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$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
$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
$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
$775,000
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
$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 garage/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
$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
$219,000
1009852 MLS
High on the hillside, this untouched 12.78 acre haven presents peace, privacy, and room to dream. The future home site is tucked within mature forest, creating a quiet refuge with the possibility of beautiful seasonal vistas throughout the year. Minutes from downtown Pine Plains and close to the Taconic State Parkway, it strikes the perfect balance between retreat and convenience. A deeded right of way over an existing driveway ensures easy access to this secluded private land parcel.

Mount Ross Road, Pine Plains
$799,000
1008519 MLS
Commercial property with Multi-Use potential in Pine Plains, NY. This versatile commercial property boasts a variety of uses, making it of interest to investors, entrepreneurs and businesses alike. With two apartments, two office spaces, dedicated studio areas and a spacious workshop area with 5 bays with overhead doors. This property offers the perfect blend of residential and commercial functionality with potential for showrooms. Hardwood floors throughout and a new roof. Hard to find commercial property.

2773 Church Street, Pine Plains
$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
$975,000
1006565 MLS
The Ultimate Hudson Valley Lakefront Package: Waterfront Mainland Barn, Private Island Glamping Airbnb, Ease Side Lake Access Land & Endless Views! Welcome to a truly unprecedented real estate opportunity on the pristine waters of Twin Island Lake in beautiful Pine Plains, NY. This isn’t just a land listing; it is an extraordinary three-parcel package deal that blends rustic charm, income potential, and the kind of absolute tranquility that is rare to find. The Mainland Sanctuary (0.85 Acres) Step onto nearly an acre of gorgeous lakefront property, beautifully cleared all the way down to the water's edge. The centerpiece of the mainland is a solid, character-filled barn featuring a spacious loft that is just waiting for your vision. With electric already available, this loft could easily be transformed into a charming, creative living space, a writer's retreat, or the ultimate lakeside clubhouse. Outside, your private waterfront oasis is already set up for perfect summer days and cozy autumn nights. Launch a kayak from your floating dock, host a lakeside lunch at the picnic table, or unwind by the fire pit. The panoramic views across the water to the majestic Stissing Mountain rising in the background will quite literally take your breath away. Your Own Private Island Retreat As if the mainland weren't enough, this sale includes a literal dream feature: ownership of one of only two private islands on Twin Island Lake! Currently operating as a highly successful Airbnb, this island defines "glamping at its finest." It offers the ultimate off-grid luxury experience, fully equipped with: A cozy setup featuring a warming gas fireplace Covered kitchen area Raised Platform with Safari tent and bed An outdoor fire pit for star-gazing On-site toilet and a refreshing solar shower Whether you choose to keep running it as a lucrative short-term rental or reserve it entirely as your own secret hideaway, this island is a showstopper. Versatility & Nature at Your Doorstep To round out this incredible package, an additional 0.01-acre lake access property is included, offering even more versatility for layout and usage. This property is a haven for local wildlife. Spend your mornings sipping coffee while watching elegant swans, geese, and ducks glide across the glassy water, and spot turtles sunning themselves on the logs. It is a peaceful world entirely your own. The Location While you will feel a million miles away from the hustle and bustle, you are never isolated. This slice of paradise is located just 15 minutes from the vibrant, historic towns of Red Hook and Rhinebeck, giving you effortless access to fine dining, boutique shopping, farmers markets, and the Amtrak station. A short ride up the Taconic, this is a fast trip to escape the hectic pace of the NYC for the weekend or a summer of relaxation. Property Highlights: Total Package: 0.85-acre lakefront parcel + .25-acre Private Glamping Island + 0.01-acre lake access parcel. Structures: Barn with loft (electric available), floating dock, fire pit. Island Amenities: Turn-key Airbnb Glamping setup with gas fireplace, solar shower, and toilet. Views: Unobstructed lakefront and Stissing Mountain views. Don't miss out on one of the most unique waterfront offerings the Hudson Valley has to offer. Bring your dreams, your boat, and your sense of adventure!

