luxury real estate for sale Big Indian, United States

Prime Turnkey Investment Property in the Heart of the Catskills – Fleischmanns, NY Located in the heart of the picturesque Catskill Mountains, this exceptional turnkey investment property offers a rare opportunity to own a beautifully maintained home in one of the region's most desirable areas. Just minutes from Belleayre Ski Mountain, this property is perfectly positioned to attract year-round guests, whether they’re seeking a winter getaway or a peaceful retreat in the warmer months. This property is an ideal choice for investors looking for a low-maintenance, high-reward venture. Whether you're interested in short-term vacation rentals or long-term tenants, the property is ready to generate consistent rental income. With its modern amenities and meticulously cared-for living spaces, this home is both comfortable and welcoming. The layout is thoughtfully designed to maximize both functionality and relaxation, making it perfect for guests after a day on the slopes, hiking the nearby trails, or enjoying the stunning natural beauty of the Catskills. The home features spacious living areas, a fully equipped kitchen, and cozy bedrooms. Each room has been updated with stylish finishes, providing a balance of charm and modern convenience. Guests will appreciate the home's inviting atmosphere, with plenty of natural light streaming through large windows that offer scenic views of the surrounding mountains. Step outside to enjoy a wraparound deck, perfect for outdoor dining, entertaining, or simply unwinding in nature. After a day of outdoor adventures, relax in the hot tub and soak in the serene atmosphere of this peaceful retreat. The property’s low upkeep makes it an ideal investment for those seeking a hassle-free ownership experience. With its prime location, the property is in high demand for both short-term and long-term rentals. The nearby Belleayre Ski Mountain is a major draw for winter sports enthusiasts, while the surrounding area offers ample opportunities for hiking, fishing, and exploring the vibrant local community throughout the year. This home blends natural beauty with excellent income potential, making it an exceptional investment opportunity. Whether you’re looking to expand your portfolio or step into the world of vacation rentals, this property offers both immediate and long-term value. Don’t miss your chance to own a piece of the Catskills! **Investor Alert! This is a rare opportunity to purchase three successful Airbnb properties together all on Kleis Spur Road. Add this turnkey, income-generating-package to your portfolio (MLS # 202525576 and 202525578)

Set across 280 extraordinary acres in the Catskills, Eagles Ridge Farm is not merely a property, but a fully realized private world, an irreplaceable convergence of art, architecture, wilderness, and legacy. Bordered by thousands of acres of protected wilderness within the historic sphere of the Gould and Rockefeller Catskills holdings, the estate retains the scale and quiet grandeur of a disappearing era. Assembled over generations, the property carries forward a tradition of deeply personal estates created not simply for habitation, but for reflection, creativity, and permanence. Unlike many great legacy properties lost to subdivision or time, this extraordinary holding remains remarkably intact, a singular offering of cultural depth, ecological scale, and privacy that would be nearly impossible to recreate today. Just over two hours from New York City, the property unfolds across forests, open meadows, private streams, and mountain ridgelines rising to 2,270 feet. More than ten miles of trails weave throughout the land, swimming holes, moss-covered pathways, sculptural clearings, and panoramic viewpoints that feel entirely removed from the modern world. At the heart of the estate lies one of the most extraordinary environmental sculptures ever created, Michael Ayrton's stone maze. Conceived by Wall Street investor and contemporary art collector Armand Erpf after reading Ayrton's The Maze Maker, a fictional autobiography of Daedalus, the work was commissioned directly from the celebrated English sculptor and completed in 1965. Believed to be the largest stone maze built since antiquity, the work stretches approximately 1,680 feet and is anchored by original bronzes depicting Daedalus, Icarus, and the Minotaur. Both artwork and immersive landscape experience, it transforms the property into something far beyond a traditional country estate, a museum-quality assemblage woven into the landscape itself, equal parts philosophical environment and living work of art. Near the entrance to the stone maze, a smaller contemplative labyrinth offers a quieter moment of reflection within the landscape. More than a dozen additional sculptures are woven throughout the grounds, reinforcing the estate's identity as a place shaped as much by imagination as by architecture. The main residence was fully renovated in 2016 for modern mountain living while preserving its timeless relationship to the surrounding landscape. Spanning approximately 5,300 square feet with eight bedrooms and seven-and-a-half baths, the home opens to expansive terraces, formal gardens, wide lawns, and sweeping mountain views. A cupola crowns the residence, creating a rare balance between refinement and wilderness. Beyond a covered cedar staircase and moss-lined bluestone paths sits a beautifully restored 2,800-square-foot brick guest house with three private apartments, offering flexible accommodations for guests, caretakers, artists, or multi-generational living. The estate further includes: An 800-square-foot pool house with kitchenette and changing rooms A heated 56' x 24' pool with expansive bluestone terrace A five-stall horse barn and polo stick-and-ball field Garages accommodating up to six vehicles An office cabin and trout stream pump house A Har-Tru tennis court ready for resurfacing for tennis or pickleball Wired and wireless high-speed internet and comprehensive security infrastructure Existing systems supporting future off-grid energy potential The land itself is among the property's greatest luxuries. Approximately 40 acres of lawns, meadows, and pasture blend into 240 acres of mixed forest traversed by two year-round trout streams, Bush Kill and Dry Brook, creating private swimming holes, wildlife corridors, and a sense of immersion in nature. Importantly, the property remains free of conservation easements and deed restrictions, allowing unusual flexibility for future stewardship.

