$506,920Average Value$267Average Price per Sq Ft29Homes For Sale
Montgomery offers semi-rural quiet and highway access to New York City
Embedded within rural Orange County, the village of Montgomery offers small-town conveniences and the quiet that comes with the exurbs while still enjoying highway access to New York City. “Montgomery has a rural feel compared to the rest of our area,” says Brian Caplicki, a Realtor with Keller Williams Realty Hudson Valley United who has sold several homes in Montgomery. “There are still farms around, and it’s not quite suburbia. We’re still a bedroom community, though, and lots of people move here from New York City after they have kids.” Just over 23,000 people call Montgomery home, and recently established banks, restaurants and other retail outlets join long-running farm supply companies in offering small-town employment opportunities. Further growth is also in store for this growing New York exurb. Montgomery is currently undergoing two economic development programs aimed at improving downtown's walkability, the expansion of commercial zoning and opportunities and the revamping of the local park.
The heart of Montgomery features shops, churches, homes, and restaurants along quiet streets.
Flags wave over downtown Montgomery, marking the heart of the city’s landscape.
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Victorian homes mix with brand-new builds
Montgomery has a diverse housing stock that includes Victorian homes from the 1860s and new properties built in 2024. “The historic nature of the village is really nice; it’s got that old vibe to it,” Caplicki says. Townhouses sell for between $240,000 and $340,000, while single-story homes go for between $330,000 and $550,000 and two-story and split-level homes sell between $360,000 and $880,000. New Traditional homes built on Montgomery's outskirts from the 1990s to 2020s mostly sell for between $510,000 and $1,150,000. Montgomery’s median sale price of $512,000 is well below the averages of suburbs closer to New York like New Rochelle and Bronxville, where the median sale prices are $800,000 and $699,000, respectively. This lower-than-average cost of housing gets homebuyers a quiet suburban atmosphere, with homes along grid-patterned streets, abundant foliage, sidewalks and quick access to everyday necessities.
Homebuyers in Montgomery often choose historical Victorian houses for their timeless appeal.
New traditional homes in Montgomery feature porches with steps leading to welcoming entries.
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Montgomery has a small, but historic downtown shopping area
Despite its small size, Montgomery has a large and varied shopping scene. “It’s a historic little village with a lot of old buildings and great restaurants,” Caplicki says. “It’s not huge, but it’s cute.” At the intersection of Clinton and Union Streets, around a dozen restaurants serve dishes from around the world. Copperfields Kildare Pub offers an authentic Irish pub experience with vintage architecture, its hanging inn sign bearing County Kildare's coat of arms and a menu of Irish-American staples like fish and chips and corned beef sandwiches. Across the street, PBF Café offers a unique brunch menu including Polish and Brazilian fusion dishes. In the village’s southern outskirts, Mike’s Deli & Pizza has served bagels, sandwiches and pizza for more than 20 years. ShopRite is located just off Interstate 84, 2 miles from downtown.
Flags wave outside PBF Cafe in Montgomery’s historic downtown district.
Fresh coffee and market goods await at Java Blue in downtown Montgomery.
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Valley Central High offers diverse extracurriculars like STEM clubs
Students may start their education at Montgomery Elementary School, which receives a B rating from Niche, before attending Valley Central Middle School and Valley Central High School, which receive B-plus ratings. Valley Central High School includes global citizenship in its mission statement, and programs like the NYS Seal of Biliteracy, the Volunteer Club of Valley Central and the HOSA Future Health Professionals club give students chances to sharpen their skills.
Valley Central High School in Montgomery is rated B-plus by Niche.
Valley Central Middle School in Montgomery welcomes students each morning.
Montgomery Elementary School receives a B rating from Niche.
