Callicoon, NY Homes for Sale

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  /49

  $538,000

  • 2 Beds
  • 2 Baths
  • 1,496 Sq Ft

  23 River Rd, Callicoon, NY 12723

  A delightful, unpretentious farm house on over 2.3 acres of river front land in sweet Callicoon on the Delaware! It was owned for over 2 decades by a family as their escape from city life. Lots of memories were made here. Charming to the core, it had been totally remodeled when they bought and sellers have meticulously maintained or replaced systems over time. (Agent, please find separate list in

  

  Rosemarie DeCristofaro

  Callicoon Real Estate LLC

  (845) 712-9935

  23 River Rd, Callicoon, NY 12723
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  /22

  $195,000

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft

  10 Joe D Dr Unit 10B, Callicoon, NY 12723

  Resort Living at Its Finest – Villa Roma Golf Course Condo: Live like you're on vacation every day in this beautifully maintained one-story condo located at the renowned Villa Roma Resort and Golf Course. This spacious home features two bedrooms and two full bathrooms, offering comfort and ease of living in a serene setting. Enjoy your morning coffee or evening relaxation in the finished lanai,

  

  Elizabeth Bernitt

  Century 21 Geba Realty

  (845) 807-6947

  10 Joe D Dr Unit 10B, Callicoon, NY 12723
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  /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

  

  Elizabeth Bernitt

  Century 21 Geba Realty

  (845) 807-6947

  221 Gabel Rd, Callicoon, NY 12723
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  /6

  $320,000

  • Land
  • 20 Acres
  • $16,252 per Acre

  57 Boettger Rd, Callicoon, NY 12723

  Are you looking for that perfect property to build your dream home? Look no further! This property has it all! Drive up the well established shale driveway that leads to the top of this wonderful property with it's open vista looking out at the bucolic countryside. This land boasts level to gently sloping open fields, a spring fed pond, stone walls, some underground electric and a cute

  

  Dawn Curreri

  EAGLE VALLEY REALTY

  (845) 475-0469

  57 Boettger Rd, Callicoon, NY 12723
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  /50

  $699,000

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

  189 Fulton Hill Rd, Callicoon, NY 12723

  Privacy and a cozy home await you in the hills of Callicoon! Charming log cabin with front porch and deck overlooking a beautiful pond, with frontage on an even larger pond where you might train for the next Delaware River regatta! And not to forget the 26 acres of property for hiking and enjoying, a detached 2 car garage with car port in the rear, and a large barn/studio for all your creative

  

  Rosemarie DeCristofaro

  Callicoon Real Estate LLC

  (845) 385-2856

  189 Fulton Hill Rd, Callicoon, NY 12723
• 

  

  /41

  $450,000

  • 3 Beds
  • 1.5 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

  

  Elizabeth Bernitt

  Century 21 Geba Realty

  (845) 807-6947

  136 Kautz Rd, Callicoon, NY 12723
• 

  

  /21

  $190,000

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft

  11 Joe D Dr Unit 11B, Callicoon, NY 12723

  Looking for year-round fun at Villa Roma Resort in a lovely condo at the edge of a beautiful golf course? As you can see, seller and the entire family took advantage of all the fun the VR offers. Pop golfed; and the young generation enjoyed the pools, played tennis, etc. A timeshare unit is included in the sale so that you may do the same. There is a yearly maintenance fee for that unit in the

  

  Rosemarie DeCristofaro

  Callicoon Real Estate LLC

  (845) 552-1235

  11 Joe D Dr Unit 11B, Callicoon, NY 12723
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  /45

  $549,900

  • 3 Beds
  • 2 Baths
  • 1,769 Sq Ft

  18 Tammany Flats Terrace, Damascus, PA 18415

  Experience true serenity on the tranquil banks of the wild and scenic Delaware River in this extraordinary riverfront sanctuary, where every window captures awe-inspiring views of shimmering water, open skies, and the rolling countryside beyond. This enchanting chalet-style home combines rustic charm with modern elegance, offering easy, level river access for kayaking, fishing, paddleboarding, or

  

