luxury houses for sale Dutchess County, United States

PRICE ADJUSTMENT! Welcome to this exceptional 4-bedroom, 4-bath Colonial home offering 4,684 square feet of beautifully designed living space on over 2.5 private acres. Thoughtfully designed and impeccably maintained, this home offers exceptional flexibility with a finished walkout lower-level ideal for an in-law, au pair, or extended guest suite. A grand two-story foyer opens to a private home office, formal living and dining rooms, and a stunning gourmet eat-in kitchen featuring granite countertops, Thermador appliances, peninsula island, and custom walk-in pantry with reclaimed wood barn doors. The adjoining family room with double-sided gas fireplace flows into a bright all-season sunroom, and also features sliders to an expansive Trex bi-level deck. An updated powder room completes the main level. Upstairs, the spacious primary suite features a sitting area, walk-in closet, and luxurious ensuite bath with soaking Jacuzzi tub and separate shower. Three additional bedrooms, a full hall bath, and a convenient laundry room complete the second floor. The finished walkout lower level adds valuable living space with a private bedroom/guest room, full updated bath, recreation/living room, updated kitchenette, and sliding doors to a tranquil patio. Outside, enjoy a private backyard retreat with professionally landscaped grounds, mature trees, full fencing, a heated in-ground pool, pool house, pool shed, fire pit, and multiple entertaining areas. A rocking-chair front porch and three-car garage complete this remarkable property. Set on a peaceful cul-de-sac just minutes from the Taconic State Parkway, schools, shopping, and dining - and with the Dutchess County rail trail right across the street - this beautiful home offers the perfect blend of luxury, privacy, versatility, and convenience. Come make it yours today!

Twenty-One North Road was built in 1894. For nearly half a century, it was home to its most recent owner, who served for a time as mayor of Tivoli. Its five-color exterior palette, at once playful and understated, was one he chose and painted himself. The vines he tended still run along the wraparound porch, and a mowed path leads through the property to Stony Creek. The house sits on 2.21 acres in the village of Tivoli, with four bedrooms and one-and-a-half baths. Inside, the rooms are gracious without being grand, with floor-to-ceiling windows in the front parlor and two marble mantels, each with its own pattern and ornament. There are wide- and narrow-board floors, pocket doors, built-ins, and other details that reveal themselves as you move through the house. The property runs all the way to Stony Creek and continues onto the far bank, with a mowed path to take you there. At the water's edge, a small cascade runs over stone. Beside the house is a two-story outbuilding with electricity, a workshop/garage on the first floor and walk-up storage above. Its windows were salvaged from a 19th-century church. And then there's Tivoli. On Broadway, people walk for coffee, fresh bread, dinner, dessert in a cup or a cone, and late-night cocktails. Kaatsbaan Cultural Park is right in the village, Bard is just down the road, and Red Hook, Rhinebeck, Rhinecliff and Hudson are a short drive away. A 19th-century beauty, on more than two acres, with Stony Creek at the end of a path, in the coolest village around.

Perched atop 40.9 private acres, this exceptional custom-built estate offers unrivaled privacy and sweeping panoramic views of the Catskill Mountains. Blending timeless craftsmanship with modern luxury, this hilltop retreat embodies refined living in a breathtaking natural setting. Inside, antique teak flooring flows throughout the home, adding warmth and character to every space. The open floor plan features a gracious living room that opens to a library with a fireplace and a full bath, creating an inviting centerpiece for both relaxation and entertaining. At the heart of the home, the eat-in kitchen is both functional and striking, featuring a scullery and a distinctive modern Rumson fireplace. The kitchen opens effortlessly onto a stone terrace and pergola, offering a breathtaking setting for alfresco dining while overlooking beautifully landscaped gardens that evolve with the changing seasons. Adjacent, the formal dining room provides a refined space for hosting memorable gatherings. The lower level includes three bedrooms and four full baths, along with a music salon featuring expansive glass doors that open to a stone terrace with breathtaking panoramic views. Additional amenities include a wet bar, laundry room, and wine cellar, offering both convenience and luxury. A detached two-car garage complements the home's timeless architecture while adding everyday practicality. Experience the epitome of serenity, artistry, and mountain living in this extraordinary hilltop estate—where every sunset paints a masterpiece across the western sky.

