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
Frank Tangredi,
an experienced agent in this area.
On average, homes in Middletown, NY sell after 65 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 $397,000, up 5% from the median home sale price over the previous 12 months.
Almost new Townhome in Maples Field is waiting for you! Welcome to our Spacious 3 bedroom, 2.5 bathroom home with 3 levels of space! Enter the open floor plan with hardwood flooring, sun filled living room and dining area. The kitchen features oversized cabinetry with granite countertops, stainless steel appliances and a center island that is perfect for entertaining! Step onto the lovely patio
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
Stunning 37 Wisner Ave. Experience is gorgeous colonial home located in one of the nicest residential neighborhoods in Middletown. This wonderful home is completely Redone in the finest materials and is a 3-4 Bedroom home that features Harwood Floors throughout the first floor. Open, Airy sun drenched Floor plan. Large Living Rm, Formal Dining Rm, Brand New Open Gourmet Designer Kitchen with
Motivated seller. This corner penthouse suite is move-in ready and located in Middletown School District. The kitchen has newer appliances, a new microwave, a pantry and plenty of storage cabinets. With an open concept Livingroom and Dining Room with a wall mounted TV, this suite provides ample room for family gatherings, relaxing and entertainment. The main bedroom boasts a large walk-in closet
Charming ranch-style home is on the market for the first time! A rocking chair front porch welcomes you home, setting the tone for the warmth and comfort you'll find inside this well-maintained 2-bedroom, 1.5-bath that offers true one-level living with laundry on the main floor. Spacious living and dining area filled with an abundance of natural light, and cozy wall-to-wall carpet. This
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
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
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
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