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$330,000
2 Beds ⋅ 1 Baths ⋅ 1033202 MLS
Charming two-bedroom lake cottage in the Twin Lakes community of Elizaville, offering a peaceful setting and inviting views of South Twin Lake. This approximately 892-square-foot home features two bedrooms, one full bath, a comfortable single-level layout, abundant natural light, and a full unfinished basement providing valuable storage and future possibilities. Enjoy lake access and the relaxed character of a classic country retreat, ideal for year-round living or a weekend getaway. The property is serviced by a private well and septic system and is conveniently located within the Pine Plains Central School District. A wonderful opportunity to enjoy lake-community living in scenic Columbia County.

34 Shore Drive, Elizaville
$525,000
2 Beds ⋅ 2 Baths ⋅ 1031285 MLS
Beautifully renovated home privately set on a scenic, park-like property, offering the perfect blend of privacy and convenience—Located on the Dutchess/Columbia line just 2 minutes to the Taconic State Parkway for an easy commute. This move-in-ready home is filled with natural light and showcases high-end finishes, designer touches, and thoughtful updates throughout. The chef's kitchen features quartz countertops, stainless steel appliances, custom cabinetry with pantry, floating shelves, soaring ceilings, built-in bench seating, an additional wall of cabinetry for exceptional storage, and access to the patio and backyard—ideal for indoor/outdoor living. The lovely living room is highlighted by oversized windows, sliding glass doors leading to a partially covered deck, recessed lighting, and a beautifully remodeled powder room with board-and-batten accents. Upstairs, the primary suite offers vaulted ceilings, oversized windows, and a walk-in closet with custom organizers. The spa-inspired full bath features a double vanity, an oversized luxury walk-in shower, and a stylish barn door entrance. A generously sized second bedroom includes a large closet. Additional features include central air, main-level laundry, recessed lighting, and quality finishes throughout. Outside, enjoy complete privacy surrounded by mature landscaping, established perennial gardens, raised garden beds, a large storage shed, and a separate studio/barn offering endless possibilities for a workshop, art studio, or hobby space (needs work). Conveniently located near state parks, hiking, skiing, and other Hudson Valley recreational opportunities, just 2 mins to the Taconic State Parkway, 20mins to Metro-North. Also nearby are sweet shops, restaurants, wineries, and equestrian estates that define the Hudson Valley lifestyle, this turnkey estate presents a rare opportunity to own an exceptional private retreat where luxury, recreation, and nature exist in perfect harmony.

10 Dickman Farm Road, Red Hook
$445,000
3 Beds ⋅ 2 Baths ⋅ 1029261 MLS
Tucked away off the main road, this property is situated on a private road near Hunns Lake. The former fishing cottage is cozy and quiet on 1.2 acres, with mature trees, lawns and meadows with western sunset views. The entryway leads to a windowed sitting room which opens up to the main pine paneled living room, lined with an oversize picture window with sliders. A stone wood burning fireplace with insert provides a great centerpiece and two cords of wood are ready for next season. Flooring is currently painted with a striping trim. Double pane thermal windows with screens are throughout the house. The open country kitchen has wide plank pine floors and countertops with plenty of cabinet storage. The dining area includes two sets of glass slider doors leading out to the spacious two level Trex redwood decking overlooking the pool. A deluxe propane grill with oven and burner is also included. There is a full bath with double sink and tub with shower in addition the laundry. A one car garage is also on this level. Upstairs is the primary bedroom with multiple window exposures. A brand new full bathroom features a beautiful soaking tub. There are two more bedrooms/office also having two window exposures. Furnace, Oil Tank, Water Heater and Pool Pump are new from 2025. The property on one side and the rear is buffered by wide open land/forest. 50 acre Hunns Lake is nearby, and is a great 2 ½ mile walk around it. This is nearby to the villages of Millbrook, Pine Plains, Rhinebeck, Millerton and more. All provide shopping, dining, and overall country recreation. The Wassaic Metro North train station is just 18 minutes away; all this just two hours from NYC. Welcome to the Hudson Valley!

26 Hunns Lake Place, Stanfordville
$350,000
2 Beds ⋅ 1 Baths ⋅ 1022019 MLS
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 potential for future expansion. Step outside to the oversized rear deck overlooking the sprawling backyard, ideal for entertaining, gardening, or simply enjoying the tranquil setting. The property also features a detached one-car garage, multiple storage sheds, and an expansive level lawn with plenty of room for recreation, hobbies, or future improvements. Whether you're searching for a full-time residence, a weekend getaway, or a piece of Hudson Valley history, this rare property offers historic charm, endless potential, and an unbeatable location just minutes from Rhinebeck, Millbrook, Pine Plains, wineries, farm markets, hiking trails, and everything the Hudson Valley has to offer. Some photos have been digitally staged.