A gracious Millbrook country house with remarkable scale, warmth and character, 663 Camby Road offers nearly 4,000 square feet of beautifully considered living space on 3.12 pastoral acres. Built in 1920 as a classic center-hall Colonial and thoughtfully expanded and reimagined by noted local architect Daniel Contelmo, the four-bedroom, three-bath residence pairs the symmetry and character of its original architecture with the soul and texture of a classic farmhouse, dramatic light-filled spaces and a distinctly stylish point of view. The extraordinary great room is the centerpiece of the house: soaring vaulted ceilings crossed by antique beams, wide-plank wood floors, a substantial stone fireplace and a dramatic wall of floor-to-ceiling bookshelves create a space that feels both impressive and deeply comfortable. French doors open to the grounds, while the adjoining dining room and kitchen flow naturally together for everyday living and entertaining. The kitchen features cabinetry in a subtle green hue, complemented by white subway tile and new white quartz countertops with delicate speckling. A generous center island, three pantry closets and stainless-steel appliances complete the space. An exceptionally spacious mudroom, with polished concrete floors and abundant hooks and storage for coats, boots and bags, provides a handsome and highly practical everyday entrance to the house. The expansive first floor also includes a second living room, full bath, newly renovated laundry room, flexible office or studio, and a private bedroom with an en-suite full bath. Upstairs are three spacious bedrooms, including a generous primary bedroom with a large walk-in closet, along with a full bath and loft. The grounds are equally inviting. A circular drive introduces the property, framed by mature trees, established landscaping and broad lawn. A flagstone patio creates a natural setting for outdoor dining and entertaining, while walking trails meander through the property to a secluded meadow beyond the main grounds. A peaceful Zen garden provides another private outdoor retreat, while a flexible recreation court currently accommodates both basketball and pickleball. A substantial fenced area, attached garage and charming garden room well suited to potting, storage or creative use complete the property. Recent improvements include new white quartz kitchen countertops and updated appliances, a completely renovated laundry room, a new well pump, new chimney liner and cap, updated front entry and porch, fencing, and septic-access improvements. Set along a scenic country road amid farms, equestrian properties and conserved countryside, 663 Camby Road feels private and distinctly rural while remaining approximately five miles from the Village of Millbrook, convenient to Metro-North and about 90 minutes from New York City.

Fallkill, a late 18th-century, thoughtfully renovated farmhouse, sits on six magical acres with stone walls, an artist studio, an antique barn, and a beautiful cedar sauna tucked in the woods, all overlooking idyllic rolling meadows, a meandering creek, and forest. The setting is quintessential Hudson Valley countryside, with the house sitting on one of the prettiest roads in Dutchess County, and the home has been artfully updated, with abundant historic charm intact. The Home: The home perfectly balances moodier, historic interiors with bright, modern spaces. The main level has a new addition with enormous windows, which is home to an open-plan kitchen outfitted with top-quality appliances and a sun-drenched dining area. Moving into the original circa 1700s part of the house, the living room centers around the beautiful fireplace and is framed by wood beams and the most exquisite original wood floors. A full bathroom completes the first floor, with the three bedrooms and another full bath on the second floor. The finished basement is expansive, with a laundry/utility room, office, and extensive storage space. Every tile, piece of hardware, lighting, and finishings throughout the home have been hand-picked for their quality, longevity, and unique style. The Grounds: The exterior feels very private, with a split-rail fence running along the property line and exceptionally charming landscaping. A stone patio with a gas outdoor fireplace and an outdoor shower blend in perfectly with the exterior. A stone path through a meadow leads to the artist studio, bathed in light and tucked away from the main house. Amidst the woods is a 10-person Cedar & Stone sauna with a changing room and deck. The picture windows in both the sauna and the artist studio look out onto exceptionally verdant landscapes. A historic barn could easily become a future workshop, and restored stone walls are peppered throughout the property. The Surroundings: Fallkill sits amidst a peaceful neighborhood, where weekends can be enjoyed visiting Mills Mansion and its grounds, dropping by the farmer's market in Rhinebeck or the MPO farmstand, grabbing lunch at Golden Russet, and taking long walks and bike rides near the property. The home is less than 15 minutes from Rhinebeck, under 20 minutes from Rhinecliff Amtrak Station, and an hour and a half from New York City.

