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Imagine never tiring of your own backyard. Nestled on one of the prettiest roads in Hillsdale, this beautiful single-level home is a front-row seat to rolling meadows, distant hills, and the quiet magic of the changing seasons. This sun-drenched, single-level home offers an effortless lifestyle framed by stunning, panoramic views. Inside, an expansive open floor plan invites the outside in. The thoughtfully appointed, updated kitchen flows seamlessly into a generous living area anchored by custom built-ins and a cozy wood-burning fireplace. Wall-to-wall windows grace the formal dining room, ensuring every meal is accompanied by breathtaking scenery. Both the living and dining rooms offer direct access to a sprawling rear deck, perfect for entertaining. A tranquil sun-room provides a versatile space, ideal for a home office or a quiet retreat. Down a private hall, the sleeping wing awaits. The primary suite is a true haven, featuring a second fireplace, a charming window seat for reading, a large walk-in closet, and an en-suite bath. Two additional well-proportioned bedrooms with ample closet space share a pristine hall bathroom. A generous two-car attached garage and a full basement offer abundant storage and convenience right off the main entry.Outside, the 8.3-acre grounds are a serene blend of manicured lawn, wild meadow, and mature plantings. The location is truly stellar: less than five minutes to Catamount Mountain Resort for year-round adventure, and just moments from the heart of Hillsdale, home to excellent dining like the historic Roe Jan Brewing Co. With Great Barrington, MA, just 20 minutes away and Hudson, NY, a mere 30-minute drive, this exceptional property perfectly balances pastoral tranquility with unbeatable cultural access.
…By William Pitt Sotheby's International Realty
A modern country home inspired by the farmhouses of the Hudson Valley. Taconic Creek Road is tucked away amongst rolling hills and large surrounding parcels, on a beautiful dead end road with just a few lovely houses. The palette is restrained but luxurious with a thoughtful layout and custom design details. Spanning 2,100 square feet, you’ll find lime washed walls with stunning depth of color, custom millwork and wideboard wood flooring that adds warmth to the space. The main living area is anchored by the open kitchen, with Tundra Gray marble counters, an English farmhouse sink, custom inset cabinetry and paneled appliances. A deVOL pendant hangs over the kitchen table. The sitting area is lined with custom built bookshelves and there are large, deep windows lining the room. They face out into the garden, and french doors at the center take you onto the patio. There is storage and a built in bench at the entry for your boots and bags, and a lovely bath on the main level with Noguchi pendant lights. Upstairs, a light filled sitting room walks out to a screened in porch, and there are three bedrooms spread out across the floor. The primary suite is large with a stunning picture window, an office/walk-in closet and a gorgeous bathroom. You’ll find a walk-in-shower and soaking tub with views of the surrounding treetops. Two other bedrooms share the third bathroom off the hall. There is an extensive list of upgrades that includes a new roof, HVAC and septic, and the current owners buried the electrical lines to the house. A large pool is surrounded by lilacs and hedges, private and peaceful, and there is a garage for parking. Taconic Creek Road offers a rare level of calm and sophistication just 15m to Hudson and Amtrak and under 2.5h north of NYC.
…By Four Seasons Sotheby's International Realty
Discover a truly singular retreat: a 1,700-square-foot, octagonal contemporary barn residence designed and built by a noted architectural designer. Set deep within more than four acres of pristine woodlands on one of Columbia County’s most coveted roads, this home offers the rare combination of modern architecture, privacy, and effortless living. Expansive pivoting picture windows invite a constant play of light throughout the interior and frame the surrounding landscape as living art. Inside, the soaring cupola-topped ceiling and radiant-heated polished-concrete floors create a calming, loft-like atmosphere, anchored by a dramatic floating propane fireplace. The designer kitchen integrates seamlessly into the open living and dining spaces, making the home equally suited for quiet evenings or stylish entertaining. Two airy, loft-style sleeping areas, and two sleek glass-and-steel baths complete the thoughtfully curated layout. Every element of the home blends sophistication with simplicity—ideal for a buyer who values design, nature, and ease. Tucked away yet minutes from Hillsdale, Hudson, Egremont, and Great Barrington, the location offers instant access to the region’s best culture, dining, and outdoor recreation. With NYC and Boston a little over 2 hours away, this property is the perfect full-time escape or effortlessly luxurious weekend base. A rare architectural and design statement, this steel-and-glass modern barn redefines country living for the buyer seeking something truly unique. Plans are available for a one or two bedroom addition.
