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$795,000
1012733 MLS
Exceptional investment and development opportunity in the heart of the Hudson Valley. Located within the Town of Red Hook's Traditional Neighborhood District Commercial Center, this unique offering consists of two separate parcels totaling 1.8 acres and includes two residential structures. The primary structure is an occupied three-bedroom, one-bath home. The second building offers flexibility as a potential three-bedroom, two-bath residence, office space, or a combination of residential and commercial use, subject to local approvals. The property is serviced by two recently installed cesspools and is positioned in a highly visible and desirable location just a short walk from the Village of Red Hook's shops, restaurants, and amenities. With its prime location, flexible zoning, two separate parcels, and multiple existing structures, this property presents a rare opportunity for investors, business owners, developers, or owner-occupants seeking a live/work environment in one of the Hudson Valley's most desirable communities. A unique offering with exceptional potential in the center of Red Hook's thriving commercial corridor.

7318 S Broadway, Red Hook
$1,600,000
1011611 MLS
Stoneledge is a fully approved nine-lot subdivision nestled in the woodlands of Red Hook, New York — an exceptional opportunity for builders, developers and investors ready to move without the years of entitlement work already behind them. Set along Medwyn Lane at the intersection of Springlake Road in Dutchess County, the offering consists of nine residential lots ranging from 1.5 to 1.9 acres each, plus an additional 17 acres of contiguous land included in the package. One lot features a partially completed structure, giving the right buyer a head start on their first delivery. The remaining eight sites are raw, wooded and ready for ground-up development. The land carries everything the Hudson Valley does best — mature tree canopy, natural privacy between lots, rolling terrain and the kind of quiet that buyers at this price point are specifically chasing. Red Hook's village center, the Rhinebeck corridor, Amtrak service at Rhinecliff and the Taconic State Parkway are all within minutes. The full portfolio is offered at $1,600,000. Individual lot purchases will also be considered for the right buyer. Whether you're looking to take down the entire project or start with a single site, Stoneledge is positioned to deliver.

Medwyn Lane, 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
$1,200,000
1009767 MLS
Unique offering with this LEGAL 7 unit Multifamily. Full occupancy with great reliable tenants. Unit one is 2 Bedroom, 1 full bath, Unit two is 1 Bedroom, 1 Full Bath, Unit Three is a 2 Bedroom, 1 Full Bath, Unit Four is 2 Bedroom, 1 Full Bath, Unit Five is 2 Bedroom 1 Full Bath, Unit Six is 1 Bedroom, 1 Full Bath Unit Seven a 3 Bedroom, 1Full plus 1/2 Bath. TOTAL of 13 Bedrooms and 7 plus 1 1/2 Baths. Property has been maintained to perfection, and the grounds have a Park-Like quality with Gazebo and outdoor track for recreation and is mostly fenced. There are several outbuildings that provide additional income and versatile usage. Located conveniently within 10 minutes to TSP and Villages of Red Hook and Rhinebeck in the Red hook School District. Don't miss this opportunity to invest in this turnkey money maker!

1030 Route 199, Red Hook
$539,000
3 Beds ⋅ 2 Baths ⋅ 1008213 MLS
Move right into this beautifully renovated 3-bedroom, 2-bath ranch nestled on 2 private acres just minutes from the Village of Red Hook. Thoughtfully updated throughout, this home offers spacious living, all-new flooring, a first-floor primary bedroom, and a finished walkout lower level with a private entrance—perfect for guests, a home office, or flexible living space. Enjoy the peace and privacy of your own scenic property complete with a picturesque pond, while remaining just minutes from Red Hook, Rhinebeck, Bard College, Amtrak, local restaurants, wineries, shopping, and outdoor recreation. Offering the perfect blend of modern updates, convenience, and serene Hudson Valley living, this move-in-ready home is one you won’t want to miss.

