52 houses for sale in Stissing

Welcome to historic Stissing hamlet in Stanfordville NY within bucolic Dutchess County. This Circa 1875 side hall Colonial is charming and spacious. Set on 4.1 acres, the property is inviting and tranquil. The front door opens to a foyer stretching the entire width of the home to the back entrance additional foyer. There are beautiful wide-board hardwood floors throughout the main living space. The open living room nicely connects to the formal dining room with period pocket doors. The extra cozy and bright country kitchen features an oversized brick wood-burning fireplace with mantle. Windows galore overlooking the lawn, and recessed lighting make this a cheerful room to spend time in. There is a covered stone porch off the kitchen entrance as well. A half bath with washer/dryer is also on this level. Upstairs off the landing are four bedrooms and two full bathrooms. The walk-up attic is accessed here as well. A second staircase goes back down to the kitchen area. Outside the property

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

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

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

Looking for a Dutchess County home with acreage, mountain views, guest accommodations, and flexible living space? Set on 5.16 acres in Stanfordville, this one of a kind property offers nearly 2600 square feet of living space along with an expansive outdoor oasis, multiple outbuildings, and separate accommodations currently used as an Airbnb. Inside the 4 bedroom, 2.5 bath main home, a spacious kitchen offers abundant cabinetry, generous counter space, stainless steel appliances, and a large peninsula. Multiple living and dining areas and a dedicated home office provide room to spread out, while a wood-burning stove framed by an exposed brick wall creates a distinctive gathering space with direct access to the expansive back deck. Upstairs you will find 4 spacious bedrooms, including a primary suite with a private bath and balcony. The apartment is above the detached 2 car garage, with a separate exterior entrance, separate utilities and dedicated elevated deck, creating added separatio

Privately set on 4 acres, find this one bedroom cabin ideal for a weekend retreat. Attractive open floor plan includes updated eat-in kitchen complete with cathedral ceiling & living room w/wood stove and hardwood floor. Generously sized bedroom with two closets & tile bathroom. Relax on the covered front porch or the large deck overlooking the expansive backyard. Recent improvements include spray foam insulation, water heater & well pump. Property also includes 20 x 30 building, which lends itself to artist's studio space, wood shop, fitness area or storage. Secondary shed with ample space for all maintenance equipment. Surrounded by wooded buffers for total privacy yet just minutes from the Taconic State Parkway for easy access. Centrally located for a simple commute to local amenities such as the Village of Millbrook & Village of Rhinebeck. This outdoor enthusiast's paradise will surely impress

Rarely does an offering of this magnitude become available in the Hudson Valley. Encompassing more than 137 acres across three parcels, this extraordinary farm presents a unique opportunity to create a compound with a main residence, and three other unique residential spaces spread across two barns and a caretaker's cottage. Restore and reimagine a legacy country estate in one of the region's most desirable locations. At the heart of the property is a classic 1910 Colonial residence offering over 4,000 square feet of living space. Rich with original character, the home showcases wide-board floors, original doors and hardware, and timeless architectural details throughout. The gracious floor plan includes a kitchen, den, formal dining room, living room, and sunroom, along with a ground-floor primary suite. Upstairs are three additional bedrooms, two full bathrooms, and an office. Three-zone heating and cooling provide year-round comfort. The grounds are equally impressive, featuring a 4

Presenting Hunns Lake House, an inviting country home set along the shores of Hunns Lake, a private residential lake tucked into the countryside of Stanfordville. The property features 150 feet of lakefront and beautiful water views from nearly every room, including a striking glass-enclosed dining room that looks out over the lake. With no motorboats permitted, lake life here is truly irresistible. Enjoy morning swims, afternoons kayaking or paddleboarding, and long evenings watching the light move across the water. Built in 1960, the three-bedroom, two-bath home offers an expansive 3,688 square feet, all on one level. Generous rooms and abundant windows fill the house with natural light. The glass-enclosed dining room opens directly into the living room, where a beautiful stone fireplace brings warmth and character. The large country kitchen centers around an island with plenty of room to cook and gather, while an incredibly spacious family room with a wood stove offers another place

Move right into this newly renovated 3 bedroom home in the charming town of Stanford. The open floor plan features one level living at its finest. Completely renovated from top to bottom in 2026, it is so fresh, the paint is still drying. Featuring a new roof, newly paved driveway, new gutters and gutter guards, new oak floors, new kitchen with island and Quartz countertops. All new appliances, including full size washer and dryer. The property is freshly landscaped, featuring new bluestone walkways and a back patio. Sunlight fills every window of this home, while everything is right within reach. Enjoy your morning coffee on the sun filled porch with all new tile beneath your feet. Looking out on your private back yard within one acre of land, and your refreshed two car garage, featuring closed-foam insulation and new metal roof, along with new doors and windows. All you need to bring is your furniture and your belongings. Convenient location 15 minutes from Millbrook, Rhinebeck or Pi

