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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

$199,000

Check out this charming colonial-style farmhouse with great curb appeal. This property also features a beautiful yard with a detached one-car garage as well as a small outbuilding. The home has two covered porches for great outdoor relaxing in all seasons. This home creates a sense of nostalgia once you step inside. The main level has a mud room/laundry room. galley kitchen, separate dining room and spacious living room with a fireplace. The primary bedroom is on this level with it's own fireplace and there is a second bedroom used as an office, plus a full bath. Upstairs leads to a large loft with several sleeping areas. Don't miss out on this special property located in Long Eddy and not far from access to the Delaware River.

3 Beds ⋅ 1 Baths ⋅ 904758 MLS

Check out this charming colonial-style farmhouse with great curb appeal. This property also features a beautiful yard with a detached one-car garage as well as a small outbuilding. The home has two covered porches for great outdoor relaxing in all seasons. This home creates a sense of nostalgia once you step inside. The main level has a mud room/laundry room. galley kitchen, separate dining room and spacious living room with a fireplace. The primary bedroom is on this level with it's own fireplace and there is a second bedroom used as an office, plus a full bath. Upstairs leads to a large loft with several sleeping areas. Don't miss out on this special property located in Long Eddy and not far from access to the Delaware River.

66 Raspberry Park Road, Long Eddy

$149,000

Discover this charming countryside escape in the heart of the Catskills set on 2.5 scenic acres. This mobile home features 2 bedrooms and 1 bath, with a bright and comfortable layout. A spacious front deck overlooks the yard, perfect for morning coffee, summer gatherings, or simply soaking in the peaceful surroundings. All of this is just about two hours from NYC—making it the perfect full-time residence, weekend retreat, or investment property in the Catskills. Call and schedule your showing today!

2 Beds ⋅ 1 Baths ⋅ 899177 MLS

Discover this charming countryside escape in the heart of the Catskills set on 2.5 scenic acres. This mobile home features 2 bedrooms and 1 bath, with a bright and comfortable layout. A spacious front deck overlooks the yard, perfect for morning coffee, summer gatherings, or simply soaking in the peaceful surroundings. All of this is just about two hours from NYC—making it the perfect full-time residence, weekend retreat, or investment property in the Catskills. Call and schedule your showing today!

98 Buff Road, Cochecton

$199,000

Just bring your belongings and settle in to this completely renovated single-story home just 7 miles west of Bethel Woods. Located in the western part of a Sullivan County with its natural beauty of rolling hills, farms and Delaware River to the west. This home is completely renovated with new heating system with A/C new electric, plumbing and insulation. Both the kitchen and bathroom are new as well. Surrounding all this newness is all charm of a stone fireplace and charming wood.

2 Beds ⋅ 1 Baths ⋅ 896213 MLS

Just bring your belongings and settle in to this completely renovated single-story home just 7 miles west of Bethel Woods. Located in the western part of a Sullivan County with its natural beauty of rolling hills, farms and Delaware River to the west. This home is completely renovated with new heating system with A/C new electric, plumbing and insulation. Both the kitchen and bathroom are new as well. Surrounding all this newness is all charm of a stone fireplace and charming wood.

6115 State Route 52, Cochecton

$725,000

The Nature Enthusiast's and Sportsman’s Paradise on 88 acres with Endless Potential. Discover the perfect blend of privacy, nature, and outdoor recreation with this 88-acre retreat, ideal for hunters, homesteaders, and nature lovers. Tucked deep in the countryside, this property offers a classic old hunting camp, surrounded by a diverse landscape teeming with wildlife and potential. This 1900s house offers a solid basecamp for weekend getaways, hunting trips, or renovation into a cozy off-grid hideaway. For those looking to build their dream home, several potential building sites across the property offer beautiful views, open fields, and total seclusion. The land itself is a true outdoorsman’s dream — featuring a spring-fed pond, a year-round stream, mature fruit trees, and historic stone walls. Trails meander throughout the property, perfect for ATVs, side-by-sides, horseback riding, or hiking. Wildlife is abundant, with frequent sightings of deer, turkey, and other game species, making this a prime hunting location. A 2-bay garage, provides ample room to store gear, equipment, and recreational vehicles, and includes an unfinished upper level with potential for added storage or a future bunkroom. Whether you're looking for a private hunting haven, a weekend getaway, or the site of a future homestead, this one-of-a-kind property offers unmatched natural beauty, privacy, and opportunity.

2 Beds ⋅ 2 Baths ⋅ 872758 MLS

The Nature Enthusiast's and Sportsman’s Paradise on 88 acres with Endless Potential. Discover the perfect blend of privacy, nature, and outdoor recreation with this 88-acre retreat, ideal for hunters, homesteaders, and nature lovers. Tucked deep in the countryside, this property offers a classic old hunting camp, surrounded by a diverse landscape teeming with wildlife and potential. This 1900s house offers a solid basecamp for weekend getaways, hunting trips, or renovation into a cozy off-grid hideaway. For those looking to build their dream home, several potential building sites across the property offer beautiful views, open fields, and total seclusion. The land itself is a true outdoorsman’s dream — featuring a spring-fed pond, a year-round stream, mature fruit trees, and historic stone walls. Trails meander throughout the property, perfect for ATVs, side-by-sides, horseback riding, or hiking. Wildlife is abundant, with frequent sightings of deer, turkey, and other game species, making this a prime hunting location. A 2-bay garage, provides ample room to store gear, equipment, and recreational vehicles, and includes an unfinished upper level with potential for added storage or a future bunkroom. Whether you're looking for a private hunting haven, a weekend getaway, or the site of a future homestead, this one-of-a-kind property offers unmatched natural beauty, privacy, and opportunity.