287 Norton Road, Red Hook
$850,000
3 Beds ⋅ 3 Baths ⋅ 1006694 MLS
A rare opportunity to own a piece of Red Hook history. Offered for the first time in 117 years, this cherished family home has been lovingly maintained through generations and retains many of its original architectural details and timeless character. Located in the heart of the Village of Red Hook, the home showcases beautiful original wood floors, classic moldings, detailed staircase trim, and the craftsmanship rarely found in today's construction. The spacious floor plan features 3 bedrooms, 2.5 baths, and two dedicated office areas, providing flexibility for remote work, creative pursuits, or additional living space. Outside, an oversized detached two-car garage offers ample room for vehicles, storage, or a workshop. Conveniently situated near village shops, restaurants, parks, and schools, this exceptional property combines historic charm with everyday convenience. A truly special offering ready for its next chapter.

64 W Market Street, Red Hook
$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
$575,000
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
$595,000
3 Beds ⋅ 3 Baths ⋅ 999126 MLS
Opportunity awaits at the end of a quiet dead-end road with sweeping panoramic views of the Catskill Mountains. Set on 1.3 acres, this 3-bedroom, 2.5-bath ranch-style home offers incredible potential for contractors, investors, or buyers ready to create a one-of-a-kind Hudson Valley retreat. Located just minutes from the village of Red Hook and convenient to Bard College, Rhinebeck, and Hudson, the property combines privacy with accessibility. Inside, the home features a desirable one-level layout with an open floor plan, generous living spaces, and a fireplace ready to become the centerpiece of a stunning renovation. The house requires a complete renovation, presenting a rare opportunity to reimagine and restore a home in an exceptional setting. With breathtaking mountain views, a peaceful location, and endless potential, this is a true Hudson Valley diamond in the rough. Sale subject to appointment of executor.

97 Spencer Drive, Red Hook
$2,495,000
4 Beds ⋅ 4 Baths ⋅ 990285 MLS
This cheerful c.1850 farmhouse captures the essence of Hudson Valley country living with a gracious wraparound porch, sweeping lawns, and classic barns. Filled with natural light, the house features high ceilings, original moldings, beautiful built-in cupboards and wood floors throughout. A traditional center hall opens to an expansive living room anchored by a Rumford-style fireplace, custom bookshelves, and charming window seat. The renovated kitchen and dining area create an inviting open-concept space ideal for everyday living and entertaining, featuring an Aga range and stainless steel appliances. The first-floor primary suite offers a spa-like bathroom with soaking tub, radiant heat, and a generous walk-in closet. Upstairs, a second ensuite bedroom is joined by two additional bedrooms and a bright laundry room. The third floor provides flexible space for a studio, music room, office, or meditation retreat. Thoughtful updates include a practical mudroom with pantry, new furnace, central air, a B-Dry basement system, and a solar array. Vintage barns, including a handsome three-story Dutch barn, are surrounded by rolling lawns, mature trees, and old apple orchards. Complete with a potential hilltop building site, this property offers numerous possibilities for a small farm, a custom home, dedicated studio/workshop space and more. A private saltwater swimming pool, fenced garden, and an historic stone summer kitchen complete the over 18-acre property spanning two adjacent parcels. According to local historians, Meadow Brook Farm has only had seven owners since 1688 when King James the II gave Dutchman, Pieter Schuyler a patent for the property. With wide-open skies, timeless pastoral beauty, and exceptional space for gathering and retreat, this is a uniquely beautiful Hudson Valley offering.

71 Starbarrack Road, Red Hook
$749,000
3 Beds ⋅ 2 Baths ⋅ 998584 MLS
Beautiful parklike setting on over 7 private acres in the heart of the Hudson Valley. Tucked well off the road, this one floor living home offers exceptional privacy surrounded by mature trees, rock outcroppings, and a stream. Enjoy the outdoors from the wrap-around deck or explore your own wooded acreage. Inside, the main living areas have an open kitchen with Craft-Maid hickory cabinets, quartz soapstone counters, black stainless steel appliances and hardwood floors. Plenty of bright views out of the sliding doors to the porch overlooking the expansive back yard. The two car garage enters into the laundry room and provides easy access during any type of weather. The basement features two oversized windows, a sliding door, and would be a great additional space, the interior and exterior access make it very versatile. Two wooden outbuildings provide additional storage or workspace. Follow paths down to the stream for outdoor fun. Great for nature lovers and convenient to Red Hook and Rhinebeck, with easy access to the Taconic Parkway for a convenient NYC commute.

