Courtesy: Country House Realty Inc
845-397-2590
Tucked down a long driveway, Valley View is perched along a ridge enjoying two of the finest amenities houses can offer: views and privacy. Valley View is rich in country charm and coziness, with a flexible chalet layout sure to work well as a countryside retreat. Entering the house from the handsome entryway, you’re greeted with a classic chalet layout and cabin feel - bedroom and bathroom tucked to the rear of the house on opposite sides of the entry foyer, and a great room to the front of you. Long range valley views hit you immediately, with the sensation that the house is nearly floating in the sky. The great room is balanced between its wall of windows and long range views, with the coziness of the Jotul wood stove on the far side. This is an easy room to imagine enjoying year round whether soaking in the summer sun or cozying up in front of a fire with a gentle snow falling. An open kitchen is compact but highly functional with ample storage (including additional closet space in the hallway.) When the deck isn’t available for al fresco dining, the eat-in kitchen is more than adequate while enjoying meadow views to the north side of the house. Upstairs, a nearly 400 square foot loft can be used in myriad ways. Currently set up as a den and play room, this could easily be converted to a dedicated bedroom or office - or keep it flexible and let it work for whatever the day calls for. Downstairs, the finished walk-out basement is currently configured as an additional bedroom suite. There is plenty of opportunity to flex this space to whatever use is desired, much like the loft. The basement features an additional full bathroom, stacked laundry, and ample storage spread across multiple closets. Directly outside the basement you’ll find the six-person hot tub with some of the best soaking views available. Valley View sits on 7 pastoral acres, and includes a small pond accessed via a trail from the house. The house sits nearly halfway down the parcel with large fields and lawn surrounding. No shortage of room for adding amenities. In addition, there is an adjacent 47 acre parcel that surrounds the home also available for purchase. The Beechwoods district of Callicoon is some of the most desirable land in all of Sullivan County and this is a unique opportunity to grab your slice of it. Only ten minutes from both Callicoon and Jeffersonville, Valley View sits in a privileged pocket of the Western Catskills with quick access to some of the most loved towns in the area. Don’t miss out on this perfect little country escape. Reach out for a private showing.
Courtesy: Compass Greater NY, LLC
838-877-8283
A little country club, a little horse country. Set on five private acres in Callicoon’s Beechwoods, Little Holiday Farm is a beautifully updated Catskills farmhouse pairing sweeping pastoral views, a horse ready barn, and direct access to an 18-hole championship golf course. Originally built in 1948 and extensively renovated in 2015, the four-bedroom, two-bath home has the warmth and character you want in an old country house, but with modern comforts. Hardwood floors, beamed ceilings and a gas fireplace bring plenty of cozy charm, while an updated kitchen with stainless-steel appliances keeps things decidedly current. The spacious primary suite feels like a retreat of its own, with its own private screened porch overlooking the rolling hills of the Beechwoods. With a first-floor bedroom and full bath, three additional bedrooms and plenty of gathering space, there’s room to comfortably host a full house of family and friends. At the opposite end of the house, a shaded porch overlooks the grounds and pole barn, offering plenty of space for four-wheelers, motorcycles, outdoor toys - or a few four-legged friends. A full walk-out basement provides additional storage and possibilities, while five usable acres offer room to garden, roam, play and take in those big Beechwoods skies. New septic in 2025. Surrounded by rolling countryside, evenings here are measured in sunsets and stars and just how long you can stay on the porch. When civilization calls, the shops, restaurants, farmers markets of the bustling hamlets of Callicoon and Jeffersonville are both just a short drive away. Just down the road, Villa Roma serves up classic Catskills resort life - championship golf, skiing come winter, plus dining, swimming, racquet sports, bowling and plenty more. Approximately 2 hours to New York City. Little Holiday Farm is country living at its best: five beautiful acres, a barn with room for horses and farmstead dreams, all wrapped in the rolling landscape of Callicoon’s Beechwoods.
