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$950,000

Exceptional Commercial Investment Opportunity in the Heart of Callicoon A rare opportunity to own two income-producing properties in the highly sought-after hamlet of Callicoon, one of the most popular Delaware River towns in the Catskills. This offering consists of two separate properties: 33 Lower Main Street and 30A Dorrer Drive, Callicoon, NY. 33 Lower Main Street features two commercial storefronts. One is currently occupied by a popular café serving breakfast and lunch, while the second is leased as professional office space. 30A Dorrer Drive, ideally located near Callicoon’s popular farmers market, is a mixed-use property offering both commercial and residential income. The commercial space is currently leased to a wine shop, while a separate apartment above is also currently leased. Also included is the land situated between 33 Lower Main Street and 30A Dorrer Drive, currently utilized as additional outdoor dining space, adding further versatility and value to the offering. Callicoon enjoys exceptional foot traffic and a steady flow of visitors drawn to its restaurants, shops, farmers market, entertainment, and Delaware River setting. With multiple existing tenants and a prime location in the center of town, this is an excellent opportunity for an investor looking to acquire a unique commercial and mixed-use property in one of Sullivan County’s most desirable destinations. Multiple income streams. Two distinct properties. Prime Callicoon location.

1049608 MLS

Exceptional Commercial Investment Opportunity in the Heart of Callicoon A rare opportunity to own two income-producing properties in the highly sought-after hamlet of Callicoon, one of the most popular Delaware River towns in the Catskills. This offering consists of two separate properties: 33 Lower Main Street and 30A Dorrer Drive, Callicoon, NY. 33 Lower Main Street features two commercial storefronts. One is currently occupied by a popular café serving breakfast and lunch, while the second is leased as professional office space. 30A Dorrer Drive, ideally located near Callicoon’s popular farmers market, is a mixed-use property offering both commercial and residential income. The commercial space is currently leased to a wine shop, while a separate apartment above is also currently leased. Also included is the land situated between 33 Lower Main Street and 30A Dorrer Drive, currently utilized as additional outdoor dining space, adding further versatility and value to the offering. Callicoon enjoys exceptional foot traffic and a steady flow of visitors drawn to its restaurants, shops, farmers market, entertainment, and Delaware River setting. With multiple existing tenants and a prime location in the center of town, this is an excellent opportunity for an investor looking to acquire a unique commercial and mixed-use property in one of Sullivan County’s most desirable destinations. Multiple income streams. Two distinct properties. Prime Callicoon location.

33 Lower Main Street, Callicoon

$596,500

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.

4 Beds ⋅ 2 Baths ⋅ 1050796 MLS

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.

519 Route 164, Callicoon

$485,000

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.

3 Beds ⋅ 2 Baths ⋅ 1048306 MLS

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.

22 Mill Street, Callicoon

$179,900

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.

2 Beds ⋅ 2 Baths ⋅ 1045360 MLS

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.

