Courtesy: Elyse Harney Real Estate
860-435-2200
Light-filled 2006 home blends privacy with effortless convenience. An open-air front porch and a generous backyard frame inviting indoor/outdoor living. Inside, the living room centers on a charming stove, while the chef’s kitchen echoes the home’s airy feel with an island and open plan ideal for entertaining. The first-floor primary suite is a private retreat with a freestanding tub and tiled shower. A powder room and a large mudroom with built-in bench connect to the garage. Upstairs, three additional bedrooms share a full bath with double vanities and a washer/dryer hook-up. The lower level adds flexible space with a recreational room and an office/den. Country living, refined and easy. Set just minutes from the village of Pine Plains & 15-20 minute drive to Rhinebeck and Millerton
Courtesy: Keller Williams Realty
845-928-8000
Your Lakeside Sanctuary Awaits at 553 Lake Rd in Pine Plains NY. Imagine a life where your mornings begin not with an alarm, but with the gentle song of birds and the sun rising over the glassy waters of Twin Island Lake. Welcome to 553 Lake Road in Pine Plains—a home that doesn’t just offer a place to live, but a feeling of profound peace, warmth, and sanctuary. A Home Infused with Warmth and Light From the moment you step inside, you are wrapped in comfort. Gleaming hardwood floors guide you through a thoughtful layout designed to soothe the soul. The Living Room: Unwind by the crackling fireplace while gazing out at beautiful lake views. The Heart of the Home: An updated, sun-lit kitchen boasts abundant countertop and cabinet space, flowing effortlessly into a lovely dining area. The Sunroom: A bright, incredibly spacious sunroom offers the ultimate spot to curl up with a good book, practice yoga, or simply watch the seasons change. Space to Grow, Create, and Breathe The second floor features two beautifully appointed full baths, ensuring ultimate convenience with 3 bedrooms. Downstairs, a full walkout basement bursts with potential, offering the ideal layout to create an accessory dwelling unit (ADU), a guest suite, or rental space. For the creator or hobbyist, the 2-car heated garage is a dream come true, complete with a workshop and a spacious loft perfect for DIY projects or studio space. Peace of mind is also guaranteed with a whole-house generator. Embrace the Great Outdoors Step outside onto your brand-new Trex porch to sip your morning coffee, breathe in the crisp Hudson Valley air, and feel the stress of the week melt away. With over 3 private acres of your own land, you can hike, explore, and connect with nature right in your backyard. Lake access on your private dock just across the street, kayak or canoe around the lake for an interesting adventure. Looking for a challenge? The breathtaking trails of Mt. Stissing are just minutes away. The Location: A Seamless Escape Located under 2 hours from NYC with a straight, scenic drive up the Taconic State Parkway, this property is incredibly versatile. Whether you dream of a permanent full-time haven, a magical summer retreat, or a lucrative short-term rental/Airbnb, this home is ready to fulfill your dreams. Best of all, you are just 15 minutes away from the historic streets, gourmet dining, and culture of Rhinebeck and Red Hook.
Courtesy: Keller Williams Realty
845-928-8000
Welcome to 559 Lake Road in Pine Plains! Boasting direct views and access to Twin Island Lake, this beautiful property has a proven track record as a highly successful Airbnb. Whether you are looking for a lucrative investment, a dream summer getaway, or a year-round sanctuary, this home has it all. The entire front of the house features stunning, unobstructed lake views. Start your mornings on the covered porch sipping coffee, listening to the birds, and watching the wildlife on the water amidst beautiful perennial flowers. Inside, enjoy a bright, spacious open floor plan ideal for modern living. The layout includes a primary bedroom and bath with plenty of closets, plus a second bedroom and a flexible home office with a large closet, sleeps like a 3 bedroom. Step outside to hike up your own 4 acres of private land, or drive just 15 minutes to enjoy the top-tier restaurants and entertainment in nearby Red Hook and Rhinebeck. All this peace and quiet is located under 2 hours from NYC via the Taconic State Parkway!