Courtesy: Compass Greater NY, LLC
838-877-8283
Steps from Callicoon’s charming Main Street and the Delaware River, this beautifully preserved 1900 Craftsman pairs the soul of another era with a decidedly modern point of view. Designed and built by Kohler Lumber, the local mill responsible for some of the area’s most distinctive early homes, it remains a remarkable showcase of period craftsmanship. Original Victorian 'stick and ball' millwork, carved details, paneled walls, and beautifully restored wood floors give the house a richness and sense of place that simply cannot be recreated. Thoughtfully updated while respecting its architectural history, the interiors feel warm, quiet, and refined. Original floors restored with tung oil and a subtle white-pigment finish bring a fresh, contemporary softness to the home’s extraordinary woodwork. The walls and first-floor ceilings were meticulously restored using traditional lime plaster over the home’s original wood lath. The bright, streamlined kitchen is simple and efficient, with room for a future owner to expand if desired. An adjacent powder room with laundry adds practicality, while the dining room’s carved wood details create an intimate transition to the open living and sitting rooms. The front parlor retains a particularly charming piece of the home’s history: once used as an insurance office and separated from the residence by a velvet curtain, its original iron curtain rod remains. A carved wood staircase leads to generously proportioned bedrooms, an updated bath, and a dedicated bathing and soaking suite - an unexpected and indulgent retreat. Above, the wood-paneled attic offers an atmospheric, flexible space for movie nights, a studio, home office, library, or future expansion. Behind all that history is a house thoughtfully brought into the present. Updated mechanicals, cellulose insulation installed in 2022, and a low-energy cooling system that draws naturally cool air from the stone-walled, below-grade cellar. The original 1912 cedar siding was fully stripped and restored in 2012 and repainted in 2024. Municipal water and sewer add another layer of ease. Outside, the property becomes a private little world of its own. Mature perennials, native plantings, moss-covered stone walls, and an outdoor fireplace create an enchanting backdrop for long summer dinners, cocktails by the fire, or slow mornings with coffee. Just off the kitchen, the garden makes entertaining effortless. Out front, a secluded rocking-chair porch wrapped in greenery makes it easy to forget that the heart of town is just steps away. Stroll down the hill to the Delaware River for swimming, fishing, and rafting, into town for dinner and drinks, or to the Callicoon Farmers’ Market on Sunday mornings. The new 40-acre Callicoon Riverside Park is also just a few minutes away on foot, while Grover M. Hermann Hospital is approximately two minutes away by car. Historic without feeling frozen in time and polished without losing its soul, the Callicoon Craftsman is a rare opportunity to own a beautifully preserved piece of local history in one of the Delaware River Valley’s most beloved hamlets.
Courtesy: Woodstock Way Realty LLC
845-250-4200
Your Catskills escape awaits! This inviting 2-bedroom, 2-bathroom condo at Villa Roma offers the perfect blend of comfort, recreation and resort-style living. Enjoy access to an incredible range of amenities and activities, including indoor and outdoor pools, golf, tennis, pickleball, hot tubs, dining, live entertainment, skiing, snowboarding, snow tubing and more. Whether you're looking for a weekend getaway, vacation home or investment opportunity, this property puts four-season Catskills recreation right at your fingertips. Just minutes from Callicoon's shops, restaurants, farmers markets and the Delaware River, you'll have everything you love about the Catskills close by. Own the getaway. Enjoy the resort. Live the Catskills lifestyle.
Courtesy: Houlihan Lawrence, Inc.