4 Joe D Drive Unit #4C, Callicoon

$1,450,000

Welcome to the Beechwoods, a disarmingly bucolic pocket of Sullivan County where cattle laze beside a stream and sheep forage across rolling hills. Here, in the agrarian calm high above Callicoon, the Beechwoods House looks out across what is surely one of the most beautiful views in all the Catskills: 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 panorama, with its main living spaces facing west toward the sunset. Although custom built in 2022, the house feels as though it has stood here for generations. Weathered wood, radiant heated cobblestone floors and rooms filled with patina give it the soul of an old Catskills homestead. Its open layout and connection to the outdoors are distinctly modern. At the center is an expansive living room anchored by a sleek gas fireplace and oversized hearth. Wood wrapped walls and ceilings create an enveloping warmth, while broad windows frame the countryside. A built in nook offers a cozy corner for reading. Doors open to outdoor spaces on two sides. One looks west across the hills, an idyllic setting for dinner as light moves over the valley. The other is an intimate retreat surrounded by native plantings. In summer, open both sides to let the breeze and birdsong move through the house. In winter, heated stone floors and fireside seating make it wonderfully cocooning. The kitchen has the collected character of a French country house, with wood cabinetry, open shelving, skirted worktables, an apron front sink and patinated materials. There is room for a dining table overlooking the landscape. A mudroom, laundry area and half bath sit beyond, while a separate terrace creates another place for morning coffee. The bedrooms extend along two wings for a natural sense of privacy. 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 wing. A concealed stairway leads to one of the home’s most unexpected spaces: a generous loft beneath the pitched roof. Warm wood ceilings follow the roofline, while windows bring in light and treetop views. It feels like a private world of its own, equally suited to a screening room, library, studio, home office or guest suite. Outside, covered terraces, slatted pergolas and garden paths give way to meadow alive with grasses and wildflowers. Adirondack chairs at the edge of the hill invite you to take in the western view. The property feels wonderfully private yet expansive, with the house almost hidden within the landscape. Despite its seclusion, the Beechwoods is just ten minutes from Callicoon. Visit the farmers’ market, Callicoon Wine Merchant, Black Walnut or the historic Callicoon Theater. Nearby Seminary Hill offers cider, food and views across the Delaware River Valley. The river invites swimming, kayaking, tubing and fishing throughout the warmer months. Ten minutes away, Jeffersonville is home to Sullivan Sundries, a destination for coffee, provisions and home goods. Bethel Woods brings concerts and festivals to the historic Woodstock site, while Narrowsburg, Livingston Manor and Roscoe offer restaurants, breweries, antiquing and fly fishing. Just 2.5 hours from New York City, 506 Beechwoods offers a rare combination of deep quiet and genuine connection. Offered furnished, its layered interiors feel immediately inviting: removed from everything when you want to be, with some of the Catskills’ best food, culture and small town life close at hand.

4 Beds ⋅ 3 Baths ⋅ 1046659 MLS

Welcome to the Beechwoods, a disarmingly bucolic pocket of Sullivan County where cattle laze beside a stream and sheep forage across rolling hills. Here, in the agrarian calm high above Callicoon, the Beechwoods House looks out across what is surely one of the most beautiful views in all the Catskills: 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 panorama, with its main living spaces facing west toward the sunset. Although custom built in 2022, the house feels as though it has stood here for generations. Weathered wood, radiant heated cobblestone floors and rooms filled with patina give it the soul of an old Catskills homestead. Its open layout and connection to the outdoors are distinctly modern. At the center is an expansive living room anchored by a sleek gas fireplace and oversized hearth. Wood wrapped walls and ceilings create an enveloping warmth, while broad windows frame the countryside. A built in nook offers a cozy corner for reading. Doors open to outdoor spaces on two sides. One looks west across the hills, an idyllic setting for dinner as light moves over the valley. The other is an intimate retreat surrounded by native plantings. In summer, open both sides to let the breeze and birdsong move through the house. In winter, heated stone floors and fireside seating make it wonderfully cocooning. The kitchen has the collected character of a French country house, with wood cabinetry, open shelving, skirted worktables, an apron front sink and patinated materials. There is room for a dining table overlooking the landscape. A mudroom, laundry area and half bath sit beyond, while a separate terrace creates another place for morning coffee. The bedrooms extend along two wings for a natural sense of privacy. 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 wing. A concealed stairway leads to one of the home’s most unexpected spaces: a generous loft beneath the pitched roof. Warm wood ceilings follow the roofline, while windows bring in light and treetop views. It feels like a private world of its own, equally suited to a screening room, library, studio, home office or guest suite. Outside, covered terraces, slatted pergolas and garden paths give way to meadow alive with grasses and wildflowers. Adirondack chairs at the edge of the hill invite you to take in the western view. The property feels wonderfully private yet expansive, with the house almost hidden within the landscape. Despite its seclusion, the Beechwoods is just ten minutes from Callicoon. Visit the farmers’ market, Callicoon Wine Merchant, Black Walnut or the historic Callicoon Theater. Nearby Seminary Hill offers cider, food and views across the Delaware River Valley. The river invites swimming, kayaking, tubing and fishing throughout the warmer months. Ten minutes away, Jeffersonville is home to Sullivan Sundries, a destination for coffee, provisions and home goods. Bethel Woods brings concerts and festivals to the historic Woodstock site, while Narrowsburg, Livingston Manor and Roscoe offer restaurants, breweries, antiquing and fly fishing. Just 2.5 hours from New York City, 506 Beechwoods offers a rare combination of deep quiet and genuine connection. Offered furnished, its layered interiors feel immediately inviting: removed from everything when you want to be, with some of the Catskills’ best food, culture and small town life close at hand.