…By Four Seasons Sotheby's International Realty
Imagine never tiring of your own backyard. Nestled on one of the prettiest roads in Hillsdale, this beautiful single-level home is a front-row seat to rolling meadows, distant hills, and the quiet magic of the changing seasons. This sun-drenched, single-level home offers an effortless lifestyle framed by stunning, panoramic views. Inside, an expansive open floor plan invites the outside in. The thoughtfully appointed, updated kitchen flows seamlessly into a generous living area anchored by custom built-ins and a cozy wood-burning fireplace. Wall-to-wall windows grace the formal dining room, ensuring every meal is accompanied by breathtaking scenery. Both the living and dining rooms offer direct access to a sprawling rear deck, perfect for entertaining. A tranquil sun-room provides a versatile space, ideal for a home office or a quiet retreat. Down a private hall, the sleeping wing awaits. The primary suite is a true haven, featuring a second fireplace, a charming window seat for reading, a large walk-in closet, and an en-suite bath. Two additional well-proportioned bedrooms with ample closet space share a pristine hall bathroom. A generous two-car attached garage and a full basement offer abundant storage and convenience right off the main entry.Outside, the 8.3-acre grounds are a serene blend of manicured lawn, wild meadow, and mature plantings. The location is truly stellar: less than five minutes to Catamount Mountain Resort for year-round adventure, and just moments from
…By William Pitt Sotheby's International Realty
Step into a world of timeless charm and understated luxury with this impeccably restored 18th-century farmhouse, nestled on over 6 acres of landscaped lawns, flowering gardens, and river frontage along the trout-rich Roe-Jan Kill. The residence exudes warmth and authenticity, offering luminous interiors and inviting outdoor living spaces ideal for entertaining or quiet retreat. The grand living room, anchored by a wood-burning fireplace and lined with a wall of windows, frames views of the grounds and invites natural light throughout the day. The custom-designed kitchen marries modern function with period detail, while the sun-drenched dining room—with exposures on two sides—provides an elegant setting for intimate gatherings. A deep, screened porch spans the length of the north wing, overlooking the gardens and flowing lawns. On the main floor, a serene en suite bedroom and a private guest suite with sitting room and separate entrance offer flexible accommodations. Upstairs, two charming bedrooms share a beautifully appointed bath. A short stroll through lush gardens and across a second private drive leads to the stunning, two-story post-and-beam barn. Currently curated as an antique store, the structure offers an expansive lofted studio and is zoned for commercial or residential use—ideal for a gallery, guesthouse, or creative workspace. This rare, historic compound offers a peaceful, pastoral lifestyle just over two hours from Manhattan—a perfect fusion of old-world charm and modern-day potential. Tucked into the rolling foothills of the Berkshires, Hillsdale is one of the Hudson Valley’s most coveted enclaves—quietly elegant, unspoiled, and deeply rooted in charm. Just over two hours from Manhattan, it offers the ideal blend of refined rural living and easy access to the region’s most sophisticated cultural and culinary experiences. Here, sweeping vistas, winding country roads, and historic farmhouses coexist with curated farm-to-table restaurants, chic design shops, and proximity to world-class destinations like Hudson, Great Barrington, and Tanglewood. Hillsdale is home to Catamount Mountain Resort for year-round recreation, from skiing to ziplining, and just minutes from Copake Lake, private golf clubs, and nature preserves. Discreet, low-key, and deeply authentic, Hillsdale attracts those seeking serenity without sacrifice—an elevated escape that feels worlds away, yet entirely within reach. Hillsdale is fast becoming one of one of Columbia County’s most desirable investment destinations. Just over two hours from Manhattan, this historic town offers a rare combination of timeless charm and smart, long-term value. As boutique hospitality, curated design, and high-end food culture continue to expand nearby—in Hudson, Great Barrington, and Chatham—Hillsdale has quietly emerged as a prime location for luxury second homes and discreet development. With a strong track record of appreciation and zoning that allows for flexibility, it's an ideal market for those looking to balance lifestyle with strategic growth Hillsdale offers proximity to a refined network of private clubs, golf courses, and recreational resorts that define the elevated Hudson Valley lifestyle. You're just minutes from the exclusive Copake Country Club, private lakefront communities, and the slopes of Catamount Mountain, offering four-season access to skiing, hiking, and ziplining. Paired with nearby spas, organic farms, and award-winning restaurants, Hillsdale is a magnet for those who appreciate privacy, taste, and a quietly luxurious pace—without sacrificing access to world-class experiences.
…By Four Seasons Sotheby's International Realty
For the first time on the market in 50 years, Underwood Farm, with its late 18th century cedar shake 3200 square foot salt box house, is 281 acres of primo hilltop exposure. Driving the property, the entire expanse is the high ground between West End Road and Rockledge Road with its equal parts woods, open meadows and fields with the rolling Taconics to the East. Below, the neighborhood is experiencing a renaissance and is dotted with new restorations of gorgeous farmhouses and new builds, adding a fresh dynamic to the area. This site is perfect for any health and wellness guru looking to recreate life on a farm for the benefit of the community, for an hotelier or hospitality group to develop an Upstate experience compound or simply to restore a piece of American architectural history to become a beautiful 4 bedroom 2 bathroom residence in the heart of the Craryville to Hillsdale corridor and all the conveniences that entails. The house sits high on a bluff overlooking West End Road and below the dale is a large former dairy barn with a metal roof and cattle stalls. There is a detached garage with an efficiency apartment over it behind the house with the opportunity to plant a crop in an adjacent waiting field. Three large parcels make up this offering and the residence has the opportunity to sell the remaining two while maintaining 100 acres for an impressive estate.
