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$649,000
5 Beds 3 Baths 1049359 MLS
Space, privacy, and possibility in the heart of Clinton Corners! Set on approximately 3.3 acres, this expansive two-family home offers nearly 4,000 square feet of living space and an exceptional blend of versatility and Hudson Valley charm. The main residence features 3 bedrooms and 2 bathrooms, with a generous layout that lives larger than most homes. A welcoming formal entry leads into an inviting open-concept living space where the kitchen, dining area, living room, and den flow seamlessly together—perfect for relaxed everyday living and effortless entertaining. Step outside onto the spacious deck for alfresco dining, sunset gatherings, or quiet mornings with coffee. Down the hall, two generously sized bedrooms accompany a private primary suite with its own ensuite bath. The lower level offers an impressive 2-bedroom, 1-bath apartment with a large kitchen and living room, creating an ideal setup for guests, extended family, or rental income. A two-car garage and dedicated workshop space add even more functionality for hobbies, projects, and storage. Outside, a storage shed and expansive green yard provide plenty of room for gardens, a pool, outdoor entertaining, or play. Whether envisioned as a full-time residence, weekend retreat, multi-generational home, or income-producing property, 226 Charwill Drive offers the space and flexibility to create your own Hudson Valley lifestyle. Conveniently located just minutes from the Taconic State Parkway and approximately 90 minutes from NYC, with the villages of Rhinebeck and Millbrook only about 10 minutes away. Enjoy farm-to-table dining, boutique shopping, local farms, vineyards, and the many cultural and historical treasures that make the Hudson Valley such a special place to call home.

226 Charwill Drive, Clinton Corners

$2,800,000
3 Beds 4 Baths 1047722 MLS
Set on 9.25 acres of open meadow in Milan, 15 Ferris Lane is a to-be-built contemporary country home conceived and designed by APS Designs, a multidisciplinary design studio, and developed by AELO. The residence takes its cues from the familiar forms of the Hudson Valley and reimagines them through a distinctly contemporary lens. A series of interconnected gabled volumes will stretch across the landscape, combining clean geometry, natural materials, and expansive walls of glass with a warmth and restraint that feel entirely at home in the setting. Symmetrical and timeless in character, the design is grounded in a strong sense of place while introducing inventive new elements. The entrance porch evokes the formality and symmetry of an Italian Palladian villa, creating an iconic arrival. Above, it becomes a panoramic terrace accessed from the second floor, offering an elevated connection to the surrounding landscape. At the heart of the house will be a soaring, barn-like great room whose dramatic volume opens to the landscape through oversized windows and doors. The living, dining, and kitchen areas will flow together, with a mezzanine above adding another layer of space and perspective. Three bedrooms will occupy the quieter wings of the house, creating separation between private and communal spaces. At the rear, the principal living areas will open onto an expansive deck and outdoor entertaining area overlooking the pool and surrounding countryside. The residence will comprise approximately 2,550 square feet on the main level, together with a 730-square-foot mezzanine and an attached 576-square-foot two-car garage. The 9.25-acre property begins along a quiet country road and rises through open meadow to an elevated homesite with long views across neighboring farmland and the rolling hills beyond. The house has been carefully positioned to take full advantage of the setting, with its principal living spaces and terraces oriented toward the surrounding countryside. Founded by Antonio Pio Saracino—an Italian designer and artist licensed to practice architecture in Italy—APS Designs is a multidisciplinary studio whose international projects are shaped by a strong sense of place and span the built environment, interior design, furniture, and art. Saracino’s work is represented in the permanent collections of institutions including the Centre Pompidou, the Brooklyn Museum, and the Los Angeles County Museum of Art, and has been exhibited internationally, including at the Venice Biennale. At 15 Ferris Lane, APS Designs has conceived a contemporary country house for AELO that is firmly rooted in the traditional landscape of the Hudson Valley while establishing a distinctive identity of its own. Estimated delivery Spring 2027.

