$368,302Average Value$247Average Price per Sq Ft82Homes For Sale
Revitalized city offers convenience outside of NYC
Located in New York’s Hudson Valley, just 60 miles from the outskirts of Upper Manhattan, Middletown offers suburban charm in an up-and-coming city of around 30,000 people. Dating back to 1848, Middletown showcases a variety of historic housing styles that cast the city as an established municipality – and over the years has grown to be the largest city within Orange County.
The city’s largest employers include the Garnet Health Medical Center, Crystal Run Health and Access: Supports for Living. Known as the Business Improvement District, Middletown’s downtown area has been transformed into a budding epicenter for shopping, dining, and entertainment thanks to a $10 million Downtown Revitalization Initiative grant awarded by the state. “The city has undergone a tremendous change from a small town to a big city,” says Dulce Ferrera, a principal broker at Keller Williams Realty Hudson Valley United who’s lived in the area since 1986. “Everything is available, from shopping malls to entertainment, all within a friendly, family-oriented community.” Today, Middletown thrives as a destination for local commerce, unique dining experiences and active community events, pulling a growing population to the Hudson Valley.
Crawford, NY is a bucolic neighborhood north of Middletown and Goshen.
Wallkill neighborhoods vary from rolling, rural farmland to dense, neighborly suburbs.
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Mix of historic and traditional homes
Historic homes are scattered between renovated buildings that house apartments and condos. There is an eclectic mix of architectural styles on the outskirts of town, including Colonial Revival, Cape Cods and split-level homes on gentle hills. As subdivisions continue to grow, new traditional and contemporary styles have become more popular. “There is little inventory within a tight market,” Ferrera says. “And it’s common for homes to sell over asking price.” The median price for single-family homes is $395,000, which is lower than the $418,700 national median reported by the National Association of Realtors.
Wallkill's various neighborhoods feature many split-level Colonial Revival homes.
There are many smaller Cape Cod style houses in Waywayanda.
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Bustling downtown district with local stores and restaurants
Downtown Middletown is the area's central business district. The walkable, mixed-use district houses restaurants and shops, mostly along North Street, South Street and Main Street. Popular local eateries include Oak & Reed, with its seasonal American dishes, and Piccolo Cucin e Vino, with its Italian favorites. Downtown is also saturated with microbreweries, cafes, specialty shops and boutiques. The Galleria at Crystal Run mall has big box stores, as well as a bowling alley, movie theater, and Urban Air Trampoline and Adventure Park.
Clemson Bros. Brewing in Middletown offers up delicious food alongside their ales and IPAs.
For records, memorabilia, band merch and more, you have to check out Rock Fantasy in Middletown.
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Hiking trails and attractions close to town
Middletown holds 14 parks and green spaces, giving residents quick access to outdoor recreation. Just minutes from downtown, the recently opened Middletown Reservoir Trails has 8 miles of paths winding throughout the 1,250-acre watershed. Highland Lakes State Park is a 3,000-acre tract of woods and lakes that's open for hiking and fishing. Attractions outside of Middletown are also a draw for residents. “You can get to Legoland in Goshen, casinos and resorts, or the Mohonk Mountain retreat for skiing all within 20 minutes,” Ferrera says.
The historic Paramount Theatre, built in 1929, is a 1,100-seat theatre that’s a cornerstone of entertainment for the city, hosting everything from movie screenings to community plays. Colorful lights illuminate the classic bowling lanes at Quinnz Pinz. The venue hosts live music performances regularly, making it a popular weekend spot.
Wallkill locals come to Highland Lakes State Park to walk the trails, fish and bowhunt.
Circleville Park has long winding trails and walking paths for Wallkill residents.
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Long-standing Orange County Fair and newer events
Downtown Middletown is also the epicenter of community events, including the weekly farmers market every Saturday at Erie Way Park from June to October. In the warmer months, the city hosts a Summer Concert Series, showcasing local and regional artists every Thursday and Friday night. Middletown is also home to the Orange County Fair, one of the oldest fairs in New York. The Orange County Fair Speedway started as a horse racing track before it was converted into a speedway. Now, the clay track holds races every Saturday from April to September. And to kick off holiday celebrations in the winter, the downtown district puts on an annual Tree Lighting Parade and Celebration at Festival Square.
The Orange County Fair in Wallkill is a popular outing for local teens and families.
The Orange County Fair is a treasured annual tradition in Wallkill, NY.
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Academy programs at Middletown High School
The Enlarged City School District of Middletown consists of seven public schools and gets a B-minus from Niche. Middletown High School earns a B and offers the national Academy Foundation program, featuring STEM and industry-specific curricula in four main categories: engineering, finance, health and sciences, and information technology. Middletown is also home to the C-rated Orange County Community College and the Touro College of Osteopathic Medicine - Middletown Campus, currently unrated by Niche.
Middletown High School is an above average, public school located in Middletown, NY. It has 2,523 students in grades 9-12 with a student-teacher ratio of 13 to 1.