…By Four Seasons Sotheby's International Realty
If you can imagine living in a stunning mountain view shed among poetic gardens, Three Willows, an adorable Cape Cottage built in 1954 in the historic hamlet of Copake, NY, must be right for you. This wonderfully situated 2 bedroom 2.5 bathroom residence is located in the quaint hamlet center within walking distance to both the Copake General Store and the local yoga studio. The grounds of this lovely home are a garden paradise with waves of beautifully curated and native New York blooms for every week in season accompanied by a soul soothing, protected view of the Taconic mountain range at Bash Bish Falls and it's own deep, spring fed pond for a cold plunge beneath a giant, gentle willow amongst the birch and the bees. The kitchen boasts clean, white Viking appliances with a center island for the chef’s convenience with custom cabinetry and granite countertops with a dining area overlooking the back gardens and mountain views. The house is all electric and efficient with systems in place built to walk away and head to the city with ease. The two bedrooms are both en suite and very separate from one another, allowing for guests’ privacy. A home for all seasons with a park like setting for both gardening galore and cross country skiing across a wide expanse of snow covered hills for the winter buffs. The hamlet of Copake is a mini fertile valley contained within the wider Hudson Valley because it lies at the foot of the Mt. Washington State Forest with its magnificent Bash Bish waterfall flowing into the famed Roeliff Jansen Kill through the community and it’s contiguity of both Berkshires and Taconic ranges. Much like a little gem lettuce patch, this Copake hamlet boasts some of the very best alluvial soil and, therefore, produce in the region. Copake is definitely becoming an established flower farming community and this offering holds its own as a notable garden in the area.
…By Four Seasons Sotheby's International Realty
Wildflower Hill is a rare and distinctive country retreat set behind a gated entrance on nearly six private acres in the gently rolling countryside of Southern Columbia County. Tucked behind mature trees and open lawns in the heart of Ancram, this four-bedroom, two-and-a-half-bath residence offers over 3,900 square feet of well-proportioned living space, where reclaimed wood beams, abundant natural light, a striking stone fireplace, and artful architectural details create a home of warmth, character, and timeless style. Designed for relaxed daily living, weekend entertaining, and four-season enjoyment, the interiors unfold through generous living and dining spaces with an easy connection to the outdoors. A large deck overlooks the grounds and extends the home beautifully for summer dinners, visiting guests, and quiet mornings in the country. Recent improvements include a brand-new boiler and brand-new septic system, offering immediate comfort, efficiency, and long-term peace of mind. Outside, the setting is both serene and full of charm. A koi pond, fruit trees, rolling lawns, fenced garden, and light-filled potting shed create a property that feels established, private, and deeply connected to the land. The acreage is beautiful and usable, with room to garden, entertain, explore, or simply enjoy the quiet rhythm of the seasons. Wildflower Hill balances privacy with exceptional access to the region's most beloved destinations. A short walk leads to the Ancram Little Store for coffee, breakfast, lunch, local cheeses, dairy, teas, and seasonal provisions. Farmers Wife is approximately six minutes away, Hillrock Estate Distillery is approximately nine minutes away, and Stissing House is about thirteen minutes away for celebrated farm-to-table dining. Millerton is roughly fifteen minutes away for restaurants, shopping, The Moviehouse, and Oblong Books, while Mashomack Polo Club, Catamount Mountain Resort, Hudson, Hillsdale, and the Berkshires are all within easy reach. New York City is approximately two hours away. Equally suited as a full-time residence, refined weekend retreat, or year-round lifestyle investment, Wildflower Hill captures the enduring appeal of Hudson Valley living with privacy, character, and a setting worth discovering.
…By William Pitt Sotheby's International Realty
Welcome to 240 Stevers Crossing in Hudson. This warm and inviting home features a new roof (2023), gutters (2024), electrical upgrade (2025), oil tank (2025), new septic tank and new leach fields (2021), and new bedroom carpets (2025). Enjoy cozy winters by the fireplace and a spacious yard that's perfect for kids and outdoor gatherings. The location is ideal for nature lovers, with High Falls Park less than a mile away, Olana and Bash Bish Falls nearby, and plenty of trails for hiking and biking. Just minutes from Hudson's Amtrak station, antique shops, and great restaurants, this home offers comfort, convenience, and the best of Hudson Valley living. HIGHEST AND BEST OFFERS DUE BY 12PM ON SUNDAY 3/29.