128 Sawmill Road, Red Hook
$436,999
3 Beds ⋅ 1 Baths ⋅ 995777 MLS
Welcome home!! Affordable Red Hook home with acreage and privacy without huge price tag. Updated 3 bedroom home in a quiet setting. Enjoy the retreat like yard, with nature trail. Recent enhancements includes: Generator 2025, range, refrigerator and microwave 2025, water heater coil 2025. 500 gallon oil tank tested in 2025, no leaks, operating well. (Seller is offering a $2500 credit toward future replacement). Roof 2024, fencing 2024, water softener 2024. Boiler 2019. Chimney flue cleaned 2024. Windows about 5 years old. Most furniture for sale. This will not last!

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

1429 Jackson Corners Road, Red Hook
$2,600,000
995594 MLS
This listing is a rare opportunity to acquire 210 Acres, income-producing orchard in the heart of the Hudson Valley. This farm has been owned and operated for four generations and is a well-established agricultural operation serving multiple regional markets. Large, contiguous, and fully operational farms of this scale, combined with protected open space and extensive infrastructure are increasingly rare in the Hudson Valley. Offering includes: 5-bedroom 1800’s farmhouse, a cottage/guest house, a Large Barn and Silo, generous root cellar, large four-bay Garage, extensive packing house with cold storage facility with an 18,000-bushel storage capacity and truck loading bay. Also, there is a fully operational cider house. The Farm produces a diverse range of fruits and vegetable, and products are currently distributed to multiple established market locations. Two on-site lakes provide for abundant water resources. A comprehensive irrigation system supports the entire farm. The property is subject to a Scenic Hudson Conservation Easement, ensuring the long-term protection of open space and agricultural use. This preservation enhances the property’s environmental value and scenic character while allowing for two additional residences in designated locations. This offering presents an exceptional opportunity for an established farm and orchard operators, vineyard, destination venue, livestock, or development, 2 residential homes, agri-business investors or anyone seeking long terms land stewardship assets. Permitted Uses in the 9 acre parcel the easement allows for crops, livestock, and livestock products. Also, allowed is the right to construct or enlarge the commercial existing structures. 2 - Single family dwellings can be constructed in and around the barns and lake views. Subject to a Scenic Hudson conservation easement preserving open space and agricultural use. The property supports ongoing farming operations, agricultural improvements, and limited residential/commercial development in designated areas, all subject to easement provisions.

245 Guski Road, Red Hook
$2,600,000
995585 MLS
This listing is a rare opportunity to acquire 210 Acres, income-producing orchard in the heart of the Hudson Valley. This farm has been owned and operated for four generations and is a well-established agricultural operation serving multiple regional markets. Large, contiguous, and fully operational farms of this scale, combined with protected open space and extensive infrastructure are increasingly rare in the Hudson Valley. Offering includes: 5-bedroom 1800’s farmhouse, a cottage/guest house, a Large Barn and Silo, generous root cellar, large four-bay Garage, extensive packing house with cold storage facility with an 18,000-bushel storage capacity and truck loading bay. Also, there is a fully operational cider house. The Farm produces a diverse range of fruits and vegetable, and products are currently distributed to multiple established market locations. Two on-site lakes provide for abundant water resources. A comprehensive irrigation system supports the entire farm. The property is subject to a Scenic Hudson Conservation Easement, ensuring the long-term protection of open space and agricultural use. This preservation enhances the property’s environmental value and scenic character while allowing for two additional residences in designated locations. This offering presents an exceptional opportunity for an established farm and orchard operators, vineyard, destination venue, livestock, or development or 2 residential homes, agri-business investors seeking long terms land stewardship assets. Permitted Uses in the 9 acres parcel the easement allows for crops, livestock, and livestock products. Also, allowed is the right to construct or enlarge the commercial existing structures. 2 residential dwellings can be constructed in and around the barns and lake views. Subject to a Scenic Hudson conservation easement preserving open space and agricultural use. The property supports ongoing farming operations, agricultural improvements, and limited residential/commercial development in designated areas, all subject to easement provisions.

