48 Upper Main St

Callicoon, NY 12723

$799,000
Price
3
Beds
1,536 Sq. Ft.
$520 / Sq. Ft.
1,536
Sq. Ft.
$520
per Sq. Ft.
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Back of property featuring a wooded view
Aerial view of a heavily wooded area
Aerial view of property and surrounding area
Aerial overview of property's location featuring a heavily wooded area and a nearby body of water
View of yard with an outdoor fire pit
Stairway featuring hardwood / wood-style flooring and an ornate ceiling
Stairs featuring hardwood / wood-style floors, wooden walls, radiator heating unit, and wainscoting
Entryway featuring stairs, an ornate ceiling, hardwood / wood-style floors, and wooden walls
Detailed view of wood walls and wood finished floors
Sunroom featuring radiator heating unit
Detailed view of wooden walls
Unfurnished room featuring track lighting, dark wood-type flooring, and healthy amount of natural light
Garage featuring radiator and wood walls
Full bath with wooden walls, radiator heating unit, a freestanding tub, and dark wood-style flooring
Spare room with a barn door, an ornate ceiling, and radiator heating unit
Unfurnished living room featuring dark wood-style floors, wainscoting, plenty of natural light, and radiator
Office area with radiator heating unit, dark wood-style floors, plenty of natural light, and wainscoting
Dining space featuring dark wood-style flooring and a wall mounted air conditioner
Office area featuring wood finished floors and radiator
Empty room featuring radiator heating unit, wainscoting, and hardwood / wood-style flooring
Catwalk /hallway from main schoolhouse to gym
gym with vaulted ceiling, propane heater, stage
Miscellaneous room with a garage and concrete floors
former bathroom with stairs going to second attic/unfinished space
Unfinished attic featuring an upstairs landing
2nd former bathroom off of gym
Bathroom with tile walls, tile patterned flooring, vanity, a baseboard heating unit, and a wainscoted wall
Kitchen with white appliances, white cabinets, crown molding, pendant lighting, and glass insert cabinets
Living area with a baseboard radiator, ornamental molding, plenty of natural light, wood finished floors, and a wainscoted wall
Kitchen featuring white range with electric cooktop, white cabinets, open shelves, and tile counters
Kitchen with a wainscoted wall, ornamental molding, white cabinets, a kitchen bar, and hanging light fixtures
Dining room with ornamental molding, a baseboard radiator, a chandelier, wainscoting, and stone finish floors
Bedroom with ornamental molding, a baseboard radiator, dark wood-style floors, and a wainscoted wall
Bedroom featuring wood finished floors, a baseboard heating unit, crown molding, and wainscoting
Full bathroom featuring shower / bathtub combination with curtain, crown molding, wainscoting, and dark stone finish flooring
Doorway with wood finished floors, crown molding, and a wainscoted wall
Unfinished basement featuring a heating unit and stairs
View of front of house featuring french doors
View of exterior entry
View from above of property
Rear view of house featuring entry steps, a metal roof, and a chimney
View of yard with entry steps
View of home floor plan

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...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
  1. Listed by Dara Barr • Keller Williams Upstate NYProp
    P: (585)-877-8283 C: (917)-523-1782 darabarr@gmail.com

Property Details for 48 Upper Main Street

City/Township
Delaware
Architectural Style
Other
Waterfront
No
LISTING UPDATED: 04/07/2026 05:01 AM

Property Details for 48 Upper Main Street

StatusActive
MLS #925634
Days on Market65
Taxes$14,852 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeSingle Family
Year Built1908
Lot Size1.14 AC / 49,658 SF
CountySullivan County
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Location

