24

Delaware, NY Houses for Sale

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  • /18

    $289,000

    • 3 Beds
    • 1.5 Baths
    • 1,492 Sq Ft

    5030 State Route 52, Jeffersonville, NY 12748

    A true Jeffersonville original, thoughtfully prepared for its next chapter. Set along the banks of the gentle brook, this 1930 Craftsman has been carefully gutted, offering a rare opportunity to restore a home with authentic character while bringing your own vision to life.Originally built by the owners of nearby Kohler Lumber, the home still showcases many of its original Craftsman details,

    Agent Photo

    Edward Rabon

    Compass Greater NY, LLC

    5030 State Route 52, Jeffersonville, NY 12748
  • /44

    $596,500

    $53K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,048 Sq Ft

    519 County Route 164, Callicoon, NY 12723

    A rare opportunity in the heart of Sullivan County's Catskills — this stunning 5-acre property offers a spectacular view, unmatched privacy, and direct access to a championship 18-hole golf course. Whether you’re dreaming of a peaceful country home, a high-earning VRBO retreat, or a charming bed-and-breakfast, this property delivers location, scenery, and potential. The home exudes warmth and

    Agent Photo

    Rosemarie DeCristofaro

    Callicoon Real Estate LLC

    519 County Route 164, Callicoon, NY 12723
  • /50

    $1,048,000

    • 4 Beds
    • 3.5 Baths
    • 3,750 Sq Ft

    63 Sky View Dr, Callicoon, NY 12723

    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

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    Barry Becker

    KW Hudson Valley United

    63 Sky View Dr, Callicoon, NY 12723
  • /30

    $439,000

    $26K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,885 Sq Ft

    58 Polster Rd, Callicoon, NY 12723

    Historic Beechwoods Farmhouse on 14+ Acres, Major Improvements Already Made & Ready for Your VisionA 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

    Agent Photo

    Elizabeth Bernitt

    Century 21 Geba Realty

    58 Polster Rd, Callicoon, NY 12723
  • /29

    $1,295,000

    $100K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,623 Sq Ft

    5948 New York 52, Kenoza Lake, NY 12750

    Once the home and studio space of an internationally renowned pop artist and print maker, this 92 acre property with three ponds, a vineyard, and a vast expanse of rolling hills begs to be explored. The original farmhouse was built in 1880 and has been lovingly maintained with plenty of original charm preserved. Two barns, three tiny houses and a green house complete this offering - each bringing

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    Edward Rabon

    Compass Greater NY, LLC

    5948 New York 52, Kenoza Lake, NY 12750
  • /32

    $349,000

    • 3 Beds
    • 2.5 Baths
    • 1,438 Sq Ft

    7 Villa Vista Dr Unit 702, Callicoon, NY 12723

    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

    Agent Photo

    Rosemarie DeCristofaro

    Callicoon Real Estate LLC

    7 Villa Vista Dr Unit 702, Callicoon, NY 12723
  • /38

    $475,000

    • 2 Beds
    • 1 Bath
    • 1,177 Sq Ft

    2547 River Rd, Damascus, PA 18415

    Exceptional 178 ft. of riverfront with charming chalet within easy walking distance to Callicoon on the Delaware, its eateries, shops, movie theatre, etc.! There is a shed/storage building where you could store all river related gear. fishing poles, etc. near the river access. The home has comfortable living space of entrance foyer, living room with wood stove, dining area, kitchen and bathroom.

    Agent Photo

    Rosemarie DeCristofaro

    Callicoon Real Estate, LLC

    2547 River Rd, Damascus, PA 18415
  • /30

    $989,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,544 Sq Ft

    32 Long Farm Way, Callicoon, NY 12723

    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

    Carol Malek Malek Properties, Inc.