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

68-78 Ridge Road, Clinton Corners
$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
$409,000
3 Beds ⋅ 2 Baths ⋅ 999870 MLS
More space and flexibility than you might expect! Set along a quiet country road in the Town of Gallatin, just outside Pine Plains, this 3-bedroom ranch offers approximately 1,860 square feet of living space with a finished lower level, providing plenty of room to spread out, work from home, entertain, or accommodate guests. The main level features hardwood floors, a full bathroom, three bedrooms, and a functional layout that’s ready to make your own. Downstairs, the finished lower level significantly expands the possibilities with additional living and dining areas, a full bathroom, and a second kitchen—known by the owners as the home’s “summer kitchen.” Whether used for recreation, guests, a home office, hobbies, or additional household space, this level gives the home versatility that’s increasingly hard to find. Outside, enjoy a covered patio perfect for relaxing, grilling, and outdoor dining, while the manageable property offers a peaceful country setting surrounded by the natural beauty of the Hudson Valley. Conveniently located near the hamlet of Pine Plains, with easy access to Millbrook, Millerton, Rhinebeck, Red Hook and surrounding communities. If you’ve been searching for a home that offers more usable space, a flexible floor plan, and country living at an approachable price point, 211 Sigler Road deserves a closer look. Come see how much this home has to offer.

211 Sigler Road, Pine Plains
$1,399,000
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
$575,000
3 Beds ⋅ 4 Baths ⋅ 997897 MLS
There are plenty of beautiful homes in the Hudson Valley. Far fewer offer a setting--and a lifestyle--like this. Set directly on the lake in one of the area's premier private communities, this architect-designed contemporary offers beautiful water views from nearly every room, abundant natural light, and something increasingly hard to find: the pleasures of owning a country home without many of the usual responsibilities that come with maintaining one. Designed by architect Steve Haas, the 3-bedroom, 3.5-bath home was created to embrace its waterfront setting. Walls of glass frame the lake throughout the main living spaces, while each bedroom features its own en suite bath, including a first-floor bedroom suite ideal for guests or convenient one-level living. At the heart of the home is a dramatic cathedral-ceiling living room with a wood-burning fireplace, expansive windows, and generous space for entertaining. The adjoining dining area and granite kitchen create an easy, open flow for everyday living and gatherings with friends, all with the lake as a backdrop. The large screened porch overlooking the water may quickly become the favorite room in the house. It's the perfect place for morning coffee, summer dinners, entertaining friends, or simply watching the lake change with the seasons. Just off the kitchen, a private courtyard provides another outdoor space for container gardening, a fire pit, or relaxing outdoors. What truly distinguishes this property is how easy it is to own and enjoy. Swim or kayak on the lake, play tennis or bike along the peaceful, tree-lined private roads or boardwalk. And with the beautifully maintained community pool just moments from the house, it feels almost like having your own pool--without the expense, maintenance, opening, closing, or day-to-day work of actually owning one. That same ease extends to the home itself. The association maintains the landscaping, snow removal, private roads, pool, tennis courts, and common areas, while also assuming responsibility for many exterior maintenance and replacement items that would ordinarily fall to the homeowner. The result is an unusually carefree approach to country living. Instead of spending weekends maintaining acreage, landscaping, clearing snow, caring for a pool, or worrying about exterior upkeep, you can simply arrive and enjoy the lake. For a weekend owner in particular, that's a meaningful difference. Offered fully furnished, the home is truly turnkey and ready to enjoy from day one. And while the setting feels like a genuine escape, it's remarkably accessible. Hudson and its Amtrak station are approximately 25 minutes away, while the Wassaic Metro-North station provides another convenient rail option to and from New York City. Rhinebeck, Pine Plains, the Berkshires, Tanglewood, the Taconic State Parkway, and some of the region's best restaurants, markets, and cultural destinations are all within easy reach. For buyers who want waterfront living without taking on the constant upkeep of a traditional country property, this offers a combination that's increasingly difficult to find: an exceptional lakefront setting, distinctive architecture, beautiful views, and a lifestyle designed to be enjoyed rather than maintained.

