Courtesy: Coldwell Banker Village Green
845-679-2255
A rare opportunity just minutes from the heart of historic Woodstock, this exceptional country compound pairs the timeless character of a beautifully updated farmhouse with the privacy and tranquility of an estate-like setting. A long private drive unfolds through peaceful, park-like grounds where meadow, mature woods, gardens, and abundant nature create a remarkable sense of seclusion so close to town. At the center of it all, the classic farmhouse has been thoughtfully transformed for modern living while preserving the warmth and authenticity that make a Woodstock home so distinctive. An expansive wraparound porch and deck invite long afternoons outdoors, elegant entertaining, and evenings beneath the stars from the hot tub. Inside, natural light pours through generous windows and skylights, illuminating an open and welcoming interior where a spacious living room flows effortlessly into the dining area and striking gourmet kitchen, anchored by a dramatic stone island. A soaring vaulted family room overlooks the meadow and woods and features a woodstove and direct access to the deck, creating an extraordinary gathering space—or the possibility of a main-level primary suite. A separate den offers an ideal home office or studio, while a gym/yoga room, laundry room and full bath add versatility to the first floor. Upstairs, three bedrooms and another full bath retain the farmhouse's old-world charm, including a serene and generously proportioned primary bedroom and a second bedroom with its own inviting nook. Adding another dimension to this extraordinary property is a beautifully maintained storybook cottage, privately positioned toward the front of the grounds with its own parking, patio, and yard. Currently licensed for Airbnb use, the cottage offers an appealing opportunity for short-term rental income while remaining equally suited as an elegant guesthouse, private retreat, or longer-term residence. Its charming two-story interior features a comfortable living room, eat-in kitchen, full bath, and two upstairs bedrooms, creating a completely independent destination within the property. With hiking, nature preserves, and the Catskills landscape nearby—and the galleries, restaurants, shops, music, and cultural life of Woodstock only a few miles away—this is a particularly rare convergence of location, privacy, architectural character, and flexibility. Whether envisioned as a refined full-time residence, an exceptional weekend escape, or a private country compound with a valuable guest and rental component, this turnkey property captures the essence of elevated Woodstock living: a classic farmhouse reimagined for today, surrounded by natural beauty, with space to retreat, gather, entertain, and simply enjoy an extraordinary place to call home. A 3D Walkthrough Tour is available in the digital Lookbook or by request.
Courtesy: Coldwell Banker Village Green
845-679-2255
A rare opportunity just minutes from the heart of historic Woodstock, this exceptional country compound pairs the timeless character of a beautifully updated farmhouse with the privacy and tranquility of an estate-like setting. A long private drive unfolds through peaceful, park-like grounds where meadow, mature woods, gardens, and abundant nature create a remarkable sense of seclusion so close to town. At the center of it all, the classic farmhouse has been thoughtfully transformed for modern living while preserving the warmth and authenticity that make a Woodstock home so distinctive. An expansive wraparound porch and deck invite long afternoons outdoors, elegant entertaining, and evenings beneath the stars from the hot tub. Inside, natural light pours through generous windows and skylights, illuminating an open and welcoming interior where a spacious living room flows effortlessly into the dining area and striking gourmet kitchen, anchored by a dramatic stone island. A soaring vaulted living room overlooks the meadow and woods and features a woodstove and direct access to the deck, creating an extraordinary gathering space - or the possibility of a main-level primary suite. A separate den offers an ideal home office or studio, while a gym/yoga room, laundry room and full bath add versatility to the first floor. Upstairs, three bedrooms and another full bath retain the farmhouse's old-world charm, including a serene and generously proportioned primary bedroom and a second bedroom with its own inviting nook. Adding another dimension to this extraordinary property is a beautifully maintained storybook cottage, privately positioned toward the front of the grounds with its own parking, patio, and yard. Currently licensed for Airbnb use, the cottage offers an appealing opportunity for short-term rental income while remaining equally suited as an elegant guesthouse, private retreat, or longer-term residence. Its charming two-story interior features a comfortable living room, eat-in kitchen, full bath, and two upstairs bedrooms, creating a completely independent destination within the property. With hiking, nature preserves, and the Catskills landscape nearby - and the galleries, restaurants, shops, music, and cultural life of Woodstock only a few miles away - this is a particularly rare convergence of location, privacy, architectural character, and flexibility. Whether envisioned as a refined full-time residence, an exceptional weekend escape, or a private country compound with a valuable guest and rental component, this turnkey property captures the essence of elevated Woodstock living: a classic farmhouse reimagined for today, surrounded by natural beauty, with space to retreat, gather, entertain, and simply enjoy an extraordinary place to call home. A 3D Walkthrough Tour is available in the digital Lookbook or by request.
