beamed ceiling, stone fireplace, central air and a gourmet

  Jeannine Simmons Corcoran Country Living

  235 Knob Hill Rd, Stanfordville, NY 12581
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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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  /49

  $1,200,000

  • 3 Baths
  • 4,000 Sq Ft

  573 E Kerley Corners Rd, Elizaville, NY 12523

  Welcome to the Elizaville Diner & Deli, a Hudson Valley roadside treasure with a lakeside backdrop. Set on just over two picturesque acres, this mixed-use commercial property includes a restored vintage diner, a renovated deli, ample parking, and grassy fields overlooking a spring-fed quarry.Originally built in 1956, the Elizaville Diner is the last surviving example of a Kullman Dutchess

  Shaina Marron Houlihan Lawrence Inc.

  573 E Kerley Corners Rd, Elizaville, NY 12523
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  /43

  $1,345,000

  • 5 Beds
  • 7 Baths
  • 6,318 Sq Ft

  88 Hunns Lake Rd, Stanfordville, NY 12581

  This is Bullis Hall, the circa 1800’s Greek Revival landmark in the picturesque and historic hamlet of Bangall in Stanford, NY. The Hudson Valley, Dutchess County property is situated with excellent street frontage on Hunns Lake Road just off Route 82. With over 6,000 square feet, the building is ready for its next steward; a blank canvas for future use. Bangall is one of many hamlets in the

  Steve Bruman Corcoran Country Living

  88 Hunns Lake Rd, Stanfordville, NY 12581
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  /8

  $895,000 Coming Soon

  • 1 Bed
  • 2 Baths
  • 1,200 Sq Ft

  283 Willow Glen Rd, Red Hook, NY 12571

  Tucked into the woods on three completely private acres, this architecturally striking, custom-built retreat is more than just a home — it’s an experience. Constructed with steel and glass, the design invites nature in at every turn, with clean lines, floor-to-ceiling windows, and a seamless indoor-outdoor connection that transforms with the seasons. The main level offers an open, sun-filled

  Lindsay Rothman Compass Greater NY LLC

  283 Willow Glen Rd, Red Hook, NY 12571
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  /25

  $940,000

  • 5 Beds
  • 3.5 Baths
  • 5,650 Sq Ft

  19 Friendship Ln, Red Hook, NY 12571

  Welcome to your private oasis and come enjoy this 3 bedroom 2.5 bath Colonial situated on 5 plus acres. The home also features an in law unit above the garage which has 2 additional bedrooms, a full bathroom, a galley kitchen and open living room. The home is very close to the Taconic State Parkway and US Rte 199 making it an easy drive to anywhere. The town of Red Hook boasts vibrant shops

  Jeffery Dolfinger Century 21 Hudson Valley Rlty.

  19 Friendship Ln, Red Hook, NY 12571
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  /21

  $325,000

  • Land
  • 13.66 Acres
  • $23,792 per Acre

  TBD Cold Spring Rd, Clinton Corners, NY 12514

  Large wooded lot on Cold Spring Road - 13.66 acres. Drive along soft rolling hills on beautiful and quiet Cold Spring Road dotted with farmhouses and horse pastures. The picturesque road leads to an ample secluded lot on which to design your dream home with plenty of room to spare. Turn this beautiful private blank canvas into a private oasis. Rockwalls mark off the upper border. Electric is

  Shana Altstaetter Halter Associates Realty Inc

  TBD Cold Spring Rd, Clinton Corners, NY 12514
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  /36

  $12,000,000

  • 5 Beds
  • 3.5 Baths
  • 6,340 Sq Ft

  118 Finkle Rd, Ancramdale, NY 12503

  Set among the beautiful rolling hills on 203 acres is this private estate that takes you back in time. The farm was built in 2008 around a c.1754 Dutch barn that was dismantled from upstate NY and transformed into an incredible great room with 34' soaring ceilings, a brick fireplace and two huge French doors to take in the view. Designed by Cynthia Filkoff with 6,340 square feet, the main house

  Paula Redmond Corcoran Country Living - Mill

  118 Finkle Rd, Ancramdale, NY 12503
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  /15

  $325,000

  • Land
  • 13.66 Acres
  • $23,792 per Acre

  Tbd Cold Spring Rd, Red Hook, NY 12571

  Large wooded lot on Cold Spring Road - 13.66 acres. Drive along soft rolling hills on beautiful and quiet Cold Spring Road dotted with farmhouses and horse pastures. The picturesque road leads to an ample secluded lot on which to design your dream home with plenty of room to spare. Turn this beautiful private blank canvas into a private oasis. Rockwalls mark off the upper border. Electric is