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Montgomery is surrounded by a wealth of outdoor activities
Located at the center of town, Veterans Memorial Park includes five baseball fields, pickleball and basketball courts and a small dog park with agility equipment. The Wallkill River, which runs past this park and downtown Montgomery, is often utilized for kayaking. Summertime sees the Clinton Street Bandstand in downtown Montgomery host several concerts from July to September. Montgomery is also close to the Winding Hills County Park, situated along the village’s western outskirts. This park includes hiking trails that connect campgrounds and lead to a 40-acre lake open for boating and fishing from May to October and ice fishing during the winter months. The Winding Hills Golf Club sits across the street from the park, and its 18-hole executive golf course is open to the public. Golfers also live just around the corner from Scott’s Corners Golf Course to the northeast and The Country Club at Otterkill to the southeast. South of Montgomery, the Orange County Arboretum makes 35 acres of flora available for exploration, including a remembrance walkway and garden commemorating the county’s 44 residents who lost their lives on 9/11.
The playground at Veterans Memorial Park in Montgomery draws families and kids on sunny afternoons.
The Wallkill River, a popular spot for kayaking during the summer months, is easily accessible from Benedict Farm Park in Montgomery.
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Highway access to NYC
Interstate 84 runs past Montgomery and connects this village to several other major highways, including those leading to Manhattan, 75 miles to the south. Many Orange County residents commute into New York City for a handful of workdays while working from home the rest of the week. Montgomery is also 10 miles up Interstate 84 from the Garnet Health Medical Center in nearby Middletown.
Written By
Jacob Adelhoch
Photography Contributed By
Kellan Beaver
Video By
Jason Jacot
Interested in learning more about homes in this area?
Reach out to
Linda Majetich Hansen,
an experienced agent in this area.
GreatSchools:
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On average, homes in Montgomery, NY sell after 57 days on the market compared to the national average of 58 days. The median sale price for homes in Montgomery, NY over the last 12 months is $497,500, down 2% from the median home sale price over the previous 12 months.
Nestled within the sought-after Winding Hills Estates, this exceptional home is set on a quiet cul-de-sac and backs directly to the rolling greens of the picturesque Winding Hills Golf Course, an executive 18-hole course surrounded by manicured landscaping. From the moment you arrive, the home impresses with Hardie board siding, a metal roof, blacktopped driveways, paver walkways, covered front
TOWN OF CRAWFORD LOG HOME SITUATED ON 25+ ACRES OF SERENE WOODED LAND. This charming 3-bedroom, 2-bathroom log home is situated in the Town of Crawford, within the Pine Bush School District. Conveniently located just 10-15 minutes from local restaurants, shopping centers, and essential services such as banking and postal facilities, this home offers both comfort and accessibility. Surrounded by
NEW CONSTRUCTION!!! Check out this 4 Bedroom, 2.5 Bathroom Colonial nestled in the Town of Montgomery and located in the Valley Central School District. This home is located a short drive to an array of local eateries/restaurants, shopping center, close to several local parks, a quarter mile from the Walden/Wallkill Walking Rail Trail, Wallkill River, and a short drive to most major highways
Nestled within the sought-after Winding Hills Estates, this exceptional home is set on a quiet cul-de-sac and backs directly to the rolling greens of the picturesque Winding Hills Golf Course, an executive 18-hole course surrounded by manicured landscaping. From the moment you arrive, the home impresses with Hardie board siding, a metal roof, blacktopped driveways, paver walkways, covered front
Two adjacent properties offered together as a single opportunity (2056 & 2060 Rt 17K): a preserved 1840 historic farmhouse paired with a separate 2-bedroom residence, with a combined total of approximately 4 acres, 6 bedrooms, 4 baths, and roughly 2,500 square feet of combined living space in Montgomery's Town of Crawford. Built in 1840 and preserved with rare integrity by just two families in
TOWN OF CRAWFORD LOG HOME SITUATED ON 25+ ACRES OF SERENE WOODED LAND. This charming 3-bedroom, 2-bathroom log home is situated in the Town of Crawford, within the Pine Bush School District. Conveniently located just 10-15 minutes from local restaurants, shopping centers, and essential services such as banking and postal facilities, this home offers both comfort and accessibility. Surrounded by
