57 properties for sale in Stissing

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

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

Sisters Hill Farm - A Rare Legacy Estate in the Heart of the Hudson Valley Welcome to Sisters Hill Farm, an extraordinary 66-acre country estate where history, stewardship, and opportunity come together in one exceptional offering. Set amidst rolling fields, mature woodlands, and breathtaking pastoral views, this remarkable property offers a rare opportunity to own one of the region's most iconic farm estates. At the heart of the property stands a magnificent turn-of-the-century farmhouse that captures the elegance and craftsmanship of a bygone era. Rich in architectural detail, the multi-bedroom residence has been lovingly maintained and showcases impressive period character throughout. A grand stone fireplace anchors the home's welcoming living spaces, complemented by stunning handcrafted woodwork and intricate trim. Large windows frame sweeping views of the surrounding farmland, gardens, and mature trees creating a peaceful connection to the landscape in every season. The estate als

Sisters Hill Farm - A Rare Legacy Estate in the Heart of the Hudson Valley Welcome to Sisters Hill Farm, an extraordinary 66-acre country estate where history, stewardship, and opportunity come together in one exceptional offering. Set amidst rolling fields, mature woodlands, and breathtaking pastoral views, this remarkable property offers a rare opportunity to own one of the region's most iconic farm estates. At the heart of the property stands a magnificent turn-of-the-century farmhouse that captures the elegance and craftsmanship of a bygone era. Rich in architectural detail, the multi-bedroom residence has been lovingly maintained and showcases impressive period character throughout. A grand stone fireplace anchors the home's welcoming living spaces, complemented by stunning handcrafted woodwork and intricate trim. Large windows frame sweeping views of the surrounding farmland, gardens, and mature trees creating a peaceful connection to the landscape in every season. The estate als

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.

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.

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

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 compound presents a unique opportunity to 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 40' x 18' gunite pool, a tennis court, and a picturesque 2.5-acre pond complete with a fountain. Equestrian and agricultural a

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

Welcome HOME to this charming farmhouse cottage, originally built in 1853 and was Schoolhouse number nine, one of clinton's original schoolhouses! Nestled on over an acre of picturesque, level property in the highly sought-after Pine Plains School District, this one-of-a-kind home offers 2 bedrooms, 1.5 bathrooms, and 1,320 square feet of comfortable living space surrounded by mature trees and peaceful countryside. Rich in history and timeless character, the home features hardwood floors, soaring ceilings, oversized windows that fill the home with natural light, and a spacious living room centered around a cozy wood stove with a wet bar. The generously sized country kitchen offers abundant cabinetry, extensive counter space, and a bright dining area overlooking the backyard. The flexible floor plan includes two first-floor bedrooms, a full bathroom, and an additional half bath, providing the convenience of one-level living. A full walk-up attic offers exceptional storage and exciting p

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.

Perched atop 40.9 private acres, this exceptional custom-built estate offers unrivaled privacy and sweeping panoramic views of the Catskill Mountains. Blending timeless craftsmanship with modern luxury, this hilltop retreat embodies refined living in a breathtaking natural setting. Inside, antique teak flooring flows throughout the home, adding warmth and character to every space. The open floor plan features a gracious living room that opens to a library with a fireplace and a full bath, creating an inviting centerpiece for both relaxation and entertaining. At the heart of the home, the eat-in kitchen is both functional and striking, featuring a scullery and a distinctive modern Rumson fireplace. The kitchen opens effortlessly onto a stone terrace and pergola, offering a breathtaking setting for alfresco dining while overlooking beautifully landscaped gardens that evolve with the changing seasons. Adjacent, the formal dining room provides a refined space for hosting memorable gatherin

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

Welcome to your private retreat in Clinton. Set on over 24 acres across two separate parcels, this exceptional 4-bedroom, 3.5-bath property has been extensively renovated and thoughtfully upgraded throughout, with improvements to the residence, pool area, and grounds. The main floor of the residence features wide-plank wood flooring, beamed ceilings, an open kitchen with stainless steel appliances and counter seating area, a dining area with two exposures of windows, a dramatic open staircase, and a living room anchored by a double-height stone wood-burning fireplace. Sliding doors open to a spacious deck with unobstructed views of the brook and surrounding mature trees. The primary suite is a serene sanctuary, featuring a custom walk-in closet and a beautifully renovated, spa-inspired bathroom with double vanity, fully tiled steam shower, and deep soaking tub. Sliding doors provide access to the backyard and pool area beyond. A powder room and a pantry/laundry room complete this level

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

Hidden at the end of a long, winding drive, The Sprucewood sits within 7 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, c

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

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

Set privately on nearly 35 acres just minutes from the Village of Millbrook, this exceptional country estate offers timeless architecture, refined craftsmanship, and sweeping western views to the Catskill Mountains. Thoughtfully designed for both elegant entertaining and comfortable everyday living, the 5,206 square foot residence captures extraordinary sunsets. A long private approach leads to the beautifully sited home, where classic proportions and understated sophistication define the interiors. The first floor features 9’6” ceilings, wide board oak floors, and crown molding throughout. Gracious living spaces include a living room with fireplace, custom built-in bookcases, integrated speakers, and French doors opening to a spacious covered porch overlooking the grounds and pool. The inviting family room and sunroom each offer their own fireplace, creating warm and welcoming spaces year-round. At the center of the home is a beautifully appointed chef’s kitchen with quartzite counter

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

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!