Courtesy: Compass Greater NY, LLC
845-677-5311
Discover the charm and possibilities of this private lakefront property set on 5.9 picturesque acres. This updated 1950's cottage features three plus bedrooms and two baths, with a bright, inviting interior that immediately feels like home. As soon as you step inside, you're welcomed by a direct view of Twin Island Lake, creating a stunning first impression. Relax on the decks and take in the beauty of the changing seasons and sunsets over the water or spend time kayaking around the lake. Beyond the property itself, outdoor recreation is right nearby with convenient walking access to Stissing Lake, the Thompson Pond Conservation Area, and hiking trails on Stissing Mountain. Added amenities are A/C, generator and pellet stove. Located minutes to the Village of Pine Plains, where you can enjoy live entertainment and cultural events at the Stissing Center for Arts and Culture.
Courtesy: Rich Brenner Realty, LLC
914-456-4691
Step into the charm and character of a bygone era with this spacious early-1900s Colonial-style home located in the heart of the hamlet of Pine Plains. Offering over 3,000 square feet of living space, this 4-bedroom, 1.5-bath residence sits on approximately 0.47 acres and is filled with history, warmth, and timeless architectural details. Once home to both the town pharmacy and library, this unique property blends rich local history with classic Hudson Valley charm. Inside, you’ll find stunning original woodwork and trim, oversized rooms, high ceilings, and beautiful hardwood floors throughout — long protected beneath carpeting for many years and now ready to shine once again. The two-story home offers endless potential for restoration, modernization, or simply enjoying its authentic character as-is. A large barn located behind the home provides excellent storage, workshop space, studio potential, or future creative use. Perfectly situated in the center of town, the property is walkable to local restaurants, the post office, pharmacy, and other village conveniences. Outdoor enthusiasts will appreciate the nearby hiking and biking trails, while commuters and weekend travelers will love being just approximately 30 minutes from both the Amtrak station and the Metro-North Railroad station in Poughkeepsie. Conveniently located between Rhinebeck, Hudson, Millbrook, and Millerton, this home places you in the center of some of the Hudson Valley’s most desirable destinations. A rare opportunity to own a piece of Pine Plains history with space, character, and incredible potential.
Courtesy: Staley Real Estate, LLC
845-876-3196
Nestled on a country road in West Pine Plains, the Historic Hanlon Hill Farmstead offers a rare opportunity to own a piece of history. This 87-acre property, spanning five parcels, has been in the Hanlon family for six generations. The centerpiece is an 1840s eyebrow colonial home, set back from the road for ultimate privacy. As you enter the farm, you'll pass a serene pond and a charming one-bedroom guest cottage featuring wood floors and a beautiful brick fireplace. Currently rented for $1,000 per month, the tenant covers all utilities. The main house is a lovely blend of historic charm and modern comfort, with 4 bedrooms, 2 bathrooms, and gorgeous wide-board wood floors throughout. Nature lovers will appreciate the meadows, abundant woodlands, and diverse wildlife that surround the property. Farm roads wind through the land, leading to the highest points, where you can take in breathtaking sunset views. This land offers incredible development potential, with standing hardwoods ready for harvest, and the barn—24’ x 36’ with a metal roof—could easily be transformed into horse stalls or used for other farming needs. Whether you're an investor or an outdoor enthusiast, this property has endless possibilities. It’s ideal for hiking, hunting, or any outdoor activity you can imagine. The historic colonial features a large, covered front porch with its original door, opening into a grand staircase. To the right, a spacious living room boasts a large stone fireplace, and a small galley kitchen sits adjacent. To the left, you'll find a formal dining room and a bedroom with an antique bath, plus the main kitchen, complete with a wood stove. Upstairs, there are 3 bedrooms and a modern, fully-tiled bathroom with both a tub and shower. A cozy office or nursery is located off the largest bedroom. A three-season porch overlooks the meadows and orchard, offering a peaceful spot to relax. The property also includes a creamery, a smokehouse, and stunning stone retaining walls that add to its rustic charm. Conveniently located just off the Taconic Parkway, this farm is an easy drive to Rhinebeck, Red Hook, and Pine Plains. Whether you're looking for a serene retreat, a development opportunity, or a place to pursue farming, this historic property offers something for everyone.
