Middletown Homes with On Street Parking features

Welcome to Middletown, New York—a vibrant city nestled in the picturesque Orange County. Known for its rich history and diverse community, Middletown offers a blend of suburban charm and urban amenities. With its beautiful parks, bustling downtown area, and a variety of shopping and dining options, this city is perfect for families, young professionals, and retirees alike.

Middletown is conveniently located just a short drive from New York City, making it an ideal spot for commuters seeking a peaceful retreat from the hustle and bustle of city life. The area boasts excellent schools, a strong sense of community, and a plethora of recreational activities, from hiking in nearby state parks to enjoying local festivals and events throughout the year.

For those considering a move to Middletown, you'll be pleased to find a variety of homes that cater to different lifestyles and budgets. One standout feature of many residences in this charming city is the availability of on-street parking. This convenient amenity not only provides easy access for homeowners and their guests but also enhances the overall appeal of the neighborhood. Imagine coming home after a long day, knowing you can effortlessly park right outside your door!

Whether you’re searching for a cozy bungalow or a spacious family home, Middletown has something to offer everyone. With its welcoming atmosphere and abundant amenities, it’s no wonder that so many are choosing to call Middletown home. Come explore the possibilities and discover the perfect place for you!

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

$4,600,000

941626 MLS

Prime commercial property located in the City of Middletown on 1.4 Acres that is offering: a thriving, well-established auto body shop and repair business complemented by four income-producing rental buildings. Each building has undergone recent updates (roof, HVAC, electrical, interiors). Strong, diversified income streams with substantial NOI potential. Located in a high-traffic corridor with excellent access and signage. Ideal for hands-on owner-operator or investment portfolio seeking stable cash flow and future upside through leasing and shop expansion. This property has several tenants and also consists of storage units and has the local railroad that passes by as well. This property is zoned I-1

80 Wisner Avenue, 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

$354,900

3 Beds ⋅ 1 Baths ⋅ 1033985 MLS

Welcome home to this beautifully maintained 3-bedroom, 1-bath Colonial in the City of Middletown. Conveniently located near shopping, restaurants, parks, schools, and major commuter routes, this home blends classic charm with practical everyday living. From the moment you arrive, you'll be drawn to the expansive wraparound front porch—the perfect place to enjoy your morning coffee or unwind at the end of the day. Inside, you'll find beautiful hardwood floors, abundant natural light, and a functional layout featuring a spacious living room, formal dining room, and an eat-in kitchen. Just off the kitchen, a versatile area offers endless possibilities as a mudroom, home office or additional sitting area, with the convenience of a first-floor laundry room nearby. Upstairs, you'll find three comfortable bedrooms and a full bathroom, providing a practical layout for everyday living. Outside, the generously sized yard offers room to garden, entertain, or simply enjoy the outdoors. A standout feature of the property is the large detached barn, providing exceptional space for vehicles, storage, a workshop, or recreational equipment. If you're looking for a home that offers classic character, flexible living spaces, and outstanding outdoor storage, this Middletown gem is one you won't want to miss.

41 Roosevelt Avenue Unit #39, Middletown

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