Middletown Homes with Attached Parking features

Welcome to Middletown, New York – a vibrant city nestled in the heart of Orange County that perfectly blends suburban charm with urban convenience. With its rich history, diverse community, and stunning natural surroundings, Middletown is an ideal place to call home. Located just an hour’s drive from New York City, residents enjoy easy access to metropolitan amenities while savoring the tranquility of small-town living.

Middletown boasts a variety of recreational opportunities, from picturesque parks and scenic hiking trails to local shops and restaurants that reflect the city's eclectic culture. The downtown area is a hub of activity, featuring a mix of historic architecture and modern developments, ensuring there’s always something new to explore. Families will appreciate the excellent schools and community programs that promote growth and connection among neighbors.

When it comes to finding your dream home in Middletown, you’ll be pleased to discover a selection of residences that come with attached parking features. Whether you’re seeking a cozy townhouse or a spacious single-family home, having dedicated parking is a significant advantage. It not only adds convenience to your daily routine but also enhances the overall appeal of your property. Say goodbye to the hassle of street parking and enjoy the ease of coming home to your own secure space.

With its welcoming atmosphere and a variety of housing options, Middletown is more than just a place to live; it's a community where you can thrive. Explore the possibilities today and find your perfect home in this charming city!

Newest Middletown Homes with Attached Parking features

$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, friendly residential neighborhood characterized by well-kept properties, mature trees, and high pride of ownership.

45 Deer Ct Drive, Middletown

$829,999

5 Beds ⋅ 3 Baths ⋅ 1049007 MLS

Experience refine living in this 5 bedroom 3 bath pristine Hi-Ranch, perfectly situated upon 1.52 acres in the highly sought after Pine Bush School District. This home features custom light fixtures in the Kitchen, Dining & Living rooms. The Kitchen features a Breakfast bar; Formal Dining Room with Sliders to the deck; Formal Livingroom with an electric fireplace for cozy winter nights; A First floor Laundry room as an added bonus. It's Sun-Kissed Den perfect for relaxing. The icing on the cake is the Bright & Spacious Game Room with Sliders to the backyard, Truly a must see !!!!

26 Winters Lane, Middletown

$688,000

3 Beds ⋅ 3 Baths ⋅ 1044102 MLS

Lot & Natural Setting Generous Acreage & Privacy: Situated on a spacious, private lot surrounded by scenic Hudson Valley greenery, offering peace, quiet, and minimal drive-by traffic. Outdoor Living Potential: Abundant usable yard space ideal for entertaining, gardening, a patio or deck, outbuildings, or potential pool additions. Tranquil Country Atmosphere: Enjoy the feel of a quiet rural retreat while remaining just minutes from suburban conveniences. Location & Commuter Convenience Easy Highway Access: Conveniently positioned with quick access to major transit arteries, including Route 17 (Future I-86) and Interstate 84, making travel across Orange County and into Northern New Jersey or New York City straightforward. Public Transit Options: Short drive to the Middletown Metro-North train station and local coach bus terminals for stress-free commuting. Local Amenities & Services Shopping & Dining Hub: Located just minutes from the Route 211 commercial corridor, including the Galleria at Crystal Run, major retail centers, grocery stores, and local dining. Top-Tier Healthcare: Close proximity to Garnet Health Medical Center and surrounding specialty medical facilities. Recreation & Parks: Quick access to outdoor activities, including nearby golf courses, Highland Lakes State Park, heritage trails, and local farm markets. Ownership Appeal Versatile Property Layout: Offers substantial flexibility for family living, home office setups, guest accommodations, and ample storage or workshop space. Strong Long-Term Value: Well-located in a steadily growing Hudson Valley residential market that appeals to both local buyers and NYC commuters seeking space and tranquility.

151 Bowser Road, Middletown

$670,000

5 Beds ⋅ 3 Baths ⋅ 1046887 MLS

This single-family residence bi-lonial was built in 2007, features 5 bedrooms, and 3 full bathrooms. house is newly remodeled. located on this great dead end road with no through traffic. There's a granite counter tops and cherry cabinetry in the kitchen, a gas fireplace in the living room, large front bay windows. Upper level bring you 3 bed rooms and two pull bathroom. Lower level is finished with family room, another two bedrooms and a full balthroom. Near all amenities and Hwy for easy commuting.

