429 properties for sale in Pine Plains

Clouds - An Architectural Retreat in Lakeville Set within 41 protected acres of rolling fields, wildflower meadows, and private trails, Clouds is an extraordinary contemporary country residence conceived in constant dialogue with its landscape. Approached along a winding drive through a cherry orchard-spectacular when awash in pink blossoms each spring-the house occupies the crest of a gentle bluff, commanding long views across meadows and to the distant Litchfield Hills. From a distance, the approximately 6,000-square-foot 5 bed and 5 full bath three level residence has the elemental simplicity of a refined agricultural building. Weathered cedar shake siding, a standing-seam stainless-steel roof, and a substantial stone chimney give the architecture a quiet permanence within its rural setting. Along the southwestern elevation, nearly 60 feet of windows transform the landscape into a living panorama, capturing rolling fields, wildflowers, mature trees, and the changing light from sunri

A Rare Find in an Exceptional Setting. Opportunities like this are few and far between - a beautifully located property with a Main House and a secondary studio-guest house. The two bedroom, two full bath main house radiates classic New England warmth, with hand-crafted oak kitchen cabinetry, pine-paneled ceilings, and a wood-burning stove that anchors the home in cozy, timeless charm. The main house has a semi open floor plan, the center of which is a spacious gourmet kitchen. The primary bedroom has its own adjacent office, and there is a second excellent office-bedroom on the main floor. The studio is a sun-drenched open concept loft with vaulted ceilings, offering wonderful flexibility - ideal for guests or extended family. This space would also serve as an incredible artist studio, offering endless possibilities. The lower level of the guest house has its own office, bath, and laundry. Set on a private parcel, yet just moments from the Salisbury Central School and the charming ham

Great Value in a Prime Location! This clean, well-maintained, move-in-ready home features 4 bedrooms, 2 full baths, town water and sewer. Located on a nice corner lot with plenty of parking. Enjoy low property taxes and convenient access to great restaurants, Salisbury Town Grove, and nearby private schools. You can't beat the price-come see for yourself! All room sizes are approximate

Classic Lakeville Colonial with Beautiful Gardens, Detached Studio and Walk-to-Village Location. Welcome to 15 Walton Street, a charming Colonial originally built in 1890 and thoughtfully renovated in 2000. This special home blends classic New England character with comfortable modern living and is ideally located within easy walking distance of the Lakeville village center. The approximately 1,173-square-foot home features 3 bedrooms and 2 full baths, traditional clapboard siding, and a welcoming front porch. The 2000 renovation complements the home's original character while providing a comfortable setting for today's lifestyle. Beautiful established gardens surround the property, creating a picturesque and peaceful setting throughout the seasons. The backyard offers space for gardening, outdoor dining, entertaining, or simply relaxing and enjoying the tranquil surroundings. A standout feature is the detached studio, currently used as a pottery studio. This versatile space is ideal f

Escape to your own private Hudson Valley sanctuary where rolling pastures, sparkling water, and endless possibilities await. Set on nearly 38 breathtaking acres, this extraordinary property offers the perfect blend of country living, equestrian excellence, and entrepreneurial potential. At the heart of the property sits a welcoming three-bedroom ranch home, perfectly positioned to overlook a picturesque one-acre pond and the surrounding countryside. Whether enjoying your morning coffee with panoramic views or relaxing beside the pond, every day feels like a retreat. The property has hosted an equestrian center and is fully equipped for horse enthusiasts The main barn features six stalls, three attached turnout paddocks, a feed room, tack room, wash bay, tack-up stall, and a spacious hay loft. A second barn includes two oversized stalls with run-in sheds and a fenced pasture, providing exceptional flexibility for boarding, training, or private equestrian use. Adding to the property's un

Exceptionally well maintained home with many upgrades including new siding, newer roof, new hard-wired generator, new windows, new flooring on first level, newly paved driveway. Private first level includes bedroom, full eat in kitchen, living room, full bath, laundry room and separate entrance. It's the perfect for extended family living. Upstairs includes full, eat in kitchen, dining room, access to deck, living room, three bedrooms and full bath

Step back in time and bring your vision to this classic 1870s Colonial, featuring original details throughout, perfectly situated on a lovely one + acre lot on a quiet country road. Flanked by mature pines and Flowering Hibiscus. The property offers a serene setting while being conveniently located near the charming village of Millbrook, NY. A unique opportunity for those looking to restore a piece of history and create a dream home in an unbeatable location. The main residence features three bedrooms and 1.5 baths, providing a solid foundation for renovation and modernization. Whether you’re looking to preserve original character or modernize the layout, the bones of this home offer endless possibilities. In addition to the main residence, there is a separate structure with two living areas and a workshop space. Each living area has 2 bedrooms and a full bath. Perfect for extended family or a home office, this additional space adds significant value and flexibility. Zoned residential

