$515,546Average Value$276Average Price per Sq Ft33Homes 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
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GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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On average, homes in Montgomery, NY sell after 66 days on the market compared to the national average of 55 days. The median sale price for homes in Montgomery, NY over the last 12 months is $511,000, up 6% from the median home sale price over the previous 12 months.
Welcome to this charming 3-bedroom, 1-bathroom Cape Cod style home nestled in the picturesque Town of Montgomery, offering the perfect blend of updated living and ultimate commuter convenience. Offering quick access to the Interstate 84 on-ramp from the nearby State Route 17K and Route 208 intersection, and situated just a short drive from local shopping plazas, neighborhood dining, banking,
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.
Full of classic character and versatility, this spacious home at 77 Union Street offers a fantastic opportunity in the Valley Central School District. The property features a spacious 3-bedroom main living area alongside a comfortable 1-bedroom secondary living space, ideal for a home office, guest suite, or additional flexible living arrangements.Classic architectural details include a
VALLEY CENTRAL SCHOOLS! Situated within a 15-minute drive of everyday shopping centers and dining options ranging from casual diners to quick-service eateries. Enjoy outdoor recreation just minutes away at Winding Hills Park, featuring boating, fishing, hiking trails, and playgrounds, or take a quick 10-minute drive into the historic Village of Montgomery to explore boutique shopping, local pubs,
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
Welcome to this charming 3-bedroom, 1-bathroom Cape Cod style home nestled in the picturesque Town of Montgomery, offering the perfect blend of updated living and ultimate commuter convenience. Offering quick access to the Interstate 84 on-ramp from the nearby State Route 17K and Route 208 intersection, and situated just a short drive from local shopping plazas, neighborhood dining, banking,
Turn off the main road and the noise drops away. By the time the fields open up on both sides you have rolled the windows down without deciding to, and the last few minutes of the drive stop counting as a commute.Right now this is 3.35 acres and nothing else, which is the best part of it. Ground has not been broken. Nothing has been framed, poured, painted or decided. The approvals are
A true masterpiece conceptualized by the renowned DeGraw and DeHaan Architects, this luxury 4-bedroom, 2.5-bathroom residence stands as a testament to over 40 years of elite design expertise. The home boasts a brilliant open floor plan, sophisticated finishes, and masterful architectural flourishes that create an inviting yet grand atmosphere. Offering over 2,600 square feet of impeccably
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 555 State Route 416 in the heart of Montgomery, NY—Enjoy Village Charm and country life!!! This spacious 4-bedroom, 2-bath home offers comfortable living with plenty of room to grow. Enjoy an inviting eat-in kitchen featuring new stainless steel appliances, a dedicated dining area, and a large living room perfect for family gatherings and entertaining. An unfinished, easily accessible
Do you know what you can do with over 27 acres? Create the homestead you’ve always dreamed about! Spend weekends riding ATVs through your own private trail system. Grow your own food in the established 40’ x 40’ garden. Raise chickens in the 12’ x 12’ chicken coop with an expansive 12’ x 40’ run. Follow the trails approximately 10 acres into the property and disappear into the woods at your own
Introducing a prime commercial investment opportunity on State Rt 17K, Montgomery, NY, 12549. Comprised of two lots togther - Apn #334289-027-000-0005-003.000-0000 9 (6.6 acres) and Apn#334289-027-000-0005-002.000-0000 (one acre) this 7.6-total acre property, zoned B4 Highway Commercial, offers exceptional potential for a multitude of uses. With 600 Ft of highway frontage and a signalized
Welcome to one of the Hudson Valley's most iconic private estates; an extraordinary 38+ acre retreat offering luxury, recreation, equestrian amenities, abundant space for custom vehicle enthusiasts and unmatched entertaining spaces. Known locally as the famed "Orange County Choppers House," this remarkable property blends rustic elegance with modern comfort in a setting designed for those who
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.
Valley Central School District! Nestled on the outskirts of the charming village of Montgomery, this exquisite apartment offers a rare blend of convenience and serenity. Situated on a sprawling four-acre lot, the property boasts a picturesque setting with a private pond, creating an idyllic haven for those seeking a peaceful retreat.
This fully renovated 3/4 bedroom contemporary situated on nearly 2 acres in Montgomery features fully renovated kitchen with guartzite counters, new custom cabinets, Stainless appliances, huge primary bedroom with abundant closets, and imported tile bath, spacious secondary bedrooms, new central ac, freshly painted, new windows, 2 car garages. Privacy with easy proximity to nearby shopping,
Beautiful Village Colonial for Rent in the Heart of Montgomery – Utilities Included!Experience the charm of village living in this beautifully maintained 4-bedroom, 2-bath Colonial, ideally located in the quaint Village of Montgomery. Blending timeless character with modern updates, this spacious home features a grand foyer, wide plank pine floors, a formal living room and dining room, and an
Looking for a comfortable rental in Montgomery with plenty of space to relax and enjoy? This spacious 3-bedroom, 3-bath home at 68 Weaver Street offers a peaceful neighborhood setting within the Valley Central School District. The home features a renovated kitchen, updated roof, and a whole-house standby generator for added convenience and peace of mind. The kitchen provides a welcoming space for
Large one bedroom apartment on the second floor. Spacious open livingroom/dining room with exposed beams offering charm from the barn. Small eat in kitchen Off strrt parking Located in the village of Montgomery
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