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

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

Tucked away on 18+ acres off a designated scenic road sits this bright and charming country cottage. A long driveway leads to the cottage offering complete privacy with mature trees, wildlife, stone walls and a seasonal pond. This home has just undergone a total exterior renovation including new Marvin windows, Hardie Board siding, and insulation. Inside you will find polished concrete floors with radiant heat creating warmth throughout, custom cabinets and black walnut countertops, a Harman pellet stove, and separate wood burning fireplace. Comfortably live on the first floor with its cozy bedroom adjoining the European style bathroom with a vintage, cast iron clawfoot tub. The lofty and serene upstairs is currently configured as one spacious room but can easily be converted to two bedrooms with a bath. The cottage offers the flexibility to serve as a charming guest house should a future main residence be built. Immerse yourself in the peace and natural beauty of this rare property, w

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.

3BR/1BA w/ 50 FT LAKE FRONTAGE STANFORDVILLE/HUNNS LAKE Enjoy the wonderful lake life at beautiful Hunns Lake in Stanfordville. Over 50 feet of lake frontage brand new to market. At this home, the sun rises in your kitchen & sets in your living room! Stunning lake and sunset views from multiple areas throughout this home. Open kitchen with wood burning stove and large center island offers dining with lake views! Entertain your guests with a lovely back patio setting or scenic sunsets over the lake while relaxing in the living room. Beautiful interior design includes hardwood floors throughout, lovely rustic wood work decor w/ country & tile, wine racks & extra large fish tank if desired. Central location to Millbrook, Rhinebeck, Pine Plains & Millerton. A nature & lake enthusiasts paradise. Whether your fishing, boating, kayaking, ice fishing, ice skating, or enjoy a nice, quiet walk around the lake, this wonderful community will greet you with a smile. Perfect for primary residence or

Zoned commercial/residential, full of character with beamed ceilings, and set on 1.1 acres, this classic 1943-built Colonial home, approximately 1,400 sq ft, offers 3 bedrooms and 1 bath, with an enclosed back porch that's a perfect place to work from home or relax anytime of the day or evening. The unfinished basement with outside entrance provides excellent storage and houses the washer and dryer. A standout feature of this property is the detached garage built in 1992, a spacious 2,040 sq ft structure with room for up to 3 vehicles. Currently used for auto repair and miscellaneous activities, it also includes an unfinished attic for additional storage or expansion potential. Whether you're a car enthusiast, hobbyist, or in need of a workshop, the garage is a rare find and has tons of parking! Conveniently located in Stanfordville, NY, this property blends small-town charm with practical space and versatility, and provides a wonderful opportunity for those seeking a home with charact

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

A rare opportunity to own a piece of historic Clinton Corners, this distinctive home began life as an 1800s barn before being carefully relocated to its current setting in the 1970s. The original structure retains the character and craftsmanship of a bygone era, while the home has been thoughtfully updated with the modern systems and amenities expected for comfortable year-round living. Set on a quiet, tranquil country road, the home offers three finished levels of living space, creating a flexible layout with plenty of room to live, work, and gather. Historic details and old-world charm are balanced by a thoughtful collection of modern improvements, including a brand-new water filtration system, pellet stove, updated furnace, on-demand hot water, whole-house generator, covered garage, and paved driveway. Just minutes from the Taconic State Parkway and the heart of Rhinebeck, the property offers an easy connection to one of the Hudson Valley's most beloved villages. Downtown Rhinebeck

A Hudson Valley property with room to live, gather, and grow. Set on 2.27 acres this substantial 2006-built residence offers an uncommon combination of space, flexibility, and Hudson Valley lifestyle. With approximately 3,500 square feet of total living space, four bedrooms, three full baths, and two half baths, the property is designed for a lifestyle that extends well beyond the traditional home. A defining feature is the approximately 1,700-square-foot in-law suite, offering an exceptional degree of versatility and independence. Whether envisioned for multigenerational living, extended family, private guest accommodations, a work-from-home environment, or a combination of uses, this expansive additional space provides possibilities rarely found in the Hudson Valley market. The main level offers generous proportions and an inviting everyday flow. A large kitchen and dining area open toward the living space and extend outdoors to a back deck, creating an easy setting for both relaxed