Nestled in the heart of the beautiful Catskill Mountains, this well-maintained 3-bedroom, 2-bath home offers the perfect blend of comfort, privacy, and convenience. Built in 2012 and featuring approximately 1,560 square feet of living space, the home boasts a spacious, thoughtfully designed layout with generously sized rooms, abundant natural light, and the ease of one-level living. The inviting great room serves as the heart of the home, highlighted by a beautiful fireplace that creates a warm and welcoming atmosphere year-round. The kitchen features attractive butcher block countertops, offering both style and functionality for everyday living and entertaining. Situated on approximately 0.6 acres, the property is designed for enjoying the outdoors. Step into your own private backyard retreat, complete with a pool, hot tub spa, and plenty of space to relax, entertain, and take in the peaceful mountain surroundings. Whether you're hosting summer gatherings, unwinding under the stars, or enjoying your morning coffee, the backyard delivers exceptional Catskills living and vacation-like vibes. Conveniently located just minutes from the Village of Margaretville, you'll enjoy easy access to local shops, restaurants, skiing, hiking, fishing, and all the recreational opportunities the Catskills are known for. Whether you're searching for a full-time residence, a weekend getaway, or an investment opportunity, this property delivers exceptional value in a picturesque setting. Experience the best of country living with modern comforts at 99 Glen Acres Road! This is a place where mountain charm, modern amenities, and outdoor enjoyment come together beautifully.

Tucked away on a quiet country road in the heart of Boiceville, this beautiful three acre parcel offers the kind of peace that's becoming increasingly difficult to find. Towering mature trees create a natural canopy over the property, offering shade, privacy, and an inspiring setting for your future Catskill retreat. Beyond the homesite, the land drops steeply toward the Little Beaver Kill stream below. While the terrain is rugged, there are access points for those who wish to explore. From above, the sound of flowing water rises through the trees, adding a quiet soundtrack that naturally slows the pace and deepens the sense of escape. Thoughtfully improved and ready for its next chapter, the property is serviced by public water, electricity has already been established, the driveway has been roughed in, and a homesite has been cleared, providing an excellent foundation for whatever comes next. Located along the scenic Catskill Byway, Boiceville is perfectly positioned between the vibrant historic city of Kingston and the high peaks of the Catskill Mountains. Hiking trails, world class trout streams, Belleayre Mountain, farm stands, antique shops, and winding back roads are all just minutes away. This is a place where you'll find yourself rolling the windows down, taking the long way home, and breathing a little deeper. Whether you're dreaming of a weekend escape or a full time home immersed in nature, this property offers a rare opportunity to build a life that's a little quieter, a little slower, and deeply connected to the landscape that makes the Catskills so special.

203 Watson Hollow Road is a Creekside Gem Close to Woodstock, NY. A beautiful and impeccably maintained single-family home tucked away on a quiet road near the Ashokan Reservoir includes three bedrooms and one bathroom. The property is a tranquil paradise for outdoor enthusiasts. The gorgeous creek flows year-round and is surrounded by lovely trees and foliage. This exceptional cottage residence is warm and inviting with two wood-burning fireplaces. A stone, wood-burning fireplace is in the living room and another wood burning fireplace in the primary bedroom. A delightful sunroom is ready for entertaining, or reading your favorite book. The kitchen has all the appliances you will need for home cooking. A dishwasher can be added, if desired. There is a washer and dryer, the heating source is propane and central air conditioning was added in 2026, The roof is also new. Effortless convenience to Woodstock, Kingston, and the NY State Thruway makes this dream home in the Hudson Valley the one you have been waiting for.

Lake front Luxury Log Home, in a beautiful setting, minutes to Windham Mountain Club & Hunter Ski Resorts. This is a very special 4 Season vacation home. Enjoy swimming, boating, fishing, hunting & ice skating. The entrance to the property was cut through the forest, creating an enchanting long winding driveway. Ground floor incorporates a generously proportioned kitchen with Hickory cabinets, Quartz countertops, Wolf stove & hand made farm sink with dining area & 1st floor En suite bedroom, welcoming living room with vaulted ceilings & Napoleon wood burning fireplace. Step out onto the beautiful deck for outdoor entertaining. A custom built staircase leads to the 2nd floor with 2 beds, bath & loft. The walkout lower level has a full wet bar, family room, 1 bedroom, bath, laundry room & mud room off the garage. French doors open out to the blue stone patio area leading to the lake.A 3D Walkthrough Tour is available in the digital Lookbook or by request.

