1 of 20

Want to see this home?

55 Upper Main Street

Callicoon, NY 12723

2 beds
1 bath
1,288 sqft
5,663 sqft lot
$325 per sqft
1940 build
– on site

Charming In-Town 1940s Cottage with Modern Updates & Endless Possibilities! Welcome to this beautifully updated 1940s cottage—a perfect blend of classic character and modern convenience, right in the heart of town. With 2 spacious bedrooms and a renovated full bathroom, this home offers move-in ready comfort and style. The generous kitchen boasts modern appliances and ample space for cooking and gathering, while the light-filled insulated sunroom is your new favorite spot for morning coffee or an afternoon book—complete with doors that lead directly to the backyard. Upstairs, you'll find two versatile bonus rooms just waiting for your imagination—ideal for a home office, guest space, yoga room, or creative studio. The covered front porch sets the scene for relaxing evenings with a view of the neighborhood buzz. Downstairs, the full stacked stone basement offers a blank canvas with walk-out access—dream up a wine tasting room, cigar lounge, home theater, or hobby cave. Under the sunroom, you’ll find a flexible carport or patio area for entertaining or storage. A side driveway leads to a garage primed for transformation into a home gym, artist’s workshop, or remote office. And yes, there’s even an outdoor shower for those who enjoy rinsing off under the open sky! Located just a short stroll from the river, this home is within easy walking distance to local shops, dining, live entertainment, and the beloved town movie theater—offering the ideal balance of small-town charm and modern lifestyle.

Listing courtesy of ONEKEY / Keller Williams Hudson Valley

Last checked: Checking… • Last updated Apr 5, 2025 •

MLS# 842191 —

The Building

Year Built:

1940
Basement:

true
Architectural Style:

Cottage, Farmhouse
Construction Materials:

Frame, Wood Siding
Year Built Effective:

2022
Building Area Units:

Square Feet
Building Area Total:

2088
Building Area Source:

Public Records
Laundry Features:

Electric Dryer Hookup, In Hall, Inside, Washer Hookup
Attic:

Finished,Full,Stairs,Walkup

Interior

Levels:

Two
Living Area:

1288
Total Rooms:

8
Interior Features:

First Floor Bedroom, First Floor Full Bath, High Speed Internet, Open Floorplan, Pantry, Washer/Dryer Hookup
Fireplace:

false
Living Area Source:

Public Records
# of Kitchens:

1

Financial & Terms

Lease Considered:

false

The Property

Lot Size Acres:

0.13
Parcel Number:

2600-014-0-0005-015-000
Property Type:

Residential
Property Subtype:

Single Family Residence
Lot Size SqFt:

5,663 Sqft
Property Attached:

false
Property Condition:

Updated/Remodeled
Waterfront:

false
Water Access:

No

Listing Agent

Contact info:

Taxes

Tax Year:

2024
Tax Source:

Municipality
Tax Annual Amount:

3527.59
Tax Lot:

15

Beds

Total Bedrooms:

2

Baths

Full Baths:

1
Total Baths:

1

The Listing

Special Listing Conditions:

None

Heating & Cooling

Heating:

Baseboard, Electric, Forced Air
Cooling:

None

Utilities

Sewer:

Public Sewer
Utilities:

Cable Connected, Electricity Connected, Sewer Connected, Water Connected
Water Source:

Public
Electric Company:

Nyseg

Appliances

Appliances:

Dryer, Electric Oven, Electric Range, Electric Water Heater, Refrigerator, Washer

Schools

High School:

Sullivan West High School
Elementary School:

Sullivan West Elementary
High School District:

Sullivan West
Middle School:

SULLIVAN WEST HIGH SCHOOL AT LAKE HUNTINGTON

The Community

Association:

false
Senior Community:

false
Pool Private:

false
Spa:

false

Parking

Parking Features:

Carport, Driveway, Garage
Garage:

true
Garage Spaces:

1
Carport:

true
Carport Spaces:

1

Monthly cost estimate

Asking price

$419,000

Expense	Monthly cost
Mortgage	$2,243
Taxes	$293
Insurance	$115
Utilities	$424 See report
Total	$3,075/mo.^*
	^*This is an estimate

Explore the Area

My Commute

From

Walk Score®

Provided by WalkScore® Inc.

Bike Score®

Provided by WalkScore® Inc.

Air Pollution Index

Provided by ClearlyEnergy

Sale history

Date	Event	Source	Price	% Change
4/4/25 Apr 4, 2025	Price Changed	ONEKEY	$419,000	-3.7%
4/4/25 Apr 4, 2025	Listed / Active	ONEKEY	$435,000

Want a closer look?

Go see 55 Upper Main Street

Or Call Toll Free 1-800-241-3327

We guarantee that we’ll never spam you.

* indicates a required field

More homes

Newest listings in Callicoon, NY

Similar sold homes

This house located in Callicoon, NY 12723 is currently for sale for $419,000. 55 Upper Main Street is a 1,288 square foot house with 2 beds and 1 bath that has been on Estately for 7 days.

Listing Courtesy of: ONEKEY and Keller Williams Hudson Valley.

IDX information is provided exclusively for consumers’ personal non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by the MLS.

Based on information submitted to the MLS GRID. 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.