Courtesy: Corcoran Country Living - Mill
845-677-0505
A rare offering of enduring beauty and thoughtful design, this extraordinary modern farmhouse--built in 2019--stands as a true masterpiece set on 52.32 acres of rolling landscape, with sweeping views of mountains, open hills, and the Roeliff Jansen Kill. Spanning 6,875 square feet, the residence blends refined craftsmanship with a warm, livable elegance. Reclaimed 19th-century pine floors with rose head nails run throughout, grounding the home in history while soaring ceilings--including 10'7'' in the kitchen and a dramatic 24'6'' vaulted, beamed living room--create a sense of scale and light. Walls of windows frame the house and look out onto the established English gardens and beyond to the surrounding hills and orchards. The heart of the home is a remarkable kitchen, complete with its own fireplace, a Lacanche range, and a full wall of glass overlooking the landscape. A separate pantry is equally well-appointed with marble countertops, SubZero refrigerator, and a Miele dishwasher. Every space reflects an uncompromising attention to detail. The main living room is both grand and inviting, featuring exposed beams, a fireplace, built-in library, and French doors that open seamlessly to the outdoors. The primary suite offers a private retreat with a 17'6'' vaulted, beamed ceiling, its own fireplace, and a wall of glass capturing the Berkshire Mountains. The spa-like bath includes marble double vanities, a clawfoot tub, and an open shower, complemented by custom-designed closets. A thoughtfully designed greenhouse breezeway connects the main house to a beautifully appointed guest wing. This unique space features soapstone sinks, plaster walls, and French doors leading to a charming courtyard with a fountain made from a 300 year old limestone trough. The guest wing includes a vaulted great room with kitchenette, bedroom, and bath, along with a separate studio or office with woodstove and an additional powder room--ideal for guests, extended stays, or creative pursuits. Additional features include an expansive laundry room with double washers, a dedicated yoga or fitness room, and a mudroom designed for both function and style. Outdoors, the property is equally compelling. There is a heated, saline 18' x 50' gunite pool and pergola for dining al fresco. The formal gardens are planted with heirloom roses, towering delphiniums and other classic cottage flowers that bloom the whole season long, and include a white garden that glows in the moonlight. This is a truly bucolic property with dry stonewalls, antique blue stone terraces and a walled vegetable garden just waiting to be planted in the spring. The land itself is rich and vibrant, with an organic orchard featuring multiple varieties of pear, apple, plum and peach, along with blackberry, blueberry, and raspberry bushes. A classic 24' x 38' barn with wood sided walls and a separate workspace offers further versatility and space for storing wood and tools. Bordering the property, the Roeliff Jansen Kill provides a peaceful natural edge with trout fishing, complemented by a tributary stream that meets the Roe Jan and picturesque waterfalls. Designed with sustainability in mind, the property incorporates solar energy and electric car charging while seamlessly blending efficiency with luxury living. An exceptional Hudson Valley estate where timeless materials, modern efficiency, and breathtaking natural surroundings come together in perfect harmony.
Courtesy: Compass Greater NY, LLC
845-677-5311
SET ON A NICELY LANDSCAPED AND PRIVATE YARD IDEAL FOR GARDENING WITH 1.37 ACRES TOTAL-(HOUSE ON .65 ACRE AND AN ADJACENT BUILDING PARCEL OF .72 ACRE). THIS INVITING WELL MAINTAINED 3-BEDROOM, 2-BATH RANCH OFFERS COMFORT AND FEATURES A LIVINGROOM WITH A FIREPLACE, LOVELY WOOD FLOORS THROUGHOUT AND A LARGE BASEMENT PERFECT FOR A WORKSHOP, RECREATION ROOM OR ADDITIONAL STORAGE. THE ATTACHED GARAGE IS ACCESSED THROUGH A LARGE SUNROOM/BREEZEWAY. LOCATED WITHIN MINUTES TO THE TOWN BEACH ON STISSING LAKE AND RECREATION AREA, STISSING MT. HIKING TRAILS AND THOMPSON POND BIRD SANCTUARY. PINE PLAINS IS A QUAINT VILLAGE IN NORTHERN DUTCHESS COUNTY WHICH IS PRESENTLY KNOWN FOR THE STISSING CENTER FOR ARTS AND CULTURE AND THE STISSING HOUSE RESTAURANT. MOVE RIGHT IN WITH NO WORRIES WITH A NEW ROOF AND KICTCHEN APPLIANCES, AN A/C FOR THOSE HOT SUMMER DAYS.