Welcome to 270 Kristen Ridge in Margaretville, NY -- a beautifully designed mountain retreat privately situated on 5.1 scenic acres within the exclusive ThornApple Ridge Estates. Located at the end of a quiet cul-de-sac, this exceptional 4-bedroom, 4.5-bath custom home offers breathtaking mountain views from nearly every room and the perfect blend of privacy, comfort, and luxury Catskills living.Expanded in 2013 while maintaining the integrity of the original design, the home now encompasses approximately 4,199 square feet of thoughtfully crafted living space. Designed for both entertaining and relaxation, the property features expansive decks and patio areas, a hot tub, game room with pool table, well-equipped gym, two saunas, and two laundry rooms.The main level welcomes you with an elegant entryway leading to a formal dining room and spacious living room highlighted by vaulted ceilings, oversized windows, and a striking cobblestone wood-burning fireplace. Just beyond is the private primary suite featuring a fireplace, ensuite bath with double sinks, walk-in closet, and a dedicated office area ideal for working from home.A bright stairwell leads to a recreation area complete with a TV room, gym, full bath, laundry room, and an imported custom Finnish sauna with direct access to the outdoor patio and hot tub.The kitchen offers custom cabinetry, granite countertops, skylights, and a wine refrigerator, while the sunny eat-in area opens to the upper deck with panoramic mountain views. Adjacent to the kitchen, the grand sunroom creates a warm and inviting gathering space filled with natural light.The lower level includes three additional bedrooms, two full baths, a second sauna, additional laundry area, and a spacious game room, providing excellent accommodations for guests and family. Residents of ThornApple Ridge enjoy access to a private community pool within an intimate community of only 14 homes, ensuring a peaceful and private atmosphere. Conveniently located just five miles from the village of Margaretville, the property is close to hiking trails, the NYC reservoir for fishing, Hanah Mountain Resort & Country Club, and the ski slopes of Belleayre and Plattekill, with Hunter and Windham also within easy driving distance.This remarkable Catskills retreat offers an exceptional opportunity to enjoy mountain living at its finest, combining luxury amenities with stunning natural beauty.

ONCE-IN-A-LIFETIME OPPORTUNITY: TROPHY PROPERTY on 485 ACRES with +752 ACRES of adjoining NYC land at the end of a quiet town road in Roxbury, NY. Discover mountain vistas, spring-fed ponds, stone walls, and a 500-ft private driveway leading to a pondside home site with grape arbor, footbridge, and gazebo. The 3-bed, 2-bath farmhouse features wood floors, a FIELDSTONE-FIREPLACE, and rustic charm throughout. Additional highlights include a 30x60 barn with STONE PIZZA OVEN, extensive trails, open meadows, and a HIDDEN LOG CABIN retreat overlooking a pristine pond. With this remarkable estate, you'll not only own one of the region's most significant country properties-you'll also be helping to support the lifesaving mission of ST JUDE CHILDREN'S RESEARCH HOSPITAL.

3026 New Kingston Mountain Road is a beautifully composed mountain retreat set on 11 private acres in Roxbury, with sweeping eastern views across the Catskills. The house sits in complete privacy, thoughtfully positioned to capture morning light and expansive long-range views. The setting feels both secluded and connected to the surrounding landscape, with mature trees, layered gardens, and mountain vistas in nearly every direction. Inside, the interiors are warm, understated, and deeply inviting. Soft lime washed walls, warm wood floors, thoughtful built-ins, and a restrained material palette create a home that feels both elevated and entirely livable. The generous great room is anchored by a woodstove and wrapped in windows, while the kitchen balances utility and charm with custom millwork and easy access to the surrounding deck. Bedrooms are quiet and comfortable, and the baths are simple and beautifully executed, with clean lines and timeless materials throughout. The outdoor spaces are equally compelling. An expansive deck overlooks the pond and mountain views beyond, while a cedar hot tub and firepit create natural gathering points across the property. A striking detached studio adds exceptional flexibility—ideal as a workspace, guest overflow, or creative retreat. Private, peaceful, and thoughtfully designed, this is a rare Catskills offering that feels both refined and deeply rooted in place.

A rare opportunity to own a fully designed land and build package set on 10 private acres with sweeping views of the Catskills, surrounded by hundreds of acres of rolling, verdant farmland and pristine, untouched landscape in the sought-after Western Catskills region. Privately positioned on a quiet, no-outlet country road, this setting offers exceptional peace, limited traffic, and a true connection to nature--where open skies, mountain vistas, and unspoiled surroundings define the experience.The proposed residence features approximately 3,400 square feet of modern farmhouse design, highlighted by a spacious open-concept layout and a stunning 640 sq ft wraparound porch--perfect for taking in mountain sunsets, entertaining, or simply enjoying the tranquility of the surrounding countryside. Architectural plans and elevations are complete, offering a clear vision while still allowing flexibility to tailor bedroom configurations, layout details, and finishes to your personal style. Buyers may choose to move forward with the thoughtfully designed farmhouse plan or collaborate with the builder to explore a custom design that reflects their own vision.Designed with quality and efficiency in mind, the home includes high-end construction and finishes throughout, such as premium windows, custom cabinetry, hardwood flooring, granite countertops, energy-efficient systems, and a fireplace feature. Low-maintenance materials and thoughtful building practices provide long-term durability and comfort.What truly sets this offering apart is the ability to build with confidence and ease. The project is led by R.A. Tait LLC, a premier local builder-designer with over 70 years of combined expertise, this builder and his team, will oversee the entire process from the ground up. From site work to final finishes, every phase is professionally managed--eliminating the need for buyers to coordinate subcontractors or navigate the complexities of construction. This streamlined approach allows you to enjoy the creative aspects of customization while the build is handled with precision and care.Adding to the appeal, infrastructure is planned and in place, including road access, electric, proposed well, septic design, and site preparation--allowing for a smooth and efficient building timeline.Optional enhancements may include a whole-house generator, underground utilities, a private pond, and additional exterior upgrades--further elevating the property's lifestyle and long-term value.Additional Opportunity:An adjoining 14+ acre parcel located directly across the street is also available, featuring a 6-stall horse barn, rolling open acreage, and a scenic stream--ideal for equestrian use, recreation, or creating a larger Catskills estate.Set just a short drive to Windham, Hunter, and Belleayre Mountains, this property offers the perfect balance of seclusion and accessibility, ideal as a full-time residence, weekend retreat, or investment opportunity.This offering presents an opportunity to establish a true Catskills estate--your custom home set privately on one side, with the option for equestrian facilities and open rolling acreage across the street--an exceptional and seldom available pairing.