15 Ferris, Red Hook

$499,000
2 Beds 2 Baths 1049475 MLS
Welcome to 559 Lake Road in Pine Plains! Boasting direct views and access to Twin Island Lake, this beautiful property has it all, lake and mountain views! 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

$695,000
3 Beds 2 Baths 1047455 MLS
Set among majestic trees with the gentle sound of a creek below, Turkey Hill is a warm and tranquil country home where soaring ceilings, exposed beams and log home character create an inviting sense of place. A large covered front porch sets the tone. It is the kind of spot made for slow mornings with coffee, long summer evenings and rocking chairs, with birdsong in the trees and the creek in the distance. Inside, cathedral ceilings give the main living space a striking sense of volume, while exposed wood beams throughout the home bring warmth and character from room to room. At the heart of the living room, a wood-burning fireplace with a dramatic stone surround creates a natural gathering place, while a propane stove offers another cozy source of warmth. The kitchen pairs the home’s rustic character with a clean, updated feel, including new quartz countertops and direct access to a side deck leading to the fenced backyard and garden. Off the living room, a light-filled sunroom is currently used as a home office and reading nook, with windows framing views of the surrounding landscape and creek. The sunroom also connects directly to the primary suite, creating an easy flow between the spaces. The primary bedroom includes a walk-in closet and its own private full bathroom, all within a warm, wood-clad space with a high, open ceiling. Upstairs, two equally sized bedrooms share a second full bathroom. Between them, a generous open landing overlooks the living room and fireplace below, further enhancing the home’s open and airy feel. The landscape is just as much a part of Turkey Hill as the house itself. Gardens, old stone walls and a lush meadow give the property the feeling of a country home that has settled naturally into its surroundings. A short trail winds through the meadow to the creek, creating a serene destination of its own just beyond the house. The fenced backyard provides a defined space for gardening, pets and play while still feeling connected to the larger landscape. A full, unfinished walkout basement provides generous room for a workshop, storage and hobbies. The heated detached two-car garage offers even more flexibility, with abundant additional space in the upper attic level, and a new whole-house generator provides added peace of mind. For all its privacy and sense of seclusion, Turkey Hill is remarkably connected. The Taconic State Parkway is just minutes away, putting New York City under two hours from home, while Red Hook, Rhinebeck and Tivoli are all within 10-20 minutes. Together, these beloved Hudson Valley towns offer some of the area’s best restaurants, cafes, shops and markets, making Turkey Hill a desirable country retreat with the best of the region close at hand.

1262 Turkey Hill Road, Red Hook

$895,000
2 Beds 1 Baths 1045934 MLS
Tucked away on 18+ acres off a designated scenic road sits this bright and charming country cottage. A long driveway leads to the cottage offering complete privacy with mature trees, wildlife, stone walls and a seasonal pond. This home has just undergone a total exterior renovation including new Marvin windows, Hardie Board siding, and insulation. Inside you will find polished concrete floors with radiant heat creating warmth throughout, custom cabinets and black walnut countertops, a Harman pellet stove, and separate wood burning fireplace. Comfortably live on the first floor with its cozy bedroom adjoining the European style bathroom with a vintage, cast iron clawfoot tub. The lofty and serene upstairs is currently configured as one spacious room but can easily be converted to two bedrooms with a bath. The cottage offers the flexibility to serve as a charming guest house should a future main residence be built. Immerse yourself in the peace and natural beauty of this rare property, with trails winding throughout the surrounding woodlands. A quick drive to the village of Stanfordville, and close to Millbrook, Pine Plains, and Rhinebeck. Two hours from Manhattan.