763 County Road 114, Cochecton

$219,000

Off a quiet country road and down a long driveway sits an original Mileses homestead, reminiscent of years gone by. Dating back to circa 1850, and added to and improved over the years, this home features a rocking chair front porch where you can relax and take in the sounds of nature and enjoy the distant views. This vintage farmhouse offers good-sized rooms and some original features, with great potential for the buyer who appreciates old homes. Privately set on 6.64 acres, the land is beautifully timbered and mostly level to gently sloping. There is a spring on the property that is the water source for the home, plus remnants from a barn and old blacksmith shop can also be found. Don't miss the opportunity to visit this property if you're looking for that special place in the country where your creativity can soar.

4 Beds ⋅ 1 Baths ⋅ 864249 MLS

Off a quiet country road and down a long driveway sits an original Mileses homestead, reminiscent of years gone by. Dating back to circa 1850, and added to and improved over the years, this home features a rocking chair front porch where you can relax and take in the sounds of nature and enjoy the distant views. This vintage farmhouse offers good-sized rooms and some original features, with great potential for the buyer who appreciates old homes. Privately set on 6.64 acres, the land is beautifully timbered and mostly level to gently sloping. There is a spring on the property that is the water source for the home, plus remnants from a barn and old blacksmith shop can also be found. Don't miss the opportunity to visit this property if you're looking for that special place in the country where your creativity can soar.

12 Henderson Road, Fremont

$825,000

Majestic Grand Lady from days gone past. Started life as a 20 room boarding house, 1 bdrm guest house & dairy farm & in the 1960's the main building was turned into 5 apartments, 1-2 bdrm, 1 studio, 1 efficiency & 2- 1 bdrm. Also 9 bedrooms on the third floor but there is no heat or plumbing on that floor. Scenic views abound on the 47+ acre farm with over 30 acres of fertile pasture land, apple orchard, pond potential, 4 wells, springs. Dependable tenants some there almost 20 years. Extra 1.7 acre lot with productive well included. Taxes reflect Star & Agricultural exemptions. Recent upgrades- new 99% efficient Riello furnace, hot water heater, some electric upgrades & some exterior painting. Included some recent Northern lights picture taken by a tenant!!! Potential of $14,400 a year for owners apartment not included in income total.

7 Beds ⋅ 6 Baths ⋅ 805995 MLS

Majestic Grand Lady from days gone past. Started life as a 20 room boarding house, 1 bdrm guest house & dairy farm & in the 1960's the main building was turned into 5 apartments, 1-2 bdrm, 1 studio, 1 efficiency & 2- 1 bdrm. Also 9 bedrooms on the third floor but there is no heat or plumbing on that floor. Scenic views abound on the 47+ acre farm with over 30 acres of fertile pasture land, apple orchard, pond potential, 4 wells, springs. Dependable tenants some there almost 20 years. Extra 1.7 acre lot with productive well included. Taxes reflect Star & Agricultural exemptions. Recent upgrades- new 99% efficient Riello furnace, hot water heater, some electric upgrades & some exterior painting. Included some recent Northern lights picture taken by a tenant!!! Potential of $14,400 a year for owners apartment not included in income total.

354 E Hill Road, Jeffersonville

$478,000

Remarkable! 12 plus acres. Step into history with this extraordinary estate, featuring an authentic 19th-century stagecoach depot and a beautifully preserved period barn with a charming guest cottage or rental opportunity. The main building showcases stunning timber frame construction, original wide-plank floors, and timeless craftsmanship. The sprawling grounds include rolling meadows, fertile fields, a natural pond site, and tranquil wooded areas. The historic barn is a true architectural gem, boasting a cathedral ceiling, hand-hewn beams, original post-and-beam construction, and intact stalls—ideal for horses, events, or creative repurposing. This exceptional property presents limitless possibilities—whether as a private estate, boutique B&B, event venue, or retreat. A rare chance to own a beautifully preserved piece of American history with modern potential. Subject to final town board approval Additional Features: Additional 60 plus acres are available for 410,000 , also subject to final town approval Guest Quarters Heating: Oil (Above Ground) Parking: 2-Car Detached Garages

4 Beds ⋅ 2 Baths ⋅ H6330947 MLS

Remarkable! 12 plus acres. Step into history with this extraordinary estate, featuring an authentic 19th-century stagecoach depot and a beautifully preserved period barn with a charming guest cottage or rental opportunity. The main building showcases stunning timber frame construction, original wide-plank floors, and timeless craftsmanship. The sprawling grounds include rolling meadows, fertile fields, a natural pond site, and tranquil wooded areas. The historic barn is a true architectural gem, boasting a cathedral ceiling, hand-hewn beams, original post-and-beam construction, and intact stalls—ideal for horses, events, or creative repurposing. This exceptional property presents limitless possibilities—whether as a private estate, boutique B&B, event venue, or retreat. A rare chance to own a beautifully preserved piece of American history with modern potential. Subject to final town board approval Additional Features: Additional 60 plus acres are available for 410,000 , also subject to final town approval Guest Quarters Heating: Oil (Above Ground) Parking: 2-Car Detached Garages

301 & 305 Hust, Jeffersonville