20 3rd Street, Middletown

$469,000

3 Beds ⋅ 3 Baths ⋅ 1043873 MLS

Wow! Move right into this beautiful corner unit in Maple Fields offering plenty of living space, 3 bedrooms, 2.5 baths, a finished basement, and a 2-car garage. Features hardwood floors on the main level, a spacious kitchen with granite counters and ample cabinetry, and comfortable bedrooms with large closets and carpeted floors. The laundry is conveniently located upstairs. The finished basement offers a large family room with plenty of additional space. Enjoy all the amenities Maple Fields has to offer, including a pool, clubhouse, playground, tennis, and more! Conveniently located near shopping and transportation with easy access to major highways.

34 Field Stone Drive, Middletown

$339,000

2 Beds ⋅ 1 Baths ⋅ 1039162 MLS

A cozy and beautifully maintained home in a convenient location, this charming 2-bedroom, 1-bath property offers comfort, character, and thoughtful updates throughout. The updated kitchen and bathroom complement the warm hardwood floors on the main level, while raised dormers upstairs create a more spacious feel. The home features numerous important updates, including the roof, heating and cooling system, plumbing, electrical, appliances, gas hot water heater, front porch, driveway, and back deck. The oversized rear deck is ideal for entertaining or relaxing and leads to the backyard, while the inviting front porch adds to the home’s curb appeal. The basement/garage area offers laundry hookups, a slop sink, workshop space, and ample storage. Conveniently situated with easy access to transportation and everyday amenities, this pretty and comfortable home is a wonderful opportunity for a first-time buyer or anyone looking to downsize. MUST SEE- WON'T LAST!

26 Gardner Avenue, Middletown

$765,000

4 Beds ⋅ 3 Baths ⋅ 1035070 MLS

Timeless Character. Endless Possibilities. Nestled on over 12 private, wooded acres along a quiet country road, this stately brick Colonial offers the rare opportunity to own a home where history, craftsmanship, and natural beauty come together. Built circa 1900 and encompassing more than 3,000 square feet, this remarkable residence is filled with the warmth and architectural character that only a historic home can provide. The classic brick facade, welcoming front porch, and mature landscape create an unforgettable first impression. Inside, oversized windows bathe each room in natural light while preserving peaceful views of the surrounding property. Original details throughout the home—including wide-plank wood floors, handsome millwork, multiple fireplaces, and gracious proportions—reflect the quality and charm of a bygone era. Offering four to five bedrooms and three full baths, the home provides an abundance of living space for everyday comfort and entertaining. The country kitchen captures the home's historic appeal, while formal living areas and generously sized rooms offer flexibility for today's lifestyle. One of the home's most captivating spaces is the stunning four-season family room, where soaring wood ceilings, walls of windows, and a dramatic wood-burning brick fireplace create an inviting retreat in every season. Whether enjoying a quiet morning coffee or gathering with family and friends, this spectacular room is certain to become the heart of the home. Outside, the property continues to impress. Over 12 wooded acres provide exceptional privacy and a peaceful setting without sacrificing convenience. A tremendous bonus is the attached heated three-bay garage with an expansive walk-up loft. Whether you're a car enthusiast, contractor, hobbyist, collector, or simply need room for recreational vehicles, equipment, or a workshop, this versatile space offers endless possibilities rarely found on residential properties. This home presents an exceptional opportunity for the next owner to enhance and personalize a property already rich in history and character. For those who appreciate timeless architecture, generous acreage, and the enduring craftsmanship of a historic home, this is truly a place unlike any other. This home is centrally located just minutes to Middletown, Matamoras, PA and the Otisville Station on the Metro-North Port Jervis Line.

118 Ridge Drive, Middletown

$549,999

4 Beds ⋅ 4 Baths ⋅ 1020924 MLS

Welcome to 19 Davidge Road, where luxury, comfort, and functionality come together in one exceptional home. Nestled in the highly sought-after Presidential Heights neighborhood, this impressive 4-bedroom, 4-bathroom residence offers the perfect blend of elegant living spaces and incredible amenities designed for today's lifestyle. From the moment you enter, you'll be captivated by the soaring vaulted ceilings and spacious open-concept design. The inviting living room features a cozy gas fireplace, creating the perfect atmosphere for relaxing evenings or entertaining guests. The chef-inspired kitchen is a true showpiece, complete with a commercial-grade stove, oversized commercial refrigerator, beautiful cabinetry, and abundant workspace that's ready to impress everyone from the home cook to the culinary enthusiast. Retreat to generously sized bedrooms and beautifully updated bathrooms, while hardwood flooring throughout much of the home adds warmth and timeless elegance. Car enthusiasts and hobbyists will appreciate the attached 2-car garage equipped with two professional vehicle lifts, allowing for indoor parking for up to four vehicles—a rare and highly desirable feature. "Basement, Garage, and 2 Yard photos has been digitally declutterred to show clear space."