8 Old North Anson Way, Stanfordville

$800,000
5 Beds 4 Baths 1044978 MLS
Looking for a Dutchess County home with acreage, mountain views, guest accommodations, and flexible living space? Set on 5.16 acres in Stanfordville, this one of a kind property offers nearly 2600 square feet of living space along with an expansive outdoor oasis, multiple outbuildings, and separate accommodations currently used as an Airbnb. Inside the 4 bedroom, 2.5 bath main home, a spacious kitchen offers abundant cabinetry, generous counter space, stainless steel appliances, and a large peninsula. Multiple living and dining areas and a dedicated home office provide room to spread out, while a wood-burning stove framed by an exposed brick wall creates a distinctive gathering space with direct access to the expansive back deck. Upstairs you will find 4 spacious bedrooms, including a primary suite with a private bath and balcony. The apartment is above the detached 2 car garage, with a separate exterior entrance, separate utilities and dedicated elevated deck, creating added separation and flexibility for guests. Inside are comfortable living and dining areas, a kitchen with ample cabinetry and counter space, a bath, and bedroom space with generous closet storage. The private deck with pergola provides an additional outdoor sitting area overlooking the surrounding greenery. Currently used for short-term accommodations, this portion of the property may appeal to buyers searching for a home with guest quarters, separate living space, or potential income. Buyers should verify applicable permits, approvals, and requirements for continued short-term rental use. Beyond the home, more than five acres of park-like landscaped and open grounds create an impressive outdoor setting framed by mountain and countryside views. The property features a large multi-level back deck with space for dining, grilling, and entertaining, along with a landscaped fire pit area, backyard irrigation system, a fountain water feature, barn, shed, an additional outbuilding and expansive open lawn areas. The property also has riparian rights on Wappingers Creek and the Buttercup Farm Audubon Sanctuary is next door, adding even more splendor to this nature lover’s paradise. On the more practical side, heating and cooling is well covered, with mini-splits in the main home on the 1st floor that provide AC and heat as well as 8 zones of oil-fired hydronic baseboads. The apartment has mini-split heat and air conditioning in addition to the electric baseboard heat. The leased solar panels at $212/month cover the main house electric usage, owners currently only pay a $48 delivery fee. The accessory apartment is on a separate meter and runs $85-$100/month. A portable generator and transfer switch adds peace of mind. Located in the Pine Plains School District, this property offers an uncommon combination of exquisite property, flexible accommodations, outdoor entertaining space, and 360-degree Hudson Valley scenery.

6725 - 6727 Route 82 Unit #6725, Stanfordville

$525,000
3 Beds 2 Baths 1046543 MLS
Charming Cape Cod Retreat on Nearly 6 Acres in Pine Plains. Tucked away on a quiet country road just outside the village of Pine Plains, this charming three-bedroom, two-bath Cape Cod offers the perfect blend of country tranquility, comfortable living, and endless possibilities on nearly six beautiful acres. Welcoming you home with its cheerful yellow exterior, the spacious main level features a comfortable living room, dining area, kitchen, and convenient three-quarter bath. Upstairs, you’ll find three bedrooms and a second full bath, providing plenty of room for family and guests. The walkout basement offers excellent potential and could easily become a creative studio, workshop, hobby space, home gym, or additional living area. A one-car garage with storage below adds even more practicality and space. Step outside onto the generous rear deck and take in the peaceful surroundings. The home is privately set back from the road among mature trees and a shady lawn, while the wooded portion of the property offers something truly special: two streams that converge on the property, creating a picturesque natural setting. Behind the house is a large, sunny open area with plenty of room for gardening, outdoor games, entertaining, or simply enjoying the beauty and privacy of your own country retreat. The location is equally appealing. You’re close to local farms, restaurants, galleries, and music venues, with numerous hiking, biking, and outdoor recreation opportunities within an easy drive. Nearby Millerton, Rhinebeck, and other Hudson Valley destinations offer even more shopping, dining, and entertainment. Located less than a two-hour drive from Manhattan and a short 20 minute drive to the nearest Metro north train station, this property is ideally suited as a peaceful weekend getaway, vacation retreat, or full-time country home. With nearly six acres, beautiful natural features, flexible living space, and a wonderful Hudson Valley location, this is a rare opportunity to create your own private escape in Pine Plains.

404 Schultz Hill Road, Pine Plains

$125,000
1043549 MLS
Discover the opportunity to create your own Hudson Valley retreat on this 4-acre parcel in the Town of Milan. Located along an established residential stretch of Fitzsimmons Road, this property offers a peaceful country setting with convenient access to Red Hook, Rhinebeck, Route 199 and the Taconic State Parkway. The parcel is located in Milan’s A3A Agricultural District, where residential and agricultural uses are permitted subject to applicable Town and County approvals. With approximately 4 acres, the property exceeds the district’s basic 3-acre minimum lot-size requirement and may offer potential for a future homesite. Enjoy the privacy and natural surroundings of rural Dutchess County while remaining within easy reach of shopping, dining, recreation and the charming Hudson Valley communities of Red Hook and Rhinebeck. Buyer and buyer’s agent to independently verify zoning, road frontage, survey, septic/BOHA requirements, driveway approval, wetlands, utilities and all intended uses with the appropriate municipal agencies.

