Montgomery Real Estate

Welcome to Montgomery, New York – a charming village nestled in the heart of Orange County, where small-town charm meets modern convenience. With its rich history dating back to the 18th century, Montgomery offers a unique blend of historical significance and contemporary living, making it an ideal place to call home.

As you stroll through the picturesque streets, you'll be captivated by the quaint architecture and vibrant community spirit. Montgomery is known for its friendly residents, who take pride in their town and actively participate in local events. The village hosts seasonal festivals, farmer's markets, and community gatherings, fostering a strong sense of belonging and camaraderie.

Nature enthusiasts will find plenty to love about Montgomery, too! The surrounding area boasts stunning landscapes, including hiking trails, parks, and the scenic Wallkill River. Whether you enjoy a peaceful walk in the park or an adventurous day of kayaking, there’s something for everyone to enjoy in this beautiful region.

Education is a cornerstone of Montgomery, with highly-rated schools that prioritize the academic and personal growth of students. Families will appreciate the safe neighborhoods and supportive community, making it a perfect environment for raising children.

Conveniently located just a short drive from the bustling cities of New York and New Jersey, Montgomery offers easy access to urban amenities while maintaining its tranquil, rural charm. With a variety of local shops, restaurants, and recreational activities, residents have everything they need right at their fingertips.

Discover the allure of Montgomery, NY – where history, community, and nature come together to create a truly enchanting place to live. Your dream home awaits in this delightful village!

Newest Listings in Montgomery

$479,900

3 Beds ⋅ 2 Baths ⋅ 1026792 MLS

LOVELY HOME IN THE VILLAGE OF MONTGOMERY WITH RIVER VIEWS! This well maintained 1770 sq.ft. , 3 bedroom, 2 bathroom home has a lot to offer; an open floor plan with a spacious deck, with an awning, for entertaining or just relaxing and enjoying the river view. Stepping downstairs you will find a finished family room plus the 12x20 finished bonus room, Ideal for an office, game room, play room, fitness room or whatever fits your individual needs. Let's not stop there, there is a large unfinished area-great for storage. All this and it includes a cedar closet, a shed, and a freezer. Close to schools, parks, shopping, major highways, restaurants and all the charm the Village has to offer. COME TAKE A LOOK -YOU WON"T BE DISAPPOINTED!

168 Pleasant Avenue, Montgomery

$499,999

4 Beds ⋅ 3 Baths ⋅ 1032648 MLS

Full of classic character and versatility, this mother-daughter home at 77 Union Street offers a fantastic opportunity for investors or owner-occupants alike, located in the Valley Central School District. The property features a spacious 3-bedroom unit alongside a comfortable 1-bedroom efficiency, ideal for generating rental income or providing space for extended living arrangements. Classic architectural details include a charming gabled roofline, original wood siding, Victorian-style finishes, and a welcoming screened front porch, perfect for relaxing or entertaining. Inside, the home is filled with natural light and features built-in shelving throughout for added charm and storage. The 3-bedroom unit offers spacious rooms, plenty of cabinetry, a washer/dryer hookup in the kitchen, and a classic claw-foot tub. Additional features include a cozy fireplace, in-ground pool, and a private patio area for outdoor enjoyment. Driveway parking provides added convenience, and the mature landscaping with established trees and shrubs adds to the home's inviting curb appeal. Situated on a quiet street within walking distance to local shops, dining, and everyday conveniences, 77 Union Street combines timeless charm with practical multi-unit flexibility.

77 Union Street, Montgomery

$235,000

3 Beds ⋅ 1 Baths ⋅ PALY2002494 MLS

Welcome to 130 W Houston Avenue, where small-town charm meets everyday convenience in the heart of Montgomery. This inviting home offers a wonderful opportunity to enjoy an updated home with the convenient location. Easy access to everything the Susquehanna Valley has to offer. Ideally situated just minutes from local parks, schools, restaurants, and shopping, this property also provides quick access to Route 15 and Interstate 180, making commuting to Williamsport, Lewisburg, and surrounding communities simple. This home features all of the big ticket items updated in recent years, as well as the space to enjoy it.