245 Guski Road, Red Hook
$2,600,000
994405 MLS
This listing is a rare opportunity to acquire 210 Acres, income-producing orchard in the heart of the Hudson Valley. This farm has been owned and operated for four generations and is a well-established agricultural operation serving multiple regional markets. Large, contiguous, and fully operational farms of this scale, combined with protected open space and extensive infrastructure are increasingly rare in the Hudson Valley. Offering includes: 5-bedroom 1800’s farmhouse (currently a bunk house for employees), a cottage/guest house, a Large Barn and Silo, generous root cellar, large four-bay Garage, and an extensive packing house with cold storage facility with an 18,000-bushel storage capacity and a truck loading bay. Also, there is a fully operational cider house. The Farm produces a diverse range of fruits and vegetable, and products are currently distributed to multiple established market locations. Two on-site lakes provide for abundant water resources. A comprehensive irrigation system supports the entire farm. The property is subject to a Scenic Hudson Conservation Easement, ensuring the long-term protection of open space and agricultural use. This preservation enhances the property’s environmental value and scenic character while allowing for two additional residences in designated locations. This offering presents an exceptional opportunity for an established farm and orchard operators, vineyard, destination venue, livestock, or development, 2 residential homes, agri-business investors or anyone seeking long terms land stewardship assets. Permitted Uses in the 9 acre parcel the easement allows for crops, livestock, and livestock products. Also, allowed is the right to construct or enlarge the commercial existing structures. 2 - Single family dwellings can be constructed in and around the barns and lake views. Subject to a Scenic Hudson conservation easement preserving open space and agricultural use. The property supports ongoing farming operations, agricultural improvements, and limited residential/commercial development in designated areas, all subject to easement provisions.

245 Guski Guski Road, Red Hook
$7,500,000
968961 MLS
Premier 300-Acre Agricultural & Investment Estate on Route 9 – Turnkey Dairy & Creamery Operation Discover a rare and significant investment opportunity in the heart of the Hudson Valley. This expansive 300-acre property, located directly on the busy Route 9 corridor in the Town of Red Hook, offers an unparalleled combination of massive scale, modern agricultural infrastructure, and high-visibility commercial potential. The Commercial & Agricultural Engine At the center of this offering is a state-of-the-art Modern Dairy Barn, constructed in 2018. Built to contemporary standards, this 110 stall facility is ready for immediate operation, offering superior ventilation, comfort, and efficiency for livestock. Complementing the dairy operation is a separate, dedicated commercial building fully equipped for ice cream manufacturing. This facility presents a lucrative "farm-to-table" business opportunity, allowing the next owner to capitalize on the high traffic count of Route 9 for a potential creamery, farm market, slaughterhouse or agri-tourism destination. The Land & Investment Potential Spanning a massive 300 acres, the property features over a mile of road frontage across two separate roads, providing exceptional accessibility and flexibility for future potential. The land is a mix of fertile fields and scenic vistas, ideal for continuing agricultural production, equestrian use, or a long-term land-banking investment in one of Dutchess County’s most desirable towns. The Residence Anchoring the estate is a charming historic farmhouse in good condition. Whether utilized as a primary residence, a manager’s home, or converted into administrative offices for the business, this classic structure adds warmth and character to the modern commercial facilities. Property Highlights: • 300 Acres of prime Hudson Valley land. • High Visibility Location: Situated on busy Route 9, perfect for retail exposure. • Modern Dairy Barn (2018): 110 Freestall barn with a robotic milker (needs rebuilding). • Ice Cream Manufacturing Facility: Separate building housing commercial-grade equipment. • Historic Farmhouse: Well-maintained and ready for occupancy. • Exceptional Access: Over a mile of road frontage on three different roads. • Versatile Zoning Potential: Ideal for continued agriculture, agri-business, or future investment development. This is a unique chance to acquire a legacy property with the infrastructure already in place for a thriving agricultural enterprise. Perfect for investors, farmers, or entrepreneurs looking to launch a signature Hudson Valley brand. In addition to the Main Complex, included SBL's 677518 (38.4 Ac) 760494 (62 Ac) 854567 (30 Ac) 640370 (26 Ac) 670450 (10.5 Ac) to make total of 300+ Acres. Sale is real estate and equipment only, not the business; however, that is also an option.