Middletown High School offers a variety of sports and academic programs.
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Close to I-84, buses to Manhattan available
U.S. Route 211 cuts through Middletown and links to Interstate 84 and NY State Route 17, connecting residents to neighboring communities and New York City. Commuters can also use Transit Orange bus routes that run throughout Middletown and connect to the Port Authority Bus Terminal in Manhattan. The Garnet Health Medical Center is located 3 miles east of downtown, and New York Steward International Airport is just 20 miles east.
According to data reported to the FBI, violent crime increased by 22% and property crime increased by 20% from 2022 to 2023. Overall, reported crime rates in Middletown are comparable to state and national averages.
Written By
Logan Soter-Reardon
Photography Contributed By
John Gallino
Video By
Victoria Sharpe
Interested in learning more about homes in this area?
Reach out to
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GreatSchools:
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On average, homes in Middletown, NY sell after 61 days on the market compared to the national average of 53 days. The median sale price for homes in Middletown, NY over the last 12 months is $399,000, up 4% from the median home sale price over the previous 12 months.
Stunning New Construction colonial on a dead end street. Welcome to your dream home set on 3 picturesque acres in the Town of Greenville, within the highly sought-after Minisink Valley School District. The Oakwood model is nestled on a private, partially wooded lot at the end of a quiet cul-de-sac, offering the perfect blend of style, comfort, and functionality. Step inside to find 4 spacious
Middletown Gem: Updated Home, Unbeatable Location, Finally Priced Right. Welcome to 70 miles of freedom from NYC with none of the sacrifice. This thoughtfully updated Middletown home sits in one of Orange County's most connected communities, where Metro-North train access and major highway proximity put Manhattan within easy reach while keeping you rooted in the peace and affordability of Hudson
Looking for one-story living in a private dead end street, look no further as you have found it! Beautiful hardwood floors welcome you into a living room with plenty of window light followed by an eat-in kitchen that has been fully equipped with gorgeous stainless steel appliances, new counters and plenty of cabinet space. Three spacious bedrooms with plenty of closet space and a beautiful tiled
Don’t miss this 4-bedroom, 2-bath Colonial located in the City of Middletown near Touro College and downtown amenities. including eateries, shopping and local amenities. Featuring generous living space and a traditional Colonial layout, this property offers strong potential for owner-occupants or investors alike. Plenty of parking. Close to dining, shopping, transportation, and schools, this is a
Stunning New Construction colonial on a dead end street. Welcome to your dream home set on 3 picturesque acres in the Town of Greenville, within the highly sought-after Minisink Valley School District. The Oakwood model is nestled on a private, partially wooded lot at the end of a quiet cul-de-sac, offering the perfect blend of style, comfort, and functionality. Step inside to find 4 spacious
Middletown Gem: Updated Home, Unbeatable Location, Finally Priced Right. Welcome to 70 miles of freedom from NYC with none of the sacrifice. This thoughtfully updated Middletown home sits in one of Orange County's most connected communities, where Metro-North train access and major highway proximity put Manhattan within easy reach while keeping you rooted in the peace and affordability of Hudson
LG PRICE REDUCTION FOR FASTER SALE...OWNER RELOCATING OF THIS Amazing Mini Mansion Luxury Hse on this one ! For those that look for the very best and finest that the Hudson Valley has to offer you are sure to be amazed as you enter this 11200 plus sq ft luxurious brick colonial mansion including 3200 sq ft Indoor Pool room ! Yes you read that correctly, this home is one of the very few that
Welcome to 22 Sharon Drive in Middletown, a well-maintained raised ranch offering space, comfort, and a highly convenient location. The main level features hardwood floors throughout, a large living room with high ceilings, and an expansive dining area ideal for everyday living and entertaining. The kitchen is finished with granite countertops and offers great functionality. The upper level
This bright and spacious third-floor corner condo in the sought-after Deer Run community offers two bedrooms and two full baths with an open floor plan ideal for both everyday living and entertaining. Sunlight streams through a wall of windows into the combined living and dining area, while the kitchen provides abundant cabinetry and a generous pantry. The primary suite features a large walk-in
Welcome to this nearly new four-bedroom, three-bath ranch-style home, nestled on a picturesque two-acre, tree-lined lot that offers both privacy and natural beauty. With stucco siding and a thoughtfully designed layout, this home combines modern comfort with timeless appeal.Step inside to find a spacious, open-concept floor plan with abundant natural light. The main living areas flow
Luxury Living in Hamptonburgh. Nestled in the prestigious Windsor Estates enclave, within the sought-after Goshen School District, this exceptional Contemporary residence offers a rare blend of elegance, comfort, and convenience. With nearly 3,500 sqft of thoughtfully designed living space, this striking home features 4 spacious bedrooms, 3 bathrooms, and a 3-car garage. Step into a grand
Welcome to 171 High Barney a charming three-bedroom, two-bath home tucked away on a quiet dead-end street just before the cul-de-sac. This inviting property offers a bright, cozy living room and a modern kitchen equipped with stainless steel appliances, quartz countertops, and plenty of cabinet space. The lower level features a spacious family room along with bonus space ideal for a home office,
Well maintained 3 bedrooms, 2 bathrooms mobile home in the Valley View mobile home community.Simple one level living, short distance from major highways and shops. Located in the Valley Central School District. Very easy to see. Call today for your own private tour.