  Shana Altstaetter Halter Associates Realty

  Tbd Cold Spring Rd, Red Hook, NY 12571
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  /22

  $480,000

  • 3 Beds
  • 2 Baths
  • 2,068 Sq Ft

  106 Tick Tock Way, Stanfordville, NY 12581

  Set on 1.8 wooded acres in the quaint hamlet of Stanfordville, 106 Tick Tock offers an ideal blend of charm and privacy in a convenient location. Surrounded by mature trees, the home feels wonderfully secluded. Its appeal is enhanced by an old stone wall and an upper lawn with Adirondack chairs, ideal for relaxing outdoors.The main level of the home features an open-concept layout and

  Kelcey Otten Compass Greater NY, LLC

  106 Tick Tock Way, Stanfordville, NY 12581
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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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  /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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  /15

  $325,000

  • Land
  • 3.4 Acres
  • $95,588 per Acre

  Lot #2 Church Rd, Red Hook, NY 12571

  Beautiful 3.4 Acre Lot in Red Hook, NY – Ready for Your Dream Home! Located off Jackson Corners Rd, just minutes from both Red Hook and Pine Plains, this stunning 3.4 acre property is the perfect spot to build your dream home. Septic installed for a 3 bed approved home. Nestled in a private, cleared area off Church Road, the land features a level building pad, pond, a cleared patio adding

  Bryn Bahnatka Dier BHHS Hudson Valley Properties

  Lot #2 Church Rd, Red Hook, NY 12571
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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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  /5

  $130,000

  • Land
  • 0.88 Acre
  • $147,727 per Acre

  20 Pine Rd, Livingston, NY 12523

  Beautiful, building lot, just under an acre waiting for you to build, camp or buy now and decide later! Road frontage on both PINE RD & FIELD RD. Electric, Well & Septic already in!! Quiet setting cleared building area already done with mature trees scattered around, this property holds incredible promise. Don't miss this rare opportunity to own a peaceful slice of the Hudson Valley. PLUS,

  Margaret Bower Avenia Columbia County RE Specialist

  20 Pine Rd, Livingston, NY 12523
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  /38

  $765,000

  • 3 Beds
  • 2 Baths
  • 2,030 Sq Ft

  21 Pine Knoll Ln, Clinton Corners, NY 12514

  Nestled at the end of a long, private drive, this single-level retreat set on 5 wooded acres offers exceptional privacy surrounded by a beautiful natural setting. Located just 15 minutes from Rhinebeck Village, this renovated cedar-sided home features lovely outdoor areas including a screened-in porch, large deck and a heated lap pool.The bright and airy living area welcomes you with

  Hailey Kiesewetter Upstate Down

  21 Pine Knoll Ln, Clinton Corners, NY 12514
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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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  /38

  $445,000

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  5760 Route 82, Clinton Corners, NY 12514

  Discover the potential of tranquil living at 5760 Route 82 in Clinton Corners. This 3-bedroom, 2-full bath raised ranch is set on over 5 private acres with a long driveway offering peace, privacy, and space to grow. This home has been beautifully renovated with all new kitchen appliances, new floors, new deck, updated bathrooms. The attached two-car garage adds functionality, while the 5 plus

  Alan Amerman Coldwell Banker Realty

  5760 Route 82, Clinton Corners, NY 12514
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  /37

  $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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  /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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  /7

  $65,000

  • Land
  • 1.08 Acres
  • $60,185 per Acre

  0 Beaver (Jackson Crs) Rd Unit 20253422, Gallatin, NY 12571

  Just over an acre of wooded land waiting for you to build your dream home. The property includes 184 feet of frontage on Jackson Corners Rd. The nearby Roeliff Jansen Kill provides some of the best trout fishing in the northeast as well as numerous swimming holes. Conveniently located near the Taconic State Parkway as well as all the amenities in Rhinebeck, Red Hook and Hudson.Please note

  Joel Craig Coldwell Banker Village Green

  0 Beaver (Jackson Crs) Rd Unit 20253422, Gallatin, NY 12571
• 

  

  /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
• 

  

  /20

  $375,000

  • 3 Beds
  • 2 Baths

  107 Creamery Rd, Stanfordville, NY 12581

  Opportunity awaits in Stanfordville! This legal 3 family home offers great potential. The property features a 2 bed, 1 bath unit on the second floor, a spacious 1 bed, 1 bath unit on the main level, and a studio apartment in the walk out basement. Situated on a quaint country road with plenty of off-street parking, this is an ideal investment or owner occupied opportunity.

  Carol Mahoney Real Broker NY LLC

  107 Creamery Rd, Stanfordville, NY 12581

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