Courtesy: Century 21 Country Realty
845-791-5280
Enjoy space, scenery, and easy access to the best of the Sullivan Catskills with this well-maintained 3-bedroom, 2-bath mobile home set on 4.42 acres. The home features a large living room, comfortable layout, and plenty of room to relax indoors or out. A spacious deck accented by natural wood and stone invites you to take in the beautiful views and enjoy quiet mornings, outdoor meals, or evenings surrounded by nature. With over four acres, the property offers ample space for gardening, recreation, pets, gatherings, or simply enjoying the peaceful setting. Outdoor enthusiasts will love the location, with convenient access to the Delaware River area, Callicoon, and Roscoe. Nearby attractions include fly fishing, river activities, hiking, scenic drives, local shops, and a variety of well-loved restaurants throughout the region. Whether you are looking for a full-time residence, weekend getaway, or Catskills-area retreat, this property offers the combination of usable acreage, natural beauty, and proximity to recreation that makes country living so appealing.
Courtesy: Anatole House LLC
845-943-4177
Hollyhock sits a long way back from a quiet country road on 10.13 acres of meadow, woods, and historic stone walls. The house is properly private and still only a few minutes from Livingston Manor's main street, which is the increasingly rare combination people drive up here to find. The interiors are where it gets interesting: someone has been making confident, pattern-loving, vintage-respecting decisions in every room, and the result is a house with actual personality. The first floor flows in a loop you'll want to walk twice. The living room is bright and white with raised panel wainscoting, a cast-iron woodstove on a stone hearth, a salon-style cluster of art, and enough plants on the chair rail to make a casual nursery. It opens straight into the kitchen, which has been redone with new appliances, stone countertops, greige cabinets, and open shelving to show off your ceramics and a rainbow of Le Creuset. Off the kitchen, the dining room goes fully committed: floral wallpaper above buttery yellow wainscoting, a yellow tray ceiling with a stenciled border, dark plank floors, and the most precious pendant light you ever did see. A library waits wrapped in deep blue-green walls with floor-to-ceiling built-in bookshelves, a vinyl listening zone, and enough seating to ride out a long rainy weekend. A floral-papered powder room rounds out the main level. Upstairs is more restrained on purpose. The primary bedroom is calm and pale with framed botanical prints and an en suite full bath. Two additional bedrooms share the second full bath. The office sits in its own corner with a gallery wall of eclectic art and the kind of striped wingback chair that suggests reading more than answering emails. A full basement is ready for whatever you've got planned: gym, workshop, wine cellar, ambitious art project. Outside, historic stone walls thread through meadows that were clearly tended by someone who cared. The deep setback from the road is the kind you actually feel: you can sit on the new front porch without making eye contact with a single passing car. The back deck is generous and multi-level, with built-in bench seating that doubles as low planters, plus room for a dining table, lounge, and grill. And not to be missed: the mowed paths wandering through the back meadow, just past the fire pit. Livingston Manor's main street is five minutes down the road, where Upward Brewing Company pours an excellent lager and Kaatskeller turns out wood-fired pizza worth the drive on its own. Main Street Farm provides excellent local groceries and takeaway sandwiches. For walking it all off, the Frick Pond Trail in the Willowemoc Wild Forest offers a manageable loop through hemlocks and beaver ponds, all about twenty minutes from the front door.
Courtesy: Country House Realty Inc
845-397-2590
Enjoy the convenience of in-town living at this newly gut renovated brick ranch in Jeffersonville, NY. Bright, airy, easy single floor living with modern upgrades make this a great family home, or potential investment as a rental property. Fully renovated in 2023, the home features a brand new kitchen, bathroom, windows, hot water heater, and back deck. There are three ground floor bedrooms and full bathroom, as well as the large eat-in kitchen, and sun drenched living room with stone fireplace with new woodstove insert. There is a full basement with laundry and half bath with potential for finishing. Single attached garage adds to the convenience whether used for your vehicle or additional storage or workspace. One block from Main St. Jeffersonville, but set on a quiet dead-end road, owners can enjoy a short walk to grab a coffee at Sullivan Sundries, pick up groceries at Pecks, or grab dinner at Tavern on Main. Don't miss this one. Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:1 Car Attached,
Courtesy: Country House Realty Inc
845-397-2590
Welcome to Flats Modern — a beautifully reimagined home on a quiet country road where modern design meets relaxed Catskills living. Finished in striking black and situated on a half-acre of lawn, lush gardens and mature landscaping, this bright, fully renovated home blends thoughtful contemporary design with warmth and comfort throughout. Inside, vaulted ceilings and oversized windows fill the home with natural light, highlighting the open-concept kitchen, dining, and living spaces anchored by terrazzo tile, sleek cabinetry, new appliances, and a large island perfect for gathering. The layout is both functional and inviting, with two comfortable first-floor bedrooms conveniently located near a stylish full bathroom complete with a tub and modern finishes. Upstairs, a spacious and airy second-level living room feels perched among the trees, creating the ultimate lounge or media space, while an office nook offers a view to the floor below. The private third bedroom is a peaceful retreat away from the main living areas convenient to a second oversized full bathroom on the main level, giving guests and owners alike flexibility and privacy. Outside, the property offers a perfect balance of usable space and low maintenance, complete with a freshly paved driveway, storage shed, creek frontage, and a backyard deck with trellis and string lights made for long summer evenings. Located just minutes from downtown Jeffersonville and an easy drive to Callicoon and Livingston Manor, 37 Dewitts Flats delivers high-end style, thoughtful renovations, and genuine country charm in one special Catskills home.