…By Julia B. Fee Sotheby's International Realty
Welcome to Wolverton Creative Compound, a storied 119-acre estate set within a hidden valley offering complete seclusion, integrated creative workspaces, and timeless beauty. The original 1830s farmhouse is tucked away at the end of a private lane in Claverack, NY, where the road terminates in a round gravel driveway anchored by the property's original stone well. Two large ponds grace the land, including an aerated, swimmable pond directly in front of the house. Sited among meadows and mature woodlands, the main house, upgraded studio barn, and charming studio shed are framed by terraced stonework, a network of trails, and thoughtfully designed gardens. The setting is peaceful, restorative, and deeply connected to the land, yet only a short drive to both Hudson and Great Barrington.The antique farmhouse offers four bedrooms and two bathrooms across 2,825 square feet, where original details like moldings, wood floors, and Dutch doors preserve its old-world charm. A generous double living room and a Vitsoe-outfitted studio lead to a bright dining area and kitchen, each with direct access to patios and gardens. The layout supports an easy indoor-outdoor rhythm, with covered porches and multiple terraces for lounging, cooking, or gathering. Two staircases rise to the upper-level bedrooms, where southern exposure fills each room with light, and the insulated attic improves year-round comfort. Throughout the home, an intentional color palette lends softness and cohesion. The design brings together European sensibility and Hudson Valley character, creating a live-work compound that balances utility with ease, warmth, and quiet sophistication.Across the garden sits a fully insulated 1,900-square-foot historic barn transformed into a large-scale creative studio, complete with bathroom and clawfoot tub, kitchenette, updated electrical, and HVAC. The studio is wired for photography, cinematography, sound, editing, and workshop use, with fiber-optic service and an underground data connection linking house and studio. The compound has a full HUE lighting system with states created by a film lighting designer. A detached potting shed offers another versatile space, ideal as a garden studio, writer's nook, or future guest cottage, and connects to an outdoor bath deck that invites restorative soaks beneath the stars with its fireplace, clawfoot tub, and outdoor shower. A carport at the barn with EV charging and a full-property generator ensure comfort and continuity year-round, whether for everyday living or on-site production. A whole-house water filtration system adds another layer of comfort.The primary pond is the centerpiece of the property. This aerated, swimmable pond, bordered by a pebble beach and firepit, is ideal for swimming or evening gatherings after a day in the studio. Terraced gardens by The Secret Gardener surround the home with a cottage-style blend of flowering plants, herbs, and vegetables. Rewilded fields and meadows lead to two miles of maintained trails through native grasses and towering trees. The land qualifies for a forestry exemption and includes multiple cleared areas, offering potential for a guest house, additional studios, horses, or even a helipad. Whether hosting music on the lawn, staging a shoot, convening a creative team, or watching the changing sky reflect in the pond, Wolverton Creative Compound is a rare legacy estate and true sanctuary for creative work and retreat.
…By Annonceur International
For the first time in history, Mill Farm — Spanning more than 2,000 contiguous acres in Ancramdale, New York, — is being offered to the market. Almost all of the farm is surrounded by thousands of acres of adjacent protected conservation land, making it the only 2,000-acre working farm in the region, ensuring a level of privacy and ecological integrity that cannot be duplicated. Steeped in history, The Mill House dates back to the Revolutionary War era and the Livingston family, and is the conversion of the famed Grist Mill “Defiance,” a rare surviving landmark of early American industry that established the region’s first foundation of commerce. At its core is the Mill House, an approximately 5,600-square-foot architectural treasure set directly on the Punch Brook Stream, where the water flows through the home itself to power its historic hydro turbine mill system. There is a waterfall set close to the Mill House that is an ever present living feature of the environs, as it is closely visible from nearly every room. Adjacent, the former Mill Keeper’s House has been reimagined as a private movie theatre, blending centuries-old character with modern indulgence. Crest Lane, an approximately 3,500-square-foot masterpiece, stands as a second architectural jewel, featuring a windowed living room with sweeping views across the valley. Beyond these primary residences, the property includes 8 single-family homes, including four newly renovated cottages, each on its own deeded parcel, offering unmatched flexibility for family, guests, or future investment. The two main residences, the Mill House and Crest Lane, are connected by a three-mile internal gravel road system. The land itself is a defining asset. This is arguably the largest working farm within two hours of New York City, with organic-certified hay production, fertile valley floors, and rising elevations to both the east and west that frame extraordinary views. Rare 18th-century barns, including a remarkable Dutch Barn, stand as enduring testaments to America’s agrarian history. An active windmill system still feeds water to various points across the farm, while aquifers and tributaries ensure abundant water availability. Recreational and ecological value are equally profound. The farm contains more than 18 miles of perfected, drivable trails that interconnect every corner of the property, creating a network for horse riding, exploration, and access to resources. Three miles of the untouched Punch Brook, a designated New York State trout stream, run through the property—a pristine waterway under private stewardship. The farm is also home to documented bobcat habitats and study areas in partnership with Panthera.org. Its eastern boundary adjoins a vast conservation bird sanctuary, ensuring uninterrupted natural surroundings and extending the feeling of total seclusion for thousands of acres in every direction. Mill Farm uniquely combines agricultural productivity, historical resonance, and ecological significance. With its unmatched scale, legacy, and proximity to New York City, it represents an opportunity that exists nowhere else in the Northeast — a living landmark, never before available on the open market.
