415 properties for sale in Pine Plains

Set on just under 4 acres along County Route 7, this property offers a farmhouse ready for restoration and a straightforward starting point for creating something of your own. The house is ready for updating and restoration, with a well and septic system already in place. With the subdivision currently in process, the property offers a manageable amount of land and plenty of room to shape the setting around the existing farmhouse. The location puts you minutes from Copake Lake and approximately 12 minutes from the Taconic State Parkway, with Hudson and Great Barrington both within easy reach. Surrounded by the landscape and amenities of the Hudson Valley and Berkshires, this is a property with a solid foundation and a blank slate for its next chapter

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

The Blue Barns are a true retreat, set just outside the hamlet of Germantown. Built in the early 1800s, two historic post-and-beam structures have been artfully transformed into an expansive modern country residence. Set on 2.2 acres, the property is perfectly situated between the cultural destinations of Hudson to the north and Tivoli and Rhinebeck to the south. Every room in the home is generous in scale, and the spaces have been designed with gatherings of friends and family in mind. Thoughtful finishes, including burnished concrete floors with radiant heat, exposed weathered wood beams, lofted rooms and vaulted ceilings balance the historic with the new. Modern amenities further set the home apart, including a new heated swimming pool, radiant floor heating, a soapstone woodstove, and even an indoor cedar sauna. At the heart of the home is a double-height great room, which combines soaring ceilings, hand-hewn timbers, wide-plank wood floors, and oversized windows overlooking the gr

Ready to make the move to Rhinebeck in the beautiful Hudson Valley? Welcome to 19 Closs Drive, where timeless charm meets modern comfort in this beautifully updated, move-in-ready 3-bedroom, 2-bath ranch, ideally located just a short stroll from the heart of Rhinebeck Village. Enjoy easy access to restaurants, charming boutiques, cafes, schools, spas in this sought-after Hudson Valley community. You will appreciate the home's exceptional curb appeal. New siding & attractive stonework (2020), along with a welcoming Mission-style front porch and entry door, create a warm first impression. Inside, gleaming hardwood floors flow throughout the living room and bedrooms. Abundant natural light fills the living room, where a cozy fireplace makes the perfect gathering place during every season. The beautifully renovated kitchen is the centerpiece of the home, featuring granite countertops, a center island, stainless steel appliances, & tile flooring. Open to the dining area, this thoughtfully d

This expansive ranch-style home is situated on a quiet cul-de-sac in Lakeville, CT, just off Wells Hill Road. The property offers 3-Bedrooms, 3-Bathrooms, two living areas, a formal dining room, and a modernized kitchen, all characterized by abundant natural light and a welcoming ambiance. Two of the Bedrooms are en suite and the third utilizes the Hall Bath. The Family Room includes a separate Office Area, both of which are privately located on the side of the home opposite the Bedrooms - offering privacy and versatility in use. A covered breezeway provides a connection between the home's mudroom and an attached garage, which also features a screened porch at the back. This 1.3-acre lot offers usable land and mature landscaping in a sought-after area

Middlefield, an exceptional 45-acre Hudson Valley estate designed by AD100 architect Gil Schafer, is a masterful interpretation of Classical architecture. The residence reflects Schafer’s celebrated approach to the American country house; timeless in its proportions and craftsmanship, yet relaxed, comfortable, and entirely suited to modern life. Approached by a winding drive through mature trees and native plantings, the Greek Revival residence is beautifully sited within its private landscape. A classical double-height portico and gracious proportions give the house a timeless presence, while expansive windows connect the interiors to the surrounding gardens, lawns, and woodland. A gracious center hall opens to beautifully scaled living and dining rooms filled with natural light. Throughout the house, newly installed antique wide-plank floors, custom millwork and hardware, antique mantels, and carefully considered architectural details create warmth and character. A generous three-sea

Welcome to 16 Knollwood, a well-maintained 3-bedroom, 1-bath ranch set on a desirable corner lot in a prime Rhinebeck location. Offering a comfortable, easy-living layout, this home features beautiful hardwood floors, quartz countertops, stainless steel appliances, and new windows. The one-car garage adds everyday convenience, while the finished basement provides an additional 1,184 square feet of versatile living space—ideal for a recreation room, home office, gym, or hobbies. With 1,376 square feet of above-grade living space plus the finished lower level, there is plenty of room to spread out. Enjoy the appeal of single-level living in a sought-after Rhinebeck setting, close to the area's shopping, dining, and amenities. A wonderful opportunity to make this inviting home your own!