7775 Albany Post Road, Red Hook
$2,294,000
4 Beds ⋅ 6 Baths ⋅ 988928 MLS
Nestled in the heart of the Hudson Valley, this exceptional custom-built compound offers a rare blend of elegance, privacy, and ease. Set on 3.15 acres of beautifully landscaped grounds, the property unfolds as a true retreat—featuring a main residence with a heated three-car attached garage, a legal guest house, a commercial-sized detached garage, a heated in-ground pool, pool pavilion, and multiple outdoor living spaces designed for both quiet enjoyment and memorable gatherings. The 4,900+ square foot main residence is rich in detail and thoughtful design. A gracious entry foyer welcomes you into formal living and dining rooms, while the expansive open-concept family room, with its inviting fireplace, creates a warm and natural gathering place. The gourmet kitchen, appointed with granite countertops and stainless-steel appliances, is both functional and refined. A charming breakfast nook overlooks a spacious deck and the beautifully landscaped pool complex, offering a serene backdrop for everyday living. The first-floor primary suite is a private sanctuary, with tray ceiling, custom closets, a spa-like bath with soaking tub and separate shower, and private access from the bedroom to the rear deck. A formal dining room with winscot, crown molding and hardwood floors, a well-placed laundry room, powder room, and secondary staircase leading to the heated three-car garage complete the main level. Upstairs, three generously sized bedrooms and three full baths are complemented by a comfortable sitting nook and a dedicated home office, perfectly suited for remote work or creative pursuits. The fully finished walk-out lower level expands the home’s versatility, offering a second full kitchen, fitness area, home theater with seating for nine, and a full bath, along with ample storage and dedicated mechanical spaces. The detached 36' x 32' heated garage offers exceptional flexibility, complete with a second-floor office and full bath, ideal for workspace, hobbies, or additional storage. Attached, the beautifully designed two-story guest house provides a fully self-sufficient living experience, featuring a private entrance, covered stone patio, full kitchen, living room with a striking stone fireplace, laundry, and two and a half baths. With its own garden and dedicated parking, this space presents an outstanding opportunity for extended living or supplemental income (Airbnb approval was never used, but can be renewed). Outdoors, the property truly shines. The backyard is a private oasis centered around a 38' x 30' heated in-ground pool, framed by custom stonework, walkways, and mature plantings. The pool house, both heated and air-conditioned, includes a changing room and a well-appointed bath. A striking covered cabana/gazebo features built-in seating and a full outdoor kitchen, complete with gas grill, refrigerator, microwave, and sink ... creating an effortless setting for summer entertaining. Additional features enhance both charm and functionality, including a small vegetable/herb garden, a gas fire pit, invisible fencing, and a custom-built kennel or chicken coop. A second gated driveway, discreetly positioned behind a stacked-stone retaining wall, provides convenient access for RV, boat, or guest parking. Extensive upgrades include 9-foot and vaulted ceilings, radiant floor heating on levels 1 and 2 (including the attached garage), Marvin Integrity windows, a high-efficiency Viessmann boiler, crown molding, LED recessed lighting, and spray foam insulation—ensuring comfort and energy efficiency year-round. Ideally located just minutes from the Taconic Parkway, Rhinebeck, and Red Hook, as well as area golf courses, wineries, spas, and fine dining, this one-of-a-kind property offers a seamless balance of seclusion and accessibility. Situated within the Red Hook Central School District.

163 Hapeman Hill Road, Red Hook
$849,000
6 Beds ⋅ 5 Baths ⋅ 985647 MLS
Shepherd’s Knoll offers rare privacy and flexibility, located less than two miles from the village. Set on four beautiful acres that include lawns, pastures, and lightly wooded areas, this distinctive property sits at the end of a long private drive. It includes two spacious living units that could easily be converted back into a single-family home. Unit One features four bedrooms, three bathrooms, and a finished lower level. Unit Two offers two bedrooms and two bathrooms with a strong history as a short-term rental. Both spaces include wood-burning fireplaces and a wood stove, creating a warm, inviting atmosphere. Outdoor living shines here. expansive decks and porches overlook pastoral views, while the grounds include a charming studio cottage, a former sheep barn with storage, chicken coops, and established garden areas. Located just minutes from Bard College, a campus that includes the Fisher Center, and Montgomery Place. The property blends country seclusion with access to Hudson Valley cultural life. Whether you need multi-generational flexibility, a home plus a guest setup, or a private sanctuary close to town, Shepherd’s Knoll offers a lifestyle that’s increasingly hard to find.