506 Beechwoods Road, Callicoon

$85,000

Discover the opportunity to create your own private retreat on this beautiful 2.15-acre residential parcel located at 32 Conroy Road in Callicoon, NY. Set along a quiet, private road, this property offers a peaceful setting surrounded by the natural beauty of Sullivan County. With over two acres of land, there is plenty of potential to design and build the home you've been dreaming of—whether you envision a charming country home, a modern weekend escape, or a year-round residence surrounded by nature. Enjoy privacy, space, and the tranquility of country living while creating a property tailored to your lifestyle. A wonderful opportunity for buyers, builders, or investors looking for residential land in the desirable Callicoon area. Bring your vision and explore the possibilities this property has to offer.

1043366 MLS

Discover the opportunity to create your own private retreat on this beautiful 2.15-acre residential parcel located at 32 Conroy Road in Callicoon, NY. Set along a quiet, private road, this property offers a peaceful setting surrounded by the natural beauty of Sullivan County. With over two acres of land, there is plenty of potential to design and build the home you've been dreaming of—whether you envision a charming country home, a modern weekend escape, or a year-round residence surrounded by nature. Enjoy privacy, space, and the tranquility of country living while creating a property tailored to your lifestyle. A wonderful opportunity for buyers, builders, or investors looking for residential land in the desirable Callicoon area. Bring your vision and explore the possibilities this property has to offer.

32 Conroy Road, Callicoon

$749,999

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

7 Beds ⋅ 4 Baths ⋅ 1040279 MLS

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

28 Upper Main Street, Callicoon

$989,000

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,

4 Beds ⋅ 4 Baths ⋅ 1030710 MLS

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,

32 Long Farm Way, Callicoon

$769,000

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.

3 Beds ⋅ 2 Baths ⋅ 1021417 MLS

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.

204 Country Road, Callicoon

$749,999

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

1017550 MLS

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

28 Upper Main Street, Callicoon

$40,000

This 0.82 acre property has Beechwoods Rd address, however, access is through ROW. Trailer has been removed and old barn and storage building remain. Both are filled with wood, metal, doors, etc. Mobile home was removed some years back but another mobile home could be placed here again. There is shallow well and there was septic. No representations made as to condition of well or septic. Cash sale only, in "as is" condition.

1014395 MLS

This 0.82 acre property has Beechwoods Rd address, however, access is through ROW. Trailer has been removed and old barn and storage building remain. Both are filled with wood, metal, doors, etc. Mobile home was removed some years back but another mobile home could be placed here again. There is shallow well and there was septic. No representations made as to condition of well or septic. Cash sale only, in "as is" condition.

16 Beechwoods Road, Callicoon

$74,990

7.97 Acres for Sale in the Sullivan Catskills – Build Your Dream Home in the Beechwoods Discover nearly 8 acres of beautiful Catskills land in the highly desirable Beechwoods area of Sullivan County, New York. This lightly wooded 7.97-acre parcel offers the perfect blend of privacy, natural beauty, and development potential for buyers seeking a future homesite, country retreat, vacation property, or full-time residence. The property features a diverse mix of mature hardwoods and evergreens, established blueberry bushes, and an attractive site for a potential pond. Adding to its unique character is the historic stone foundation of a former local landmark, offering a glimpse into the rich history of the Catskills. With gently rolling terrain and multiple possibilities for building, this property is ideal for those searching for land to build a custom home, weekend getaway, cabin, or homestead. Enjoy the peace and tranquility of nature while remaining close to the area's most sought-after destinations, including Bethel Woods, Callicoon, Livingston Manor, Jeffersonville, Narrowsburg, hiking trails, fishing, kayaking, farmers' markets, and year-round outdoor recreation. Located less than two hours from New York City, Sullivan County continues to attract buyers looking for privacy, fresh mountain air, lower taxes, and a connection to nature without sacrificing accessibility.