Farm Nord is a meticulously restored country estate, originally established in the 1700s as a dairy farm by the renowned Taber family of Rhode Island. The Tabers were stewards of the estate for five generations and two centuries, with only a few families since carrying on its legacy. The property’s idyllic 12 acres are peppered with endless stone walls, several-hundred-year-old trees, and rolling meadows. The seat of the estate, a traditional gentleman’s farmhouse, lies at the end of a long gravel driveway lined with historic sugar maples on both sides. The original barn has been renovated, with a charming cedar-shake roof and an attached fenced kitchen garden, and a sweet cottage nestled into the hills above the house has an interior wood-burning sauna and wellness space. The nearly 300 year old, three bedroom, three bath home has been thoughtfully preserved, without compromising the authenticity of the original details, including the wide board wood floors, long beams, and five wood-burning fireplaces. The kitchen was created in tandem with a masterful local craftsman and woodworker, featuring DeVOL fixtures, La Cornue sinks, a dual Wolf range, top-quality appliances, aged brass hardware, and entirely custom cabinetry. The kitchen connects to a light-filled family breakfast nook that overlooks, through walls of French doors, the property’s outdoor dining terrace and picturesque gardens. Off the kitchen, on one side, is the formal living room with a wood-burning stone fireplace, and on the other is the light-filled dining room with the original cooking hearth and a butler’s pantry. A wallpapered full bath and a quintessential mudroom finish the first floor. Upstairs, the family room has tall, vaulted ceilings with wood beams, a fireplace, built-in window benches with storage, and some of the prettiest views of the property from its tall windows and French doors. Off the family room is a richly colored office with custom cabinetry, paneled walls, and a skylight that streams in light throughout the day. The primary suite is tucked away in its own wing of the house, and has a hearth fireplace, a large walk-in closet with beautiful cabinets and extensive storage, and a tastefully appointed bathroom. The remaining two bedrooms look out over the meadows surrounding the home, and share the third bath with a claw-foot soaking tub. Farm Nord is bordered by hundreds of acres of conserved land, making for an abundantly peaceful setting. The original barn, fully restored, has a workshop/studio space, gym, and plenty of additional storage. There is an established herb garden with installed irrigation next to the barn and tall fencing. A small building nestled atop the property’s hills has been converted into a wood-burning sauna. Trails meander through the property’s twelve acres, and a truly incredible number of stone walls line the lush meadows. Farm Nord is conveniently located less than 90 minutes from New York City and just 10 minutes from the Metro North station in the quaint village of Pawling. The area is filled with bucolic farms, rolling hills, and stretches of the Appalachian Trail, making it an excellent area for anyone who loves hiking, wild swimming, and biking.

The Rhinecliff House begins with its setting, just steps from the Rhinecliff train station and a short drive into the Village of Rhinebeck, where mornings can start with a walk for coffee and end with a seamless trip back from the city. It is a place where Hudson Valley calm and everyday access to NYC naturally meet. Inside, the home unfolds with a sense of ease and possibility. Currently arranged as a two family residence, it offers flexibility that adapts to the way you want to live. The first floor moves comfortably from a formal dining room to a welcoming family room, with two bedrooms, a mudroom, and a rear porch that opens to a fenced yard, a space equally suited for quiet living or generating rental income. Upstairs, three additional bedrooms create room for extended stays, multi generational living, or a simple investment setup. Whether kept as is or thoughtfully reimagined into a single family home, the layout invites your vision. Set on approximately 0.84 acres, the property feels unexpectedly expansive for such a convenient location, made even more compelling by the inclusion of the adjacent parcel formerly known as 410 Rhinecliff Road. Together, they create a broader sense of space and possibility that is rarely found this close to the train and village. Recent upgrades, including a brand new HVAC system and a new roof, bring a sense of ease and reliability. Beyond the main house, a detached garage, positioned on the former 410 parcel and also with a new roof, offers another chapter waiting to be written, whether as a studio, workspace, or creative retreat, with the added flexibility that comes from its placement on the additional lot. With nearly an acre of land, there is space here to grow, to garden, to gather, or to shape something more. The Rhinecliff House is not just a home, but an opportunity to create a lifestyle defined by flexibility, scale, and connection to one of the Hudson Valley’s most sought after settings. And though you're not on the water, the river breeze reminds you it's never far.

Tucked gracefully in a private, tree-lined setting, this timeless New England-inspired residence offers the rare combination of classic architecture, exceptional craftsmanship, and effortless everyday living. Sunlight pours in through expansive windows, framing views of mature trees and a rolling lawn in every season. Every detail reflects quality—from the substantial millwork and rich materials to the thoughtful balance of formal and casual spaces. The expansive living room is both inviting and refined. At the heart of the home, the spacious kitchen is designed for both everyday living and effortless entertaining. A generous center island provides abundant workspace, complemented by ample cabinetry and a well-appointed layout. Three generously proportioned bedrooms provide peaceful retreats, each filled with natural light and tranquil views of the surrounding landscape. Outdoors, the property transforms into a private retreat. A freeform pool anchors the backyard, surrounded by natural stone terraces and layered gardens that blend seamlessly into the landscape. Whether gathering around the fire pit or spending quiet afternoons poolside, the setting feels peaceful and secluded. Beautifully maintained and thoughtfully designed, this is a home that lives as well as it looks: elegant without feeling formal, spacious without excess, and timeless in every sense.

