Courtesy: Hart & Johnson Realty
347-739-4723
Streamfront Retreat 5 Bedrooms Newly Renovated Youngsville, NY Welcome to your Catskills escape! This beautifully renovated 5-bedroom home, set along a peaceful stream in Youngsville, offers the perfect blend of space, comfort, and natural beauty. Step inside to discover a brand-new kitchen that flows seamlessly into a bright, open living area, complemented by a formal dining room—ideal for entertaining. The home features a spacious layout with one large bedroom on the main level and four additional bedrooms upstairs, along with a convenient laundry room and two full bathrooms. The primary suite is a true retreat, boasting high ceilings, generous space, and a private en-suite bath. Enjoy outdoor living from both the charming front porch and the expansive rear deck overlooking your backyard oasis. A tranquil creek runs the full length of the property, creating a serene setting perfect for relaxing, strolling, or simply unwinding in nature. Additional creek frontage is also available for those seeking even more space. Ideally located near the vibrant hamlets of Jeffersonville, Livingston Manor, Roscoe, and Callicoon, you’ll enjoy easy access to dining, shopping, and outdoor recreation—while still savoring the peace and privacy of your own streamside haven. A rare opportunity to own a spacious, move-in-ready home with stream access in the heart of the Catskills.
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: Compass Greater NY, LLC
838-877-8283
Set high above the surrounding countryside, where eagles glide and the air shifts a little quieter, this extraordinary hilltop retreat offers architectural distinction, total privacy, and a true sense of escape - approximately two hours from the bustle of New York City. A winding, forested drive reveals the home gradually, heightening the arrival. Custom-built with Californian and Japanese influences, the residence is thoughtfully plotted to capture sweeping views and natural light through a dramatic curved wall of floor-to-ceiling windows. A soaring two-story stone chimney anchors the space, with steel beams fanning outward to frame the landscape like living art. Inside, the scale is grand yet warm. Radiant-heated bluestone floors, wood and stone sourced from the property, and refined natural finishes create a grounded, elevated feel. The open living and dining area flows into a true chef’s kitchen with marble countertops, Wolf range, Sub-Zero refrigeration, Gaggenau steam oven, walk-in pantry, and a pizza oven built into the bluestone fireplace. Just beyond, a screened-in porch invites slow mornings and long evenings wrapped in nature. The main level includes a serene primary suite, while upstairs offers two generous additional bedroom suites with stunning views, one with a traditional Hinoki soaking tub offering a truly unique self-care moment. A suspended balcony overlooks the living space, perfectly positioned to take in the ever-changing panoramic view of the mountains and the countryside below. Thoughtful details include towel warmers in each bathroom, a dedicated tea kettle burner and two sinks in the kitchen, and a dumbwaiter from the garage to the pantry. A full, unfinished lower level offers flexibility for an artist studio, gym, or workshop, along with two-car garage access. While the property itself is the epitome of privacy, Callicoon Center is central to so many great destination towns, with Callicoon, Livingston Manor, Roscoe, North Branch, and Jeffersonville only 10-20 mins away. A myriad of fine and fun dining can be found in the area starting right down the road at Conover Club at Callicoon Hills, and there are dozens of amazing local businesses to support! This area is famous for its sweeping rural beauty and fly fishing, in addition to tons of hiking, swimming, kayak/canoeing, and more. Two hours to the GWB in NYC.
Courtesy: Resort Realty
845-791-5945
Opportunity meets location in the heart of the Livingston Manor and the scenic Catskill Mountains. Tucked away off the road on 1 private acre with peaceful wooded views, this 3-bedroom, 1-bath home, with an additional home office space offers the perfect setting for those looking to create their own country retreat. 2 bedrooms upstairs and a potential additional bedroom in basement. Set back for added privacy, the property features an attached 2 car garage and full basement. This fixer-upper is ideal for buyers with vision who understand the value of a prime location. Just minutes from the charming downtown of Livingston Manor, enjoy easy access to beloved local shops, restaurants, cafes, and the vibrant small-town atmosphere that has made the area so desirable. Outdoor enthusiasts will love being close to world-class fishing, hiking, kayaking, and year-round Catskills recreation. Whether you're searching for a weekend getaway, investment opportunity, or full-time residence to make your own, this property offers endless potential in one of Sullivan County’s most sought-after communities. Located 2 hours from NYC, come and enjoy all that Sullivan County Catskills has to offer!
