Recently Listed Open House 8/28 4pm - 6pm
256 Cottage Street
Middletown, NY, 10940 $ 299,900
Bedrooms3 Baths1.0 Sq 860 Monthly Estimate*
$ 1,894
for $299,900 with 3 bedrooms and 1 full bath. This 860 square foot home was built in 1924 on a lot size of 0.2755.
The first thing you will do here is walk out into that lawn and start deciding where everything goes, the garden along the sunny side, the fire pit set well back, the patch under the old shade tree that stays empty because that is the coolest spot on the property and you are going to want it for yourself. The lot is 0.28 acres, flat and open, and every bit of it comes with the keys. Not many city addresses have that much grass around them. The covered porch is what will slow you down before you reach the door. It stretches deep across the front, set on stone piers laid by hand in 1924, looking out over the whole yard. June evenings belong out there. So does October, with a blanket and a hot drink while the tree lets go of everything at once. It is going to be the first thing you describe when people ask about the place. Inside, the rooms are bright and freshly painted, and the windows do most of the work, pulling light through the front of the house all afternoon. One bedroom is right on the main floor, which is the kind of flexibility you never appreciate until you have it, a desk and a door you can shut on a Monday, a spare room the weekend somebody stays over. Two more are tucked upstairs under the roofline with windows framing rooftops and treetops, quiet enough that a long day actually ends when you climb up there. The basement below runs nearly 23 feet, clean, bright and completely unfinished, which is the good kind of unfinished. Right now it holds the bikes and the holiday bins. In a few years it becomes the workshop, the studio, the practice room, whatever version of yourself you have not gotten around to yet. The space is already bought and paid for. You just grow into it. The upkeep is easy to live with. Natural gas heat takes care of February, and municipal water and sewer mean nothing buried in the yard you ever have to think about. The cabinets were repainted this year and the interior is done, so you move in and simply live in it. Then the city fills in the rest of the year. From June through October the market sets up Saturdays, 8 to 1, at Erie Way Park on Union Street, a 5 minute drive away. Dinner at Oak & Reed on North Street turns into a habit rather than a plan once it is that easy to get to. Thrall Library on Depot Street lends museum passes, so Storm King, DIA Beacon and Bethel Woods cost you a library card and a tank of gas. Outside is just as close. Watts Memorial Park is a little over a mile up Wisner Avenue, and Fancher-Davidge has the pool, the walking trails and a disc golf course on the west side of town. Sunday nights in season the Speedway races on Wisner, near enough that you can decide to go at 6 p.m. and still make it. When you want out of town entirely, the Middletown station on the NJ Transit Port Jervis Line carries you to Hoboken and Penn Station, Route 17 and I-84 are minutes away, and Manhattan sits 70 miles east. A century is a long time for one house to be looked after by the same owners, and it shows the moment you step inside. Nothing here was let go and patched back together later. It was simply kept, one winter at a time, which is why the walls run true and the stonework still sits level. That care is the part you cannot renovate in afterward. It is already here, in the open ground, in the straight lines, in a hundred years of somebody paying attention. All this place needs now is a new name on the deed. Now it is your turn on that porch.
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Open House
8/28/2026 4:00 PM - 6:00 PM
8/30/2026 11:00 AM - 1:00 PM
256 Cottage Street Middletown, NY
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm
FeaturesInteriorInterior Amenities First Floor Bedroom First Floor Full Bath Eat-in Kitchen
Basement Unfinished
Flooring Hardwood Vinyl
Basement Features Unfinished
Basement (Y/N) Y
Fireplace Y/N N
Half Baths 0
Total Bedrooms 3
Total Baths 1
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GeneralSewer Public Sewer
Heating Baseboard Natural Gas
Cooling Wall/Window Unit(s)
Utilities Electricity Connected
Appliances Range Refrigerator
Patio/Porch Features Covered Porch
Architectural Style Cape Cod
Construction Materials Wood Siding
Year Built 1924
Property Subtype Single Family Residence
Tax Year 2025
Parcel Number 330900-009-000-0003-001.000-0000
County Orange County
Property Type Residential
HOA N
Garage Y/N N
Total Rooms 7
Full Baths 1
High School Middletown High School
City Middletown
Senior Community Y/N N
High School District Middletown
Carport Y/N N
Elementary School Presidential Park Elementary
Property Attached Y/N N
Tax Annual Amount 4562.76
Middle/Junior High School Middletown Twin Towers Middle Sch
Building Area Units Square Feet
Standard Status Active
Middle/Junior School District Middletown
Elementary School District Middletown
Tax Assessed Value 16300
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ExteriorParking Features On Street On Street
Water Source Public
Spa N
Waterfront Y/N N
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* Excluded FeaturesList ByBrian J CaplickiListing Agent
Kw Hudson Valley UnitedBroker
Affordability Calculator
- Monthly Principal & Interest
- $1,894
- Monthly Property Taxes
- $380
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Middletown, NY
Average List Price $473,284
Percent of Sale Price 58%
About Middletown, NY 3,497 Population
-14% Since 2002
$ 43,415 Median Income
52.6 Median Age
21% Households with Children
Trends Information provided by ATTOM Data Solutions.
4892405 Elementary School
4100242 Middle School
Middletown High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 8/26/2026 | $299,900 | | Listed Price |