Step back in time and bring your vision to this classic 1870s Colonial, featuring original details throughout, perfectly situated on a lovely one + acre lot on a quiet country road. Flanked by mature pines and Flowering Hibiscus. The property offers a serene setting while being conveniently located near the charming village of Millbrook, NY. A unique opportunity for those looking to restore a piece of history and create a dream home in an unbeatable location. The main residence features three bedrooms and 1.5 baths, providing a solid foundation for renovation and modernization. Whether you're looking to preserve original character or modernize the layout, the bones of this home offer endless possibilities. In addition to the main residence, there is a guest house with two separate living areas and a garage/workshop space. Each living area has 2 bedrooms and a full bath. Perfect for extended family or a home office, this additional space adds significant value and flexibility. Set in a coveted location that combines privacy with accessibility, this property is ready for its next chapter. Bring your contractor and your creative ideas this house is just waiting to be restored to her formal glory! Close to multiple sporting clubs, like Orvis Sandanona, Mashomack Polo and Tamarack preserve. 90 Minutes to NYC. and 15 minutes to Wassaic train station.

Set on 3.2 picturesque acres in Pawling NY this meticulously maintained 1960s Colonial has been lovingly built and owned by the same family for many years, and by that family on this land for generations before that. It's a rare offering: a true multi-generational retreat with room to grow. The four-bedroom, two-and-a-half-bath home offers timeless original character throughout, with hardwood floors beneath the carpeting, protected for decades. Features an attached two-car garage and a pull-down attic for extra storage. Sunlight pours through nearly every window, with valley and mountain views on two sides and a view of your private pond on the other. Watch the sunrise and the sunset settle over your own grounds. This property offers sweeping, ever-changing views in every direction all year round. It simply can't be beat. Downstairs, a fantastic finished lower level adding even more living space: a retro-style bar complete with running water, a vintage refrigerator, and a two-burner electric stove, plus a full bathroom, an office, an additional bonus room and a pantry! Beyond the main house, a versatile outbuilding adding exceptional value as it houses an additional one-car garage, storage room, plus a dedicated ~700-square-foot workshop space, currently used for handcrafted Amish furniture-making; it is an ideal spot for a hobbyist, craftsperson, or anyone in need of serious workshop or studio space. And there's more…this offering includes the opportunity to create a true family compound. Two additional buildable parcels are available from the same family. MLS 1037478 and MLS 1037481. Each zoned for a single-family home. Build for extended family, create a private enclave, or invest in future value, all connected to this storied piece of land. You will be surprised to learn that this home is just a few minute ride to the Pawling MetroNorth station to NYC, and the center of town, home to farmers markets, fine dining, coffee shops and boutiques.

The History: The wonderfully characterful Hammertown was established in 1774, in a small hamlet of millworkers, farmers, and blacksmiths, amidst the lush pastoral landscapes surrounding what would become the town of Pine Plains, New York. The home and its grounds were occupied by only three families across 250 years, each family slowly developing the property to include, in addition to the sprawling main house, beautiful, sweeping trees and gardens, stone walls, a two-hundred-year-old barn that has housed many an ambitious project, and a sweet guest house nestled at the entrance of the land. The Main House: The seat of the property is a traditional colonial farmhouse, tastefully renovated and beautifully envisioned for the current era - while still respecting the home's history as it passed through a quarter of a millennium. Exquisite millwork lines every wall in the home, no less than five fireplaces are peppered throughout, and we mustn't forget the beautiful, wide-plank wood floors. On the ground floor, you'll find a large boot room with plenty of storage, a formal dining room, a cozy living room, a wallpapered powder, and the beating heart of the home - the monumental kitchen; a light-filled and dreamy space perfect for entertaining. The second floor has two large bedroom suites with a full bath each, three additional bedrooms, and another full bath. Each bedroom has a subtle but charming color palette, more extraordinary woodwork, and two of the bedrooms have fireplaces. The proportions of the rooms and the layout are well suited to a large family or those with frequent guests, with the two en suites each occupying their own corner of the house, and the three bedrooms and last bathroom in their own wing. The Grounds: Outside, the farmhouse has two 'faces' and two beautiful porches. Additionally, a large dining terrace bordered by stone walls sits conveniently off the kitchen. Strolling away from the main house, you'll find a wrought-iron greenhouse structure and a French parterre garden planted with herbs, lavender, and flowers. The Barn: The Hammertown barn, built in the early 1800s by the founding family of the property, has lived many exciting lives - from being home to elephants from the Barnum Bailey Circus in the early 1900s to its most recent iteration as the main outpost of a beloved furnishings and antiques brand. The barn's soaring beams and incredible staircase welcome you into the structure, where multiple rooms serve various purposes - including plenty of living space (the perfect place for a home theater), open, sprawling areas with soaring ceilings ideal for hosting large groups, and an abundance of utility, office, and storage space. The barn is fully serviced with electric, air conditioning and heat, and plumbing (including a bathroom). The Guest House: The two-bedroom, two-bath guest cottage was built to elegantly blend with the property's historic character and features multiple fireplaces and detailed millwork. The double-height great room's arched window floods the house with warm light, and French doors lead to the cottage's sweet outdoor terrace. The Surroundings Hammertown is just minutes from Pine Plains, less than fifteen minutes from Millerton and the Connecticut border, and two hours from New York City. The area is defined by some of the most beautiful country landscapes in the region, and is full of hiking trails, thriving local farms, and wonderful small towns and communities. As a marvelously well-serviced compound, Hammertown has incredible potential for those who also wish to explore live-work opportunities, having been home to multiple tasteful commercial ventures and events over the past several decades.