Charming Circa-1920 Farmhouse in the Heart of the Harlem Valley Nestled along one of Amenia's picturesque country roads, 309 Amenia Union Road is a charming circa-1920 farmhouse set on approximately 2 private acres in the heart of the Harlem Valley. Surrounded by rolling fields, mature trees, and neighboring farmland, this property captures the quintessential character of the Hudson Valley countryside while offering exceptional potential for its next owner. Dating to the early 20th century, the farmhouse retains the proportions and character that make historic country homes so appealing. Approximately 1,920 square feet of living space includes 4 bedrooms and 1 full bathroom, with a traditional two-story floor plan that provides a wonderful foundation for restoration, renovation, or personalization. Sun-filled rooms, generous living spaces, and classic farmhouse proportions create an inviting sense of warmth and possibility. The main living areas offer plenty of flexibility for modern c

Welcome to this beautiful home dead end location AND is the QUEEN OF THE LAKE on Robinsons Pond! Amazing 101' of water frontage! Situated high on the property this one of a kind home enjoys incredible, beautiful waterfront views. The exterior stone walls give this home unprecedented distinction. 3 Full levels of outdoor living and possible entertaining space. The first floor features a Trek Deck with clear railings to sit and enjoy a cup of coffee or'whatever' lol while the sun sets or rises. The lower level enjoys a slate patio with 2 magnificent curved granite staircases on either side of the property to the yard/grass level. There is a totally separate private section/area that was built and is ready and waiting for your Hot Tub to be installed! What an unbelievable setting for any event, wedding, or just enjoying life in this fabulous property. The mid section of the yard is totally flat, completely fenced in with rod iron pretty fencing and can host any type of any party you can i

The historic c. 1810 house at 3244 Sharon Turnpike has been a defining presence in Harts Village, the oldest part of Millbrook, for more than two centuries. Phillip Hart and his wife, Catherine, who lived in the yellow house next door, set aside a portion of their property for their eldest daughter and her soon-to-be husband, and Phillip Hart built this gracious center-hall home for them in 1810. The enclave was later named Harts Village in his honor. For those who appreciate the way architectural details bring history to life, this exceptional home tells its story through the many original elements that remain. Twelve-over-twelve windows with wavy glass fill the rooms with natural light, while period moldings, front and rear parlors, plaster walls, a butler's pantry, chestnut and heart pine floors, and a wood-burning fireplace reflect the craftsmanship of its era. The original portion of the home is crowned by a slate roof. The sellers are only the fifth owners of this remarkable prop

Full of charm, character, and opportunity, this circa-1900 home is ready for its next chapter. Featuring 3 bedrooms, 1 bathroom, and a spacious attached two-car garage with additional storage above, this property offers a wonderful opportunity to bring your vision to life and restore its timeless appeal. While the home would benefit from some updating, its classic character and potential make it an exciting opportunity for buyers looking to create something truly special. An additional highlight is the adjacent 13.4-acre parcel, being offered separately, providing a unique opportunity for those seeking additional land. Whether you're looking for a home to make your own or an investment with potential, this Wassaic property is full of possibilities!

Just minutes from the village of Millbrook, this beautifully renovated three-bedroom, two-bathroom split-level residence offers an exceptional combination of sophisticated design, turnkey living, and resort-like amenities. An extraordinary offering at $635,000. Every detail has been carefully considered, creating interiors that feel polished and elevated without sacrificing comfort. Beyond the main living spaces, the property offers a dedicated home office and gym, providing flexibility for both work and wellness. Thoughtfully renovated from top to bottom, the home pairs custom cabinetry, high-end appliances, and upgraded systems with a warm, highly livable aesthetic. There are three zones of baseboard heat with Bosch air conditioning, a Navien high efficiency gas boiler with instant hot water. Set on 1.46 beautifully landscaped acres, the grounds are designed for effortless enjoyment, with a 16' x 32' in-ground pool creating a private summer retreat. A large three-car garage and works