357 Pumpkin Lane, Clinton Corners
$4,480,000
3 Beds ⋅ 4 Baths ⋅ 1028057 MLS
Perfectly positioned atop more than 54 breathtaking acres in the heart of the Hudson Valley, this inviting country retreat offers exceptional privacy and sweeping natural beauty. Thoughtfully designed to embrace its spectacular setting, the home features an open, light-filled floor plan that flows effortlessly between the living and dining spaces, creating an ideal environment for both intimate gatherings and gracious living. Soaring ceilings, expansive windows, and glass doors bathe the interior in natural light while capturing picturesque views of the surrounding landscape throughout the seasons. At the heart of the home, the living room is anchored by a striking stone fireplace, creating a warm and welcoming gathering space. Thoughtfully equipped for year-round comfort and peace of mind, the home also features central air conditioning and a whole-house generator. The main level includes a serene primary suite, offering the ease of single-level living. Upstairs, two additional bedrooms and a full bath provide comfortable accommodations for family and guests, each enjoying peaceful views of the surrounding landscape. The walkout lower level offers exceptional versatility, with ample space for a family room, fitness area, artist’s studio, or home office, along with a spacious laundry area and abundant storage. Outside, the property’s remarkable acreage invites endless exploration. Wander through open meadows to a tranquil stream, observe abundant wildlife, or simply unwind on the expansive deck while taking in the beauty and serenity of the surrounding countryside. Offering the perfect balance of seclusion and convenience, this exceptional property feels worlds away, yet is just a short drive from charming villages, acclaimed dining, cultural attractions, and everyday amenities of Dutchess County. Whether envisioned as a peaceful weekend retreat or a full-time residence, this is Hudson Valley country living at its finest.

53 Market Lane, Clinton Corners
$379,000
3 Beds ⋅ 1 Baths ⋅ 1028565 MLS
Attractive 3 bedroom, 1 bath cape cod loaded with recent improvements. Attractive open floor plan includes kitchen w/stainless appliances, granite counters & breakfast bar, which flows seamlessly to living room w/fireplace. Two first floor bedrooms and tile bathroom. Second floor includes generously sized bedroom plus office/den and storage space. Three season front porch is the perfect place to relax. Recent improvements include roof, furnace, water heater, pressure tank and 200 amp electric service. One car garage plus large workshop/studio space complete with insulation & electric and dedicated driveway. All situated on park-like property just minutes from shopping, dining, Stissing Lake and Taconic State Parkway. Attractively low taxes. An opportunity not to be missed.

2795 Church Street, Pine Plains
$2,500,000
12 Beds ⋅ 7 Baths ⋅ 1025626 MLS
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 also includes a second four-bedroom residence and a charming one-bedroom cottage, offering exceptional flexibility for extended family, guests, rental income, or staff accommodations. Privately situated, the second home features an in-ground swimming pool, providing a relaxing retreat surrounded by the beauty of the countryside. Supporting the agricultural operation is an impressive working barn thoughtfully designed to meet the needs of a modern CSA farm while preserving its traditional agricultural character. The barn includes comfortable living quarters for farm staff, stalls, extensive storage areas, and a commercial walk-in refrigeration system essential for harvesting, storing, and distributing fresh produce. These facilities provide the infrastructure necessary to continue successful vegetable production immediately upon ownership. Numerous outbuildings throughout the property support equipment storage, maintenance, workshops, and additional agricultural uses. Every element of Sisters Hill Farm has been thoughtfully developed to support both productive farming and exceptional country living. Adding to the property's exceptional value is its established Community Supported Agriculture (CSA) program. The CSA offers a well-established operation with a loyal membership base, modern infrastructure, and a strong reputation for high-quality, sustainably grown produce. The agricultural business provides an opportunity to continue a successful farming enterprise while benefiting from decades of community goodwill. Additional information about the CSA can be found at sistershillfarm.org. Whether envisioned as a private country estate, a multi-generational family compound, a working farm, or an investment in the region's agricultural future, Sisters Hill Farm offers extraordinary versatility and enduring appeal. This is more than a beautiful property—it is a place where history has been carefully preserved, the land has been thoughtfully stewarded, and the possibilities for its next chapter are truly exceptional.

123-179 Sisters Hill Road, Stanfordville
$2,475,000
7 Beds ⋅ 6 Baths ⋅ 1022023 MLS
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. On the ground floor, you’ll find a large boot room with plenty of storage, a formal dining room, a cozy living room, a wallpapered powder, and the beating heart of the home - the monumental kitchen; a light-filled and dreamy space perfect for entertaining. The second floor has two large bedroom suites with a full bath each, three additional bedrooms, and another full bath. Each bedroom has a subtle but charming color palette, more extraordinary woodwork, and two of the bedrooms have fireplaces. The proportions of the rooms and the layout are well suited to a large family or those with frequent guests, with the two en suites each occupying their own corner of the house, and the three bedrooms and last bathroom in their own wing. The Grounds: Outside, the farmhouse has two ‘faces’ and two beautiful porches. Additionally, a large dining terrace bordered by stone walls sits conveniently off the kitchen. Strolling away from the main house, you’ll find a wrought-iron greenhouse structure and a French parterre garden planted with herbs, lavender, and flowers. The Barn: The Hammertown barn, built in the early 1800s by the founding family of the property, has lived many exciting lives - from being home to elephants from the Barnum Bailey Circus in the early 1900s to its most recent iteration as the main outpost of a beloved furnishings and antiques brand. The barn’s soaring beams and incredible staircase welcome you into the structure, where multiple rooms serve various purposes - including plenty of living space (the perfect place for a home theater), open, sprawling areas with soaring ceilings ideal for hosting large groups, and an abundance of utility, office, and storage space. The barn is fully serviced with electric, air conditioning and heat, and plumbing (including a bathroom). The Guest House: The two-bedroom, two-bath guest cottage was built to elegantly blend with the property's historic character and features multiple fireplaces and detailed millwork. The double-height great room’s arched window floods the house with warm light, and French doors lead to the cottage’s sweet outdoor terrace. The Surroundings: Hammertown is just minutes from Pine Plains, less than fifteen minutes from Millerton and the Connecticut border, and two hours from New York City. The area is defined by some of the most beautiful country landscapes in the region, and is full of hiking trails, thriving local farms, and wonderful small towns and communities. As a marvelously well-serviced compound, Hammertown has incredible potential for those who also wish to explore live-work opportunities, having been home to multiple tasteful commercial ventures and events over the past several decades.

