Courtesy: Callicoon Real Estate LLC
845-887-4400
Here is just the place to escape to when the city life gets to be too much! Charming 1930's bungalow style home with 4+ bedrooms, a full bath, living room and spacious kitchen. The front entrance leads from a wonderful enclosed porch to the living room. Or enter over the back stairs onto the deck and into the mudroom. Perfect to keep those little boots that little people need to play outside or splash by the creek that will keep them occupied all day! Enjoy evenings around the fire pit with the soothing music coming from the creek, or from Wednesday evening concerts by the Callicoon Center Band just a short walk away. Grab a book and enjoy some solitude in the creekside cabin. Americana is the feeling - and it is a good feeling! Dine at Callicoon Hills's Conover Club or visit the many other beautiful little hamlets you have heard so much about - Callicoon, Jeffersonville, Roscoe. The North Branch Cider Mill is back! Life does not get much better!
Courtesy: Anatole House LLC
845-943-4177
Built in 2023 and set on 2.87 acres with a mountain view, this 3-bedroom, 2-bath home offers the benefits of new construction without the work that typically follows. Since completion, the property has been professionally graded and landscaped, evergreen trees have been planted, and a hot tub has been added, creating an established setting from day one. Inside, 1,370 square feet of bright, open living space features vaulted ceilings, oversized windows, wide-plank flooring, a wood-burning fireplace, and a spacious kitchen with Samsung appliances and a large center island. Sliding doors open to an elevated deck overlooking the backyard and surrounding hills. The primary suite includes a freestanding soaking tub, glass-enclosed shower and a large picture window. A full 1,370-square-foot walkout unfinished basement offers excellent potential for future living space, recreation, or storage. Just 3 minutes from Jeffersonville, with easy access to Sullivan Sundries, Ratty Books, Bloom Coffee, local dining, and the Delaware River, the home is equally suited as a full-time residence, weekend getaway, or investment property. With approximately $95,000 in Airbnb revenue generated since 2023 and furnishings available separately, it offers a rare turnkey opportunity in one of Sullivan County's most desirable locations. Under 2 hours to NYC.
Courtesy: Malek Properties
845-583-6333
Welcome to “Long Farm”. Begging to be the backdrop of your most memorable moments, this newly constructed custom designed home is your country house dream come true. Perfectly set back off a quiet country road and perched on a knoll on 5+ acres with fabulous meadow and mountain views from nearly every room, this one checks all the boxes. 4 BR’s 3.5 BA’s, primary bedroom with gorgeous bath and walk in closet and sliders to outdoor deck is on main level and a second suite plus two more bedrooms occupy the upstairs. Lots of glass lets in an abundance of natural light, while soaring cedar-lined ceilings, wide plank white oak flooring and a really cool suspended Aurora Aether wood burning fireplace set the tone with a cozy and classy vibe. The amazing open plan with island kitchen is perfectly appointed for entertaining friends and family. Sliders off the dining area give way to an outdoor space that will never disappoint. Taking advantage of the gorgeous view and glorious sunsets, there is an outdoor kitchen, fire pit and shower which are just a few of the extras this talented developer has added to this home. Full basement offers an additional 1200 SF with 10’ ceilings. Long Farm is a new development of specially curated homes with fresh clean lines, warm wood accents, locally sourced materials and quality workmanship. Amenities are yours to choose and may include a clubhouse, gym, walking trails, pool, tennis and more. Near to area attractions including the Delaware River, Bethel Woods, breweries, cideries, dining, skiing, lakes, hiking trails, and everything the Sullivan County Catskills has to offer. More Amazing lots and plans available to suit your personality and needs. Additional Information: Amenities:Guest Quarters,Storage,
Courtesy: Malek Properties, Inc.