Fitzsimmons Road, Red Hook

$695,000
3 Beds 2 Baths 1042095 MLS
Presenting Hunns Lake House, an inviting country home set along the shores of Hunns Lake, a private residential lake tucked into the countryside of Stanfordville. The property features 150 feet of lakefront and beautiful water views from nearly every room, including a striking glass-enclosed dining room that looks out over the lake. With no motorboats permitted, lake life here is truly irresistible. Enjoy morning swims, afternoons kayaking or paddleboarding, and long evenings watching the light move across the water. Built in 1960, the three-bedroom, two-bath home offers an expansive 3,688 square feet, all on one level. Generous rooms and abundant windows fill the house with natural light. The glass-enclosed dining room opens directly into the living room, where a beautiful stone fireplace brings warmth and character. The large country kitchen centers around an island with plenty of room to cook and gather, while an incredibly spacious family room with a wood stove offers another place to settle in, spread out, and spend time together. The water is a constant presence here. It’s beautiful in every season, from long summer days spent swimming and paddling to crisp fall mornings and snowy winter views from beside the fire. Conveniently located between Millbrook and Rhinebeck, with the hamlets of Stanfordville and Pine Plains just minutes away and New York City less than two hours away, Hunns Lake House is a wonderfully relaxed place to escape to, and an even better place to call home.

119 W Hunns Lake Road, Stanfordville

$450,000
1 Beds 1 Baths 1036155 MLS
Here is a truly exceptional opportunity to enjoy the peaceful lifestyle that comes with lakefront living. Immerse in the sounds of nature, enjoy the changing seasons, spend warm summer days kayaking on the lake, and relax in a setting that feels like a true departure from the everyday. Welcome to your sweet escape at 31 Lake Shore Drive, a charming cottage with an open floor plan and vaulted ceiling that's well suited for year-round living. The flexible layout allows you to use the home as either a one- or two-bedroom, depending on your needs. Imagine enjoying dinner every evening with the lake as your backdrop or unwinding on the rear deck while taking in the beautiful water views. From morning coffee at sunrise to relaxing evenings by the water, this home offers a peaceful place to create lasting memories with loved ones and friends. You will enjoy the benefit a spacious basement and a detached one-car garage, providing plenty of storage for outdoor equipment, seasonal items, or hobbies. Situated on nearly half an acre with mature trees for an added buffer of privacy, there's ample room for outdoor activities, entertaining, gardening, or simply enjoying the open space. Whether you're looking for a full-time residence or a weekend retreat this oasis offers the comfort, charm, and lifestyle that make lakefront living so special. It all awaits you! Make it yours today. Please do not go on the property without a confirmed appointment. Schedule a tour today.

31 Lake Shore Drive, Pine Plains

$650,000
1034674 MLS
Discover the potential of this well-equipped 11.3-acre horse farm, offering an ideal setup for equestrian enthusiasts, trainers, or those looking to create their own private country retreat. The property features a spacious 10-stall barn complete with running water, a convenient half bath, septic system, 200-amp electric service, and ample space to support a variety of agricultural or equestrian uses. With open acreage and room to expand, this property provides endless opportunities for boarding, training, recreation, or simply enjoying the rural lifestyle. Whether you're starting a new venture or bringing your horses home, this versatile property is ready for your vision. All details to be verified by buyer's agent.