85 Hammertown Road, Pine Plains
$11,250,000
5 Beds ⋅ 6 Baths ⋅ 1020209 MLS
Privately set on 50 acres with sweeping Western views of the Catskill Mountains, this extraordinary Shekomeko estate embodies the very best of Hudson Valley country living. Designed by architect Jimmy Crisp and completed in 2004, the residence offers over 9,684 finished square feet of beautifully crafted living space. A long, tree-lined drive framed by mature red maples leads to the elegant residence, where gracious proportions and refined finishes create a home equally suited to grand entertaining and relaxed everyday living. At its heart is a chef's kitchen that flows seamlessly into the main gathering spaces, while walls of windows frame the surrounding landscape. The second floor is anchored by a luxurious primary suite with a fireplace, private balcony, sitting room, dual walk-in closets, and a spacious spa-like bath. Four additional bedrooms and a private office provide generous accommodations for guests. The lower level offers a gym, Pilates studio, play area, expansive wine cellar, and large laundry room. One of the home's defining features is the remarkable stone wing, built around a dismantled historic barn. Its vaulted beamed ceilings, custom copper railings, and floor-to-ceiling stone fireplace create a dramatic great room that opens directly to the pool. Outside, a beautifully landscaped 75' x 25' pool and spa overlook rolling fields and distant mountain views. A stone terrace with an outdoor fireplace, dining loggia, and fire pit creates exceptional spaces for entertaining, while a vegetable garden, pond, pole barn, and detached two-car garage with a studio and bath above complete the estate. Private, peaceful, and surrounded by extraordinary natural beauty, this exceptional property offers a rare opportunity to experience refined country living.

147 Moadock Road, Millerton
$799,000
3 Beds ⋅ 2 Baths ⋅ 1007119 MLS
A 1949 original, 153 Near Road was fully reimagined in 2021. The house is sited on two acres off a county lane, yet is a short distance to Hudson, Red Hook, Pine Plains with easy access to the Taconic Parkway. The first floor features an open concept, the kitchen, dining and living spaces flow together without interruption, anchored by a kitchen island and warmed by a wood stove. Flooded with natural light through picture windows the light wood floors catch and reflect the sunlight throughout the day. A first floor bedroom suite offers privacy and ease, featuring a stunning walk in shower and a laundry room tucked nearby, everything one needs on one level. Upstairs, two bedrooms feel suspended in the tree canopy. The window above the soaking tub perfectly frames it, making it an ideal spot for a moonlit soak. Enjoy the stream on a hot summer day and later relax under the stars around the firepit. The electrified outbuilding is a great space for an office or artist studio. One won't have to worry about using additional electricity, as the solar panels lighten the footprint.

153 Near Road, Red Hook
$850,000
1008519 MLS
Commercial property with Multi-Use potential in Pine Plains, NY. This versatile commercial property boasts a variety of uses, making it of interest to investors, entrepreneurs and businesses alike. With two apartments, two office spaces, dedicated studio areas and a spacious workshop area with 5 bays with overhead doors. This property offers the perfect blend of residential and commercial functionality with potential for showrooms. Hardwood floors throughout and a new roof. Hard to find commercial property.

2773 Church Street, Pine Plains
$639,000
3 Beds ⋅ 3 Baths ⋅ 1006576 MLS
Your Lakeside Sanctuary Awaits at 553 Lake Rd in Pine Plains NY. Imagine a life where your mornings begin not with an alarm, but with the gentle song of birds and the sun rising over the glassy waters of Twin Island Lake. Welcome to 553 Lake Road in Pine Plains—a home that doesn’t just offer a place to live, but a feeling of profound peace, warmth, and sanctuary. A Home Infused with Warmth and Light From the moment you step inside, you are wrapped in comfort. Gleaming hardwood floors guide you through a thoughtful layout designed to soothe the soul. The Living Room: Unwind by the crackling fireplace while gazing out at beautiful lake views. The Heart of the Home: An updated, sun-lit kitchen boasts abundant countertop and cabinet space, flowing effortlessly into a lovely dining area. The Sunroom: A bright, incredibly spacious sunroom offers the ultimate spot to curl up with a good book, practice yoga, or simply watch the seasons change. Space to Grow, Create, and Breathe The second floor features two beautifully appointed full baths, ensuring ultimate convenience with 3 bedrooms. Downstairs, a full walkout basement bursts with potential, offering the ideal layout to create an accessory dwelling unit (ADU), a guest suite, or rental space. For the creator or hobbyist, the 2-car heated garage is a dream come true, complete with a workshop and a spacious loft perfect for DIY projects or studio space. Peace of mind is also guaranteed with a whole-house generator. Embrace the Great Outdoors Step outside onto your brand-new Trex porch to sip your morning coffee, breathe in the crisp Hudson Valley air, and feel the stress of the week melt away. With over 3 private acres of your own land, you can hike, explore, and connect with nature right in your backyard. Lake access on your private dock just across the street, kayak or canoe around the lake for an interesting adventure. Looking for a challenge? The breathtaking trails of Mt. Stissing are just minutes away. The Location: A Seamless Escape Located under 2 hours from NYC with a straight, scenic drive up the Taconic State Parkway, this property is incredibly versatile. Whether you dream of a permanent full-time haven, a magical summer retreat, or a lucrative short-term rental/Airbnb, this home is ready to fulfill your dreams. Best of all, you are just 15 minutes away from the historic streets, gourmet dining, and culture of Rhinebeck and Red Hook.

