Callicoon, NY Homes

• 

  $217,500

  Sold Feb 23, 2026

  4261 State Route 17b, Callicoon, NY 12723

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1995

  Last Sold Summary

  • 19% Below List Price
  • $155/SF
  • 166 Days On Market

  Current Estimated Value $226,758

  Last Listing Agent Dominique Jenkins KW Hudson Valley United

  4261 State Route 17b, Callicoon, NY 12723
• 

  Est $370,766

  Not Listed For Sale

  117 Buddenhagen Rd, Callicoon, NY 12723

  • 2 Beds
  • 1 Bath
  • 1,162 Sq Ft
  • Built 1976

  117 Buddenhagen Rd, Callicoon, NY 12723

  Last Sold Summary

  • 93 Days On Market

  Last Listing Agent Joe Freda Matthew J Freda Real Estate
• 

  

  

  /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
• 

  $92,000

  Sold Jul 15, 2026

  0 Bethlehem Rd Unit KEY987885, Callicoon, NY 12724

  • Land
  • 12 Acres
  • $7,667 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 40 Days On Market

  Last Listing Agent Joe Freda Matthew J Freda Real Estate

  0 Bethlehem Rd Unit KEY987885, Callicoon, NY 12724
• 

  Est $545,208

  Not Listed For Sale

  23 River Rd, Callicoon, NY 12723

  • 2 Beds
  • 2 Baths
  • 1,496 Sq Ft
  • Built 1873

  23 River Rd, Callicoon, NY 12723

  Last Sold Summary

  • 85 Days On Market

  Last Listing Agent Rosemarie DeCristofaro Callicoon Real Estate LLC
• 

  

  /45

  $349,000

  $50K PRICE DROP Pending

  • 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
• 

  $266,000

  Sold Aug 05, 2026

  9568 State Route 97, Callicoon, NY 12723

  • 2 Beds
  • 1 Bath
  • 1,159 Sq Ft
  • Built 1973

  Last Sold Summary

  • 17% Below List Price
  • $230/SF
  • 309 Days On Market

  Current Estimated Value $303,333

  Last Listing Agent Susan Busing Matthew J Freda Real Estate

  9568 State Route 97, Callicoon, NY 12723
• 

  Est $289,339

  Not Listed For Sale

  881 County Route 164, Callicoon, NY 12723

  • 3 Beds
  • 1 Bath
  • 1,104 Sq Ft
  • Built 1972

  881 County Route 164, Callicoon, NY 12723

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Lynelle Alessi KW Hudson Valley United
• 

  

  /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
• 

  $227,500

  Sold Oct 30, 2025

  Dyker Road Dyker Rd, Callicoon, NY 12766

  • Land
  • 13.7 Acres
  • $16,606 per Acre

  Last Sold Summary

  • 24% Below List Price
  • 185 Days On Market

  Last Listing Agent Diane Butler Diane C. Butler

  Dyker Road Dyker Rd, Callicoon, NY 12766
• 

  Est $383,944

  Not Listed For Sale

  54 Del Vue Rd, Callicoon, NY 12723

  • 4 Beds
  • 2 Baths
  • 1,734 Sq Ft
  • Built 1990

  54 Del Vue Rd, Callicoon, NY 12723

  Last Sold Summary

  • 151 Days On Market

  Last Listing Agent Lynne Freda Matthew J Freda Real Estate
• 

  

  /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
• 

  $225,000

  Sold Feb 26, 2026

  93 Villa Roma Rd, Callicoon, NY 12723

  • 3 Beds
  • 1 Bath
  • 1,450 Sq Ft
  • Built 1840

  Last Sold Summary

  • 25% Below List Price
  • $155/SF
  • 448 Days On Market

  Last Listing Agent Joe Freda Matthew J Freda Real Estate

  93 Villa Roma Rd, Callicoon, NY 12723
• 

  Est $520,551

  Not Listed For Sale

  27 Gabel Rd, Callicoon, NY 12723

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • Built 1962

  27 Gabel Rd, Callicoon, NY 12723

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Steven Beeson Diane C. Butler
• 

  

  /46

  $1,299,999

  Pending

  • 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
• 

  $175,000

  Sold Oct 15, 2025

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

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1996

  Last Sold Summary

  • 8% Below List Price
  • $152/SF
  • 45 Days On Market

  Current Estimated Value $179,757

  Last Listing Agent Rosemarie DeCristofaro Callicoon Real Estate LLC

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

  Est $416,159

  Not Listed For Sale

  155 Graby Rd, Callicoon, NY 12723

  • 4 Beds
  • 2.5 Baths
  • 1,624 Sq Ft
  • Built 1978

  155 Graby Rd, Callicoon, NY 12723

  Last Sold Summary

  • 89 Days On Market

  Last Listing Agent Lynne Freda Matthew J Freda Real Estate
• 

  

  /11

  $285,000

  • Land
  • 53.61 Acres
  • $5,316 per Acre

  0 Shandelee Rd Unit KEY1005045, Callicoon, NY 12758

  Gorgeous acreage for sale in the highly sought after 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