1011401 MLS

7.97 Acres for Sale in the Sullivan Catskills – Build Your Dream Home in the Beechwoods Discover nearly 8 acres of beautiful Catskills land in the highly desirable Beechwoods area of Sullivan County, New York. This lightly wooded 7.97-acre parcel offers the perfect blend of privacy, natural beauty, and development potential for buyers seeking a future homesite, country retreat, vacation property, or full-time residence. The property features a diverse mix of mature hardwoods and evergreens, established blueberry bushes, and an attractive site for a potential pond. Adding to its unique character is the historic stone foundation of a former local landmark, offering a glimpse into the rich history of the Catskills. With gently rolling terrain and multiple possibilities for building, this property is ideal for those searching for land to build a custom home, weekend getaway, cabin, or homestead. Enjoy the peace and tranquility of nature while remaining close to the area's most sought-after destinations, including Bethel Woods, Callicoon, Livingston Manor, Jeffersonville, Narrowsburg, hiking trails, fishing, kayaking, farmers' markets, and year-round outdoor recreation. Located less than two hours from New York City, Sullivan County continues to attract buyers looking for privacy, fresh mountain air, lower taxes, and a connection to nature without sacrificing accessibility.

00 Polster, Callicoon

$439,000

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.

4 Beds ⋅ 2 Baths ⋅ 1010333 MLS

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.

58 Polster Road, Callicoon

$349,000

Welcome to this immaculate Beechwood Estates II condominium townhouse in Callicoon's Beechwoods hills. Pride of ownership is visible throughout. A 3 bedroom, living/dining room, eat-in kitchen, 2 full baths, and a covered porch with an open deck offer lots of space for the weekend warriors or full time residents. The attached garage and the fully finished basement with a half bath complete the picture. There is an LP operated full house generator; an alarm system; an alarm for the hot water heater, and a built-in dehumidifier in the finished basement. Enjoy golf at the Villa Roma Resort's 18 hole golf course and shop and dine at the wonderful shops and eateries you will find in Callicoon, Jeffersonville and Livingston Manor. This is a 4-season home in New York's Catskills which allows many city dwellers to cope with another busy city week. Come and take a look!

3 Beds ⋅ 3 Baths ⋅ 1010833 MLS

Welcome to this immaculate Beechwood Estates II condominium townhouse in Callicoon's Beechwoods hills. Pride of ownership is visible throughout. A 3 bedroom, living/dining room, eat-in kitchen, 2 full baths, and a covered porch with an open deck offer lots of space for the weekend warriors or full time residents. The attached garage and the fully finished basement with a half bath complete the picture. There is an LP operated full house generator; an alarm system; an alarm for the hot water heater, and a built-in dehumidifier in the finished basement. Enjoy golf at the Villa Roma Resort's 18 hole golf course and shop and dine at the wonderful shops and eateries you will find in Callicoon, Jeffersonville and Livingston Manor. This is a 4-season home in New York's Catskills which allows many city dwellers to cope with another busy city week. Come and take a look!

7 Villa Vista Drive Unit #702, Callicoon

$355,000

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!

3 Beds ⋅ 2 Baths ⋅ 1005698 MLS

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!

12 Mesmer, Callicoon

$399,900

stunning building lot with plenty of room to grow. Long distance views, fields meadows and starry night skys. Unimproved raw land on the edge of a farm.

1004370 MLS

stunning building lot with plenty of room to grow. Long distance views, fields meadows and starry night skys. Unimproved raw land on the edge of a farm.

