Montgomery Homes for Sale

Welcome to Montgomery, New York – a charming town nestled in the picturesque Orange County. Known for its rich history and vibrant community, Montgomery offers a perfect blend of small-town charm and modern conveniences. With its scenic landscapes, historic landmarks, and a welcoming atmosphere, it’s no wonder that Montgomery is an ideal place to call home.

As you explore this delightful town, you’ll find a variety of recreational opportunities, from hiking in the nearby Hudson Highlands to enjoying a leisurely day at one of the local parks. Montgomery is also home to a thriving arts scene and hosts several community events throughout the year, fostering a strong sense of belonging among residents.

When it comes to finding your dream home, Montgomery has an impressive selection of properties for sale. Whether you’re seeking a cozy single-family home, a spacious townhouse, or a charming historic residence, the real estate market here offers something for everyone. Many homes feature beautiful gardens and outdoor spaces, perfect for enjoying the serene surroundings.

With its excellent schools, family-friendly neighborhoods, and convenient access to major highways and public transportation, Montgomery is an ideal location for commuters and families alike. The local economy is thriving, with quaint shops, restaurants, and essential services just a stone's throw away.

If you’re considering a move to Montgomery, now is the perfect time to explore the homes for sale in this enchanting town. Experience the warmth and charm of Montgomery, and discover why so many are proud to call this beautiful community home!

Newest Montgomery Homes for Sale

$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

$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

$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

$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

$749,999

3 Beds ⋅ 3 Baths ⋅ 1015155 MLS

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, eateries, and wineries. The location is just the start - this 3-bedroom, 2.5-bathroom Colonial/Farmhouse-style home is situated on 3 acres boasting the upmost privacy. Inside, you are welcomed by an inviting foyer featuring wide-plank wood floors, classic white wainscoting, and a traditional staircase that sets a warm, rustic tone throughout the residence. The spacious living room is anchored by a traditional brick fireplace, oversized windows allow natural light to pour in while framing peaceful woodland views. Seamless archways and wide openings lead into the formal dining room. At the heart of the home is a stunning country kitchen defined by character and craftsmanship, boasting exposed wooden ceiling beams, custom knotty pine cabinetry with glass-front display accents, and durable tile flooring. The kitchen is fully equipped for the culinary enthusiast with premium stainless steel appliances—including a gas range and built-in microwave, a custom tile backsplash, an integrated wine and beverage cooler, and a versatile breakfast bar peninsula offering stool seating. Adjacent to the kitchen, a sun-drenched breakfast nook and casual dining area with large sliding glass doors that open directly onto the outdoor living space. The main level also thoughtfully features a dedicated office or study with rich wood flooring and crown molding, alongside a convenient first-floor full laundry room. On the upper level, the residence continues to impress with its signature wide-plank wood flooring and solid knotty pine doors. The second floor hosts three spacious bedrooms, including a primary suite featuring a bright natural lighting, elegant crown molding, and a private en-suite bathroom equipped with durable tile flooring, a separate glass-enclosed walk-in shower, and a deep soaking whirlpool tub set beneath a bright window looking out to the trees. Two additional generously sized bedrooms offer comfortable layouts, ample closet storage and picturesque views of the surrounding foliage. Located off the hallway is a full bathroom featuring an expansive vanity with a sleek granite countertop, generous cabinetry storage, and modern fixtures. Down below, the home features a full basement that expands your utility/storage options, complete with a private infrared sauna. Outside, the home is surrounded by a mature canopy of trees that ensures total seclusion, featuring classic neutral grey siding, a traditional brick chimney, a two-car attached garage with ample storage, and a paved driveway providing generous driveway parking. The backyard serves as a private resort-style oasis. An expansive multi-level wooden deck spans the rear of the residence, providing generous space for open-air dining, lounging, and soaking in the relaxing hot tub. Step down to discover a custom in-ground swimming pool surrounded by a stamped concrete patio. Combining timeless architectural charm, exceptional interior craftsmanship, and a backyard paradise—all just minutes from local parks, shops, and dining—this Montgomery property is an extraordinary country retreat.

165 Benedict Road, Montgomery

$724,000

4 Beds ⋅ 3 Baths ⋅ 1018110 MLS

Private 6.5-acre Victorian retreat with heated salt water pool! Tucked away on a quiet cul-de-sac, this impressive home features a dramatic two-story foyer, soaring ceilings, creates a grand first impression and leads to spacious living areas throughout the home and a flexible floor plan with exceptional potential on each floor including the walk out basement. Enjoy scenic views, generous indoor and outdoor living, and a prime location just minutes from shopping, dining, and Woodbury Common Premium Outlets. The main level features a generously sized formal dining room, ideal for entertaining, holiday gatherings, and everyday living. A private den or home office provides the perfect space for remote work, studying, or a quiet retreat. One of the home’s standout features is the expansive bonus room, larger than the primary suite and complete with its own private entrance. This versatile space offers endless possibilities, whether used for multigenerational living, guest accommodations, a second home office, a media or game room, fitness studio, or creative workspace. The spacious eat-in kitchen provides ample room for casual dining and opens directly to a deck overlooking the above ground pool and the breathtaking natural surroundings. Enjoy peaceful mornings, outdoor dining, and unforgettable sunsets while taking in the beauty and privacy of approximately 6.5 acres. The expansive property also offers room for future enhancements or expansion. A conveniently located first-floor laundry room with a utility sink adds everyday practicality and convenience. The spacious primary suite serves as a private retreat, showcasing a distinctive octagonal tray ceiling, an en-suite bathroom, and an oversized walk-in closet with abundant storage. The walk-out basement expands the home’s possibilities by providing direct access to the outdoor patio, creating a seamless connection between indoor and outdoor living while offering additional space for recreation, entertaining, or future finishing. The shed presents an exciting opportunity to create a charming pool cabana, hobby space or workshop. Additional highlights include above-ground oil heating and an attached two-car garage. Whether you’re searching for privacy, versatility, scenic surroundings, or room to grow, this exceptional Victorian estate offers a rare opportunity to create the lifestyle you’ve been dreaming of. Make an appointment for a private tour and experience this beauty for yourself!

27 Grosso Court, Montgomery

$449,000

3 Beds ⋅ 1 Baths ⋅ 1018676 MLS

AVAILABLE! Welcome to this beautifully renovated 3-bedroom ranch set on a private 1-acre lot in Hamptonburgh, directly across from Thomas Bull Memorial Park. recently renovated and move-in ready, this home features refinished hardwood flooring, a bright updated kitchen with casual dining area, 1 full bath, new roof, new siding, and a charming new front porch. new driveway, new ductless air conditioning and heating units, freshly painted. The covered rear deck is perfect for relaxing, entertaining, or simply enjoying the peaceful surroundings. A large detached 2-car garage with water and electric provides excellent space for parking, storage, hobbies, or a workshop. With its fresh updates, inviting layout, and scenic location near parks, recreation, and commuter conveniences, this home is a wonderful Hudson Valley find.

230 Route 416, Montgomery

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