845-583-6333
Welcome to ''Long Farm''. Begging to be the backdrop of your most memorable moments, this newly constructed custom designed home is your country house dream come true. Perfectly set back off a quiet country road and perched on a knoll on 5+ acres with fabulous meadow and mountain views from nearly every room, this one checks all the boxes. 4 BR's 3.5 BA's, primary bedroom with gorgeous bath and walk in closet and sliders to outdoor deck is on main level and a second suite plus two more bedrooms occupy the upstairs. Lots of glass lets in an abundance of natural light, while soaring cedar-lined ceilings, wide plank white oak flooring and a really cool suspended Aurora Aether wood burning fireplace set the tone with a cozy and classy vibe. The amazing open plan with island kitchen is perfectly appointed for entertaining friends and family. Sliders off the dining area give way to an outdoor space that will never disappoint. Taking advantage of the gorgeous view and glorious sunsets, there is an outdoor kitchen, fire pit and shower which are just a few of the extras this talented developer has added to this home. Full basement offers an additional 1200 SF with 10' ceilings. Long Farm is a new development of specially curated homes with fresh clean lines, warm wood accents, locally sourced materials and quality workmanship. Amenities are yours to choose and may include a clubhouse, gym, walking trails, pool, tennis and more. Near to area attractions including the Delaware River, Bethel Woods, breweries, cideries, dining, skiing, lakes, hiking trails, and everything the Sullivan County Catskills has to offer. More Amazing lots and plans available to suit your personality and needs.
Courtesy: Century 21 Geba Realty
845-856-6629
Some streets just have a feeling, and Chapel Street is one of them. Towering shade trees and classic homes line this beloved street in the Village of Jeffersonville, welcoming you to a timeless Victorian ready for its next chapter. Step inside to discover four bedrooms, two full bathrooms, and beautiful hardwood floors that speak to the craftsmanship of another era. Every room offers the opportunity to blend historic charm with your own personal style, creating a home that's uniquely yours. Outside, the magic continues. Gather around the outdoor fireplace on crisp Catskills evenings, host friends in the spacious backyard, or simply enjoy the peaceful surroundings beneath the mature trees that make this property so special. Living here means more than owning a beautiful home; it's becoming part of one of Sullivan County's most vibrant village communities. Visit local craft fairs, shops, and community events, then spend your weekends exploring the mountains, lakes, farmers' markets, and endless outdoor adventures that make the Catskills such a treasured place to call home. If you've been searching for character, charm, and the chance to create something truly special, your story begins here on Chapel Street.
Courtesy: Century 21 Country Realty
845-791-5280
Enjoy space, scenery, and easy access to the best of the Sullivan Catskills with this well-maintained 3-bedroom, 2-bath mobile home set on 4.42 acres. The home features a large living room, comfortable layout, and plenty of room to relax indoors or out. A spacious deck accented by natural wood and stone invites you to take in the beautiful views and enjoy quiet mornings, outdoor meals, or evenings surrounded by nature. With over four acres, the property offers ample space for gardening, recreation, pets, gatherings, or simply enjoying the peaceful setting. Outdoor enthusiasts will love the location, with convenient access to the Delaware River area, Callicoon, and Roscoe. Nearby attractions include fly fishing, river activities, hiking, scenic drives, local shops, and a variety of well-loved restaurants throughout the region. Whether you are looking for a full-time residence, weekend getaway, or Catskills-area retreat, this property offers the combination of usable acreage, natural beauty, and proximity to recreation that makes country living so appealing.