301 & 305 Hust Road Hust, Callicoon

$670,000

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.

3 Beds ⋅ 3 Baths ⋅ 1003008 MLS

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.

340 Hospital Road, Callicoon

$1,048,000

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.

4 Beds ⋅ 4 Baths ⋅ 993379 MLS

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.

63 Sky View Drive, Callicoon

$444,000

Price reduction and offer of $20k credit plus new furnace! This 26.43 acre parcel of land features a home with 2 bedrooms, 2 full baths, and a spacious loft area that serves as the 3rd bedroom. The sunny, bright great room has a cathedral ceiling. There is a full basement and a one car garage underneath. You will also find a shed and a lovely pond where only the ducks are missing! House and deck will need some TLC, and the seller is offering a $20,000 credit at closing. Seller will also replace the furnace before closing. Come and take a look and present all offers! This could be your ideal get-away from city stress if you apply some elbow grease. This is a delightful rural location for kids to ride bikes or for you to jog or walk. Pack a picnic and hike down to the creek to enjoy a dip in the water and a luncheon al fresco. There is a second clearing along W Simmon, together with substantial road frontage to subdivide or build another home. It is 10 minutes to downtown Callicoon with its eateries, shopping, entertainment, Delaware River activities and Sunday Farmers Market. Or 10 minutes to Roscoe to fly fish in your favorite streams!

2 Beds ⋅ 2 Baths ⋅ 983165 MLS

Price reduction and offer of $20k credit plus new furnace! This 26.43 acre parcel of land features a home with 2 bedrooms, 2 full baths, and a spacious loft area that serves as the 3rd bedroom. The sunny, bright great room has a cathedral ceiling. There is a full basement and a one car garage underneath. You will also find a shed and a lovely pond where only the ducks are missing! House and deck will need some TLC, and the seller is offering a $20,000 credit at closing. Seller will also replace the furnace before closing. Come and take a look and present all offers! This could be your ideal get-away from city stress if you apply some elbow grease. This is a delightful rural location for kids to ride bikes or for you to jog or walk. Pack a picnic and hike down to the creek to enjoy a dip in the water and a luncheon al fresco. There is a second clearing along W Simmon, together with substantial road frontage to subdivide or build another home. It is 10 minutes to downtown Callicoon with its eateries, shopping, entertainment, Delaware River activities and Sunday Farmers Market. Or 10 minutes to Roscoe to fly fish in your favorite streams!

10 W Simmon, Callicoon

$379,000

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.

5 Beds ⋅ 2 Baths ⋅ 982483 MLS

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.

11 Highview Avenue, Callicoon

$259,000

Welcome to 21.77 picturesque acres in the heart of Callicoon, NY—an exceptional piece of residential ACG-zoned land offering a rare combination of privacy, accessibility, and breathtaking natural beauty. With three distinct entry points, this expansive parcel provides flexible access options and endless potential for your Catskills dream property. The land itself is a blend of gently rolling terrain, low-lying clearings, and higher elevation areas that level off to reveal sweeping mountain views—perfect for siting a future home, guest cabins, or a private retreat. A serene stream meanders through the property, adding to the peaceful, untouched feel of the landscape. Whether you're looking to build a full-time residence, a weekend getaway, or explore sustainable homesteading or small-scale agricultural pursuits, this property offers the versatility to do it all. Zoned Residential ACG (Agricultural-Conservation-Residential), this land allows for a variety of uses including single-family homes, small farms, gardens, greenhouses, and accessory structures. The acreage offers more than enough room for privacy, creative design, and even potential subdivision with proper approvals. Located just minutes from the charming hamlet of Callicoon, you’ll find a vibrant local community with a weekly farmers market, boutique shops, art galleries, and farm-to-table dining. Outdoor enthusiasts will enjoy nearby access to the Delaware River for kayaking, tubing, and fishing. Bethel Woods Center for the Arts—site of the original Woodstock Festival—is just a short drive away, offering concerts, festivals, and cultural events year-round. Tax Map # 3.-1-3.1

