Middletown Homes with Driveway Parking features

Welcome to Middletown, New York—a charming city nestled in the heart of Orange County, where small-town warmth meets modern convenience. With its rich history, vibrant community, and stunning natural surroundings, Middletown offers an exceptional quality of life for residents and newcomers alike. Conveniently located just a short drive from the bustling cities of New York and New Jersey, Middletown provides an ideal balance of suburban tranquility and urban accessibility.

One of the standout features of homes in this delightful city is the availability of driveway parking. Imagine returning home after a long day to find your vehicle safely parked just steps from your front door. Driveway parking not only adds convenience but also enhances the overall appeal of your property. Whether you have a growing family, enjoy hosting friends, or simply value the ease of access, homes with driveway parking in Middletown cater to your lifestyle needs.

Middletown boasts a diverse array of real estate options, from charming single-family homes to modern townhouses, many of which feature spacious driveways. This added benefit allows for ample parking space, making it easy to accommodate guests or store recreational vehicles.

As you explore the neighborhoods of Middletown, you’ll discover a welcoming community filled with parks, shops, and local eateries, all while enjoying the beautiful landscapes that Orange County has to offer. Experience the charm of Middletown, where your dream home with driveway parking awaits!

Newest Middletown Homes with Driveway Parking features

$1,885,000

2 Beds ⋅ 2 Baths ⋅ 1048430 MLS

Exceptional 33.6-acre equestrian property in the Town of Wallkill, thoughtfully developed for serious equestrians. Classified by Orange County as a Horse Farm and located within an NYS Agricultural District, it features a substantial barn complex, indoor and outdoor riding arenas, numerous paddocks and turnout areas, supporting structures, and a two-bedroom apartment for on-site living. The grounds include approximately 15 medium-size grass paddocks, 8 smaller sand paddocks/turnouts near the barn for winter and inclement-weather use, a dedicated medical turnout, and a fenced field of approximately 6.5 acres with an interior fenced area surrounding a 30 x 64 loafing shed built in 2013. The shed includes a 12 x 16 stall, feed room, storage room, and 30 x 48 matted area with wall-mounted hay feeders, providing flexibility for turnout, rotation, rehabilitation, and herd management. Many exposed wood edges are protected by metal edging to help prevent chewing and reduce wear. Each paddock has access to one or more Nelson automatic waterers. Numerous frost-resistant outdoor faucets, plus one in the barn, provide backup access to fresh water, while electrical outlets throughout the grounds support water heaters, tools, and daily needs. Built in 2007, the main barn is designed for efficient horse care. A 16-foot-wide center aisle serves 8 approximately 12 x 12 stalls, each with rubber mats and Nelson automatic waterers. Two wash/grooming stalls feature hot and cold water and heat lamps. A climate-controlled tack room offers protected storage for saddles, bridles, and equipment. A dedicated feed room includes a storage closet. A separate utility room has a washer and dryer, with numerous closets throughout the barn for organization. A camera system provides coverage in each stall and throughout the barn. Above, a massive hayloft includes storage closets and individual hay chutes serving the stalls below. It accommodates approximately 1,400–1,600 oversized 50–55 lb. bales of hay, plus substantial bedding-pellet storage on a reinforced plywood section suitable for pallet-jack movement. Covered ventilation hatches provide airflow and protection from the elements. A heated and air-conditioned barn lounge offers year-round comfort for riders, trainers, staff, and guests and is appointed with quality cabinetry, granite countertops, sink, microwave, under-counter refrigerator, tile flooring, and recessed lighting. A heated and air-conditioned half bath is appointed with quality finishes. The approximately 1,280 sq. ft. two-bedroom apartment features an open living layout, granite kitchen with generous cabinetry and peninsula offering additional workspace and seating potential, full bath, and utility/laundry area, well suited for an owner, trainer, barn manager, staff member, or guests. The 84 x 214 indoor riding arena is equipped with TravelRight dust-free footing for comfortable year-round riding and training and is complemented by a 130 x 235 outdoor arena. Permanent four-board and no-climb top-board fencing, gates, established lanes, and an organized barn-and-paddock layout enhance day-to-day horse management. An automatic entrance gate provides controlled access. A backup generator supports the property during outages, while a hand pump on the well offers another means of obtaining water for animals during a prolonged outage. Conveniently located a short drive from Route 17/I-86 Exit 119, the property combines easy regional access with the privacy and space of a country equestrian setting. The acreage, extensive infrastructure, riding facilities, and on-site accommodations create a rare opportunity to acquire an established horse property in the Middletown/Town of Wallkill area. Available as 120 Shaw Road on its own or as a package with 174 Shaw Road, adding approximately 3.8 acres and an additional building site for expansion, future development, residential use, or enhanced equestrian operations.