  Tim Meagher

  RE/MAX WAYNE

  (272) 225-6342

  18 Tammany Flats Terrace, Damascus, PA 18415
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  /38

  $2,250,000 New Construction

  • 6 Beds
  • 4 Baths
  • 4,015 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

  

  Sherret Chase

  Four Seasons Sotheby's Int'l R

  (845) 630-1626

  56 Winkelstern Ln, Callicoon, NY 12723
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  /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
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  /42

  $549,000

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

  5 Hess Rd, Callicoon, NY 12723

  Sustainable Catskills Retreat with Mountain Views & Solar Setup | Renovated 4BR Ranch on 2+ AcresCallicoon 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

  Barry Becker Keller Williams Hudson Valley

  5 Hess Rd, Callicoon, NY 12723
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  /42

  $398,000 Open Sat 11AM - 1PM

  • 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
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  /49

  $3,975,000

  • Land
  • 60 Acres
  • $65,899 per Acre

  356 Gabel Rd, Callicoon, NY 12723

  Unique offering! This 9-lot subdivision can make serious developers/ builders a fortune! Package consists of two beautiful upscale modern farmhouses, one is complete and one is in progress, the original 1890’s farmhouse which has been tastefully updated, two barns, PLUS 6 shovel-ready lots. The two homes are ready to be sold immediately if you choose, or establish this community as a family

  Carol Malek Malek Properties

  356 Gabel Rd, Callicoon, NY 12723
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  /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 Realty Hudson Valley United

  2585 River Rd, Damascus, PA 18415
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  /42

  $649,000

  • 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
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  /21

  $874,900

  • 3 Beds
  • 3.5 Baths
  • 2,240 Sq Ft

  Lot 7 Long Farm Way, Callicoon, NY 12723

  Welcome to ''The Long Farm''. This to-be-built home is a fabulous modern ranch design. Pictures are of the rendering, floorplan and the model in the development. Set back off a quiet country road on 8.57 acres with fabulous meadow view, this is a country house dream come true. Lots of glass lets in an abundance of natural light to fill the space and a full walk-out basement offers expansion for

  Carol Malek Malek Properties

  Lot 7 Long Farm Way, Callicoon, NY 12723
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  /22

  $949,000

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

  797 County Route 164, Callicoon, NY 12723

  Historic Charm Meets Modern Comfort in the Heart of the CatskillsBlending timeless farmhouse character with contemporary design, this stunning home has been gut renovated with impeccable taste and top-of-the-line upgrades. It’s truly turn-key—just bring your toothbrush and step into your Catskills dreamscape.Set on 3 peaceful, landscaped acres in a parklike setting, the property

  Irene Nickolai Irene Nickolai

  797 County Route 164, Callicoon, NY 12723
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  /28

  $619,000

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

  612 Beechwoods Rd, Callicoon, NY 12723

  Discover Beechwoods Cottage, an efficient newly constructed home built on 2.75 acres of serene country meadow. Located less than 15 minutes from Jeffersonville and Callicoon, and just over 2 hours from New York City, this 3-bedroom, 2-bathroom retreat offers sweeping mountain views and serves as an ideal primary residence or weekend getaway.Inside, the home features high ceilings and expansive

  William Baldwin Country House Realty Inc

  612 Beechwoods Rd, Callicoon, NY 12723
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  /33

  $695,000

  • 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

  Jared Gluckstern Country House Realty Inc

  5697 New York 52, Callicoon, NY 12723
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  /33

  $899,000

  • 4 Beds
  • 3.5 Baths
  • 2,645 Sq Ft

  276 Gabel Rd, Callicoon, NY 12723

  Welcome to “The Long Farm”. This newly constructed home is ready for your finishing touches. Now is the time to exercise your creative freedom and pick your interior options for floors, kitchen cabinets, countertops, tile and more. Set back off a quiet country road on 4+ acres with fabulous meadow and mountain views from nearly every room, this is a country house dream come true. Lots of glass

  Carol Malek Malek Properties

  276 Gabel Rd, Callicoon, NY 12723
• 

  