Warmth, comfort & space in the Hudson Valley. Welcome home to this spacious Colonial on 2.8 acres offering 3–4 bedrooms, 2 full baths, and a detached 2-car garage with oversized loft. The heart of the home is the large family room — cathedral ceilings, a stunning stone fireplace, and beautiful hardwood floors — the perfect place to gather. The private second-floor primary suite has its own full
Spacious 3BR/1BA Second-Floor Unit. Bright and nicely updated second-floor unit featuring 3 bedrooms and 1 bathroom. Enjoy a sunny eat-in kitchen, fresh paint throughout, and newer hardwood flooring. Additional attic space included, attic space is ONLY for storage use. Located in a quiet neighborhood just a short distance from parks, the YMCA, shops, commuter trains, and bus lines. Tenant pays
Beautifully renovated upstairs apartment featuring two bedrooms and one bathroom. An additional room offers the perfect space for a home office. This rental includes a cozy kitchen, a comfortable living room, and an oversized laundry room. Upstairs, you’ll find a storage area (not permitted for sleeping purposes). Two parking spaces are designated for tenant use, and a back patio provides a nice
Experience Modern Living in a Brand-New 2-Bedroom Apartment. Take advantage of this rare opportunity to move into a newly constructed 2-bedroom apartment, thoughtfully designed with high-end finishes and modern conveniences. Enjoy a welcoming open floor plan that features a stunning kitchen complete with Quartz countertops and brand-new, energy-efficient stainless steel appliances. Oversized
This gorgeous rental is move-in ready and beautifully updated throughout. The kitchen features numerous upgrades, including granite countertops with a complementary backsplash, stainless steel appliances, and an abundance of crisp white cabinetry. There is also space for a table and chairs—perfect for casual meals. The home offers brand-new flooring and fresh paint throughout. Enjoy year-round
Experience this beautifully renovated two-bedroom, one-and-a-half-bath townhouse in Water Edge, Middletown. Step inside to find brand-new kitchen appliances, stunning new hardwood floors, and fresh paint throughout. The updated bathrooms feature modern vanities that add a stylish, elegant touch. Enjoy the added convenience of an in-unit washer and dryer.Ideally located just across from serene
Welcome to this beautiful Victorian-style rental, centrally located in the heart of Middletown, NY. From the moment you arrive, the charming wrap-around porch sets a warm and inviting tone, perfectly complementing the home’s classic character. Inside, you’ll find an updated interior featuring a modern kitchen, a brand-new central air system, new windows, and new doors, providing both comfort and
Experience Modern Living in a Brand-New 2-Bedroom Apartment. Take advantage of this rare opportunity to move into a newly constructed 2-bedroom apartment, thoughtfully designed with high-end finishes and modern conveniences. Enjoy a welcoming open floor plan that features a stunning kitchen complete with Quartz countertops and brand-new, energy-efficient stainless steel appliances. Oversized
The brand new residences at Southgate Middletown offer a community feel in the center of rapidly growing Middletown, N.Y. Here, an amenity-rich lifestyle awaits, with beautiful homes that feature only the finest in custom appointments and design. See for yourself how easy it would be to call Southgate home. The style of Southgate living features soaring 9-foot ceilings, exquisite luxury flooring,
Now available at 31 Beattie Ave, Apt #2 in Middletown, this well-maintained upstairs apartment offers a bright, comfortable layout in a residential neighborhood. The unit features tenant-paid gas heat and electricity, allowing you to manage your own utility costs, and includes off-street parking for added convenience. Located close to local shops, dining, and major roadways, this apartment
Slatewood Apartments offers a great mix of convenience and serenity, with its wooded setting providing a peaceful environment while still being close to essential amenities. The proximity to the new state-of-the-art Medical Center is a particularly nice touch for residents who might need easy access to healthcare services. With options for one-, two-, and three-bedroom apartments, it caters to a
This two story home has so much to offer. On the first floor there is a bright and sunny living room, dining room, full bathroom and kitchen with stainless steel appliances. Upstairs there are three good sized bedrooms and another full bathroom. There is a nice level yard and driveway parking. This home is close to all shops, restaurants, schools, public transportation and highway access.
Welcome to Country Manor Apartments in Middletown, NY! Tucked into a peaceful suburban neighborhood, our pet-friendly community offers spacious and thoughtfully designed one- and two-bedroom homes perfect for every lifestyle.Your rent includes heat, hot water, gas, and trash removal— making your living experience simple and stress-free. We offer onsite laundry, high-speed internet access,
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