553 Lake Road, Pine Plains
$549,000
2 Beds ⋅ 2 Baths ⋅ 1006574 MLS
Welcome to 559 Lake Road in Pine Plains! Boasting direct views and access to Twin Island Lake, this beautiful property has a proven track record as a highly successful Airbnb. Whether you are looking for a lucrative investment, a dream summer getaway, or a year-round sanctuary, this home has it all. The entire front of the house features stunning, unobstructed lake views. Start your mornings on the covered porch sipping coffee, listening to the birds, and watching the wildlife on the water amidst beautiful perennial flowers. Inside, enjoy a bright, spacious open floor plan ideal for modern living. The layout includes a primary bedroom and bath with plenty of closets, plus a second bedroom and a flexible home office with a large closet, sleeps like a 3 bedroom. Step outside to hike up your own 4 acres of private land, or drive just 15 minutes to enjoy the top-tier restaurants and entertainment in nearby Red Hook and Rhinebeck. All this peace and quiet is located under 2 hours from NYC via the Taconic State Parkway!

559 Lake Road, Pine Plains
$1,275,000
3 Beds ⋅ 3 Baths ⋅ 987704 MLS
A very special living and investment opportunity. Create an exceptional lifestyle in this well-preserved 1968 brick mid-century modern 3,670 sq ft one-level residence, complete with all comforts and amenities. Boasting a unique additional 2,152 sq ft attached indoor pool with floor-to-ceiling bay windows, enjoy sweeping jetliner views spanning more than 30 unencumbered miles of rolling hills to the south. Thoughtfully designed with seamless indoor-outdoor circulation and plenty of storage space, this home feels fitting for one or many. It magically transforms from a quiet writer's retreat into a vibrant family home or your private entertainment hub. Solidly built atop a hill, the easy-access bungalow-style layout features 3 bedrooms and 2 bathrooms on one side, and generous communal spaces on the other--including a living room, an open kitchen with dining area, and a large sunny room ideal for use as an office or additional living space. The island kitchen showcases custom-built original Quaker Maid maple cabinets paired with a state-of-the-art pantry. The original mid-century modern carefully preserved design contributes to the home's authentic historical charm while modern conveniences such as central air conditioning, high-speed internet, and a multi-point alarm system provide comfort. The large 1,800 sq ft heated basement includes a second kitchen area with double sink, countertops and cabinets, a full bathroom, laundry, utility room, and ample storage, ready to become a recreational space when adding a ping-pong table, a pool table and a movie screening area. An attached garage with additional workshop gives direct interior access to the house through a mudroom featuring bluestone floors and cedar walls. Swim year-round in the heated indoor kidney-shaped pool equipped with saltwater system & dedicated propane furnace; the solid brick construction includes a newer roof, massive industrial beams & renovated hardwood ceiling. Vinyl liner was recently replaced. Huge yoga deck facing the view. Property has two wells: one for the main house and a second dedicated to the pool and the garden's automatic irrigation system. The fenced vegetable garden sits just steps from the kitchen. Other practical touches include an automatic generator, outdoor spigots, & exterior outlets. The blacktop driveway makes snow removal quick and easy, while the parking area easily accommodates eight vehicles for pool parties or BBQs. Thanks to the elevated location, cell phone reception is strong. In-ground power lines enhance the elegance of the park-like setting, with its maintained lawn and mature trees offering plenty of outdoor space to roam after your daily swim. The house and grounds are easy to maintain. Use the large detached powered shed for lawn equipment storage, or convert it into a studio. Adding to the property's versatility, the 4.23 acres are already subdivided into two parcels with separate tax bills: the upper 2.23-acre parcel includes the residence while the lower 2-acre parcel is currently zoned as residential vacant land. This property has a renewable two-year Short-Term Rental (STR) permit and is currently operated successfully as an STR for half the year. The property also offers tremendous solar potential. Conveniently located less than a mile from the Taconic State Parkway (yet you cannot hear it), and only a 1hr 45mn drive from New York City, this peaceful and secluded residence makes the perfect weekend or vacation home. Pick up your guests or park at the Rhinecliff or Poughkeepsie train stations - respectively 30mn & 25mn away - or enjoy a scenic 1 hr 50 mn train ride along the Hudson River to the city. Own your own hill with million-dollar views, enjoy it as a primary luxury residence, a seasonal work-from-home getaway, or generate income with this turn-key piece of paradise. Included adjacent parcel address is 68 Ridge Rd Parcel ID 1352006569128825380000.

68-78 Ridge Road, Clinton Corners
$409,000
3 Beds ⋅ 2 Baths ⋅ 999870 MLS
Tucked away on a quiet country road and surrounded by open fields and natural beauty, this charming ranch-style home offers the perfect blend of comfort, flexibility, and peaceful country living. Set on a manageable .25-acre lot this 3-bedroom, 2-bath home features approximately 1,860 square feet of living space with hardwood floors throughout the main level. The fully finished lower level greatly expands the home’s versatility and includes a spacious living room, dining area, full bathroom, and a “summer kitchen,” making it ideal for extended family, guests, or potential mother/daughter living arrangements. Step outside and enjoy the wonderful covered patio area, perfect for relaxing, entertaining, or summer grilling while taking in the peaceful surroundings. Whether you’re searching for a full-time residence, country retreat, or weekend getaway, this inviting Pine Plains home offers warmth, flexibility, and a tranquil setting just minutes from town amenities and outdoor recreation.