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.

In the heart of Millerton, where charm, history, and community come together, this distinctive 1870 residence offers approximately 2,888 square feet of warm and gracious living space. Thoughtfully expanded in 2008, the home features four bedrooms, two full baths, and a conveniently located half bathroom on the first floor, blending original character with spaces designed for modern living. The addition introduces a beautifully scaled, light-filled living room with hardwood floors, multiple windows, and a wood-burning brick fireplace. Generous yet welcoming, it is a natural gathering place for quiet evenings at home, time with family and friends, and effortless entertaining. The primary bedroom is a retreat of its own, distinguished by high ceilings, beautiful proportions, and a second wood-burning brick fireplace. Three additional bedrooms provide space for family, guests, a home office, or creative pursuits, while the finished basement adds valuable extra living space for recreation, work, or relaxation. Outside, a covered front porch welcomes you home, while the rear deck, private backyard, and bluestone patio with a third brick fireplace create inviting spaces for morning coffee, outdoor dining, and relaxed evenings beneath the trees. Millerton’s cafés, restaurants, shops, The Moviehouse, village park, and the Harlem Valley Rail Trail are all within walking distance. Rich in character and thoughtfully expanded, this special home offers historic beauty, modern comfort, and the ease of life in a close-knit village community.

Among Dalton Farm's carriage house residences, this end-unit townhouse stands apart for its generous proportions and distinctive floor plan. First-floor living meets an expansive loft and a fully finished walkout lower level — three distinct levels, each with its own purpose, adding up to a home that expands and contracts with how you're using it that day. The two-story living room fills the main level with light. Open to the adjoining dining room and kitchen, the spaces feel connected while holding onto their own comfortable scale. A spacious primary suite and second bedroom with an adjacent full bath complete the main level, along with a new washer and dryer set in the transitional hallway leading to the lower level. Overlooking the living room, the loft is at once a library, home office, and gathering space. It's where work gets done, books are enjoyed, board games are played, and festive meals have room to grow. A full bath and walk-in closet give the loft the flexibility to serve as overflow guest space. The walkout lower level is fully finished, adding approximately 1,350 square feet with two bedrooms, a full bath, a mirrored flex space for workouts or yoga, a media lounge enhanced with acoustic wall panels, and a separate area for the billiards table. With more than 3,300 square feet of finished living space, the home offers four bedrooms, four full baths, and exceptional flexibility across three finished levels. The covered front porch welcomes quiet mornings, while the rear deck extends the home's living spaces outdoors for dining, entertaining, or simply enjoying the view. Below, the walkout patio provides additional outdoor space just steps from the recreation room. The landscape has been thoughtfully designed to frame — rather than compete with — the protected wetland meadow beyond, its tall grasses shifting from green to gold through the season, backed by a wooded hillside that keeps the view feeling protected and open. The current owners have maintained the home with real discipline: a new roof, mechanical systems serviced on schedule, California Closets throughout, and a two-car garage outfitted with ceiling-mounted storage and not an inch of wasted space — the kind of thoroughness that pays off long after moving day. Dalton Farm is more than a well-respected HOA, it's a place with real history and an active, connected community. Set on the former estate of Franklin Roosevelt Jr., the neighborhood's clubhouse, the 200-year-old Roosevelt House, anchors a self-governing community known for its stability and engaged homeowners. Residents enjoy the swimming pool, tennis courts, walking trails, and equestrian center, along with a full calendar of community life—from book clubs to seasonal gatherings, all within easy reach of the Taconic State Parkway, Metro-North, and the Hudson Valley's villages, restaurants, and everyday conveniences.