120 Shaw Road, Middletown

$390,000

3 Beds ⋅ 3 Baths ⋅ 1049937 MLS

The flooring on both floors of the house was replaced, and the central air conditioning, hot water boiler, dryer, dishwasher, stove, and Robam range hood were all replaced. Property Highlights Peaceful Cul-de-Sac Setting: Situated on Deer Court Drive, offering minimal drive-through traffic, enhanced privacy, and a safe, quiet street environment. Functional Living Space: Features a comfortable, well-proportioned layout designed for modern family living, entertaining, and work-from-home flexibility. Spacious Outdoor Area: Ample yard space ideal for outdoor gatherings, gardening, play areas, or relaxing in a serene natural setting. Turnkey Appeal: A welcoming entryway and curb appeal with well-maintained structural elements and grounds. Neighborhood & Community Advantages Prime Commuter Location: Convenient access to major regional transit corridors, including Route 17 (Future I-86), Interstate 84, and the Middletown-Town of Wallkill Metro-North station for hassle-free travel across Orange County and into New York City. Proximity to Everyday Conveniences: Minutes away from the Route 211 commercial corridor, Galleria at Crystal Run, major retail hubs, supermarkets, medical facilities (including Garnet Health Medical Center), and dining options. Hudson Valley Lifestyle: Close to local parks, hiking trails, golf courses, and farm-to-table markets, offering an ideal blend of suburban convenience and scenic countryside. Strong Community Atmosphere: Established, family-friendly residential neighborhood characterized by well-kept properties, mature trees, and high pride of ownership.

45 Deer Ct Drive, Middletown

$550,000

4 Beds ⋅ 3 Baths ⋅ 1049857 MLS

Beautiful home for Sale that features 4 bedrooms with 2.5 baths in a desirable area of Middletown just minutes from Orange County Community College. Do NOT let the outside fool you as this home is bigger than expected inside as it has many finished levels! Newly remodeled and ready for its final touches. Open floor layout from Living room to dining room & kitchen all with newly stained hardwood floors. The kitchen features new cabinets, granite counters and new stainless steel appliances right out the box! 4 bedrooms are located on the upper level, one which is a Suite with its own private bath and shower. Completely remodeled tiled bath with new toilet vanity & sink. A 2nd full bathroom with a tub AND tiled shower completes the upper floor. Again all new top to bottom! A finished lower level offers a Family room, office, and a 3rd half bath along with a laundry room with a new washer & dryer! So much open space is found in this level ideal for an oversized family room, entertainment area, office or workout room. The basement is ALSO finished adding more than enough storage space if it’s needed. Nice size yard that just needs to be cleaned up ideal for gathering & entertaining. Grill and enjoy morning coffee right off the newly pavered patio!!! Plenty of parking along with a 2 car garage. Among some of the upgrades this home offers are the new roof, baths, kitchen, new mechanicals and more! Close proximity to Schools, Colleges, Touro Medical, Garnet Health, and shopping. Call and make this house your home! (AS-IS SALE)

44-50 Ingalls Street, Middletown

$510,000

4 Beds ⋅ 3 Baths ⋅ 1049537 MLS

Welcome to a move-in ready, three-story home designed for easy & comfortable living. The open floor plan feels bright and spacious, with freshly primed walls, updated lighting, and durable flooring that stands up to daily life. You will appreciate practical features like a dedicated laundry room and plenty of closet space for organization. The kitchen comes fully equipped with new cabinets and brand new stainless steel appliances. Sliding glass doors connect the interior to awesome outdoor spaces, including a front porch, back deck, and upper balcony. This home offers great style, real comfort, and low-maintenance living at an affordable value!

326 North Street, Middletown

$599,900

3 Beds ⋅ 2 Baths ⋅ 1047583 MLS

Welcome to 53 Highland View Place! Built in 2018 and situated on a spacious 3.5-acre lot, this beautiful 1,839 sq. ft. ranch offers modern construction, comfortable living, and incredible potential for future expansion. The bright, open-concept layout creates a spacious and inviting feel, perfect for both everyday living and entertaining. The home features municipal water and sewer, natural gas, central air conditioning, and an attached two-car garage. A full unfinished basement provides plenty of storage and even more possibilities for the future. One of the home's standout features is the upper level, offering approximately 843 sq. ft. of space, including two large unfinished bonus rooms ready for your vision. Finishing this area offers the potential to add significant additional living space and create a home with **over 2,500 sq. ft. of finished space**! Whether you envision additional bedrooms, a home office, playroom, gym, or bonus space, the possibilities are endless. Located on 3.5 acres in a beautiful newer neighborhood surrounded by attractive homes, this property offers the space of a large lot while still enjoying a neighborhood setting. Move in and enjoy it today while having tremendous room to grow in the future. Don't miss this one!

