34 properties for sale in Pine Plains

The History: The wonderfully characterful Hammertown was established in 1774, in a small hamlet of millworkers, farmers, and blacksmiths, amidst the lush pastoral landscapes surrounding what would become the town of Pine Plains, New York. The home and its grounds were occupied by only three families across 250 years, each family slowly developing the property to include, in addition to the sprawling main house, beautiful, sweeping trees and gardens, stone walls, a two-hundred-year-old barn that has housed many an ambitious project, and a sweet guest house nestled at the entrance of the land. The Main House: The seat of the property is a traditional colonial farmhouse, tastefully renovated and beautifully envisioned for the current era - while still respecting the home's history as it passed through a quarter of a millennium. Exquisite millwork lines every wall in the home, no less than five fireplaces are peppered throughout, and we mustn't forget the beautiful, wide-plank wood floors.

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

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 gar

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Beautiful, quiet neighborhood with park like setting. Lovely three-bedroom home with landscaped front, back and side yards. Spacious living room flows into quaint dining room with stained pine tongue u0026 groove walls u0026 updated country kitchen with backyard walkout access. Whether you

Welcome to Willow Vale Farmhouse, a 1790s farmhouse on just under 3 acres along a quiet country road in Pine Plains, Dutchess County, with 700 feet of frontage on the Shekomeko Creek. Over four years, the owners worked with a team of craftspeople to meticulously restore the home, preserving its historic character and bringing professional designer acumen to all the details. Inside, 3,065 square feet include 3 bedrooms, 3 full baths, and gracious rooms with new Venetian plaster and beautifully restored old growth Heart Pine wide plank floors throughout, warmed by multiple wood-burning fireplaces. Outside, a durable metal roof and new copper gutters cap the restoration in materials that will weather handsomely. A historic barn retains its hand-hewn beams to serve as a studio, collector

HOme is larger than it appears, all rooms are large except for kitchen, kitchen and bathrooms need to be redone, living room has hardwood floors and brick fireplace, new water storage tank, (2) 275 gal. Oil tanks in basement, 3 season sunroom in front, rear deck, mature landscaped corner lot, quiet desireable neighborhood, jet water pump, 2-car tandem garage under house, full basement

Set on a nicely landscaped and private yard ideal for gardening with. 65 acres total (an adjacent building parcel of. 72 acre can be purchased for an additional amount). This inviting, well-maintained 3-bedroom, 2-bath ranch offers comfort and has a handicap-accessible interior. Features include a living room with a fireplace, lovely wood floors throughout, and a large basement perfect for a workshop, recreation room, or additional storage. The attached garage is accessible through a large sunroom/breezeway for three-season use. Located within walking distance, only minutes to the town beach on Stissing Lake and recreation area offering swimming, boating, and summer children’s camp. Also nearby is Stissing Mt. With 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 kitchen appl

A Home with a view of Stissing Mountain! Enjoy gorgeous sunsets all year long from your front door. Many updates. Including a new roof! 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 bonusroom 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 room waiting for you to make it special to you. Plenty of yard space for outdoor activities and BBQs. Driveway

Welcome to Willow Vale Farmhouse, a 1790s farmhouse on just under 3 acres in Pine Plains, Dutchess County, with 700 feet of frontage along the Shekomeko Creek. Once home to Mon Blason, a French restaurant known as the region's first haute cuisine, this stately 3-bedroom, 3-bath house has been meticulously restored by professional designers, from the chef's kitchen with a La Cornue range to the wood-burning fireplaces and beautifully updated baths. Old-growth Heart Pine floors run throughout. Outside, enjoy a bluestone terrace, hot tub, two artesian-fed swimming holes, and a historic barn with hand-hewn beams. Just two hours from NYC and minutes from the acclaimed Stissing House, it's a place for summer swims, winter fires, and long dinners in every season of the Hudson Valley

A good country house reveals itself through its relationship to the land, the proportions of its rooms, and the pleasure of spending time there. At Heron Hill, these qualities come together in a Greek Revival home set on 38 acres in Pine Plains, in the heart of Millbrook Hunt Country. The white clapboard facade, framed by rolling lawn and clipped boxwood, has a pleasing balance and quiet presence. A columned entrance establishes the house

Set on a nicely landscaped and private yard ideal for gardening with. 65 acres total (an adjacent building parcel of. 72 acre can be purchased for an additional amount). This inviting, well-maintained 3-bedroom, 2-bath ranch offers comfort and has a handicap-accessible interior. Features include a living room with a fireplace, lovely wood floors throughout, and a large basement perfect for a workshop, recreation room, or additional storage. The attached garage is accessible through a large sunroom/breezeway for three-season use. Located within walking distance, only minutes to the town beach on Stissing Lake and recreation area offering swimming, boating, and summer children

More space and flexibility than you might expect! Set along a quiet country road in the Town of Gallatin, just outside Pine Plains, this 3-bedroom ranch offers approximately 1,860 square feet of living space with a finished lower level, providing plenty of room to spread out, work from home, entertain, or accommodate guests. The main level features hardwood floors, a full bathroom, three bedrooms, and a functional layout that

Welcome to 16 Ryan Road, a spacious 3-bedroom, 2-bathroom home in the scenic Pine Plains area. Featuring a large kitchen with plenty of workspace, a center island, and a functional layout with generous living areas, this home offers a great foundation for your next project. The property needs some updating and is ideal for a buyer looking to add their own personal touches and build equity. With a practical floor plan, comfortable bedroom space, and plenty of potential, this could be an excellent opportunity for a first-time buyer, investor, or anyone looking for a fixer-upper in a desirable Hudson Valley setting. Bring your vision and make this home your own!