982781 MLS

Welcome to 21.77 picturesque acres in the heart of Callicoon, NY—an exceptional piece of residential ACG-zoned land offering a rare combination of privacy, accessibility, and breathtaking natural beauty. With three distinct entry points, this expansive parcel provides flexible access options and endless potential for your Catskills dream property. The land itself is a blend of gently rolling terrain, low-lying clearings, and higher elevation areas that level off to reveal sweeping mountain views—perfect for siting a future home, guest cabins, or a private retreat. A serene stream meanders through the property, adding to the peaceful, untouched feel of the landscape. Whether you're looking to build a full-time residence, a weekend getaway, or explore sustainable homesteading or small-scale agricultural pursuits, this property offers the versatility to do it all. Zoned Residential ACG (Agricultural-Conservation-Residential), this land allows for a variety of uses including single-family homes, small farms, gardens, greenhouses, and accessory structures. The acreage offers more than enough room for privacy, creative design, and even potential subdivision with proper approvals. Located just minutes from the charming hamlet of Callicoon, you’ll find a vibrant local community with a weekly farmers market, boutique shops, art galleries, and farm-to-table dining. Outdoor enthusiasts will enjoy nearby access to the Delaware River for kayaking, tubing, and fishing. Bethel Woods Center for the Arts—site of the original Woodstock Festival—is just a short drive away, offering concerts, festivals, and cultural events year-round. Tax Map # 3.-1-3.1

000 Kautz Road, Callicoon

$2,750,000

Unique offering! This 9-lot subdivision can make serious developers/ builders a fortune! Package consists of two beautiful upscale modern farmhouses, one is complete and one is in progress, the original 1890’s farmhouse which has been tastefully updated, two barns, PLUS 6 shovel-ready lots. The two homes are ready to be sold immediately if you choose, or establish this community as your own estate with guest homes and recreational opportunities, or an upscale exclusive community with amenities. This distinctive rural development is in Callicoon NY on just over 60 acres with homesites ranging from 4 to 12 acres. The sites are the perfect size to be able to garden, explore and really enjoy the beautiful country lifestyle. Each parcel is strategically situated for the best exposure, views, and privacy. Homesites are approved, shovel ready, engineered, and ready to go. This developer got involved in another project and is very willing to share the vision which was for the original farmhouse with barns and pond to be a hub for numerous amenities for the residents in the development. The SUGi Project, a global organization that conceives, plans and funds pocket forests all over the world and looks to protect biodiversity, restore ecosystems, and even better reconnect people to nature, was also consulted during the planning process. Plans and vision for creating a pocket forest can also be shared with the purchaser. Private road to interior lots is cut in and some lots offer the possibility of a walk-out basement and/ or a pond site. Underground electricity and cable are in the works. 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.

971998 MLS

Unique offering! This 9-lot subdivision can make serious developers/ builders a fortune! Package consists of two beautiful upscale modern farmhouses, one is complete and one is in progress, the original 1890’s farmhouse which has been tastefully updated, two barns, PLUS 6 shovel-ready lots. The two homes are ready to be sold immediately if you choose, or establish this community as your own estate with guest homes and recreational opportunities, or an upscale exclusive community with amenities. This distinctive rural development is in Callicoon NY on just over 60 acres with homesites ranging from 4 to 12 acres. The sites are the perfect size to be able to garden, explore and really enjoy the beautiful country lifestyle. Each parcel is strategically situated for the best exposure, views, and privacy. Homesites are approved, shovel ready, engineered, and ready to go. This developer got involved in another project and is very willing to share the vision which was for the original farmhouse with barns and pond to be a hub for numerous amenities for the residents in the development. The SUGi Project, a global organization that conceives, plans and funds pocket forests all over the world and looks to protect biodiversity, restore ecosystems, and even better reconnect people to nature, was also consulted during the planning process. Plans and vision for creating a pocket forest can also be shared with the purchaser. Private road to interior lots is cut in and some lots offer the possibility of a walk-out basement and/ or a pond site. Underground electricity and cable are in the works. 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.

