Homes for Sale near Stissing Mountain High School

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  /50

  $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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  Explore 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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  /7

  $229,000

  • Land
  • 5.00 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 earth.Away from the

  

  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
  • 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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  /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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  /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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  /50

  $1,100,000

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

  225 Simons Rd, Ancram, NY 12502

  Peace and privacy are what you will find at this secluded country retreat nestled on 24.56 bucolic acres just outside the quiet community of Ancram. Surrounded by abundant birds and wildlife, with distant views of the Berkshire Mountains, this small farm compound is perfect for someone dreaming of homesteading, or just a weekend getaway. The contemporary wood and stone residence features an open

  Dana Duncan Houlihan Lawrence Inc.

  225 Simons Rd, Ancram, NY 12502
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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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  /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

  172 Shields Rd, Red Hook, NY 12571
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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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  /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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  /22

  $825,000

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft

  1104 Cold Spring Rd, Clinton Corners, NY 12514

  Discover a rare opportunity with these two separate expansive lots totaling 78.4 acres, less than 2 hours from NYC. Turn right on to the Taconic and be in NYC in less than 2 hours. Winding gated driveway leads to the A-Frame house, and another driveway leads to a pond site and an open field. Excellent development opportunity with cleared areas, pond sites, wetlands, roads and utilities in place,

  Shana Altstaetter Halter Associates Realty Inc

  1104 Cold Spring Rd, Clinton Corners, NY 12514
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  /30

  $825,000

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft

  1104 Cold Spring Rd, Red Hook, NY 12571

  Discover a rare opportunity with these two separate expansive lots totaling 78.4 acres, less than 2 hours from NYC. Turn right on to the Taconic and be in NYC in less than 2 hours. Winding gated driveway leads to the A-Frame house, and another driveway leads to a pond site and an open field. Excellent development opportunity with cleared areas, pond sites, wetlands, roads and utilities in place

  Shana Altstaetter Halter Associates Realty

  1104 Cold Spring Rd, Red Hook, NY 12571
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  /3

  $949,000

  • 4 Beds
  • 2.5 Baths
  • 4,670 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

  Beilke Road Beilke Rd, Millerton, NY 12546
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  /38

  $775,000

  • 4 Beds
  • 2 Baths
  • 1,344 Sq Ft

  1220 Hunns Lake Rd, Pine Plains, NY 12567

  1220 Hunns Lake Rd is perfect as a full-time family home or a weekend escape, ideally located for both tranquility and convenience. This charming early 1900's farmhouse in the serene Shekomeko Valley offers 4 bedrooms, 2 bathrooms, and 1,344 square feet on 1.52 bucolic acres. The property boasts views of the surrounding countryside and stunning sunsets. Enter the home through the light-drenched

  Marina Tatistcheff Compass Greater NY, LLC

  1220 Hunns Lake Rd, 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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  /35

  $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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  /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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  /40

  $1,350,000

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft

  1705 County Route 19, Elizaville, NY 12523

  1705 County Route 19, Clermont, NYWelcome to a truly special slice of the Hudson Valley—where history, nature, and craftsmanship meet in perfect harmony.Set on over 20 secluded acres, this warm and welcoming log home offers a lifestyle rooted in nature and rich with story. Once the site of an original gristmill, the property is bordered by the Roeliff Jensen Kill, a vibrant waterway

  Doreen De Carolis Upstate Down

  1705 County Route 19, Elizaville, NY 12523
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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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  /38

  $795,000

  • 3 Beds
  • 2 Baths
  • 3,688 Sq Ft

  119 W Hunns Lake Rd, Stanfordville, NY 12581

  When you pull your gaze away from the swans gliding on the pristine 64-acre lake that completely fills the view through the wall of windows across the front of this home, you will discover 3600+ square feet of single level living space with cottage core interior charm. Whether you prefer swimming, kayaking, paddle boarding, or just taking in the view, this is vacation living every day of the

  Susan Whalen George T Whalen Real Estate

  119 W Hunns Lake Rd, Stanfordville, NY 12581
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  /93

  $1,500,000

  • 3 Beds
  • 2.5 Baths
  • 3,193 Sq Ft

  1606 Bulls Head Rd, Clinton Corners, NY 12514

  OPEN HOUSE Sunday, July 27 from 11-2. Built circa 1790, this idyllic, 3193 square foot home is the country oasis you have been seeking. Only 1 3/4 hours from NYC, swim in your private pond, stroll through your private woods and relax in the peacefulness of this charming Hudson Valley homestead. With 3 (possibly 4) bedrooms, 2 1/2 bathrooms, a formal dining room and the very large, original

  Richard Byrne Four Seasons Sotheby's Int.