Upper Rhoda Pond in Copake, New York (Southern Columbia County) is a very special place. About 2 hours from New York City, it is a private body of water with no public access. The waterfront area includes docks and a kayak to row out to your exclusive floating raft. This 3 bedrooms (plus office) has 3 bathrooms and is approximately 1944 square feet. The open floor plans lends itself to family, friends and entertaining. Wood-burning fireplace to warm up on those cool nights. Fiber-optic is on premises. The screened porch has panels, so that you can take in the country location and water views all year round. There is even a heater out there. The lower level has a sizeable family room and includes a pool table and ping-pong table. Storage has been very well organized and there is plenty of it. All this is sited on over 2.5 acres. There is a detached two-car garage and gardens. This central location makes it so convenient to so many cultural activities (Tanglewood, Catamount Adventure Mou

Situated just minutes from the town of Amenia, this three-bedroom, two-bath home offers fresh opportunity and convenient access to local amenities. The kitchen features cabinetry and connects to the dining area, while the adjoining living and dining rooms create a flexible layout. A bright sunroom with sliding doors provides additional living space and abundant natural light. The primary bedroom includes a walk-in closet and an en-suite bath with a walk-in tub. Additional features include a full basement for storage and an attached garage. Located minutes from the Metro-North train station and within walking distance of the Harlem Valley Rail Trail, this property offers a convenient setting for enjoying the surrounding area

Offered to the market for the first time, this four-bedroom Cape Cod enjoys a very private setting on 3.61 acres in Millbrook. A long driveway leads to expansive lawns and views, creating a peaceful setting for outdoor living. Hardwood floors, a fireplace, a deck, and an attached garage complement the home, while a whole-house generator adds convenience

Kinglet Cottage is set on ten acres in one of Millbrook's most sought after areas. This enchanting 19th century cedar shake cottage is surrounded by large estates and located on a scenic country road, offering a rare opportunity for privacy, tranquility and all that Millbrook has to offer. The two bedroom home retains its timeless character with beautiful hard wood floors, a convenient mudroom, and a lovely front porch overlooking the surrounding landscape. The nicely sized kitchen offer ample space for a small dining table or center island, with a partial butcher block countertop adding warmth and character. The living room features a wood stove, creating a warm and inviting space. A large back deck extends the living room space and provides a wonderful setting for relaxing, dining and enjoying the privacy of the property. The half-bathroom completes the main level. The second floor has two bedrooms, an area that could be used as an office and one full bathroom. This distinctive Millb

This expansive country residence offers far more than meets the eye, combining generous living spaces, timeless character, and remarkable potential. Oversized windows bathe the home in natural light, illuminating hardwood floors and 9-foot ceilings throughout. An inviting rear porch provides a private retreat, perfect for relaxing and enjoying the tranquil setting. Beautiful arched openings create an effortless flow between the living room with a wood-burning fireplace, dining room, and kitchen. At the heart of the home is a dramatic Great Room featuring a floor-to-ceiling brick Rumford wood-burning fireplace, soaring wood-clad ceilings, and direct access to the porch, creating an ideal space for gathering and entertaining. The chef's kitchen is thoughtfully designed with a six-burner gas range, abundant cabinetry, and a pantry for additional storage. The spacious primary bedroom includes a walk-in closet and an adjoining partially finished area ready for completion as an ensuite bath.

Village of Red Hook home is located in Red Hook Estates. This property is situated with a private back yard that has a deck that wraps around to the backyard. Perfect for all your barbeques and the yard is ideal for all your outside activities. This home is well maintained and has updated appliances and updated bamboo flooring. The kitchen has a sliding glass door that over looks your back yard. A side door gives you access to the back deck. There are 3 bedrooms that are very spacous with windows that let in lots of bright lights. The bathroom has an updated fixture, sink an toilet. There is a full basement for storage that could be updated for future living space. There is room for a future garage if so desired. The heating is electric and is a hybrid electric hot water heater with a heat pump. There are 18 solar panels on the roof and the system is A 6 KW system. This home in Red Hook is walking distance to many businesses. The village offers many ameinities from garbage pick up to m

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

Cozy cottage charm in the village of rhinebeck! Sometimes the best things come in smaller packages! Situated on a generously sized corner lot along a quiet, low-traffic Village street, this quaint 1940 Cape Cod offers the perfect blend of charm, comfort, and possibilities. Inside, you’ll find a cozy living room, separate dining area, kitchen, 3 bedrooms, and a full bath. An enclosed front porch adds a touch of old-fashioned charm, while the large deck off the kitchen is perfect for outdoor dining, entertaining, or simply relaxing. The property also features a detached 1.5-car garage, good mechanical systems, and municipal water. Whether you’re looking for a comfortable year-round residence, a weekend Hudson Valley getaway, or a place to make your own, this little gem offers plenty to love. Enjoy all the charm and character of Rhinebeck Village, with its wonderful restaurants, unique shops, and vibrant community. Possible seller financing available for qualified buyers!