  Victoria Wander Divine Realty NY, LLC

  0 Shandelee Rd Unit KEY1005045, Callicoon, NY 12758
• 

  $899,000

  Sold Aug 25, 2026

  797 County Route 164, Callicoon, NY 12723

  • 5 Beds
  • 2 Baths
  • 2,800 Sq Ft
  • Built 1842

  Last Sold Summary

  • 5% Below List Price
  • $321/SF
  • 58 Days On Market

  Current Estimated Value $925,616

  Last Listing Agent Elizabeth Bernitt Century 21 Geba Realty

  797 County Route 164, Callicoon, NY 12723
• 

  Not Listed For Sale

  186 County Route 164, Callicoon, NY 12723

  • 5 Beds
  • 4.5 Baths
  • 3,186 Sq Ft
  • Built 1985

  186 County Route 164, Callicoon, NY 12723

  Last Sold Summary

  • 535 Days On Market

  Last Listing Agent Ian Blumenthal Catskill Sales Associates Inc
• 

  

  /47

  $339,000

  • 5 Beds
  • 2 Baths
  • 2,688 Sq Ft

  6 County Route 121, Callicoon, NY 12723

  Endless possibilities meet location! Zoned for both commercial and residential use, this unique property offers incredible flexibility for savvy buyers, investors, or entrepreneurs.Situated right on Route 17B at the crossroads of Callicoon, North Branch, and Hortonville, the building is currently configured as two separate living spaces, each featuring its own kitchen and

  Steven Beeson Diane C. Butler

  6 County Route 121, Callicoon, NY 12723
• 

  /2

  $325,000

  Sold Dec 19, 2025

  215 Kautz Rd, Callicoon, NY 12723

  • 4 Beds
  • 2 Baths
  • 1,740 Sq Ft
  • Built 1980

  Last Sold Summary

  • 26% Below List Price
  • $187/SF
  • 24 Days On Market

  Current Estimated Value $361,095

  Last Listing Agent Joan Hale Listing by Howard Hanna

  

  215 Kautz Rd, Callicoon, NY 12723
• 

  Est $437,342

  Not Listed For Sale

  520 Beechwoods Rd, Callicoon, NY 12723

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 2001

  520 Beechwoods Rd, Callicoon, NY 12723

  Last Sold Summary

  • 186 Days On Market

  Last Listing Agent Rosemarie DeCristofaro Callicoon Real Estate LLC
• 

  

  /31

  $989,000

  • 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

  32 Long Farm Way, Callicoon, NY 12723
• 

  

  /41

  $1,100,000

  Sold Oct 10, 2025

  1556 Gulf Rd, Callicoon, NY 12776

  • 4 Beds
  • 2 Baths
  • 2,108 Sq Ft
  • Built 1880

  Last Sold Summary

  • 12% Below List Price
  • $522/SF
  • 70 Days On Market

  Current Estimated Value $1,081,213

  Last Listing Agent Robin Jones Anatole House LLC

  1556 Gulf Rd, Callicoon, NY 12776
• 

  Est $422,728

  Not Listed For Sale

  264 Robisch Hill Rd, Callicoon, NY 12723

  • 4 Beds
  • 2 Baths
  • 1,584 Sq Ft
  • Built 1982

  264 Robisch Hill Rd, Callicoon, NY 12723

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Lynne Freda Matthew J Freda Real Estate
• 

  

  /33

  $179,900

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

  4 Joe D Dr Unit 4C, Callicoon, NY 12723

  Your Catskills escape awaits! This inviting 2-bedroom, 2-bathroom condo at Villa Roma offers the perfect blend of comfort, recreation and resort-style living.Enjoy access to an incredible range of amenities and activities, including indoor and outdoor pools, golf, tennis, pickleball, hot tubs, dining, live entertainment, skiing, snowboarding, snow tubing and more.Whether you're

  Joshua Murphy Woodstock Way Realty LLC

  4 Joe D Dr Unit 4C, Callicoon, NY 12723
• 

  $1,350,000

  Sold Jan 23, 2026

  59 Overlook Dr, Callicoon, NY 12723

  • 4 Beds
  • 4 Baths
  • 3,200 Sq Ft
  • Built 2017

  Last Sold Summary

  • 43% Below List Price
  • $422/SF
  • 550 Days On Market

  Current Estimated Value $1,356,357

  Last Listing Agent Joe Freda Matthew J Freda Real Estate

  59 Overlook Dr, Callicoon, NY 12723
• 

  Est $671,229

  Not Listed For Sale

  279 Kautz Rd, Callicoon, NY 12723

  • 4 Beds
  • 3.5 Baths
  • 2,690 Sq Ft
  • Built 1979

  279 Kautz Rd, Callicoon, NY 12723

  Last Sold Summary

  • 83 Days On Market

  Last Listing Agent Heather Quaintance Country House Realty Inc
• 

  

