48 Upper Main Street, Callicoon, NY 12723
Property image
Property image
FOR SALE
1.14 ACRES

$759,000

Original price: $799,000
  • 3 Beds
  • 1.5 Baths
  • 1,536 sqft (on 1.14 acres)

48 Upper Main Street, Callicoon, NY 12723

Est. Mortgage $5,222/mo*
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Home Highlights

Single-Family Home
Built in 1908
1.14 acre lot
$494/sqft

Local Information

  • Map ViewExplore the area around 48 Upper Main Street.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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
Last check for updates: about 15 hours ago
Listing by: Keller Williams Upstate NY Pro, (607) 431-2540
Dara Barr, (917) 523-1782
Source: HVCRMLS, MLS#20255409
Also Listed on OneKey® MLS as distributed by MLS GRID, HVCRMLS, OneKey® MLS as distributed by MLS GRID.

Home Details for 48 Upper Main Street

Active Status

MLS Status: Active

Interior Features

Interior Details
Basement: Full,Interior Entry,Unfinished,Walk-Out Access
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1536 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Electricity Connected, Sewer Connected, Water ConnectedAppliances: Refrigerator, RangeRefrigerator
Heating & Cooling
Heating: Ductless,Heat Pump,Hot Water,Oil,ZonedHas CoolingAir Conditioning: Heat PumpHas HeatingHeating Fuel: Ductless
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Flooring: Hardwood, Wood
Levels, Entrance, & Accessibility
Floors: Hardwood, Wood

Exterior Features

Exterior Home Features
Roof: MetalFencing: PartialOther Structures: Outbuilding, Shed(s), Storage, See RemarksFoundation: Stone
Parking & Garage
No Garage
Frontage
Road Frontage: County RoadRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 9056 Square Feet

Days on Market

Days on Market: 166

Property Information

Year Built
Year Built: 1908
Property Type / Style
Property Type: ResidentialProperty Subtype: Mixed UseStructure Type: Mixed UseArchitecture: Other
Building
Construction Materials: Clapboard, Frame, Stone, Wood SidingNot a New Construction
Property Information
Included in Sale: stove in apt, fridge in aptParcel Number: 14.46.1 + 14.11

Price & Status

Price
List Price: $759,000Price Per Sqft: $494

Location

Direction & Address
City: Callicoon
School Information
High School District: Sullivan West Central Schools

Agent Information

Listing Agent
Listing ID: 20255409

Building

Building Area
Building Area: 1536 Square Feet

Lot Information

Lot Area: 1.14 Acres

Offer

Listing Terms: Cash, Owner May Carry, Submit

Miscellaneous

BasementMls Number: 20255409Above Grade Unfinished Area: 9056

Around this home

What Locals Say about Callicoon

At least 6 Trulia users voted on each feature.

  • 100 % Say car is needed

  • 86 % Say it's dog friendly

  • 83 % Say there's wildlife

  • 71 % Say neighbors are friendly

  • 71 % Say it's walkable to grocery stores

  • 67 % Say streets are well-lit

  • 64 % Say there are community events

  • 62 % Say yards are well-kept

  • 60 % Say parking is easy

  • 60 % Say kids play outside

  • 56 % Say it's walkable to restaurants

  • 56 % Say people would walk alone at night

  • 55 % Say there are sidewalks

  • 50 % Say there's holiday spirit

  • 38 % Say they plan to stay for at least 5 years

  • 25 % Say it's quiet

Sourced by Trulia users. Learn more about our methodology.
  • Fceisenberg
    "The first 5 miles in the morning— and last at night — wind all no a curvy country road next to a scenic creek. Great way to start and end the day."
    0
    Flag

Market trends in Callicoon

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
18
2MoM

Home Value

Trulia Estimate
$730K
Since last month
Increased$13K (+1.9%)
Since last year
Increased$25K (+3.5%)
Since last sale
Increased$259K (+55.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +197% in the last 10 years
MonthEstimated value
2026
September 2026$730K
August 2026$717K
July 2026$725K
June 2026$768K
May 2026$769K
April 2026$770K
March 2026$793K
February 2026$792K
January 2026$790K
2025
2024
2023
2022