Expansive and sun-filled, this Mid-Century home is privately set on 23.7 secluded acres in Copake. High ceilings and generous living spaces define the 5 bedroom, 3.5 bath main residence, which features three fireplaces, a spacious primary suite, large screened porch, glass-enclosed sunroom, multiple decks, generator, and attached two-car garage. Set apart from the main residence, the barn-style guest house offers exceptional flexibility with three additional bedrooms, two full baths, and its own well, septic system, generator, and electric meter-ideal for extended family, guests, a home office or studio, or potential rental income. The beautifully established grounds are a standout feature of the property, with mature perennial gardens, specimen trees, dramatic rock gardens, and broad fields and meadows creating a wonderful sense of privacy and connection to the landscape. A gunite in-ground pool completes this distinctive country compound, offering abundant space for gathering, relaxi

Set in the hills above Millbrook, West Meadow is encircled as far as the eye can see by endless, heart-stopping views of the entire Hudson Valley. The house and pool sit on a beautifully landscaped plateau above a sloping lawn that gives way to a prolific cutting garden, rose beds, tennis court wrapped in wisteria vines, and groomed meadows. A fruit orchard and abundant vegetable garden enhance the pastoral beauty while providing a measure of sustainability. The architect Pietro Cicognani designed a home that harmoniously balances details of comfort, beauty, modernity, and history. West Meadow feels as if it’s been in place for centuries. The spacious great room boasts two 18th century stone fireplaces and floors of limestone tile imported from France. Fresh air and light pour in through six custom French doors facing both east and west. The library opens to a long covered porch and one of many stunning views. A central gathering place for friends and loved ones, the kitchen is warmed

Welcome to 27 Bobolink Lane! Tucked away at the end of a quiet cul-de-sac and surrounded by mature trees, beautiful landscaping, and 1.80 private acres, this custom ranch offers the perfect blend of comfort, functionality, and timeless charm. Designed for easy single-level living, the home features 3 bedrooms and 3 full bathrooms, including a private full bath in the primary suite, with all bedrooms conveniently located on the main level. The heart of the home is the beautifully appointed kitchen, featuring leathered granite countertops, KraftMaid soft-close cabinetry, a 5-burner induction cooktop, dual ovens, and a warming drawer, perfectly designed for both everyday living and entertaining family and friends. A dedicated eat-in area provides a casual space for meals, while the formal dining room offers an elegant setting for special occasions. Just off the kitchen, the inviting family room provides a warm and comfortable gathering space centered around a wood-burning fireplace, creat

THE MILLBROOK ESTATE An Extraordinary Hudson Valley Opportunity In one of the Hudson Valley’s most sought-after destinations, The Millbrook Estate offers a rare combination of scale, privacy, and enduring potential. Encompassing nearly 11,000 square feet on 11.1 secluded acres, the property presents an exceptional foundation for refined country living—equally suited for immediate enjoyment or for the thoughtful evolution that will make it uniquely your own. A dramatic arrival sets the tone. The grand two-story foyer features a sweeping staircase, soaring ceilings, elegant upper-level Juliet balconies, and a statement chandelier. Expansive entertaining spaces, multiple fireplaces, and a light-filled two-story solarium create rooms of both grandeur and comfort. The flexible floor plan adapts effortlessly to everyday living, large-scale entertaining, and a wide range of lifestyle needs. Generous family and guest accommodations are complemented by a separate guest cottage and multiple acce

Hidden along a quiet country road and on over 6 private acres surrounded by beautifully maintained forest and winding trails, the property offers a lifestyle where comfort, efficiency, and nature coexist in harmony. Spanning 3,396 square feet, the residence has been thoughtfully designed, meticulously maintained, and was constructed using Insulated Concrete Forms (ICF) from the foundation to the roof-an advanced building method seldom found in residential construction. Renowned for superior strength, remarkable energy efficiency, exceptional sound insulation, and lasting durability. Modern comforts include central air conditioning, central vacuum, and high-efficiency mechanical systems, complementing the home's advanced construction and remarkable efficiency. On the main level, an open-concept floor plan is filled with natural light and framed by peaceful woodland views. Rich bamboo flooring throughout creates a warm and sophisticated atmosphere. The chef's kitchen features a commercia