Introducing the Upton House, where the easygoing spirit of a 1970s country home meets a beautifully considered modern sensibility. Behind its familiar white facade, a world of warm woods, sculptural forms, and richly textured materials unfolds, creating a home that feels at once nostalgic and entirely of the moment. There is an inviting simplicity to it all, a quiet celebration of the everyday rituals that make a house feel like home. Inside, natural oak, soft earthy tones, and an abundance of sunlight create an atmosphere of understated warmth. Vaulted ceilings rising to twelve feet bring an unexpected sense of volume to the main living spaces, while a generous bank of windows frames the surrounding greenery. At the heart of the living room, a wood-burning stove is set against softly variegated tile, flanked by custom oak shelving and delicate slatted millwork. The interplay of natural textures lends the space an architectural richness without sacrificing its relaxed, welcoming charac

ZONED COMMERCIAL/RESIDENTIAL, full of character with beamed ceilings, and set on 1.1 acres, this classic 1943-built Colonial home, approximately 1,400 sq ft, offers 3 bedrooms and 1 bath, with an enclosed back porch that's a perfect place to work from home or relax anytime of the day or evening. The unfinished basement with outside entrance provides excellent storage and houses the washer and dryer. A standout feature of this property is the detached garage built in 1992, a spacious 2,040 sq ft structure with room for up to 3 vehicles. Currently used for auto repair and miscellaneous activities, it also includes an unfinished attic for additional storage or expansion potential. Whether you're a car enthusiast, hobbyist, or in need of a workshop, the garage is a rare find and has tons of parking! Conveniently located in Stanfordville, NY, this property blends small-town charm with practical space and versatility, and provides a wonderful opportunity for those seeking a home with charact

Privately set on 32 extraordinary acres in the heart of Shekomeko, this light-filled country retreat captures sweeping views of Stissing Mountain and the Catskills from nearly every vantage point. A long drive winds through the landscape to a thoughtfully sited three-bedroom, two and a half bath residence featuring vaulted ceilings, expansive windows, a wood stove, and exceptional southern, western, and northern exposures. The 2,250-square-foot home includes a large porch, an outdoor shower, and an attached two-car garage, offering comfortable living amid complete tranquility. Equally compelling is the land itself—an exceptional setting for recreation, privacy, and even a future build for a larger main residence while retaining the existing home as a guest residence. A rare opportunity to own one of Shekomeko's most scenic properties, where dramatic views, acreage, and endless potential converge. 1504 Route 83 is conveniently located; minutes to Mashomack, 10 minutes to Pine Plains and

Presenting Hunns Lake House, an inviting country home set along the shores of Hunns Lake, a private residential lake tucked into the countryside of Stanfordville. The property features 150 feet of lakefront and beautiful water views from nearly every room, including a striking glass-enclosed dining room that looks out over the lake. With no motorboats permitted, lake life here is truly irresistible. Enjoy morning swims, afternoons kayaking or paddleboarding, and long evenings watching the light move across the water. Built in 1960, the three-bedroom, two-bath home offers an expansive 3,688 square feet, all on one level. Generous rooms and abundant windows fill the house with natural light. The glass-enclosed dining room opens directly into the living room, where a beautiful stone fireplace brings warmth and character. The large country kitchen centers around an island with plenty of room to cook and gather, while an incredibly spacious family room with a wood stove offers another place

This cozy Craftsman-like country cottage is located on beautiful Hunns Lake Road in bucolic Dutchess County. Many recent upgrades make this more than move in ready. Situated high off the road, the house is bright with sunlight. The entrance is charming with a covered porch, trex flooring and new doorway. Hardwood floors are throughout the home. This Two Bedroom + Bonus Room retreat is all on one comfortable level. The open, easy floor plan flows nicely from Living and Dining. There is a brick fireplace with mantle flanked by two windows that anchors the living room. The renovated chefs kitchen is delightful with all new custom cabinetry, appliances, sink and fixtures. Recessed lighting is nicely installed throughout the home. A newly renovated full bathroom is smart and tasteful. The primary bedroom also has a full bathroom set up, however has not been built out yet. Outside features a two car garage, mature lawns, and stone patio. The back and side yards have nice buffer of trees and

Hidden at the end of a long, winding drive, The Sprucewood sits within 6.95 acres of mature woodland in the rolling countryside of Dutchess County. The approach is part of the experience: the road narrows, the trees close in, and somewhere along the way the outside world seems to fall away. Then the home appears, completely private, surrounded by forest and without another home in sight. Recently renovated from top to bottom, the four-bedroom, three-and-a-half-bath house has the easy, unstudied character of a place meant to be lived in. Warm woods, natural textures, and a quiet palette give the interiors a sense of calm, but it is the scale and flow of the rooms that make the house especially great for gathering. At its heart is an expansive eat-in kitchen with room to comfortably seat twelve or more around the table. A massive fieldstone fireplace forms the backdrop, opening on both sides to connect the kitchen with the sunken living room beyond. Firelight moves between the two spaces