Modern Mountain Retreat with Hunter Mountain Ski Slope Views, Hot Tub & Entertainer's Dream Layout. Perfectly positioned in the heart of Hunter and capturing direct views of the Hunter Mountain ski slopes, this contemporary mountain retreat offers the ultimate combination of style, comfort, and four-season adventure. Designed with entertaining in mind, nearly the entire main level unfolds as one dramatic open living space highlighted by soaring pine vaulted ceilings, walls of glass framing breathtaking mountain and trail views, and a stunning double-sided stone fireplace anchoring the great room, bar area, and recreation space. Multiple sliding doors lead to expansive decking, creating seamless indoor-outdoor living and the perfect setting for après-ski gatherings, summer entertaining, or relaxing while overlooking the slopes. A woodstove adds additional warmth and mountain charm to the already inviting living area. The updated kitchen blends modern design with functionality, featuring crisp white cabinetry, stone countertops, breakfast bar seating, and stainless-steel appliances including Bosch. The beautifully renovated half bath showcases sleek subway tile and offers convenient access from both the main living area and the upstairs bathroom layout. The lower level is thoughtfully designed for hosting large groups, getaways, or future short-term rental potential. Four additional bedrooms -- including two en-suites -- and a common area full bathroom offer plenty of space for guests. A dedicated gym rounds out the amenities, while a separate gear entry provides the perfect landing spot for skis, snowboards, mountain bikes, fishing equipment, and all your outdoor essentials after a day exploring the Catskills. Step outside to your private hot tub retreat complete with privacy enclosure, ideal for relaxing after skiing at Hunter Mountain or hiking nearby trails. Whether you're searching for a stylish ski house, vacation home, Airbnb investment opportunity, or year-round Catskills escape, 109 Botti Drive delivers the mountain lifestyle buyers are searching for just minutes from skiing, dining, hiking, golf, and all that Hunter and the surrounding Catskills have to offer. A 3D Walkthrough Tour is available in the digital Lookbook or by request

There's a distinctly Bohemian heartbeat to this Woodstock compound -- the kind of place where every corner feels like it has a story to tell or awaits the hearing of yours. The 1850 respectfully updated, original farmhouse, with its rich hand-hewn beams, gleaming wide floorboards, and six over six windows carries the patina of time, offering warmth, charm, and the kind of character that make old homes irresistible. The early 1990's addition expands the residence to provide alluring and flexible usage. This home is soulful, and available for those who appreciate authenticity. In the living room, with its two directions of light, an old brick fireplace anchors the space with rustic charm. The intimate, fully equipped kitchen with a natural stone seating bar & the beamed dining room feel like the heart of a true country home: Fetch, prepare and enjoy the local farmland bounty. The vaulted gathering room is dramatic with its absolutely fabulous wallpaper and 16' north light wall offering pastoral views into a peaceful meadow making it an ideal spot for music, reading, long conversations and rest. French doors open onto a stone patio and into the garden where, through the arbor, a sheltered brook offers its expected coolness and melodic sounds. In every season, this land provides a visual symphony and an earned sanctuary. The property's creative soul radiates in the 4-season studio, a 1000sqft space, w/ a 20' skylit ceiling, that beckons your creative expression no matter the medium - paint, sculpture, music, or movement, in group or solo. A bluestone path leads beneath massive trees to a woodworking shop offering yet another layer of creative opportunity. In the home, the hobby room was Harriet Tannin's darkroom, ready to once again function as such. Perhaps here is where she pioneered photo weaving. The buildings and property provide the atmosphere for your projects and expression long awaiting their and your realization. Together, these elements form a true Woodstock compound, walking distance from the celebrated Bearsville Theater Campus: An historic acoustic showcase from the '70s for leading artists, and revived in 2019 as a platform for ongoing musical and film venues, a unique event space, as well as local fare. The property's three buildings shape a natural, secluded courtyard and quiet oasis. Delightfully sited on over 3.5 poetic acres with exquisite old growth trees, flowering shrubs, and adjacent to larger land, this is a place for one who sees beauty in creation, who values character and nature, and who's been waiting to have an antique home, workspace, and creative life all in one. This inspiring property is a refreshing homage to the old Woodstock. It feels like home from your first step inside. Just minutes from the renowned village, yet a world apart.