Courtesy: Country House Realty Inc
845-397-2590
Let country roads take you home to this charming retreat, set on a beautifully private parcel. Tucked deep into the rolling hills of Jeffersonville, this well-maintained and recently updated, custom-built 2004 home delivers a rare combination of total privacy, timeless craftsmanship, and stylish modern updates—all just minutes from town. Set far back from the road amid native landscaping, private woods, and a spring-fed pond, the home immediately welcomes you with warm cedar siding and an unmistakable sense of calm. Inside, soaring vaulted ceilings and a stunning three-story chimney—built from stone harvested directly on the property—create a dramatic focal point, while fresh paint, updated lighting, and newly installed hardwood floors bring a refined, contemporary feel throughout. The beautifully renovated kitchen features a center island, custom sage-green cabinetry, quartz countertops, stone floors, and an effortless flow into the dining and living spaces before opening onto a spacious deck overlooking the water. It’s the perfect setting for entertaining, outdoor dining, or quiet mornings with coffee and birdsong. Currently configured as a two-bedroom home with easy potential for a third, the layout includes a primary suite and a spacious, ~500-square-foot walk-out lower level with French doors and a cozy Vermont Castings wood stove. There is also a heated, insulated two-car garage with polished concrete floors and cedar accents that feels more like a designer workshop or studio than a garage. Combining turnkey comfort with room to create your own Catskills sanctuary, this exceptional property offers peaceful country living just eight minutes from the growing energy of “Jeff,” with the ever-popular destinations of nearby Livingston Manor and Callicoon close at hand.
Courtesy: Compass Greater NY, LLC
838-877-8283
Set at the end of a quiet country drive just outside Livingston Manor, 57 Sheryl Davis Road offers the kind of privacy and connection to nature that defines the best of Catskills living. Surrounded by woods and bordered by a dramatic moss-covered bluestone rock face, this contemporary take on the many historic barns that dot the country roads in the area balances thoughtful design with warmth, ease, and quiet seclusion. The four-bedroom, two-bathroom home was designed with attention to detail for both weekend escapes or full-time living, pairing sleek modern finishes with grounded, cozy details. At the center of the home, a modern kitchen with waterfall island, sculptural light fixtures, and clean-lined cabinetry flows seamlessly into the main living space, creating an effortless setting for gathering, entertaining, or curling up on the couch for a movie night in. A wood burning stove adds warmth and atmosphere during the colder months, while a generously sized first-floor bedroom and full bath offer flexibility and comfort. Upstairs, the primary bedroom features its own fireplace — equal parts practical and whimsical — alongside two additional bedrooms and a second full bath. Outdoors, the landscape unfolds as an integral part of the property’s magical landscape. Spend evenings soaking in the hot tub beneath the stars, listening to the quiet and taking in the striking natural bluestone rock face that anchors the property. Multiple outdoor spaces (fire pit anyone?) invite dining, entertaining, and long afternoons settling into the slower rhythm of upstate life. Beyond the existing home, the acreage offers future potential. A slab foundation from a former structure still remains on the property, presenting opportunities for redevelopment, whether imagined as a guest house, studio, wellness retreat, or additional creative space. Private, design-forward, and deeply connected to its surroundings, 57 Sheryl Davis Road captures a distinctly modern Catskills lifestyle just moments from Livingston Manor’s beloved restaurants, breweries, shops, and year-round charm. A short drive from the nearby towns of Roscoe, Narrowsburg, and Jeffersonville - approximately two hours from NYC. If you’re looking for a private and modern upstate escape, you’ve found it at 57 Sheryl Davis.
