Middletown Homes with On Street Parking features

Welcome to Middletown, NY – a vibrant city nestled in the heart of Orange County, where community spirit meets educational excellence. Middletown is served by the Middletown City School District, renowned for its commitment to providing quality education and fostering a nurturing environment for students. With a diverse range of programs and extracurricular activities, the district ensures that every child has the opportunity to thrive academically and socially. Parents can take comfort in knowing that their children have access to dedicated educators and modern facilities, making Middletown a prime choice for families seeking a supportive educational landscape.

In addition to its stellar school district, Middletown offers a variety of charming homes that cater to different lifestyles and budgets. One of the appealing features of many properties in this area is the availability of on-street parking. This convenient amenity not only simplifies daily commutes but also enhances the overall neighborhood experience, allowing residents to enjoy the beauty of their surroundings without the hassle of parking restrictions.

Whether you are a first-time homebuyer or looking to relocate, Middletown's welcoming community and strong educational foundation make it an ideal place to call home. Explore the diverse range of homes available, complete with on-street parking, and discover why so many families are choosing to make Middletown their forever home. Experience the perfect blend of convenience, comfort, and community in this charming New York city!

Newest Middletown Homes with On Street Parking features

$380,000

3 Beds ⋅ 3 Baths ⋅ 1048889 MLS

Welcome to 13 Old Anvil Lane, a conveniently located Middletown home offering comfort, flexibility, and easy access to everything the area has to offer. With several updates already completed, the home feels fresh and move-in ready while still leaving room to add your own personal touch. Inside, you’ll find a comfortable and functional layout designed for everyday living. Plenty of bedrooms and bathrooms for the whole family. One of the home’s standout features is the full walk-out basement, offering excellent potential for additional living space, a recreation room, home office, gym, workshop, or extra storage. A private fenced-in yard is easy to maintain but offers additional gathering space for friends, family, and pets. Located just minutes from shopping like the Galleria Mall and Route 211, dining, Garnet Hospital, schools, major highways (I-84, 17/ I-86), gyms, and train transportation, this property makes commuting and daily errands exceptionally convenient. Whether you're looking for your first home, additional space, or a property in a highly accessible location, 13 Old Anvil Lane offers a great combination of value, versatility, and convenience in the heart of the Middletown area.

13 Old Anvil Lane, Middletown

$299,900

3 Beds ⋅ 1 Baths ⋅ 1041109 MLS

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.

256 Cottage Street, Middletown

$395,000

3 Beds ⋅ 2 Baths ⋅ 1035628 MLS

2 family home in low traffic setting. 1st floor is 3 bedroom @ $1350./month plus utilities 2nd floor is 2 bedroom @ $1100/mo plus utilities Ist floor lease is annual until July 2027. 2nd floor month to month. Old storage building out back. Taxes about $500/mo insurance about $150./mo water about $50./mo

23 Bonnell Street, Middletown

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