Middletown Homes with Detached Parking features

Welcome to Middletown, New York – a charming city nestled in the heart of Orange County, where small-town charm meets modern convenience. Known for its rich history and vibrant community, Middletown offers a delightful blend of urban amenities and picturesque landscapes. With its convenient location just a short drive from both the Hudson Valley and New York City, residents enjoy the best of both worlds: the tranquility of suburban living combined with easy access to the hustle and bustle of city life.

Middletown is celebrated for its diverse neighborhoods, each offering unique character and appeal. Whether you’re drawn to the quaint historic districts or the modern developments, you’ll find a range of homes that cater to various lifestyles and preferences. One of the standout features of many properties in this area is the availability of detached parking. Imagine the convenience of having your own private parking space or garage, providing not only security for your vehicles but also extra storage options for your belongings.

The homes in Middletown with detached parking are perfect for families, professionals, or anyone who values the ease of access and additional space. These properties often come with spacious yards, allowing for outdoor gatherings and relaxation, while still being close to local parks, shopping centers, and schools.

Explore the charm of Middletown, where community spirit thrives, and the comfort of home awaits. Whether you’re a first-time buyer or looking to settle down, this city has the perfect place for you to call home. Come and discover the beauty and convenience that Middletown has to offer!

Newest Middletown Homes with Detached 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

$279,000

4 Beds ⋅ 2 Baths ⋅ 1027125 MLS

Attention investors, contractors, and renovation enthusiasts! This spacious fixer-upper offers an incredible opportunity to restore a classic home on a rare double lot. Situated on approximately two combined parcels with a detached 4-car garage, this property offers abundant space and endless potential. The home currently features existing electrical service, plumbing, a functional full bathroom, multiple newer windows, and two new garage doors. While renovations are needed—including cosmetic updates, roof, kitchen, HVAC, drywall, and additional improvements—the property provides an excellent foundation for your vision. Conveniently located just minutes from Route 211, I-84, Route 17/I-86, and I-87, with easy access to shopping, dining, the Galleria Mall, and Legoland New York Resort. No HOA. Property taxes are low for a property of this size and location. Property is being sold as-is.

227-229 Linden Avenue, Middletown

$550,000

1020113 MLS

Excellent mixed-use investment opportunity! Conveniently located on a high-visibility corner at a traffic light, this property features a 1,919 sq. ft. commercial storefront on the first floor and two newly renovated 2-bedroom apartments on the second floor totaling approximately 1,727 sq. ft. Each residential unit offers 2 bedrooms, a full bath, a kitchen, and a spacious living room. The commercial space is well suited for a hair salon, barbershop, skincare or beauty spa, nail salon, or other personal care and wellness services (subject to municipal approvals). All three units have been updated and are move-in/rent-ready. With strong rental demand in the area, this property presents an excellent opportunity for investors or owner-occupants seeking an income-producing property. Additional features include storage, a detached one-car garage, and driveway parking as well as on-street parking.

36 Wallkill Avenue, Middletown

$499,999

4 Beds ⋅ 2 Baths ⋅ 1015915 MLS

Welcome to 678 Prosperous Valley Road, a beautifully renovated Colonial nestled on 0.80 acres in the desirable Town of Middletown. Combining timeless character with modern upgrades, this move-in-ready home offers 4 spacious bedrooms, 2 full bathrooms, and approximately 1,861 square feet of thoughtfully updated living space. Recent improvements include a stunning remodeled kitchen, fully renovated bathrooms, new siding, updated flooring, rebuilt structural flooring supports, new decks, and numerous additional upgrades throughout. The home also features a cozy fireplace, full basement with ample storage potential, detached garage, and a private wooded backdrop that creates a peaceful retreat while remaining conveniently located near shopping, schools, restaurants, and major commuter routes. Enjoy the charm of country living with the confidence of extensive recent renovations already completed. Whether you're looking for a full-time residence, weekend retreat, or investment opportunity, this property offers exceptional value, privacy, and modern comfort.