Courtesy: Callicoon Real Estate LLC
845-887-4400
Love grand old homes, privacy and large airy rooms with lots of natural light? Have porch goals? Then this is the home for you. The home has been lovingly undergoing a restoration. Wood floors have been brought back to life in most of the home reflecting the care that was taken with them. The bathrooms have stayed true to the original time period with fully functioning sinks, toilets and clawfoot tub with shower. Venetian plaster glows in the upstairs bedrooms, hallway and attic. The spacious living room has been painted with a lime wash. With a woodstove keeping you cozy on cooler days. New chimney and gutters are part of the beauty. The kitchen is large enough that when entertaing guests they can hang out and keep you company while getting your chef on. Off the kitchen is a butlers pantry with a seperate entrance to the back yard. You can enter the kitchen through a mudroom with places for coats, boots and handy tools. Many of the ceilings are wainscoted. The attic is the bonus. It could easily be turned into an additional bedroom suite, art studio with lots of natural light, extensive library or a private sanctuary. Sit on the porch in the morning with a cup of tea or coffee and enjoy a crossant while reading the paper or watching the birds. Out side is a gardener's paradise with a small orchard with peach, plum, apple, pear and cherry trees. There is also a grape arbor. Daffodiles, peonies, lilacs, violets and many other flowers and herbs abound. A secret club house is tucked in the back yard. A brook meanders down the side of the property. The home sits well back from the road. A two minute drive to Jeffersonville which has a grocery store, bakeries, pharmacy, speciality stores, restaurants, ice cream stand and the library. It is an short 8 mile drive to Bethel Woods. Not far from Callicoon and the Delaware river, Livingston Manor and Roscoe for trout fishing. Less then 2 hours from the GWB and an easy drive from Route 17.
Courtesy: Compass Greater NY, LLC
838-877-8283
Set against a backdrop of sweeping pastoral and mountain views, this thoughtfully renovated rustic barn blends timeless character with modern comfort in all the right ways. With its striking silhouette, hand-hewn beams, and sliding doors that frame the landscape like a living painting, the home captures the romance of its agricultural past while offering a turnkey retreat designed for effortless upstate living, or immediate short-term rental income. Evenings are best spent soaking in the hot tub under open skies, surrounded by the quiet beauty that makes this setting so special. Inside, the open concept kitchen and living area serves as the heart of the home, where warm wood accents and original barn details create an inviting, grounded atmosphere. A cozy wood burning stove anchors the living space, offering both warmth and ambiance during cooler months, while sliding doors connect seamlessly to the outdoors, drawing in natural light and mountain views. The home offers two comfortable bedrooms and two full baths, plus an additional room currently used as a third sleeping space, ideal for hosting guests or maximizing rental potential. Upstairs, the primary suite occupies its own private wing, creating a true sanctuary. A charming window nook offers the perfect perch for morning coffee or quiet reflection, overlooking the rolling landscape beyond. Throughout, the careful preservation of rustic textures honors the home's heritage while ensuring modern livability. There's also an additional unrenovated 3600sq ft of the original barn, so you have flexibility to add more living space or have room for studio/work space as you see fit. Located in the heart of Jeffersonville, just minutes from vibrant Livingston Manor, the property offers easy access to some of the Catskills' most beloved destinations. Spend your days fly fishing on the Willowemoc, dining at local favorites like The Arnold House, Threshold, Kaatskeller, browsing charming boutiques, or exploring nearby hiking trails and scenic drives. Despite its peaceful, tucked-away feel, the home is conveniently located two hours from the George Washington Bridge, making it an ideal weekend escape or full-time retreat for city dwellers seeking fresh air and mountains.
Courtesy: Hart & Johnson Realty
347-739-4723
Streamfront Retreat 5 Bedrooms Newly Renovated Youngsville, NY Welcome to your Catskills escape! This beautifully renovated 5-bedroom home, set along a peaceful stream in Youngsville, offers the perfect blend of space, comfort, and natural beauty. Step inside to discover a brand-new kitchen that flows seamlessly into a bright, open living area, complemented by a formal dining room—ideal for entertaining. The home features a spacious layout with one large bedroom on the main level and four additional bedrooms upstairs, along with a convenient laundry room and two full bathrooms. The primary suite is a true retreat, boasting high ceilings, generous space, and a private en-suite bath. Enjoy outdoor living from both the charming front porch and the expansive rear deck overlooking your backyard oasis. A tranquil creek runs the full length of the property, creating a serene setting perfect for relaxing, strolling, or simply unwinding in nature. Additional creek frontage is also available for those seeking even more space. Ideally located near the vibrant hamlets of Jeffersonville, Livingston Manor, Roscoe, and Callicoon, you’ll enjoy easy access to dining, shopping, and outdoor recreation—while still savoring the peace and privacy of your own streamside haven. A rare opportunity to own a spacious, move-in-ready home with stream access in the heart of the Catskills.