Courtesy: Malek Properties
845-583-6333
Welcome to Stonegate House. Set back from the road at the end of a strikingly gated driveway, this delightful home is perched on a knoll overlooking its own private pond. The spacious interior offers that sought-after chalet vibe with a modern flair. Open and airy, with expansive windows that showcase the surrounding scenery, this property certainly checks all the boxes for the discerning buyer. Natural light floods the interior by day, while the oversized windows provide dazzling celestial views of the stars by night. The living and dining areas are anchored by a lovely gas fireplace, enhanced by a striking floor-to-ceiling porcelain tile accent handcrafted in Spain. Two glass sliders beckon you outdoors to a generous patio overlooking the peaceful pond and cozy fire pit; perfect for barbecues, entertaining, or simply relaxing. The sleek and stylish island kitchen features a double sink, quartz countertops, a spacious pantry closet, and Frigidaire stainless steel appliances, including a full-size convection oven. It offers everything needed to comfortably prepare your favorite meals. With two en-suite bedrooms, you have your choice of a primary suite on either the main level or the second floor. Upstairs, French doors lead to the oversized en-suite bedroom which opens to a sizable loft area that is ideal for a home office, reading nook, or flex space. The main-level primary suite offers access to a private patio with a separate entrance, a walk-in closet, and a luxurious bath. The second level primary or junior suite features a dreamy soaking tub and its own fireplace for added ambiance. Set on 3.2 acres, this home boasts more than 3,700 square feet of living space, including over 1,300 square feet in the lower level. The finished lower level with double-door walkout access provides exceptional additional living space perfect for a game room, home theater, bar, hobby space, fitness area, or whatever suits your lifestyle. A centrally located laundry closet on the main level adds convenience and additional amenities include a universal electric vehicle charger, excellent satellite Internet service, and a whole house generator. Upscale finishes include graphite maple flooring throughout the main and second levels, fully tiled bathrooms, frosted glass-paneled doors, recessed LED lighting, new luxury vinyl plank flooring in the lower level, and much more. Built in 2024, the home offers the peace of mind that comes with all-new systems, including mini-split units installed last year. Nestled in a desirable rural area near to Livingston Manor, Roscoe, Callicoon, farms, rivers, breweries, shopping, dining and all the wonderful and exciting activities the Sullivan County Catskills has to offer.
Courtesy: Country House Realty Inc
845-397-2590
Let country roads take you home to this charming retreat, set on a beautifully private parcel. Tucked deep into the rolling hills of Jeffersonville, this well-maintained and recently updated, custom-built 2004 home delivers a rare combination of total privacy, timeless craftsmanship, and stylish modern updates—all just minutes from town. Set far back from the road amid native landscaping, private woods, and a spring-fed pond, the home immediately welcomes you with warm cedar siding and an unmistakable sense of calm. Inside, soaring vaulted ceilings and a stunning three-story chimney—built from stone harvested directly on the property—create a dramatic focal point, while fresh paint, updated lighting, and newly installed hardwood floors bring a refined, contemporary feel throughout. The beautifully renovated kitchen features a center island, custom sage-green cabinetry, quartz countertops, stone floors, and an effortless flow into the dining and living spaces before opening onto a spacious deck overlooking the water. It’s the perfect setting for entertaining, outdoor dining, or quiet mornings with coffee and birdsong. Currently configured as a two-bedroom home with easy potential for a third small bedroom which is currently staged as an open office space, the layout includes a primary suite and a spacious, ~500-square-foot walk-out lower level with French doors and a cozy Vermont Castings wood stove. There is also a heated, insulated two-car garage with polished concrete floors and cedar accents that feels more like a designer workshop or studio than a garage. Combining turnkey comfort with room to create your own Catskills sanctuary, this exceptional property offers peaceful country living just eight minutes from the growing energy of “Jeff,” with the ever-popular destinations of nearby Livingston Manor and Callicoon close at hand. Sellers are optionally open to a long-term lease of the home (see MLS# 1034744). Just under 2 hours from the George Washington Bridge.