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
4260 State Route 17B, Callicoon, NY
0.19
Single-Family Home
$450,000
05/29/26
3
2
2,300
21 Mitchell Avenue, Callicoon, NY
0.21
Single-Family Home
$389,000
03/23/26
3
2
1,292
2517 River Rd, Damascus, PA
0.65
Single-Family Home
$495,000
08/07/26
2
1.5
1,400
2585 River Rd, Damascus, PA
0.38
Single-Family Home
$615,000
04/10/26
5
3.5
2,412
12 Highview Avenue, Callicoon, NY
0.22
Single-Family Home
$540,000
07/10/26
5
2
2,612
9478 State Route 97, Callicoon, NY
0.80
Single-Family Home
$385,000
06/25/26
4
2
2,256
9568 State Route 97, Callicoon, NY
1.03
Single-Family Home
$266,000
08/05/26
2
1
1,159
409 Kautz Road, Callicoon, NY
0.94
Single-Family Home
$540,000
07/27/26
2
2.5
1,314

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
34 Upper Main Street, Callicoon, NY 12723
0.06
$414,800
3
2.5
3,744
Off Market
10 High Street, Callicoon, NY 12723
0.06
$245,100
4
2
1,504
Off Market
28 Upper Main Street, Callicoon, NY 12723
0.11
$749,999
7
3
4,900
For Sale
23 River Road, Callicoon, NY 12723
0.13
$513,000
2
2
1,496
Off Market
9 River Road, Callicoon, NY 12723
0.14
$924,900
8
8
5,796
Off Market
4260 State Route 17B, Callicoon, NY 12723
0.19
$450,000
3
2
2,300
Recently Sold
21 Mitchell Avenue, Callicoon, NY 12723
0.21
$389,000
3
2
1,292
Recently Sold
12 Highview Avenue, Callicoon, NY 12723
0.22
$540,000
5
2
2,612
Recently Sold
12 Mitchell Road, Callicoon, NY 12723
0.25
$343,200
7
4
-
Off Market
9286 State Route 97, Callicoon, NY 12723
0.25
$355,100
5
3
3,290
Off Market
11 Highview Avenue, Callicoon, NY 12723
0.25
$379,000
5
1.5
2,536
For Sale

Price and Tax history

DateEventPrice
Jul 17, 2026
Source: OneKey® MLS as distributed by MLS GRID #925634
PriceChange
$759,000
Price decreased by 5%
Apr 5, 2026
Source: HVCRMLS #20255409
Listed For Sale
$799,000
Dec 15, 2025
Source: HVCRMLS #20255409
ListingRemoved
$830,000
Oct 17, 2025
Source: OneKey® MLS as distributed by MLS GRID #925634
Listed For Sale
$830,000
Apr 27, 2018
Source: OneKey® MLS as distributed by MLS GRID #H4218785
Sold
$471,000

LGBTQ Local Legal Protections

Dara Barr, Keller Williams Upstate NY Pro, (607) 431-2540
Agent Phone: (917) 523-1782
IDX information © 2026 by the Hudson Valley Catskill Region MLS. All Rights Reserved. The data relating to real estate on this website comes in part from the IDX of the Hudson Valley Catskill Region MLS.
Information is deemed reliable but is not guaranteed accurate by 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.

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Frequently asked questions about 48 Upper Main Street

  • What is the estimated monthly payment for 48 Upper Main Street?
    Based on a $759,000 list price with 20% down at today's rates, the estimated monthly payment for 48 Upper Main Street in Callicoon, NY is approximately $5,286 (about $4,091 principal & interest, $1,120 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Callicoon?
    Residents describe Callicoon, NY as dog-friendly, neighborly, and walkable to grocery stores. See homes for sale in Callicoon, NY.
  • What are the closest schools to 48 Upper Main Street?
    The closest schools to 48 Upper Main Street in Callicoon, NY are Sullivan West Elementary School (Pre-K, rated 4/10), Sullivan West High School At Lake Huntington (Middle, rated 6/10).
  • What is 48 Upper Main Street estimated to be worth?
    Trulia's estimated value for 48 Upper Main Street in Callicoon, NY is $730,300.
  • Does 48 Upper Main Street have air conditioning?
    Yes, 48 Upper Main Street in Callicoon, NY has air conditioning.
  • How big is the lot at 48 Upper Main Street?
    The lot at 48 Upper Main Street in Callicoon, NY is about 1.1 acres.
48 Upper Main Street, Callicoon, NY 12723 is a 3 bedroom, 2 bathroom, 1,536 sqft single-family home built in 1908. This property is currently available for sale and was listed by HVCRMLS on Apr 5, 2026. The MLS # for this home is MLS# 20255409.