Courtesy: Century 21 Geba Realty
845-856-6629
Welcome to your own Beechwoods retreat, where timeless farmhouse charm meets artful, modern living. Set on three private acres at a picturesque corner between Callicoon and Jeffersonville, this distinctive home is anything but ordinary. Sunlight pours through oversized windows, illuminating wide-plank floors, exposed beams, and thoughtfully curated spaces that feel both expansive and intimate. At the heart of the home, an open, airy layout flows effortlessly from the inviting living areas to a striking dining space, perfect for long, memorable gatherings. The kitchen blends warmth and functionality with rich wood surfaces, clean lines, and views that bring the outdoors in. Throughout the home, design-forward touches, bold textiles, sculptural lighting, and cozy woodstoves create an atmosphere that is both sophisticated and deeply comfortable. With five bedrooms and flexible bonus spaces, there’s room to host, work, create, or simply unwind. Each room offers its own sense of calm, framed by greenery and natural light. Step outside and the magic continues: an in-ground pool, expansive teak patio, and rolling lawn bordered by mature trees invite lazy summer afternoons and starlit evenings. A charming outbuilding, three-car garage, and workshop add both character and practicality. Private yet perfectly positioned, this home offers the best of the Catskills lifestyle, minutes from beloved local towns, dining, and year-round outdoor adventure. This is more than a home, it’s a place to gather, to breathe, and to stay a while.
Courtesy: Corcoran Country Living
845-338-5832
Charming Tudor-style home on a spacious lot in the heart of Sullivan County. The main level features a living room, dining room, kitchen with outdoor porch, and a large flexible room ideal as a third bedroom or home office, while two bedrooms are located upstairs. Set on a large, usable yard with room to expand or create outdoor living. Strong value-add potential in a growing market, minutes to Jeffersonville, Livingston Manor, and Callicoon.
Courtesy: Callicoon Real Estate LLC
845-887-4400
Welcome to Beechwoods Estates at Villa Roma Resort! Here is a desrable ground floor 2 bedroom, 2 bath condominium in excellent, move-in condition. Sellers cherished their years of ownership and the time has come for a younger generation to enjoy all 4 seasons in the Sullivan County Catskills and its premier Villa Roma Resort in the Delaware River valley in western Sullivan County. Included in the purchase price is a time share week with a yearly maintenance fee of $1487 enabling the new owners to take advantage of all amenities the Resort offers such as indoor and outdoor pools, tennis, etc. And of course, there is the gorgeous golf course! Come and take a look! Sellers will make it easy for you to spend your first night of ownership at your new vacation home!
Courtesy: Keller Williams Upstate NY Properties
607-510-4444
This charming 1940s farmhouse is a special find. It’s mid-gut renovation so all the difficult and expensive work has been completed, waiting for you to bring the finishing touches. The design and floorplan layout has been thoughtfully re-imagined. A professional interior designer has transformed it from a 1-bed/1-bath (1,146 sq ft) to a 3-bed/2.5-bath (1,542 sq ft), enhancing space, flow, and natural light. Designed to blend indoor and outdoor living, the home boasts high ceilings, energy-efficient Pella and Marvin windows, and sliding doors that open to an eventual deck overlooking a stunning meadow and mountain view. The main floor features a spacious living room/kitchen, a new mudroom, and a light-filled primary bedroom with an en suite bath. A circular pea gravel driveway, 200-amp electric service, all-new plumbing, a washer/dryer hookup, and a coffee bar/wet bar sink have been installed. The upstairs offers two well-sized bedrooms and a full bath, with newly framed ceilings for added height. Situated on 4 acres, the property includes a 2-story barn across the road, with potential for a garage, workshop, cabin or studio conversion. Located in North Branch, a peaceful hamlet near Livingston Manor, Callicoon, and Jeffersonville. Being sold as-is, the asking price takes into account the completed renovations and the remaining work. Some building materials and fixtures are included, with additional remodel items available for purchase. Contents that are included in the sale: Drywall panels, Batting insulation, Marvin sliding window (for upstairs bedroom), Pella Window (for second upstairs bedroom), Vintage wooden shutters (for street-side exterior), Fiberglass clawfoot tub and plumbing fixture, Upstairs vanity, bar sink and faucet, 2 matching chandeliers for living room, Vintage brass chandelier for mudroom, Marvin French door (for living room), Decking wood. Other items can be negotiated.