Courtesy: Compass Greater NY, LLC
838-877-8283
Set at the end of a quiet country drive just outside Livingston Manor, 57 Sheryl Davis Road offers the kind of privacy and connection to nature that defines the best of Catskills living. Surrounded by woods and bordered by a dramatic moss-covered bluestone rock face, this contemporary take on the many historic barns that dot the country roads in the area balances thoughtful design with warmth, ease, and quiet seclusion. The four-bedroom, two-bathroom home was designed with attention to detail for both weekend escapes or full-time living, pairing sleek modern finishes with grounded, cozy details. At the center of the home, a modern kitchen with waterfall island, sculptural light fixtures, and clean-lined cabinetry flows seamlessly into the main living space, creating an effortless setting for gathering, entertaining, or curling up on the couch for a movie night in. A wood burning stove adds warmth and atmosphere during the colder months, while a generously sized first-floor bedroom and full bath offer flexibility and comfort. Upstairs, the primary bedroom features its own fireplace — equal parts practical and whimsical — alongside two additional bedrooms and a second full bath. Outdoors, the landscape unfolds as an integral part of the property’s magical landscape. Spend evenings soaking in the hot tub beneath the stars, listening to the quiet and taking in the striking natural bluestone rock face that anchors the property. Multiple outdoor spaces (fire pit anyone?) invite dining, entertaining, and long afternoons settling into the slower rhythm of upstate life. Beyond the existing home, the acreage offers future potential. A slab foundation from a former structure still remains on the property, presenting opportunities for redevelopment, whether imagined as a guest house, studio, wellness retreat, or additional creative space. Private, design-forward, and deeply connected to its surroundings, 57 Sheryl Davis Road captures a distinctly modern Catskills lifestyle just moments from Livingston Manor’s beloved restaurants, breweries, shops, and year-round charm. A short drive from the nearby towns of Roscoe, Narrowsburg, and Jeffersonville - approximately two hours from NYC. If you’re looking for a private and modern upstate escape, you’ve found it at 57 Sheryl Davis.
Courtesy: Callicoon Real Estate LLC
845-887-4400
Love grand old homes, privacy and large airy rooms with lots of natural light? Have porch goals? Then this is the home for you. The home has been lovingly undergoing a restoration. Wood floors have been brought back to life in most of the home reflecting the care that was taken with them. The bathrooms have stayed true to the original time period with fully functioning sinks, toilets and clawfoot tub with shower. Venetian plaster glows in the upstairs bedrooms, hallway and attic. The spacious living room has been painted with a lime wash. With a woodstove keeping you cozy on cooler days. New chimney and gutters are part of the beauty. The kitchen is large enough that when entertaing guests they can hang out and keep you company while getting your chef on. Off the kitchen is a butlers pantry with a seperate entrance to the back yard. You can enter the kitchen through a mudroom with places for coats, boots and handy tools. Many of the ceilings are wainscoted. The attic is the bonus. It could easily be turned into an additional bedroom suite, art studio with lots of natural light, extensive library or a private sanctuary. Sit on the porch in the morning with a cup of tea or coffee and enjoy a crossant while reading the paper or watching the birds. Out side is a gardener's paradise with a small orchard with peach, plum, apple, pear and cherry trees. There is also a grape arbor. Daffodiles, peonies, lilacs, violets and many other flowers and herbs abound. A secret club house is tucked in the back yard. A brook meanders down the side of the property. The home sits well back from the road. A two minute drive to Jeffersonville which has a grocery store, bakeries, pharmacy, speciality stores, restaurants, ice cream stand and the library. It is an short 8 mile drive to Bethel Woods. Not far from Callicoon and the Delaware river, Livingston Manor and Roscoe for trout fishing. Less then 2 hours from the GWB and an easy drive from Route 17.
Courtesy: Hart & Johnson Realty
347-739-4723
Escape to a true Catskills retreat where privacy, charm, and natural beauty come together on over 5 picturesque acres. Tucked away behind a private driveway, this beautifully renovated property offers a peaceful setting surrounded by beautiful stone walls and scenic wooded landscapes. The inviting home features 3 bedrooms and 1.5 baths, thoughtfully updated while maintaining its warm country character. Outside, the property offers several versatile outbuildings, including a detached 2-car garage and an additional shed perfect for a bunkhouse, studio, or charming chicken coop. Enjoy long summer days relaxing in the gazebo, exploring the manicured walking trails that wind throughout the property, or gathering around the designated fire pit under the stars. Whether you’re looking for a full-time residence, weekend getaway, a lucrative air bnb, or country escape, this property captures the essence of Catskills living. Conveniently located near some of the area’s most beloved hamlets, including Livingston Manor, Roscoe, Jeffersonville, and Callicoon, offering easy access to dining, shopping, fly fishing, hiking, and year-round recreation.
