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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
$1,200,000
3 Beds ⋅ 3 Baths ⋅ 1020922 MLS
Perched high on 5.32 private acres with breathtaking, distant panoramic views of the Taconic Range and Berkshire Mountains, this contemporary home has been completely transformed by a top-to-bottom renovation. Seamlessly blending chic modern upgrades with dramatic architectural bones, this turn-key residence offers utmost privacy on a scenic country lane, yet still provides incredible convenience; located just minutes from the Taconic State Parkway, less than 10 minutes to Pine Plains, and a 20-minute drive in either direction to Rhinebeck and Millerton. Spanning nearly 3,000 square feet, the residence unfolds across a light-filled, open-concept floor plan designed to celebrate its extraordinary setting. The dramatic great room serves as the heart of the home, anchored by soaring vaulted ceilings, a floor-to-ceiling exposed brick feature wall, and a wood-burning stove. Expansive walls of glass frame the surrounding landscape and open seamlessly to a generous entertaining deck, creating a natural extension of the living space and capturing breathtaking mountain views in every season. The beautifully appointed kitchen combines timeless design with modern functionality, featuring custom shaker cabinetry, a substantial center island, quartz countertops, and stainless-steel appliances. Adjacent living and dining spaces flow effortlessly, creating an ideal environment for both intimate gatherings and larger-scale entertaining. The main level is anchored by a private primary suite with a walk-in closet and direct access to the deck, offering a serene connection to the surrounding landscape. A dedicated office, laundry and pantry room, and powder room complete the floor. Upstairs, two additional bedrooms, a flex space, and two renovated baths are arranged around a dramatic overlook to the great room below, while a secret bonus space offers endless possibilities as a fitness studio, media room, playroom, or additional office. Beyond the cosmetic artistry, the property features a comprehensive utility overhaul engineered for modern reliability and comfort. The home's infrastructure is anchored by a high-efficiency dual-zone Carrier climate control system with central air and heat pumps, an energy-saving ventilation system, and a robust 200-amp electrical setup backed by a 20KW Kohler standby generator. Pristine water quality is guaranteed by a multi-stage filtration system including UV purification and advanced reverse osmosis lines, while a smart home network of eero mesh Wi-Fi, hardwired Cat 6 connections, Ring cameras, and Nest smart detectors delivers ultimate peace of mind. A rare offering that combines contemporary design, turnkey condition, and spectacular Hudson Valley views, 572 Hicks Hill Road presents an opportunity to enjoy elevated country living in one of the region's most desirable locations.

572 Hicks Hill Road, Stanfordville
$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
$1,850,000
3 Beds ⋅ 4 Baths ⋅ 1022485 MLS
A c1865 Italianate farmhouse set back from the road under mature willows and maples, with the arched dormer, bracketed eaves, and double-leaf paneled front door that mark the period. The house has been kept close to original — wide pine plank floors throughout, tall windows, a carved wood mantel with a green marble surround in the living room — while the systems underneath it have been fully updated. Main level- Double front doors open to a side stair entry hall with original pine flooring and mud room space for your jackets and shoes. The living room holds a bay window, a period mantel, and leads through to a green-walled study with a sitting area and desk. The kitchen and dining room are the result of a recent addition. The kitchen features black cabinetry, brass hardware, butcher block counters, and a zellige tile backsplash and range hood; a wall of windows over the sink looks out to the willows. A blue-walled family room and adjoining dining area spills out to the back patio for easy gathering and entertaining. A full bath with laundry and main floor bedroom complete the level. Upper levels- The second floor has 2 bedrooms, one beautifully appointed at the front of the house, with a full hall bath. The primary suite is anchored by a wall of built-in bookshelves, has a walk in closet and en suite bath. A finished third-floor room under the eaves, lit by a skylight, works as a sleeping loft or playroom and includes a full bath. Grounds A deep, tree-lined lot with mature plantings, a boxwood-edged path to an in-ground salt water pool with a stone patio, bordered by perennial beds. There is a small accessory dwelling for an office, art studio or yoga room. Location On County Route 19 in the Town of Clermont, Columbia County — between Red Hook and Hudson, with easy access to the Taconic State Parkway and the Amtrak stations in Rhinecliff and Hudson.