845-876-4443
Welcome to the Beechwoods, a disarmingly bucolic pocket of Sullivan County dotted with cattle lazing by a stream and sheep foraging across rolling hills. Here in the agrarian calm, high above Callicoon, sits the Beechwoods House, looking out across one of the western Catskills' most beautiful landscapes: undulating farmland, wooded hills and an extraordinary expanse of sky. Set within 7.85 acres of meadow and native plantings, the home was designed around this view, with its main living spaces facing west toward the sunset. Although custom built in 2022, the house feels as though it has been here for generations. Weathered wood, cobblestone floors, deep rooflines, and rooms filled with warmth and patina give it the soul of an old Catskills homestead, while its open layout and effortless connection to the outdoors are distinctly modern. The architecture sits quietly within the landscape, emerging from the meadow rather than imposing upon it. At the center of the home is an expansive living room anchored by a sleek gas fireplace. Walls and ceilings wrapped in wood create an enveloping sense of warmth, while a broad bank of windows frames the countryside beyond. There is ample room to gather, read, play games, or simply settle in beside the fire. A built-in nook offers a quiet corner of its own, made for curling up with a book while still feeling connected to the rest of the room. Doors open to outdoor spaces on two sides. One looks west across the hills, an idyllic place for dinner as the last light moves over the valley. The other is a more intimate retreat surrounded by lush native plantings. Open both sides of the room in summer to let the breeze and birdsong move through the house. In winter, the radiant-heated cobblestone floors, richly textured wood, and oversized hearth make the entire space feel wonderfully cocooning. The kitchen has the easy, collected character of a French country house. Wood cabinetry, open shelving, skirted worktables, an apron front sink and patinated natural materials give the room the feeling of having come together slowly over time. It is generously scaled, with space for a dining table at its center and windows looking out toward the landscape. Off the kitchen is a convenient mudroom and laundry area with a half-bath. A separate outdoor sitting area just outside the kitchen creates yet another place for morning coffee or a quiet lunch in the garden. The private bedrooms extend along two wings, giving the home a natural sense of separation. One hall leads past a cozy den to the primary suite, where the bath pairs warm wood with a freestanding soaking tub, separate shower and water closet. Three additional bedrooms and a full bath occupy the opposite side of the house. Each room has its own tacit personality, with soft light, simple materials, and windows that look into the meadow and surrounding greenery. Off the living room, up a concealed stairway, is one of the home's more unexpected spaces: a generous loft tucked beneath the pitched roof. Warm wood ceilings follow the roofline overhead, while windows on multiple sides bring in light and views of the surrounding treetops. Connected to the character of the house but removed from its main gathering spaces, it feels like a private world of its own, and could easily become a screening room, library, painting studio, music room, home office or guest suite. Outside, the property unfolds through covered terraces, slatted pergolas, garden paths, and pockets of meadow alive with grasses and wildflowers. Adirondack chairs placed at the edge of the hill invite you to sit and take in the long western view. The nearly eight acre property feels wonderfully private, yet remains open and expansive, with the house appearing almost hidden within the landscape, a truly rare confluence of traits that almost every buyer hopes to find. Despite its seclusion, the Beechwoods is just ten minutes from Callicoon, one of the Catskills' most beloved river towns. Spend Sunday morning at the year round farmers' market, choose a bottle at the Callicoon Wine Merchant, have cocktails and dinner at Black Walnut, or see a film beneath the marquee of the historic Callicoon Theater. Nearby, Seminary Hill offers cider, food, and beautiful views across the Delaware River Valley. The river is central to life here, with swimming, kayaking, tubing, and fishing throughout the warmer months. Ten minutes in the other direction, Jeffersonville is home to Sullivan Sundries, a beautifully curated destination for coffee, specialty provisions and home goods. Nearby Bethel Woods brings major concerts and festivals to the historic Woodstock site, while Narrowsburg, Livingston Manor, and Roscoe offer restaurants, breweries, antiquing, and some of the region's best fly fishing. Just 2.5 hours from New York City, 506 Beechwoods offers the rare combination of deep quiet and genuine connection. Additionally, this turnkey home is offered furnished, preserving the layered, highly curated interiors that make it feel so immediately inviting. A house that feels removed from everything when you want it to, with some of the Catskills' best food, culture, and small town life close at hand.