The History: The wonderfully characterful Hammertown was established in 1774, in a small hamlet of millworkers, farmers, and blacksmiths, amidst the lush pastoral landscapes surrounding what would become the town of Pine Plains, New York. The home and its grounds were occupied by only three families across 250 years, each family slowly developing the property to include, in addition to the sprawling main house, beautiful, sweeping trees and gardens, stone walls, a two-hundred-year-old barn that has housed many an ambitious project, and a sweet guest house nestled at the entrance of the land. The Main House: The seat of the property is a traditional colonial farmhouse, tastefully renovated and beautifully envisioned for the current era. While still respecting the home's history as it passed through a quarter of a millennium. Exquisite millwork lines every wall in the home, no less than five fireplaces are peppered throughout, and we mustn't forget the beautiful, wide-plank wood floors.

Charming Cape Cod Retreat on Nearly 6 Acres in Pine Plains. Tucked away on a quiet country road just outside the village of Pine Plains, this charming three-bedroom, two-bath Cape Cod offers the perfect blend of country tranquility, comfortable living, and endless possibilities on nearly six beautiful acres. Welcoming you home with its cheerful yellow exterior, the spacious main level features a comfortable living room, dining area, kitchen, and convenient three-quarter bath. Upstairs, you’ll find three bedrooms and a second full bath, providing plenty of room for family and guests. The walkout basement offers excellent potential and could easily become a creative studio, workshop, hobby space, home gym, or additional living area. A one-car garage with storage below adds even more practicality and space. Step outside onto the generous rear deck and take in the peaceful surroundings. The home is privately set back from the road among mature trees and a shady lawn, while the wooded porti

Welcome to 559 Lake Road in Pine Plains! Boasting direct views and access to Twin Island Lake, this beautiful property has it all, lake and mountain views! 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 Stat

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 owne

2 fireplaces pine plains/ hudson valley / stissing lake stunning lakeside 4br/2.5BA beautiful home nestled under the majestic Stissing Mountain in private Antler Club co-op. An outdoor enthusiast

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 bonusroom 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 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 pa

A rare opportunity to own two beautifully renovated residences on 2.5 private acres in Millerton. The property features a three-bedroom main house and a separate two-bedroom cottage, thoughtfully positioned to provide privacy and independence for each residence. Both homes have been fully renovated with gorgeous finishes and are truly turnkey. The charming two-bedroom cottage offers exceptional flexibility, whether used as private guest quarters, a home office or studio, accommodations for extended guests alike or a source of rental income. The property presents an attractive investment opportunity, with the option to live in one residence while renting the other. Privately set yet conveniently located just 2.4 miles from the village of Millerton, this unique property combines the appeal of two move-in-ready homes with outstanding versatility and income potential. This property is located in an area known for its scenic beauty, farm to table restaurants and wineries. Close to the Wassa

Introducing Gallatin Hill; a private country retreat on 21.5 acres with sweeping views across the rolling hills of the Hudson Valley. Perched high above the surrounding countryside, the property combines a bright, modern home, expansive outdoor living spaces and an in-ground pool in an exceptionally peaceful setting. The 2,240 sq ft home offers 3 bedrooms and 3 full baths. At its center is an impressive open living space with soaring vaulted ceilings, exposed beams and walls of windows that fill the room with natural light and frame the landscape beyond. The open kitchen features a large center island with seating and flows directly into the dining and living areas. A wood-burning stove anchors the living room, while oversized glass doors open onto a large deck overlooking the property and distant hills. The main level also includes the primary suite with custom built-in storage and private bath, along with two additional bedrooms and a second full bath. Downstairs, the finished walkou

Beautiful, quiet neighborhood with park like setting. Lovely three-bedroom home with landscaped front, back and side yards. Spacious living room flows into quaint dining room with stained pine tongue & groove walls & updated country kitchen with backyard walkout access. Whether you're relaxing in front of the fireplace in the living room or entertaining friends at the backyard fire pit, you will love your new life in beautiful Pine Plains township! Updated kitchen with Farmhouse Sink & Butcher Block counters and shelving. Complete top of the line package of Samsung Wi Fi appliances including Samsung Refrigerator, Stove, Microwave & Washer/Dryer. Hardwood floors throughout. Newer roof and boiler. Brand new finished outdoor shed stays! Short walk to Stissing Pond Rec Beach, ball fields and boat launch. A nature enthusiast's dream with nearby hiking trails throughout beautiful Stissing Mountain as well as Thompson Pond & Twin Island Lake, all just a few minutes’ walk through quiet back ro