53 Highland View Place, Middletown

$469,000

4 Beds ⋅ 3 Baths ⋅ 1049053 MLS

Welcome to 1413 Goshen Turnpike, a spacious home offering comfortable living in a convenient Middletown location. With approximately 1,796 square feet of living space, this home provides plenty of room for everyday living, entertaining, and working from home. The desirable layout includes four bedrooms, two full baths, and a convenient half bath. Enjoy the best of both convenience and location, with shopping, dining, entertainment, and everyday amenities just minutes away. The Galleria at Crystal Run, featuring more than 100 retailers including Target, Macy’s, JCPenney, and DSW, is approximately 5–10 minutes away, while Walmart, grocery stores, restaurants, and additional shopping are also nearby. For commuters and those looking to enjoy the Hudson Valley, the property offers easy access to major roadways and is approximately 70 miles from New York City, making Manhattan roughly a 90 minutes drive depending on traffic. Middletown’s Metro-North/Port Jervis Line provides another option for traveling toward NYC. A wonderful opportunity to enjoy the space and comfort of a four-bedroom home while remaining close to shopping, dining, transportation, and all that the Hudson Valley has to offer.

1413 Goshen Turnpike, Middletown

$899,900

4 Beds ⋅ 4 Baths ⋅ 1048837 MLS

Set on a private, wooded one-acre property in Middletown, this remarkable mid-century modern residence offers a rare opportunity to own a home designed and personally occupied by renowned local architect Dennis Jurow. With more than 4,000 square feet of living space, the home reflects Jurow’s distinctive architectural vision through its dramatic design, abundant natural light, and seamless relationship with the surrounding landscape. Inside, soaring ceilings and expansive walls of glass create an open and airy atmosphere, while triangular clerestory windows and striking architectural lines add visual interest throughout. Ten sliding glass doors bring the outdoors into nearly every aspect of the home, providing an effortless connection to the property’s mature trees, private grounds, and peaceful setting. The residence has been lovingly preserved, allowing many of Jurow’s original design elements to remain part of the home today. Custom built-ins, distinctive tile flooring, original lighting, sunken gathering spaces, and thoughtfully arranged living areas highlight the character and craftsmanship of the original design. One of the home’s most unique features is Jurow’s original architectural studio, a space that can continue to serve as a creative workspace or easily function as a private office or professional suite. An additional wellness room or office offers further flexibility for work, relaxation, or everyday living. The outdoor spaces are equally inviting. Surrounded by mature trees and natural landscaping, the property offers multiple areas for entertaining and relaxing, along with an in-ground pool that creates a private retreat during the warmer months. The home’s zoned living areas also allow for efficient heating and cooling while providing comfort throughout its expansive footprint. Distinctive, thoughtfully preserved, and rich with local architectural history, this is a residence unlike the typical offering. From its signature mid-century details to its extraordinary connection between indoor and outdoor living, the property presents a unique opportunity to become the next steward of one of Dennis Jurow’s most personal designs.

19-21 Lincoln Terrace Unit #19, Middletown

$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

$470,000

3 Beds ⋅ 2 Baths ⋅ 1047868 MLS

Welcome to this amazing 3-bedroom ranch in Minisink! Offering a spacious open floor plan, this home is designed for comfortable everyday living and effortless entertaining. The primary bedroom features its own walk-in closet, while two full bathrooms provide plenty of convenience for family and guests. The finished basement offers additional living space with endless possibilities for a recreation room, home office, gym, or media area. An attached two-car garage and generous driveway provide ample parking and storage. Outside, enjoy your own private backyard retreat! The large back deck overlooks a gorgeous, level yard, complete with a beautiful inground pool and pool house; the perfect setting for summer entertaining, relaxing, and creating memories with family and friends! Move-in ready and the perfect blend of comfortable living, functional space, and an exceptional outdoor oasis. Come see all this special home has to offer!