Courtesy: Hart & Johnson Realty
347-739-4723
Escape to a true Catskills retreat where privacy, charm, and natural beauty come together on over 5 picturesque acres. Tucked away behind a private driveway, this beautifully renovated property offers a peaceful setting surrounded by beautiful stone walls and scenic wooded landscapes. The inviting home features 3 bedrooms and 1.5 baths, thoughtfully updated while maintaining its warm country character. Outside, the property offers several versatile outbuildings, including a detached 2-car garage and an additional shed perfect for a bunkhouse, studio, or charming chicken coop. Enjoy long summer days relaxing in the gazebo, exploring the manicured walking trails that wind throughout the property, or gathering around the designated fire pit under the stars. Whether you’re looking for a full-time residence, weekend getaway, a lucrative air bnb, or country escape, this property captures the essence of Catskills living. Conveniently located near some of the area’s most beloved hamlets, including Livingston Manor, Roscoe, Jeffersonville, and Callicoon, offering easy access to dining, shopping, fly fishing, hiking, and year-round recreation.
Courtesy: HomeCoin.com
888-400-2513
Fully Remodeled Ranch in the Heart of Youngsville. Welcome to this beautifully updated 3-bedroom, 2-bath ranch-style home situated on 1.56 peaceful acres in the heart of Youngsville! This move-in ready property offers the perfect blend of comfort, space, and outdoor living. Inside, you’ll find a fully remodeled interior with a bright and inviting layout, including a spacious sunroom, gorgeous stone fireplace and large breezeway perfect for relaxing or entertaining. The home also features a garage and plenty of room for storage. Large Attic for storage. Step outside to your own private backyard oasis featuring a huge pool, spa, gorgeous patio, and expansive yard — ideal for summer gatherings, and fun, or simply enjoying the peaceful surroundings. If you’ve been searching for country charm with modern updates and incredible outdoor space, this is the one you’ve been waiting for!
Courtesy: Compass Greater NY, LLC
838-877-8283
Set high above the surrounding countryside, where eagles glide and the air shifts a little quieter, this extraordinary hilltop retreat offers architectural distinction, total privacy, and a true sense of escape - approximately two hours from the bustle of New York City. A winding, forested drive reveals the home gradually, heightening the arrival. Custom-built with Californian and Japanese influences, the residence is thoughtfully plotted to capture sweeping views and natural light through a dramatic curved wall of floor-to-ceiling windows. A soaring two-story stone chimney anchors the space, with steel beams fanning outward to frame the landscape like living art. Inside, the scale is grand yet warm. Radiant-heated bluestone floors, wood and stone sourced from the property, and refined natural finishes create a grounded, elevated feel. The open living and dining area flows into a true chef’s kitchen with marble countertops, Wolf range, Sub-Zero refrigeration, Gaggenau steam oven, walk-in pantry, and a pizza oven built into the bluestone fireplace. Just beyond, a screened-in porch invites slow mornings and long evenings wrapped in nature. The main level includes a serene primary suite, while upstairs offers two generous additional bedroom suites with stunning views, one with a traditional Hinoki soaking tub offering a truly unique self-care moment. A suspended balcony overlooks the living space, perfectly positioned to take in the ever-changing panoramic view of the mountains and the countryside below. Thoughtful details include towel warmers in each bathroom, a dedicated tea kettle burner and two sinks in the kitchen, and a dumbwaiter from the garage to the pantry. A full, unfinished lower level offers flexibility for an artist studio, gym, or workshop, along with two-car garage access. While the property itself is the epitome of privacy, Callicoon Center is central to so many great destination towns, with Callicoon, Livingston Manor, Roscoe, North Branch, and Jeffersonville only 10-20 mins away. A myriad of fine and fun dining can be found in the area starting right down the road at Conover Club at Callicoon Hills, and there are dozens of amazing local businesses to support! This area is famous for its sweeping rural beauty and fly fishing, in addition to tons of hiking, swimming, kayak/canoeing, and more. Two hours to the GWB in NYC.
