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Callicoon, NY Homes for Sale with Garage

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  • /51

    $450,000

    • 3 Beds
    • 3 Baths
    • 1,700 Sq Ft

    136 Kautz Rd, Callicoon, NY 12723

    Tucked away on a quiet country road and surrounded by beauty, 136 Kautz Road offers a rare opportunity to own a lovingly maintained ranch home in one of Sullivan County's most desirable locations. Built in 1978, this 3-bedroom, 2.5 bath home has timeless appeal, with hardwood floors throughout and a stunning brick fireplace that anchors the spacious living area. The home sits gracefully back from

    Agent Photo

    Elizabeth Bernitt

    Century 21 Geba Realty

    (845) 807-6947

    136 Kautz Rd, Callicoon, NY 12723
  • /44

    $335,000

    • 3 Beds
    • 2.5 Baths
    • 1,960 Sq Ft

    221 Gabel Rd, Callicoon, NY 12723

    Escape to tranquility in this beautiful 3-bedroom, 2.5-bathroom home perched atop five picturesque acres with breathtaking long-range views of rolling fields and majestic mountains. Just minutes from Callicoon’s charming Main Street and beloved farmers’ market, this property offers the perfect blend of privacy and convenience. Step inside to find a gracious formal living room, a cozy den, and a

    Agent Photo

    Elizabeth Bernitt

    Century 21 Geba Realty

    (845) 807-6947

    221 Gabel Rd, Callicoon, NY 12723
  • /34

    $489,000

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

    10 W Simmon Rd, Callicoon, NY 12723

    A delightful country property is waiting for you in rural western Sullivan County and is priced to sell! Along a quaint township road you will find 26+ acres of land with a lovely home of 2 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 fenced

    Agent Photo

    Rosemarie DeCristofaro

    Callicoon Real Estate LLC

    (845) 470-4651

    10 W Simmon Rd, Callicoon, NY 12723
  • /38

    $2,250,000 New Construction

    • 6 Beds
    • 4 Baths
    • 5,000 Sq Ft

    56 Winkelstern Ln, Callicoon, NY 12723

    Nestled on 145 acres of unspoiled natural beauty, this extraordinary estate offers a rare blend of privacy, adventure, and modern comfort. With three other surrounding parcels thoughtfully acquired to preserve peace and prevent future development, this is more than a home, it's a destination designed for those who value space, serenity, and an elevated lifestyle.Whether you're looking for

    Agent Photo

    Sherret Chase

    Four Seasons Sotheby's Int'l R

    (845) 630-1626

    56 Winkelstern Ln, Callicoon, NY 12723
  • /32

    $384,000

    • 4 Beds
    • 2 Baths
    • 1,740 Sq Ft

    215 Kautz Rd, Callicoon, NY 12723

    Enjoy the benefits of Country living but the convenience of being just 10 minutes from historic Callicoon. You'll find unique clothing shops, Famous Farmer's Market every Sunday, eateries, Brewery & Theater. Plenty of elbow room in this 4 bedroom, 2 full bath raised ranch home on 3.64 acres. This conscientious seller has taken care of this property with many regular maintenance as well as

    Joan Hale Listing by Howard Hanna

    215 Kautz Rd, Callicoon, NY 12723
  • /45

    $529,000

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

    5 Hess Rd, Callicoon, NY 12723

    Solar-Powered Catskills Retreat with Mountain Views | Renovated 4BR Ranch on 2+ AcresExperience sustainable living in style at this fully solar-powered 4-bedroom, 2 full bath, 2 half bath ranch-style home (renovated 2022) in the heart of the Catskills. Set on a serene 2.07-acre corner lot with sweeping mountain and farmland views, this property combines modern efficiency, eco-friendly

    Barry Becker Keller Williams Hudson Valley

    5 Hess Rd, Callicoon, NY 12723
  • /38

    $375,000

    • 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 cottage—a 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

    Barry Becker Keller Williams Hudson Valley

    55 Upper Main St, Callicoon, NY 12723
  • /41

    $795,000

    • 5 Beds
    • 3.5 Baths
    • 2,412 Sq Ft

    2585 River Rd, Damascus, PA 18415

    Meet Fred and Gloria! Exquisite 1895 Delaware Riverfront Estate 'Gloria' with Guest House 'Fred' and Refurbished Barn–A Harmonious Blend of History and Modern Luxury. Introducing 'Gloria,' a majestic 1895 riverfront farmhouse that has been meticulously restored to combine the elegance of its historical architecture with contemporary luxury. This remarkable estate includes a 4-bedroom main house,

    Barry Becker Keller Williams Hudson Valley

    2585 River Rd, Damascus, PA 18415
  • /43

    $749,000

    • 3 Beds
    • 2 Baths
    • 2,062 Sq Ft

    178 W Simmon Rd, Callicoon, NY 12723

    Welcome to this beautiful country estate which offers deep seclusion, rolling meadows and over 1,000 feet of frontage on a large year-round trout stream. Encompassing over 50 acres, this dramatic and diverse property features a stone residence which has a stately appearance and is situated down a long secluded driveway. The home was built by a local craftsman with stone from the property. The