    32 Long Farm Way, Callicoon, NY 12723
  • /32

    $389,000

    • 3 Beds
    • 1.5 Baths
    • 1,856 Sq Ft

    5026 State Route 52, Jeffersonville, NY 12748

    Kohler Craftsman is a charming 105-year-old storybook home located in the vibrant Village of Jeffersonville. Rich in character and history, this well-maintained residence offers 3 bedrooms, 1 full bathroom, and 1 half bathroom on a beautifully landscaped and private 0.38-acre lot. The fenced yard features a heated above-ground pool, grassy lawn, and a spacious two-car garage. Originally built by

    William Baldwin Country House Realty Inc

    5026 State Route 52, Jeffersonville, NY 12748
  • /50

    $379,000

    $70K PRICE DROP
    • 5 Beds
    • 1.5 Baths
    • 2,536 Sq Ft

    11 Highview Ave, Callicoon, NY 12723

    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

    Susan Busing Matthew J Freda Real Estate

    11 Highview Ave, Callicoon, NY 12723
  • /50

    $749,999

    • 7 Beds
    • 4 Baths
    • 4,900 Sq Ft

    28 Upper Main St, Callicoon, NY 12723

    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

    Gregory Berkowitz BERKSHIRE HATHAWAY

    28 Upper Main St, Callicoon, NY 12723
  • /45

    $349,000

    $50K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 400 Sq Ft

    860 River Rd, Callicoon, NY 12723

    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

    Joe Freda Matthew J Freda Real Estate

    860 River Rd, Callicoon, NY 12723
  • /48

    $759,000

    $71K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,536 Sq Ft

    48 Upper Main St, Callicoon, NY 12723

    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

    Dara Barr Keller Williams Upstate NY Pro

    48 Upper Main St, Callicoon, NY 12723
  • /26

    $769,000

    New Construction $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,664 Sq Ft

    204 Country Rd, Callicoon, NY 12723

    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

    Lynne Freda Matthew J Freda Real Estate

    204 Country Rd, Callicoon, NY 12723
  • /46

    $1,299,999

    • 4 Beds
    • 3.5 Baths
    • 3,310 Sq Ft

    140 Kenoza Trail, Callicoon, NY 12723

    A private gated community surrounded by nature. This exceptional retreat offers the perfect blend of privacy, luxury, and tranquility. Enter to a spacious great room featuring a stunning stone fireplace, creating a warm and inviting gathering space. The chef’s kitchen is thoughtfully designed for both everyday living and entertaining and flows seamlessly into a beautiful sunroom overlooking the

    Jill Halpern-Steingart Rieber Realty Inc

    140 Kenoza Trail, Callicoon, NY 12723
  • /40

    $389,000

    $10K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,014 Sq Ft

    4929 State Route 52, Delaware, NY 12748

    Waterfront on Main-4929 Route 52 is a beautifully maintained 1930s-era Sears kit home, showcasing timeless character and an array of charming original details throughout. Recent renovations have thoughtfully restored and highlighted the home's original woodwork, bringing its historic charm back to life. The property features more than 90 feet of frontage on the Callicoon Creek and enjoys

    Alan Wieder Catskills Home Services

    4929 State Route 52, Delaware, NY 12748
  • /49

    $1,900,000

    • 6 Beds
    • 4 Baths
    • 3,426 Sq Ft

    56 Winkelstern Rd, Kenoza Lake, NY 12750

    Meadowbrook soars on so many levels, not least the stunning 85+ acres: rolling hills, clearings, water features, an orchard, and mature landscaping that elevate the everyday to something truly sublime, at this private Catskills estate. Pulling onto the property, the East Branch of Callicoon Creek is visible beyond a cleared bank with a line of Adirondack chairs. The paved drive passes old maples

    Jennifer Grimes Country House Realty Inc

    56 Winkelstern Rd, Kenoza Lake, NY 12750
  • /45

    $460,000

    • 3 Beds
    • 2 Baths
    • 1,748 Sq Ft

    5089 State Route 52, Jeffersonville, NY 12748

    Discover an exceptional opportunity in the charming hamlet of Jeffersonville, New York, where location, lifestyle, and investment potential come together on one remarkable property. This beautifully maintained 3-bedroom, 2-full-bath split-level home offers comfortable living with room to grow, all nestled along the banks of the famed Callicoon Creek. Step inside to find a warm and inviting