  1606 Bulls Head Rd, Clinton Corners, NY 12514
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  /30

  $785,000

  • 2 Beds
  • 1 Bath
  • 1,120 Sq Ft

  39 Willow Ln, Clinton Corners, NY 12514

  This property paints a truly serene picture of a nature-filled escape, with endless potential for both full-time living or a weekend retreat. The 87-acre wooded property offers the perfect balance of privacy and natural beauty, with a large pond, wildlife, and a trail for exploring. Bring your horses and with proper permitting, turn this into a possible animal sanctuary. Two dwellings— a primary

  DEBORAH LAPOINTE Exit Realty Connections

  39 Willow Ln, Clinton Corners, NY 12514
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  /36

  $798,000

  • 3 Beds
  • 2 Baths
  • 1,890 Sq Ft

  6392 Route 82, Stanfordville, NY 12581

  Looking for a small farmhouse with abundant land in Dutchess County? This circa 1883 house on a 67-acre lot would be a wonderful place for all your outdoor activities, a place to spread out and explore. Lovely meadows along the road surround the early farmhouse, an old railroad trestle divides the lower meadows, and then the land rises to enchanting woodlands. A series of trails wind through the

  Susan Whalen George T Whalen Real Estate

  6392 Route 82, Stanfordville, NY 12581
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  /36

  $895,000

  • 3 Beds
  • 2.5 Baths
  • 2,548 Sq Ft

  294 Creamery Rd, Stanfordville, NY 12581

  Privately situated off a quiet country road in the Town of Stanford, midway between Millbrook and Rhinebeck, is this log home on 4.9 acres. It offers a unique blend of rustic charm, modern comfort and a deep connection with nature. The home fits perfectly into its surroundings, nestled in the midst of meadows, woodlands, a stream and an abundance of wildlife. The home has a wonderful covered

  Susan Whalen George T Whalen Real Estate

  294 Creamery Rd, Stanfordville, NY 12581
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  /43

  $2,495,000

  • 6 Beds
  • 5 Baths
  • 3,352 Sq Ft

  729 Cold Spring Rd Unit 731, Stanfordville, NY 12581

  Nestled at the end of a long private drive and surrounded by large estates and protected land, “The George” is a timeless 1798 farmhouse set on 7.2 serene acres in the bucolic heart of the Hudson Valley. With a private paddock, freshwater pond, and gently rolling lawns framed by mature trees, this historic estate offers the ultimate country retreat.The main house blends contemporary

  DOMINIQUE SHUMINOV William Pitt Sothebys Int Rlty

  729 Cold Spring Rd Unit 731, Stanfordville, NY 12581
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  /13

  $230,000

  • Land
  • 19 Acres
  • $11,856 per Acre

  A Skunks Misery Rd, Millerton, NY 12546

  Stunning 19.4 Acres – Estate Setting on a Premier Country RoadDiscover the perfect blend of natural beauty and refined location with this 19.4-acre parcel situated on a picturesque country road, renowned for its stately homes and rural charm.With multiple elevated building sites, long road frontage, and sweeping view potential, this property offers endless opportunities. Explore

  Robert Dunlop Havens Real Estate

  A Skunks Misery Rd, Millerton, NY 12546
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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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  /26

  $639,000

  • 4 Beds
  • 3 Baths
  • 2,300 Sq Ft

  297 Turkey Hill Rd, Red Hook, NY 12571

  First time on the market in a generation, this Turkey Hill Charmer has it all. When you pull in, a lovely rocking chair covered porch welcomes you; begging you to spend your summer evenings listening to the birds and enjoying the upstate air here. Walk in to a formal entry way to an open living room with 20 foot ceilings, primary bedroom with en-suite bath off living room and 2 great sized guest

  Chelsea Pollard-Seiler Mondello Upstate Properties

  297 Turkey Hill Rd, Red Hook, NY 12571
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  /13

  $4,950,000

  • 3 Beds
  • 2 Baths
  • 5,000 Sq Ft

  3362 New York 199, Pine Plains, NY 12567

  To-Be-Built Luxury Estate with Infinity Pool & Panoramic Catskill Views – Pine Plains, NY. Elevated high above the valley floor with sweeping, unobstructed Catskill Mountain views, this to-be-built custom estate is a rare opportunity in the heart of the Hudson Valley. Set on an extraordinary piece of land—offering total privacy and dramatic natural beauty—this 5,000+ square foot