Listing Courtesy of Keller Williams Upstate NYProp
Add your commute

Building Information for 48 Upper Main Street

Stories-Year Built1908Building Size-Lot Size1.14 AC / 49,658 SF

Payment Calculator

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$5,261 per month

30 year fixed, 6.46% Interest

Principal and Interest

$4,023

Property Taxes

$1,238

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 48 Upper Main Street

Summary
Location and General Information
  • Hamlet: Callicoon
  • Senior Community YN: No
  • Year Built Effective: 1990
  • Property Attached: No
  • Structure Type: false
  • Levels: One
  • State Or Province: NY
School Information
  • School District: Sullivan West
  • Elementary School District: Sullivan West
  • Elementary School: Sullivan West Elementary
  • Middle Or Junior School District: Sullivan West
  • Middle Or Junior School: SULLIVAN WEST HIGH SCHOOL AT LAKE HUNTINGTON
  • High School District: Sullivan West
  • High School: Sullivan West High School At Lake Huntington
Rental
Rental
  • Lease Considered: Yes
Unit Information
Unit Information
  • Building Units Total: 1
Taxes and HOA Information
Taxes and HOA Information
  • Parcel Number: 2600-014-0-0001-001-000
  • Tax Assessed Value: $397,800.00
  • Tax Source: Municipality
  • Tax Year: 2025.0
  • Association: No
Interior and Exterior Features
Interior Features
  • Amenities: 1st Floor Bedrm, Breakfast Bar, Built-in Features, Cathedral/Vaulted/High Ceiling, Entrance Foyer, First Floor Full Bath, Floor to Ceiling Windows, High Ceilings, High Speed Internet, Natural Woodwork, Original Details, Other, Oversized Windows, Public, Tile Counters, Washer/Dryer Hookup, Wood, Wood Frames
  • Interior Features: 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
  • Appliances: Dishwasher, Electric Oven, Refrigerator
  • Number Of Kitchens: 1.0
  • Total Rooms: 7
  • Basement: Bilco Door(s), Full, Storage Space, Unfinished
  • Attic Description: Walkup
  • Location Amenities: Other/See Remarks, 1st Fl Master Bedroom, Cathedral/Vaulted/High Ceiling, Entry Foyer, Foyer, High Ceilings, High Speed Internet, Original Details, WD Hookup, Brownstone, Scenic View, Oversized Windows
  • Window Features: Floor to Ceiling Windows, Oversized Windows, Wood Frames
  • Flooring: Wood
  • Living Area: 1,536.00
  • Foundation Details: Stone
  • Basement: Yes
Exterior Features
  • Exterior Property Features: Driveway, Off Street, Parking Lot, Shared Driveway, Floor to Ceiling Windows, Oversized Windows, Wood Frames, Near Shops, Part Wooded, See Remarks, Sloped, Stone/Brick Wall, Views, Wooded
  • Elevation Certificate: No
  • Construction Materials: Clapboard, Frame, Stone
  • Pool Private: No
Lot Information
  • Lot Features: Near Shops, Part Wooded, See Remarks, Sloped, Stone/Brick Wall, Views, Wooded
  • Additional Parcel: Yes
  • Site Features: Near Shops, Part Wooded, See Remarks, Sloped, Stone/Brick Wall, Views, Wooded
  • Building Area Units: Square Feet
Parking
  • Parking Features: Driveway, Off Street, Parking Lot, Shared Driveway
  • Garage: No
  • Carport: No
Utilities
  • Cooling: Ductless, Electric, Multi Units
  • Heating: Electric, Forced Air, Heat Pump, Hot Water, Oil, Propane
  • Heat Fuel Type: Electric, Forced Air, Heat Pump, Hot Water, Oil, Propane
  • Sewer: Public Sewer
  • Water Source: Public
  • Utilities: Cable Connected, Electricity Connected, Sewer Connected, Water Connected
Green Features
  • Green Features: Floor to Ceiling Windows, Oversized Windows, Wood Frames, Dishwasher, Electric Oven, Refrigerator, Electric, Forced Air, Heat Pump, Hot Water, Oil, Propane
Agent
Payment and Rate
  • Down Payment Resource: Yes

Property History for 48 Upper Main Street

DateEvent & SourcePriceAppreciation
Apr 5, 2026

Price Change

HVCR MLS #20255400

$799,000—
Apr 5, 2026

Price Change

HVCR MLS #20255409

$799,000—
Apr 5, 2026

Listed (Active)

HVCR MLS #20255409

$830,000—
Apr 5, 2026

Listed (Active)

HVCR MLS #20255400

$830,000—
Dec 15, 2025

Withdrawn

HVCR MLS #20255409

$830,000—
Dec 15, 2025

Withdrawn

HVCR MLS #20255400

$830,000—
Oct 30, 2025

Listed (Active)

HVCR MLS #20255409

$830,000—
Oct 30, 2025

Listed (Active)

HVCR MLS #20255400

$830,000—
Oct 17, 2025

Listed (Active)

ONEKEY #925634

$830,000—
Apr 27, 2018

Sold

ONEKEY #H4218785

$471,000—
Apr 12, 2018

Pending

ONEKEY #H4218785

—
Jul 21, 2017

Listed (Active)

ONEKEY #H4218785

$519,000—
DateEvent & SourcePrice
04/05/2026

Price Change

HVCR MLS #20255400

$799,000
04/05/2026

Price Change

HVCR MLS #20255409

$799,000
04/05/2026

Listed (Active)

HVCR MLS #20255409

$830,000
04/05/2026

Listed (Active)

HVCR MLS #20255400

$830,000
12/15/2025

Withdrawn

HVCR MLS #20255409

$830,000
12/15/2025

Withdrawn

HVCR MLS #20255400

$830,000
10/30/2025

Listed (Active)

HVCR MLS #20255409

$830,000
10/30/2025

Listed (Active)

HVCR MLS #20255400

$830,000
10/17/2025

Listed (Active)

ONEKEY #925634

$830,000
04/27/2018

Sold

ONEKEY #H4218785

$471,000
04/12/2018

Pending

ONEKEY #H4218785

—
07/21/2017

Listed (Active)

ONEKEY #H4218785

$519,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 48 Upper Main Street

Taxable ValueLand$28,300Additions$369,500Total$397,800
Tax Record2024$14,638 ($1,220 / month)
Home Facts
Total Finished SqFt17,296 SqFtAbove Grade Finished SqFt17,296 SqFtUnfinished Basement SqFt4,400 SqFtStories2Lot Size38,768 SqFtStyleMiscellaneous CommercialYear Built1908Year Renovated1990Zoning03 - MULTI-FACountySULLIVANAPN482600 14.-4-6.1

Schools near 48 Upper Main Street

This home is within Sullivan West Central School District.
Rating
School
Type
Grades
Distance
Sullivan West Elementary School
Public - PK to 6
Sullivan West High School At Lake Huntington
Public - 7 to 12
Rating
School
Distance
Sullivan West Elementary School
PublicPK to 6

Sullivan West High School At Lake Huntington
Public7 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 48 Upper Main Street, Callicoon, NY 12723

48 Upper Main Street is a single family home for sale in Callicoon, NY 12723. This property was listed for sale on October 17, 2025 by Keller Williams Upstate NYProp, it's currently listed at $799,000. It has been on the market for a total of 65 days and was last sold on April 27, 2018. This listing's school district is Sullivan West Central School District. Nearby schools include Sullivan West Elementary School and Sullivan West High School At Lake Huntington. 48 Upper Main Street is a 3-bed, 2-bath, 1,536 sqft single family home built in 1908.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Keller Williams Upstate NYProp

Based on information submitted to the MLS GRID as of 04/07/2026 05:01 AM. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed by MLS GRID. Use of the MLS GRID data may be subject to an end user license agreement prescribed by the applicable MLS of the Member Participant, if any, and as amended from time to time.