32 Old Route 199, Red Hook
$575,000
987031 MLS
A newly subdivided 16+ acre wooded lot 10 minutes from Red Hook Village 15 to Rhinebeck village and 5 miles from Taconic Parkway . Privacy plus driveway in house location staked BOHA in progress and will deliver at closing. Owner will install fill pad for septic. NEWLY SUBDIVIDED SO TAX NUMBER AND TAXES ARE NOT AVILABLE YET .This is a world class lot offering privacy , a wonderful forest and a prime location 5 minutes from Taconic , 10 minutes from Red Hook and 15 minutes to Rhinebeck and Amtrac service at Rhinecliff . NONE NICER

765 Academy Hill Road, Red Hook
$669,900
4 Beds ⋅ 3 Baths ⋅ 986710 MLS
Large, protective, ancient trees and handcrafted, artisan-made, stone walls beckon you towards this well-built, nearly 200-year-old, classic Red Hook farmhouse. This 4 Bedroom home has 3 full baths and a large bonus sunroom overlooking the yard, perfect as a private guest suite or home office with a designated entrance and full bath. The expansive 10.1-acre parcel boasts a cherry and peach tree, a spring-fed pond, a meandering stream, and acres of private woods to explore and make trails in. There is enough space for horses. Wood beams and historic remnants mark an old barn site near the pond. The unusually large, fully-fenced-in yard has iron fencing and a patio for entertaining, with ample space for a garden and a pool if desired. There are 3 bedrooms upstairs with a bathroom with pocket doors leading to the main bedroom. Laundry is upstairs as well. There is a bedroom on the first floor that could also be used as a den or library with the original hardwood flooring. The main floor has an open kitchen leading to the dining area and opening to the living room. Some of the many upgrades include new renovated bathrooms, a new roof with a warranty as of 2026, reinforced basement and stonework, updated hot-water heater, central-air, a full-house water filtration system, a storage shed that matches the home, and a Janelli security system. This is a genuinely solid home, built to last, on pastoral grounds filled with history and acres to explore. The location is perfectly serene and an ideal refuge, yet 10-minutes to the center of town. Williams Road is arguably one of the most beautiful roads in Red Hook and is quiet enough for long walks, biking, and jogging. Close to Tivoli, Bard, Rhinebeck, and the Taconic.