151 Homan Road, Stanfordville

$549,000
3 Beds 1 Baths 1030131 MLS
Zoned commercial/residential, full of character with beamed ceilings, and set on 1.1 acres, this classic 1943-built Colonial home, approximately 1,400 sq ft, offers 3 bedrooms and 1 bath, with an enclosed back porch that's a perfect place to work from home or relax anytime of the day or evening. The unfinished basement with outside entrance provides excellent storage and houses the washer and dryer. A standout feature of this property is the detached garage built in 1992, a spacious 2,040 sq ft structure with room for up to 3 vehicles. Currently used for auto repair and miscellaneous activities, it also includes an unfinished attic for additional storage or expansion potential. Whether you're a car enthusiast, hobbyist, or in need of a workshop, the garage is a rare find and has tons of parking! Conveniently located in Stanfordville, NY, this property blends small-town charm with practical space and versatility, and provides a wonderful opportunity for those seeking a home with character and charm, along with the potential for a retail store, office, artisan studio, or light manufacturing. Come take a look and see the possibilities for yourself! TONS OF IMPROVEMENTS to include: new windows in the house 2008, a new oil tank 2008, new porch windows and siding 2012, new well pump and tank 2015, updated 200 AMP service 2016, garage painted and new upstairs attic windows 2019, new roof on garage 2019, new roof on porch 2020, and new roof on house 2021, mini-splits installed 3 in the house and 2 in the garage 2021, a water softener and sulfur filter in 2021, new furnace and separate bathroom zone 2023, new septic lines from house to tank 2025, set of septic lines ran to under the porch for future use and 1,000 gal septic tank pumped 2025. There are 2 separate electrical services. 150 AMP to the garage, and 200 AMP to the house. The well may be able to supply the garage, but you may need a separate septic tank to service the garage. This property was reassessed in May 2026 with an increase in value to $414,500. Additional photos to follow. Buyer/Buyer's Agent to verify all information.

5915-5917 RT-82, Stanfordville

$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

$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

$359,000
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

$389,900
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

$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

$140,000
1010757 MLS
Ready to build your Hudson Valley dream home? Save numerous months of engineering expense and time with this fully Board of Health Approved 3.45-acre parcel, pre-tested and permitted for a 4-bedroom residence! (Please note: the image of the home in the listing pictures is a POSSIBLE concept created by AI using the land photos.) A rough-cut driveway leads up to a secluded, elevated building site nestled at the top of the hill, offering exceptional privacy, natural breezes, and seasonal Stissing Mountain views. The heavy lifting with county health board approval is already done—making this an ideal canvas for a custom build, country getaway, or spec construction. Located just a short distance from Twin Lakes and the Thompson Pond Preserve, your days can be filled with hiking, kayaking, and taking in the iconic Hudson Valley vistas. Enjoy the local community charm of Pine Plains while staying just a short drive from the cultural hubs of Red Hook and Rhinebeck. From winter skiing to summer river excursions, this property delivers the quintessential upscale country lifestyle. Easy to show—just log and go through showing service.

66 Ryan Road, Pine Plains

$3,950,000
1018855 MLS
An intoxicating opportunity to own a 343 acre swathe of spectacular farmland, proudly eligible for the National Register of Historic Places, that encompasses several impressive barn structures, plus a fully functioning distillery and tasting room. Dutch's Spirits, on Harvest Homestead Farm, is a distillery with a legacy! Harvest Homestead Farm has endless potential. Through the years it has been a productive farm raising turkeys, chickens, pigs and cows, potatoes and corn. It's waiting for someone with vision to perhaps keep the distillery and tasting room going, revive it as a full-time farm, or open a sprawling indoor-outdoor event space. The location is superb: the property neighbors the increasingly popular Mashomack Fish & Game Preserve Club, a 1,900-acre private sporting preserve and social club. The picturesque hamlet of Pine Plains is within a thirty minute drive to the increasingly hip cultural and dining hubs of Hudson and Rhinebeck and only two short hours to Manhattan.

70-98 Ryan Road, Pine Plains

$3,495,000
1014454 MLS
Rarely does a property of this caliber become available. Spanning approximately 234 acres across two contiguous parcels (162 acres and 71.5 acres), this exceptional offering features productive hay and corn fields, rolling farmland, mature woodlands, and breathtaking long-range views of the Taconic Mountains and Catskills. Multiple elevated building sites provide the opportunity to create a private estate, compound, or working farm with spectacular panoramic views. Lovingly stewarded by the same family for generations, the land has been actively farmed and maintained, offering fertile soils and endless possibilities for agriculture, equestrian pursuits, recreation, or development. Private, scenic, and remarkably versatile, this is a rare opportunity to own a significant piece of Hudson Valley countryside.