Set high on a private hilltop along a designated scenic road, this exceptional country estate commands sweeping views over open fields, ponds, and the rolling hills of the Hudson Valley. South-facing and surrounded by nature, the property offers a rare sense of privacy and seclusion, yet is just eight minutes from the village of Millbrook, approximately 12 minutes from Pine Plains and 17 minutes from Rhinebeck. The landscape reveals itself the moment you enter the main residence. From the front foyer, the eye is drawn directly through the house to broad expanses of glass framing the countryside beyond. Large glass doors open onto an expansive terrace, creating a natural connection between the interiors and the remarkable setting. Designed to take full advantage of its hilltop position and southern exposure, the house is filled with natural light throughout the day. The gracious single-level floor plan makes everyday living effortless, with rooms that flow easily while maintaining a sen

Space, privacy, and possibility in the heart of Clinton Corners! Set on approximately 3.3 acres, this expansive two-family home offers nearly 4,000 square feet of living space and an exceptional blend of versatility and Hudson Valley charm. The main residence features 3 bedrooms and 2 bathrooms, with a generous layout that lives larger than most homes. A welcoming formal entry leads into an inviting open-concept living space where the kitchen, dining area, living room, and den flow seamlessly together—perfect for relaxed everyday living and effortless entertaining. Step outside onto the spacious deck for alfresco dining, sunset gatherings, or quiet mornings with coffee. Down the hall, two generously sized bedrooms accompany a private primary suite with its own ensuite bath. The lower level offers an impressive 2-bedroom, 1-bath apartment with a large kitchen and living room, creating an ideal setup for guests, extended family, or rental income. A two-car garage and dedicated workshop s

Welcome HOME to this spacious 3-bedroom, 2-bath ranch nestled on nearly 4 picturesque acres in the scenic countryside of Stanfordville! Offering over 1,500 sq. Ft. of living space, this home features a bright and inviting living room with hardwood floors, an exposed wood beam, and plenty of natural light. The eat-in kitchen offers ample cabinet space, a separate dining area, and a large walk-in pantry. The primary bedroom features its own private full bath, while a second full bath serves the two additional bedrooms. The lower level offers a playroom/family room with sliding glass doors leading to the rear deck, a separate laundry area, and additional storage space. An oversized garage provides plenty of room for vehicles, equipment, or hobbies. Enjoy the peaceful surroundings from the rear deck or front porch. With a functional layout and spacious rooms, this home offers a canvas to add your own style, personal touches, and updates to make it truly your own!

Sited on just less than 10 picturesque acres along a country road in Clinton Corners, this inviting 1969 home offers generous living spaces, beautiful natural surroundings, a spring fed pond and a small horse barn. Hardwood floors and generously proportioned rooms create a warm and comfortable atmosphere throughout this 3-bedroom 2.5 bath home consisting of 1,932 finished square feet. A large picture window in the living room frames beautiful views of the meadow and surrounding trees, bringing the landscape indoors as does the light-filled three-season room which is especially charming, with windows on three sides. The lower-level provides an office, combo laundry /bathroom and the family room which offers an inviting retreat with both a pellet stove and wood stove—perfect for cozy gatherings and relaxed evenings at home. The attached oversized garage is also accessed through the lower level. Outside, the nearly 10-acre property offers room to enjoy the changing seasons. Bring the hors

Hudson Polo Farm, 729 Cold Spring Rd offers a Rare 130-Acre Stanfordville Domain & Proposed 8-Lot Luxury Subdivision Opportunity Spanning 130 contiguous acres in prime Northern Dutchess horse country, The Hudson Polo & Equestrian Farm presents an extraordinary dual-opportunity: a world-class sporting estate paired with an active, high-yield residential development project. The rear 100 acres are currently in the process of subdivision into eight premier 8 to 10-acre private residential parcels. Positioned in a market with strong demand for high-end second homes, these elevated, private sites offer Hudson Valley views and exceptional natural privacy. With projected end-state luxury homes commanding 3,000,000+ each, this offers an incoming developer or investor a turnkey pathway to 24M+ in gross residential inventory. The front 30-acre anchor features full equestrian infrastructure including a 46 stall show barn, indoor arena, practice polo field, and fenced pastures, along with'The Geor

Opportunity awaits in the heart of Pine Plains! This 3-bedroom, 1-bath manufactured home, built in 1976, is set on a spacious 0.53-acre lot within the Pine Plains Central School District. Offering 792 square feet of living space, the property presents a wonderful opportunity for a buyer or investor looking to update and personalize a home to suit their vision. The generous lot provides space to enjoy the outdoors while the convenient location offers easy access to local schools, village amenities, dining, shopping, and the surrounding Hudson Valley countryside. Whether you're looking for a project, an investment, or a chance to create a home in a charming community, this property offers plenty of potential