    Dawn Payne PAYNE TEAM LLC

    5089 State Route 52, Jeffersonville, NY 12748
  • /18

    $355,000

    $15K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    12 Mesmer Hill Rd, Callicoon, NY 12723

    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

    Thelonious Johnson Hart & Johnson Realty

    12 Mesmer Hill Rd, Callicoon, NY 12723
  • /33

    $599,000

    $51K PRICE DROP
    • 5 Beds
    • 2 Baths
    • 1,800 Sq Ft

    5697 New York 52, Callicoon, NY 12723

    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

    Jared Gluckstern Country House Realty Inc

    5697 New York 52, Callicoon, NY 12723
  • /41

    $670,000

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,628 Sq Ft

    340 Hospital Rd, Callicoon, NY 12723

    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

    Thelonious Johnson Hart & Johnson Realty

    340 Hospital Rd, Callicoon, NY 12723
  • /41

    $1,350,000

    • 6 Beds
    • 4 Baths
    • 4,080 Sq Ft

    91 Old Hankins Rd, Callicoon, NY 12723

    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

    Megan Kinealy Country House Realty, Inc.

    91 Old Hankins Rd, Callicoon, NY 12723
  • /33

    $499,000

    $150K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 4,032 Sq Ft

    62 Delaware Ave, Damascus, PA 18415

    Come fall in love with this Delaware Riverfront beauty! This spacious home has one of the most commanding views of the Delaware River, and it's just a minute from Callicoon. A former boarding house, then used as a single-family residence, the zoning permits Commercial use, like a hotel, B&B or short-term rentals. There's a place for everyone, with 8+ bedrooms in the main house, and 2 cabins...

    Lynne Freda Matthew J. Freda Real Estate, Inc.

    62 Delaware Ave, Damascus, PA 18415
  • /59

    $995,000

    $205K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,919 Sq Ft

    33 Syloro Ln, Damascus, PA 18415

    Delaware riverfront property doesn't come along too often, and this is a rare find, especially on 3.71 private acres! This gorgeous, well-maintained 4BR, 3.5 bath turnkey Beaver Mountain log home has a place for everyone! The main portion of the house features 3 bedrooms and 2.5 baths. The primary suite is on the main floor, with 2 other BRs upstairs and a full bath. There's a separate apartment

    Lynne Freda Matthew J. Freda Real Estate, Inc.

    33 Syloro Ln, Damascus, PA 18415

Why Live in Delaware

Delaware is a town in southwestern New York, on the Pennsylvania border and along the Delaware River. Not to be confused with nearby Delaware County, the town is made up of several hamlets, including the thriving riverside community of Callicoon. State Routes 97 and 52 connect to nearby towns like Cochecton, Hancock and Monticello. Ranch-style homes and cabins sell from the mid-$100,000s to the mid-$300,000s, but luxury chalets and contemporary homes can fetch over a million. Some houses date to the 1800s and might need updates. Winter weather can impact daily commutes, but flooding isn't typically an issue. In Callicoon, you'll find shops, groceries at Peck's Market and restaurants like Black Walnut and the Callicoon Brewing Company. Jobs and major retailers can be found half an hour away in Monticello. Delaware has jobs in health care, tourism, recreation, agriculture and retail, and some people work from home. Neighbors gather for seasonal festivals in Callicoon, including Dickens on the Delaware and PorchFest. Stone Arch Bridge Park offers year-round outdoor recreation. Kids can attend schools in the Sullivan West Central School District, both within a short drive.

Single Family Home Price Trends

Median Home Price
$389,000
Median 3-Bedroom Home Price
$389,000
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