Enchanting Woodstock Compound with three separate buildings—Craftsman Home, Historic Barn & Cottage. Welcome to a truly rare offering in the heart of the Catskills—just minutes from the center of Woodstock, yet tucked away in a storybook setting of trees, meadows, and the soothing sounds of the Sawkill stream. This private 1.85-acre homestead compound blends rustic charm with modern versatility, featuring three distinct buildings, including a licensed short-term rental ready Craftsman home, a historic converted barn, and a sun-drenched cottage—each with its own character, purpose, and potential. The Craftsman Home. Thoughtfully restored and offered fully furnished, this two-story residence boasts cozy elegance and charm. An inviting front porch sets the tone for relaxed country living, while the 3-season sunroom offers the perfect perch for morning coffee or quiet reading. Inside, original hardwood floors, wainscoted ceilings, and a bright, open layout offer space for entertainment and relaxation. Upstairs, two bedrooms and a stylish bath provide a peaceful retreat. The dry, spacious basement offers extra storage or workshop potential. Currently a operating as a short-term rental, this home is truly turn-key for those seeking an income-producing property or an effortless weekend escape. The Converted Barn. Once home to the Bearsville Woodworking Collective, where the famed Pete Seeger commissioned the building of the Hudson River Sloop, Woody Guthrie, this large barn holds a legacy of artistry and craftsmanship. Its soaring ceilings, open floor plan, and natural light make it ideal for a studio, gallery, or workshop. French doors open to a bluestone patio overlooking stone gardens and field—an inspiring space for creatives or gatherings. The upper attic provides additional space for storage or future expansion. The Bearsville Cottage. A charming blend of vintage soul and creative flair, this one-bedroom cottage is perfect as a guest house, rental unit, or home office. Exposed wood beams, oversized artist windows, and a cozy woodstove make the living space both inspiring and inviting. A private bedroom entrance offers added privacy for tenants or guests, while the open kitchen and living area seamlessly extends into the backyard for easy indoor-outdoor living. The Land & Location. The Woodstock compound is fully fenced with fruit trees, open fields, and garden beds—ideal for farming, raising chickens, or simply enjoying quiet nights under the stars. A babbling creek runs year-round, adding to the property's natural serenity. Whether you're dreaming of a regenerative homestead, a live/work artist's retreat, a multi-generational family property, or an income-generating opportunity, this magical compound offers flexibility and soul in equal measure. Located just minutes from Woodstock's vibrant restaurants, music venues including the Bearsville Theater, and art galleries—with easy access to hiking, swimming, and all the natural beauty of the Catskills—this is a truly one-of-a-kind offering where history, nature, and creative potential come together. Note: Short-term rental income available upon request.

Hidden among the trees and just seven minutes from the center of Woodstock, this 1970s contemporary feels like a private creative compound, untouched in all the right ways. Set on 2 wooded acres with the Sawkill Creek at the rear of the property, the home unfolds through a series of unexpected spaces and strong architectural moments. A dramatic sunken living room anchors the house, centered around an oversized stone fireplace and framed by walls of glass that draw the surrounding landscape indoors. The original design language remains beautifully intact throughout, offering the rare opportunity to own a true period home rather than a generic renovation. The layout is expansive and flexible with over 2,700 square feet, 3 bedrooms, 2.5 baths, and multiple gathering spaces that open naturally toward the outdoors. Off the kitchen, a tucked-away courtyard deck creates an especially inviting area for dining, entertaining, or slow summer evenings beneath the trees. A luminous 500 sq ft porch overlooks the gunite pool, while a separate studio building introduces endless possibilities: artist studio, guest overflow, workspace, movement room, or retreat space. At the edge of the property sits a whimsical treehouse tucked into the woods, adding yet another layer to the property's distinctly Woodstock character. Longtime home to Woodstock artist Lenny Kislin, the property carries a deeply creative spirit shaped over decades. An acclaimed assemblage artist, Kislin created witty and deeply poignant sculptures by bringing together carefully sourced antique components and found objects, transforming fragments of the past into works rich with meaning and imagination. His work remains integrated throughout the home and studio. Private, architectural, and rich with atmosphere, 41 Wittenberg is a rare offering. This property has genuine soul, minutes from the center of Woodstock yet entirely its own world.

In the heart of Woodstock, this extraordinary 12+ acre Woodstock estate offers a rare blend of privacy, natural beauty, and village convenience. The property has a huge meadow/field in back and front offering peaceful pastoral views & potential. Bordering & with direct access to 76 acres of protected Comeau Park, the property invites you to explore miles of woodland trails, open meadows, the Sawkill Stream and swimming hole. All less than a mile from Woodstock's vibrant town center. The home radiates a bright, airy open charm, creating a peaceful retreat that is equally suited for quiet relaxation or entertaining family and friends. A thoughtfully designed guest house provides exceptional flexibility, featuring two private ensuite bedrooms, a spacious sauna, and an outdoor shower that allows you to fully embrace the surrounding natural setting. The main residence beautifully combines Woodstock's artistic heritage with modern comfort. Once owned by Michael Lang, legendary founder of the 1969 Woodstock Festival, adding a rare and meaningful connection to the town's iconic past. The home has been extensively expanded and reimagined. The spacious open-concept great room with vaulted ceiling & walls of windows frame stunning views of the rolling meadow beyond. The main-level primary suite welcomes the morning sun, mountain views and features a newly renovated ensuite bath. Upstairs offers an additional 3 bedrooms, one ensuite and two baths offer ample space for family and guests. The property includes two separately deeded parcels. The existing residence sited on 3.71 acre parcel, while the adjoining 8.38-acre parcel (3-acre zoning) presents exciting possibilities for future development or even better preserving the land for ultimate privacy. The yard between the guest house and main residence is also ideally suited for a future swimming pool. Originally built in 1930 and extensively renovated and expanded, the home offers the character and soul of a Woodstock classic with the comfort, style, and functionality of modern construction. Whether you're seeking a full-time residence, a weekend escape, or a legacy property with room to grow, this remarkable estate captures the very best of Woodstock living.

