Middletown Homes with Off Street Parking features

Welcome to Middletown, NY, a charming city nestled in the heart of Orange County. Known for its rich history and vibrant community, Middletown is an ideal place for families seeking a welcoming environment with excellent educational opportunities. The Middletown School District is highly regarded, offering a robust curriculum that emphasizes academic excellence, creativity, and personal growth. With dedicated teachers and a variety of extracurricular activities, students are encouraged to explore their interests and develop their talents, ensuring a well-rounded education.

Middletown is not only known for its outstanding schools but also for its diverse housing options. Many homes in the area feature off-street parking, providing convenience and peace of mind for residents. Imagine coming home after a long day, knowing you can park your vehicle safely and easily, right at your doorstep. This feature is particularly beneficial in a bustling city like Middletown, where street parking can sometimes be a challenge.

Whether you're looking for a cozy single-family home or a spacious townhouse, Middletown's real estate market has something for everyone. The combination of quality education, community spirit, and practical home features like off-street parking makes Middletown an attractive choice for families and individuals alike. Explore the possibilities and discover why so many are proud to call Middletown home!

Newest Middletown Homes with Off Street Parking features

$419,900

4 Beds ⋅ 1 Baths ⋅ 1031475 MLS

Welcome to this charming and well-maintained 4-bedroom home offering a practical layout and timeless character. The main level features a bright living room, formal dining room, eat-in kitchen, two bedrooms, and a full bath, while the upper level provides two additional bedrooms with flexible living space. Recent improvements include a new roof (2024), vinyl double-pane windows installed in 2018, and a resurfaced driveway completed in 2023. A bright enclosed front porch adds additional living space and creates a warm, welcoming entrance. Outside, enjoy a generous backyard surrounded by mature trees, offering a private and peaceful setting, along with a detached two-car garage and ample off-street parking. Conveniently located near schools, shopping, restaurants, parks, and major highways, this home offers the perfect balance of everyday convenience and a peaceful residential setting. Some interior photos have been virtually staged for illustrative purposes only to demonstrate potential furniture placement. The property is being sold in its actual unfurnished/as-is condition.

39 California Avenue, Middletown

$299,900

3 Beds ⋅ 2 Baths ⋅ 1030626 MLS

Step inside this classic 3-bedroom, 2-bath Colonial and imagine the possibilities. Offering approximately 1,610 square feet, the home features a traditional layout with a living room, formal dining room, spacious kitchen, and a flexible first-floor bonus room that can serve as a den, home office, or recreation space. A dedicated laundry area adds everyday convenience, while the covered front porch overlooks an open view with no homes directly across the street. Upstairs are three bedrooms, including a primary bedroom with a walk-in closet, along with a second full bath. The flat 37' x 150' lot includes a usable backyard, shared driveway, and rear parking for approximately three vehicles. Public water, public sewer, natural gas heat, and a partial unfinished basement provide a functional starting point. The home is ready for its next owner to bring their vision and update it to their taste. Located just one block from Sproat Street Park and Pool, with convenient access to I-84, Route 17, shopping, medical facilities, and nearby parks

158 Cottage Street, Middletown

$325,000

2 Beds ⋅ 1 Baths ⋅ 1020584 MLS

AFFORDABLE COLONIAL HOME with low taxes, two bedrooms, one bathroom, and flexible extra space. This 1,080 sq. ft. home features vinyl siding, municipal services, and natural gas for heat, hot water, and cooking. Enjoy private off-street parking for up to three cars, with curb-cut access from two streets. The home offers classic charm and character, a covered front porch, concrete walkways, and outdoor space suitable for a small garden, play area, or additional parking. The first floor includes the main living areas: living room, kitchen, and dining area. Upstairs are two bedrooms and a full bathroom, with a walk-up attic providing extra storage. The walk-out basement offers space for a family room, laundry area with washer and dryer, plus windows and a door leading to a concrete patio overlooking the green yard and private parking. The first and second floors currently have carpet, with original hardwood floors underneath. Conveniently located near services and amenities, within walking distance of the community college and just a five-minute drive to the I-84 intersection. With ownership costs comparable to rent, this charming home is a great opportunity to buy instead of renting a home.

10 Forest Avenue, Middletown

$339,900

3 Beds ⋅ 2 Baths ⋅ 1015028 MLS

Move in ready 3 bedrooms, 2 bathroom home. Clean and freshly painted. Updated kitchen and bathrooms. Located on a dead end street. Private Fenced-in yard. Conveniently located minutes from local shops, restaurants, Galleria Mall, Garnet Health and close proximity to I86 and I84. Very easy to show. Call today for your own private viewing.

101 N Beacon Street, Middletown

$349,000

2 Beds ⋅ 2 Baths ⋅ 1014402 MLS

This 3 bedroom home is being offered by the original owners. Three spacious bedrooms. Family room with custom fireplace. Oversized garage with laundry. Elementary and middle schools just down the road. Middletown High School offers many college courses. Beautiful sunroom with pellet stove. Two 275 gal oil tanks. Beautiful spacious back yard with shed. Extra black topped parking for RV, boat storage or extra guests.

