Callicoon Township Sullivan, NY Homes

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  /42

  $899,000

  $50K PRICE DROP Pending

  • 4 Beds
  • 3 Baths
  • 1,875 Sq Ft

  1680 Gulf Rd, Callicoon Center, NY 12724

  Overbrook House is a design-forward Catskills retreat on nearly an acre that lives much larger thanks to multiple eye-popping indoor/outdoor spaces including a dreamy separate Guest Studio (included in beds/baths and square footage). The meticulously styled main house features a den paneled with reclaimed barnwood, while the more formal living room's gas fireplace is great for ease of use and

  Jennifer Grimes Country House Realty, Inc.

  1680 Gulf Rd, Callicoon Center, NY 12724
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• 

  $605,000

  Sold Jun 30, 2026

  381 Dutch Hill Rd, Roscoe, NY 12776

  • 5 Beds
  • 3 Baths
  • 1,158 Sq Ft
  • Built 1988

  Last Sold Summary

  • 2% Below List Price
  • $522/SF
  • 42 Days On Market

  Current Estimated Value $613,563

  Last Listing Agent Carole Edwards Carole Edwards Realty

  381 Dutch Hill Rd, Roscoe, NY 12776
• 

  Est $296,654

  Not Listed For Sale

  4122 State Route 52, Youngsville, NY 12791

  • 4 Beds
  • 2 Baths
  • 1,888 Sq Ft
  • Built 1920

  4122 State Route 52, Youngsville, NY 12791

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent Susan Busing Matthew J Freda Real Estate
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  /40

  $299,900

  Pending

  • 4 Beds
  • 2 Baths
  • 1,620 Sq Ft

  4188 State Route 52, Youngsville, NY 12791

  Mobile-home in very good condition set on one acre just outside Youngsville NY. Many amenities and quality upgrades went into this 4 bedroom 2 full bath home. There are stainless kitchen appliances and a large kitchen island with plenty of cabinetry. Laundry room with washer and dryer. It has is central air and heat (propane), an alarm system, camera system for security, new septic system,

  Steven Beeson Diane C. Butler

  4188 State Route 52, Youngsville, NY 12791
• 

  $261,000

  Sold May 22, 2026

  57 Menges Rd, Youngsville, NY 12791

  • 3 Beds
  • 1.5 Baths
  • 1,688 Sq Ft
  • Built 1924

  Last Sold Summary

  • 22% Below List Price
  • $155/SF
  • 271 Days On Market

  Current Estimated Value $351,197

  Last Listing Agent Sean Walker Keller Williams Realty

  57 Menges Rd, Youngsville, NY 12791
• 

  Est $519,153

  Not Listed For Sale

  879 Shandelee Rd, Livingston Manor, NY 12758

  • 3 Beds
  • 2 Baths
  • 1,498 Sq Ft
  • Built 2015

  879 Shandelee Rd, Livingston Manor, NY 12758

  Last Sold Summary

  • 67 Days On Market

  Last Listing Agent William Baldwin Country House Realty Inc
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  /4

  $329,900

  • 5 Beds
  • 2.5 Baths
  • 2,781 Sq Ft

  4369 State Route 52, Jeffersonville, NY 12748

  Diamond in the rough. Main house has been used as a two family in years past, building at back of property has one 3 bedroom, one bath apartment and the other apartment has been started but not completed. This property consists of 15 +- acres located in the RB district in the town of Callicoon, which means several possibilities for development including gas station. The East branch of the

  Ian Blumenthal Catskill Sales Associates Inc

  4369 State Route 52, Jeffersonville, NY 12748
• 

  $765,000

  Sold Apr 24, 2026

  526 Jeffersonville North Branch Rd, North Branch, NY 12766

  • 4 Beds
  • 4 Baths
  • 2,912 Sq Ft
  • Built 1985

  Last Sold Summary

  • 18% Above List Price
  • $263/SF
  • 42 Days On Market

  Last Listing Agent Jared Gluckstern Country House Realty Inc

  526 Jeffersonville North Branch Rd, North Branch, NY 12766
• 

  Est $253,835

  Not Listed For Sale

  367 Hemmer Rd, Livingston Manor, NY 12758

  • 2 Beds
  • 1 Bath
  • 1,040 Sq Ft
  • Built 1984

  367 Hemmer Rd, Livingston Manor, NY 12758

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Ian Blumenthal Catskill Sales Associates Inc
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  /36