1788 County Route 19, Red Hook
$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
$429,000
3 Beds ⋅ 1 Baths ⋅ 1026705 MLS
Beautiful, quiet neighborhood with park like setting. Lovely three-bedroom home with landscaped front, back and side yards. Spacious living room flows into quaint dining room with stained pine tongue & groove walls & updated country kitchen with backyard walkout access. Whether you're relaxing in front of the fireplace in the living room or entertaining friends at the backyard fire pit, you will love your new life in beautiful Pine Plains township! Updated kitchen with Farmhouse Sink & Butcher Block counters and shelving. Complete top of the line package of Samsung Wi Fi appliances including Samsung Refrigerator, Stove, Microwave & Washer/Dryer. Hardwood floors throughout. Newer roof and boiler. Brand new finished outdoor shed stays! Short walk to Stissing Pond Rec Beach, ball fields and boat launch. A nature enthusiast's dream with nearby hiking trails throughout beautiful Stissing Mountain as well as Thompson Pond & Twin Island Lake, all just a few minutes’ walk through quiet back roads. Five-minute walk to shops, restaurants, high school, post office, salons, popular Back Bar Beer Garden and world famous Stissing House! Five-minute drive to Taconic Parkway. Central to Rhinebeck, Red Hook, Millerton, Kingston and Great Barrington. Call today!

75 Birch Drive, Pine Plains
$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
$400,000
3 Beds ⋅ 4 Baths ⋅ 1016273 MLS
A unique opportunity for builders, investors, contractors, or buyers with vision, this distinctive property offers exceptional potential. The existing 3-bedroom home had been extensively renovated and was ready for occupancy before a minor fire resulted in the interior being taken down to the framing. Importantly, the exterior of the home was not affected, providing a valuable head start for restoration and rebuilding. This rare property allows the next owner to complete the renovation and bring the home back to life while benefiting from many of the substantial improvements already made. Adding to its versatility, the property includes a second approved building site for a 1-bedroom cottage, creating flexible options for guest accommodations, a home office, rental income, or a private retreat. Beyond the improvements, the land’s natural beauty further enhances its appeal. Established fruit trees, scenic woodland trails, and striking rock outcroppings create a picturesque setting rich in character and outdoor enjoyment. Whether exploring the woods, harvesting fruit, or simply taking in the peaceful surroundings, the property offers a meaningful connection to nature. An oversized garage provides ample space for vehicles, equipment, storage, hobbies, or workshop use. Whether you’re looking to restore the existing residence, create a multi-building compound, or invest in a property with significant upside, this special parcel provides the ideal foundation to bring your plans to life. Conveniently located with easy access to the Taconic State Parkway and just minutes from the dining, shopping, arts, and cultural attractions of Red Hook, Rhinebeck, and Hudson, it offers an appealing balance of privacy and accessibility. Properties with this combination of restoration potential, additional building capacity, natural beauty, and versatile outbuildings are increasingly rare. Bring your ideas and realize the full promise of this one-of-a-kind property. Buyers to perform their own due diligence regarding approvals, permits, building requirements, and intended uses.

117 Camp Road, Red Hook
$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
$565,000
2 Beds ⋅ 2 Baths ⋅ 1017861 MLS
2-4 Lot Subdivision, includes secluded 2BR/2BA RANCH w/2 large decks, all wood floors and wood siding + detached 2 car garage on 7+acres in Hamlet zone (possible subdivision into 2 lots) Plus adjoining 8 acre parcel. Adjoining 4 acre boha parcel can be added for $125,000. Great location between Pine Plains Village and Millerton on quiet road off Route 199. New well installed. Easy to show with notice.

618 Bean River Road, Millerton
$799,000
3 Beds ⋅ 3 Baths ⋅ 1011393 MLS
Beautifully reimagined 1924 home blends character with modern comfort and thoughtful design. Completely renovated in 2020 the residence offers 2,304 finished square feet with 3 bedrooms and 3 full baths. Vaulted ceilings, exposed beams abundant windows and an open-concept floor plan create a sense of beauty and spaciousness. The main level features warm wood floors, radiant heat throughout, and seamless flow between the living, dining, and kitchen areas. A dedicated office space provides flexibility for remote work or creative pursuits. The first floor primary suite serves as a private sanctuary, complete with its own deck overlooking the peaceful backyard. A second deck extends the dining and kitchen areas creating the perfect setting for outdoor dining, entertaining, or simply enjoying the tranquil surroundings. The finished walkout lower level expands the home's versatility with polished concrete floors, radiant heat, a full bath, a bedroom, a family room, and a kitchenette area. With two separate entrances on the lower level this area is ideal for entertaining, guests, extended family, or multi-generational living. Outside, a stream winds through the property, with a bridge providing access to both sides of the land. Durable hardwood siding, a 50-year shingle roof, and a new propane boiler installed in 2026 offer peace of mind and long-term value. Easy access to the Taconic State Parkway and conveniently located near the villages of Red Hook, Rhinebeck, Pine Plains, and Hudson, placing some of the Hudson Valley's most desirable destinations within easy reach.