  Michael Lund Corcoran Country Living

  3362 New York 199, Pine Plains, NY 12567
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  /32

  $2,495,000

  • 3 Beds
  • 3 Baths
  • 4,648 Sq Ft

  387 Skunks Misery Rd, Millerton, NY 12546

  Perched high above Millerton in the Hudson Valley, this exceptional 2020-built contemporary farmhouse estate commands 53± private acres with panoramic western views spanning the Catskills and Berkshire Mountain Range, including Mount Kaaterskill. Wide red oak hardwood floors unite the main level, where abundant natural light floods through expansive windows, creating an atmosphere of seamless

  Elyse Morris Elyse Harney Real Estate

  387 Skunks Misery Rd, Millerton, NY 12546
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  /27

  $335,000

  • 3 Beds
  • 2 Baths
  • 1,882 Sq Ft

  6099 New York 82, Stanfordville, NY 12581

  Rare Opportunity to create or invest in this commercial / residential building in high visibility location. This former mechanics shop and most currently a welding shop it offers a multitude of uses and possibilities. Light Manufacturing, Auto Repair, Artisan Studio, Retail, Storage and More! The solid building has 10- and 12-foot overhead doors and ceilings, 2 Rest rooms, Office, and plenty of

  Catherine Mondello Mondello Upstate Properties

  6099 New York 82, Stanfordville, NY 12581
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  /34

  $629,000

  • 3 Beds
  • 2.5 Baths
  • 2,120 Sq Ft

  35 Rowe Rd, Red Hook, NY 12571

  Set on 2.2 scenic acres, this spacious Raised Ranch offers a perfect blend of comfort and versatility. The main level features a primary bedroom with en-suite bathroom, two additional bedrooms, and a full hall bathroom. The living room with woodburning stove flows into the dining area with sliders to the deck—ideal for indoor-outdoor entertaining. The kitchen includes a center island and plenty

  Rita Longo Howard Hanna Rand Realty

  35 Rowe Rd, Red Hook, NY 12571
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  /40

  $600,000

  • 3 Beds
  • 2 Baths
  • 1,141 Sq Ft

  2 Redmond Way, Stanfordville, NY 12581

  Welcome to your private retreat, complete with 5+ acres of nature. The contemporary home features 3 bedrooms and two full baths. The living room is a flexible space with dining area options, as well as a wood-burning stove perfect for cozy winter days. . A wall of windows invites you to seasonal views and outdoor activities, while the deck off the living room is ideal for morning coffee or

  Louise Bradford HomeSmart Homes & Estates

  2 Redmond Way, Stanfordville, NY 12581
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  /17

  $639,000

  • 3 Beds
  • 2 Baths
  • 896 Sq Ft

  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
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  /30

  $540,000

  • 2 Beds
  • 2 Baths
  • 1,736 Sq Ft

  979 Duell Rd, Stanfordville, NY 12581

  This quintessential Cape Cod with spring-fed pond located on a magnificent farm filled country road between Millbrook and Stanfordville awaits you. Entering, you will find the living room with wood burning fireplace, and a library/den (currently set up as a bedroom). There is an oversized open kitchen with a bay window dining area and abundant storage. Off the kitchen is a heated, bright

  Steve Bruman Corcoran Country Living

  979 Duell Rd, Stanfordville, NY 12581
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  /37

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  11 Tribune Ln, Red Hook, NY 12571

  Picture-perfect vintage vibe meets endless possibilities on 1.6 private acres. This warm, enchanting 3-bed, 2-bath cottage combines nostalgic character with cozy, peaceful country living. From its inviting porch to the sprawling, sunlit yard full of mature trees, every corner of this property whispers warmth and charm. Here you can cultivate charming gardens of flowers and shrubs or grow herbs

  Bettina Louise Sturm Howard Hanna Rand Realty

  11 Tribune Ln, Red Hook, NY 12571
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  /25

  $430,000

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

  1601 Route 199, Red Hook, NY 12571

  Charming Renovated Ranch with Scenic Views and Endless Potential, l with extra additional side lot!! Welcome to this beautifully renovated ranch-style home offering 1,200 square feet of comfortable, single-level living. Featuring 3 spacious bedrooms and 2 full baths, this thoughtfully updated home boasts a functional and versatile layout with multiple private entrances—perfect for

  Jason Schobert eXp Realty

  1601 Route 199, Red Hook, NY 12571
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  /42

  $2,850,000

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

  3778 New York 82, Ancramdale, NY 12503

  An artist's delight, a gardener's dream and a naturalist's paradise. A thoughtfully designed and exceptionally well-built home set on 78 acres of woodlands and farmland with agricultural exemptions in place. This 4,250 SF architect designed home features multiple structures centered around a landscaped courtyard. Connected to the main home, by way of a covered portico, is a private guest suite

  Michael Stasi Corcoran Country Living

  3778 New York 82, Ancramdale, NY 12503

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