Courtesy: Halter Associates Realty
845-679-2010
One of Woodstock's Original Handmade homes tucked away on almost 3 private acres at the end of a dead end lane. This 3 Bd/ 1.5 Ba home minutes to the center of Woodstock is the quintessential country retreat. Blending in with the natural Hudson Valley landscape this cedar and bluestone sided home leans into Woodstocks rich history of artists and builders utilizing their surroundings for sourcing materials and inspiration. This home is comprised of three floors with original hardwood floors and tile throughout.. Walking into the kitchen/ dining ares with exposed beams and original open fire cooking fireplace (now decommissioned). The country kitchen has original solid wood cabinets, all new stainless steel appliances ( refridgerator and stove on their way) and a wall full of windows with one large picture window bringing the Catskill forest in to your little sanctuary. Walk out the kitchen door to the back bluestone patio for dining al fresco. A full bathroom with original, retro feel tile and cast iron tub on main floor. Upstairs is a gracious living room with cathedral ceilings, exposed hand hewn beams and brick fireplace perfect to lounge by on winter days and offering an organic secondary heat source throughout this sweet, cozy home. Bedroom is opened up to main living area. Walls of windows bathe this room with natural light and offer views only of trees and sky all around you. The bottom floor offers a bedroom and sitting area and half bath. Outside are bluestone stairs to meander the grounds and take in the beautiful woods that surround this private haven. Situated in the coveted Bearsville hamlet, this lovely home is minutes to the legendary Bearsville Theater, Woodstock Byrdcliffe Guild + Arts Colony and the center of Woodstock with it's cafes, top notch eateries and world renowned music venues. For outdoor enthusiasts Overlook Mountain, extensive trails throughout the Catskill Mountains and the Rail Trail are all a stone's throw away. This home makes the perfect retreat but also lends itself to expansion. As it is 1.5 acre zoning and it sits on almost 3 acres it has the capability to have a main home and accessory dwelling on this parcel so there is room for expanding for a compound feel ( buyer to confirm with Woodstock Building Dept). Enjoy this classic home as is and expand over time . It is rare to find parcels with this kind of potential so privately sited yet minutes to Woodstock. .
Courtesy: Serhant LLC
646-480-7668
Set on one of Woodstock's most coveted country roads, this classic home offers the rare combination of timeless charm, privacy, and an exceptional location. Just moments from the heart of Woodstock, yet quietly removed, Cooper Lake Road is known for its scenic beauty, peaceful surroundings, and idyllic walks to nearby Cooper Lake. Originally portion of the house possibly dates to 1875 with various additions added over the years, this 3-bedroom, 2.5-bath Colonial retains its period character while offering the comfort and ease of modern living. Tucked back off of the road, a private drive leads to the home, set on a generous 3.27-acre corner parcel with frontage extending to Rose Lane--survey available. Inside, the home unfolds with warmth and versatility. A welcoming den with built-ins and a powder room creates the perfect space for a home office or tv room. The living room is in part of the original house and features vaulted, beamed ceilings, a striking stone fireplace with propane insert, and walls of windows. The kitchen is conveniently set between the attached garage and breakfast room that opens out onto a stone patio. A formal dining room is also off the kitchen. Upstairs, two bedrooms share a full bath, while the spacious and grand primary suite enjoys its own private wing, complete with built-ins and an ensuite bathroom. This is a rare opportunity to own a truly special home in one of Woodstock's premier locations--where quiet country roads, natural beauty, and proximity to town come together seamlessly.