Hidden from view at the end of a long private driveway, this extraordinary contemporary retreat is set on 12.69 meticulously maintained acres and offers what is arguably one of the most breathtaking settings in all of Windham. Panoramic mountain views, vibrant sunsets painted in shades of pink and orange, a sparkling private pond, and complete privacy create a setting that feels worlds away from the stresses of everyday life. Designed to embrace the surrounding landscape, the home features soaring vaulted ceilings and walls of glass that bring the spectacular views indoors. The spacious floor plan offers five bedrooms, three full bathrooms, one half bath, a dedicated ski and boot room, and a lower-level family room with wet bar for entertaining. Outdoor living is equally impressive with an expansive wraparound deck, covered front porch, stone patio, hot tub, outdoor shower, fire pit, and lush lawns surrounding the pond. Whether enjoying morning yoga on the deck, watching wildlife pass by, or gathering with friends beneath the stars, every inch of this property was designed to connect you with nature. A newer heated two-story barn offers endless possibilities and could easily be converted into a guest house, studio, or apartment. An attached two-car garage with storage above provides plenty of room for vehicles and gear. Located just minutes from skiing at Windham Mountain Club, dining, shopping, hiking trails, CD Lane Park, and the Windham Path, this remarkable property offers the perfect balance of seclusion and convenience. Owners may also choose to join the nearby High Ridge Club, which offers a pool, tennis, pickleball, and social amenities. Properties combining privacy, views, a pond, usable acreage, and proximity to Windham's year-round recreation are exceptionally rare. This is the mountain escape buyers dream about but seldom find. A 3D Walkthrough Tour is available in the digital Lookbook or by request.

There are ski homes, and then there are homes that truly define what ski-in/ski-out living is meant to be. Positioned directly on Windham Mountain Club's coveted White Way trail, this extraordinary timber-frame residence offers what is arguably the most desirable slope-side location on the mountain. No shuttles. No parking lots. No loading gear into the car. Simply step into your heated ski room, click into your bindings, and glide directly onto White Way. Built with timeless timber-peg construction, the home embraces the character and warmth of a classic mountain lodge while delivering the space and comfort expected in a luxury retreat. From the moment you step inside, you're welcomed by the calming aroma of natural wood--a subtle yet unmistakable reminder that you've escaped to the mountains. Rich wood-clad walls, soaring vaulted ceilings, and exposed beams create an atmosphere that is both grand and comforting, evoking the feeling of a private alpine retreat. Walls of glass flood the home with natural light while framing breathtaking mountain views in every season. The remarkable great room serves as the heart of the home, anchored by a magnificent wood-burning fireplace and framed by two stories of windows that bring the mountain directly indoors. During ski season, the ever-changing backdrop is nothing short of magical as cherished guests carve their way down the trail just beyond the glass. The open-concept floor plan was designed for gathering. The kitchen, dining, and living spaces flow seamlessly together, creating the perfect setting for après-ski entertaining and holiday weekends. A heated ski and boot room with brick flooring offers direct access to both the expansive deck and the trail, providing a dedicated space to store equipment, shed winter gear, and transition effortlessly from the slopes to the warmth of the home. The first floor features a private en-suite bedroom with direct deck access, ideal for guests. Upstairs, the primary suite occupies a privileged position of its own, complete with a walk-in closet, double vanities, a separate shower, and a soaking tub perfectly positioned to capture serene mountain views. An adjoining flex room offers endless possibilities such as a private office, fitness room, reading retreat, or additional sleeping space, allowing the entire second floor to function as an exclusive owner's sanctuary. The lower level accommodates additional bedrooms and baths, along with laundry and utility spaces, providing ample room for all your guests. A recently replaced roof adds peace of mind, while the quality craftsmanship and enduring beauty of the timber-frame construction ensure this home will remain as timeless as the mountain itself. Opportunities to own true ski-in/ski-out property at Windham Mountain Club are exceptionally rare. Opportunities to own one directly on White Way are rarer still. For those who dream of first tracks in the morning, unforgettable après-ski evenings by the fire, and a home that fully embraces the mountain lifestyle, this is the one. Drone video available on most sites showing the direct trail access. 3D virtual tour and floorplans available upon request.