73 Birch Road on Robinson Pond in Copake, New York. This wonderful retreat is situated on one of the largest parcels in the private Taconic Shores Property Owners Association (lots 648, 649, and 650.5), a private lake community, 2 beaches, shared community areas, multiple boat launching areas. Built in 1960 and remodeled over the years, this 3-bedroom, 2-bath ranch home (noted in public records as 2-bedroom, 1-bath) features an open-concept with Great Room with a wood stove. It includes an attached four-season enclosed sunroom with a glass ceiling, tiled floors, laundry facilities, and ample storage. The first floor offers two bedrooms and a bathroom, while the walkout basement includes a living room with another woodstove, an office or additional bedroom, another two rooms for storage or additional living areas, a 3/4 bath, and a mechanical room. The exterior is equally impressive, featuring manicured gardens, a handmade stone water fountain, and a large deck off the dining area. Addi

Discover the quiet charm of Millbrook Hunt Country, where three picturesque acres of sweeping lawns bordered by mature trees offers a private country setting just moments from the Village of Millbrook. N. Mabbettsville Road is among the finest locations in the area, known for its spectacular landscapes, beautiful scenery, gorgeous sunsets and blissful serenity. With comfortable one-level living and easy access to village shops, restaurants, and amenities, this property is equally appealing as a full-time residence or a weekend retreat. The interior features hardwood floors, a brick fireplace with a wood-burning insert, and an easy flow between living spaces. The stylish kitchen and dining area connect seamlessly to the living room, while a wide opening leads to a sunroom overlooking the private side yard. The layout includes a primary bedroom, two additional bedrooms, a family room, and two full, updated bathrooms. A walk-up attic and full, unfinished basement offer ample storage, comp

Beautifully maintained three-bedroom cottage overlooking the scenic Harlem Valley Rail Trail in the charming town of Amenia. This move-in-ready home has been thoughtfully updated with new electric, new windows and new insulation, improvements that offer comfort and peace of mind for years to come. Pride of ownership is evident throughout the well maintained interior and exterior. Step outside and enjoy the tranquil setting with direct views of the Harlem Valley Rail Trail, perfect for walking, biking and enjoying the natural beauty of the surrounding countryside. A spacious 10' x 16' utility shed offers excellent storage for tools, outdoor equipment or recreational gear. Whether you're looking for a full-time residence or the perfect weekend retreat, this inviting home is sure to impress. A wonderful opportunity to own a turnkey home in one of Dutchess County's most picturesque communities. 24 Rail Trail Way is a rare opportunity not to be missed

Set on the shores of Copake Lake, this charming waterfront home blends classic lake character with thoughtful modern updates. Offering three bedrooms and 1.5 baths, the home features a bright open kitchen, living, and dining area designed for easy lake living and entertaining. Recent renovations, including HVAC, septic system, and expansion to main floor, bring fresh style and comfort while maintaining the cozy charm expected from a lakeside retreat. French doors open to a spacious deck overlooking the water, creating a seamless connection between indoor living and the peaceful lake views beyond. Just steps from the deck, enjoy your private shoreline and dock-perfect for swimming, boating, and relaxing by the water. Copake Lake is one of the area's only fully motorized lakes, ideal for water sports, fishing, and sunset cruises. Conveniently located near Copake Country Club and Catamount Mountain Resort, and under 30 minutes to both Amtrak and Metro-North rail service, as well as the vi