Experience sophisticated country living at this completely reimagined, modernized Cape Cod in Salt Point, NY. Nestled on a quiet, scenic road within a landscape of manicured equestrian estates and bucolic farms, this 5-acre sanctuary offers absolute privacy with no immediate neighbors—only the peaceful sound of birds chirping in the meadow. Every detail has been meticulously curated, ensuring that all the heavy lifting has been expertly completed for the next owner to simply unpack and enjoy. The home features brand-new Hardie Board siding and all-new mechanical systems, including an upgraded water system and enhanced electrical with a whole-house generator for peace of mind. Outside, your private oasis awaits: a heated saltwater pool, a relaxing hot tub, a newly built detached two-car garage, and a versatile storage shed perfect for a clubhouse. A pristine Airstream is also available for purchase, offering a unique opportunity for guest accommodation or creative space. While offering total seclusion, this retreat is incredibly well-connected. You are just 90 minutes from New York City and a short 15-minute drive to the vibrant dining and culture of Rhinebeck. With easy access to Amtrak in Rhinecliff and Poughkeepsie, and Metro-North in Wassaic, you can enjoy the best of both worlds: the tranquility of the Hudson Valley and the convenience of city accessibility.

Milan Hall Farm circa 1750 Truly exceptional. Completely private. Set across 87 acres of open field and quiet forest, Milan Hall Farm unfolds as a rare Hudson Valley offering—where land, history, and thoughtful stewardship meet. A winding stream and natural waterfall trace the landscape, alongside a private 1.3 mile walking trail through the woods, all bordered by enduring stone walls that speak to the property’s agricultural past. Protected under conservation easement with the Winnakee Land Trust and New York State forestry program, the land offers both privacy and permanence. The farmhouse, dating to the mid-18th century, has been carefully expanded to accommodate modern living while honoring its origins. Three bedrooms, each with en- suite baths, are complemented by a light-filled conservatory, a quiet library, and multiple gathering spaces anchored by wood-burning stoves. A broad porch overlooks the gardens, while bluestone patios extend living outdoors. The grounds are meticulous—layered gardens, mature plantings, and curated outdoor moments throughout. A separate guest cottage with its own wood-burning stove provides space for extended stays or private retreat. The 1853 post-and-beam barn, equipped with electric and water, offers flexibility as a studio, workshop, or future living space. Additional outbuildings, including a two-car garage, support both function and form. Modern systems—solar power, central air, and a whole-house generator—bring ease and efficiency. Minutes to Rhinebeck Village, Amtrak, and some of the region’s most sought-after dining and shops, yet entirely removed from it all.

Nestled within a mature forest canopy on 1.44 private acres, this custom-built residence draws inspiration from the enduring principles of Craftsman design while embracing a distinctly modern sensibility. Perched on a gentle rise above a quiet cul-de-sac and surrounded by mature woodland, the home announces itself with navy siding, low-profile rooflines, broad cedar-clad overhangs, and a cedar-ceilinged covered porch supported by substantial timber posts. Craftsman-inspired windows with geometric grille detailing frame woodland views while filling the interiors with natural light. Designed to celebrate both connection and flow, the floor plan creates sight lines from the eight-foot entry doors through the main living spaces to twin sets of French doors framing the trees beyond. Expansive windows throughout blur the distinction between indoors and out, bringing the surrounding landscape into nearly every room. Hardwood floors extend throughout the main level, unifying the living room, dining area, and kitchen into one generous, light-filled expanse. A sleek fireplace with a dark slate surround anchors the living room, while windows on every exposure draw in natural light and views of the surrounding landscape. At the heart of the home, the kitchen features rich custom cabinetry, beautifully patterned natural stone countertops, stainless steel appliances, a generous center island, and a walk-in pantry. An array of oversized windows above the sink frames peaceful views and transforms everyday tasks into something far more enjoyable. The adjacent dining area opens directly to the rear deck overlooking the private backyard, creating an effortless transition for indoor-outdoor living and entertaining. Beyond, the backyard offers level lawn, mature trees, a fire pit for evenings outdoors, and exceptional privacy. A generously sized, private first-floor office offers an ideal setting for working from home. Nearby, a well-appointed mudroom with built-in bench and coat hooks provides convenient access from the attached two-car garage. Upstairs, the primary suite serves as a peaceful retreat, complete with a private sitting room, fireplace, generous walk-in closets, and a beautifully appointed ensuite bath. A soaking tub set beneath a row of clerestory windows and a large glass-enclosed shower with rain head, bench, and pebble floor create a spa-like atmosphere. Two secondary bedrooms share a well-appointed full bath -- one of which currently functions as an upstairs office and media room -- while a fourth bedroom enjoys the privacy of its own ensuite. A full unfinished basement provides exceptional storage and meaningful potential for future expansion. Built in 2024 by Rieger Homes, 45 Cliffdale Court offers a compelling combination of architectural character, quality construction, and privacy within one of the Town of Poughkeepsie's most desirable enclaves of custom homes. From this peaceful setting, residents enjoy easy access to Vassar College, the Culinary Institute of America, the Walkway Over the Hudson, and a city increasingly recognized for its investment, revitalization, and expanding cultural and hospitality offerings.