Courtesy: Mondello Upstate Properties
845-758-5555
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. Laundry room off the kitchen for convenience. Back off the living room is your primary suite, room for all your furniture and has a massive ensuite bathroom with soaking tub and shower, skylights bathe the room in sunlight. Off the dining room is a large living room with room for all. Two guest bedrooms stretch off the living room. Full guest Bathroom with tub on this wing of the home. High efficiency Split Units keep the home cool and supplement heat. Outside there is a world of possibilities for the craftsman, car enthusiast, or artist or artisan for Studio space, with an oversized two car garage with lofted storage, heat and electric in here. Then enter the massive 1287 square foot Garage with space for all your needs, storage or uses. In there there is electric, heat, and water. Additional Shed outside for storage,. Yard is perfect for all your needs, and is already outfitted with an invisible fence for your Furry family members. In the heart of Pulvers Corner, 5 minutes to Pine Plains Village, 10 minutes to Stanfordville and Millerton this is a fabulous location.
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 views. Inside, the home glows with natural light, featuring soaring vaulted ceilings, a gourmet chef's kitchen with high-end appliances, and a primary suite that serves as a true retreat with its own stone fireplace and oversized closet. A newly reconfigured second bedroom with an adjacent study provides the perfect versatile workspace. The lower level adds even more flair with a sleek kitchenette, media room, a full bath and a new third bedroom. The equestrian facilities includes a 4-stall barn, arena, hay barn, and fabulous riding trails, catering to every horse lover's dream. 3-car heated garage and a powerful 45KW generator. This impeccably maintained estate isn't just a home, it is a move-in-ready lifestyle that is utterly magical. Minutes to the villages of Millerton and Pine Plains. 2 hours to NYC.
Courtesy: Houlihan Lawrence Inc.
845-677-6161
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 overlooking a formal garden and continuing to a willow lined swimming pond. A guest house, just a stones throw away from the main house. To a beautiful high hilltop picnic meadow over looking the Catskills and Hudson Valley. Come see one of Dutchess County's gems with easy access to MIllbrook, Millerton, Pine Plains, and Sharon.,Level 2 Desc:OWNERS SUIT W/ BATH, BD2, BD3,InteriorFeatures:Electric Stove Connection,Walk-In Closets,Washer Connection,Electric Dryer Connection,French Doors,Heating:Zoned,Central Heat,FLOORING:Wood,Basement:Interior Access,EQUIPMENT:Carbon Monoxide Detector,Smoke Detectors,OTHERROOMS:Foyer,Library/Study,Office/Computer Room,Workshop,Breakfast Nook,Formal Dining Room,Laundry/Util. Room,Other School:IMS, DUTCH. DAY,Below Grnd Sq Feet:600,Level 1 Desc:MUD, FOY, LIV FPL, DEN FPL,LARGE LIV ON TO PORCH, KITCH FPL,FOUNDATION:Brick,Stone,Concrete,ExteriorFeatures:Outside Lighting,Landscaped,Cooling:Attic Fan,ROOF:Wood Shingles,Asphalt Shingles,AboveGrade:5546 Additional Information: Amenities:Guest Quarters,
Courtesy: Houlihan Lawrence Inc.
845-677-6161
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 year-round usability. The property features a total of 33 stalls across three well-equipped barns. The Morton barn includes 12 stalls along with a wash stall, tack room, bath, and a large one-bedroom apartment. The main barn provides 15 stalls, including box stalls, and is complemented by a feed room, office, workshop, and medical room. The tractor barn offers six additional stalls, and automatic waterers are positioned throughout the fields to support daily operations. Residential accommodations include a main house and two three-bedroom cottages, offering flexible living arrangements for owners, staff, or guests. The property is supported by four wells, multiple septic systems, oil fired forced hot air heating, and generator hookups with gas generators, ensuring reliable service throughout the farm. One of the most distinguishing features of Cedar Ridge Farm is its exceptionally flat topography—an uncommon asset in this region that makes the land ideal for a variety of equestrian uses, including the potential development of regulation size polo fields. While the property is not eligible for subdivision, it does include a designated homesite for future construction. Cedar Ridge Farm presents a rare opportunity to own a fully equipped, largescale equestrian property in one of the Hudson Valley’s most established and desirable horse communities. It combines functionality, beauty, and long-term potential, making it an outstanding offering at the highest level of the market.