211 Sigler Road, Pine Plains
$489,000
4 Beds ⋅ 2 Baths ⋅ 999436 MLS
Step into the charm and character of a bygone era with this spacious early-1900s Colonial-style home located in the heart of the hamlet of Pine Plains. Offering over 3,000 square feet of living space, this 4-bedroom, 1.5-bath residence sits on approximately 0.47 acres and is filled with history, warmth, and timeless architectural details. Once home to both the town pharmacy and library, this unique property blends rich local history with classic Hudson Valley charm. Inside, you’ll find stunning original woodwork and trim, oversized rooms, high ceilings, and beautiful hardwood floors throughout — long protected beneath carpeting for many years and now ready to shine once again. The two-story home offers endless potential for restoration, modernization, or simply enjoying its authentic character as-is. A large barn located behind the home provides excellent storage, workshop space, studio potential, or future creative use. Perfectly situated in the center of town, the property is walkable to local restaurants, the post office, pharmacy, and other village conveniences. Outdoor enthusiasts will appreciate the nearby hiking and biking trails, while commuters and weekend travelers will love being just approximately 30 minutes from both the Amtrak station and the Metro-North Railroad station in Poughkeepsie. Conveniently located between Rhinebeck, Hudson, Millbrook, and Millerton, this home places you in the center of some of the Hudson Valley’s most desirable destinations. A rare opportunity to own a piece of Pine Plains history with space, character, and incredible potential.

7786 S Main Street, Pine Plains
$9,500,000
5 Beds ⋅ 7 Baths ⋅ 996948 MLS
A rare offering of enduring beauty and thoughtful design, this extraordinary modern farmhouse—built in 2019—stands as a true masterpiece set on 52.32 acres of rolling landscape, with sweeping views of mountains, open hills, and the Roeliff Jansen Kill. Spanning 6,875 square feet, the residence blends refined craftsmanship with a warm, livable elegance. Reclaimed 19th-century pine floors with rose head nails run throughout, grounding the home in history while soaring ceilings—including 10’7” in the kitchen and a dramatic 24’6” vaulted, beamed living room—create a sense of scale and light. Walls of windows frame the house and look out onto the established English gardens and beyond to the surrounding hills and orchards. The heart of the home is a remarkable kitchen, complete with its own fireplace, a Lacanche range, and a full wall of glass overlooking the landscape. A separate pantry is equally well-appointed with marble countertops, SubZero refrigerator, and a Miele dishwasher. Every space reflects an uncompromising attention to detail. The main living room is both grand and inviting, featuring exposed beams, a fireplace, built-in library, and French doors that open seamlessly to the outdoors. The primary suite offers a private retreat with a 17’6” vaulted, beamed ceiling, its own fireplace, and a wall of glass capturing the Berkshire Mountains. The spa-like bath includes marble double vanities, a clawfoot tub, and an open shower, complemented by custom-designed closets. A thoughtfully designed greenhouse breezeway connects the main house to a beautifully appointed guest wing. This unique space features soapstone sinks, plaster walls, and French doors leading to a charming courtyard with a fountain made from a 300 year old limestone trough. The guest wing includes a vaulted great room with kitchenette, bedroom, and bath, along with a separate studio or office with woodstove and an additional powder room—ideal for guests, extended stays, or creative pursuits. Additional features include an expansive laundry room with double washers, a dedicated yoga or fitness room, and a mudroom designed for both function and style. Outdoors, the property is equally compelling. There is a heated, saline 18’ x 50’ gunite pool and pergola for dining al fresco. The formal gardens are planted with heirloom roses, towering delphiniums and other classic cottage flowers that bloom the whole season long, and include a white garden that glows in the moonlight. This is a truly bucolic property with dry stonewalls, antique blue stone terraces and a walled vegetable garden just waiting to be planted in the spring. The land itself is rich and vibrant, with an organic orchard featuring multiple varieties of pear, apple, plum and peach, along with blackberry, blueberry, and raspberry bushes. A classic 24’ x 38’ barn with wood sided walls and a separate workspace offers further versatility and space for storing wood and tools. Bordering the property, the Roeliff Jansen Kill provides a peaceful natural edge with trout fishing, complemented by a tributary stream that meets the Roe Jan and picturesque waterfalls. Designed with sustainability in mind, the property incorporates solar energy and electric car charging while seamlessly blending efficiency with luxury living. An exceptional Hudson Valley estate where timeless materials, modern efficiency, and breathtaking natural surroundings come together in perfect harmony.

506 Silvernails Road, Pine Plains
$1,425,000
3 Beds ⋅ 3 Baths ⋅ 996917 MLS
**TO BE BUILT** – This custom 3-bedroom, 2.5-bath Farmhouse Ranch seamlessly blends timeless charm with modern design, offering nearly 2,600 SQFT of thoughtfully designed living space. Privately set on 6 acres following a long meandering driveway and tucked far back off the road, this property offers the perfect balance of privacy and convenience in the heart of Clinton Corners. Upon arrival, you’re welcomed by a charming wrap-around rocking chair front porch, while a deep rear porch extends the living space outdoors—perfect for relaxing or entertaining. Inside, the open-concept layout effortlessly connects the vaulted living room, kitchen, and dining area, creating a spacious and airy atmosphere centered around a cozy gas fireplace. A formal dining room and dedicated home office provide added flexibility for entertaining or working from home. The thoughtfully designed split-bedroom floor plan ensures privacy, with the primary suite tucked away in its own quiet corner of the home. This inviting retreat features a vaulted ceiling, an en suite bath, and an oversized walk-in closet. Two additional bedrooms are situated on the opposite side of the home and share a full bath. Above the garage, a spacious bonus room offers endless possibilities for a media room, playroom, guest quarters, or additional flex space. High-efficiency Bosch electric forced-air heating and cooling make maintaining comfort effortless year-round. Generous builder specifications include oak flooring throughout the common areas and granite/quartz countertops throughout. This is a rare opportunity to build a custom home in a peaceful, scenic setting—crafted for modern living while capturing the timeless appeal of a classic farmhouse. Reach out today! **PHOTOS ARE RENDERINGS OF A SIMILAR MODEL BUILT WITH OPTIONS. BUILDER CAN BUILD TO SUIT AS WELL.

