Callicoon Real Estate

Welcome to Callicoon, New York – a hidden gem nestled in the heart of Sullivan County! Known for its picturesque landscapes and charming small-town vibe, Callicoon offers a unique blend of rustic beauty and vibrant community spirit. This quaint town is strategically located along the banks of the Delaware River, providing residents with stunning views and a plethora of outdoor activities.

With its rich history dating back to the 19th century, Callicoon boasts a delightful mix of historical architecture and modern amenities. Stroll through the charming streets lined with boutique shops, cozy cafes, and artisanal markets, where you can find everything from handcrafted goods to local delicacies. The town's friendly atmosphere invites you to engage with neighbors and become part of a close-knit community.

Nature enthusiasts will find Callicoon to be a paradise. The surrounding Catskill Mountains offer endless opportunities for hiking, fishing, and kayaking. In the fall, the vibrant foliage creates a breathtaking backdrop for outdoor adventures. Additionally, the nearby Bethel Woods Center for the Arts hosts a variety of concerts and cultural events, ensuring that there's always something exciting happening in and around Callicoon.

Whether you’re seeking a tranquil retreat or a place to call home, Callicoon’s charm and natural beauty make it an ideal destination. Experience the warmth of this delightful town and discover why so many are drawn to its serene lifestyle. Come explore Callicoon – where community, nature, and history come together in perfect harmony!

Newest Listings in Callicoon

$950,000

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

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

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

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

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

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

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

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

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

1017550 MLS

28 Upper Main Street, Callicoon

$40,000

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

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

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