Pine Plains New York homes for sale starting at Fifty Thousand Dollars

$8,950,000 - Pine Plains, NY

25 Winchell Trail Pine Plains, NY - 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.

$1,575,000 - Pine Plains, NY

617 Bean River Road Pine Plains, NY - Major Update! Meticulously Maintained ELEVATED 3 BEDROOM/3 BATH Log Cabin-Style home and horse barns on 19+ acres with BREATHTAKING views. Set off a quiet country road, this stunning setting with impeccably manicured grounds captures one's attention upon arrival. One is immediately drawn to the expansive wood deck complete with built-in grill and impressive screened-in gazebo with fire-pit. This is unquestionably the perfect entertainment perch which captures the beautiful long views of the valley and hillsides. Fabulous open floor plan inside, with vaulted ceilings in living room with stone fireplace, large dining area, and light and bright gourmet eat-in kitchen with high-end appliances. Primary bedroom also has vaulted ceilings, stone fireplace, and large walk-in closet leading to primary bath. Study off of Primary Bedroom. Second bedroom on main level has been recently reconfigured. Another great entertaining space is located downstairs including a large area perfect for games, exercise or media room with kitchenette. A THIRD bedroom was recently created near a recently renovated full bath. 3 car heated garage with massive storage space upstairs. 45KW generator. For the HORSE ENTHUSIAST, the property also includes a hay barn, paddock, 4 stall horse barn & tack room, equipment sheds and arena. Great riding trails abound. This exceptional property is move-in ready and utterly magical.

$890,000 - Pine Plains, NY

1220 Hunns Lake Pine Plains, NY - 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!

$599,000 - Pine Plains, NY

115-133 Mount Ross Road Pine Plains, NY - Charming 1880s Farmhouse on 65.32 AcresThis classic farmhouse, originally built in the 1880s and expanded in the 20th century, offers generous living space with high ceilings and rich woodwork throughout. While the home needs extensive renovations, the potential is undeniable. The sprawling 65-acre property includes a scenic pond, a well-built barn, lush meadows, and tranquil woodlands, ideal for outdoor enthusiasts. Enjoy the peaceful, rural setting of Pine Plains, with easy access to local attractions like wineries, breweries, golf courses, and an array of outdoor activities such as skiing, biking, and hiking. If you're ready to roll up your sleeves, this property is waiting for your vision.

$598,000 - Pine Plains, NY

7766 S Main Street Pine Plains, NY - OPEN HOUSE Sun 5/18, 3-5pm By Appointment. Please call to schedule. Step into The Bluehouse, a breathtaking 1700s Saltbox-style country home that seamlessly blends historic character with modern charm and luxury. Lovingly restored in 2023, this light-filled retreat is situated in the heart of Pine Plains, NY, just a short stroll from the picturesque town of Pine Plains including the acclaimed Stissing House. This 3-bedroom, 2.5-bath home has been carefully updated to preserve its historic charm while incorporating contemporary comforts. Original wide-plank flooring runs throughout the second floor, where you'll find a primary bedroom with an en-suite full bathroom, along with two additional spacious bedrooms and a second full bathroom. The first floor is equally inviting, featuring a screened-in porch, the perfect place to enjoy morning coffee, unwind with a book, or entertain friends. A cozy living room with a fireplace creates a warm and welcoming atmosphere, ideal for relaxing or hosting game nights. The formal dining room is ready for memorable gatherings, while the renovated kitchen is fully equipped for all your culinary adventures, offering modern appliances, ample counter space, and a charming breakfast nook warmed by a wood-burning stove, making every meal feel special. A half bathroom on this level adds extra convenience. Step outside to the fully fenced backyard, where you can dine under the stars, enjoy a glass of wine by the firepit, or let your four-legged friend roam freely. The restored barn has been structurally reinforced and features new flooring-ready for the next owner to add the finishing touches. Whether envisioned as a game room, home office, art studio, or accessory dwelling unit (ADU), this space offers endless potential. With its historic character, modern updates, and prime location, The Bluehouse offers a rare opportunity to own a piece of Hudson Valley history while enjoying the comforts of contemporary living. Broker discloses ownership.

$525,000 - Pine Plains, NY

7786 S Main Street Pine Plains, NY - You wanted charm? You got it! This vintage 1903 village home in Pine Plains, NY formerly served as both the town pharmacy and library, and many of the bookshelves and all the quaint apothecary drawers remain intact. The large 3000sq foot home on a nicely landscaped yard of nearly a half an acre is filled with period details: wooden moldings, original door knobs and intricate iron hardware, a beautifully carved mantelpiece, and several built-ins. And, protected by carpeting for decades, there are beautiful wood floors throughout. Entered from either of two shady covered porches, the first floor has a living room (the former pharmacy), library, dining room, laundry room, powder room and an eat-in kitchen with a spacious mudroom attached. Upstairs there are four bedrooms, a study, and a full bath with a spacious walk-in closet. There's a walk-up attic that can be used for storage or finished off as additional living space. In the basement is a quite new furnace and a brand-new oil tank. While the house is in move-in condition, a bit of thoughtful updating of kitchen and baths will make the home really shine. Outside, the entirely fenced-in yard has gardens, a wide-open lawn perfect for entertaining and games, and a spacious barn that serves as a garage and workshop and has a large second floor that could become as an artist's studio or creative workspace. Steps away from popular local restaurants and the Stissing Center for the Arts, this property is right in the heart of this up-and-coming town. Less than two hours from Manhattan and close to hiking, biking, farmers' markets and antique centers, Pine Plains is an easy drive to the nearby towns of Millbrook, Rhinebeck, Millerton and Hudson. Come and see this place and make it your own!

$389,000 - Pine Plains, NY

618 Bean River Road Pine Plains, NY - 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.

$389,000 - Pine Plains, NY

48 Woodside Street Pine Plains, NY - 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.

$320,000 - Pine Plains, NY

4 Antlers Club Road Pine Plains, NY - Located in the picturesque Antlers Club Lake Community, this 2-bedroom, 2-bath Cape Cod offers a peaceful retreat with beach access and your own dock for kayaking, fishing, or relaxing by the water. The home features a bright and inviting layout, with spacious living areas, a well-equipped kitchen, and a full bath on the main level. Upstairs, a large bedroom and another full bath provide a cozy escape. Set back just a few hundred feet from the lake, it's private yet accessible! Enjoy the beauty and tranquility of lake community living while still being close to highways and shopping. Don’t miss this unique opportunity—schedule your showing today!

$299,000 - Pine Plains, NY

6 Carla Terrace Pine Plains, NY - 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.

Pine Plains, New York listings for sale

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