Western-facing sunset views over the Catskill Mountains—the coveted vistas everyone is looking for. Set on 12 beautiful, private acres complete with a tranquil pond, this gorgeous post-and-beam home is expertly designed to take full advantage of its spectacular surroundings. Tucked away on serene Charlie Hill Road, the property immediately welcomes you with sweeping sights of the rolling meadow and water. The moment you step inside, you are struck by the dramatic, two-story living room, where a magnificent wall of windows and French doors perfectly frame the mountain vistas. A massive floor-to-ceiling chimney with a double-sided fireplace beautifully divides the living space from the kitchen and dining area, creating an atmosphere that is both open and incredibly cozy. For single-level convenience, the spacious first-floor primary suite offers its own set of French doors, opening directly to the porch and those same incredible views. The home offers plenty of space for guests and relaxation across its three levels. The lower walk-out level features two large bedroom suites and a comfortable family room complete with a second fireplace and a wet bar, making it an ideal space for entertaining. Upstairs, you will find an additional bedroom with a half-bath, a dedicated home office, and access to the home's unique crow's nest. Featuring a cozy window seat and panoramic sights, it is the ultimate private retreat to escape with a good book and watch the sun go down. While the property feels like a completely private sanctuary, it is incredibly accessible to the best of the region. Located less than ten minutes away is the center of Millerton, New York, celebrated for its vibrant atmosphere, antique shops, local eateries, and The Moviehouse. Outdoor enthusiasts will love the immediate access to the Harlem Valley Rail Trail, offering 26 miles of paved trails from Wassaic to Hillsdale for walking, running, biking, and winter cross-country skiing. With the Metro-North train less than 20 minutes away for a seamless commute to Manhattan, and close proximity to Hudson, Northwest Connecticut, and the Southern Berkshires, this location is truly unmatched.

Early house with charming changes. All updated. Overlooking stream and pond. On 13+ acres. Meadows and woodland walks. Charming old apple orchard. 3 bedrooms, primary bedroom on ground floor. 2 baths. Fireplace in living room. Swimming pool.

WhistleWood Farm A rare multi-use estate set on just under 40 acres in the heart of Rhinebeck, NY. Currently operating as a successful bed-and-breakfast, event venue, and horse boarding facility, WhistleWood Farm offers exceptional flexibility for both residential and commercial buyers seeking a true Hudson Valley destination property. Comprised of three parcels totaling nearly 40 acres, the property is equally suited as a private compound, gentleman’s farm, equestrian retreat, boutique hospitality venture, or wellness-focused escape. Existing hospitality and equestrian infrastructure provide a strong foundation for continued or expanded use. The main residence spans approximately 4,500 square feet and features 5 bedrooms, 5 full baths, and 2 kitchens—offering remarkable flexibility for private living, guest accommodations, or hospitality operations. Complementing the main house is an beautifully appointed 1,500-square-foot carriage house with three bedrooms and three baths, rich in character and perfectly suited for guests, extended stays, or expanded event and hospitality use. Walking trails through the woods create a rare sense of privacy and connection to the landscape just moments from the heart of Rhinebeck Village—with its celebrated dining, farm-to-table restaurants, boutiques, and nearby Amtrak access. For the tennis enthusiast, premier tennis facilities conveniently located next door further enhance the property’s lifestyle appeal. Open meadows, mature trees, and a coveted Village-adjacent setting make WhistleWood Farm a truly rare offering—equally compelling as a private estate, hospitality investment, or legacy property in the Hudson Valley. Additional features include solar power, further enhancing the property’s efficiency and long-term sustainability.