  $549,000

  $20K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,663 Sq Ft

  4741 State Route 52, Jeffersonville, NY 12748

  Enjoy unforgettable sunsets from this beautifully renovated 4 bedroom, 3 bath home set on 1.5 acres. Designed for both comfort and entertaining, the home features oversized double back decks that seamlessly extend your living space outdoors. Inside, warm wood floors, recessed lighting, and spacious rooms create a bright and inviting atmosphere, complemented by large walk in closets and a

  Tammy Ierardi Modern Solutions Realty, LLC

  4741 State Route 52, Jeffersonville, NY 12748
• 

  $290,000

  Sold Jan 29, 2026

  31 Erlemann Rd, Jeffersonville, NY 12748

  • 2 Beds
  • 2 Baths
  • 1,184 Sq Ft
  • Built 1975

  Last Sold Summary

  • 3% Below List Price
  • $245/SF
  • 49 Days On Market

  Current Estimated Value $307,467

  Last Listing Agent Susan Busing Matthew J Freda Real Estate

  31 Erlemann Rd, Jeffersonville, NY 12748
• 

  Est $324,364

  Not Listed For Sale

  345 Hessinger Lare Rd, Livingston Manor, NY 12758

  • 2 Beds
  • 2 Baths
  • 1,318 Sq Ft
  • Built 1960

  345 Hessinger Lare Rd, Livingston Manor, NY 12758

  Last Sold Summary

  • 97 Days On Market

  Last Listing Agent Ian Blumenthal Catskill Sales Associates Inc
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  /6

  $349,900

  • Land
  • 35 Acres
  • $9,997 per Acre

  TBD Jeffersonville North Branch Rd, Jeffersonville, NY 12748

  Discover the perfect setting for your dream home, country getaway, or recreational retreat on this beautiful 35± acre property in Western Sullivan County. A gentle rise in elevation creates stunning bucolic views and offers multiple ideal building sites to take advantage of the picturesque landscape. Featuring a wonderful blend of open meadows and wooded areas, the property is rich in character

  Carol Malek Malek Properties

  TBD Jeffersonville North Branch Rd, Jeffersonville, NY 12748
• 

  $398,000

  Sold Mar 18, 2026

  807 Swiss Hill Rd N, Jeffersonville, NY 12748

  • 4 Beds
  • 2.5 Baths
  • 3,634 Sq Ft
  • Built 1895

  Last Sold Summary

  • 33% Below List Price
  • $110/SF
  • 572 Days On Market

  Current Estimated Value $478,124

  Last Listing Agent Dawn Curreri Eagle Valley Realty

  807 Swiss Hill Rd N, Jeffersonville, NY 12748
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  Not Listed For Sale

  570 Dutch Hill Rd, Roscoe, NY 12776

  • 5 Beds
  • Built 1900

  570 Dutch Hill Rd, Roscoe, NY 12776

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Ellie Hyde Century 21 Country Realty
• 

  

  /35

  $292,000

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft

  4088 State Route 52, Youngsville, NY 12791

  Set on a full acre in the heart of Youngsville, this well-built and lovingly updated home offers comfort, charm, and true move-in-ready ease. Ideally located just minutes from the historic Village of Jeffersonville, you'll enjoy convenient access to unique shops, restaurants, grocery stores, boutiques, parks, and numerous amenities all while savoring a peaceful country setting. Inside, the home

  Deborah Gorenflo Land and Water Realty LLC

  4088 State Route 52, Youngsville, NY 12791
• 

  $730,000

  Sold Dec 18, 2025

  292 Sander Rd, Jeffersonville, NY 12748

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • Built 1900

  Last Sold Summary

  • 1% Below List Price
  • $304/SF
  • 71 Days On Market

  Current Estimated Value $734,760

  Last Listing Agent Jeff Gardner Corcoran MH, LLC

  292 Sander Rd, Jeffersonville, NY 12748
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  /2

  Est $259,546

  Not Listed For Sale

  14 Jefferson Ave, Jeffersonville, NY 12748

  • 3 Beds
  • 1 Bath
  • 1,387 Sq Ft
  • Built 1930

  

  14 Jefferson Ave, Jeffersonville, NY 12748

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent Dara Barr Listing by Keller Williams Upstate NY Properties
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  /43

  $220,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,904 Sq Ft

  673 Hessinger and Lare Rd, Jeffersonville, NY 12748

  Enjoy space, scenery, and easy access to the best of the Sullivan Catskills with this well-maintained 3-bedroom, 2-bath mobile home set on 4.42 acres. The home features a large living room, comfortable layout, and plenty of room to relax indoors or out.A spacious deck accented by natural wood and stone invites you to take in the beautiful views and enjoy quiet mornings, outdoor meals, or