Courtesy: Corcoran Country Living
845-338-5832
Charming Tudor-style home on a spacious lot in the heart of Sullivan County. The main level features a living room, dining room, kitchen with outdoor porch, and a large flexible room ideal as a third bedroom or home office, while two bedrooms are located upstairs. Set on a large, usable yard with room to expand or create outdoor living. Strong value-add potential in a growing market, minutes to Jeffersonville, Livingston Manor, and Callicoon.
Courtesy: Keller Williams Upstate NY Properties
607-510-4444
This charming 1940s farmhouse is a special find. It’s mid-gut renovation so all the difficult and expensive work has been completed, waiting for you to bring the finishing touches. The design and floorplan layout has been thoughtfully re-imagined. A professional interior designer has transformed it from a 1-bed/1-bath (1,146 sq ft) to a 3-bed/2.5-bath (1,542 sq ft), enhancing space, flow, and natural light. Designed to blend indoor and outdoor living, the home boasts high ceilings, energy-efficient Pella and Marvin windows, and sliding doors that open to an eventual deck overlooking a stunning meadow and mountain view. The main floor features a spacious living room/kitchen, a new mudroom, and a light-filled primary bedroom with an en suite bath. A circular pea gravel driveway, 200-amp electric service, all-new plumbing, a washer/dryer hookup, and a coffee bar/wet bar sink have been installed. The upstairs offers two well-sized bedrooms and a full bath, with newly framed ceilings for added height. Situated on 4 acres, the property includes a 2-story barn across the road, with potential for a garage, workshop, cabin or studio conversion. Located in North Branch, a peaceful hamlet near Livingston Manor, Callicoon, and Jeffersonville. Being sold as-is, the asking price takes into account the completed renovations and the remaining work. Some building materials and fixtures are included, with additional remodel items available for purchase. Contents that are included in the sale: Drywall panels, Batting insulation, Marvin sliding window (for upstairs bedroom), Pella Window (for second upstairs bedroom), Vintage wooden shutters (for street-side exterior), Fiberglass clawfoot tub and plumbing fixture, Upstairs vanity, bar sink and faucet, 2 matching chandeliers for living room, Vintage brass chandelier for mudroom, Marvin French door (for living room), Decking wood. Other items can be negotiated.
Courtesy: Country House Realty Inc
845-397-2590
Welcome to Kenoza Blue, a turnkey home with classic lines, ample space, and 160 feet of lake frontage on one of Sullivan County’s finest private lakes. Gut renovated in 2023, this home is move-in ready day one, and with five bedrooms, it’s also ready for hosting the whole gang on day one too. Throughout the home, you’ll find charm and character and that starts on the outside with a rocking chair porch greeting visitors. Step in to the generous foyer and immediately you’re struck by the classic walnut staircase, the stained glass window detailing, and the ease with which the house flows. The downstairs has four distinct rooms - each one separate but never disconnected. It’s an easy space to imagine hosting a large group. A large living room is ready for movie nights, a traditional dining room begs to host holidays and festive gatherings, and a new, streamlined kitchen with open shelving keeps the space feeling light and airy. You’ll also notice the original wood floors flowing throughout, balancing the newer finishes. A gut renovated full bathroom with walk-in shower rounds out the first floor. Like many classic lakehouses, the upstairs is reserved mostly for sleeping - and the downstairs, for the fun stuff. Up the stairs, and you’ll find all five bedrooms - all capable of supporting a queen or king bed, and all with closets. A stacked washer/dryer at the end of the hallway means easy laundry after a busy weekend with no toting up and down. The second full bathroom with shower and tub combo is right in the middle of the second floor, easily shared among the bedrooms. Outside, where you’re likely to spend much of your time, you’ll find 1.1 gently sloping acres with a mix of lawn, meadow, and woods, all leading down to your private dock and 160 feet of lakefront. A brand new deck leads off the back of the house, and right down to the yard for easy in and out access to the lake. Kenoza Lake is a non-motorboat, 90+ acre private lake known for its quiet, clean, swimmable waters and good fishing. Electric motors for trawling are permitted. An important detail - most homes that have lake access to Kenoza Lake are part of the Kenoza Lake Estates HOA which restricts short term rentals (airbnb etc.) among other things. Kenoza Blue is NOT part of the HOA, and short-term rental would be permitted in accordance with the town of Delaware. Kenoza Lake is centrally located in western Sullivan County with easy access to many of the county’s premier towns. Jeffersonville is only 5 minutes away, Callicoon is 15 minutes, and Narrowsburg - a little under 20. Just a five minute walk up the road is Kenoza Hall - a Foster Supply hotel with year-round restaurant and bar. Kenoza Blue is a compelling option for anyone looking for a sizable lakehouse with rentability, a great location, and a classic look and feel.