4 Lorelei Drive, Middletown

$399,900

5 Beds ⋅ 3 Baths ⋅ 1002381 MLS

Welcome to an opportunity that is becoming harder and harder to find. This multi-family property sits on a nearly half-acre lot in the City of Middletown and offers investors, contractors, and ambitious buyers the chance to create significant value. With 2,151 square feet, five bedrooms, three full bathrooms, and income-producing potential, this is the type of property that rewards vision and execution. Previously utilized as a three-unit property, the home will need to be used as a two-family residence moving forward per city guidelines. The opportunity here is simple: renovate, improve, and create a property capable of generating rental income for years to come. Whether your goal is to live in one unit while collecting rent from the other, add a cash-flowing asset to your portfolio, or pursue a value-add investment strategy, the foundation is already in place. Building plans are available to help complete the first-floor renovation, providing a head start for the next owner and helping bring the project to the finish line. Outside, you’ll find a large driveway with ample off-street parking, a rear deck, and a level backyard that adds both functionality and tenant appeal. While substantial repairs and updates are needed, opportunities like this are becoming increasingly scarce. The combination of size, lot dimensions, rental potential, and available building plans creates a compelling opportunity for the buyer willing to put in the work. Conveniently located near shopping, restaurants, schools, healthcare facilities, public transportation, and major commuter routes, the location further strengthens the property’s long-term appeal. Whether you’re looking to build equity, generate future rental income, expand your investment portfolio, or create a multi-generational living arrangement, this property offers the flexibility to support a variety of goals. Bring your contractor. Bring your vision. The plans are available, the potential is clear, and the opportunity to create something special is waiting.

37 Monhagen Avenue, Middletown

$225,000

2 Beds ⋅ 1 Baths ⋅ 1011268 MLS

Opportunity awaits! 2-bedroom, 1-bath one-family home with 2-car garage. Includes a large patio above the garage. Eat in kitchen with refrigerator and gas stove. The seller gutted and renovated the house in 1989. Property requires complete renovation and is being sold as-is. Ideal for investors, contractors, or buyers looking to build equity. Convenient location close to shopping, schools, and commuter routes. Cash or renovation financing preferred. Bring your vision and unlock this property's potential! The electric is on, heat and hot water, municipal water & sewer are hooked up and on. Possible to expand the house above the garage.

45 John Street, Middletown

$299,900

3 Beds ⋅ 2 Baths ⋅ 1005556 MLS

Say hello to possibility! A Middletown townhouse with space, flexibility, and room to make it your own. With 3 bedrooms, and a main-level flex space w/ closet, 2.5 bathrooms, plus inviting outdoor space, this home is ready for your personal touch. Close to everything Middletown offers—shops, dining, parks, and commuter routes—this is a smart move with big potential. Make 2 S. Aspen Rd your next upgrade. No HOA. Being sold as-is.

2 S Aspen Road, Middletown

$575,000

3 Beds ⋅ 3 Baths ⋅ 1003208 MLS

For Sale: Income-Producing Mixed-Use Building in Prime Downtown Middletown Take advantage of this exceptional opportunity to own a versatile, income-generating property in the heart of Downtown Middletown—an up-and-coming city with a pro-business government and strong growth potential. Property Overview: First Floor: Spacious 2,000 sq. ft. commercial space, currently used as a retail store, office, and storage area, plus a large multi-purpose room perfect for meetings, events, or classes Includes a full bathroom, retail front entrance, and private rear access Flexible layout offers potential for multiple businesses or tenants Second Floor: Two fully rented residential apartments: One large 2-bedroom unit One spacious 1-bedroom unit Each with its own kitchen, living room, and full bathroom Approx. 800 sq. ft. per unit Private Parking Lot: Rear parking accommodates up to 5 vehicles Unbeatable Downtown Location: Just steps from City Hall, the NYC bus terminal, the public library, restaurants, shops, and more—this location provides outstanding visibility and walkability for both commercial and residential tenants.

20 John Street, Middletown

$199,000

1 Beds ⋅ 1 Baths ⋅ 927923 MLS

Welcome to 51 S Shore Drive, a charming and thoughtfully updated bungalow retreat nestled on a private, wooded 9,374 sq ft lot with sparkling lake views in scenic Middletown, NY. This beautifully curated 1-bedroom, 1-bath lakefront getaway offers 360 square feet of smart, stylish living space perfect for a weekend escape, vacation rental, or year-round peaceful living. Step inside to a crisp, modern interior featuring a cozy stone-accented fireplace, sleek black cabinetry, upgraded appliances, and luxury vinyl plank flooring. The open-concept living space is bright and inviting with fresh finishes, vaulted ceilings, and picture windows that frame the surrounding forested hillside. Step outside and you'll be swept away by the home's crown jewel, a brand-new oversized deck with ample space for grilling, lounging, and soaking up nature’s beauty. Whether you're sipping your morning coffee or enjoying sunset dinners, this deck offers a front-row seat to the tranquil lake just beyond the trees. The lot itself is partly wooded and gently sloped, offering both privacy and unobstructed water views. It's the perfect backdrop for nature lovers, creatives, or anyone seeking a peaceful recharge in the heart of the Hudson Valley. Located less than 90 minutes from NYC, and close to local farms, wineries, hiking trails, and charming small towns, this home is ideal for weekenders, investors, or full-time residents who crave a simpler, quieter lifestyle with modern comforts. Escape the ordinary, 51 S Shore Drive is lake living reimagined.

51 S Shore Drive, Middletown

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