Middletown Homes with Off Street Parking features

Welcome to Middletown, New York – a vibrant city nestled in the heart of Orange County. Known for its rich history and charming small-town feel, Middletown offers a unique blend of urban amenities and natural beauty. With a population that embraces community spirit, you’ll find friendly faces and a welcoming atmosphere at every turn. The city boasts a variety of parks, local shops, and restaurants, making it a perfect place for families, young professionals, and retirees alike.

One of the standout features of homes in Middletown is the availability of off-street parking. In this bustling city, having your own designated parking space is a significant advantage. Imagine coming home after a long day and effortlessly parking your car right outside your door, away from the hustle and bustle of street parking. These homes with off-street parking not only provide convenience but also enhance your property’s value and appeal.

Whether you’re looking for a cozy single-family home, a charming townhouse, or a spacious multi-family unit, Middletown has a diverse range of properties to suit your needs. Many of these homes feature modern amenities, beautiful yards, and easy access to local attractions. With off-street parking as a key feature, you can enjoy peace of mind knowing your vehicle is secure and easily accessible.

Explore the delightful neighborhoods of Middletown, where community and comfort come together. Discover your dream home today and experience all that this enchanting city has to offer!

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 a welcoming place to relax. Outside, enjoy a generous backyard, a detached two-car garage, and ample off-street parking. Conveniently located near schools, shopping, restaurants, parks, and major highways, this home offers comfort, convenience, and everyday functionality in an established neighborhood. Some photos have been enhanced for presentation purposes. Some interior photos have been virtually staged for illustrative purposes only to demonstrate potential furniture placement. The property is being sold in its current, unfurnished, as-is condition.

39 California Avenue, Middletown

$469,000

5 Beds ⋅ 3 Baths ⋅ 1031210 MLS

Welcome home to this breathtaking Farmhouse-style retreat, perfectly set back from the main road amidst mature hydrangeas and Rose of Sharon. Step onto the sprawling, large rocking chair front porch—part of an expansive covered porch that wraps around three sides of the home—and experience true rustic charm before you even step inside. Upon entry, you’ll be in awe of the soaring vaulted ceilings, stunning wide plank wood floors running throughout, and a magnificent floor-to-ceiling stone fireplace. At the heart of the home is a gourmet country-style kitchen designed for entertaining. It features a spacious eat-in island, prep bar sink, and a high-end gas cooktop complete with interchangeable wok burner and griddle attachments. Dual sets of sliding glass doors seamlessly connect the kitchen to the rear deck for effortless outdoor dining. The main level features 2 light-filled bedrooms (one with private slider access to the deck) and a full bathroom. The upper level has additional bedrooms, a full bath, and a charming loft area overlooking the main living room. The basement has a cozy family room, a wet bar, 3rd full bath, and dedicated laundry room. Multi-level outdoor living including open and covered rear decks, plus a unique enclosed porch featuring a dog door leading directly to a secure 20 x 30 enclosed dog pen. A rare blend of rustic elegance, modern amenities, and peaceful seclusion—schedule your tour today!

495 Guymard Turnpike, 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

$165,000

1 Beds ⋅ 1 Baths ⋅ 1024578 MLS

A charming 1940 bungalow located in the highly desirable Minisink Valley School District, this home sits on a quiet 0.23-acre lot and makes an excellent starter home with low taxes. The front door opens into a spacious living area filled with natural light. The main level offers one bedroom plus an office that can serve as a second bedroom if needed. The full basement—not included in the listed square footage—provides additional space ideal for a recreation area, storage, or a bonus room. Outside, enjoy the fenced-in backyard complete with a patio and tree house. Previously rented for $2,000 per month, this property also presents a strong investment opportunity.

488 Tally Ho Road, 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

$635,000

3 Beds ⋅ 3 Baths ⋅ 999526 MLS

Charming Farmhouse Retreat on 2.9 Acres! Nestled on a quiet country road in the Town of Greenville and located within the desirable Minisink Valley Central School District. This beautiful farmhouse-style home offers the perfect blend of comfort, charm, and country living. Inviting home features 3 bedrooms and 2.5 baths with attractive Pergo wood flooring throughout the downstairs, while upstairs offers comfortable carpeting. Step up onto the welcoming covered wrap-around porch and enter through lovely double front doors into a foyer with an impressive cathedral ceiling. The farmhouse kitchen is both stylish and functional, featuring all stainless-steel appliances, granite countertops, and a large center island perfect for gathering with family and friends. The open floor plan leads to a dining area off the kitchen with a stunning bay window looking out onto the beautiful property and sliding glass doors that open to the wrap-around porch; creating a wonderful indoor-outdoor flow. Relax in the spacious living room featuring a cozy gas fireplace - the perfect spot to unwind. The 20x20 bonus room, also with pergo flooring, located above the attached 18x20 garage hosts its own separate entrance and bright airy windows with plenty of natural light; perfect for a potential mother daughter suite. The home includes plenty of storage with a detached one car garage, 18x20 attached garage, easily accessible full attic and 5ft walkable crawl space that is the length of the house and accessible from the kitchen. Peaceful surroundings, charming details, and plenty of room to enjoy country living make this home one you won't want to miss. A must-see property!

5 Decker Drive, Middletown

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