Courtesy: BERKSHIRE HATHAWAY
516-741-3070
A true Callicoon landmark, Rafters Tavern has been a staple of the community since the building's construction in 1885. Located in the heart of town, this turnkey restaurant with commercial kitchen, bar and live music venue offers a rare opportunity to acquire an established hospitality business with a loyal following. The property includes a manager's/owner's apartment and additional rentable rooms, providing multiple income streams and operational flexibility. Rich in character and history, Rafters is well-positioned for continued success as one of the area's most popular gathering places for dining, entertainment, and live performances. The property also includes an additional commercial space suitable for retail or complementary business use. Heating/Cooling system: propane upstairs, forced air and central AC, downstairs electric heating & cooling units
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: Matthew J Freda Real Estate
845-887-5640
Are you tired of every house in this area looking the same-old, same-old dark color? Well, this brand-new build is a breath of fresh air! Gorgeous 3 BR/2bath custom contemporary sits on 5.25 acres in Callicoon, white in color with black trim. It really pops, and looks so different than those cookie-cutters, yet thoroughly modern! Constructed by one of the premiere builders in our area, JIT Construction, you can count on quality workmanship and an eye for detail! From the moment you pull in to the driveway, you'll see the 2-car garage attached to the home via a breezeway, which makes it easy in bad weather. Step into the house via the mudroom/laundry or the front entrance and you'll be greeted with an open floor plan: a soaring cathedral ceiling in DR/LR area. The living room has floor to ceiling glass, washing the home with natural light. A gorgeous LP gas stone fireplace takes center stage here, adding heat and creating ambience. The kitchen is a dream! Crisp white quartz counters that gleam with light accented by a gorgeous pendant light fixture... Lots of counter and cabinet space here, enough to make a chef drool! You can dine at at the island, though there's plenty of room for a table & chairs too, just beyond. Primary BR off to the right; spacious walk-in closet and a sliding door that opens to the deck. There are two other BRs and a full bath off to the left. Walk outside via the sliders in living room to find a huge deck which runs the length of the home. You'll be soothed by the peace and quiet of nature and birdsong. The home is painted in pleasing neutrals for color, but it's far from boring, as evidenced by the decorative tiles in bathrooms and the gorgeous quartz counters. Chic ceiling fans and central AC. The home is located just a couple minute's drive to Callicoon, where you'll find Delaware River access and fun, all kinds of shops and eateries, a movie theater, bowling alley, Sunday Farmers Market, supermarket, hospital, banks, and Visitors Center in the Train Station. 15 minutes south to Narrowsburg. 20 minutes to Bethel Woods Center for the Arts for concerts and cultural events.
Courtesy: Century 21 Geba Realty
845-856-6629
Historic Beechwoods Farmhouse on 14+ Acres, Major Improvements Already Made & Ready for Your Vision A rare opportunity in the highly desirable Beechwoods area of Callicoon. Set on more than 14 scenic acres between Callicoon and Jeffersonville, this historic four-bedroom, two-bath farmhouse offers the character, land, and setting you are looking for in the Sullivan Catskills. Along with an opportunity to complete the renovation to your own taste. Significant improvements are already complete, including a new roof, new porch, and partial interior renovation. The major work already started gives you a solid foundation to keep transforming the property. Bring your ideas, your style, and your vision to complete this Catskills farmhouse the way you want it. The property offers a wonderful combination of open meadows and wooded acreage, with gently rolling land and beautiful countryside. Three varieties of berry plants add to the property's agricultural character and offer the opportunity for gardening, harvesting, and enjoying the land. The farmhouse's history as both a working farm and seasonal retreat adds to its character and sense of place. Today, it offers the potential for a classic country farmhouse, Catskills retreat, hobby farm, hunting retreat, or private weekend getaway. The location is equally compelling. Approximately four miles from the Delaware River and conveniently situated between Callicoon and Jeffersonville, you'll be close to fishing, kayaking, canoeing, tubing, hiking, cycling, farmers' markets, restaurants, breweries, and the many cultural and recreational attractions of the Sullivan Catskills. The sellers are motivated. If you've been considering this property but weren't sure it was the right time to move, now is the time to take another look. This parcel has plenty of road frontage that may allow for another building site.
Courtesy: Hart & Johnson Realty
347-739-4723
Peaceful Country Retreat on Over 5 Acres Welcome to 12 Mesmer Road — a charming country home set on more than 5 scenic acres, offering privacy, tranquility, and plenty of space to enjoy the outdoors. Whether you’re searching for a full-time residence, weekend escape, or investment opportunity, this property delivers the perfect blend of comfort and countryside charm. The home features three bedrooms and two full bathrooms, along with a spacious eat-in kitchen and separate dining area ideal for family gatherings and entertaining. The oversized living room is filled with natural light thanks to a skylight and large sliding glass doors that open to the backyard patio — perfect for outdoor dining and relaxing summer evenings. Step outside to take in beautiful country views, mature trees, classic stone walls, and peaceful creeks that run throughout the property. On warm days, enjoy your own private heated in-ground pool, creating the ultimate setting for summer fun, barbecues, and quiet relaxation. Conveniently located just minutes from Callicoon, Narrowsburg, Jeffersonville, and Bethel Woods Center for the Arts, this property offers the serenity of country living while remaining close to local shops, dining, and entertainment. If you’re looking for space, privacy, and a true escape to the countryside, 12 Mesmer Road is a must-see. Schedule your private showing today!