…By Annonceur International
Welcome to an exceptional Hudson Valley retreat, offering unparalleled space, comfort, and recreational amenities across 56+ private acres. This stunning 6 bedroom, 6.5 bath estate is the ultimate compound or a lucrative opportunity for investors seeking a proven Airbnb performer. Nestled in a secluded setting, the property features a swimmable pond with its own docks and bridge, plus scenic trails perfect for snowmobiling, hiking, and cross-country skiing--all from your own backyard. Designed for gatherings and entertaining, the grand open-concept living, dining, and kitchen area is anchored by a dramatic stone fireplace with a propane stove insert. The chef's kitchen is outfitted with two refrigerators, two ovens, a five-burner stove, and a wine fridge--ideal for preparing feasts for a crowd. An expansive laundry room boasts three washers and six dryers to handle large groups with ease. The indoor heated pool, personal gym, and game room, complemented by a second cozy fireplace with propane stove insert, ensures endless indoor fun, while two private cabins offer exciting renovation potential. Updated mechanicals, on-demand propane hot water, a whole house generator, and a detached two-car garage with its own well provide peace of mind and convenience. Property outfitted with 8 kayaks and a paddle boat. Sub-dividable acreage allows for future expansion or investment flexibility. Whether seeking a weekend sanctuary, a multifaceted compound, or a high-performing rental, this extraordinary property offers boundless possibilities for relaxation, recreation, and return.
…By Four Seasons Sotheby's International Realty
Set way back from the road is this spacious, 5-Bedroom, 4.5 Bath Contemporary farmhouse which embodies timeless craftsmanship and country charm. This carefully curated home is a blend of natural stone, hand-hewn repurposed Hemlock timber beams, honey colored wide board Pine flooring, fine finishes and efficient systems throughout. Inside the front door lies a Great Room with a 25' high cathedral ceiling. Anchoring the ground level and the core of the house, the Great Room features a dramatic field stone fireplace with a blue stone hearth and roughhewn mantle. French doors off the room lead to 12' x 10' covered porch overlooking the pool. The open-concept layout flows into a chef's Kitchen. There's a Palomino granite topped island with a porcelain farm sink, Bertozzoni stainless dishwasher, ample under counter storage, and counter stools for gathering.. Above is a coffered beamed pine ceiling. The Bertozzoni 6-burner gas stove with stove top grill, gas oven and convection oven, and Frigidaire Professional 36 inch stainless side by side refrigerator and freezer are ideal for all farm to table meal prep and entertaining. A walk-in Pantry with coffee station and shelves for lots of dry storage is nearby. A Breakfast area for casual meals is just off the island, but there is also a Dining Room off the Great Room as well. A back hall with a Walnut rough edge bench, open shelving and an outerwear closet. There is also a well appointed Laundry Room with new Maytag washer dryer, polished concrete counter tops, a porcelain farm sink, and built in cabinetry for handy laundry and cleaning supply storage. The ground floor Primary Suite features a 10'X8' walk-in closet with built in cubby and double rod hanging storage. This spacious room has pine wide board floors and a coffered, pickled barn wood ceiling. It adjoins the spacious Primary Bath with marble topped double vanities, walk-in shower with tile surround and black river pebble floor next to an oversized soaking Kohler tub. The Primary Suite feels like a private retreat with French door leading out to the pool area. Upstairs above the Primary is a Bedroom suite with a Full Bath. Crossing back through the Great Room is another wing with two ground floor Bedrooms each with walk in closets and a shared Full Bath. Upstairs is an additional large Bedroom that could also serve as a Media Room or Gym. An Office is located on this level with an ensuite Bath.The home's systems are energy efficient including Broud Propane 4 zone heating, 80 gallon hot water heater, whole house, zoned air conditioning with Mitsubishi mini splits on each wing of the upstairs and a whole house 22kw generator. Marvin windows throughout. Septic tank is 1250 gallons and the well is 160ft with a 50-gallon a minute flow. Outside is the 20x40 ft, heated, mineral pool with blue stone surround. There's also an outdoor kitchen with hot and cold water, refrigerator, grills and counters under a beamed canopy. Beautifully landscaped yard is completely fenced. Oversized two car garage with parking area is tucked to the side of the home. Down the driveway to the stone entry pillars is a heritage two bay Barn with loft and side storage room ideal for studio or could be finished as another guest house or air B&B. Whether used as a year-round residence or a seasonal escape, this contemporary farmhouse captures the spirit of refined modern living--where comfort, craftsmanship, nature, and rural living meet. Ten minutes to Hudson shopping and galleries and Amtrak. And, just around the corner is Morningstar Farm Market with great offerings from their farm and other local growers and makers. Come see it!
