$412,027Average Value$229Average Price per Sq Ft12Homes 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.
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.
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
Tyler Newbold
Interested in learning more about homes in this area?
Reach out to
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On average, homes in Middletown, NY sell after 59 days on the market compared to the national average of 70 days. The median sale price for homes in Middletown, NY over the last 12 months is $420,000, down 12% from the median home sale price over the previous 12 months.
Nestled on 1.5 park like acres with lots of privacy in the back, built in 1969 and lovingly cared for by the same family for over 56 years is this unique front back split level with four levels in the home. Step through the front door to find a half bath, home office with lots of shelving already in place, and second room used as a craft room, play room,or additional home office conveniently
Step into this fully updated, move-in ready luxury condo located in one of the area’s most sought-after gated communities. This stunning first-floor residence has been meticulously upgraded from top to bottom—featuring designer finishes, fresh modern paint tones, and premium luxury flooring throughout. The custom kitchen is outfitted with elegant cabinetry, granite countertops, and stylish
Welcome to the perfect blend of comfort, character, and location. Nestled in the vibrant heart of Middletown, NY—just 70 miles from NYC—this beautifully updated home offers a peaceful retreat without sacrificing proximity. Whether you’re commuting for work or play, nearby transportation options, including the Metro-North train and major highways, make travel to the city a breeze. And when you're
Nestled on 1.5 park like acres with lots of privacy in the back, built in 1969 and lovingly cared for by the same family for over 56 years is this unique front back split level with four levels in the home. Step through the front door to find a half bath, home office with lots of shelving already in place, and second room used as a craft room, play room,or additional home office conveniently
Step into this fully updated, move-in ready luxury condo located in one of the area’s most sought-after gated communities. This stunning first-floor residence has been meticulously upgraded from top to bottom—featuring designer finishes, fresh modern paint tones, and premium luxury flooring throughout. The custom kitchen is outfitted with elegant cabinetry, granite countertops, and stylish
Welcome to the perfect blend of comfort, character, and location. Nestled in the vibrant heart of Middletown, NY—just 70 miles from NYC—this beautifully updated home offers a peaceful retreat without sacrificing proximity. Whether you’re commuting for work or play, nearby transportation options, including the Metro-North train and major highways, make travel to the city a breeze. And when you're
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 spacious 2-bedroom apartment is located in the center of Middletown. Featuring a bright open-concept layout from the living room to the kitchen, this home is designed for both comfort and style. Enjoy high ceilings with recessed lighting, ductless A/C and heating, and brand-new flooring throughout. The kitchen shines with new stainless steel appliances, fresh cabintry, and granite
Located on the first floor, this well-maintained 2-bedroom, 2-bathroom rental offers comfortable living in a sought-after community. The bright and welcoming kitchen features a brand-new stove with a three-year old microwave, an adjoining dining area—perfect for everyday meals or entertaining. Down the hall, you’ll find two spacious bedrooms, including a primary suite with a private full bathroom
The Town of Crawford is a small farming community in New York that would be easily overlooked if it wasn’t for the hamlet of Pine Bush, which claims to be the UFO capital of the East Coast. Residents take pride in its folklore, which attracts UFO fanatics every June for the annual Pine Bush UFO Fair & Parade and weekenders looking to explore The Pine Bush UFO & Paranormal Museum. “You hear stories of people who have had sightings and people who have not,” says Marion Bruhns, a resident and top-producing associate broker with Howard Hanna Rand Realty. “But one of the most salient features is the friendliness – people are gracious and kind, and it’s just a relaxed atmosphere. The ease of living is what people looking to escape the city want.” Bordered by the scenic Appalachian Mountains to the west and the Hudson River to the east, Crawford offers a rural lifestyle where strange encounters are common talking points, and the mysteries hidden amongst the great outdoors are a stone’s throw away.
The annual Pine Bush UFO Fair & Parade is the largest event in town. “I attended the last one,” Bruhns says. “People come from all over. It’s one of the main draws that attracts visitors from across the nation.” Every June, Main Street Pine Bush reflects a scene from outer space, with patrons turned into extraterrestrial beings from across the galaxy. Apart from tinfoil hats, creative ensembles and costume contests, patrons of all ages can enjoy a range of games, live music, and eclectic craft and food vendors. Before the event, locals can brush up on the latest paranormal and UFO news and win a prize during trivia. “Hudson Valley still has its dose of culture, art events, and many things to offer,” Bruhns says. Alien talk is replaced with art during annual events like Fall Art Walks, Art in the Square, and Pine Bush’s First Fridays, where locals can peruse artists’ studios from May to December. Its breathtaking landscape has attracted artists like Bruhns throughout the years. “We’re also not too far from where the Hudson River School was, which was a haven for painters in the 19th century,” Bruhns says.
