28 Upper Main Street, Callicoon, NY 12723
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Property image
FOR SALE
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$749,999

  • 7 Beds
  • 3 Baths
  • 4,900 sqft

28 Upper Main Street, Callicoon, NY 12723

Est. Mortgage $5,157/mo*
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Home Highlights

Single-Family Home
Built in 1885
$153/sqft

Local Information

  • Map ViewExplore the area around 28 Upper Main Street.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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
Last check for updates: about 7 hours ago
Listing by: BERKSHIRE HATHAWAY, (516) 741-3070
Gregory A. Berkowitz, (516) 526-7775
BERKSHIRE HATHAWAY, (631) 642-6212
Lillian Rose Worthy, (347) 407-2628
Source: OneKey® MLS as distributed by MLS GRID, MLS#1040279
Also Listed on OneKey® MLS as distributed by MLS GRID.

Home Details for 28 Upper Main Street

Interior Features

Interior Details
Basement: UnfinishedNumber of Rooms: 8
Beds & Baths
Number of Bedrooms: 7Number of Bathrooms: 4Number of Bathrooms (full): 2Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 4900 Square Feet
Appliances & Utilities
Utilities: Electricity ConnectedAppliances: Other
Heating & Cooling
Heating: Electric,Hot Water,Propane,OtherHas CoolingAir Conditioning: Multi UnitsHas HeatingHeating Fuel: Electric
Fireplace & Spa
No Spa
Gas & Electric
Has Electric on Property

Exterior Features

Exterior Home Features
No Private Pool
Parking & Garage
No CarportNo GarageParking: Private
Water & Sewer
Sewer: Public Sewer
Farm & Range
Not Allowed to Raise Horses

Days on Market

Cumulative Days on Market: 1Days on Market: 29

Property Information

Year Built
Year Built: 1885
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Other
Building
Construction Materials: ClapboardNot Attached Property
Property Information
Parcel Number: 260001400005024000

Price & Status

Price
List Price: $749,999Price Per Sqft: $153

Active Status

MLS Status: Active

Media

Location

Direction & Address
City: Callicoon
School Information
Elementary School: Sullivan West ElementaryJr High / Middle School: SULLIVAN WEST HIGH SCHOOL AT LAKE HUNTINGTONHigh School: Sullivan West High School At Lake HuntingtonHigh School District: Sullivan West

Agent Information

Listing Agent
Listing ID: 1040279

Building

Building Area
Building Area: 8764 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 7841 sqft

Listing Info

Special Conditions: None

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: 1040279Attic: NoneAttribution Contact: 516-741-3070Showing Requirements: 24 Hour Notice, Appointment Only, Call Listing Agent

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
$715K
Since last month
Decreased$13K (-1.8%)
Since last year
Increased$300K (+72.5%)
Since last sale
Increased$433K (+153.4%)
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 +46% in the last 10 years
MonthEstimated value
2026
September 2026$715K
August 2026$728K
2025
2024
2023

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
12 Highview Avenue, Callicoon, NY
0.11
Single-Family Home
$540,000
07/10/26
5
2
2,612
21 Mitchell Avenue, Callicoon, NY
0.10
Single-Family Home
$389,000
03/23/26
3
2
1,292
4260 State Route 17B, Callicoon, NY
0.09
Single-Family Home
$450,000
05/29/26
3
2
2,300
2585 River Rd, Damascus, PA
0.35
Single-Family Home
$615,000
04/10/26
5
3.5
2,412
2517 River Rd, Damascus, PA
0.57
Single-Family Home
$495,000
08/07/26
2
1.5
1,400
9478 State Route 97, Callicoon, NY
0.91
Single-Family Home
$385,000
06/25/26
4
2
2,256
409 Kautz Road, Callicoon, NY
0.95
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
0.05
$392,300
3
2.5
3,744
Off Market
4260 State Route 17B, Callicoon, NY 12723
0.09
$450,000
3
2
2,300
Recently Sold
21 Mitchell Avenue, Callicoon, NY 12723
0.10
$389,000
3
2
1,292
Recently Sold
10 High Street, Callicoon, NY 12723
0.10
$243,900
4
2
1,504
Off Market
12 Highview Avenue, Callicoon, NY 12723
0.11
$540,000
5
2
2,612
Recently Sold
48 Upper Main Street, Callicoon, NY 12723
0.11
$759,000
3
1.5
1,536
For Sale
9 River Road, Callicoon, NY 12723
0.13
$914,800
8
8
5,796
Off Market
11 Highview Avenue, Callicoon, NY 12723
0.14
$379,000
5
1.5
2,536
For Sale
12 Mitchell Road, Callicoon, NY 12723
0.14
$312,800
7
4
-
Off Market
9286 State Route 97, Callicoon, NY 12723
0.15
$346,500
5
3
3,290
Off Market
23 River Road, Callicoon, NY 12723
0.16
$515,000
2
2
1,496
Off Market

Price and Tax history

DateEventPrice
Aug 18, 2026
Source: OneKey® MLS as distributed by MLS GRID #1040279
Listed For Sale
$749,999
Mar 18, 2024
Source: GBMLS #323975
ListingRemoved
Dec 13, 2023
Source: GBMLS #323975
Listed For Sale
$499,000
Aug 15, 2018
Source: N/A
Sold
$282,000
Jul 10, 1996
Source: N/A
Sold
$65,000

LGBTQ Local Legal Protections

Gregory A. Berkowitz, BERKSHIRE HATHAWAY, (516) 741-3070
Agent Phone: (516) 526-7775
Based on information submitted to the MLS GRID as of 2026-09-16 09:43:24 PDT 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. Some IDX listings have been excluded from this website. Click here for more information

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Frequently asked questions about 28 Upper Main Street

  • What is the estimated monthly payment for 28 Upper Main Street?
    Based on a $749,999 list price with 20% down at today's rates, the estimated monthly payment for 28 Upper Main Street in Callicoon, NY is approximately $5,225 (about $4,044 principal & interest, $1,106 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 28 Upper Main Street?
    The closest schools to 28 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 28 Upper Main Street estimated to be worth?
    Trulia's estimated value for 28 Upper Main Street in Callicoon, NY is $714,700.
  • Does 28 Upper Main Street have air conditioning?
    Yes, 28 Upper Main Street in Callicoon, NY has air conditioning.
  • How big is the lot at 28 Upper Main Street?
    The lot at 28 Upper Main Street in Callicoon, NY is about 0.18 acres (7,841 sq ft).
28 Upper Main Street, Callicoon, NY 12723 is a 7 bedroom, 4 bathroom, 4,900 sqft single-family home built in 1885. This property is currently available for sale and was listed by OneKey® MLS as distributed by MLS GRID on Aug 18, 2026. The MLS # for this home is MLS# 1040279.