Courtesy: Houlihan Lawrence Inc.
845-677-6161
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 clapboard siding and a welcoming front porch set the stage for a home that seamlessly blends 19th-century soul with modern amenities. Step onto original wide-plank flooring and admire the stunning, exposed hand-hewn beams. An oversized living room features a wood-burning fireplace and panoramic views from three exposures, with French doors leading to the expansive property. The formal dining room boasts an additional fireplace and two large china closets. The professionally equipped kitchen includes dual sinks, a premium professional range, a built-in refrigerator, and a sunny, south-facing breakfast room with pastoral views. A convenient butler’s pantry and powder room are also included on this level. Head upstairs to four bedrooms (two with fireplaces) and three bathrooms. The main house includes a fully equipped 3-bedroom apartment with a separate entrance—perfect for guests or staff. The property is a true compound, designed for both entertainment and flexibility. A fully outfitted barn includes a 3-bedroom apartment, a gym with a sauna, laundry, a workshop and a very large storage room which can easily be converting into more living space. Other buildings include another barn/workshop, a yoga studio, a 2-car detached garage with a storage loft, and a 60' equipment shed. This parcel offers endless potential for hobby farming, horses/livestock, or creating a private, quiet home office. Located in the desirable Shekomeko Valley, this property offers a rare mix of secluded tranquility and easy access to nearby towns.
Courtesy: Corcoran Country Living
845-876-6676
A Home with a view of Stissing Mountain! Enjoy gorgeous sunsets all year long from your front door. Spacious raised ranch on a level lot is move-in ready. Main floor has an open floorplan and wood floors throughout. The light filled kitchen with a nice sized island has new granite countertops. The storage room next to the kitchen could easily become a walk-in pantry. Primary bedroom has en-suite bath. A second hallway full bath is conveniently located for use by the other two bedrooms. First floor also has guest quarters that include a bedroom, half bath and sitting room or office. Finished basement with a gas fireplace for those chilly winter nights at home with family. An additional room that could be for gaming, office or den. Completing the lower level is a separate room for laundry. There is also a one car garage and an unfinished bonus room waiting for you to make it special to you. Plenty of yard space for outdoor activities and BBQs. Driveway has room for plenty of off-street parking. Quiet road conveniently located near the town park – beach, kayaking, playground, large pavilion, picnic area, etc. A short distance to Thompson Pond Nature Preserve, plenty of hiking trails including a trail up to the Stissing Fire Tower. Less than a mile from village center with its quaint shops and eateries – dine at The Stissing House or get pizza or burgers and don’t forget to visit the Stissing Cultural Center for a concert or a play. Come take a look!