678 Prosperous Valley Road, Middletown

$435,000

3 Beds ⋅ 1 Baths ⋅ 1013260 MLS

BEAUTIFULLY maintain old style 1930's home in the heart of Middletown with low PROPERTY taxes. A must-see home to appreciate it quality and charm. Located near Davidge Park. Commuter Friendly location easy access to Route 17 and interstate highway 84 to Penn and Conn. NJ Transit and a 15 min walk to the Shortline Bus to Midtown Manhattan with Plenty of Parking should you choose to drive to the bus station. Near shopping and the Galleria Mall. Enjoy Peace and Quiet that Middletown has to offer.

11 Columbia Avenue, Middletown

$599,900

4 Beds ⋅ 2 Baths ⋅ 1006587 MLS

Cherished through generations and lovingly maintained by its owners, this remarkable circa home is ready for its next chapter. Set on 3.6 beautifully level acres in the Valley Central School District, the property offers the perfect blend of historic character, functional space, and country charm. As you approach, the care and pride of ownership are immediately evident. A welcoming front porch invites you inside, where you'll discover timeless architectural details and a warmth that only a well-loved home can provide. Upon entry, take notice of the unique concave wall, setting the tone for the character found throughout. The formal living room features a Franklin stove vented through the repointed chimney, complemented by a faux marble mantel, elegant pocket doors, and built-in bookcases. A spacious formal dining room with oversized windows and wide moldings provides the perfect setting for holidays, celebrations, and everyday gatherings. The kitchen offers abundant storage with two deep pantry closets, an additional utility closet, built-in stove, double sink, and convenient half bath. A main-level home office with its own closet creates an ideal work-from-home space. Upstairs, you'll find four generously sized bedrooms filled with natural light. The spacious primary bedroom includes a walk-in closet and linen closet, with indications of a possible original stove location hidden behind the wallpaper. An oversized full bath features a large window and soaking tub. The finished lower level offers additional living space, including a fabulous craft area, family/TV room, and abundant storage. A walk-up attic provides easy-access storage options rarely found today. One of the home's most beloved features is the sunroom—a peaceful retreat where every season brings a new view. Enjoy your morning coffee while listening to birdsong and taking in the beauty of the surrounding acreage. Outside, the possibilities are endless. The level 3.6-acre property is ideal for horses, small animals, gardening, recreation, or simply enjoying open space and privacy. A detached 1,136-square-foot garage/barn offers tremendous flexibility for vehicles, equipment, a workshop, hobbies, or agricultural use. Organic gardens. Rich in character, filled with history, and surrounded by picturesque grounds, this special property offers a rare opportunity to become the next steward of a truly grand old home.

22 Camp Orange Road, Middletown

$639,000

3 Beds ⋅ 3 Baths ⋅ 968515 MLS

ABSOLUTELY GORGEOUS!!! MUST SEE!! QUALITY BUILT WITH BRAND NEW ADDITION AND BRAND NEW DETACHED POLE BARN!!! OVER 7 ACRES !!! 481 Dosen Road offers a rare combination of quality construction, privacy, and usable space, set on 7.4 peaceful acres. This custom-built Lok-N-Logs log home was thoughtfully designed to blend the character of a true log cabin with the comforts needed for everyday living. Surrounded by nature, the property provides a quiet, private setting while still offering a layout and features that make it practical for both full-time living and weekend use. Inside, the home feels warm and inviting from the moment you walk in. Hardwood floors run throughout, and the cathedral ceilings open up the main living space, bringing in natural light and creating an easy, comfortable flow. Custom built furniture throughout the home is included in the sale and compliments the space perfectly. The recently completed first-floor primary suite stands out, featuring a well-designed, spa-inspired bathroom with a large walk-in shower. Just off the suite, a dedicated home office adds convenience for those working from home. Two additional bedrooms and a full bath on the main level provide flexibility for guests, hobbies, or everyday needs. Upstairs, a loft-style suite with its own full bath offers a quiet, separate space that works well as a second primary or private retreat. Outdoor living is just as appealing, with a Trex deck and maintenance-free railings overlooking the property, a natural place to relax and take in the surroundings. For those who need space to work, store equipment, or pursue hobbies, the newly built 30’x30’ detached garage is a standout feature, complete with a full upper level that offers endless potential for a workshop, studio, or future finished space. A large carport behind the garage provides even more room for vehicles, equipment, or recreational use. The full basement adds additional versatility for storage or potential future expansion. Set on over 7 acres in the Town of Wallkill, this property offers the space and flexibility to accommodate a variety of outdoor uses, including the potential for horses or other livestock. Buyers are encouraged to verify specific uses with the Town of Wallkill, but the acreage and layout provide a strong foundation for those interested in homesteading or keeping animals. This is a property that brings together character, functionality, and the flexibility to suit a variety of lifestyles. Whether you’re looking for a full-time residence, a weekend retreat, or a space that allows you to work and create, 481 Dosen Road offers a combination that’s increasingly hard to find. All of this is set in a convenient, central location close to major commuting routes, shopping, medical facilities, and restaurants. Schedule your private showing today.