317 Skunks Misery Road, Millerton

$875,000
3 Beds 3 Baths 1006691 MLS
LOCATION, LOCATION, LOCATION!!! MUST SEE this Stanford gem nestled in Clinton Corners, offering endless possibilities with the perfect blend of country tranquility and modern comfort. Set on 2.6 peaceful acres, this beautifully maintained Ranch-style home delivers private and effortless living with its efficient layout. The front porch reveals mountain views and a lovely place to reflect on the day. A small seasonal pond anchors the property, and a picturesque backyard with a 1,000sf Trex deck and permanent screened gazebo, expands your living space and creates a serene backdrop for everyday living and entertaining. A 1,500sf pole barn/workshop, approximately 50ft x 30ft, provides endless possibilities for work, hobbies, storage, or creative pursuits. Inside, the thoughtfully designed layout features three bedrooms and three full baths with flexibility for guests. A dedicated home office /guest room tucked away from the main living area provides the ideal work-from-home space or au pair room. The wood-burning fireplace in the living room presents a cozy space to share with loved ones. Touches of Hygge & West wallpaper add colorful accents throughout. The heart of the home features a gas-burning stove and floor-to-ceiling windows, and flows seamlessly to the deck overlooking the pastoral grounds, perfect for outdoor dining, morning coffee, or evening gatherings under the stars. A charming, permanent screened gazebo with a wood ceiling invites you to relax and enjoy the natural setting in comfort throughout the seasons. An attached one-car garage adds convenience, while the expansive property showcases room to roam, garden, or unwind in complete tranquility. Improvements with permits include a 1000sf TREX deck with a permanent screened gazebo, central air conditioning, and a rebuilt chimney. A rare opportunity to enjoy refined country living with space, versatility, and timeless appeal within a short drive to the Taconic State Parkway, Millbrook, Rhinebeck, restaurants, wineries, farmer's markets, and all the conveniences the Hudson Valley has to offer! This Stanford retreat is as peaceful as it is beautiful! Schedule your viewing today!

133-141 Shelley Hill Road, Stanfordville

$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

$170,000
1006768 MLS
Build Your Waterfront Forever Home: 5.10 Picturesque Acres along the Jan Kill River. Close your eyes and listen to the gentle, rhythmic sound of rushing water. Imagine stepping out onto your future back deck with a warm cup of coffee, watching the morning mist rise over the river as the sun filters through the trees. This isn't just a piece of land—it is the canvas for your dreams and the sanctuary where you can finally build your waterfront forever home. A Rare 5.10-Acre Connected Estate - Tucked away in the beautiful, serene town of Milan, NY, this exceptional offering combines two connected parcels to give you the ultimate layout of privacy, space, and flexibility. The Residential Foundation: A 1.30-acre residential lot (in Gallatin) serves as your perfect building cornerstone. The Natural Oasis: An adjoining 3.8-acre lot (in Milan) seamlessly expands your estate, culminating in direct, private frontage right along the banks of the Jan Kill river. Together, these parcels create a generous 5.10-acre riverfront retreat where you can hike your own woods, listen to the water flow, and let the stresses of the world completely melt away. Secluded Peace Meets Modern Convenience - While this property feels like a private forest world entirely your own, it balances deep natural peace with effortless accessibility to the very best of the Hudson Valley. Effortless Commute: Located just 3 minutes from the Taconic State Parkway, making travel a breeze. Minutes to Culture & Dining: A brief 10-minute drive brings you directly into the historic, vibrant centers of Red Hook and Rhinebeck. Spend your afternoons and evenings exploring renowned farmers markets, enjoying fine dining, and taking in local entertainment. Opportunities to own a multi-acre riverfront parcel this close to the Hudson Valley's most coveted towns are incredibly rare. Bring your architect, bring your vision, and break ground on a lifetime of beautiful memories!

Jackson Corners Road, Red Hook

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