16

Callicoon, NY Houses for Sale

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  • /34

    $449,000

    • 2 Beds
    • 2 Baths
    • 1,600 Sq Ft

    10 W Simmon Rd, Callicoon, NY 12723

    Along a quaint township road you will find 26+ acres of land with a lovely home of 3 bedrooms, 2 full baths, spacious loft area/3rd bedroom, and a sunny and bright great room with cathedral ceiling. There is a full basement and a one car garage under the house. You will also find a shed and a lovely, stocked pond where only the ducks are missing! 10 minutes to downtown Callicoon with its

    Agent Photo

    Rosemarie DeCristofaro

    Callicoon Real Estate LLC

    (845) 373-5087

    10 W Simmon Rd, 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

    Agent Photo

    Barry Becker

    Keller Williams Hudson Valley

    (845) 443-4418

    63 Sky View Dr, Callicoon, NY 12723
  • /40

    $419,000

    • 2 Beds
    • 1 Bath
    • 1,288 Sq Ft

    55 Upper Main St, Callicoon, NY 12723

    Stylized, Convenient, In-Town 1940s Cottage with Modern Updates & Endless Possibilities! Home went through complete renovation! Welcome to this beautifully updated 1940s cottagea perfect blend of classic character and modern convenience, right in the heart of town. With 2 spacious bedrooms and a renovated full bathroom, this home offers move-in ready comfort and style. The generous kitchen boasts

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    Barry Becker

    Keller Williams Realty Hudson Valley United

    (845) 497-6779

    55 Upper Main St, Callicoon, NY 12723
  • /22

    $950,000

    • 5 Beds
    • 2 Baths
    • 2,800 Sq Ft

    797 County Route 164, Callicoon, NY 12723

    Welcome to your own Beechwoods retreat, where timeless farmhouse charm meets artful, modern living. Set on three private acres at a picturesque corner between Callicoon and Jeffersonville, this distinctive home is anything but ordinary. Sunlight pours through oversized windows, illuminating wide-plank floors, exposed beams, and thoughtfully curated spaces that feel both expansive and intimate. At

    Agent Photo

    Elizabeth Bernitt

    Century 21 Geba Realty

    (845) 807-6947

    797 County Route 164, Callicoon, NY 12723
  • /42

    $595,000

    • 4 Beds
    • 4 Baths
    • 2,631 Sq Ft

    5 Hess Rd, Callicoon, NY 12723

    Callicoon Country Living with Mountain Views Fully Renovated Ranch on 2+ Acres. Welcome to your dream retreat in the heart of the beautiful Catskills! This fully renovated 4-bedroom, 2 full bath, 2 half bath ranch-style home (2022) offers a seamless blend of modern efficiency and timeless country charm, all set on a quiet 2.07-acre corner lot with panoramic mountain and farmland views. Master

    Agent Photo

    Barry Becker

    Keller Williams Realty Hudson Valley United

    (845) 599-8021

    5 Hess Rd, Callicoon, NY 12723
  • /29

    $735,000

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft

    140 Country Rd, Callicoon, NY 12723

    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

    Travis O'Dell Land and Water Realty LLC

    140 Country Rd, Callicoon, NY 12723
  • /48

    $799,000

    • 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 NYProp

    48 Upper Main St, Callicoon, NY 12723
  • /40

    $549,000

    • 2 Beds
    • 2.5 Baths
    • 1,314 Sq Ft

    409 Kautz Rd, Callicoon, NY 12723

    This charming 2bed/2.5-bath home strikes the perfect balance between comfort and character the moment you step inside. The main living area is open and flowing, with a relaxed seating area on one side where you can kick back and take in the peaceful views over the lovely open field in the front yard. A sliding door invites you out to the large screened-in porch - the perfect spot for morning

    Erik Freeland Country House Realty Inc

    409 Kautz Rd, Callicoon, NY 12723
  • /39

    $554,000

    • 5 Beds
    • 3 Baths
    • 2,612 Sq Ft

    12 Highview Ave, Callicoon, NY 12723

    Located at the end of a quiet cul-de-sac, this stately Victorian home boasts old-world charm and overlooks the sweet river town of Callicoon. Step inside and discover a treasure trove of delightful details: charming nooks and crannies, a sunny pantry, a built-in bar, and inviting window seats. The current owners have tastefully enhanced the home with numerous improvements, including newly painted

    Heather Quaintance Country House Realty Inc

    12 Highview Ave, Callicoon, NY 12723
  • /33

    $650,000

    • 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
  • /50

    $449,000

    • 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
  • /27

    $399,000

    • 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
  • /50

    $279,000

    • 2 Beds
    • 1 Bath
    • 1,159 Sq Ft

    9568 State Route 97, Callicoon, NY 12723

    Life in the Callicoon Catskills doesn’t get any better than this fine 2 bedroom brick ranch home surrounded by a level lawn and mature trees in a park-like setting. Easily accessed by a paved driveway which leads to a heated 2 car garage and breezeway. Inside find a well-designed kitchen with a comfortable dining room. The living room has a brick fireplace and a large picture window to enjoy

    Susan Busing Matthew J Freda Real Estate

    9568 State Route 97, Callicoon, NY 12723
  • /16

    $165,000

    • 2 Beds
    • 1 Bath
    • 980 Sq Ft

    877 County Route 164, Callicoon, NY 12723

    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

    Jared Gluckstern Country House Realty Inc

    877 County Route 164, Callicoon, NY 12723
  • /18

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    12 Mesmer Hill Rd, Callicoon, NY 12723

    Peaceful Country Home on Over 5 Acres Welcome to 12 Mesmer Hill Road, a charming home set on more than 5 acres of beautiful countryside. If you're looking for a quiet retreat with plenty of space, this property is a great choice. This home features three bedrooms and two full bathrooms, along with a spacious eat-in kitchen and a separate dining area, perfect for family meals or entertaining

    Thelonious Johnson Hart & Johnson Realty

    12 Mesmer Hill 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
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