130 Houston Ave, Montgomery

$510,000

4 Beds ⋅ 3 Baths ⋅ 1032471 MLS

Welcome to this beautiful, meticulously maintained, thoughtfully upgraded, 4 bedroom, 3 full bath, built just three years ago! From your first step inside, you'll notice how gorgeous this home is as the amenities shine through. Open floor plan shows off the large living room, formal dining room, eat-in kitchen with center island, stainless steel appliances, granite countertops, custom tile backsplash, and an abundance of cabinets. 13ft vaulted ceilings highlight how the home fills with natural light. Step out onto the upper deck for great views and bbq. Spacious master bedroom with en suite, double vanity, and walk-in closet. Laundry room on the main floor. Additionally, we have the fourth bedroom, additional full bathroom, and family room on the lower level - great for a separate suite, guests, extended family, or just bonus recreation room. Check out to the private lower level deck. Town water & sewer, natural gas connected, great location, and amazing neighborhood. Valley Central Schools. Ready to move right in!

9 Overlook Terrace, Montgomery

$565,000

1026946 MLS

Looking for a high visibility location? This 23.01 acre vacant land is steps away from a 4 corner intersection of route 17K and route 208 with a high traffic count that leads to interstates, shopping plazas, communities , subdivision, village vibes nearby and also, the neighboring commercial properties consist of Walden Savings Bank, Law Offices, Girl Scotts of America Headquarters and Chamber of Commerce. Shopping Plazas and Amazon Fulfillment Warehouse Headquarters is only a couple of miles away. Road frontage is 17K. Conceptual plans from 2005 consist of multiple parking areas with a one level 24,000 sq. ft office building.

#17K NS Rt-17K Route, Montgomery

$499,000

3 Beds ⋅ 2 Baths ⋅ 1028032 MLS

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, roadways and schools.

219 Benedict Road, Montgomery

$565,000

1026975 MLS

#17K NS Rt-17K Route, Montgomery

$669,000

4 Beds ⋅ 3 Baths ⋅ 1026839 MLS

One incredibly upgraded home with two driveways and two garages! This fully renovated 4-bedroom, 2.5-bath, 2,646-square-foot Colonial checks boxes you didn't even know you had. A second driveway leads to a heated 24x30 workshop with a car lift, ideal for hobbyists or anyone needing serious workspace, plus a portable garage for extra storage. Inside, hardwood floors run throughout the freshly painted main level, complemented by crown molding, solid wood doors, custom built-ins, and two fireplaces. The updated kitchen features quartz counters, a marble island, and stainless steel appliances. New Andersen sliders open to a covered Trex deck with overhead fans and lighting — a true all-weather entertaining space. The finished basement (not included in square footage) adds bonus living space perfect for a game room, media room, or home gym. Upstairs, the primary suite offers an updated ensuite bath and a custom California closet with pocket door. Major systems have been thoughtfully updated: new roof (2024), high-efficiency Ascent furnace (2024), Roth oil tank (2025), expansion tank (2026), car lift (2025), Andersen sliders (2023), and carpet (2024). Kitchen, bathrooms, and lighting have all been refreshed within the last two years. Set on 1.7 private acres with fruit trees — and the pool table and hot tub are included. Move-in ready with nothing left to do but enjoy it.

83 Little Collabar Road, Montgomery

$1,250,000

4 Beds ⋅ 5 Baths ⋅ 1025121 MLS

Set on 11.9 private, wooded acres with sweeping easterly views toward the Hudson River ridgeline, this French Country-inspired estate blends old-world architecture with modern comfort. A dramatic turret, multiple gables, and an arched stone entry portico set the tone before you even step inside. A soaring two-story foyer welcomes you home, with a custom wrought-iron and oak staircase leading to an open catwalk overlooking the great room below. The great room itself impresses with a vaulted, beamed ceiling, a stone-mantled gas fireplace, and a wall of French doors framing long-range views. A formal dining room with designer Venetian plaster-style walls and an arched picture window offers an elegant space for entertaining, flowing easily into the gourmet kitchen, where a professional 6-burner gas range, oversized granite island, custom oak cabinetry, and a sun-filled eat-in dining area create a true chef's kitchen. The first-floor primary suite is a private retreat, with French doors opening to the wraparound deck, a spa-style bathroom featuring a corner jacuzzi tub, dual-sink vanity, glass walk-in shower, and radiant heated floors for year-round comfort. The finished lower level extends the home's entertaining possibilities with a full wet bar, a double-sided wood-burning fireplace shared with the family room, a dedicated home theater, a cedar-lined sauna, an exercise room, a full bathroom, and a versatile bonus room ideal as a den, guest space, or office. Outside, enjoy a wraparound deck connecting to the primary suite, a screened-in sitting area, and a hot tub included in the sale, all overlooking a private, tree-lined setting. A whole-house backup generator, Buderus high-efficiency heating system, radon mitigation system, and Andersen windows and doors round out this thoughtfully maintained home. Additional highlights include a second-floor ensuite, a home office, and a spacious bonus room over the garage. This is a rare opportunity to own a private, amenity-rich retreat just minutes from the Village of Montgomery's shops, restaurants, and parks, with easy access to commuting routes throughout the Hudson Valley.