Courtesy: Coldwell Banker Village Green
845-679-2255
Tucked at the end of a private road just minutes from Woodstock, this exceptional five-bedroom, five-bath residence offers an uncommon combination of privacy, generous scale, and scenic charm. Set on approximately three acres and bordered by a year-round stream, the 3,722 square foot home feels wonderfully secluded while remaining close to the restaurants, shops, galleries, and creative energy of Woodstock. Originally built in 1952, the home has been carefully expanded, renovated, and extensively upgraded over the years. Recent improvements include a newly added en-suite bathroom for the primary bedroom, along with numerous updates throughout. The result is a sophisticated yet comfortable home designed for year-round living. Furnishings and decor are also available for purchase, making the transition remarkably seamless. Inside, generous windows and an open layout bring in the surrounding landscape. The high-end kitchen flows into the dining and living areas, creating an easy setting for both usual life and entertaining. Warm materials, a fireplace, and carefully designed gathering spaces give the expansive interiors a welcoming sense of intimacy. The primary suite overlooks the stream and opens to a private deck. A large walk-in closet and newly added en suite bathroom complete this calm retreat, while the sound of flowing water provides a natural soundtrack throughout the day. One of the property's defining features is its light-filled indoor pool room. Wide windows surround a heated gunite saltwater pool, creating a private place to swim and unwind in every season. A top-of-the-line Harvia sauna completes the wellness experience. A separate outbuilding extends the possibilities, with its own private deck and fire pit. Use it as an art studio, yoga space, home office, guest retreat, or simply a place to escape for a few quiet hours. Outside, multiple decks and gathering areas overlook the stream and koi pond, creating natural spaces for dining, entertaining, and enjoying the landscape. Mature grounds provide room for gardening and outdoor recreation, while the adjacent woods and water bring an air of peace to every season. This property is built around the pleasures of everyday life. Swim in the pool, retreat to the sauna, work from the studio, gather around the fire, or sit beside the stream and listen to the water. With substantial living space, exceptional amenities, a private setting, and proximity to Woodstock, Streamside Sanctuary offers an unusually complete Catskills retreat. Whether used as a full-time residence, weekend home, or private getaway, it's designed to be enjoyed from the moment you arrive.
Courtesy: Halter Associates Realty
845-679-2010
Escape to the woods in an Iconic Woodstock location! Tucked away on a quiet dead-end road, this eclectic one-bedroom cabin sits on just over 3 wooded acres filled with a beautiful mix of mature, towering trees. At the rear boundary is a mountainside stream. Full of character and rustic charm, the contemporary cabin features a large deck nestled among the trees--perfect for morning coffee, afternoon lounging, or summer evenings outdoors. A woodstove adds cozy winter comfort, while a separate shed provides useful storage. The cabin needs some work, but the setting is special and the location offers exciting potential for expansion. A great opportunity to create your own private Woodstock retreat in a highly desirable location at a very reasonable price.
Courtesy: Century 21 Alliance Rlty Group
845-297-4700
There are homes that ask you to compromise, and then there are homes that ask you to dream. Set against a backdrop of sweeping mountain views, this is a rare opportunity to create something that’s unmistakably yours. The hardest work has already been done. What’s left is the part that reflects your style, your vision, and the way you want to live. Picture slow mornings with coffee overlooking the mountains, evenings spent watching the seasons change, and a home finished exactly the way you’ve always imagined—not someone else’s choices, but your own. Whether your vision includes warm natural finishes, clean modern lines, or a timeless mountain retreat, this property is ready for the next chapter. In a market where finding the right location is nearly impossible, opportunities like this don’t come along often. For generations, Bearsville and neighboring Woodstock have drawn musicians, painters, writers, makers, and free spirits seeking inspiration, community, and a different pace of life. Here, you’re close enough to enjoy the galleries, live music, cafés, and creative energy that define the area, yet far enough away to hear little more than the wind through the trees and the sounds of nature. Bring your imagination, your contractor, and your plans. The canvas is waiting.