…By Annonceur International
Experience the best of upstate living in this recently renovated single-family home, designed for comfort, entertaining, and relaxation. Perched high on a quiet country road, this expansive 3,280 sq. ft. residence offers sweeping views of both the Catskill and Berkshire Mountains. Inside, natural light floods the open living spaces, highlighting hardwood and ceramic tile floors. The chef's eat in kitchen is equipped with a 6-burner 48 inch Viking stove, generous counter space, and opens to a formal dining room--ideal for hosting guests. The spacious living room features a cozy propane stove, perfect for chilly evenings. A luxurious first-floor main suite includes a spa-inspired bathroom with a soaking tub, walk in shower, bidet, and breathtaking mountain vistas. Three additional bedrooms and two laundry areas provide flexibility for larger households or guests. Step outside to manicured patios, mature fruit trees, and a 6-person hot tub on the inviting wrap-around deck overlooking the panoramic scenery. Investors and weekenders will appreciate the successful Airbnb history, turnkey condition, and desirable location. With a two-car attached garage, one bay currently used as a gym area, an expansive basement waiting for your vision, generator, 2 brand new central ac units, 2 furnaces, and over 3+ acres to call your own, this home offers privacy, serenity, and potential. Whether you're seeking a primary residence, a getaway retreat, or an investment opportunity, this remarkable property is ready to exceed your expectations. Schedule your tour today and embrace the peaceful luxury of country living.
…By Four Seasons Sotheby's International Realty
Exquisite private Tudor-style stucco estate set on more than 18 breathtaking acres with panoramic views and a winding approach that creates an extraordinary sense of arrival. Bright, airy, and thoughtfully designed, this 5-bedroom, 5-bath residence blends timeless architecture with modern comfort and exceptional indoor-outdoor living. The heart of the home is a stunning great room featuring soaring ceilings, a majestic fireplace, abundant natural light, and hardwood floors throughout. An open-concept layout flows seamlessly into the generous chef's kitchen, complete with a professional-grade gas range, spacious dining area, and direct access to the expansive deck overlooking the rolling landscape. The main-level primary suite offers privacy and convenience with a spacious bath and serene views. Upstairs, a second-floor family room overlooks the great room below and is complemented by two additional en suite bedrooms. A separate guest suite includes its own bedroom, bath, and workout area, ideal for visitors or extended stays. Additional highlights include a sunroom, seasonal screened porch, custom-built freshwater swimming pond, and a full walk-out basement ready to be finished for additional living space. Enjoy deeded rights to Prospect Lake, just minutes from downtown Great Barrington, all while benefiting from low Egremont property taxes.
…By William Pitt Sotheby's International Realty
A unique live/work opportunity just outside Hudson proper. Once the Claverack Rail Station, the workshop and galleries at 33 Maple are a chance to own a piece of Columbia County history. The property is made up of three historic buildings dating back to 1870 and varying in size and function. The site is pastoral, 3.5 acres of rolling green grass under a canopy of large maples. You’ll spot the old rail bed out back. For the last 35 years the property has served as a center for world-class craftsmanship in architectural restoration and antique furniture conservation, first under Sotheby’s and now STAIR Galleries. Exceptionally well cared for, utilities have been run underground and the mechanicals kept up-to-date throughout their decades-long tenure.The main building is large, spanning 8,000 square feet with high ceilings and large, open spaces. It has a standing seam metal roof and the loading dock can accommodate a large truck. Next door the 1,000 square foot ticket office is charming in its many historic details, the original ticket counter and built-in bench seating have been saved and restored. It most recently served as a jeweler’s workshop, while the final building, once a waystation for coal and hay sales and currently fitted as a small private personal gym, serves as a medical office spanning two floors with a kitchen. The site is comprised of four distinct parcels and over 10,000 square feet of space. Perfect for an artist or craftsperson, a production studio or workshop, or to build your dream home, the possibilities are endless. You are in the heart of the Hudson Valley just 10m to Amtrak and 2h to NYC.
…By Four Seasons Sotheby's International Realty
Down a quiet country road just minutes to Hudson, this 2022 custom-built modern home sits within a rare landscape of protected farmland, open fields, and long pastoral views. The setting feels expansive and quietly intact, with fields, meadows, and forest stretching toward distant estates on the horizon. Designed with simplicity, efficiency, and permanence in mind, the house is wrapped in COR-TEN steel cladding and is fitted with European triple-pane windows, creating a thermally efficient and low maintenance home. Inside, the interiors are calm and precisely composed: 10–12 foot ceilings, concrete floors with radiant heat, a wood-burning stove, and a sense of light that shifts beautifully throughout the day. In winter, passive solar gain brings much warmth deep into the living spaces, while in summer cedar louvers and orientation keep the home naturally cool. All systems are new, including well, septic, and mechanicals. The upper level offers flexible space for office, studio, or additional sleeping quarters. Outside, the land has been shaped into a series of living landscapes. A woodland garden has been restored with native ground cover and grasses, while a fern-planted stone wall traces the edge of the property, echoing early settler history. A large pollinator garden draws butterflies, bees, and hummingbirds. This home's immediate access to a network of quiet country roads invite cycling and running directly from the driveway. The large steel outbuilding is currently used for storage and parking, but could make for a fabulous studio or additional living space. Set among protected farmland with open views in every direction, the property offers a rare combination of design clarity, low maintenance living, and deep connection to its surrounding landscape.