Courtesy: William Raveis Lifestyles Rlty
860-868-0511
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 south-facing rise along the Shekomeko Creek, this newly constructed home is a serene, sophisticated sanctuary just two hours from New York City. A bold fusion of modern, industrial, and eclectic design, the residence offers over 4,700 square feet of light-filled, open-concept living on one level, including 3,057+/- sq ft main house, a stunning 1,046+/- sq ft attached greenhouse-conservatory that brings year-round indoor-outdoor living to life and a 1,423 sq ft +/- heated garage/studio/guest apartment. Every detail was curated with intention; from yaki sugi siding and a metal Kemper roof to polished concrete floors and walls of glass that frame unspoiled views of nature. The heart of the home features a bespoke chef's kitchen with live-edge shelving, custom cabinetry milled from trees on the property, concrete countertops, a butler's pantry, and a beverage bar. Double primary suites offer en suite wood burning stoves, spa-like baths with cast iron tubs, Italian tile, and handcrafted metal vanities. Both are complimented by airy bathrooms with natural light and industrial fixtures.A gas fireplace in the ample living room, vaulted ceilings, clerestory windows, and art lighting throughout create a harmonious blend of warmth and style. This is a home designed not just to live in, but to live fully. Outside, the entire 19-acre estate is bordered by classic white 4-board oak fencing, ensuring both privacy and visual continuity. A one-acre, 10-foot-deep pond and expansive flat pastures make this a dream property for equestrians, polo enthusiasts, hobby farmers, or anyone seeking a deep connection with the land. Zoned as a horse farm within an agricultural district, it offers rare potential for animal lovers and breeders alike. Car collectors and creatives will appreciate the oversized, fully heated garage and studio space outfitted with track lighting, storage, and the flexibility to serve as an art gallery, workshop, or one-bedroom apartment. With a 3,000 sq ft unfinished basement, covered porches, multiple patios, and estate management partners already in place, the property is as functional as it is inspiring. Additional features include an Endless Pools heated performance pool in greenhouse. The home has a sustainable, passive solar design and was constructed to allow for a future living roof/rooftop deck. New well, septic, and underground utilities. Energy-efficient systems throughout. Surrounded by horse farms and wildlife. Just minutes from the town center and Mashomack Polo Club. Whether you're an artist, gardener, equestrian, or collector, this unique Hudson Valley estate delivers a modern lifestyle without compromise. Offered for the discerning buyer seeking privacy, sophistication, and natural beauty in equal measure.
Courtesy: Houlihan Lawrence Inc.
845-677-6161
First time on the market! This magnificent 170-acre Modern Adirondack-styled estate near Millbrook, designed by architect Lloyd Taft, features a main house and three elegant guest cabins. Built by a third-generation builder of camps in upstate New York and the Thousand Islands, the cabin serves as the centerpiece of the compound. Meticulously maintained and tailor-made for year-round recreation, the property offers spectacular panoramic views of the Catskills and Taconic Hills from sunrise to sunset. With hand-hewn luxury reminiscent of Ralph Lauren’s aesthetic, the log-and-stone main residence features wraparound porches, a great room with a dramatic stone fireplace, a chef’s eat-in kitchen with Sub-Zero and Wolf appliances, a media room, a billiard room, and a luxurious primary suite with a fireplace and sunset terrace. The main house can accommodate ten people. Each of the three guest cabins, connected by a breezeway, features a fireplace, stone shower, kitchenette, and porch. In total, the guest quarters can accommodate twelve. Incredible amenities include a triple-height sports barn with an indoor sport court featuring pickleball, basketball, badminton, volleyball, a full gym, and a bonus arcade area. In addition, the sports barn can easily be converted into a large-format home theater. Additional outdoor features include an elevated paddle/pickleball court, a fillable freshwater swimming hole, a stocked pond, a full football/soccer field, six heated wildlife-watching perches, hiking trails, and an orchard with apples, peaches, sweet and sour cherry trees, blueberries, raspberries, and a cutting garden with a firepit. The compound also includes a party barn, a fish and game room, a separate office, and a grassy courtyard for croquet, bocce, and picnics. Ninety acres are professionally farmed by a local farmer. Ideally located close to Metro-North, Mashomack Preserve and Polo Club, Tamarack Preserve Club, and Orvis Sandanona, as well as the towns of Millbrook, Millerton, Pine Plains, Rhinebeck, and more. Unmatched privacy and resort-style living in the heart of the Hudson Valley.
Courtesy: George T Whalen Real Estate
845-677-5076
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 office, and a full bathroom off the hallway. There is also a walk up attic. Off the rear of the house, there is a workshop and several period barns. The property consists of two parcels; the house and barns on 10 acres plus an additional contiguous 5 acre vacant parcel. The land is lovely, with rolling hills and views of Stissing Mountain. This farm is less than two hours from New York City, convenient to Mashomack Preserve and minutes to the Pine Plains town center where you will find shops and restaurants, including the Stissing House Restaurant as well as the Stissing Center for Arts & Culture. For outdoor adventuring, nearby Stissing Lake and Stissing Mountain Hiking Trails are sure to please. A wonderful property for a new owner to bring back to life.