Courtesy: Country House Realty Inc
845-397-2590
Located at the end of a quiet cul-de-sac, this stately Victorian home boasts old-world charm and overlooks the sweet river town of Callicoon. Step inside and discover a treasure trove of delightful details: charming nooks and crannies, a sunny pantry, a built-in bar, and inviting window seats. The current owners have tastefully enhanced the home with numerous improvements, including newly painted interiors, beautifully refinished wood floors throughout, fully renovated bathrooms, and updated light fixtures. Entering, you're greeted by a welcoming foyer, complete with handy hooks and shelves for all your outdoor gear. From there, you're drawn into the center of the home where a two-sided fireplace offers the warmth of a wood-burning fire on one side. The other side houses a pellet stove, efficiently heating both the dining and living rooms, which are painted in a sophisticated, moody blue. The living room is bathed in natural light from large windows overlooking the front porch and features floor-to-ceiling shelving. The dining room, perfect for entertaining, includes a built-in bar area or buffet and provides direct access to the expansive wrap-around porch. Just beyond the dining room, discover the cheerful, updated kitchen. It boasts new butcher block counters, all new appliances, and freshly painted cabinets. A convenient pantry and a half bath are nearby, along with a door leading to the back of the house. Access to the full basement is here as well. The wonderful, covered wrap-around porch is a true highlight. Its spaciousness and fabulous adjustable glass blinds allow you to control the temperature, ensuring comfortable outdoor gatherings year-round. On a side of the house there is a stone patio offering another gathering spot. Five cheerful bedrooms are on the second level, each with its own unique character. One bedroom features a Juliet balcony and a private sink. This level also includes a full bath and an additional half bath. Should you desire an en-suite primary bedroom, a smaller adjacent bedroom presents a logical and convenient spot for adding an additional bathroom. Situated on a double lot, this property offers ample space to add a swimming pool, should you desire. Enjoy leisurely strolls into Callicoon, with its fantastic selection of shops, restaurants, and the classic Callicoon Theater. The scenic Delaware River is also just steps away. All this, conveniently located only 2.5 hours from New York City.
Courtesy: Country House Realty Inc
845-397-2590
This charming 2bed/2.5-bath home strikes the perfect balance between comfort and character the moment you step inside. The main living area is open and flowing, with a relaxed seating area on one side where you can kick back and take in the peaceful views over the lovely open field in the front yard. A sliding door invites you out to the large screened-in porch - the perfect spot for morning coffee, summer dining room or an evening wind-down. On the other side, the dining area and kitchen work beautifully together as an entertainer's dream. With a Frigidaire range at the helm, you'll have no trouble hosting jovial dinner parties while guests admire your cheffing skills. A generous built-in storage wall anchors one end, doing double duty as a well-organized pantry. The first bedroom is conveniently located on this level, and shares a stylish jack-and-jill bathroom, glass enclosed shower, charming hexagon-tiled floors, and classic subway tile walls. Upstairs, a versatile landing offers real potential — whether you envision a home office or a third bedroom is entirely up to you. Built-in storage and closet space make it practical either way. The second bedroom is a true retreat, featuring soaring vaulted ceilings, two skylights that flood the space with natural light, a closet, and a private en-suite bathroom with a walk-in shower. The basement rounds out the home beautifully. Gather for movie nights in the cozy den, keep laundry tucked away with the washer/dryer, and take advantage of the overflow sleeping area for guests. The unfinished portion offers substantial storage space, with a Bilco door providing convenient backyard access — and a half bath completes the level. Step outside and the wraparound deck and screened-in area truly impress — built with mahogany, one of the most durable and premium decking materials available. The 5.65 acres offer the best of both worlds: a peaceful wooded area and a flat, open grassy field. The long, tree-lined driveway sets the tone perfectly — every arrival home feels like a small event. The location is hard to beat. Seminary Hill Cidery, celebrated for its award-winning cider, stunning views, and excellent dining, is just a 5-minute walk away. A 2-minute drive brings you into the heart of Callicoon, where you'll find beloved restaurants like Black Walnut and The Creek House Grill, an art deco movie theater, the charming Callicoon Wine Merchant, gourmet spots like Spruce and Callicoon Pantry, exceptional bread from Roger That, and the region's finest farmers market. Kayak, fish and swim on the Upper Delaware River, with multiple access points near town.
