55 Upper Main St
Callicoon, NY 12723
2 Beds
2 Baths
800 sqft
2 Beds
2 Baths
800 sqft
Local Information
- Map ViewExplore the area around 55 Upper Main St.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Description
Adorable & Quaint Handyman/woman's Special! Great opportunity to get a deal for year round or getaway in a quaint river town. Walk to dining, antiques, theatre. Special little place needs some TLC. Kitchen has been gutted so buyer can renovate to their liking. Yard for gardeners' delight. Rocking chair porch, picket fence. Two bedrooms on main level with enclosed rear porch AND finished attic for third bedroom as well as finished basement with workshop. Open floorplan, hardwood floors, and shed. Motivated seller seeks offers. Needs some TLC but well worth it!! Sweet!<br/><br/>Brokered And Advertised By: MALEK PROPERTIES<br/>Listing Agent: CAROL A MALEK
55 Upper Main St, Callicoon, NY 12723 is a 2 bedroom, 2 bathroom, 800 sqft single-family home built in 1940. It last sold for $140,000 on Oct 5, 2021. It is currently off market. The Trulia Estimate is $247,700, with a rent estimate of $1,698/month.
Home Highlights
Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago
Home Details for 55 Upper Main St
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Heating & Cooling Heating: Other, ElectricHeating Fuel: Other |
Levels, Entrance, & Accessibility Stories: 1.5 |
Interior Details Number of Rooms: 5Types of Rooms: Recreation Room |
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Year Built Year Built: 1940Year Updated: 2011 |
Property Type / Style Property Type: Single Family HomeArchitecture: Old Style |
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Exterior Home Features Exterior: Wood |
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Units in Building: 1 |
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Lot Area: 5662 sqft |
Price History for 55 Upper Main St
| Date | Price | Event | Source |
|---|---|---|---|
| 09/13/2025 | $375,000 | ListingRemoved | OneKey® MLS as distributed by MLS GRID #842191 |
| 08/25/2025 | $375,000 | PriceChange | OneKey® MLS as distributed by MLS GRID #842191 |
| 08/06/2025 | $385,000 | PriceChange | OneKey® MLS as distributed by MLS GRID #842191 |
| 05/27/2025 | $398,000 | PriceChange | OneKey® MLS as distributed by MLS GRID #842191 |
| 04/04/2025 | $419,000 | Listed For Sale | OneKey® MLS as distributed by MLS GRID #842191 |
| 10/05/2021 | $140,000 | Sold | N/A |
| 06/02/2010 | $65,000 | Sold | N/A |
| 02/11/2010 | $79,900 | ListingRemoved | Agent Provided |
| 01/29/2010 | $79,900 | PriceChange | Agent Provided |
| 07/08/2009 | $99,900 | PriceChange | Agent Provided |
| 06/27/2009 | $124,000 | Listed For Sale | Agent Provided |
| 02/18/2009 | $124,000 | ListingRemoved | Agent Provided |
| 09/14/2008 | $124,000 | Listed For Sale | Agent Provided |
Market trends in Callicoon
Last updated May 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
19
2MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | |
| Assessment | $174,082 |
Home facts updated by county records
Comparable Sales for 55 Upper Main St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.23 | Single-Family Home | $389,000 | 03/23/26 | 3 | 2 | 1,292 | |
0.09 | Single-Family Home | $520,000 | 09/04/25 | 2 | 2 | 1,496 | |
0.21 | Single-Family Home | $450,000 | 05/29/26 | 3 | 2 | 2,300 | |
0.31 | Single-Family Home | $615,000 | 04/13/26 | 5 | 1 | 1,680 | |
0.35 | Single-Family Home | $615,000 | 04/10/26 | 5 | 3.5 | 2,412 | |
0.80 | Single-Family Home | $385,000 | 06/25/26 | 4 | 2 | 2,256 | |
0.99 | Single-Family Home | $400,000 | 05/15/26 | 4 | 2 | 2,157 | |
1.30 | Single-Family Home | $399,000 | 06/15/26 | 4 | 2 | 1,674 | |
1.75 | Single-Family Home | $325,000 | 12/19/25 | 4 | 2 | 1,740 | |
1.85 | Single-Family Home | $430,000 | 11/20/25 | 3 | 1.5 | 1,700 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
FOR SALE1.14 ACRESListing by: Keller Williams Upstate NY Pro, Active
OFF MARKETCatskill Sales Associates Inc
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FOR SALEListing by: Matthew J Freda Real Estate
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FOR SALE1.16 ACRESMatthew J. Freda Real Estate, Inc.
Assigned Schools
These are the assigned schools for 55 Upper Main St.
- Sullivan West High School At Lake Huntington
- 7-12
- Public
- 492 Students
5/10GreatSchools RatingParent Rating AverageMy experience with this school district has been awful. As a parent the administration in both the elementary and high school has been nothing short of ineffective. Bullying and racism are huge issues in this district and both continue because they are not dealt with. Parents receive mostly lip service that they are doing everything possible to handle the situation, when in reality nothing is being done. The number of staff that genuinely care for, support, advocate, and try to do all they can for your child is minimal. Most serious incidents involve hiding the facts so that the school’s reputation and funding is not jeopardized. I would never recommend this district to anyone. The behaviors of both administration, many faculty, and other students can cause your own child mental, physical, and emotional trauma.Parent Review4y ago - Sullivan West Elementary School
- PK-6
- Public
- 553 Students
5/10GreatSchools RatingParent Rating AverageMy son has been going to Sullivan West for a year. He loves and I love it. I enjoyed volunteering in his class all year and his teacher was awesome. I am so excited to see what first grade brings!Parent Review9y ago 
Check out schools near 55 Upper Main St.
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.
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Apartments for Rent
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Homes for sale near 55 Upper Main St
- 1.14 ACRESListing by: Keller Williams Upstate NY Pro, Active
FOR SALE BY OWNER- Listing by: Matthew J Freda Real Estate
- 1.16 ACRESMatthew J. Freda Real Estate, Inc.
6.85 ACRESListing by: Country House Realty, Inc., Active
3.71 ACRESMatthew J. Freda Real Estate, Inc.
8.02 ACRESListing by: R J Katz Realty
10.05 ACRESListing by: Hart & Johnson Realty
NEW CONSTRUCTION5.1 ACRESListing by: Land and Water Realty LLC
2.5 ACRESMatthew J. Freda Real Estate, Inc.
See more homes for sale inCallicoon
Off Market Homes Near 55 Upper Main St
SOLDJUN 29, 2026Callicoon Real Estate LLC
SOLDAPR 23, 2026Matthew J Freda Real Estate
SOLDFEB 23, 2026Keller Williams Hudson Valley
SOLDFEB 17, 2026- SOLDFEB 2, 2026
- See more homes for sale inCallicoon