19 Davidge Road, 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, Double Oven 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

$714,000

4 Beds ⋅ 3 Baths ⋅ 1029697 MLS

Nestled on 2.5 peaceful acres, this colonial-style home has been lovingly cared for by the same owner since it was built in 2006. The dramatic cathedral ceiling foyer welcomes you with a sense of grandeur, opening to a spacious interior filled with natural light. Hardwood floors flow throughout, enhanced by a refreshed staircase with updated balusters and designer lighting. The custom kitchen is a standout, offering Carrera Gold Silestone countertops, Bosch appliances, custom cabinetry, and a farmhouse sink featuring a built in food disposal. The living room’s cozy setting with fireplace creates the perfect gathering space, and central air ensures comfort all year long. The primary suite is generously sized, featuring two built in closets and a custom walk in closet. A luxurious, spa-inspired primary bathroom featuring floor-to-ceiling marble tile, heated marble flooring and an oversized walk-in shower enclosed in frameless glass. The shower includes a rainfall showerhead, handheld sprayer, multiple body jets, a built-in bench and sleek black fixtures. A Fleurco Opus Collection freestanding soaking tub, premium Kohler bidet toilet, recessed lighting and a large window overlooking the greenery complete this elegant retreat. With new siding, new garage doors, and a new deck, the home blends thoughtful updates with long term care. A truly special property, ready to be treasured by its next owner.

210 Howells Turnpike, Middletown

$599,000

3 Beds ⋅ 3 Baths ⋅ 1021680 MLS

Home sweet home! This beautiful custom built three bedroom, two and a half bathroom 2086sqft ranch is located on a gorgeous landscaped 5 acres in the Minisink Valley School District. You'll feel right at home from the moment you enter this park-like property. You have many choices of places to enjoy this home, both inside and outside. The 1900sqft main floor is open and spacious. The central great room features 17 foot cathedral ceilings, mini-split AC and heat, ceiling fan, large windows letting the sunlight in, and two separate doorways to the large back deck. Enjoy peace and quiet on a beautiful day on your oversized back deck. Have a campfire with some friends and family by the fire pit. The recently renovated kitchen features new appliances, quartz countertops and tile backsplash. The primary bedroom suite is on one side of the house with two large closets and a large beautiful en-suite bathroom. Bedrooms two and three are on the other side of the house along with another full bathroom. Walk up to the spacious loft on the second level, which could have many uses. Renovated within the past 3 years with a new roof, new deck and deck stairs, sidewalk deck to driveway. Recently painted kitchen, great room, loft and master bedroom. Very well maintained home and property. Whole house generator. Mitsubishi Mini-split AC cooling and heating. The huge full basement is the size of the home providing plenty of storage and workshop space. 2 Car attached garage. Plenty of room for guests with a parking area by the front of the home, and a large parking area in the rear. Wood or oil combination furnace for baseboard heating, mini split for AC and for heat.

189 School House Road, Middletown

$795,000

4 Beds ⋅ 3 Baths ⋅ 1017645 MLS

Seller ready to go! This stunning four-bedroom Colonial is nestled on 1.3 acres at the end of a peaceful cul-de-sac, backing up to the scenic Hunter Nature Preserve. Solar panels owned, utility bills less than $25/month. Enjoy relaxing evenings on the spacious rocking chair front porch. The updated kitchen features beautiful granite countertops and a custom backsplash, perfect for culinary enthusiasts. The expansive Great Room is ideal for celebrations, entertaining guests and marking life's special milestones. A formal dining room provides the perfect setting for holiday dinners, while both the family room and living room offer quiet retreats at the end of the day. The primary bedroom includes a private bathroom plus a plentiful walk in closet. You'll find three more generously sized bedrooms and a full second bathroom. A strategically placed home office at the top of the stairs is perfect for remote work or tackling paperwork. Step outside to a back deck with an awning for shaded relaxation, overlooking a spacious yard. Enjoy the heated inground pool, perfect for lap swimming and relax in the heated jacuzzi. Host gatherings on the backyard deck or paver patio designed for outdoor entertaining. The attached two car garage comes equipped with a charger for your electric vehicle. . Located in the desirable Minisink Valley School District, this gorgeous home truly offers something for everyone. Don't miss your chance to experience all this property has to offer. Schedule a visit today!

34 Stapleton Court, Middletown

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