114 Quarfelt Road, Clinton Corners
$1,649,000
5 Beds ⋅ 4 Baths ⋅ 991832 MLS
A meticulously restored and turnkey farmhouse, thoughtfully reimagined for modern living while honoring its architectural character, spans the picturesque landscape of Dutchess and Columbia Counties. A stunning bluestone courtyard, framed by handcrafted stone walls sourced from the property itself, creates an unforgettable outdoor setting—equally suited for elegant entertaining, intimate al fresco dining, or quiet evenings beneath the stars. The result is a home that feels timeless, sophisticated, and effortlessly relevant for today's lifestyle. Inside, you will find five bedrooms and four full baths that unfold across a series of beautifully scaled interiors. Expansive Primary first floor ensuite with radiant floors, gas fireplace, balcony with walkout to upper deck. Wide plank floors, exposed hand hewn beams, and original millwork throughout the home speak to a level of craftsmanship seldom found today. The living spaces are both flexible, refined and inviting. Designed for a seamless balance of everyday comfort and sophisticated entertaining. The open kitchen was remodeled with new butcher block countertops, top of the line appliances, new center island and coffee bar with wine fridge. Take a step down to the sunroom with exceptional light, where French doors blur the line between indoors and courtyard living. A beautifully scaled flex room above the garage, offering endless versatility. Numerous improvements include new roof, windows, water filtration system, new front double entry doors and much more. Ideally sited for seamless access to the Taconic Parkway, the villages of Rhinebeck and Red Hook, and the Rhinecliff train station. This home is where history, architecture and landscape converge in a singular and irreplaceable offering.

1429 Jackson Corners Road, Red Hook
$459,000
3 Beds ⋅ 2 Baths ⋅ 993951 MLS
Beautifully renovated from top to bottom. This lovely one level ranch is immaculate and the gem you have been looking for. Walk in to your light filled Living Room open to your dining area, this is truly the heart of your home as the Kitchen, Primary Suite and Guest Bedrooms wing all branch off here. To the left we have a large Primary Bedroom with Walk In Closets and a delightful Primary Bath, bright and clean. The Kitchen is conveniently off the Dining Area and offers wonderful stainless steel appliances, loads of cabinet space and a lovely Eat in Area with walls of windows flooding the home with sunlight. Laundry couldn't be easier with connections in place in a tucked off Pantry. Sliders to the handsome back Deck for al fresco entertaining in the Hudson Valley sunshine. Backyard overlooks your wooded oasis to take in the mature Pines and listen to the Birds. Down the hall there are Two Guest Bedrooms and a hall Bathroom with tub. Great Lower level that walks out to a cute side Deck, wood stove here for cost effective heat and cozy nights. Two Car Garage off this level for ease in all weather, all year long. Ample storage in Garage as well. Light, Bright, and new this ones a real rarity. The sweet town of Elizaville is minutes from neighboring Red Hook and Germantown, still undiscovered you'll love spending the summer swimming at Twin Lakes, and dining at Kiki's Diner, and finishing with ice cream and the Farmers Market at Roosters. 90 minutes to NYC, 6 min to the TSP for easy access.

83 Weaver Road, Elizaville
$575,000
7 Beds ⋅ 5 Baths ⋅ 993929 MLS
Stunning renovated Colonial farmhouse set in a peaceful country setting with beautiful pastoral views, just minutes to the Village of Pine Plains. Completely updated in 2020, this spacious home offers the perfect blend of classic charm and modern finishes. The main residence features 4 large bedrooms and 3 full bathrooms, a gracious formal dining room, and a bright, open kitchen with tile flooring and an electric fireplace for a warm, inviting feel. The oversized living room is filled with natural light and highlighted by a beautiful bay window. A finished attic provides additional flexible space, ideal for a home office, studio, or a fun hang out space for teenagers. A standout feature is the separate in-law suite or legal rental, offering 3 bedrooms and 2 full bathrooms with upscale finishes and tile work throughout—perfect for extended family, guests, or income potential. Enjoy quiet country living with easy access to everything the area has to offer—just minutes to Pine Plains and a short drive to Millerton. Spend your weekends exploring local farm stands and farm-to-table dining, walking trails, and scenic hiking. Stissing Lake is nearby for kayaking, swimming, and relaxing summer days. Conveniently located just 10 minutes to Millerton and within 20 minutes to both Red Hook and Rhinebeck. A rare opportunity to own a versatile and beautifully updated property in one of the Hudson Valley’s most charming countryside settings.