481 Dosen Road, Middletown

$560,000

4 Beds ⋅ 3 Baths ⋅ 978950 MLS

This beautiful ranch-style property is ready to move in. Amazing upgrades were made to this home with beautiful hardwood floors, 4 bedrooms, 3 bathrooms, a huge finished basement with 3 additional rooms for storage or home office, and it also has space for a personal gym with access to an amazing backyard that features a beautiful above-ground pool, a tennis court, volleyball court, or basketball court. Make it your own choice. This beautiful property has a side deck perfect for family gatherings, BBQ, and more to capture your heart and make it your new home.

77 Upper rd Road, Middletown

$585,000

6 Beds ⋅ 4 Baths ⋅ 971962 MLS

Country Escape of 6 spacious bedrooms offers space, privacy, and a serene setting on 3.38 acres. Just about 75 miles from New York City, it’s close enough for convenient weekend escapes yet far enough to feel like a true retreat feels like a private estate—perfect for those seeking a refined escape from city life A grand foyer opens to a bright, airy layout with high ceilings, large windows, and abundant natural light. The chef’s kitchen is ideal for cooking and entertaining, while a double-sided fireplace brings warmth and charm to both the living and dining areas. The inground pool creates a private outdoor getaway perfect for relaxing or hosting. The primary suite offers a peaceful retreat with ample closet space and an ensuite bath. Additional bedrooms provide flexibility for guests, home offices, or creative spaces. A full walk-up attic offers valuable expansion potential for future living area or long-term growth. A 2-car detached garage adds everyday convenience. Blending timeless Colonial elements with modern flair, this home offers a unique setting that may appeal especially to those seeking a weekend haven, creative escape, or a peaceful alternative to everyday living—while still being minutes from Route 17, shopping, dining, and Hudson Valley amenities.

669 Mountain Road, Middletown

$399,995

3 Beds ⋅ 2 Baths ⋅ 969654 MLS

Welcome to 17 Last Rd, a unique retreat nestled on a sprawling 3.9-acre lot in the heart of Middletown. The upper level features 2 bedrooms and 1 full bathroom, while the lower level offers ground-level access with its own separate entrance, an additional bedroom, and a full bathroom. This versatile 2-bedroom, 2-full-bathroom home is designed to maximize natural light, creating a bright and airy feel throughout the main living spaces. A standout feature of the property is the fully finished lower level, which includes its own entrance and an in-home laundry area. This flexible layout can accommodate a variety of uses such as a home office, guest space, recreation area, or additional living space. Set on approximately 169,884 square feet of level land, the property offers exceptional outdoor space with many potential uses. Previously utilized as a mini-farm for horses, the land provides room for gardens, fencing, outdoor projects, or agricultural hobbies. The exterior also includes a garage suitable for a workshop or storage along with an additional shed for equipment. Despite its peaceful setting, the property remains convenient for commuters. The Metro-North Railroad station in Middletown and the ShortLine Bus terminal are just minutes away, offering connections to New York City. With easy access to Interstate 84 and New York State Route 17, travel throughout the Hudson Valley is convenient. Nearby attractions include the Orange County Fair Speedway, the Galleria at Crystal Run, and the scenic trails of Highland Lakes State Park.

17 Last Road, Middletown

Start Your Search

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.