  Anna Milucky Century 21 Country Realty

  673 Hessinger and Lare Rd, Jeffersonville, NY 12748
• 

  $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 $286,162

  Not Listed For Sale

  172 Stewart Rd, North Branch, NY 12766

  • 3 Beds
  • 1 Bath
  • 1,093 Sq Ft
  • Built 1961

  172 Stewart Rd, North Branch, NY 12766

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent John Ducey KW Hudson Valley United
• 

  

  /26

  $175,000

  • Land
  • 15.16 Acres
  • $11,544 per Acre

  52 E Hill Rd, Jeffersonville, NY 12748

  This exceptional parcel with great views offers a rare combination of location, accessibility, and homesite potential. Situated in a desirable and growing area, the expansive property features optimal topography, excellent road frontage, and convenient access to many local towns including Jeffersonville, Callicoon, LIberty and Roscoe where you'll find many of the areas restaurants and shopping.

  Steven Beeson Diane C. Butler

  52 E Hill Rd, Jeffersonville, NY 12748
• 

  $105,000

  Sold Nov 05, 2025

  28 Schaefer Rd, Jeffersonville, NY 12748

  • 3 Beds
  • 2.5 Baths
  • 2,430 Sq Ft
  • Built 2004

  Last Sold Summary

  • $43/SF
  • 22 Days On Market

  Last Listing Agent Emma Djiya 1st Class Realty

  28 Schaefer Rd, Jeffersonville, NY 12748
• 

  Est $182,591

  Not Listed For Sale

  50 Jefferson Ave, Jeffersonville, NY 12748

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1920

  50 Jefferson Ave, Jeffersonville, NY 12748

  Last Sold Summary

  • 335 Days On Market

  Last Listing Agent Ian Blumenthal Catskill Sales Associates Inc
• 

  

  /10

  $399,999

  $15K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,781 Sq Ft

  1751 Shandelee Rd, Livingston Manor, NY 12758

  Fully Remodeled Ranch in the Heart of Youngsville. Welcome to this beautifully updated 3-bedroom, 2-bath ranch-style home situated on 1.56 peaceful acres in the heart of Youngsville! This move-in ready property offers the perfect blend of comfort, space, and outdoor living. Inside, you’ll find a fully remodeled interior with a bright and inviting layout, including a spacious sunroom, gorgeous

  Jonathan Minerick HomeCoin.com

  1751 Shandelee Rd, Livingston Manor, NY 12758
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  /35

  $385,000

  Sold Oct 03, 2025

  206 Yaun Rd, Livingston Manor, NY 12758

  • 4 Beds
  • 3 Baths
  • 2,080 Sq Ft
  • Built 1970

  Last Sold Summary

  • 19% Below List Price
  • $185/SF
  • 287 Days On Market

  Current Estimated Value $426,481

  Last Listing Agent Carol Malek Malek Properties, Inc.

  206 Yaun Rd, Livingston Manor, NY 12758
• 

  Est $296,527

  Not Listed For Sale

  65 Shandelee Lake Rd, Livingston Manor, NY 12758

  • 2 Beds
  • 2.5 Baths
  • 1,056 Sq Ft
  • Built 1940

  65 Shandelee Lake Rd, Livingston Manor, NY 12758

  Last Sold Summary

  • 245 Days On Market

  Last Listing Agent Catherine Eichner Eichner Realty Group Inc.
• 

  

  /35

  $299,000

  Pending

  • Land
  • 32.47 Acres
  • $9,209 per Acre

  0 Menges Rd Unit KEY976899, Callicoon, NY 12791

  32 acres-wooded with stream. Drive up to the property off a quiet paved road and walk into it through a pristine meadow that is dotted with wild blueberry bushes. Walking further into a mature stand of maple, birch, cherry and other assorted trees, you will find cairns and stone walls that are along the edges and interior of the land. There is a small stream that runs through the back of the

  Tom Freda Matthew J Freda Real Estate

  0 Menges Rd Unit KEY976899, Callicoon, NY 12791
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  /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 $251,283

  Not Listed For Sale

  404 Hemmer Rd, Livingston Manor, NY 12758

  • 3 Beds
  • 1 Bath
  • 1,104 Sq Ft
  • Built 1970

  404 Hemmer Rd, Livingston Manor, NY 12758

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Ian Blumenthal Catskill Sales Associates Inc
• 

  

  /20

  $399,900

  • Land
  • 70 Acres
  • $5,713 per Acre

  301 & 305 Hust Road Hust Rd, Jeffersonville, NY 12748

  stunning building lot with plenty of room to grow. Long distance views, fields meadows and starry night skys. Unimproved raw land on the edge of a farm.