Courtesy: HomeCoin.com
888-400-2513
Fully Remodeled Ranch in the Heart of Youngsville. Welcome to this beautifully updated 3-bedroom, 2-bath ranch-style home situated on 1.56 peaceful acres in the heart of Youngsville! This move-in ready property offers the perfect blend of comfort, space, and outdoor living. Inside, you’ll find a fully remodeled interior with a bright and inviting layout, including a spacious sunroom, gorgeous stone fireplace and large breezeway perfect for relaxing or entertaining. The home also features a garage and plenty of room for storage. Large Attic for storage. Step outside to your own private backyard oasis featuring a huge pool, spa, gorgeous patio, and expansive yard — ideal for summer gatherings, and fun, or simply enjoying the peaceful surroundings. If you’ve been searching for country charm with modern updates and incredible outdoor space, this is the one you’ve been waiting for!
Courtesy: Chapin Sotheby's Intl Rlty
845-583-4900
Perched atop a scenic mountain setting on 15.5 secluded acres, this contemporary country home offers sweeping panoramic views of the western Catskills, overlooking endless rolling hills, valleys, and open countryside. Surrounded by expansive lawns, professional landscaping, and mature woods, the property provides exceptional privacy and a peaceful setting in the heart of Sullivan County. A standout feature of the property is its two spring-fed ponds, both continuously supplied with fresh, crystal-clear water. One pond reaches depths of over 15 feet, while the second is approximately 10 feet deep and includes a charming gazebo/outbuilding along the shoreline — an ideal spot to relax and take in the surroundings. Built in 1992, and lightly used over the years, the home has been very well maintained and includes recently installed central air conditioning. There are beautiful hardwood floors in the living room on the main level and throughout the upper level. The first floor features a welcoming foyer, powder room, and a spacious living room with an impressive, vaulted ceiling and a dramatic floor-to-ceiling stone fireplace. The open-concept kitchen includes a breakfast bar and flows seamlessly into a generous dining space ideal for gatherings. Both lead to a covered deck designed to capture the breathtaking sunsets and mountain views—perfect for outdoor entertaining or quiet evenings at home. Upstairs, the primary suite is accompanied by two additional bedrooms, a full bath, and an open sitting area highlighted by a striking round floor-to-ceiling window framing the spectacular views beyond. Additional amenities include an attached two-car garage and a fully finished basement offering three versatile finished rooms that can easily accommodate home offices, a media or recreation room, fitness space, or guest overflow. Properties offering this level of privacy, magnificent scenery, water features, and quality construction are rarely available. Whether you're seeking a full-time residence or a refined country retreat, this exceptional property truly must be experienced in person to be fully appreciated.
Bring your vision to this thoughtfully reimagined 1940s farmhouse, where the most difficult and expensive renovation work has already been completed. Redesigned from a 1-bedroom, 1-bath home into a planned 3-bedroom, 2.5-bath layout, this property is ready for its next owner to add the finishing touches. Major improvements include new 200-amp electric service, all-new plumbing, high ceilings, energy-efficient Pella and Marvin windows, and an open floor plan designed to capture beautiful meadow and mountain views. Situated on 4 scenic acres, the property also includes a two-story barn across the road with endless potential as a garage, workshop, studio, or additional living space. Conveniently located near Livingston Manor, Callicoon, and Jeffersonville, this is a rare opportunity to customize a Catskills home while benefiting from substantial renovations already in place. The home is being sold as-is, with select building materials and fixtures included in the sale.