Courtesy: Century 21 Geba Realty
845-856-6629
Escape to the Catskills without sacrificing comfort, convenience, or modern design. 2.5 hours from the GW. Set on three private acres in one of Sullivan County's most sought-after locations, this newly built Cape Chalet offers the space, privacy, and flexibility today's buyers are searching for. Just minutes from Livingston Manor, Callicoon, and Roscoe, this property places you close to celebrated restaurants, breweries, fly fishing, hiking trails, farmers markets, and year-round outdoor recreation while still enjoying a peaceful mountain setting. Designed for both everyday living and weekend entertaining, the home offers over 2,300 square feet of finished living space plus an additional 1,300 square feet in the partially finished lower level. Dramatic trapezoid windows flood the home with natural light and frame the surrounding woodland views, creating the feeling of living among the trees. The open-concept floor plan brings everyone together, with a spacious kitchen flowing seamlessly into the main living area. Multiple indoor and outdoor gathering spaces, including a patio, fire pit area, indoor balcony, and private outdoor seating areas, make hosting effortless in every season. Three spacious bedrooms and three full baths provide comfort and privacy. Two bedrooms feature en-suite baths, making the layout ideal for guests, extended stays, or flexible living arrangements. The second-floor primary suite serves as a private retreat complete with a loft-style library and balcony overlooking the great room below. For those seeking a Catskills getaway with income potential, the home's layout, location, and multiple private sleeping suites create strong short-term rental appeal. High-speed connectivity, flexible bonus rooms for a home office or creative studio, and year-round accessibility also make this an excellent full-time residence. Additional features include propane heat, a backup generator, a universal EV charger, usable acreage, and the peace of mind that comes with modern construction. Whether you're searching for a move-in-ready Catskills retreat, a full-time home surrounded by nature, or a property that offers both personal enjoyment and rental potential, this exceptional new construction delivers the best of Sullivan County living.
Courtesy: Matthew J Freda Real Estate
845-887-5640
Three story Victorian 5-BR home located on the end of a quiet cul-de-sac overlooking the bustling village of Callicoon, the Callicoon Creek and the Delaware River. In-town living doesn't get better than this. Enter on a large wrap-around porch and into a well-built home. You are greeted by an expanse of gleaming wood floors and a large living room and dining room. The updated eat- in kitchen has oak cabinets and granite counter tops. French doors lead into a quiet family room. Upstairs on the 2nd level find 3 bedrooms and a full bath. The 3rd level has 2 bedrooms with an additional bonus room. In the basement you will find the oil furnace, 200-amp electric panel and plenty of room for storage or workshop. This grand home has many original features such as beautiful wood floors, wood trim, 2- story staircase, stained glass windows, and more. Updated features include replacement windows, vinyl siding and a mini-split unit on first floor for heat and AC and fully insulated. Need storage and parking? Outside find a large detached 1-car garage plus a fenced in garden. In-town living is easy, because Callicoon is a fun town with activities including: The Farmers Market, movie theater, a community center offering tennis, swimming pool and pickleball, the Delaware River, great restaurants and shops.
Courtesy: Matthew J Freda Real Estate
845-887-5640
The living is easy in this Delaware riverfront cottage. River Road is a special feature in Callicoon, as it is a low-traffic, dead-end road that runs 4 miles upriver. This property is situated near the end, where there is almost no traffic. It's a great spot to walk, ride bikes, and take in the beauty of the Delaware River. The eagles soar and the swimming and fishing are great. The cottage is efficiently built, with an open floor plan, kitchen, tile floors, wood stove, electric baseboard heat, 200-amp electric, insulated windows, full bath, sleeping area and extra sleep space in loft. It's easy to enjoy and easy to maintain. The land is level with a large fenced garden, orchard with diverse fruit trees and chestnuts, stone walls and 150 feet of your own riverfront. Leave the kayaks and canoes on the shore, just grab 'em and hit the water! The shed is perfect for gardeners to store all the pots, tools and mowers. Just 4 miles from Callicoon with its restaurants, shops, farmer's market, and more. Two hours NYC.