Over the Hudson River, and through the Ferncliff Forest Woods lies 532 River Road! Ideally situated in one of the Hudson Valley’s most desirable areas, this inviting property offers a wonderful opportunity to enjoy the beauty, character, and lifestyle that make Rhinebeck so special for an incredible value. With 3 bedrooms and 2 baths this sweet vintage home is spacious and all one level! Additional Two Car Garage for storage and more. Set on almost half an acre, the property is set back from the road and backs up to the Astor Forest 1000 acre woods. A short bike ride to the Village, or walk to Miglorelli Farm Stand every night for Hudson Valley Provisions. Convenient location puts you close to Rhinebeck Village, restaurants, shops, farms, Kingston Rhinecliff Bridge and the Hudson River. A wonderful opportunity to invest in the Rhinebeck market with a beautiful piece of land in an incredible location. Seller financing available with acceptable terms and deposit

Do you want a house which takes care of you, or do you want to take care of a house? If it's the former, then come to 397 Viewmont, Germantown, a newly completed 4-bedroom, 4.5-bath home with 4,100 square feet of above-grade living space, plus 1,100 square feet of finished lower-level space, on 6.86 private acres. Everything is new, including the systems, finishes, and appliances. Designed by a Hudson Valley artist, the house has a classically proportioned exterior with a nod to historic Hudson Valley architecture, but inside it feels open, airy, and full of light. At the center of the house is a dramatic great room with 30-foot cathedral ceilings, an upper-level loft overlooking the room, and a three-tiered south-facing wall of windows. Natural light comes in throughout the day, and a fireplace makes the large room still feel warm and comfortable. The chef's kitchen was designed for real use as much as for entertaining, with Sub-Zero refrigeration, a Miele induction range, two dishwas

Set on 18.61 acres with sweeping views of the surrounding countryside, 382 Leedsville Road offers a beautifully renovated take on country living in Amenia. The four-bedroom residence features three full and one half bath, with extensive improvements including a new roof, windows, siding, flooring, kitchen, and baths. Newly installed landscaping enhances the home's natural setting and creates a welcoming sense of arrival. Fresh, refined, and move-in ready, the property offers modern comfort, generous acreage, open skies, and four-season views-all within easy reach of Metro-North, the village of Millerton, and the Connecticut towns of Sharon and Salisbury. In addition the home is minutes from Troutbeck a renowned Hudson Valley resort

Victorian Elegance with Modern Comfort in the Heart of Rhinebeck Village. Discover timeless beauty and refined living in this exceptional Victorian home, perfectly situated in the heart of Rhinebeck Village. Rich in historic character yet thoughtfully updated for today’s lifestyle, this move-in ready residence offers a rare blend of classic charm and modern luxury. This stunning 3-bedroom, 2.5-bath home showcases exquisite period details, including original pocket doors and a graceful wooden staircase. The main level seamlessly combines old-world craftsmanship with contemporary upgrades, such as central air. At the center of the home is a chef’s kitchen featuring radiant heated floors, stainless steel appliances, a gas stove, double oven, spacious island with sink and seating, and a generous pantry. The inviting living room is anchored by a traditional Danish Morso wood-burning stove—perfect for cozy evenings at home. Upstairs, you’ll find well-proportioned bedrooms filled with natural

1982 double-wide manufactured home at Castle Gate Park in Wassaic. Two bedrooms and two bathrooms, about 1,150 square feet. The kitchen is equipped with newer appliances, including a dishwasher. Washer and dryer are in an interior laundry space. Both bedrooms offer usable room sizes, and the primary bedroom has an attached half bath. A detached shed provides additional outdoor storage. Setting is rural Harlem Valley with access to Route 22 and the Metro-North Harlem Line. Amenia, Millbrook, northwestern Connecticut, and the Harlem Valley Rail Trail are all nearby. Sale includes the home only. The lot is leased from the park and is not part of the conveyance. A monthly lot fee is payable to park management. Ownership may transfer only after the park’s application is approved in writing. Lot fee, community rules, and all measurements should be confirmed independently

31 Belgo Road offers a beautifully designed 2-bedroom, 2.5-bath main residence and a separate 1-bedroom, loft-style apartment above the garage, all set against spectacular views of Lakeville Lake. A new septic system was installed in 2024, which affords this home bedroom expansion capabilities. This upgrade is a significant value-add for potential logistics and future planning. Blending contemporary design with the charm of a classic New England home, this Litchfield County property embodies casual country living. The light-filled, open floor plan creates a seamless flow throughout the main living spaces. At the heart of the home is a state-of-the-art chef's kitchen with top-of-the-line appliances, opening effortlessly to a sunroom ideal for dining and gathering. The adjacent family room features soaring 13-foot ceilings, while the formal living room is highlighted by a striking floating staircase leading to the upper-level ensuite bedroom. The first-floor primary suite serves as a pri