250 Corbett Road, Montgomery

$2,700,000

3 Beds ⋅ 3 Baths ⋅ 1026440 MLS

Labors of love are the best kind. They’re ones that carry projects further than any fuel can. At just 60 miles northwest of NYC, this bucolic equine estate served as a private polo field, equestrian center and most importantly a place to live within a landscape that could just as easily be the fields of France or Orange County. When purchased in 2011 the current owners enlisted a renowned architect to complete an extensive historic renovation and restoration project that both reimagined and preserved the architectural integrity of this 1910 farmhouse. Most notably, hand-hewn beams were uncovered and the living room ceiling opened up to create a dramatic space that spans from front to back of the house and flows seamlessly to the outdoors through the French doors that lead to the bluestone patio, pool and rolling fields. The kitchen was also updated complete with a La Cornue stove that now takes center stage. Designed as the hub of the house for preparing meals and entertaining, the kitchen flows to the dining room and leads to the screened in sunroom for panoramic meals made for lingering amongst the landscape. The stone basement was also finished as part of the renovation and serves as a family room with both an office nook and extra space for guests. On the 2nd floor, dormers were added to bring more natural light into the upstairs bedrooms. The owners also purchased surrounding parcels to add to the existing acreage. The total is now 80.4 acres which provides an array of opportunities for further development. Outbuildings include a 10-stall barn with tack room, work room, bathroom, washer and dryer and apartment for staff or a clubhouse, as well as a large garage/barn for parking or equipment storage. The property also features a 550-ft by 220-ft crusher dust arena and track, a 300-yard by 130-yard polo field, a 6-horse walker with roof and variable speed and 2 run-in sheds. Wooded and open trails meander throughout the property offering the space to slow the pace, recalibrate, and connect with the landscape for a return to a natural circadian rhythm. Revel in the raw textures of the trees and fields as far as the eye can see and soak in the sun as it lights up the land and shimmers on the pool. 11 minutes to Middletown grocery stores like Adams Fairacre Farms, restaurants and shopping. 15 minutes to City Winery and it’s new affiliated hospitality project Milk Factory. For the car enthusiast Monticello Motor Club, is just 32 minutes away.

123 Collabar Road, Montgomery

$674,999

4 Beds ⋅ 4 Baths ⋅ 1025068 MLS

The original owners say it's time to move and pass this home to new owners. This property sits on 1.36 acres and offers over 2500 sq feet of living space. It has 2 primary bedrooms one on the first floor which has a its own bathroom and laundry. Upstairs is another primary bedroom 2 additional bedrooms, laundry, a bathroom and bonus space. Use your imagination and use it how you want to. There is a full front porch you can sit and drink your morning coffee. If you don't want to sit there sit out on the back deck that is located off the dining room. The Kitchen is open up to the living room. This home offers a lot of natural light. it is close to i84 for commuters, local shops and 208,17k. This home is energy effect with geothermal heating and cooling. Also, feeds the hot water. Windows have a transferable lifetime warranty. High ceiling throughout and a full unfinished basement with bilco doors. Plenty of room for storage.

272 Beaver Dam Road, Montgomery

$499,000

3 Beds ⋅ 3 Baths ⋅ 1023226 MLS

Come see all the great features this home has to offer. The main living area offers three bedrooms, two full baths, a spacious living room, and a large eat in kitchen which connects to a large deck. The lower level has multiple finished rooms that offer endless possibilities. There is storage space, a full bathroom, washer/dryer, and a connected garage all on the lower level. The lower level has a walk out onto a concrete patio that is covered by the large second store deck. These two outdoor spaces make this home feel even larger than it is and offer a great space for entertaining and outside leisure activities. A long garage with room for multiple vehicles, tankless water heater, water treatment system, pull down stairs to the attic, extensive cabinets, freshly painted deck, invisible dog fence, and wood burning stove are some of the many amazing features this home has to offer. Come book your showing today!

326 Bullville Road, Montgomery

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