NEW CONSTRUCTION!!! Check out this 4 Bedroom, 2.5 Bathroom Colonial nestled in the Town of Montgomery and located in the Valley Central School District. This home is located a short drive to an array of local eateries/restaurants, shopping center, close to several local parks, a quarter mile from the Walden/Wallkill Walking Rail Trail, Wallkill River, and a short drive to most major highways
NEW CONSTRUCTION!!! Check out this 4 Bedroom, 2.5 Bathroom Colonial nestled in the Town of Montgomery and located in the Valley Central School District. This home is located a short drive to an array of local eateries/restaurants, shopping center, close to several local parks, a quarter mile from the Walden/Wallkill Walking Rail Trail, Wallkill River, and a short drive to most major highways
Welcome to 41 Philip Drive, a beautifully maintained Colonial built by Hillside Homes and set within Montgomery’s desirable Winding Oaks subdivision. Located on a quiet cul-de-sac and positioned on a private, landscaped lot backing to woods, this home offers exceptional curb appeal with a long paved driveway, mature trees, and a peaceful residential setting. Inside, the home features a bright,
Welcome to this beautifully renovated 4-bedroom, 2.5-bath Colonial that perfectly blends timeless charm with modern updates. From top to bottom, this home has been completely renovated and thoughtfully updated, offering truly move-in-ready living. The spacious floor plan features bright, sun-filled rooms, a stunning updated kitchen, beautifully renovated bathrooms, and quality finishes
"We know this property is worth more, but we're letting the market decide! Welcome to 145 Youngblood Road, a rare opportunity where endless possibilities meet peaceful country living. This oversized ranch style home offers exceptional flexibility with a separate apartment above the garage, creating the perfect setup for multigenerational living, owner occupied investment opportunities, guest
A private luxury retreat unlike anything else on the market. Set on 54.10 secluded acres at the end of a long private driveway, 97 Svenski offers an extraordinary combination of privacy, distinctive modern design, smart-home features, and fully renovated, move-in-ready living. This one-of-a-kind residence features 7 bedrooms, 4.5 bathrooms, 1,632+ sq. ft. above grade, plus an additional 1,006 sq.
Nestled at the top of a gentle hill in a quiet cul-de-sac, this 4-bedroom, oversized raised ranch offers a rare opportunity to create something truly special. Set on a one-acre parcel, the property provides both privacy and space—an ideal backdrop for your vision. Owned by the same family for over 50 years, this home is ready for its next chapter. While it requires updating and renovation, the
Enjoy peaceful living in this charming, newly updated private ranch set on over one acre of beautiful property. This inviting home offers the perfect blend of comfort and convenience, featuring a beautifully renovated kitchen and bathroom with modern finishes throughout. A new roof adds additional value and peace of mind.Imagine having a golf course right in your backyard! This property
Discover the potential of 506 Berea Road, a unique real estate opportunity located in the scenic town of Montgomery New York. This property is hitting the market for the first time in over forty years, having been held by the same owner since 1982. For buyers searching for a true Hudson Valley fixer upper or a rewarding investment property in Orange County, this ranch style home offers the
Nestled in the charming village of Montgomery, NY, Hawkins Apartments offers the perfect balance of comfort, convenience, and community.Whether grabbing coffee, dining out, or running errands, everything you need is just minutes from your doorstep. The property is also ideally positioned near major routes such as Route 208, Route 17K, and I-84, making commutes and travel throughout the
Our Montgomery apartments offer a comfortable yet stylish lifestyle right in the heart of the community. With a wide range of amenities and an efficient room plan, each airy one-bedroom apartment provides the perfect solution for comfortable senior living.Close proximity to the charming village of Montgomery makes for a life of convenience and serenity for Montgomery Manor residents,
Loosestrife Fields Apartments is surround by wooded grounds. Enjoy the quiet, nature setting from your patio or balcony in your spacious 1 or 2 bedroom apartment with your own washer and dryer in unit! Easy access to I-84, NYS Thruway, shopping and restaurants.
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