# 28 Upper Main Street, Callicoon, NY 12723 > **TL;DR:** 7bd/4ba single family, $749,999 ($153/sqft), built 1885, 4,900 sqft. Est. $4,011/mo. Listed 28 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $749,999 | | Price/sqft | $153 | | Bedrooms | 7 | | Bathrooms | 2 full, 2 half | | Square Feet | 4,900 | | Year Built | 1885 | | Lot Size | 7,841 sqft (0.18 acres) | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 28 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $3,792 | | Estimated Insurance | $219 | | **Total** | **$4,011** | ## Nearby Schools - **Elementary:** Sullivan West Elementary - **Middle:** SULLIVAN WEST HIGH SCHOOL AT LAKE HUNTINGTON - **High:** Sullivan West High School At Lake Huntington ## Property Highlights - Built in 1885 - 0.18 acre lot ## Description ### Agent Description 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 rooms, providing multiple income streams and operational flexibility. Rich in character and history, Rafters is well-positioned for continued success as one of the area's most popular gathering places for dining, entertainment, and live performances. The property also includes an additional commercial space suitable for retail or complementary business use. Heating/Cooling system: propane upstairs, forced air and central AC, downstairs electric heating & cooling units ## Location - **Address:** 28 Upper Main Street, Callicoon, NY 12723 - **County:** Sullivan County - **Coordinates:** 41.767125, -75.057819 - **Google Maps:** https://www.google.com/maps?q=41.767125,-75.057819 ## Virtual Tour & Media - **Video Tour:** https://www.zillow.com/view-imx/f544b33c-775b-4e4f-b322-8d9697 ## Listing Agent - **Name:** Gregory A. Berkowitz - **Brokerage:** Laffey International Realt Estate - **Phone:** 5165267775 - **Broker Phone:** (516) 308-0550 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/28-Upper-Main-St_Callicoon_NY_12723_M39895-24929?f=listhub&s=MLSLINY&m=1040279&c=propsimple) ## Photos ![28 Upper Main Street - Photo 1](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f2057578497r.jpg) ![28 Upper Main Street - Photo 2](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f4145452538r.jpg) ![28 Upper Main Street - Photo 3](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f3170814504r.jpg) ![28 Upper Main Street - Photo 4](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f1231097245r.jpg) ![28 Upper Main Street - Photo 5](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f3944389077r.jpg) ![28 Upper Main Street - Photo 6](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f2296856321r.jpg) ![28 Upper Main Street - Photo 7](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f1699659707r.jpg) ![28 Upper Main Street - Photo 8](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f3768600342r.jpg) ![28 Upper Main Street - Photo 9](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f407338366r.jpg) ![28 Upper Main Street - Photo 10](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f286803495r.jpg) ![28 Upper Main Street - Photo 11](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f2073884r.jpg) ![28 Upper Main Street - Photo 12](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f2707131947r.jpg) ![28 Upper Main Street - Photo 13](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f2708362124r.jpg) ![28 Upper Main Street - Photo 14](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f2646573031r.jpg) ![28 Upper Main Street - Photo 15](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f3200827821r.jpg) ![28 Upper Main Street - Photo 16](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f2440715859r.jpg) ![28 Upper Main Street - Photo 17](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f4202090015r.jpg) ![28 Upper Main Street - Photo 18](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f76305419r.jpg) ![28 Upper Main Street - Photo 19](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f560843356r.jpg) ![28 Upper Main Street - Photo 20](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f1390866942r.jpg) ![28 Upper Main Street - Photo 21](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f3707777890r.jpg) ![28 Upper Main Street - Photo 22](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f3516382333r.jpg) ![28 Upper Main Street - Photo 23](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f2909351028r.jpg) ![28 Upper Main Street - Photo 24](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f1762279326r.jpg) ![28 Upper Main Street - Photo 25](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f3411160023r.jpg) ![28 Upper Main Street - Photo 26](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f3342440374r.jpg) ![28 Upper Main Street - Photo 27](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f3623125779r.jpg) ![28 Upper Main Street - Photo 28](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f3537527410r.jpg) ![28 Upper Main Street - Photo 29](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f581884972r.jpg) ![28 Upper Main Street - Photo 30](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f638142862r.jpg) ![28 Upper Main Street - Photo 31](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f4146259785r.jpg) ![28 Upper Main Street - Photo 32](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f732189889r.jpg) ![28 Upper Main Street - Photo 33](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f820642014r.jpg) ![28 Upper Main Street - Photo 34](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f1016786420r.jpg) ![28 Upper Main Street - Photo 35](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f2780496460r.jpg) ![28 Upper Main Street - Photo 36](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f2159186827r.jpg) ![28 Upper Main Street - Photo 37](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f345767825r.jpg) ![28 Upper Main Street - Photo 38](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f1539976214r.jpg) ![28 Upper Main Street - Photo 39](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f1260979970r.jpg) ![28 Upper Main Street - Photo 40](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f2192738144r.jpg) ![28 Upper Main Street - Photo 41](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f772833911r.jpg) ![28 Upper Main Street - Photo 42](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f474246559r.jpg) ![28 Upper Main Street - Photo 43](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f3500363623r.jpg) ![28 Upper Main Street - Photo 44](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f1377809995r.jpg) ![28 Upper Main Street - Photo 45](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f458887227r.jpg) ![28 Upper Main Street - Photo 46](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f3410481562r.jpg) ![28 Upper Main Street - Photo 47](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f343730035r.jpg) ![28 Upper Main Street - Photo 48](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f922053098r.jpg) ![28 Upper Main Street - Photo 49](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f3960364237r.jpg) ![28 Upper Main Street - Photo 50](http://lh.rdcpix.com/6b635c45e4c60a49de336d6d96def730l-f2327760546r.jpg) --- **MLS#:** 1040279 | **Updated:** 2026-08-28 **Source:** listhub *Copyright © 2026 OneKey MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/28-upper-main-street-callicoon-ny-12723-1040279) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/28-upper-main-street-callicoon-ny-12723-1040279#listing", "url": "https://www.propertysimple.ai/listing/28-upper-main-street-callicoon-ny-12723-1040279", "name": "28 Upper Main Street, Callicoon, NY 12723", "description": "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. 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