Courtesy: Hudson Valley Real Estate Brok
845-853-8250
Tucked away on a quiet private road in coveted Bearsville, this light-filled contemporary sanctuary offers 1.87 serene acres and the ultimate Hudson Valley indoor-outdoor lifestyle. Perfectly positioned to capture sweeping mountain vistas, the home delivers an effortless blend of mid-century character and modern luxury. Step inside to an expansive main living area anchored by a whitewashed brick fireplace with a broad bluestone hearth. Soaring vaulted ceilings lined in natural wood accents, oversized skylights, and warm oak hardwood floors create an open, airy atmosphere wrapped in forest views. The living room flows seamlessly into a sunlit dining area and an eat-in kitchen featuring custom seafoam cabinetry, glass-front uppers, sleek black tile backsplash, stainless steel appliances, and a secondary prep sink--ideal for hosting. Just off the kitchen sits a charming screened 3-season porch with painted exposed beams, creating an effortless transition to outdoor dining. A cozy breakfast nook framed by a bay window offers another sunny spot for morning coffee. All 3 bedrooms are conveniently situated on the main level. The main-floor primary bedroom features its own en-suite bathroom, while two additional guest bedrooms are serviced by a second full main-level bath. Upstairs, an open flex loft studio awaits. Featuring vaulted wood ceilings, skylights, wide-plank wood flooring, built-in display shelving, and a 3rd full bathroom, this open-concept space is ideal for an artist studio, home office, or secondary lounge. Glass doors open directly onto a 17'x14' walkout roof terrace framing panoramic mountain views and forest canopy. The full basement boasts high ceilings and impressive footprint potential--offering a prime opportunity for a future buyer to finish the space for additional living square footage, a home theater, or a gym. Outdoor living is truly second to none. The home boasts three brand-new decks with modern cable wire railings--including the entry deck, a dedicated hot tub deck nestled into the trees, and the upper roof terrace. Follow stone pathways through the grounds down to the crown jewel of the property: a gated, in-ground swimming pool surrounded by an expansive paver patio, diving board, and mature landscaping. Complete with multi-zone ductless cooling, new roof, an attached two-car garage, storage shed, a paved driveway with a basketball court area, and total seclusion on a private road while remaining just minutes from downtown Woodstock's dining, shops, and arts scene, 15 Upper West Ohayo Road is a turn-key year-round home or luxury seasonal escape.
Courtesy: BHHS Hudson Valley Properties
845-679-0006
Wend up your forested driveway to this idyllic piece of paradise -- 12 secluded acres, just minutes from Woodstock Village. The current owner/architect/builder designed this uniquely curated home and its surroundings to create the penultimate natural setting. As the house is revealed through the trees, a mirror image is reflected in the 13' deep, swimmable, mini-lake. BREATHE! That's the perfect response to this awe-inspiring locale. 6 springs feed this silky clear, ''Catskill clean'' water feature; kept pristine by 2 aeration systems providing clear, oxygenated water for this bass-stocked body. There's a dock and fountain, and the water's edge is peppered with locally sourced boulders providing numerous places for diving, sun bathing, and meditating on the picturesque landscape. All this is just a few hand-picked, stone steps from a splendid 2 BR, 2 bath, Frank Lloyd Wright inspired, prairie-style home capped by an English style Tudor chimney featuring superlative brick accents. The curved, blue stone entry walkway gives pause for contemplation as you pass carefully placed perennials, a field of ferns, and majestic birch, maple, and pine trees. Poetry at every turn! Subtle architected details include a concrete plinth-to-window sill foundation and extended overhangs, creating calm and stability to an open, light-filled life. The house is surrounded by extraordinary blue stone walkways and three patios (one covered) all revealing views of mountains, water, and sky. Upon entering you'll experience this home's elegant simplicity. The tiled foyer features a hand-crafted wooden light fixture and a Wright-inspired stair post--details that elevate the home's design from the moment you step inside. The living room is surrounded by views; north to Indian Point and west for exquisite mountain sunsets. The natural world beckons you out every picture window and door. On a winter's day appreciate the outside while reading beside a centrally located and uniquely designed brick fireplace. The kitchen has rose granite counters and birds-eye maple and cherry cabinetry--and a large pantry. Entertaining is easy with a dining room that provides space for every gracious event; be it for 4, 8, 16, or 20 guests! The lake and views continually serve as a backdrop as you sit with refreshments and chat with guests; or step out onto the open blue stone pergola and connect with sun, moon, and nature at any hour, in any season. A 6-zone irrigation system (on timers) effortlessly maintains the deer resistant shrubs, grasses, fields of ferns, including the raised bed and fully-fenced vegetable garden. Upstairs is the primary bedroom, a refuge for sweet dreams under the canopy of an angular roof line. A large cushioned window seat becomes a haven for intimate moments gazing into the distant mountain views just past the mini-lake. A second sky-lit bedroom shares a stylish bathroom that has a custom wood vanity, cast iron claw foot tub, and a reclaimed Carrara marble counter top. Plenty of closets and built-ins make nesting here easy. Add to all this a studio building that provides ample space for an office, artists haven/workspace, gym, or play area. Unique details, like a massive fan shaped skylight, carry over to this structure as well, giving it a lofty and alluring ambiance. There's storage galore, and space to spread out to follow your passions. The current owner uses two loft storage spaces for her artwork. This rare Woodstock parcel has plenty of room for an addition, pool, or guest house (with town approval), and is a natural palette for you to create your own compound if desired. You might never want to leave. However, you're close to skiing, hiking, shopping, great restaurants, and one of the grooviest towns in America! Wander and hike your own Catskill Park. A pleasure to see and show. Appointment required.
