BEDS3
BATHS1 full 1 partial
SQUARE FEET1,536
MLS#925634
STATUSActive
PROPERTY TYPEResidential - Single Family
SCHOOLSullivan West
Property Description
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 remain today. Now reimagined by artists, the building bridges eras with a rare blend of authenticity and modern livability. A bright three-bedroom, two-bath residence offers comfort and warmth with custom cabinetry, solid wood floors, and rich natural light. Beyond, the structure unfolds into vast and inspiring spaces: a 60-by-34-foot gymnasium with a 20-foot ceiling and stage; a luminous upper-floor dance studio spanning nearly sixty feet; art studios inspired by gigantic windows bringing in nature and sunlight, open workrooms, and a full stacked stone-foundation basement with walk-in access. At roughly 13,000 square feet on over an acre, the property invites both vision and versatility. Zoned for mixed use, it can evolve into a gallery and performance venue, a live-work compound, a wellness retreat, or a community hub. Every beam and window suggests possibility-every echo in the old gym reminds you that this building was made for voices, for movement, for gathering. Surrounded by ornamental trees and perennial gardens, and just a short stroll from Callicoon's beloved cafes, the farmers' market, and the Delaware River, 48 Upper Main offers both privacy and presence. It is that rare piece of architecture that feels both anchored in history and untethered in potential. Updated infrastructure includes a new metal roof and a new boiler (with a copper manifold that will inspire envy). A place where authenticity reigns, light abounds, and inspiration seems to gather naturally within the walls. 48 Upper Main Street isn't just a building-it's a living story waiting for its next author. Offering includes two tax parcels .89 acres and .25
Property Features
Property Type: Residential - Single Family
Basement: Bilco Door(s), Full, Storage Space, Unfinished
Basement: Yes
Cooling: Ductless, Electric, Multi Units
Heating: Electric, Forced Air, Heat Pump, Hot Water, Oil, Propan
Home Style: Other
Lot Size: 1.14 Acres
Taxes: $14,852
Year Built: 1908
Amenities
First Floor Bedroom
First Floor Full Bath
Breakfast Bar
Built-in Features
Cathedral Ceiling(s)
Entrance Foyer
High Ceilings
High Speed Internet
Natural Woodwork
Original Details
Tile Counters
Washer/Dryer Hookup
Feature Descriptions
Appliances: Dishwasher, Electric Oven, Refrigerator
Attic: Walkup
Building Area Total: 13669
Days on Site: 174
Exterior: Clapboard, Frame, Stone
Flooring: Wood
Lot Features: Near Shops, Part Wooded, See Remarks, Sloped, Stone/Brick Wall, Views, Wooded
Number Of Kitchens: 1
On Market Date: 2025-10-17
Parcel Number: 2600-014-0-0001-001-000
Parking Features: Driveway, Off Street, Parking Lot, Shared Driveway
Rental Term: Monthly
Rooms Total: 7
Sewer: Public Sewer
Utilities: Cable Connected, Electricity Connected, Sewer Connected, Water Connected
Water: Public
Window Features: Floor to Ceiling Windows, Oversized Windows, Wood Frames
Wooded: Yes
Local Schools
High School: Sullivan West High School At Lake Huntington
Middle School: SULLIVAN WEST HIGH SCHOOL AT LAKE HUNTINGTON
Elementary School: Sullivan West Elementary
School District: Sullivan West
Listed By / Shown By
Listing By
Agency Name: Keller Williams Upstate NYProp
Agency Phone: 585-877-8283
Shown By
Agency Title: RealtyMark
Agency Phone: 888-240-0600
Estimate Your Payment
Estimated Payment
$ 3,248.94 per month $1,778.23 Principal & Interest $1,237.67 Property Tax $233.04 Homeowner's InsuranceChange Payment Information
48 Upper Main Street | MLS# 925634
This single family home located at 48 Upper Main Street, Callicoon, NY 12723 is currently listed for sale with an asking price of $799,000. This property was built in 1908 and has 3 bedrooms and 1 full and 1 partial baths with 1536 sq. ft. Upper Main Street is located within the Sullivan West school district. Search Callicoon real estate on www.realtymark.net today.