  /21

  $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
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  /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
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  /46

  $1,150,000

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

  Lot 3 Long Farm Way, Callicoon, NY 12723

  Welcome to ''Long Farm''. This is a to-be-built modern farmhouse (model is featured in photos) with many adjustments in floorplan, upgrades and add-ons available. This offering includes an in-ground pool to be designed according to your wishes. Begging to be the backdrop of your most memorable moments, this custom designed home will be your country house dream come true. Perfectly set back off a

  Carol Malek Malek Properties

  Lot 3 Long Farm Way, Callicoon, NY 12723
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  /50

  $385,000

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

  54 Graby Rd, Callicoon, NY 12723

  Welcome to your dream country retreat! This beautifully upgraded 3-bedroom, 2-bathroom raised ranch is nestled on 4 picturesque acres in the rolling hills of Callicoon, New York. Enjoy sweeping 360-degree views, including breathtaking sights of the distant mountains—an ideal escape for nature lovers and those seeking tranquility.Step inside to discover a newly renovated kitchen, perfect

  Dominique Jenkins Keller Williams Hudson Valley

  54 Graby Rd, Callicoon, NY 12723
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  /41

  $269,000

  • 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 generous 24-foot

  Dominique Jenkins Keller Williams Hudson Valley

  4261 State Route 17b, Callicoon, NY 12723
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  /47

  $470,000

  • 3 Beds
  • 3 Baths
  • 1,500 Sq Ft

  858 N Branch Hortonville Rd, Callicoon, NY 12745

  Classic 1931 Cape Cod Charm Meets Modern Country Living. Step into the warmth of this completely renovated 1931 Cape Cod home, where Arts and Crafts character blends seamlessly with contemporary comforts. Tucked away in a quaint country village just eight minutes from the vibrant town of Callicoon, this three-bedroom, three-bath beauty is a rare gem. Every detail has been thoughtfully updated,

  Barry Becker Keller Williams Hudson Valley

  858 N Branch Hortonville Rd, Callicoon, NY 12745
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  /31

  $329,000

  • Land
  • 32 Acres
  • $10,428 per Acre

  0 Menges Rd Unit KEY867163, Callicoon, NY 12791

  31 acres with beautiful views, ancient stone walls, fertile maintained meadows blending into a pristine forest. Perfect for a small farm or estate to build your dream house on, as the land is perfect for farming, gardening, hunting, ATV riding, and all of the outdoor sports. Prime subdivision potential here because the overall parcel is 31 acres and it consists of 3 tax parcels; two-6.38 acre

  Tom Freda Matthew J Freda Real Estate

  0 Menges Rd Unit KEY867163, Callicoon, NY 12791
• 

  

  /31

  $399,000

  • 2 Beds
  • 1 Bath
  • 1,162 Sq Ft

  117 Buddenhagen Rd, Callicoon, NY 12723

  This charming country home in Callicoon’s beautiful Beechwoods area is privately set off a quiet road. The serenity of bird song fills the air. The well-maintained Cape Cod style house is nestled nicely on a lush lawn. The vibe is completely pastoral: Surrounded by stone walls, the yard has a fenced garden area, several perennial gardens, apple trees and a mix of open and wooded areas. There’s

  Joe Freda Matthew J Freda Real Estate

  117 Buddenhagen Rd, Callicoon, NY 12723
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  /17

  $60,000

  • Land
  • 1.47 Acres
  • $40,816 per Acre

  53 Menges Rd, Callicoon, NY 12758

  Discover the potential of this 1.47-acre parcel in the picturesque Town of Callicoon! Nestled in a peaceful setting with a charming small pond, this property offers a great opportunity to build your dream home or explore various development possibilities. Zoned Settlement District (SD), the lot allows for a wide range of permitted uses—see the permitted uses list for full details. Whether you're