Courtesy: Hart & Johnson Realty
347-739-4723
Set on 10 breathtaking acres with sweeping panoramic views, this exceptional property offers the perfect blend of comfort, privacy, and Catskills charm. The beautifully maintained home features 3 bedrooms and 3 bathrooms, thoughtfully designed living spaces, and expansive decks that showcase the stunning natural surroundings from nearly every angle. At the heart of the home is a spacious thought out kitchen complete with skylights, abundant storage, and generous counter space—an inviting space any home chef will appreciate. Sun-filled living areas feature oversized windows that frame the landscape and create a seamless connection to the outdoors. The finished lower level is designed for entertaining, featuring a full wet bar, full-size pool table, and direct access to an inviting patio and outdoor firepit area—perfect for relaxing evenings under the stars while taking in the peaceful scenery. Additional highlights include a fantastic detached two-car garage and beautifully usable acreage ideal for recreation, gardening, or simply enjoying the tranquility of nature. Conveniently located just minutes from the charming hamlet of Callicoon, and a short drive to Narrowsburg, Livingston Manor, Jeffersonville, and Roscoe, this property offers easy access to some of the region’s best shopping, dining, farmers markets, and outdoor recreation.
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: KW Hudson Valley United
845-791-8648
Step into serene sophistication with this immaculate custom contemporary Gambrel-style country home, a true architectural showpiece blending rustic charm with modern design. The expansive open-concept living space stuns with soaring 30-foot Hemlock wood ceilings, dramatic exposed beams, and a floor-to-ceiling stone fireplace. Gleaming hardwood floors and panoramic windows flood the home with natural light, perfectly framing sweeping views of Pennsylvania and New York’s rolling countryside. Awarded Sullivan County’s 2007 Home of the Year, this 3,750 sq ft residence sits gracefully on 7.32 stone-walled private acres. The thoughtfully designed floor plan features four bedrooms and 3.5 baths, including two luxurious primary ensuites. Custom touches are everywhere: radiant heat with central A/C, a chef’s kitchen with bluestone island counters, Wolf six-burner stove, SubZero refrigerator, and Miele appliances, plus wine fridges to complete the picture. Remote Nest controls, a steam room, hot tub, and outdoor shower add everyday luxury. The lifestyle continues outdoors with terraces, open sky, half basketball/pickleball court, garden and your own private retreat. A two-story 2,000 sq ft barn-door garage provides space for cars, recreational gear, or even creative projects. There’s also a 2nd floor space to expand your imagination! Whether it’s entertaining around the fire, soaking in the hot tub, or simply enjoying quiet mornings with sunlight pouring in, this home is built for comfort and unforgettable moments. All just two hours from NYC, minutes to Callicoon and the Delaware River with its fine dining, shops, and cultural life. This Catskills treasure offers the best of both worlds—modern elegance set against timeless country beauty.
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
Three story Victorian 5-BR home located on the end of a quiet cul-de-sac overlooking the bustling village of Callicoon, the Callicoon Creek and the Delaware River. In-town living doesn't get better than this. Enter on a large wrap-around porch and into a well-built home. You are greeted by an expanse of gleaming wood floors and a large living room and dining room. The updated eat- in kitchen has oak cabinets and granite counter tops. French doors lead into a quiet family room. Upstairs on the 2nd level find 3 bedrooms and a full bath. The 3rd level has 2 bedrooms with an additional bonus room. In the basement you will find the oil furnace, 200-amp electric panel and plenty of room for storage or workshop. This grand home has many original features such as beautiful wood floors, wood trim, 2- story staircase, stained glass windows, and more. Updated features include replacement windows, vinyl siding and a mini-split unit on first floor for heat and AC and fully insulated. Need storage and parking? Outside find a large detached 1-car garage plus a fenced in garden. In-town living is easy, because Callicoon is a fun town with activities including: The Farmers Market, movie theater, a community center offering tennis, swimming pool and pickleball, the Delaware River, great restaurants and shops.
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.