Courtesy: Country House Realty Inc
845-397-2590
Welcome to Kenoza Blue, a turnkey home with classic lines, ample space, and 160 feet of lake frontage on one of Sullivan County’s finest private lakes. Gut renovated in 2023, this home is move-in ready day one, and with five bedrooms, it’s also ready for hosting the whole gang on day one too. Throughout the home, you’ll find charm and character and that starts on the outside with a rocking chair porch greeting visitors. Step in to the generous foyer and immediately you’re struck by the classic walnut staircase, the stained glass window detailing, and the ease with which the house flows. The downstairs has four distinct rooms - each one separate but never disconnected. It’s an easy space to imagine hosting a large group. A large living room is ready for movie nights, a traditional dining room begs to host holidays and festive gatherings, and a new, streamlined kitchen with open shelving keeps the space feeling light and airy. You’ll also notice the original wood floors flowing throughout, balancing the newer finishes. A gut renovated full bathroom with walk-in shower rounds out the first floor. Like many classic lakehouses, the upstairs is reserved mostly for sleeping - and the downstairs, for the fun stuff. Up the stairs, and you’ll find all five bedrooms - all capable of supporting a queen or king bed, and all with closets. A stacked washer/dryer at the end of the hallway means easy laundry after a busy weekend with no toting up and down. The second full bathroom with shower and tub combo is right in the middle of the second floor, easily shared among the bedrooms. Outside, where you’re likely to spend much of your time, you’ll find 1.1 gently sloping acres with a mix of lawn, meadow, and woods, all leading down to your private dock and 160 feet of lakefront. A brand new deck leads off the back of the house, and right down to the yard for easy in and out access to the lake. Kenoza Lake is a non-motorboat, 90+ acre private lake known for its quiet, clean, swimmable waters and good fishing. Electric motors for trawling are permitted. An important detail - most homes that have lake access to Kenoza Lake are part of the Kenoza Lake Estates HOA which restricts short term rentals (airbnb etc.) among other things. Kenoza Blue is NOT part of the HOA, and short-term rental would be permitted in accordance with the town of Delaware. Kenoza Lake is centrally located in western Sullivan County with easy access to many of the county’s premier towns. Jeffersonville is only 5 minutes away, Callicoon is 15 minutes, and Narrowsburg - a little under 20. Just a five minute walk up the road is Kenoza Hall - a Foster Supply hotel with year-round restaurant and bar. Kenoza Blue is a compelling option for anyone looking for a sizable lakehouse with rentability, a great location, and a classic look and feel.
Courtesy: Matthew J Freda Real Estate
845-887-5640
The living is easy in this Delaware riverfront cottage. River Road is a special feature in Callicoon, as it is a low-traffic, dead-end road that runs 4 miles upriver. This property is situated near the end, where there is almost no traffic. It's a great spot to walk, ride bikes, and take in the beauty of the Delaware River. The eagles soar and the swimming and fishing are great. The cottage is efficiently built, with an open floor plan, kitchen, tile floors, wood stove, electric baseboard heat, 200-amp electric, insulated windows, full bath, sleeping area and extra sleep space in loft. It's easy to enjoy and easy to maintain. The land is level with a large fenced garden, orchard with diverse fruit trees and chestnuts, stone walls and 150 feet of your own riverfront. Leave the kayaks and canoes on the shore, just grab 'em and hit the water! The shed is perfect for gardeners to store all the pots, tools and mowers. Just 4 miles from Callicoon with its restaurants, shops, farmer's market, and more. Two hours NYC.