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

60 Stone Wall Path, Red Hook
$6,995,000
3 Beds ⋅ 5 Baths ⋅ 948111 MLS
Crestline is a visionary to-be-built residence offering 6,216 finished square feet of meticulously designed living space, including three bedroom suites and four-and-a-half luxurious baths. Pricing has been thoughtfully recalibrated to reflect the finalized construction scope and delivery approach, presenting an exceptional opportunity to secure a landmark Hudson Valley residence with enduring architectural and lifestyle value. Perched atop a private 41-acre hilltop with commanding 360-degree views of the Catskills, Stissing Mountain, and the rolling agricultural valleys below, Crestline is an architectural statement that harmonizes seamlessly with its natural surroundings. Located just minutes from Rhinebeck and Red Hook—celebrated for boutique shopping and farm-to-table dining—the property also offers effortless access to the Taconic State Parkway, placing New York City approximately 90 minutes away. Surrounded by protected farmland and open countryside, Crestline enjoys rare privacy while remaining close to hiking trails, antique markets, and the recreational offerings of the Hudson River Valley. The home’s architecture unfolds in two distinct volumes connected by a soaring triple-height glass foyer that creates a dramatic sense of arrival. The west-facing pavilion, a glass-wrapped structure that appears to float above the land, contains open-plan living and entertaining spaces designed to showcase sweeping Catskill views. Inside, 13-foot ceilings and expansive floor-to-ceiling windows flood the living room, gourmet kitchen, dining area, and library with natural light. A refined fluted-glass and steel partition subtly separates the kitchen from the dining area, while a dual-sided fireplace provides warmth between dining and great room. The library overlooks the pool and landscape, offering a tranquil retreat. Below this pavilion, inset into the slope, is a lower-level lounge and a separate pool house with full bath and sauna. The eastern volume, grounded in stone and wood, houses the private living quarters. The main level features a screening room and a serene primary suite with spa-like bath, dual walk-in closets, fireplace, and access to a secluded terrace. Upstairs, a family room and two spacious bedrooms, each with ensuite baths and walk-in closets, create a quiet retreat. Outdoor living is fully integrated into the design. A hardscaped kitchen and dining terrace with retractable shade structures extends from the foyer and great room, ideal for alfresco entertaining. The west-facing pool deck steps gracefully down the slope, aligning with the lower lounge and pool house, and includes shaded seating with a fireplace and sun-drenched lounging areas. Two rooftop gardens provide additional outdoor escapes with sweeping views. Hand-laid stone feature walls define the architectural experience, weaving indoors and out to anchor fireplaces, outdoor cooking areas, and a wet bar, while forming a stone-lined entry vestibule. A floating steel, wood, and glass staircase rises through the foyer beneath a skylight. Interior finishes reflect a modern yet grounded sensibility, pairing wide-plank oak floors and rift-cut walnut cabinetry with quartzite countertops, marble baths, and burnished brass accents. The exterior combines glass curtain wall, anodized bronze, and sustainable Accoya wood. Crestline is fully electric and sustainably designed, featuring geothermal heating and cooling, triple-pane windows, high-grade insulation, and energy-efficient systems throughout. From quiet evenings in the library to weekend gatherings around the pool, Crestline offers a rare balance of architectural distinction, immersive views, and privacy. This is not simply a home—it is a retreat where architecture and nature exist in perfect harmony.

151 Rowe Road, Red Hook
$1,500,000
947944 MLS
Set atop a sweeping 41-acre hilltop, this exceptional parcel offers commanding 360-degree views of the Catskills, Stissing Mountain, and the rolling agricultural valleys below. The property’s rare scale allows for a residence of true significance, along with ancillary uses, while preserving privacy, expansive sightlines, and a strong connection to the surrounding landscape. Properties of this size and elevation, located so close to the villages of Rhinebeck and Red Hook, are increasingly difficult to find, making this offering particularly compelling. Surrounded by active farmland and open countryside, the land benefits from productive soils well suited to agriculture, gardens, orchards, and other land-based pursuits, providing both immediate and long-term value. The terrain features an approximately four-acre hilltop plateau, encircled by naturally contoured slopes that create multiple potential building sites and a rich variety of landscape experiences. Located just minutes from Rhinebeck and Red Hook, the property offers convenient access to boutique shopping, farm-to-table dining, antique markets, and the cultural and recreational offerings of the Hudson River Valley. Hiking trails and outdoor destinations are nearby, and the Taconic State Parkway is readily accessible, placing New York City approximately 90 minutes away. With its uncommon combination of scale, views, soil quality, and proximity to vibrant village centers, this land presents a rare opportunity for a private estate, agricultural use, or legacy holding in one of the region’s most sought-after locations.

TBD Rowe Road, Red Hook
$280,000
939271 MLS
Build Your Dream Home on 7.74 Scenic Acres in Red Hook! Are you ready to turn your dream home into reality? This nearly 8-acre parcel offers the perfect blend of privacy and convenience, located just minutes from the charming shops, restaurants, and community activities of Red Hook Village. With Board of Health Approval (BOHA) in place, this property is ready for your vision — whether it’s a sprawling country estate, a contemporary retreat, or even a second home for Mom! Enjoy the tranquility of rural living surrounded by nature, while staying close to everything that makes the Hudson Valley so special.