Introducing The Edmund Rockefeller House, a circa-1855 residence set on 5.5 acres in the heart of Germantown. With a substantial barn, mature trees, and an unusually large parcel for a hamlet property, the offering brings together historic architecture, versatile space, and meaningful acreage. The approximately 2,828-square-foot, four-bedroom residence is defined by its wraparound porch, decorative millwork, and beautifully carved double entry doors. Inside, generous rooms and preserved details continue throughout. The first floor includes a large living room, dedicated study, kitchen with adjoining breakfast room, and an exceptional formal dining room with intricate inlaid wood floors and a stained-glass bay window. Upstairs are four bedrooms and a dedicated laundry room. The house includes one full and two half baths. The detached barn adds another dimension to the property, with extensive storage and workshop areas along with a finished studio space and full bathroom, well suited to

Welcome to Your Private Creekside Oasis in Pleasant Valley, NY. 4 Bedrooms | 3 Full Baths | 1 Acre | w/Mother-Daughter Suite. Set far back from the road, this beautifully maintained 4-bedroom, 3-full-bath home offers the perfect blend of total privacy, natural beauty, and flexible living space. Minutes from Millbrook, Pleasant Valley, Hyde Park, Rhinebeck and many other Hudson Valley hot-spots. The front porch features a well-kept, year-round hot tub, perfect for soaking under the stars on crisp winter nights or relaxing after a long day. The true crown jewel of this property lies just out back. A generous stretch of green grass and gardens flows seamlessly from the back deck all the way down to a lively, running creek at the rear property line. Whether you are hosting summer barbecues, gardening, or just enjoying the soothing sounds of the water, this 1-acre lot is an outdoor lover's dream. The main level offers a spacious layout with cathedral ceilings, wood burning fireplace, recent

A Spacious Cape with Possibilities. In the heart of Germantown, a familiar Cape reveals considerably more space than its straightforward exterior might suggest. With five bedrooms, three-and-a-half baths, high ceilings and a generous collection of rooms, 9 Church Avenue invites a new owner to imagine its next chapter. Recently subdivided from neighboring Resurrection Church and available for the first time as its own property, the former rectory has a practical character and a surprisingly expansive interior. Its many rooms lend themselves easily to bedrooms, guest rooms, home offices and everyday living. A recently renovated kitchen brings a fresh update to the center of the house, while a heated garage adds another practical dimension to the property. With high ceilings and rooms to spare, there is plenty of potential to rethink the flow and continue to improve the house over time. Set on a manageable lot in the center of the hamlet, 9 Church Avenue has Germantown's shops, restaurant

Clouds - An Architectural Retreat in Lakeville Set within 41 protected acres of rolling fields, wildflower meadows, and private trails, Clouds is an extraordinary contemporary country residence conceived in constant dialogue with its landscape. Approached along a winding drive through a cherry orchard-spectacular when awash in pink blossoms each spring-the house occupies the crest of a gentle bluff, commanding long views across meadows and to the distant Litchfield Hills. From a distance, the approximately 6,000-square-foot 5 bed and 5 full bath three level residence has the elemental simplicity of a refined agricultural building. Weathered cedar shake siding, a standing-seam stainless-steel roof, and a substantial stone chimney give the architecture a quiet permanence within its rural setting. Along the southwestern elevation, nearly 60 feet of windows transform the landscape into a living panorama, capturing rolling fields, wildflowers, mature trees, and the changing light from sunri

A rare opportunity to enjoy the best of village living, this beautifully maintained and thoughtfully renovated Millbrook property pairs timeless character with modern convenience and exceptional versatility. The three-bedroom, two-bath main residence offers 2,132 square feet of comfortable living space. A charming carriage house features a one-bedroom, one-bath apartment, built in 2018, encompassing approximately 1,000 additional square feet. There is also a gym, and a 2 car garage. Rich in potential, the carriage house offers an ideal setting for guests, extended family, or rental income, adding a valuable layer of flexibility to this distinctive offering. Originally built in 1910, the main residence has been fully renovated including a new kitchen in 2018 and the addition of a laundry room in 2019, thoughtfully blending the home's historic appeal with contemporary conveniences. Outside, a private, fenced backyard creates a peaceful retreat, where bluestone patios set the scene for ou