82 Near Road, Red Hook
$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
$1,695,000
3 Beds ⋅ 3 Baths ⋅ 1010636 MLS
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 Millerton, and 20 minutes to Millbrook.

1504 Route 83, Pine Plains
$750,000
4 Beds ⋅ 3 Baths ⋅ 1005453 MLS
Light-filled 2006 home blends privacy with effortless convenience. An open-air front porch and a generous backyard frame inviting indoor/outdoor living. Inside, the living room centers on a charming stove, while the chef’s kitchen echoes the home’s airy feel with an island and open plan ideal for entertaining. The first-floor primary suite is a private retreat with a freestanding tub and tiled shower. A powder room and a large mudroom with built-in bench connect to the garage. Upstairs, three additional bedrooms share a full bath with double vanities and a washer/dryer hook-up. The lower level adds flexible space with a recreational room and an office/den. Country living, refined and easy. Set just minutes from the village of Pine Plains & 15-20 minute drive to Rhinebeck and Millerton

82 Maple Hill Lane, 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
$875,000
3 Beds ⋅ 2 Baths ⋅ 1002917 MLS
Early house with charming changes. All updated. Overlooking stream and pond. On 13+ acres. Meadows and woodland walks. Charming old apple orchard. 3 bedrooms, primary bedroom on ground floor. 2 baths. Fireplace in living room. Swimming pool.

74 Willow Brook Road, Clinton Corners
$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
$585,000
3 Beds ⋅ 3 Baths ⋅ 998510 MLS
Perched up high with lovely distant views of the mighty Catskill Mountains, this Classic Country Cape Cod offers room for everyone. As you pull up your meandering, private drive you'll be welcomed by the classic rocking chair porch inviting you for conversations and lemonade. Enter the foyer to find a formal sitting room ready for you to cozy up by the fireplace with your favorite novel. The Eat in Kitchen and Formal Dining boasts plenty of space for entertaining with Breakfast Bar and sliders to the deck for dining with nature. A Den/ Office space with oversized windows and Pellet Stove makes working from home so nice. A Huge Primary Bedroom with En-suite and California style closet completes the first floor. On the second floor, you'll find a sweet, little sitting area, a perfect place for your private library. An extra-large Guest Room with Dormer and Catskill Mountain view. Another large bedrooms & Office Space. All 3 rooms share a nice sized Full Bath. The Bonus Room would be a great artists studio, yoga room, or media room. The Full, Unfinished Walk Out Basement with utilities and plenty of storage has ample space for rec room or even in law suite. Potential in place for Two Car Garage. A huge deck perfect for a big party has a charming Pergola and access to an ABG pool for summer fun. Set on over almost 3 Park-Like acres of Park Like land this rare find offers so much for the money. Quick stroll to Elizaville Deli and Diner and even Roadside Rooster for ice cream. 10 minutes takes you to Red Hook, Rhinebeck and TSP and all the wonderful things that make the Hudson Valley great!

1763 County Route 19, Red Hook
$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
$1,425,000
4 Beds ⋅ 3 Baths ⋅ 996322 MLS
Step into timeless elegance with this beautifully updated 1790's colonial estate, consisting of two parcels totaling 9.4 picturesque acres. Offering 3,337 square feet of thoughtfully restored living space, this extraordinary home seamlessly blends historic character with luxury modern upgrades. This home features four bedrooms and three full bathrooms, and is highlighted by original wide-board flooring, 9' high ceilings, and exquisite period moldings throughout, preserving the home's rich heritage. The heart of the home is a one-of-a-kind custom kitchen featuring top-of-the-line appliances, an 18' vaulted ceiling with stunning exposed beams, and a massive island topped with Danby marble. Adjacent to the kitchen is a pantry/laundry room with custom floor-to-ceiling cabinetry designed for both beauty and functionality. A separate staircase leads to a charming loft overlooking the kitchen, creating an open and inviting atmosphere. The formal dining room and large living room each feature working fireplaces, adding timeless charm and cozy ambiance. Relax in the cozy sunroom located off the kitchen. The house also features a Sonos sound system and Lutron lighting throughout. The property continues to impress with a newly renovated 20' x 40' heated inground pool, ideal for entertaining, and a classic barn offering endless possibilities. This exceptional country estate is a rare offering providing the perfect balance of historic sophistication and modern comfort. Bordered by a 390 acre estate, this property is 1.5 hours north of NYC, close to Millbrook, Rhinebeck, the Culinary Institute of America, local wineries, and several historic sites on the Hudson River, with easy access to the Taconic State Parkway.