    Linda Mulligan Matthew J Freda Real Estate

    178 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

    Barry Becker Keller Williams Hudson Valley

    63 Sky View Dr, Callicoon, NY 12723
  • /42

    $599,000

    • 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
  • /30

    $395,000

    • 2 Beds
    • 2 Baths
    • 1,010 Sq Ft

    256 Pleasant Valley Rd, Callicoon, NY 12723

    Set well back from a picturesque country road on a wooded hillside, Pleasant Valley is a 2 bed, 2 bath, turnkey escape. Enjoy three acres of solitude, split between a level clearing of yard and mature trees for a fully ensconced feel - Pleasant Valley certainly provides the privacy you are seeking with your country home.The striking sun room is a welcome entry point to the home - full of

    Jared Gluckstern Country House Realty Inc

    256 Pleasant Valley Rd, Callicoon, NY 12723
  • /33

    $1,200,000

    • 3 Beds
    • 2.5 Baths
    • 2,821 Sq Ft

    118 Froehlich Dr, Callicoon, NY 12723

    Perched sky-high above Callicoon, this contemporary farmhouse blends an aesthetic quality of life with gorgeous views and total seclusion. Drive up the long, private road into your sun-drenched 8-acre compound and nestle into the beauty of the Upper Delaware River Valley. The surrounding woods provide privacy, while the manicured yard is level and open. A bluestone patio with gazebo surrounds a

    Joe Freda Matthew J Freda Real Estate

    118 Froehlich Dr, Callicoon, NY 12723
  • /50

    $309,000

    • 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

    Susan Busing Matthew J Freda Real Estate

    9568 State Route 97, Callicoon, NY 12723
  • /43

    $459,000

    • 3 Beds
    • 2.5 Baths
    • 1,512 Sq Ft

    174 Fulton Hill Rd, Callicoon, NY 12723

    Just Listed!! (Interior photos coming soon). Welcome home to this wonderful country home on 10 acres with huge heated 48X48 garage. The home offers living room, sunny kitchen w/ stainless steel appliances, dining area w/ sliding door to rear deck, laundry room, master bedroom suite & bath (updated January 2025), 2 additional bedrooms and full bath on main level. Lower level is mostly finished w/

    Jill Barnes Cabins & Canoes Real Estate

    174 Fulton Hill Rd, Callicoon, NY 12723
  • /33

    $429,000

    • 3 Beds
    • 2 Baths
    • 1,292 Sq Ft

    21 Mitchell Ave, Callicoon, NY 12723

    Nestled in the heart of Callicoon, NY—ranked one of the top 10 small towns in New York—this beautifully renovated 1865 farmhouse offers the perfect blend of rustic charm and modern luxury. Located in scenic Sullivan County within the breathtaking Catskill Mountains, this exceptional property is just a short stroll from downtown Callicoon's vibrant scene of restaurants, shops, a classic movie

    Steven Beeson Diane C. Butler

    21 Mitchell Ave, Callicoon, NY 12723
  • /41

    $249,000

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft

    4261 State Route 17b, Callicoon, NY 12723

    Discover serenity at this charming 3-bedroom, 2-bathroom ranch-style home nestled on a 1.1-acre lot with 240 feet of pristine Callicoon Creek frontage. Located just 3 minutes east of downtown Callicoon, NY, this property offers the perfect blend of waterfront tranquility and proximity to one of the county's most historic towns.Property Highlights:Spacious Living Areas: Enjoy a

    Dominique Jenkins Keller Williams Hudson Valley

    4261 State Route 17b, Callicoon, NY 12723
  • /42

    $1,250,000

    • 5 Beds
    • 3 Baths
    • 4,682 Sq Ft

    80 Overlook Dr, Callicoon, NY 12723

    Could you live with stunning views of the Delaware River valley and the surrounding Catskills? Watch bald eagles and hawks glide past your windows? This Beechwoods contemporary is set in a hilltop neighborhood of upscale homes. Elegant Douglas Fir post-and-beam framing creates a high cathedral ceiling and open space. All rooms have soaring views of sky, mountains and the river. South and west

    Joe Freda Matthew J Freda Real Estate

    80 Overlook Dr, Callicoon, NY 12723
  • /29

    $289,000

    • 3 Beds
    • 1 Bath
    • 1,450 Sq Ft

    93 Villa Roma Rd, Callicoon, NY 12723

    Newly renovated farmhouse in Callicoon's desirable Beechwoods area. The three-bedroom, one full bath farmhouse sits on three acres. A nice sunny yard gives an opportunity for gardening, yard games or just watching the wildlife. Situated on a quiet country road close to the bustling hamlets of both Callicoon and Jeffersonville for fun and necessities. The kitchen is bright with natural light and

    Joe Freda Matthew J Freda Real Estate

    93 Villa Roma Rd, Callicoon, NY 12723
  • /18

    $398,000

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

    12 Mesmer Hill Rd, Callicoon, NY 12723

    Peaceful Country Home on Over 5 AcresWelcome 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

    Thelonious Johnson Hart & Johnson Realty

    12 Mesmer Hill Rd, Callicoon, NY 12723
  • /35

    $1,450,000

    • 4 Beds
    • 4 Baths
    • 3,200 Sq Ft

    59 Overlook Dr, Callicoon, NY 12723

    This spectacular contemporary is filled with natural light and offers stunning mountain views from every window. This home in Callicoon's beautiful Beechwoods area is architect-designed and visually arresting from any angle--inside and out. With plentiful rooftop solar panels, lots of double- and triple-paned glass, a radiant polished concrete floor, and Nest thermostats, it is so energy

    Joe Freda Matthew J Freda Real Estate

    59 Overlook Dr, Callicoon, NY 12723
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