…By Four Seasons Sotheby's International Realty
Discover a rare blend of modern functionality and classic charm in this meticulously-maintained Cape, ideally situated on over 3.5 private acres in the sought-after, low-tax town of Egremont. With a serene woodland backdrop, this bright and airy home offers an elevated living experience with open-concept flow and seamless indoor-outdoor integration. Thoughtfully designed with wheelchair accessibility at the forefront, this home features expansive, light-filled spaces including a chef's kitchen and open dining area, and a screened porch. Beyond the main living quarters, the lower level hosts a versatile apartment, perfect for guests or multi-generational living. Just moments from French Park and the cultural heartbeat of Berkshire County, this 4-bed, 3-bath home provides a private sanctuary without sacrificing proximity to the region's premier attractions.
…By William Pitt Sotheby's International Realty
Spectacularly renovated and offered for the first time since its complete transformation, this exceptional pond front residence overlooking Maiden Lake is located within the highly sought-after Fern Hill community and offers refined design, privacy, and effortless indoor-outdoor living. The home is clad in warm natural cedar siding, lending timeless character while blending seamlessly with the surrounding landscape. Maiden Lake is a shared pond maintained by the Fern Hill HOA with private swimming access. Set on a quiet country road just outside the Hawthorne Valley hamlet, the property is minutes to Great Barrington, Massachusetts, close to respected private schools, and offers convenient access to the Taconic Parkway and Albany International Airport, allowing for easy travel from New York, Boston, and Connecticut. The thoughtfully designed home features multiple private bedroom suites, lofted ceilings, and expansive light-filled living spaces. Interior finishes highlight exceptional natural materials and craftsmanship, including white oak flooring in the main living areas, cherry cabinetry, soapstone kitchen countertops, French oak stairs, and a custom single-stringer stair with a black steel beam, black steel railing, and white oak banister. Bedroom suites feature maple flooring, while the upstairs loft, office, or studio includes wide-board pine floors. Custom wainscoting and a dedicated linen closet serve the bedroom suite hallway. The open main living area centers around a well-appointed chef's kitchen with an oversized dining island and additional dining space. Premium stainless steel appliances include a Bosch wall oven, Thermador gas cooktop, Fisher and Paykel refrigerator, KitchenAid dishwasher, and Zephyr range hood. Bathrooms feature white subway tile, marble sink countertops, rain and hand-shower fixtures, and wood-grained porcelain tile flooring. The home is filled with light and comfort through Marvin triple-pane windows and doors with built-in shades, automated skylights, and thermal skylight shades. Ceiling fans, insulated thermic shades, and remote-operated skylights enhance energy efficiency and airflow. Multiple dedicated home office areas support flexible modern living. Year-round comfort is provided by an energy-efficient heat pump system with heating and cooling, radiant heated floors in the main living areas and primary bathroom, and a separate gas furnace serving the rear portion of the home. A whole house backup generator provides added peace of mind. Additional upgrades include high-efficiency insulation, fully updated plumbing and electrical systems, a 400-amp electric service, and ethernet outlets. A gas fireplace adds warmth to the main living space. The laundry room includes cherry cabinetry and Bosch stackable washer and dryer units. The entry mudroom features a brick floor, bluestone bench seating, antique wood beams, a Buderus European-style radiator, abundant windows and skylights, and generous storage. The landscaped grounds include perennial gardens, bluestone walkways, copper gutters and drainspouts, selective fencing suitable for small livestock or chickens, and fenced raised-bed gardens. A charming barn includes a three-to-four-person luxury sauna with an Amerec SaunaLogic controller and Laava series heater. Outdoor living is exceptional, with an expansive wraparound Brazilian walnut deck, a spacious gazebo with sweeping pond views, an additional deck overlooking the water, and a dock. This rare offering blends natural beauty, modern comfort, and the coveted Fern Hill lifestyle in an ideal location. Cultural destinations like Hudson galleries, Art Omi, Tanglewood, and Jacob's Pillow are nearby, along with skiing at Catamount, Jiminy Peak, and Butternut. Best of all, Hawthorne Valley Waldorf School and the renowned Hawthorne Valley Farm Store—featuring the highest quality local, organic, and biodynamic food—are just moments away by foot or bicycle.
…By William Pitt Sotheby's International Realty
Experience the luxury of gracious proportions, impeccable details, and stunning design in this exquisite classical villa that would be as at home in Italy as it is in the Berkshire landscape. Protected views of mountains, rolling hills, and meadows surround the 6.9-acre estate. The atmosphere of sophisticated luxury begins with the approach through an allee of willow trees and in the front courtyard, edged with stately Bradford pear trees and arbor vitae and anchored by the 2716sf, single-level residence and a matched pair of outbuildings--a two-car garage and a garden house. The front entry of architect-designed residence leads to a luminous interior with tall ceilings, reflective white walls, generous windows and 19 screened French doors that welcome sunlight and breezes and provide for ideal interior-exterior living. To the left of the entry are a living room with a wood-burning Rumford fireplace and hallway to the primary suite with an airy, comfortable bedroom, refined, restorative bath, and walk-in closet/dressing room. To the right, a spacious dining room, well-appointed kitchen, screened porch, and hallway to two bedrooms and full bath. The U-shaped floor plan embraces a secluded formal garden, reflecting pool with fountain, patio with pergola, and 40' lap pool. Completed in 1998, every element of the residence attests to architectural intelligence, superior craftsmanship, and love for the bucolic landscape. The high level of quality is evident in the visually commanding millwork, true stucco exterior, lath-and plaster walls in the principal rooms, east and south pergolas, west-facing screened porch, and sensitive choreography of space. With roots in the classical architecture of ancient Rome, this is a thoroughly modern dwelling replete with whole-house fan, air conditioning, generator, security system, 630-foot drilled well, and chef-ready appliances. The result is a home that feels both sculptural and deeply connected to its setting. With protected views, total privacy, and proximity to South County amenities (7 minutes to Guido's), this is a rare Berkshire offering -- serene, architecturally stunning, and eminently livable.