Nestled among the trees and tucked back from the road, this immaculate Olivebridge retreat offers the kind of peace and privacy people move upstate for. Quiet, serene, and thoughtfully updated throughout, the property feels effortlessly welcoming from the moment you arrive. Inside, the home feels bright, comfortable, and incredibly well cared for. Sun pours through the windows, the wood stove adds a cozy touch in colder months, and the entire space has an easy, relaxed flow. Recent upgrades include a whole house generator, new driveway, and numerous improvements throughout, making the home feel completely move in ready. A small private deck off the primary bedroom overlooks the beautiful backyard, the perfect spot for slow mornings, evening wine, or listening to the trees move in the breeze. The expansive yard offers endless potential for a pool, gardens, or outdoor entertaining while still feeling incredibly private. One of the standout features of the property is the impressive 1,600 square foot two story barn. Whether you envision an art studio, workshop, music space, gym, guest quarters, or additional living space, it's the kind of building that immediately sparks inspiration. The charming front porch is tucked away from the street and surrounded by mature trees, making the entire property feel calm, secluded, and deeply connected to nature. Located just minutes from Kingston, Stone Ridge, Woodstock, and Accord, and close to favorites like Inness, Westwind Orchard, Arrowood Farms, the Ashokan Reservoir, and some of the best hiking and swimming holes in the Catskills. Roughly two hours from NYC, this is the kind of place that makes it easy to slow down and stay awhile.

Introducing Roaring Kill Retreat. Tucked among the trees on a secluded parcel, this light-filled 3-bedroom, 2-bath home is a modern Catskills escape where thoughtful, modern architecture meets handcrafted design. Abundant natural light pours through expansive windows, creating the feeling of a treehouse, while warm interiors balance clean lines with inviting character. The newly renovated kitchen is a standout, featuring custom cabinetry, ceramic checkerboard flooring, and a one-of-a-kind backsplash handcrafted by the homeowner, a local artist. Custom built-in cabinetry in the dining room adds warmth and functionality, while a wood-burning fireplace anchors the living space. A generous back deck and private balcony off the primary bedroom place you right in the forest canopy—perfect for entertaining, morning coffee, or simply taking in the peaceful surroundings. Partly wooded and exceptionally quiet, the property offers seasonal mountain views, nearby stream, and walkable access to nearby trailheads leading to some of the Catskills' most beloved hikes and waterfalls. Ideally situated between Plattekill Falls and Roaring Kill, it's also just 20 minutes from Colgate Lake and only 15 minutes to Hunter Mountain. Nature lovers will appreciate the property's remarkable wildlife, with more than 70 bird species observed from the home, including nesting Barred Owls. The surrounding woods and stream offer opportunities for mushroom foraging, while spring brings the unforgettable courtship displays of American Woodcocks nearby. Throughout the seasons, the landscape is constantly changing—from vibrant autumn foliage and mountains that glow red at sunset to soft pink evening skies created by the mountain elevation. In winter, Roaring Kill Retreat becomes an especially cozy escape, with snowy forest views best enjoyed beside the fire.

On one of the most beautiful roads between Woodstock and the Ashokan Reservoir, perched atop a mountain with epic, far-reaching verdant views, lies the striking Ohayo Mountain House. Built in the early 1930's as a peaceful Catskills retreat, this perfectly renovated and light-filled home sits on over eight acres, bordered by incredible wooded landscapes. The new gunite pool, bluestone lounge area, and poolhouse perfectly blend into the surrounding nature, and a long path meanders through a sweeping meadow of wildflowers and young evergreens. The Home: The home sits at the end of a long, fern-lined driveway and has a charming silhouette characteristic of regional mountain houses built in the early to mid-1900s. The original stone chimney is visible on the exterior, and an expansive front porch offers some of the most beautiful sunset views on the property. The interior is abundantly peaceful and thoughtfully envisioned, with walls of original historic windows looking out on lush greenery, light, wide-plank wood floors with delicate graining, wood beams, terracotta-tiled baths, and exquisitely curated fixtures and hardware. The great room has a powerful woodstove, inset into the circa 1930s stone fireplace. There are two bedrooms on the second floor, and two full baths in the house. A large office/utility/family room is on the garden floor, with beautiful interior stonework and its own exit to a covered exterior porch. The Grounds: The Ohayo Mountain House's eight-acre grounds are truly exceptional. The mix of mid-density forest, open meadow, gardens, long stone walls, and walking paths is delightful, and all just minutes away from the village of Woodstock. The large pool and its accompanying poolhouse are tucked into a perfect nook within the landscape. There are multiple places to entertain or enjoy long summer dinners, from the bluestone terrace, to the covered porch, to the breezeway of the pool house. The Surroundings: The property is surrounded on three sides by over 5,000 acres of NY State protected land, and is located five minutes from Woodstock, 20 minutes from Kingston, 30 minutes from Rhinebeck, and just over 2 hours from New York City. There are endless nearby options for dinner, like Silvia's, Nirvana, or Good Night, plenty of outdoor play from the more rigorous - games at the Woodstock Tennis Club - to the more wild - swimming at the Big Deep - to the completely invigorating - hiking around the Ashokan Reservoir. Incredible produce and groceries are easy to access, whether you are filling a basket with local goodies from the Wednesday farmers market, grabbing the best bagels from Moonrise, or stocking up the pantry at Sunflower Market.