Courtesy: Country House Realty Inc
845-397-2590
Built to rigorous Passive House standards, Red Hill is a newly constructed 1,738 sq ft, 3-bedroom, 2.5-bath home just minutes from Livingston Manor, nestled within The Catskill Project's 90-acre community. Enjoy the best of the Catskills lifestyle while benefiting from a home designed to support your health, comfort, and well-being for generations to come. Certified to meet both PHIUS (Passive House Institute US) and U.S. Department of Energy Zero Energy Ready Home (ZERH) standards, this all-electric home features a super-insulated, airtight building envelope, triple-pane windows, and balanced heat recovery ventilation that delivers a continuous supply of fresh, filtered air. The result is exceptional year-round comfort, superior indoor air quality, and dramatically lower energy costs than conventional construction. Engineered to exceed code requirements, Red Hill ranks among the highest-performing homes available today - not just in the Catskills, but anywhere. This is a home built to last. An airy, open living space and expansive windows flood the home with natural light while framing beautifully wooded views in every season. The modern kitchen features premium JennAir NOIR appliances and custom cabinetry and flows seamlessly into the adjacent dining area and into a dramatic three-season room, creating an effortless indoor-outdoor experience perfect for dining, lounging, and entertaining. The three-season room comes equipped with a pellet stove, so it will be warm and cozy even in the winter months. Three well-proportioned bedrooms include a generous ground-floor primary suite with en-suite bath, offering privacy and flexibility for guests or a work-from-home lifestyle. The bathrooms feature custom tile work, bespoke vanities, and top-of-the-line fixtures. A second-floor lofted den with soaring vaulted ceilings adds a versatile bonus space - equally suited for movie nights, a yoga practice, or a quiet home office. A large deck adjoins the loft and overlooks your privately wooded lot, while the covered carport provides a welcome entry in any weather. Gather around the bluestone fire pit and enjoy the outdoors across all four seasons. If solar panels are installed, a battery closet is available to keep the house running should the power grid go offline. Step directly from the property onto The Catskill Project's private trails, which wind through a serene 40-acre nature preserve to pristine waterfalls - everything that makes the Catskills truly special, right at your doorstep. Red Hill and The Catskill Project are ideally situated less than 10 minutes from the vibrant villages of Livingston Manor and Roscoe, with Callicoon and Jeffersonville just a short drive beyond. So whether this is a full-time residence or a weekend getaway, there is easy access to great local restaurants, shops, and art galleries.
Courtesy: Country House Realty Inc
845-397-2590
Character may be an overused word in real estate, but it’s a rare home that exhibits as much warm gravitas as Old Hankins Manor. From the moment you pull up the drive, past the private half acre pond and up to the wraparound rocking chair porch, you’re struck by a sense of timelessness and comfortable elegance. Tucked back from the quiet country road, this home has stood sentinel over the surrounding farmland for over 125 years. The formal front entrance welcomes you into a generous foyer with ornate staircase. Nestled behind this is a cozy media room, tucked away from the rest of the living space. The sitting room and den with stone double-sided fireplace welcome you into the primary entertaining space, then through to the spacious formal dining room, with the other face of the fireplace and wooden built-in shelving. The kitchen is highly functional while retaining an old country charm - think red checkered linens, aged porcelain sink, weathered wood and fresh baked cherry pies. Off this space is a convenient pantry with floor to ceiling cabinets and an additional sink. A full bathroom off the kitchen also houses a washer/dryer unit. At the second floor landing, you’ll find a lovely, sunny sitting room before heading down the hallway housing five bedrooms, each with a distinct character, allowing you to direct your guests to the ‘lilac room’ or the ‘red room’. There are two full bathrooms on this floor, one with a clawfoot tub, positioned under a dramatic stained glass window, and another with a tiled shower with charming old-style fixtures. The third floor houses a massive primary suite. The bedroom features a circus-tent-like peaked ceiling, working brick fireplace and large sitting area. A full en suite bath offers another clawfoot soaking tub and walk in tiled shower with skylight. A charming dressing room and large glass-encased office finish off this floor. Outside, a pathway off the back of the house leads past a stone patio with fire pit to the heated pool. The simple layout of the this area allows you to appreciate the natural privacy of open fields and mature trees. To the other side of the property, the clear freshwater pond offers opportunities for swimming, paddling, and peaceful contemplation. The front lawn is large and lightly sloping, making it inviting for lawn games for your family and friends. Almost unbelievably, this idyllic escape is also just a ten minute walk to all the charms and conveniences of Main Street, Callicoon.