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 protected sanctuary. Additionally, the Lions Club Park provides a recreation field, frontage on Thompson Pond a with swimming area. Woodland Street is part of a network of streets ideal for walking and is close to the Pine Plains School's track and fields.
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 wraparound enclosed porch: on the first floor, find a large mudroom adorned with custom wallpaper, full bath, and a spacious kitchen that's wonderful for entertaining. A large dining and living room with wood burning fireplace has French doors that open onto a patio - perfect for al fresco dining. Off of the living room is a cozy family room. Upstairs, you'll find 4 bedrooms and a full bathroom. Original and reclaimed hardwood floors throughout this updated, light-filled country home, which offers Central AC and basement laundry. Outside, a vegetable garden, clawfoot tub, roses, peonies, and plenty of space to picnic with a view.Nature lovers will appreciate the short walk to Wethersfield, where you can explore some of the most beautiful walking trails in the Hudson Valley, while the property itself is landlocked by the Dutchess Land Conservancy, ensuring privacy and natural beauty. Enjoy your own private trail through the woods to a magical clearing with 360 degree Hudson Valley views. Most desirable location for anyone seeking Hudson Valley landscape with convenience to surrounding areas: 2 hours from Manhattan, 10 minutes from Stissing House, 15 minutes from Millbrook, Millerton, and Amenia, 20 minutes from Sharon, CT and Rhinebeck, and minutes from Dutchess Day School, Indian Mountain School, and the prestigious Millbrook School. Available for viewings today!
Welcome to 6 Carla Terrace! This 4-bedroom ranch nestled on a quiet tree lined cul-de-sac is well situated on nearly a half-acre level lot featuring a large private driveway for multiple vehicles. The dining area features sliding glass doors to the rear deck. Conveniently located just a short distance to downtown Pine Plains and its great shops, restaurants, schools, and of course, the Stissing Center for Arts and Culture. Pine Plains is within easy driving distance to the Berkshires, and all the best that Dutchess and Columbia counties have to offer. The full unfinished basement with its high ceilings offers many possibilities. While this home could benefit from TLC, it presents a tremendous opportunity. Blink... and it will be gone.
Secluded 2BR/2BA RANCH w/2 large decks, all wood floors and wood siding + detached 2 car garage on a7+cres in Hamlet zone. Great location between Pine Plains Village and Millerton on quiet road off Route 199. New well installed. Back on market after buyer couldn't qualify for mortgage.Easy to show unoccupied. Easy subdivision for 4acs with house and 3 acre vacant lot.
On just over ten acres of rolling hillside and pasture sits this quintessential Hudson Valley farmhouse. The oldest section of the home dates back to the mid 1700's, quite early for this region, while the Federal Style facade and front rooms were added c1850. The combination is striking the back of the house is both quaint and cozy, while the front of the home has high ceilings, big six-over-six windows and light filled spaces. The kitchen was a 2017 renovation the sink perfectly placed to overlook the Roeliff Jansen Kill, which borders the property and is stocked with brown trout by the New York DEC each spring. There is also a very fine swimming hole that remains deep even when the waters run low! Rhododendrons border the front porch and bloom in early Spring, cueing the return of summer, and the hydrangeas lining the front farm fence wait just a bit longer until the weather turns. By then, the wraparound screened in porch has become the place you spend most of your time, overlooking the water and surrounding hillsides. Inside, the house lives comfortably. The large kitchen was custom built by a local carpenter with inset cabinetry, new windows, a gas range and two sinks. The large, inviting island sits five. The wideboard floors are original. The dining room and family room sit side by side, with a fireplace at the far end and two sets of french doors leading outside. There is a half bath and mud room with radiant heated floors at the very back of the house, and the back door leads out to the run-in,'' an attached barn-like structure used for storage. At the front of the house you'll find a wood-paneled office with extensive built ins and the living room light, bright and airy. There are two bedroom wings, accessed via separate staircases. The back guest wing has two lovely bedrooms and a full bath. The front wing has three bedrooms and a full bath. The house has been lovingly cared for and thoughtfully updated over the current owner's 10+ year stewardship, with many updates, most recently a brand new boiler in 2025. The land has been certified organic and was most recently grazed and hayed by a favorite local dairy farm. Silvernails Farm is both whimsical and practical, a house built with integrity and a rare eye for aesthetics and proportion. 2h to NYC, 20m to Hudson and most importantly just 5m to Stissing House.