Courtesy: William Pitt Sothebys Int Rlty
845-677-5512
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.
Courtesy: Halter Associates Realty
845-331-3110
Come and see this cute-as-a-button, circa 1950 brick cape on Elting Lane, one of Woodstock's most enchanting roads! This easy-to-manage home on just shy of an acre, boasts woodland surroundings plus seasonal meadow and mountain views and fruit trees. The main floor features a light flooded living room with fireplace, an efficient kitchen with adjacent dining area with double glass doors leading onto the ample patio. Two bedrooms and full bath complete this level with hardwood floors throughout. The second level has a loft space, ample dry storage area and bath perfect for office/studio and sleeping space. The large dry basement features laundry, mechanicals (including new boiler), and lot of storage but could be used in many ways including craft, shop, studio, play or workout area. Fenced in garden is ready for its next planting. Less than 10 minutes to the village of Woodstock, Cooper Lake and all things Catskills including hiking, skiing and walking rail trails. Uptown Kingston and the NYS Thruway is a mere 20 minutes away. Ample parking plus a one-car, detached garage with room for storage just steps from the main house. Don't miss this sweet 1500 square foot gem. The possibilities are absolutely endless!
Courtesy: HEATHER CRONER RE-SOTHEBY'S ML
Four House Compound on 25 Acres. Welcome to this extraordinary property nestled in the heart of Woodstock, NY, which holds a rich history as it is believed to be the first farm in the Valley. Originally established as the Shultis sheep farm in 1753 this expansive 25-acre estate offers a unique blend of heritage and countryside lifestyle. With its charming farmhouse, magnificent converted barn, historic schoolhouse with two full residences, and a cozy mid-century house, this property presents a rare opportunity to own a piece of Woodstock's past.The farmhouse, steeped in history, exudes rustic charm and offers a warm and inviting atmosphere. With its classic design and timeless appeal, this residence features beautiful wood floors, beamed high ceilings and a cozy fireplace. The spacious layout provides ample room for comfortable living, while the surrounding natural beauty creates a sense of tranquility. Adjacent to the farmhouse, the converted barn stands as a testament to architectural excellence. This expansive space offers endless possibilities, whether you envision it as a studio, workshop, or a grand entertainment area. The barn's soaring ceilings, exposed wooden beams, incredible wide plank original floors and abundant natural light create an awe-inspiring ambiance that is sure to impress.Adding to the property's allure, the historic schoolhouse has been thoughtfully transformed into two separate residences. This unique feature presents an excellent opportunity for rental income or accommodating guests. Each offers its own distinct charm and character, providing a comfortable and private living space. The mid-century house, with its two bedrooms, offers a modern retreat amidst the natural beauty of Woodstock. This cozy dwelling provides a perfect blend of comfort and simplicity, allowing residents to unwind and enjoy the peaceful surroundings.Nature enthusiasts will appreciate the property's diverse landscape, including several open fields and a meandering stream. These features provide ample space for gardening, farming, or raising animals, allowing you to embrace a sustainable and self-sufficient lifestyle.Conveniently located just seven minutes away from the vibrant village of Woodstock, residents will enjoy easy access to a plethora of shops, restaurants, and cultural attractions. Whether you're seeking a leisurely stroll through the charming streets or indulging in the local culinary scene, the village offers a vibrant and eclectic experience.
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Bearsville is located in New York. Bearsville, New York has a population of 672. Bearsville is less family-centric than the surrounding county with 16.72% of the households containing married families with children. The county average for households married with children is 25.39%.
The median household income in Bearsville, New York is $101,724. The median household income for the surrounding county is $71,040 compared to the national median of $69,021. The median age of people living in Bearsville is 61.4 years.
The average high temperature in July is 82.5 degrees, with an average low temperature in January of 14.8 degrees. The average rainfall is approximately 49.6 inches per year, with 56.9 inches of snow per year.