Located approximately 75 miles from New York City, winding country roads give way to swaths of farmland and sparse residential streets. Pockets of dense residential development are primarily found in the heart of Pine Bush, where styles range from single-family dwellings to townhouse complexes along Boniface Drive. The latter has units priced from the low $200,000s to $300,000. Other properties, often on large lots, include a mix of bi-levels and ranch-style homes that range from the mid $200,000s to the high $400,000s. Contemporary homes and colonials can sell from the $500,000s to the $900,000s, with properties on acres of land selling for over $1 million. “The newer builds out here are spectacular with interesting contemporary designs. Or they’re made to blend in with the quaint historic homes,” Bruhns says. Homebuyers should note that nearby streams are prone to localized flooding, and nearby woodlands pose a seasonal wildfire risk.
Bordered by the Appalachian Mountain Range to the west, miles of hiking trails are easily accessible just 10 miles away. Hudson Valley also has many sleepaway summer camps for kids, like Camp Echo and equestrian facilities. Highland Lakes State Park offers even more trails, and those who prefer a stroll can explore the 2-mile Crawford Walking Trail in the heart of town. Pine Bush Town Park is the community’s crown jewel, boasting multiple sports fields like baseball diamonds, pickleball courts, a playground, and picnic pavilions. Nearby Winding Hills County Park is a relaxing weekend getaway with campgrounds, wooded trails, and a 40-acre lake open to anglers and car-top boaters. In winter, locals can ice skate or fish along the water. Right down the road is Winding Hills Golf Club, a members-only course open seven days a week.
The Pine Bush Central School District serves the Crawford community, scoring average ratings on Niche. Students are split between the C-plus-rated E.J. Russell Elementary School and the C-rated Pine Bush Elementary School. Middle schoolers may attend Crispell or Circleville, both scoring a C-plus, and Pine Bush High earns a B. The latter offers Advanced Placement courses and a range of extracurricular activities, like Pine Bush’s Odyssey of the Mind team, which won second place at the Worlds competition in 2024. Locals are also just 12 miles from SUNY Orange County Community College in nearby Middletown.
Local spots like The Cup & Saucer Diner showcase themes from outer space, serving up out-of-this-world American classics in a retro atmosphere. Pine Bush Deli and Pizza is one of the few pizza joints around town, and summer evenings lead to crowds at Hometown Ice Cream and Grill. Bistro Du Mexique is a local favorite, offering a fusion of French and Mexican flavors. Angry Orchard Cider House, a nationally recognized brand, offers fun weekend outings with scenic views of its 60 acre apple orchard just 7 miles away. “You don’t have to leave town for anything,” Bruhns says. “We have restaurants, shops and grocery stores. You can pump your gas at Stewart’s and pay at the counter afterward.” Weekly essentials are found at stores like Hannaford, Dollar General, and Tractor Supply Co. Seasonal produce is available at the Pine Bush Farmers Market on Saturday mornings. About 11 miles away, Middletown has many big box retailers and shopping malls like the Galleria at Crystal Run.
The ShortLine Hudson bus route runs along nearby New York State Route 17, and Dial-A-Ride service is available, but Crawford is extremely car-dependent overall. State routes 302 and 52 are essential arteries in town, along with nearby Interstates 84 and 87. New York Stewart International Airport is about a 17 mile drive along New York State Route 17K, and Orange Regional Medical Center is the nearest hospital, approximately 12 miles south in Middletown. With New York City about 75 miles away, residents have about a 2 hour commute via Middletown’s train station or car.
Around Crawford, houses of worship cater to diverse congregations that range from Christianity to Hinduism to Islam in nearby Middletown. Hudson Valley is also home to numerous Buddhist monasteries and centers due to its proximity to New York City, where themes of meditation and mindfulness flourish, and its access to natural beauty. Nearby spots include the Dharma Drum Retreat Center, about 6 miles northwest, and Blue Cliff Monastery, about 8 miles northwest.
It's sometimes confused with a small farming hamlet with the same name that’s about 17 miles away, but the town of Wallkill, encircling the city streets of Middletown and on the cusp of forests and farmland, blends city and country living. Due to its proximity to Middletown, Wallkill offers residents a mix of big-box stores and upscale eateries, as well as tranquil country roads and untouched nature reserves. “Middletown is the hub of Hudson Valley, and parts of Wallkill share the same zip code,” says Gail Rachlin, a Realtor with Keller Williams Hudson Valley United who has over 20 years of experience. “It’s also a much more desirable and upscale community than surrounding towns.” New subdivisions with large homes are common due to a growing destination for commuters seeking a slower pace of life, with a nearby train station and New York City just 75 miles away.