  Diane Butler Diane C. Butler

  301 & 305 Hust Road Hust Rd, Jeffersonville, NY 12748
• 

  $575,000

  Sold Oct 15, 2025

  178 Grebel Rd, Jeffersonville, NY 12748

  • 2 Beds
  • 2 Baths
  • 1,404 Sq Ft
  • Built 2017

  Last Sold Summary

  • 4% Below List Price
  • $410/SF
  • 42 Days On Market

  Current Estimated Value $580,593

  Last Listing Agent Sean Drown Land and Water Realty LLC

  178 Grebel Rd, Jeffersonville, NY 12748
• 

  Est $253,066

  Not Listed For Sale

  185 N Branch Callicoon Ctr Rd, North Branch, NY 12766

  • 2 Beds
  • Built 1949

  185 N Branch Callicoon Ctr Rd, North Branch, NY 12766

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Thelonious Johnson Hart & Johnson Realty
• 

  

  /34

  $650,000

  $25K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,351 Sq Ft

  22 J Spielman Rd, Jeffersonville, NY 12748

  Let country roads take you home to this charming retreat, set on a beautifully private parcel. Tucked deep into the rolling hills of Jeffersonville, this well-maintained and recently updated, custom-built 2004 home delivers a rare combination of total privacy, timeless craftsmanship, and stylish modern updates—all just minutes from town. Set far back from the road amid native landscaping, private

  Heather Quaintance Country House Realty Inc

  22 J Spielman Rd, Jeffersonville, NY 12748
• 

  $505,000

  Sold Sep 30, 2025

  271 Hemmer Rd, Youngsville, NY 12791

  • 3 Beds
  • 2 Baths
  • 1,626 Sq Ft
  • Built 1991

  Last Sold Summary

  • 13% Below List Price
  • $311/SF
  • 33 Days On Market

  Last Listing Agent Jane Panico Realty Promotions Inc

  271 Hemmer Rd, Youngsville, NY 12791
• 

  Est $286,814

  Not Listed For Sale

  35 Back Shandelee Rd, Livingston Manor, NY 12758

  • 4 Beds
  • 2 Baths
  • 1,440 Sq Ft
  • Built 1984

  35 Back Shandelee Rd, Livingston Manor, NY 12758

  Last Sold Summary

  • 143 Days On Market

  Last Listing Agent Deborah Gorenflo Land and Water Realty LLC
• 

  

  /23

  $330,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,378 Sq Ft

  40 Jefferson Ave, Jeffersonville, NY 12748

  Enjoy the convenience of in-town living at this newly gut renovated brick ranch in Jeffersonville, NY. Bright, airy, easy single floor living with modern upgrades make this a great family home, or potential investment as a rental property. Fully renovated in 2023, the home features a brand new kitchen, bathroom, windows, hot water heater, and back deck. There are three ground floor bedrooms and

  Jared Gluckstern Country House Realty Inc

  40 Jefferson Ave, Jeffersonville, NY 12748
• 

  $282,500

  Sold Oct 24, 2025

  704 Cattail Rd, Livingston Manor, NY 12758

  • 3 Beds
  • 1.5 Baths
  • 1,350 Sq Ft
  • Built 1989

  Last Sold Summary

  • 6% Below List Price
  • $209/SF
  • 62 Days On Market

  Current Estimated Value $305,196

  Last Listing Agent Kewin Garabito eXp Realty

  704 Cattail Rd, Livingston Manor, NY 12758
• 

  Est $430,557

  Not Listed For Sale

  18 Center St, Jeffersonville, NY 12748

  • 4 Beds
  • 2.5 Baths
  • 2,247 Sq Ft
  • Built 1910

  18 Center St, Jeffersonville, NY 12748

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Ian Blumenthal Catskill Sales Associates Inc
• 

  

  /54

  $599,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,080 Sq Ft

  49 Yaun Rd, Livingston Manor, NY 12758

  Hollyhock sits a long way back from a quiet country road on 10.13 acres of meadow, woods, and historic stone walls. The house is properly private and still only a few minutes from Livingston Manor's main street, which is the increasingly rare combination people drive up here to find. The interiors are where it gets interesting: someone has been making confident, pattern-loving, vintage-respecting

  Arlena Armstrong Anatole House LLC

  49 Yaun Rd, Livingston Manor, NY 12758

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