E Kerley Corners Road, Red Hook
$3,999,000
6 Beds ⋅ 6 Baths ⋅ 921530 MLS
Nearly 30 secluded acres of rolling meadows and woodlands unfold into breathtaking panoramic views of the Catskill Mountains. This is a place to slow down and reconnect. Reminiscent of the Adirondack Great Lodges, this home is a masterful blend of rustic elegance and timeless craftsmanship. Soaring, strap-and-beam ceilings create a dramatic sense of space, while a custom-crafted staircase and a floor-to-ceiling wood-burning stone fireplace add to the home's warmth and grandeur. Step from the main living area out onto the brick patio to take in sweeping sunset views over the mountains. The expansive dining room easily accommodates large gatherings, and features a cozy window seat ideal for lounging while soaking in the views. The chef’s kitchen is both stylish and functional, featuring a beamed tin ceiling, tile flooring, and stone countertops that lend a timeless elegance. Just off the kitchen, step into your private outdoor oasis. This expansive patio features a pergola draped in mature, blooming wisteria. At the heart of the space is a fully equipped built-in barbecue station perfect for hosting al fresco dinners or weekend cookouts. A half bath, laundry room, and walk-in pantry offer added convenience, leading directly to the attached garage. The first-floor primary ensuite has westerly mountain vistas, direct access to its own private deck, and a secluded outdoor shower. Three additional bedrooms and a full bath provide ample space for family and guests. The second floor offers additional privacy and flexibility, featuring a second primary ensuite complete with a private balcony. Two more bedrooms with balconies, a full bath, and a cozy reading nook create a warm and welcoming retreat. The heated gunite pool and pool house, complete with a full bath and kitchen, are perfectly positioned to capture all-day sunlight while maintaining complete privacy. Tucked away for privacy, the Vermont Post and Beam barn adds both character and versatility to the property. Outfitted with electric and a full second-story loft, it features eaved windows that flood the space with natural light. This exceptional property exudes quiet rustic elegance, with spacious living areas, rolling lawns, and dramatic Catskill Mountain views. Located in the northeast area of Dutchess County with easy access to Red Hook, Rhinebeck, Pine Plains, Millbrook, Tivoli, Germantown, Hudson and more. Convenient to trains, Fisher Center, Bard College, private airports, excellent restaurants, farmers markets and more.

926 Turkey Hill Road, Red Hook
$1,500,000
874059 MLS ⋅ Soap Factory BLDG.
A storied site & structure located within the imminently poised-to-pop Village of Red Hook along the Rhinebeck/Hudson corridor. This is a AAA opportunity for the creative and wise user and/or investor. Its 5200+ sqft main floor & 3200sqft full height lower level is situated on 1.27 central village acres. The coveted NMU Zoning allows for a multitude of choices – eateries, retail, housing, multi-family, offices, education, day-care, medical, business, etc & etc - which Village residents, shopkeeps, students & visitors will surely welcome & support. Think other vibrant, small college towns. In the ‘40s, Eugene Callison designed this U-Shape building for a soap factory, thus the moniker. Its central courtyard provides a welcoming reception area, and the level property offers itself to further development or any alfresco activities. The Rte 9 (S Broadway) thoroughfare and sidewalks will generate quite a bit of activity for any venture and the abundant rear parking leaves the front unmarred. In recent years, costly infrastructure upgrades were implemented by the present owner for a now amended plan – See Associated Data Sheet. The dirty work is done. The Soap Factory is a historic component of Red Hook Village, and it continues to afford opportunities for a wealth of unique endeavors. This building and its land are a canvas for a number of architectural and landscape expressions. Consider perhaps a supercool village residence/studio. Insightful users & investors know growth in Red Hook is here, right now.

7392 S Broadway, Red Hook
$9,500,000
H6304822 MLS
A modern and well constructed 36 unit complex consisting of 24 town homes 8 -one & two bedroom apartments and 8 commercial rentals . Top quality construction well maintained and landscaped .Municipal utilities . Red Hook DUTCHESS COUNTY is a lovely community property is in walking distance to shops and eateries . Three miles from Rhinebeck 100% occupies at all times . The town houses are all 3 bedroom 2 baths with full basements all of the apartments have washer dryers .Nice grounds and sidewalk system connects to village system. Rents are low and there is much upside complex is turn key needs nothing . Northern Dutchess county has a shortage of rentals and there is NO complex tat compares to this .a far as location and quality .Needs nothing turn key . Additional Information: HeatingFuel:Oil Above Ground,

33 Firehouse Lane, Red Hook

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