1890 bones. 1970's soul. Rhinebeck Village at your doorstep! Originally built circa 1890 and reimagined in the 1970s, this character-filled home blends its late-19th-century origins with the warm, rustic spirit of a Hudson Valley retreat. Exposed timbers, wide-board wood floors, vaulted wood ceilings and abundant natural light provide a wonderful foundation for a thoughtful renovation. Surrounded by mature trees, the property feels surprisingly private while offering true village walkability. Stroll to Rhinebeck’s restaurants and boutiques, catch a film at Upstate Films or spend an afternoon at Mirbeau Inn & Spa. Rhinecliff Amtrak and Bard College are both a short drive away. Additional lot located at the front of the property-47 Oak Street is included in the sale, which brings the total property to. 50 acres. The ingredients are here: history, character, privacy and the rare pleasure of Rhinebeck Village living

Classic Brick One-Level Home situated on level, park-like grounds with open lawns, mature trees, and woods. This listing includes a separate 2.7 acre wooded parcel on Nine Partners Lane, Tax ID: 135801-6765-04-769-) adjacent to the 4.5 acres that surrounds this beautiful home. 3 Bedrooms + a Den or Office, with closet, that extends into a sunroom with private entrance offers privacy while working, studying or crafting. Full, Walk-Out Basement with Full Bath and Full Walk-up Attic offers lots of opportunities. Expansive Deck across the entire rear of the home overlooks the backyard. Detached 2 car garage with loft storage and endless possibilities. Close to Golf; Equestrian Facilities; Village of Millbrook shops, restaurants, library and more; Public and Private Schools; Dover and Wassaic Train Stations. All information is deemed reliable but not guaranteed. All dimensions, measurements and listing details should be independently verified by the purchaser and/or purchaser's broker

Lots of potential here! This comfortable Ranch home is a rare affordable opportunity in Rhinebeck. Only minutes from the village and Amtrak on approximately ½ acre, this home boasts 3 bedrooms, two baths with radiant floor heating, a very spacious living room, separate dining room, eat in kitchen with ample cabinets and charming family room with fireplace Amenities include gleaming hardwood floors. Village water. Taxes reflect a senior exemption

In a premier location on a quiet road in Millbrook Hunt country, this unique property of 100 acres offers a picturesque setting of open fields, ponds, stonewalls, mature trees and beautiful views of the surrounding countryside as nature entertains one daily with abundant wildlife. Proudly maintained, protected and in conservation, Shooter’s Hill is an exceptional offering and an unparalleled opportunity to own and enjoy the tranquility of this magical sanctuary, yet only minutes from the Village of Millbrook, clubs, schools and other amenities. Nestled on a hillside, this four bedroom, three bath home overlooks expansive lawns, perennial and specimen plantings, pastures, three masterly designed stepping ponds, and protected woodlands laced with extensive trails to include those of the Millbrook Hunt. Completing the homestead is a wonderful two-story barn with an artist studio and a two-room office building with a three-car garage. Contiguous to Bontecou Wildlife Conservation Preserve o

Set on a large, private lot with scenic views in beautiful Copake, NY. This inviting Ranch offers two bedrooms and a full bath on the main level, while the private primary bedroom is located on the second floor, complete with its own bathroom creating a peaceful retreat with added privacy. The open concept dining and kitchen area create a great space for entertaining. The spacious light filled living room leads to the partially finished basement, offering flexible space for a home office, recreation room or additional living. Step out onto the spacious deck and enjoy the large fenced in private yard, perfect for relaxing, entertaining, or simply taking in the peaceful Hudson Valley setting. A one car garage provides plenty of room for your vehicle and additional storage. Just a short distance to the Copake town park, center of town, Copake Lake and Bash Bish Falls. Only 25 minutes to vibrant Hudson and Great Barrington for shopping and dining

Set on eight private acres just outside the Village of Germantown, 150 Round Top Road is a thoughtfully designed contemporary home that blends seamlessly with its quiet, wooded surroundings. Built in 2023, the home is clad in cypress wood and natural stone and features a heated in ground pool, perfect for summertime. Inside, soaring 12 foot ceilings and ample windows allow natural light to illuminate the home, especially the open kitchen and upstairs living space. Anchored by a floor to ceiling Venetian stucco fireplace, the upstairs living space opens onto the oversized kitchen, with painted slab cabinetry, walnut accents, quartz countertops, and generous space for cooking, gathering and entertaining. The deck, located off the great room, is perched among the surrounding trees, integrating the home with its beautiful setting. The primary suite is also on this level, with a walk-in closet and an en-suite bathroom with an oversized, walk-in shower and radiant heat. Two additional bedroo