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$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

$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

$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

$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

$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

$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

$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

$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