A long driveway leads to this imposing Greek Revival style house set high on a hill on 200 + acres of prime land overlooking Hudson Valley's farm country. Open fields and woodland with1600' of frontage on the Roeliff Jansen Kill. The house has 9000 sq ft with 12' ceilings throughout, large areas for entertaining, surrounding balconies for summer living and a 5000 bottle wine cave. The kitchen features a wood fired oven and the bathrooms are Carrera marble. Interior walls are plaster. All fittings and materials are of the highest quality. 9 bedrooms ensuite each with a view of the surrounding countryside. Just 2 hours north of New York City.
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 Architects to create a one-of-a-kind living experience. Using sustainable natural materials & state-of-the-art building technology, High View Farm is a perfect synthesis of contemporary modernism & rural barn. Working primarily with local artisans, they have created the ultimate combination of comfort & understated luxury. Relying on the endless power of the sun & the constant, cool temperature of geothermal energy they've realized a passive, architecturally-inspired EcoLux compound that will excite and endure for generations. The 5900 sf, 5 BR/5 BA main house has 3 primary suites and 2 additional ensuite guest rooms. The baths are all appointed with Waterworks fixtures & custom cabinets. The bedrooms, all with spectacular views, are generously proportioned with custom millwork closets with oak interiors. The kitchen is a chef's dream with an AGA Mercury induction stove, a Thermador fridge, an appliance pantry, 2 dishwashers, full butler's pantry with wine refrigeration, and a Miele integrated coffee system. The great room has a masonry fireplace & dining for 14 people. The ground floor has a Tonal Smart personal training machine, free weights, a yoga/stretching area, surround-sound cinema, and a cedar sauna. The piece-de-resistance is the four season indoor/outdoor room with a wood-burning fireplace-a dream for entertaining in a country home. The 50x11ft. saltwater gunite infinity pool, w/sun-shelf & tub spa, overlooks Stissing Mtn. and has a pool house with a live green roof, full kitchen & bath, & lounge/sleeping area. It's united to the pool by floor-to-ceiling sliding glass panel doors running the length of the pool. A lovely fire pit area for cooler summer & autumn evenings is just past the pool and up the ridge from the built-in BBQ. Closer to the main house, with its own wood-burning built-in BBQ, is the Maple Grove; another idyllic outdoor moment for more elaborate summer parties & alfresco dining.More marketing remarks in "directions to property" field.
A quaint antique home is for sale in Gallatinville, NY. This rare 1820 home on .68 acres in a quiet hamlet is loaded with quirky charm. With vintage wallpaper, lots of built-in cabinets and bookshelves, the 3-bedroom 1-bath house is as homey as they get. From the glassed-in porch, you step into a cozy entry hall / office, then into a large dining room. The country kitchen and comfortable living room with wood burning fireplace insert are off the dining room, and the bathroom is on the ground floor too. Upstairs are three bedrooms and a sitting area that can be converted to a bath or furnished as a library or study. In the shade of the large trees surrounding the house are a patio, an old root cellar, a stone barbecue and, in a sunny spot part of the property, a raised bed vegetable garden. A two-car garage is tucked into the hillside and there's ample parking for additional cars. Once lovingly landscaped, this property has been little-used for a couple of years, but a little care will bring the gardens back to life. And there are seasonal views of the Roeliff Jansen Kill across the road. Come check it out!
Pine Plains is located in New York. Pine Plains, New York has a population of 2,140. Pine Plains is less family-centric than the surrounding county with 19.59% of the households containing married families with children. The county average for households married with children is 29.92%.
The median household income in Pine Plains, New York is $67,212. The median household income for the surrounding county is $87,112 compared to the national median of $69,021. The median age of people living in Pine Plains is 51.4 years.
The average high temperature in July is 82 degrees, with an average low temperature in January of 13.7 degrees. The average rainfall is approximately 45.6 inches per year, with 51.9 inches of snow per year.