Hamlets within Wallkill like Scotchtown and Mechanicstown feature traditional residential streets where homeowners can greet their neighbors in passing. These properties typically feature modest lots with a mix of bi-levels, colonials and ranch-style homes priced from the $200,000s to the $400,000s. Mobile-home communities are clustered along New York State Route 211 and sell in the $100,000s. Townhouse complexes are also scattered around town, with units ranging from the $200,000s to the $500,000s. Contemporary homes and spacious New Traditional houses with colonial influences typically sit on larger, secluded lots. Properties can range from the $500,000s to over $1 million, with modern log cabins and historic farmhouses scattered in between. Homebuyers should also note that localized flooding and wildfire risk are possible given the community’s proximity to waterways and forested areas.
Small neighborhood parks and massive forested reserves make up Wallkill’s landscape. Community parks include Howard Drive, home to a playground and baseball diamonds that attract kids and Little Leaguers, and Dundee Circle Park, another small green space with a playground and picnic area. The 7-acre Henneside Lake awaits anglers at Circleville Park and is a popular spot for pedal boats and swimmers. The park is also home to the Town of Wallkill Boys & Girls Club, which holds after-school activities and summer camps for kids. Five miles from Circleville Park, Highland Lakes State Park offers over 3,000 forested acres for fishing, hiking and horseback riding. Locals can also explore scenic views along the Middletown Reservoir Trail. Golfers can play at Wallkill Golf Club or West Hills Country Club.
Most amenities are clustered in and around Middletown, including houses of worship that range from historic churches to synagogues and Islamic centers. Strip malls, restaurants and grocers like ShopRite and Walmart Supercenter line both sides of New York State Route 211, known by residents as Miracle Mile. Locals can stock up at Sam’s Club or find numerous retailers at the Galleria at Crystal Run. Nearby eateries range from popular pizza joints like Cosimo’s Brick Oven to Viva Bandido Mexican Restaurant. A few miles west, Middletown has even more breweries and upscale restaurants like Oak & Reed. About 7 miles northwest along New York State Route 17, rural roads give way to small stores like Quickway Diner and Twin Cone, which attract crowds on summer evenings. “There’s still some beautiful horse and dairy farms nearby,” says Marion Bruhns, a Pine Bush resident and top-producing associate broker with Howard Hanna Rand Realty. On the cusp of this farmland, Wallkill's location allows residents to enjoy organic farm markets, orchards and wineries.
Five different school districts serve the town of Wallkill. The Enlarged City School District of Middletown and Pine Bush Central School District encompass the largest residential areas, and each scores an overall B-minus on Niche. Students may start at the C-rated Pine Bush Elementary or the C-plus-rated Circleville Elementary School. Circleville Middle also scores a C-plus, while Pine Bush High School earns a B and offers a range of Advanced Placement courses. SUNY Orange Community College partners with surrounding high schools to offer dual enrollment programs.
Wallkill is home to the Orange County Fair, which has been held for over 100 years. Live performances and entertainment acts like Anastasini Circus take center stage every summer. There’s also a petting zoo, a roller coaster, carnival rides and games. Locals can end their nights enjoying firework displays while digging into a hot funnel cake topped with powdered sugar. When the fair isn’t happening, the Orange County Fair Speedway entertains racing fans. LEGOLAND New York Resort is only 12 miles away in neighboring Goshen, and for evenings at a slower pace, residents can head north along quiet, country roads to catch a movie at the Fair Oaks Drive-In.
Some neighborhoods feature paved sidewalks for afternoon strolls around the block, but Wallkill is primarily car-dependent. Public transit includes shuttle buses that run throughout the workweek and Dial-A-Ride services that require reservations ahead of time. Interstate 84 or New York state Route 17 can be used to get to Orange Region Medical Center, also known as the Garnet Health Medical Center. About 5 miles from the heart of Wallkill, Middletown is home to the closest train station. New York City is approximately a 75-mile drive via U.S. Route 6 or a 1.5-hour train ride.
Property Mix - Square Feet
Middletown Has More Renters
Demographics
Total Population
30,579
Median Age
37
Population under 18
25.9%
On par with the national average
23.8%
Population over 65
14.8%
On par with the national average
19.1%
Finances
Median Household Income
$62,660
Below the national average
$71,702
Average Household Income
$85,458
Education and Workforce
High School Graduates
85.4%
College Graduates
19.1%
Below the national average
34.1%
Advanced Degrees
7.2%
Below the national average
13.3%
% Population in Labor Force
63.2%
Weather
Annual Precipitation
41''
Average Winter Low Temperature
17°F
Average Summer High Temperature
83°F
Annual Snowfall
33''
Area Factors
Somewhat Bikeable
Bike Score®®
42/ 100
Very Walkable
Walk Score®®
89/ 100
Source: Walk Score
Source: Walk Score
Walk Score® measures the walkability of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address. CAP Index provides objective, accurate, and consistent data to help measure, compare, and mitigate crime risks.
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. Our sources include: Accuweather, Public Records and Neustar. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.