…By William Pitt Sotheby's International Realty
Modern comfort meets timeless New England farmhouse charm in this beautifully maintained 3BR/2BA home on 3.2 peaceful acres in Egremont. Filled with natural light, the open-plan kitchen, dining and living spaces feature hardwood floors throughout, updated kitchen and baths, and a warm, inviting flow ideal for everyday living or weekend retreat. Enjoy a spacious primary suite with en suite bath, family room with wood-burning fireplace, full covered front porch, oversized attached 2-car garage, and a large dry basement ready for expansion. Bucolic setting on a quiet country road just minutes to Great Barrington, with exceptionally low Egremont taxes
…By William Pitt Sotheby's International Realty
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.
…By William Pitt Sotheby's International Realty
Rare opportunity to own an enchanting horse farm in the heart of Columbia County. A historic Hudson Valley 1840s center hall Colonial farmhouse sits on over 20 stunning acres of rolling fields, fenced paddocks with water troughs and run-in sheds, a horse barn with a large hay loft and 8 stalls + an additional 3-stall pony shed that could be used as a chicken coop, garden beds, mature trees, a supplementary living space above the garage with a full bathroom, and a charming wooden bridge over a clean spring-fed creek where wild watercress grows. Prime farmland with 3 fields on the property currently leased to neighboring Hawthorne Valley Farm. Step from the L-shaped porch into the bright house filled with character, featuring exposed wood beams, vaulted ceilings, original moldings and wood floors, 2 wood-burning fireplaces, 6 bedrooms including a spacious, first-floor primary bedroom with an en suite bath and a private entrance, 4.5 bathrooms, wet bar, 10' ceilings, plaster walls, window seats, flagstone patio, mudroom. Recent improvements include a brand-new generator, fresh paint, new laundry with a new LG clothes dryer, and recessed LED lighting. This equestrian property is in an idyllic countryside setting and mere minutes from everything one might need in terms of culture, social life, sports and schools for children. N earby Hudson and Rhinebeck offer fine shopping and dining. There's certainly no lack of things to do and places to eat! Take your pick of farm-to-table restaurants, farm stores, farmer's markets, bookstores, bars, cideries, distilleries, hikes, art galleries, antique stores, and more.
…By William Pitt Sotheby's International Realty
Welcome to Cricket Hill Farm-a circa 1949 country home set against sweeping Catskill Mountain views, this home offers the rare opportunity to create your own Hudson Valley retreat. Privately sited with a beautiful front lawn, mature trees, and a gorgeous bluestone patio designed for outdoor dining and summer evenings, the setting alone is worth the drive. Inside, the three-bedroom, two-bath home is filled with character, including hardwood floors throughout and a wood-burning fireplace that anchors the living space. The seller has already gutted the kitchen, opening the space and creating a true blank canvas for the next owner to design and renovate to their taste. The bathrooms are also ready for updating, making this an ideal opportunity for someone with vision looking to bring new life to a well-loved home. A detached one-car garage adds convenience, while the mountain views and established landscape create the kind of setting that's hard to replicate. An authentic Hudson Valley fixer with soul, views, and endless possibility.
…By Four Seasons Sotheby's International Realty
Fantastic opportunity to own a home in a peaceful cul-de-sac within the desirable Cornwall Estates. This lovely home sits on a level lot with almost 2.5 bucolic acres. Spanning just over 2,000 square feet, the home features a convenient first-floor primary bedroom and bathroom, vaulted ceiling in the living room and a screened in porch that leads to a large, partially fenced in backyard. Many recent updates and upgrades including kitchen and bathrooms, as well as the furnace and central AC system replacement. All of this and a heated community pool nearby and Great Barrington just minutes away, make this home ready for its next owners to create their own Berkshire journey and memories. Replaced/Updated Within the Last 3 Years: furnace, central AC, kitchen, bathrooms, all exterior doors, basement improvements Community Details: -8 homes in the community -$1,500 transfer fee due at closing from buyers to the Association -HOA dues will decrease to $900 per quarter ($300 per month) after two loans are paid off in July and October 2027 Rental Policy: -First rental term has a 28-day minimum -Second rental term has a 7-day minimum -Maximum rental term is 1 year -Lease extensions must be approved by the Association
…By William Pitt Sotheby's International Realty
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