80 County Route 7, Pine Plains
$1,250,000
4 Beds ⋅ 5 Baths ⋅ 990579 MLS
Originally built in 1836, this beautifully restored Greek Revival Center Hall welcomes you with timeless charm and thoughtful updates. Set on over four acres with Willow Brook gently winding through the property, it offers a warm, peaceful retreat where historic character and modern comfort come together to create a truly special place to call home. Town historical records state it was used in the Underground Railroad, as well as a quarterly meeting place for the Quakers, who were Abolitionists during the American Civil War - all while being a vibrant and successful dairy farm in the heart of the Hudson Valley. Inside, original wide board floors, exposed hardwood beams, and intricate molding and trim work highlight the home's craftsmanship. The center hall layout leads to a stunning double parlor with two fireplaces and original pocket doors, as well as an open dining and living room boasting two additional fireplaces, perfect for gatherings both intimate and large.The heart of the home—a warm and inviting kitchen—features a wood-burning fireplace, gas stove, island, walk-in pantry, and laundry room. From here, step out to a screened porch —ideal for morning coffee, evening relaxation, or weekend entertaining. Upstairs you'll find 3 spacious bedrooms and 3 full bathrooms, as well as a room that could be used as a 4th bedroom, a custom walk-in closet/dressing room, or sitting room. The attic is a versatile space and can be reached by 2 separate staircases. The exterior boasts classic clapboard siding, metal roof, original 6-over-6 windows, raised garden beds, a fenced backyard, and several vintage outbuildings. In the basement you'll find updated mechanicals and the original milkroom with bluestone floor, echoing the home's agricultural past. Located just 3 miles from the Taconic State Parkway, this exceptional property is a beautiful blend of historic significance, and modern functionality.

36 Market Lane, Clinton Corners
$394,000
3 Beds ⋅ 2 Baths ⋅ 988822 MLS
Sweet and solid, one level Ranch home on a bucolic setting with rolling hills and farmland framing your homestead. Walk into your open living room with built ins and lovely bay window. Through to the dining room and eat in kitchen, perfect for hosting with ease. Sliders to the back covered porch off the dining room allows for al fresco living and enjoying your coffee while watching the sunrise. Laundry room off the kitchen for convenience. Back off the living room is your primary suite, room for all your furniture and has a massive ensuite bathroom with soaking tub and shower, skylights bathe the room in sunlight. Off the dining room is a large living room with room for all. Two guest bedrooms stretch off the living room. Full guest Bathroom with tub on this wing of the home. High efficiency Split Units keep the home cool and supplement heat. Outside there is a world of possibilities for the craftsman, car enthusiast, or artist or artisan for Studio space, with an oversized two car garage with lofted storage, heat and electric in here. Then enter the massive 1287 square foot Garage with space for all your needs, storage or uses. In there there is electric, heat, and water. Additional Shed outside for storage,. Yard is perfect for all your needs, and is already outfitted with an invisible fence for your Furry family members. In the heart of Pulvers Corner, 5 minutes to Pine Plains Village, 10 minutes to Stanfordville and Millerton this is a fabulous location.

3838 Route 199, Pine Plains
$2,895,000
4 Beds ⋅ 5 Baths ⋅ 982890 MLS
A study in proportion, light, and restraint, this under-construction residence, designed by Incorporated Architecture and Design and developed by ROAM Properties, is set back across seven acres within a private community in Red Hook, New York, where meadow and woodland converge at the edge of the Hudson Valley. Two wood-clad volumes anchor the composition, their silhouettes inspired by vernacular forms yet rendered with precision and clarity. The architecture is quiet but deliberate, designed to recede into the landscape while opening fully to it. At the center of the home, a dramatic 30-foot vaulted living and dining room rises in a single uninterrupted gesture. Natural light moves across pale plaster walls and wide-plank European oak floors, shifting the atmosphere throughout the day. A wood-burning stove grounds the space, bringing warmth and intimacy to the soaring volume. The kitchen is integrated rather than announced, wrapped in custom oak cabinetry and stone, with Thermador appliances discreetly concealed within. Just beyond, a wet bar allows the home to move effortlessly from daily living to evening entertaining. The residence offers four bedrooms and four-and-a-half baths, arranged with a strong sense of rhythm, privacy, and ease. A first-floor primary suite is complemented by a separate guest suite with its own kitchenette, creating comfort and autonomy for visitors. A den, reading nook, and office introduce quieter moments throughout the home and provide ample flexibility for working remotely. Bathrooms are finished in porcelain and stone surfaces with radiant heat underfoot. The primary suite is intentionally pared back, featuring a walk-in rain shower and a freestanding tub positioned to capture filtered light from the surrounding forest. Outside, terraces extend from the main living spaces into the meadow, where a 20-by-40 heated saltwater pool sits just beyond. The transition between architecture and landscape feels seamless, less a boundary than a gradient. Built with a high-performance envelope and thoughtfully selected materials throughout, the home balances architectural clarity with long-term livability. Quietly confident and deeply considered, 60 Stone Wall Path offers a rare opportunity just minutes from the villages of Red Hook and Rhinebeck, approximately 90 minutes from New York City, and moments from the Taconic State Parkway, an ideally situated home base from which to explore the very best of the Hudson Valley. Expected completion: December 2026.

60 Stone Wall Path, Red Hook
$575,000
7 Beds ⋅ 5 Baths ⋅ 969056 MLS
This beautifully updated legal 2-family home seamlessly blends vintage charm with modern convenience, offering exceptional flexibility for multigenerational living, rental income, or guest accommodations. Located just 7 minutes from Pine Plains Village and set on a scenic lot with sweeping countryside views and a neighboring 200-acre farm, the property features meticulously maintained grounds, two storage sheds for garden tools and recreational items, and ample off-street parking. The main house offers 4 spacious bedrooms and 3 full baths, a large sunlit living room, a formal dining room, original hardwood floors, a grand staircase with the original banister, and a finished attic—perfect for a playroom, studio, or home office. The renovated kitchen features granite countertops, stainless steel appliances, an oversized island, tile flooring, and an electric fireplace, with a separate laundry room and an additional full bath located on the main level. The private second unit (or guest wing) is a legal 3 BR/2 Bth apartment and includes a first-floor primary bedroom with a walk-in shower, an open-concept living and dining area with beautiful views, two more bedrooms and a full bath upstairs, plus convenient second-floor laundry. Both units share a heated enclosed porch/mudroom for entry, while the main house also enjoys a formal front entrance with vintage appeal. Currently tenant-occupied on month to month contracts. Please contact the broker for rent roll, expenses, and additional details. A new 2000 gallon septic system was installed in 2021. Heating is provided by oil with central air in Unit 1, and mini-split systems were added to Unit 2 in 2023 for efficient year-round climate control. This is a truly unique Hudson Valley opportunity, perfectly positioned on the Ancram border and just two hours to Manhattan by car, or 20 minutes to Hudson for Amtrak access. There's so much to love! Come see for yourself! Photos have been virtually staged.