  Cesar Landestoy Keller Williams Hudson Valley

  53 Menges Rd, Callicoon, NY 12758
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  /33

  $349,000

  • 3 Beds
  • 1 Bath
  • 3,914 Sq Ft

  320 Fulton Hill Rd, Callicoon, NY 12723

  This converted gambrel-roof barn on a sweet country property makes a great residence for anyone who desires studio or workshop space. Featuring 3 bedrooms, an open second-floor studio, high-ceilinged 2-car garage underneath, and multiple outdoor seating/entertaining spaces, it's an easy-going, comfortable place to live. First level has hardwood floors, living room, kitchen, two bedrooms, a full

  Joe Freda Matthew J Freda Real Estate

  320 Fulton Hill Rd, Callicoon, NY 12723
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  /27

  $384,000

  • 4 Beds
  • 1.5 Baths
  • 1,880 Sq Ft

  62 Gabel Rd, Callicoon, NY 12723

  This solid brick ranch home sits on an acre of open space in the desirable Beechwoods area of Sullivan County. The front and back yard both have gorgeous 25 mile views of the valley. The home was built in 1960, and has had one owner for the last 50 plus years. It is set back off a quiet country road. It boasts three good sized bedrooms and one and a half baths, with an open floor plan. The

  John Ducey Keller Williams Hudson Valley

  62 Gabel Rd, Callicoon, NY 12723
• 

  

  /17

  $799,000

  • Land
  • 88 Acres
  • $9,080 per Acre

  0 Stump Pond Rd, Callicoon, NY 12724

  Nestled near the charming towns of Jeffersonville, Livingston Manor, Callicoon, and the Delaware National River Basin in western Sullivan County, this stunning 88-acre property in Shandelee offers a unique blend of natural beauty and potential — all for an amazing price of just $799,000!The land features 10.8 acres of open meadow with breathtaking southeastern views, ideal for building

  Diane Butler Diane C. Butler

  0 Stump Pond Rd, Callicoon, NY 12724
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  /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
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  /37

  $324,500

  • Land
  • 14 Acres
  • $23,686 per Acre

  Dyker Road Dyker Rd, Callicoon, NY 12766

  10+ acres of gently sloping open meadow with southern exposure and stunning views. Ideal building site located in Western Sullivan County, just a short distance from the Delaware River National Park. Enjoy easy living in a country setting nestled amidst farmland, yet still close to town. Local attractions include the Bethel Woods Performing Arts Center, the Kartrite Water Park, and excellent

  Diane Butler Diane C. Butler

  Dyker Road Dyker Rd, Callicoon, NY 12766
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  /35

  $269,000

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  23 Peters Rd, Callicoon, NY 12723

  Build your house on these 17 acres with spectacular sunset views. 2 handyman mobile homes, with one well, overlooking the property. Mostly open meadows and farm fields. A small spring-run courses through the lower part of the property. Both mobile homes are in As-Is condition and needs lots of work or removal for a new home. Wonderful sweeping views of the Catskill mountains and a perfect site

  Tom Freda Matthew J Freda Real Estate

  23 Peters Rd, Callicoon, NY 12723
• 

  

  /11

  $465,000

  • Land
  • 54 Acres
  • $8,674 per Acre

  0 Shandelee Rd Unit KEY804620, Callicoon, NY 12758

  Gorgeous property in Livingston Manor! Look no further for privacy and serenity, this property is about a half mile from the county road and is the ultimate nature lover's paradise. Upon entering the property you will find approximately half an acre of cleared land, perfect to build your dream home! The rest of the 50+ acres are a wonderful combination of level ground, slopes and curves, as well

  Victoria Wander Divine Realty NY, LLC

  0 Shandelee Rd Unit KEY804620, Callicoon, NY 12758
• 

  

  /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
• 

  

  /11

  $330,000

  • Land
  • 10 Acres
  • $33,000 per Acre

  00 Beechwoods Rd, Callicoon, NY 12723

  Etherial eastern skies stretch for miles beyond this serene crown jewel property in the coveted Callicoon Beechwoods. Imagine raising free range grass fed livestock within sight of your kitchen window. Tree lined meadows laden with majestic apple and pear trees adorn this exceptional pastural paradise. A harmonious mix of level fields and sloping forests create a natural sanctuary for a small

  Owen Boller Boller Properties

  00 Beechwoods 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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