5548 Route 82, Clinton Corners
$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
$1,250,000
5 Beds ⋅ 3 Baths ⋅ 998694 MLS
Nestled on a country road in West Pine Plains, the Historic Hanlon Hill Farmstead offers a rare opportunity to own a piece of history. This 87-acre property, spanning five parcels, has been in the Hanlon family for six generations. The centerpiece is an 1840s eyebrow colonial home, set back from the road for ultimate privacy. As you enter the farm, you'll pass a serene pond and a charming one-bedroom guest cottage featuring wood floors and a beautiful brick fireplace. Currently rented for $1,000 per month, the tenant covers all utilities. The main house is a lovely blend of historic charm and modern comfort, with 4 bedrooms, 2 bathrooms, and gorgeous wide-board wood floors throughout. Nature lovers will appreciate the meadows, abundant woodlands, and diverse wildlife that surround the property. Farm roads wind through the land, leading to the highest points, where you can take in breathtaking sunset views. This land offers incredible development potential, with standing hardwoods ready for harvest, and the barn—24’ x 36’ with a metal roof—could easily be transformed into horse stalls or used for other farming needs. Whether you're an investor or an outdoor enthusiast, this property has endless possibilities. It’s ideal for hiking, hunting, or any outdoor activity you can imagine. The historic colonial features a large, covered front porch with its original door, opening into a grand staircase. To the right, a spacious living room boasts a large stone fireplace, and a small galley kitchen sits adjacent. To the left, you'll find a formal dining room and a bedroom with an antique bath, plus the main kitchen, complete with a wood stove. Upstairs, there are 3 bedrooms and a modern, fully-tiled bathroom with both a tub and shower. A cozy office or nursery is located off the largest bedroom. A three-season porch overlooks the meadows and orchard, offering a peaceful spot to relax. The property also includes a creamery, a smokehouse, and stunning stone retaining walls that add to its rustic charm. Conveniently located just off the Taconic Parkway, this farm is an easy drive to Rhinebeck, Red Hook, and Pine Plains. Whether you're looking for a serene retreat, a development opportunity, or a place to pursue farming, this historic property offers something for everyone.

303 Hicks Hill Road, Stanfordville
$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
$575,000
3 Beds ⋅ 4 Baths ⋅ 997897 MLS
Wake up to beautiful lake views from nearly every room, abundant natural light, and the peaceful beauty of one of the Hudson Valley's premier private lake communities. Designed by renowned architect Steve Haas, this exceptional contemporary waterfront home offers 3 bedrooms and 3.5 baths, with each bedroom featuring its own en suite bath, including a convenient first-floor bedroom suite ideal for guests or one-level living. Whether you're searching for a full-time residence or an effortless weekend retreat, this home offers the perfect balance of comfort, style, and privacy. Walls of glass frame the lake while filling the home with natural light throughout the day. The dramatic living room features soaring cathedral ceilings, a striking wood-burning fireplace, and generous space for entertaining, while the chef's kitchen with granite countertops flows seamlessly into the dining area, creating an inviting setting for everyday living or hosting friends. A screened porch overlooking the lake provides a wonderful place to enjoy morning coffee, unwind after a day on the water, or host dinner with friends while taking in the ever-changing views. Just off the kitchen, a private courtyard offers additional outdoor space for container gardening, a fire pit, or simply relaxing. Life here is about enjoying the Hudson Valley—not maintaining a home. Residents enjoy kayaking and swimming on the lake, tennis, a beautifully maintained community pool, and peaceful tree-lined roads perfect for walking or biking, all within an upscale community known for its exceptional setting and meticulously maintained grounds. The monthly association fee reflects the exceptional level of services provided and extends well beyond what is typically included in most communities. In addition to maintaining the pool, tennis courts, private roads, landscaping, snow removal, and common areas, the association also assumes responsibility for many exterior maintenance and replacement items that are traditionally the homeowner's responsibility. The result is a true lock-and-leave lifestyle, allowing you to spend more time enjoying the lake and less time managing the ongoing upkeep of a home. Offered fully furnished, this turnkey home is ready to enjoy from day one. Ideally located just 25 minutes from Hudson's Amtrak station and within easy reach of the Wassaic Metro-North station, owners enjoy two convenient rail options for traveling to and from New York City. Rhinebeck, Pine Plains, the Berkshires, Tanglewood, the Taconic State Parkway, and countless Hudson Valley destinations are all nearby, making this a rare opportunity to enjoy one of the Hudson Valley's most desirable lakefront lifestyles.

322 Arcadia Drive, Ancramdale
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