  /30

  $75,000

  $14K PRICE DROP

  • Land
  • 8 Acres
  • $9,375 per Acre

  0 Hubert Rd, Callicoon, NY 12748

  This 8-acre property features beautiful mountain and valley views and is located on a quiet country road outside of Jeffersonville in the western Catskills. Approximately one-third of this lot is open and cleared and the back portion is wooded. The terrain is level to gently sloping and the back wooded portion of the lot features some clearings, stone walls and a spring feeding into a small

  Linda Mulligan Matthew J Freda Real Estate

  0 Hubert Rd, Callicoon, NY 12748
• 

  $975,000

  Sold Sep 24, 2026

  118 Froehlich Dr, Callicoon, NY 12723

  • 3 Beds
  • 2.5 Baths
  • 2,821 Sq Ft
  • Built 2008

  Last Sold Summary

  • 13% Below List Price
  • $346/SF
  • 65 Days On Market

  Current Estimated Value $980,137

  Last Listing Agent Fran Limjoon Gager R J Katz Realty

  118 Froehlich Dr, Callicoon, NY 12723
• 

  Est $76,918

  Not Listed For Sale

  26 Fulton Hill Rd, Callicoon, NY 12723

  • 2 Beds
  • Built 1920

  26 Fulton Hill Rd, Callicoon, NY 12723

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Nancy Barnhart Elliott & Pomeroy Inc
• 

  

  /11

  $225,000

  • Land
  • 2.83 Acres
  • $79,505 per Acre

  Lot 22 & 23 County Road 164, Callicoon, NY 12723

  This 2.83 acre vacant lot offers a premium building opportunity in the highly desirable Beechwood's area ofCallicoon, NY. Almost directly across the Street from the Villa Roma County Club and Golf Course, and very close to the Villa Roma Resort, the property provides an exceptional blend of rural privacy and immediate proximity to world-class resort amenities .

  Linda Vairo Wrighter Listing by Land and Water Realty LLC

  

  Lot 22 & 23 County Road 164, Callicoon, NY 12723
• 

  $340,000

  Sold May 22, 2026

  463 County Road 131, Callicoon, NY 12723

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1985

  Last Sold Summary

  • 5% Below List Price
  • $322/SF
  • 144 Days On Market

  Current Estimated Value $376,605

  Last Listing Agent Jonathan Minerick HomeCoin.com

  463 County Road 131, Callicoon, NY 12723
• 

  Est $404,948

  Not Listed For Sale

  5777 State Route 52, Callicoon, NY 12723

  • 2 Beds
  • 1 Bath
  • 644 Sq Ft
  • Built 1930

  5777 State Route 52, Callicoon, NY 12723

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent William Baldwin Country House Realty Inc
• 

  

  /62

  $1,450,000

  Under Contract

  • 4 Beds
  • 2.5 Baths
  • 3,000 Sq Ft

  506 Beechwoods Rd, Callicoon, NY 12723

  Welcome to the Beechwoods, a disarmingly bucolic pocket of Sullivan County dotted with cattle lazing by a stream and sheep foraging across rolling hills. Here in the agrarian calm, high above Callicoon, sits the Beechwoods House, looking out across one of the western Catskills' most beautiful landscapes: undulating farmland, wooded hills and an extraordinary expanse of sky. Set within 7.85 acres

  Angelica VonDrak Houlihan Lawrence, Inc.

  506 Beechwoods Rd, Callicoon, NY 12723
• 

  $220,000

  Sold Nov 21, 2025

  23 Peters Rd, Callicoon, NY 12723

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft
  • Built 1970

  Last Sold Summary

  • 18% Below List Price
  • $327/SF
  • 261 Days On Market

  Last Listing Agent Tom Freda Matthew J Freda Real Estate

  23 Peters Rd, Callicoon, NY 12723
• 

  Est $228,396

  Not Listed For Sale

  3462 State Route 17b, Callicoon, NY 12723

  • 2 Beds
  • 1 Bath
  • 676 Sq Ft
  • Built 1963

  3462 State Route 17b, Callicoon, NY 12723

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Kerry Bigness Malek Properties
• 

  

  /32

  $575,000

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

  84 Kratz Rd, Callicoon, NY 12723

  Tucked down a long driveway, Valley View is perched along a ridge enjoying two of the finest amenities houses can offer: views and privacy. Valley View is rich in country charm and coziness, with a flexible chalet layout sure to work well as a countryside retreat.Entering the house from the handsome entryway, you’re greeted with a classic chalet layout and cabin feel - bedroom and

  Jared Gluckstern Country House Realty Inc

  84 Kratz Rd, Callicoon, NY 12723
• 

  $350,000

  Sold Oct 24, 2025

  54 Graby Rd, Callicoon, NY 12723

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1977

  Last Sold Summary

  • 9% Below List Price
  • $250/SF
  • 48 Days On Market

  Current Estimated Value $383,556

  Last Listing Agent Dominique Jenkins KW Hudson Valley United

  54 Graby Rd, Callicoon, NY 12723

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