487 Greenville Turnpike, Middletown

$385,000

2 Beds ⋅ 2 Baths ⋅ 1047462 MLS

Welcome to this move-in ready 2-bedroom, 2-bath townhouse with NO HOA fees! This well-maintained home has been freshly updated inside and out, featuring fresh interior and exterior paint, a freshly painted deck, brand-new flooring on the main and lower levels, and new carpeting in the upstairs bedrooms. The bright eat-in kitchen offers ample cabinet space and plenty of natural light. The inviting living room features a cozy fireplace and opens directly to a private deck overlooking a peaceful wooded setting—perfect for relaxing or entertaining. Upstairs, the primary bedroom features a private en-suite full bath and its own balcony, creating a comfortable retreat with a private outdoor space. Additional highlights include in-home laundry and a one-car garage. Conveniently located near shopping, dining, major highways, bus transportation, and commuter train service to NYC. Move right in and enjoy the comfort and convenience of townhouse living without the added expense of HOA fees!

22 Mayer Drive, Middletown

$1,150,000

4 Beds ⋅ 4 Baths ⋅ 1046894 MLS

Tucked away on 4 sprawling, private acres, this 5,360-square-foot contemporary estate delivers the rare combination of country seclusion, equestrian-ready grounds, and true move-in luxury. Whether you're searching for a peaceful retreat, room to bring your horses, or a multigenerational layout with built-in flexibility, 289 Pine Grove Road checks every box. Step through the soaring foyer into a light-filled main level anchored by cathedral ceilings, skylights, and rich hardwood floors throughout. The gourmet eat-in kitchen, with granite countertops and a generous pantry flows into a formal dining room built for hosting, while the sunken living room and enclosed sunroom with its own wet bar create effortless indoor entertaining space. Upstairs, the primary suite is a true retreat: vaulted ceilings, a cozy fireplace, a dedicated sitting area, and a private balcony overlooking sweeping water and countryside views. The spa-inspired primary bath features custom stone finishes, and two additional spacious bedrooms plus a second full bath complete the upper level. The fully finished, walk-out lower level adds exceptional flexibility, with its own kitchen, full bath, bedroom and additional office/den makes it the perfect accessory apartment, guest suite, or home office setup. Outside, the property truly sets itself apart: mature barn structures and stables ready for horses, a peaceful stream winding through the land, a custom Koi pond, and a charming gazebo overlooking the fenced yard. Multiple deck, patio, and balcony areas make it easy to take in the Hudson Valley sunsets from every angle. Rounding out the offering is a 2-car attached garage all set within the highly regarded Minisink Valley Central School District. Properties combining this much land, living space, and equestrian infrastructure rarely come to market. Schedule your private tour today before it's gone.

289 Pine Grove Road, Middletown

$549,900

4 Beds ⋅ 3 Baths ⋅ 1047247 MLS

Welcome to a home that offers the best of both worlds—peace, privacy and a tucked-away setting, while still providing convenient access to local shopping, major roadways and transportation. With generous living space, thoughtful updates and the added benefit of public water and sewer, this beautifully maintained home is ready for its next owner. A charming wraparound porch immediately sets the tone, creating a unique, elevated feel that almost makes you feel as though you are living in a treehouse. Inside, the home offers an abundance of space and a layout that works beautifully for both everyday living and entertaining. The large country kitchen is the heart of the home, with plenty of room for a substantial dining table and direct access through sliding glass doors to the generous rear deck and private backyard. Whether enjoying a quiet morning coffee, hosting a summer barbecue or gathering around the backyard masonry wood-burning firepit, the outdoor spaces are designed to be enjoyed. Upstairs, you will find four bedrooms plus a dedicated office, providing tremendous flexibility for today’s lifestyle. The spacious primary suite features an updated private bathroom and two walk-in closets, with one of those spaces also offering the potential to serve as a private office, dressing room or additional flex space. The home has been exceptionally well cared for, with numerous important improvements already completed. Updates include a new roof in 2020, furnace in 2018, renovated bathrooms in 2022, central air conditioning in 2024, newer appliances, a new washer in 2026, dryer in 2024, new hot water heater in August 2026, fresh interior paint throughout in August 2026, and new flooring in all bedrooms, the laundry room, pantry and primary walk-in closets. A generator is also included, offering additional peace of mind. Outside, the private backyard provides plenty of room to relax and entertain, highlighted by a wood-burning firepit with gas and electric already on site. Spacious, private, beautifully maintained and filled with meaningful upgrades, this home offers a rare combination of peaceful living and everyday convenience. With public utilities, flexible living space, inviting outdoor areas and so many major improvements already completed, this is a property that is truly easy to appreciate. Located in the desirable Pine Bush School District.

106 Freezer Road, Middletown

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