Courtesy: Keller Williams Upstate NY Pro
607-431-2540
Perched above the heart of Callicoon, this 1908 landmark stands as one of Sullivan County's most captivating historic structures—a former schoolhouse whose legacy spans education, craftsmanship, and art. Over the decades, its grand proportions have sheltered classrooms, a dress factory, and a piano workshop—each chapter leaving its mark in the woodwork, wainscoting, and soaring ceilings that remain today. Now reimagined by artists, the building bridges eras with a rare blend of authenticity and modern livability. A bright three-bedroom, two-bath residence offers comfort and warmth with custom cabinetry, solid wood floors, and rich natural light. Beyond, the structure unfolds into vast and inspiring spaces: a 60-by-34-foot gymnasium with a 20-foot ceiling and stage; a luminous upper-floor dance studio spanning nearly sixty feet; art studios inspired by gigantic windows bringing in nature and sunlight, open workrooms, and a full stacked stone-foundation basement with walk-in access. At roughly 13,000 square feet on over an acre, the property invites both vision and versatility. Zoned for mixed use, it can evolve into a gallery and performance venue, a live-work compound, a wellness retreat, or a community hub. Every beam and window suggests possibility—every echo in the old gym reminds you that this building was made for voices, for movement, for gathering. Surrounded by ornamental trees and perennial gardens, and just a short stroll from Callicoon's beloved cafes, the farmers' market, and the Delaware River, 48 Upper Main offers both privacy and presence. It is that rare piece of architecture that feels both anchored in history and untethered in potential. Updated infrastructure includes a new metal roof and a new boiler (with a copper manifold that will inspire envy). A place where authenticity reigns, light abounds, and inspiration seems to gather naturally within the walls. 48 Upper Main Street isn't just a building—it's a living story waiting for its next author. Offering includes two tax parcels .89 acres and .25
Courtesy: Keller Williams Upstate NYProp
585-877-8283
Perched above the heart of Callicoon, this 1908 landmark stands as one of Sullivan County’s most captivating historic structures—a former schoolhouse whose legacy spans education, craftsmanship, and art. Over the decades, its grand proportions have sheltered classrooms, a dress factory, and a piano workshop—each chapter leaving its mark in the woodwork, wainscoting, and soaring ceilings that remain today. Now reimagined by artists, the building bridges eras with a rare blend of authenticity and modern livability. A bright three-bedroom, two-bath residence offers comfort and warmth with custom cabinetry, solid wood floors, and rich natural light. Beyond, the structure unfolds into vast and inspiring spaces: a 60-by-34-foot gymnasium with a 20-foot ceiling and stage; a luminous upper-floor dance studio spanning nearly sixty feet; art studios inspired by gigantic windows bringing in nature and sunlight, open workrooms, and a full stacked stone-foundation basement with walk-in access. At roughly 13,000 square feet on over an acre, the property invites both vision and versatility. Zoned for mixed use, it can evolve into a gallery and performance venue, a live-work compound, a wellness retreat, or a community hub. Every beam and window suggests possibility—every echo in the old gym reminds you that this building was made for voices, for movement, for gathering. Surrounded by ornamental trees and perennial gardens, and just a short stroll from Callicoon’s beloved cafes, the farmers’ market, and the Delaware River, 48 Upper Main offers both privacy and presence. It is that rare piece of architecture that feels both anchored in history and untethered in potential. Updated infrastructure includes a new metal roof and a new boiler (with a copper manifold that will inspire envy). A place where authenticity reigns, light abounds, and inspiration seems to gather naturally within the walls. 48 Upper Main Street isn’t just a building—it’s a living story waiting for its next author. Offering includes two tax parcels .89 acres and .25
Callicoon is located in New York. Callicoon, New York has a population of 2,996. Callicoon is less family-centric than the surrounding county with 21.08% of the households containing married families with children. The county average for households married with children is 27.82%.
The median household income in Callicoon, New York is $64,813. The median household income for the surrounding county is $63,393 compared to the national median of $69,021. The median age of people living in Callicoon is 49.8 years.
The average high temperature in July is 79.8 degrees, with an average low temperature in January of 12.5 degrees. The average rainfall is approximately 49.3 inches per year, with 66.5 inches of snow per year.