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: 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
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: Land and Water Realty LLC
845-807-2630
There is new construction to make a quick buck, and there is new construction that is thoughtfully designed and pridefully constructed to create a home that can last a lifetime. This modern home with an elegant, rustic twist is certainly the latter and just what you are looking for if you want a home combining simplicity with soul. That blend is difficult to get right but here that marriage of modern simplicity with raw, authentic soul is absolutely perfected. You have a total of 3 beds and 2 full baths with a master suite that has a private bathroom and an extra-large walk-in closet. The open floor plan is ideal for entertaining friends without feeling congested. There are large Anderson glass windows and sliding doors with southwestern exposure leading to the full-length deck. Walking out on the deck to the setting sun with an evening beverage might be just what the doctor ordered to escape the fast-paced, obscure digital world, if even for just a moment. A full walk-out basement can easily be finished to create additional living space, should it be necessary. This is not some Home Cheapo construction; every finish and every detail was hand-picked from top brands to perfectly fit this curated masterpiece. You really won't want to miss an opportunity to make this place your own. Set on 5+ acres in an oak forest, you will have a feeling of community but with enough elbow room to feel privately secluded. Minutes to Callicoon, and less than a mile from the hospital, you have all the creature comforts you can ask for in a community where strangers still wave at each other, and people still smile as you walk past them on the street. This home is truly fitting for its location. Highly regarded as one of the best small towns in America, Callicoon, NY offers a historic main street with a thriving, year-round farmers market, vintage shops, and cafes. Whether it is food and drinks at the Creekhouse Grill, Seminary Hill Cidery, or the Black Walnut, a night at the movie theater, or a day at the famous tractor parade, you will feel it in your bones that this place is what life is really all about. Do not wait, schedule your showing today.
Courtesy: Country House Realty Inc
845-397-2590
Set among the bucolic rolling hills of Callicoon on a half acre, Farmview Chalet is a wonderful opportunity for a buyer looking for a project with some of the dirty work already done. Gutted to the studs and ready for build out, roll up your sleeves and make this magical little chalet come to life. Entering the house, you’re greeted by a living room with a brick fireplace as a charming focal point. It’s easy to see nights spent fireside on your vision board, and to let the house grow from there. A staircase with decorative spindles divides the lower level logically and also provides some architectural intrigue. On the far side of the staircase, a light and bright rear room open up. This could be a dining space or kitchen - both would be great choices to soak up the southern light that pours in year-round. Adjacent, you’ll find the full bathroom ready for its new life. Upstairs, there are two bedrooms on the front and back of the home, including the charming juliet balcony overlooking the neighboring farm fields. Need a little extra room? Perhaps a dormer and a primary bathroom could be just the right idea. Whatever you choose, with the space totally opened up, you’ll be able to see all the available options easily. Located only 5 minutes from Callicoon, and 10 from Jeffersonville - Farmview Chalet is in a sweet spot in western Sullivan County. It’s rare to find a project like this, in a location like this, with a price like this. Don’t dilly dally - come make it your very own HGTV moment. AI-assisted imagery included in the listing to get the ideas flowing.
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
Courtesy: Matthew J Freda Real Estate
845-887-5640
Life in the Callicoon Catskills doesn’t get any better than this fine 2 bedroom brick ranch home surrounded by a level lawn and mature trees in a park-like setting. Easily accessed by a paved driveway which leads to a heated 2 car garage and breezeway. Inside find a well-designed kitchen with a comfortable dining room. The living room has a brick fireplace and a large picture window to enjoy nature. 2 large bedrooms and 1 full bath complete the first floor. Need space for hobbies or watching TV? Downstairs find a finished basement with family room/den with a large cedar closet (7.5x7.5), utility area with washer/dryer and a laundry chute. Home comes furnished-just move right in! Many upgrades to home include roof, furnace and energy efficient windows, making this a very comfortable home. Property consists of .73 acre which consists of two lots. Conveniently set and located on Route 97, a well-maintained paved road, only 1 mile from the Hamlet of Callicoon which boasts many stores and restaurants, and the Delaware River. Other nearby attractions are the Bethel Woods Performing Arts Center/Original Woodstock site, Roscoe, NY for trout fishing and many Catskills trout streams.
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.