A classic, modern farmhouse on five acres with a pond, perennial gardens, and a beautiful, sprawling backyard all on a dead end road. Newly constructed in 2022, the immaculate 4,000+ square foot home is perfectly executed. The interiors feel luxurious with wideboard white oak floors throughout and a vaulted 17ft ceiling in the main, open living space. There is a gas fireplace anchoring the room and the open kitchen features an extra large Liebherr refrigerator, a double oven and coffee station. There is a spacious pantry with additional storage and a wine fridge. You’ll find a home office and formal dining room. The primary suite is on the main floor, large with sliding doors out to a private balcony and hot tub. The bath is ensuite with double vanities, radiant heated floors and a soaking tub and there are two walk-in closets. You'll find two additional bedrooms on the main level, both well sized and connected by a jack-and-jill bath. Upstairs is a large sitting area currently used as a play room, an additional bedroom and a full bath, as well as a flex space which the current owners use as sleeping quarters. The 2,500+ square foot basement has fabulous high ceilings making it super usable, it’s set up as a home gym. A large screened in porch overlooks the backyard and the woods beyond, and there are raised garden beds ready for when the weather turns. An irrigation system has been installed which keep the gardens very low maintenance. There is an attached two car garage and the home sits in a neighborhood setting amongst other homes of a cohesive aesthetic. 11 Crimson Hill is a wonderful turnkey option just minutes to Rhinebeck village and Amtrak. Located in the Rhinebeck School District it is perfect for year round or weekend living.

Meticulously Maintained ELEVATED 3 BEDROOM/3 BATH Log Cabin-Style home and horse barns on 19+ acres with BREATHTAKING views. Set off a quiet country road, this stunning setting with impeccably manicured grounds captures one's attention upon arrival. One is immediately drawn to the expansive wood deck complete with built-in grill and impressive screened-in gazebo with fire-pit. This is unquestionably the perfect entertainment perch which captures the beautiful long views of the valley and hillsides. Fabulous open floor plan inside, with vaulted ceilings in living room with stone fireplace, large dining area, and light and bright gourmet eat-in kitchen with high-end appliances. Primary bedroom also has vaulted ceilings, stone fireplace, and large walk-in closet leading to primary bath. Study off of Primary Bedroom. Second bedroom on main level has been recently reconfigured. Another great entertaining space is located downstairs including a large area perfect for games, exercise or media room with kitchenette. A THIRD bedroom was recently created near a recently renovated full bath. 3 car heated garage with massive storage space upstairs. 45KW generator. For the horse enthusiast, the property also includes a hay barn, paddock, 4 stall horse barn & tack room, equipment sheds and arena. Great riding trails abound. This exceptional property is move-in ready and utterly magical.

Welcome to 6 Conifer Court—A Modern Farmhouse Masterpiece in Tamarack Heights! Experience luxury living at its finest at the end of a peaceful cul-de-sac in one of Poughkeepsie's most sought-after neighborhoods. Built in 2023, this spectacular 5,250 sq ft home sits on nearly 3 acres of beautifully landscaped grounds, offering privacy and tranquility just minutes from Eastdale Village, Adams Fairacre Farms, and Starbucks. Step inside to soaring high ceilings with stunning exposed wood beams and a dramatic two-story stone fireplace that anchors the sun-filled open-concept living space. The chef's kitchen is a true showpiece, featuring a full Thor Kitchen appliance suite, a spacious island, walk-in pantry, and a dedicated chef's pantry with prep sink. The butler's pantry includes an additional Thor wall oven, and the wine refrigerator is also Thor—creating a seamless, high-end culinary experience perfect for entertaining or everyday gourmet cooking. A dry bar adds even more convenience and style. The first-floor suite provides comfort and flexibility, while the luxurious owner's retreat upstairs boasts a spa-like bath and walk-in closet. The massive basement with 14-foot ceilings is a blank canvas—ready to become your dream gym, home theater, studio, or provide endless storage. Enjoy outdoor living on expansive decks, a screened porch, and a patio, all surrounded by lush greenery. Additional highlights include a state-of-the-art surveillance security system, a 3-car garage, central air, propane heating, and abundant storage throughout. Some furniture included in the sale. Schedule your private showing today and experience the lifestyle you've been dreaming of at 6 Conifer Court.