Courtesy: Country House Realty Inc
845-397-2590
Character may be an overused word in real estate, but it’s a rare home that exhibits as much warm gravitas as Old Hankins Manor. From the moment you pull up the drive, past the private half acre pond and up to the wraparound rocking chair porch, you’re struck by a sense of timelessness and comfortable elegance. Tucked back from the quiet country road, this home has stood sentinel over the surrounding farmland for over 125 years. The formal front entrance welcomes you into a generous foyer with ornate staircase. Nestled behind this is a cozy media room, tucked away from the rest of the living space. The sitting room and den with stone double-sided fireplace welcome you into the primary entertaining space, then through to the spacious formal dining room, with the other face of the fireplace and wooden built-in shelving. The kitchen is highly functional while retaining an old country charm - think red checkered linens, aged porcelain sink, weathered wood and fresh baked cherry pies. Off this space is a convenient pantry with floor to ceiling cabinets and an additional sink. A full bathroom off the kitchen also houses a washer/dryer unit. At the second floor landing, you’ll find a lovely, sunny sitting room before heading down the hallway housing five bedrooms, each with a distinct character, allowing you to direct your guests to the ‘lilac room’ or the ‘red room’. There are two full bathrooms on this floor, one with a clawfoot tub, positioned under a dramatic stained glass window, and another with a tiled shower with charming old-style fixtures. The third floor houses a massive primary suite. The bedroom features a circus-tent-like peaked ceiling, working brick fireplace and large sitting area. A full en suite bath offers another clawfoot soaking tub and walk in tiled shower with skylight. A charming dressing room and large glass-encased office finish off this floor. Outside, a pathway off the back of the house leads past a stone patio with fire pit to the heated pool. The simple layout of the this area allows you to appreciate the natural privacy of open fields and mature trees. To the other side of the property, the clear freshwater pond offers opportunities for swimming, paddling, and peaceful contemplation. The front lawn is large and lightly sloping, making it inviting for lawn games for your family and friends. Almost unbelievably, this idyllic escape is also just a ten minute walk to all the charms and conveniences of Main Street, Callicoon.
Courtesy: Land and Water Realty LLC
845-807-2630
There is new construction to make a quick buck, and there is new construction that is thoughtfully designed and pridefully constructed to create a home that can last a lifetime. This modern home with an elegant, rustic twist is certainly the latter and just what you are looking for if you want a home combining simplicity with soul. That blend is difficult to get right but here that marriage of modern simplicity with raw, authentic soul is absolutely perfected. You have a total of 3 beds and 2 full baths with a master suite that has a private bathroom and an extra-large walk-in closet. The open floor plan is ideal for entertaining friends without feeling congested. There are large Anderson glass windows and sliding doors with southwestern exposure leading to the full-length deck. Walking out on the deck to the setting sun with an evening beverage might be just what the doctor ordered to escape the fast-paced, obscure digital world, if even for just a moment. A full walk-out basement can easily be finished to create additional living space, should it be necessary. This is not some Home Cheapo construction; every finish and every detail was hand-picked from top brands to perfectly fit this curated masterpiece. You really won't want to miss an opportunity to make this place your own. Set on 5+ acres in an oak forest, you will have a feeling of community but with enough elbow room to feel privately secluded. Minutes to Callicoon, and less than a mile from the hospital, you have all the creature comforts you can ask for in a community where strangers still wave at each other, and people still smile as you walk past them on the street. This home is truly fitting for its location. Highly regarded as one of the best small towns in America, Callicoon, NY offers a historic main street with a thriving, year-round farmers market, vintage shops, and cafes. Whether it is food and drinks at the Creekhouse Grill, Seminary Hill Cidery, or the Black Walnut, a night at the movie theater, or a day at the famous tractor parade, you will feel it in your bones that this place is what life is really all about. Do not wait, schedule your showing today.
Courtesy: Country House Realty Inc
845-397-2590
Set among the bucolic rolling hills of Callicoon on a half acre, Farmview Chalet is a wonderful opportunity for a buyer looking for a project with some of the dirty work already done. Gutted to the studs and ready for build out, roll up your sleeves and make this magical little chalet come to life. Entering the house, you’re greeted by a living room with a brick fireplace as a charming focal point. It’s easy to see nights spent fireside on your vision board, and to let the house grow from there. A staircase with decorative spindles divides the lower level logically and also provides some architectural intrigue. On the far side of the staircase, a light and bright rear room open up. This could be a dining space or kitchen - both would be great choices to soak up the southern light that pours in year-round. Adjacent, you’ll find the full bathroom ready for its new life. Upstairs, there are two bedrooms on the front and back of the home, including the charming juliet balcony overlooking the neighboring farm fields. Need a little extra room? Perhaps a dormer and a primary bathroom could be just the right idea. Whatever you choose, with the space totally opened up, you’ll be able to see all the available options easily. Located only 5 minutes from Callicoon, and 10 from Jeffersonville - Farmview Chalet is in a sweet spot in western Sullivan County. It’s rare to find a project like this, in a location like this, with a price like this. Don’t dilly dally - come make it your very own HGTV moment. AI-assisted imagery included in the listing to get the ideas flowing.