356 Gabel Road, Callicoon

$1,350,000

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.

6 Beds ⋅ 4 Baths ⋅ 970019 MLS

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.

91 Old Hankins Road, Callicoon

$649,000

Discover the allure of 23.6 panoramic acres in the highly desirable Beechwoods section of Callicoon, boasting breathtaking long-range views that stretch as far as the eye can see. This picturesque expanse of land presents a once-in-a-lifetime opportunity to create your estate.

947294 MLS

Discover the allure of 23.6 panoramic acres in the highly desirable Beechwoods section of Callicoon, boasting breathtaking long-range views that stretch as far as the eye can see. This picturesque expanse of land presents a once-in-a-lifetime opportunity to create your estate.

04 Bauernfiend Road, Callicoon

$243,750

This 7.5+- acre Beechwoods lot provides a secluded open field, wooded terrain, valley views, and a possible pond site. Just minutes to Jeffersonville and Callicoon, located on a sparsely traveled town road.

947292 MLS

This 7.5+- acre Beechwoods lot provides a secluded open field, wooded terrain, valley views, and a possible pond site. Just minutes to Jeffersonville and Callicoon, located on a sparsely traveled town road.

Bauernfeind Road, Callicoon

$759,000

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

3 Beds ⋅ 2 Baths ⋅ 925634 MLS

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

48 Upper Main Street, Callicoon

$759,000

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

925171 MLS

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

48 Upper Main Street, Callicoon

$275,000

Own a stunning 7.4-acre property with panoramic views in the highly desirable Beechwoods section of Callicoon. Build your dream home and embrace the beauty of nature. Don't miss this incredible opportunity!

901475 MLS

Own a stunning 7.4-acre property with panoramic views in the highly desirable Beechwoods section of Callicoon. Build your dream home and embrace the beauty of nature. Don't miss this incredible opportunity!

Beechwoods Road, Callicoon

$899,000

Callicoon, New York - 5 acre commercial property with 1400 feet of stream front on the Callicoon Creek. Located on NYS RT 17B and next to NYS Rt 97, this is a high traffic/highly visible location. The access for trucks and vehicular traffic is level and provides easy access for loading, unloading and doing business. Currently used as an automotive repair facility, it consists of 4 buildings, large parking area. Main building is 20,000+/- SF consisting of 3 furnaces, 3 phase electric, 5 lifts. 16' high ceilings-many large overhead doors, 2 large garage service areas, body shop with spray booth, lobby entrance, plus many office rooms on 1st & 2nd floor. Building 2 is the tire storage shed (108x45), Building 3 is the vehicle storage garage (45x102), Building 4 is 24x45 and is used for storage. Great level location, 1400 ft on NYS Route 17B and at the intersection of NYS Route 97 - a high traffic location. Let your imagination be your guide, from automotive and industrial to retail sales. This is the gateway to Pennsylvania and the bustling Hamlet of Callicoon on the Delaware River.

810848 MLS

Callicoon, New York - 5 acre commercial property with 1400 feet of stream front on the Callicoon Creek. Located on NYS RT 17B and next to NYS Rt 97, this is a high traffic/highly visible location. The access for trucks and vehicular traffic is level and provides easy access for loading, unloading and doing business. Currently used as an automotive repair facility, it consists of 4 buildings, large parking area. Main building is 20,000+/- SF consisting of 3 furnaces, 3 phase electric, 5 lifts. 16' high ceilings-many large overhead doors, 2 large garage service areas, body shop with spray booth, lobby entrance, plus many office rooms on 1st & 2nd floor. Building 2 is the tire storage shed (108x45), Building 3 is the vehicle storage garage (45x102), Building 4 is 24x45 and is used for storage. Great level location, 1400 ft on NYS Route 17B and at the intersection of NYS Route 97 - a high traffic location. Let your imagination be your guide, from automotive and industrial to retail sales. This is the gateway to Pennsylvania and the bustling Hamlet of Callicoon on the Delaware River.

4587 State Route 17b, Callicoon