The Elka Park Studio-Build, Create, Expand. Tucked just beyond the reach of the everyday, in the quiet pocket of Elka Park, this property offers something increasingly rare — a finished, thoughtfully renovated guest house/art studio paired with the infrastructure to grow. Set on two acres along sought-after Platte Clove Road, the groundwork has already been done. A newly improved septic system sized for a four-bedroom home, in-ground electric, drilled well, and whole-house generator allow for a seamless transition to your future build. The existing structure lives beautifully in the meantime — a light-filled studio with vaulted ceilings, a lofted living space, and a wood-burning stove that anchors it all. Below, a one-car garage and flexible workspace lend themselves to creative use or quiet retreat. What sets this property apart is its position. A south-facing orientation captures sweeping mountain views and steady light throughout the day — the kind of setting that draws artists, designers, and those looking to disconnect without disappearing entirely. From your door, access some of the Catskills’ most iconic outdoor destinations, including Kaaterskill Falls and Platte Clove Preserve, with skiing at Hunter Mountain just minutes away. The villages of Woodstock and Tannersville are a short drive for dining, galleries, and everyday ease. A rare opportunity to own a small, meaningful piece of Elka Park — with the hard work complete, and the vision still yours to define.

Architect-Designed Modern Retreat with Unparalleled Views Over Woodstock! Perched high above the Town of Woodstock, this rare and exceptional home offers a front-row seat to breathtaking panoramic views that stretch from the mountains to the Ashokan Reservoir. Designed by noted architect Les Walker, this contemporary residence evokes the magic of living in a luxurious treehouse--where every room is immersed in natural light and dramatic scenery. Wake to stunning sunrises and unwind to radiant sunsets from the comfort of your open floor plan living space, where a soaring floor-to-ceiling bluestone fireplace anchors the heart of the home. Expansive windows line the entire south-facing rear of the house, bringing the outdoors in and framing unforgettable vistas year-round. Enjoy seamless indoor-outdoor living with two spacious decks--one screened for breezy summer nights, and one open for sun-soaked afternoons. The chef's kitchen flows effortlessly into the main living area, ideal for entertaining or quiet evenings by the fire. The main floor primary ensuite features a walk-in closet, built-in shelving, and serene views, while two flexible-use rooms offer space for a home office, media room, or guest quarters. Smart thermostats add modern comfort. Step outside to your private bluestone patio with a heated saline inground pool, outdoor kitchen, and firepit--your personal oasis nestled in the Catskills. A finished studio space above the 440 sq. ft. garage offers even more options for creativity or guests. Additional features include solar panels with battery pack, a circular drive for easy access, and meticulous attention to detail throughout. A truly rare offering--private, peaceful, and just minutes to the vibrant arts, dining, and community of Woodstock. A 3D Walkthrough Tour is available in the digital Lookbook or by request.

A Rare Opportunity in the Heart of Woodstock. Own a remarkable piece of Woodstock history. Once the site of the Woodstock Lodge and The Pinecrest, this storied property invites you to step back in time while envisioning its next chapter. Set on 6.5 acres of scenic land with a mix of cleared grounds, wooded trails, and a seasonal stream, this property offers a rare combination of privacy and convenience a short distance from the vibrant village center with its shops, restaurants, and year-round cultural events. The property includes nine structures plus one foundation, a workshop, and an in-ground pool. Utilities, wells, and septic exist on the property. Property and all structures, infrastructure being sold as-is/where-is. Currently zoned R3 Residential with potential for residential redevelopment and possible subdivision, Buyer to due diligence on future use/configuration.

Set at the end of a long, private driveway, Eagle Ridge Estate sits high above the Ashokan Reservoir on over nine secluded acres, offering rare peace, unbroken mountain views, and the quiet grace of a home rooted deeply in history. Surrounded by century-old lilacs and a broad open lawn, this 5-bedroom, 3-bathroom residence spans 3,566 square feet across three floors, with timeless design and intentional craftsmanship in every room. Inside, the home unfolds with warmth and authenticityfrom the original red oak trim and pocket doors to the built-in glass cabinetry, cast iron radiators, and the beautiful maple floors underfoot, to the 9-foot ceilings throughout. The main level offers a gracious layout: formal living and dining rooms, centered by a large woodburning stone fireplace, a bright sunroom-style breakfast room, and a spacious kitchen that overlooks the backyard and pool. The kitchen and baths have been updated over time, yet remain true to the character of the home, including a clawfoot tub and classic tile work. An additional room on the lower level, along with a foyer, provides flexibility for an office, playroom, or creative studio. The beautiful glass oak trimmed French doors lead out to the stone patio and views of the Catskills and Reservoir, offering the perfect blend of indoor and outdoor living. On the top floor, a fully windowed observatory-style space offers 360-degree viewsa truly special setting once used by the home's original owner, J. Waldo Smith, to oversee the construction of the Ashokan Reservoir as eight towns were relocated to make way for one of the most important infrastructure projects in New York's history. Originally constructed by Smith himselfChief Engineer of the Ashokan Reservoirthe home is built from locally quarried Rosendale stone, chosen for its strength and permanence. After the Smith family, the home became part of the Chase family estate, where actor Chevy Chase spent part of his youthadding another layer of cultural legacy to this historic property. Outside, the inground, heated saltwater pool, stone patios, and rolling backyard lawn are ideal for summer gatherings and quiet moments alike. A two-car garage, buried electric lines, a battery back-up system, a standby generator, and a new Buderus boiler ensure the property functions as beautifully as it looks. The high-ceiling basement provides storage and future potential, while mature trees and mountain air frame the entire estate in calm. For those seeking a compound or expanded retreat, the adjacent home is also available for purchase. Inquire for more details.