Courtesy: Keller Williams Upstate NY Pro
607-431-2540
Perched above the heart of Callicoon, this 1908 landmark stands as one of Sullivan County's most captivating historic structures—a former schoolhouse whose legacy spans education, craftsmanship, and art. Over the decades, its grand proportions have sheltered classrooms, a dress factory, and a piano workshop—each chapter leaving its mark in the woodwork, wainscoting, and soaring ceilings that remain today. Now reimagined by artists, the building bridges eras with a rare blend of authenticity and modern livability. A bright three-bedroom, two-bath residence offers comfort and warmth with custom cabinetry, solid wood floors, and rich natural light. Beyond, the structure unfolds into vast and inspiring spaces: a 60-by-34-foot gymnasium with a 20-foot ceiling and stage; a luminous upper-floor dance studio spanning nearly sixty feet; art studios inspired by gigantic windows bringing in nature and sunlight, open workrooms, and a full stacked stone-foundation basement with walk-in access. At roughly 13,000 square feet on over an acre, the property invites both vision and versatility. Zoned for mixed use, it can evolve into a gallery and performance venue, a live-work compound, a wellness retreat, or a community hub. Every beam and window suggests possibility—every echo in the old gym reminds you that this building was made for voices, for movement, for gathering. Surrounded by ornamental trees and perennial gardens, and just a short stroll from Callicoon's beloved cafes, the farmers' market, and the Delaware River, 48 Upper Main offers both privacy and presence. It is that rare piece of architecture that feels both anchored in history and untethered in potential. Updated infrastructure includes a new metal roof and a new boiler (with a copper manifold that will inspire envy). A place where authenticity reigns, light abounds, and inspiration seems to gather naturally within the walls. 48 Upper Main Street isn't just a building—it's a living story waiting for its next author. Offering includes two tax parcels .89 acres and .25
Courtesy: Keller Williams Upstate NYProp
585-877-8283
Perched above the heart of Callicoon, this 1908 landmark stands as one of Sullivan County’s most captivating historic structures—a former schoolhouse whose legacy spans education, craftsmanship, and art. Over the decades, its grand proportions have sheltered classrooms, a dress factory, and a piano workshop—each chapter leaving its mark in the woodwork, wainscoting, and soaring ceilings that remain today. Now reimagined by artists, the building bridges eras with a rare blend of authenticity and modern livability. A bright three-bedroom, two-bath residence offers comfort and warmth with custom cabinetry, solid wood floors, and rich natural light. Beyond, the structure unfolds into vast and inspiring spaces: a 60-by-34-foot gymnasium with a 20-foot ceiling and stage; a luminous upper-floor dance studio spanning nearly sixty feet; art studios inspired by gigantic windows bringing in nature and sunlight, open workrooms, and a full stacked stone-foundation basement with walk-in access. At roughly 13,000 square feet on over an acre, the property invites both vision and versatility. Zoned for mixed use, it can evolve into a gallery and performance venue, a live-work compound, a wellness retreat, or a community hub. Every beam and window suggests possibility—every echo in the old gym reminds you that this building was made for voices, for movement, for gathering. Surrounded by ornamental trees and perennial gardens, and just a short stroll from Callicoon’s beloved cafes, the farmers’ market, and the Delaware River, 48 Upper Main offers both privacy and presence. It is that rare piece of architecture that feels both anchored in history and untethered in potential. Updated infrastructure includes a new metal roof and a new boiler (with a copper manifold that will inspire envy). A place where authenticity reigns, light abounds, and inspiration seems to gather naturally within the walls. 48 Upper Main Street isn’t just a building—it’s a living story waiting for its next author. Offering includes two tax parcels .89 acres and .25
Callicoon is located in New York. Callicoon, New York has a population of 2,996. Callicoon is less family-centric than the surrounding county with 21.08% of the households containing married families with children. The county average for households married with children is 27.82%.
The median household income in Callicoon, New York is $64,813. The median household income for the surrounding county is $63,393 compared to the national median of $69,021. The median age of people living in Callicoon is 49.8 years.
The average high temperature in July is 79.8 degrees, with an average low temperature in January of 12.5 degrees. The average rainfall is approximately 49.3 inches per year, with 66.5 inches of snow per year.