Make yourselves at home in this beautifully restored and thoughtfully updated ca-1880 farmhouse on Germantown's Main Street, where historic character and modern comfort come together with exceptional ease. Five bedrooms, four full baths, and comfortable living spaces centered around wood-burning fireplaces both upstairs and down offer remarkable flexibility for everyday living, multigenerational use, guests, or working from home, allowing everyone to come together or find a quiet corner of their own. The wide front porch and landscaped back terrace invite entertaining at home, while the central location puts the best of the Hudson Valley within easy reach. 20 min to Amtrak, 2 hours to NYC. Listing agent is the owner/seller of the property

A peaceful ranch across from a working orchard, with all the big-ticket updates done. Few homes in this price range offer the same combination of comfort, convenience, and long-term value. Set on a level acre directly across from a working apple orchard, 88 Rymph Road brings open skies, seasonal orchard views, and genuine quiet to your everyday backdrop, all while staying just minutes from everything you need. The updated front facade makes an immediate impression, with enlarged windows that flood the home with natural light and give it a fresh, modern presence from the street. Inside, the layout is as functional as it is inviting. A warm living room centers on a cozy stone fireplace. Three generously sized bedrooms and a main level laundry keep everything on one floor, exactly where you want it. A flexible den works just as well as a home office, playroom, or guest space, and the whole home simply flows. What truly sets this property apart is the quality of its updates and the genuine

A great 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’s classical character, while the surrounding landscape opens to long views across fields and wooded hills. Within, the house offers a sequence of rooms that feel both substantial and intimate. Rich wood paneling, a coffered ceiling, and two wood-burning fireplaces lend warmth to the principal living space, where a curved staircase rises to a wood-paneled upper landing. A lacquered library provides a more secluded place to read or work, while the dining room and window-lined sunroom accommodate the sociable rhythms of country life. The kitchen is arra

Nestled in the heart of Dutchess County, Salt Point Bosque offers the best of both worlds: the soul of an old Hudson Valley farm and the ease of modern infrastructure. This thoughtfully renovated compound includes an 1840s farmhouse, a barn with a workshop and guest quarters, an apple orchard, gardens, woods, a hot tub, a wellness spa with sauna and cold plunge, pastoral and pond views, as well as solar panels for energy efficient living. Enough space for guests, work, play and quiet. At the heart of the house is a spacious eat-in kitchen with vaulted ceilings and French doors opening to the patio, outfitted with a Viking Professional range and integrated Fisher & Paykel refrigerator. Adjoining living and dining spaces, a fireplace and a cozy library/den offer plenty of room to gather. An attached garage makes life easy. A first-floor primary suite has an ensuite bath and private access to the rear deck and hot tub overlooking the orchard and grounds. Upstairs are three additional ligh

Welcome to 367 & 375 Viewmont. A rare country estate spanning 13 acres across two parcels, this Germantown property centers on a beautifully sited 1860 farmhouse, set back off a quiet country road with open fields sweeping from the front and side of the property all the way to the rear, the property's privacy deepening as it moves toward the back, where the fields give way to a pond and a mature wooded buffer—offering historic character and real, tucked-away outdoor space just minutes from the surrounding Hudson Valley towns. Inside, the farmhouse is full of the kind of character that only a 160-year-old home can offer—high ceilings and windows throughout fill the rooms with natural light. The front door opens to a central stairway, flanked by a formal dining room on one side and a living room warmed by a woodstove on the other. Passing through either room leads into a wide central hallway: at one end, a side door opens to a porch, with a powder room tucked nearby; at the other end, Fr

Situated on 2.45 acres of land in the Town of Amenia, you will find this three-bedroom ranch style home. The grounds are lovely, with a private, mostly level yard. The home provides single level living and the property includes a detached three bay garage with a one-bedroom apartment on the second floor. Perfect property for a first-time home buyer or an investor. Conveniently located minutes from Metro North train stations and the enjoyable Harlem Valley rail trail. Just a short drive to Millbrook or Sharon, CT

Enchanted escape, loaded with charm! This lovely vintage 3 bedroom cape is shrouded with mature trees, flowering shrubbery and nestled privately on 1.08 acres. The old world stonework was cut and formed into the rock outcroppings decades ago by a master stone mason. This well built gem is solid as a rock. Turn key, with modern updates, hardwood floors, wood burning fireplace, built in dining hutch, an abundance of windows for cross breezes and plenty of sunlight. Serviced by town water and sewer is a real plus! There is a walk out from the one car basement garage. Our Tri-State area, beautiful Litchfield Hills, Berkshires MA and Hudson Valley NY are rich in culture, offering fine arts, restaurants with farm-to-table fare. Private and Public schools, medical facilities, golfing, skiing, hiking the AT, all within minutes. Come play, kayak, fish in out many lakes, rivers and streams. Less than 2 hrs and 1.25 hrs to NYC and Bradley Int airports respectively