Set on 50 acres of complete privacy, this 1930's Colonial sits alone with sweeping views to the Berkshires. The home offers country living with a Livingroom with a fireplace & French Doors, Dining room with French doors opening to a porch. There is a heated sunroom to enjoy the quiet outside. The primary suite includes its own bathroom and a balcony perfect for morning coffee or stargazing. For added space, the third floor has been made into a yoga/workout room, along with an office and a bath. There are additional two bedrooms and 1 1/2 baths. Outside, sits a charming gazebo overlooking a tranquil pond perfect for nature watching. Also, there is a two car garage and an additional barn for a workshop or studio. Some updates are needed. 18 acres have a conservation easement

2 fireplaces pine plains/ hudson valley / stissing lake stunning lakeside 4br/2.5BA beautiful home nestled under the majestic Stissing Mountain in private Antler Club co-op. An outdoor enthusiast's dream! Fully furnished and move in ready. Whether this lakeside home is your year-long residence or vacation & holiday retreat, Stissing Lake will be your new favorite spot in the beautiful Hudson Valley. Exceptional craftsmanship with beautiful decor, built in shelving, molding & hardwood & tiled floors throughout entire home. Natural light throughout entire home from large windows & skylights. Soft recessed lighting & fixtures throughout. Open kitchen, dining and living room layout with fireplace, double sliding glass doors opens to large deck offers the perfect setup for entertaining company or relaxation at its finest. First floor den / media room in addition to kitchen/living room layout with beautifully designed full bathroom. You will be impressed! Main level office makes this a perfe

Attractive 3 bedroom, 1 bath cape cod loaded with recent improvements. Attractive open floor plan includes kitchen w/stainless appliances, granite counters & breakfast bar, which flows seamlessly to living room w/fireplace. Two first floor bedrooms and tile bathroom. Second floor includes generously sized bedroom plus office/den and storage space. Three season front porch is the perfect place to relax. Recent improvements include roof, furnace, water heater, pressure tank and 200 amp electric service. One car garage plus large workshop/studio space complete with insulation & electric and dedicated driveway. All situated on park-like property just minutes from shopping, dining, Stissing Lake and Taconic State Parkway. Attractively low taxes. An opportunity not to be missed

Welcome to Sigler Estate, a park-like Hudson Valley compound of country houses, historic barns, and cultivated grounds on nearly sprawling 40 acres, minutes from the hamlet of Pine Plains. A new heated 50-foot saltwater pool sits among rolling meadows, mature woodland, and stone-terraced gardens. A restored vintage post u0026 beam home with big views toward the Taconic Mountains, a charming white clapboard cottage, and a one-bedroom studio have each been given a professional designer renovation, and the circa 1930 Main House, with six fireplaces, awaits restoration. Along the drive stands the original Silvernails railroad depot, a link to the estate

A true treasure and piece of Pine Plains history, this elegant circa-1903 residence offers an exceptional blend of historic character, architectural detail, and extraordinary potential. Boasting over 3,000 square feet, four bedrooms, and 1.5 baths, the home showcases generously proportioned rooms, soaring ceilings, original woodwork, pastel tile and classic period trim that speak to its enduring charm. Once home to the village pharmacy and library, this remarkable property carries a unique legacy, ready to be thoughtfully restored and elevated. Set on approximately 0.47 acres, the grounds include a lofted barn offering a wealth of possibilities for a studio, workshop, or additional storage. Lovely fenced yard with plenty of space for a garden, your pets and entertaining al fresco. Perfectly positioned in the heart of Pine Plains, the property offers a quintessential Hudson Valley lifestyle, with shops, bookstores, restaurants, and local amenities just steps away. Everyone will want to

Charming ranch style home sited high on a hilltop with sweeping views of twin island lake. Main level offers three bedrooms, living room with fireplace and a year-round sun room. Lower level is also finished providing plenty of additional living space plus a summer kitchen

New construction. Be in for the holidays! Discover an extraordinary expression of modern luxury, where architectural sophistication meets the breathtaking natural beauty of the Hudson Valley. Privately situated on over eight magnificent acres, this exceptional 5,000 plus-square-foot contemporary residence offers an unparalleled sense of serenity, seclusion, and understated elegance, all framed by sweeping views of the majestic Catskill Mountains. A picturesque, winding drive welcomes you to this striking architectural retreat, where dramatic rooflines, expansive walls of glass, and thoughtfully designed living spaces create a seamless connection between refined interiors and the surrounding landscape. Designed for both sophisticated entertaining and effortless everyday living, the residence features two luxurious primary suites, thoughtfully positioned on the first and second floors to provide exceptional privacy and versatility. An expansive wraparound deck invites you to experience t