322 Arcadia Drive, Ancramdale
$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
$225,000
995573 MLS
Quietly tucked along a country road in the heart of Milan, this 13.66-acre parcel offers the kind of opportunity that’s increasingly rare in the Hudson Valley. Elevated terrain with rolling hills and rocky outcroppings provides the bones for a private retreat — with potential long-range views achievable with selective clearing. Zoned A5A, the property supports residential, agricultural, and hobby farm uses. With a 5-acre minimum lot size, the parcel also lends itself to subdivision into two conforming lots — a straightforward value-add opportunity for the right buyer. Rockwalls mark off the upper border. Electric is available on Cold Spring Road. Plenty of road frontage for a driveway in. Minutes from the Taconic State Parkway and close to the villages of Rhinebeck and Red Hook, yet completely private and unspoiled. Soft rolling hills on beautiful and quiet Cold Spring Road dotted with farmhouses and horse pastures just 90 miles to NYC. Whether you’re envisioning a custom home, a homestead, a small farm, or a smart land investment, this is a compelling canvas.

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

80 County Route 7, Pine Plains
$450,000
3 Beds ⋅ 2 Baths ⋅ 993638 MLS
Set on a nicely landscaped and private yard ideal for gardening with .65 acres total (an adjacent building parcel of .72 acre can be purchased for an additional amount). This inviting, well-maintained 3-bedroom, 2-bath ranch offers comfort and has a handicap-accessible interior. Features include a living room with a fireplace, lovely wood floors throughout, and a large basement perfect for a workshop, recreation room, or additional storage. The attached garage is accessible through a large sunroom/breezeway for three-season use. Located within walking distance, only minutes to the town beach on Stissing Lake and recreation area offering swimming, boating, and summer children’s camp. Also nearby is Stissing Mt. with hiking trails and Thompson Pond Bird Sanctuary. Pine Plains is a quaint village in Northern Dutchess County which is presently known for the Stissing Center for Arts and Culture and the Stissing House Restaurant. Move right in with no worries with a new roof and kitchen appliances, and central A/C for those hot summer days.

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

36 Market Lane, Clinton Corners
$1,495,000
3 Beds ⋅ 3 Baths ⋅ 987176 MLS
Experience this stunning sanctuary where rustic charm meets modern luxury on over 19 meticulously manicured acres of pure magic! This elevated 3-bedroom, 3-bath masterpiece captures your heart the moment you arrive, drawing you toward an expansive wood deck and a stunning screened-in gazebo with a built-in fire-pit - the ultimate "entertainment perch" for soaking in breathtaking, panoramic valley views. Inside, the home glows with natural light, featuring soaring vaulted ceilings, a gourmet chef’s kitchen with high-end appliances, and a primary suite that serves as a true retreat with its own stone fireplace and oversized closet. A newly reconfigured second bedroom with an adjacent study provides the perfect versatile workspace. The lower level adds even more flair with a sleek kitchenette, media room, a full bath and a new third bedroom. The equestrian facilities includes a 4-stall barn, arena, hay barn, and fabulous riding trails, catering to every horse lover's dream. 3-car heated garage and a powerful 45KW generator. This impeccably maintained estate isn't just a home, it is a move-in-ready lifestyle that is utterly magical. Minutes to the villages of Millerton and Pine Plains. 2 hours to NYC.

617 BEAN RIVER Road, Pine Plains
$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
$387,000
2 Beds ⋅ 2 Baths ⋅ 986400 MLS
Secluded 2BR/2BA RANCH w/2 large decks, all wood floors and wood siding + detached 2 car garage on 7+acres in Hamlet zone Easy subdivision into 4 and 3 acre lots. Also available as Compound with adjoining 8 acre parcel for $565.000 and additional 4 acre boha parcel for $689,000. Adjoining parcels can be purchased separately for . Great location between Pine Plains Village and Millerton on quiet road off Route 199. New well installed. Occupied month-to-month. Call for showing.

618 Bean River Road, Millerton
$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
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