80 County Route 7, Pine Plains
$4,495,000
7 Beds ⋅ 4 Baths ⋅ 947632 MLS
Cedar Ridge Farm is a premier 246-acre equestrian estate set in the heart of Dutchess County, offering exceptional land quality, extensive infrastructure, and the rare scale required for a top tier equestrian operation or private country estate. The farm encompasses approximately 110 acres of fenced paddocks supported by thoughtfully designed facilities that ensure efficiency, functionality, and year-round usability. The property features a total of 33 stalls across three well-equipped barns. The Morton barn includes 12 stalls along with a wash stall, tack room, bath, and a large one-bedroom apartment. The main barn provides 15 stalls, including box stalls, and is complemented by a feed room, office, workshop, and medical room. The tractor barn offers six additional stalls, and automatic waterers are positioned throughout the fields to support daily operations. Residential accommodations include a main house and two three-bedroom cottages, offering flexible living arrangements for owners, staff, or guests. The property is supported by four wells, multiple septic systems, oil fired forced hot air heating, and generator hookups with gas generators, ensuring reliable service throughout the farm. One of the most distinguishing features of Cedar Ridge Farm is its exceptionally flat topography—an uncommon asset in this region that makes the land ideal for a variety of equestrian uses, including the potential development of regulation size polo fields. While the property is not eligible for subdivision, it does include a designated homesite for future construction. Cedar Ridge Farm presents a rare opportunity to own a fully equipped, largescale equestrian property in one of the Hudson Valley’s most established and desirable horse communities. It combines functionality, beauty, and long-term potential, making it an outstanding offering at the highest level of the market.

8032-8060 Rt-82, Pine Plains
$3,995,000
10 Beds ⋅ 7 Baths ⋅ 953909 MLS
Set far back from one of the Hudson Valley’s most prestigious and scenic roads, this stunningly restored 1830s colonial farmhouse is a masterclass in combining historic charm with sophisticated living. Situated in the heart of the pastoral Shekomeko Valley on just under 10 pristine acres, this property offers ultimate privacy surrounded by large, rolling farms and protected acreage. Classic white clapboard siding and a welcoming front porch set the stage for a home that seamlessly blends 19th-century soul with modern amenities. Step onto original wide-plank flooring and admire the stunning, exposed hand-hewn beams. An oversized living room features a wood-burning fireplace and panoramic views from three exposures, with French doors leading to the expansive property. The formal dining room boasts an additional fireplace and two large china closets. The professionally equipped kitchen includes dual sinks, a premium professional range, a built-in refrigerator, and a sunny, south-facing breakfast room with pastoral views. A convenient butler’s pantry and powder room are also included on this level. Head upstairs to four bedrooms (two with fireplaces) and three bathrooms. The main house includes a fully equipped 3-bedroom apartment with a separate entrance—perfect for guests or staff. The property is a true compound, designed for both entertainment and flexibility. A fully outfitted barn includes a 3-bedroom apartment, a gym with a sauna, laundry, a workshop and a very large storage room which can easily be converting into more living space. Other buildings include another barn/workshop, a yoga studio, a 2-car detached garage with a storage loft, and a 60' equipment shed. This parcel offers endless potential for hobby farming, horses/livestock, or creating a private, quiet home office. Located in the desirable Shekomeko Valley, this property offers a rare mix of secluded tranquility and easy access to nearby towns.

1515-1517 Route 83, Pine Plains
$164,900
4 Beds ⋅ 3 Baths ⋅ 951903 MLS
Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

245 Hicks Hill Road, Pine Plains
$164,900
932119 MLS
Attention investors & contractors! 4 Bedroom, 2.5 Bathroom Two Family Ranch on 2.4 acres in T/Pine Plains! Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

245 Hicks Hill Road, Pine Plains
$485,000
4 Beds ⋅ 3 Baths ⋅ 924504 MLS
A Home with a view of Stissing Mountain! Enjoy gorgeous sunsets all year long from your front door. Spacious raised ranch on a level lot is move-in ready. Main floor has an open floorplan and wood floors throughout. The light filled kitchen with a nice sized island has new granite countertops. The storage room next to the kitchen could easily become a walk-in pantry. Primary bedroom has en-suite bath. A second hallway full bath is conveniently located for use by the other two bedrooms. First floor also has guest quarters that include a bedroom, half bath and sitting room or office. Finished basement with a gas fireplace for those chilly winter nights at home with family. An additional room that could be for gaming, office or den. Completing the lower level is a separate room for laundry. There is also a one car garage and an unfinished bonus room waiting for you to make it special to you. Plenty of yard space for outdoor activities and BBQs. Driveway has room for plenty of off-street parking. Quiet road conveniently located near the town park – beach, kayaking, playground, large pavilion, picnic area, etc. A short distance to Thompson Pond Nature Preserve, plenty of hiking trails including a trail up to the Stissing Fire Tower. Less than a mile from village center with its quaint shops and eateries – dine at The Stissing House or get pizza or burgers and don’t forget to visit the Stissing Cultural Center for a concert or a play. Come take a look!

82 Lake Road, Pine Plains
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