Montgomery Homes with Driveway Parking features

Welcome to Montgomery, New York – a charming town nestled in the picturesque Orange County, where history meets modern living. Montgomery is known for its rich heritage, scenic landscapes, and a warm community spirit that makes it a perfect place to call home. With the majestic Shawangunk Mountains to the west and the serene Wallkill River flowing nearby, residents enjoy a blend of natural beauty and small-town charm.

Montgomery boasts a variety of amenities, including quaint shops, delightful eateries, and recreational parks that cater to all ages. The town is also conveniently located near major highways, making commuting to New York City or other parts of the Hudson Valley a breeze. For families, the area is served by excellent schools and community programs, fostering a nurturing environment for children to grow and thrive.

When it comes to housing, Montgomery offers a range of options that cater to diverse lifestyles and budgets. One of the standout features of many homes in this area is driveway parking. Imagine coming home to your own private space, where you can easily park your vehicle without the hassle of street parking. Homes with driveway parking not only provide convenience but also enhance the overall appeal and functionality of the property.

Whether you’re looking for a cozy starter home or a spacious family residence, Montgomery’s real estate market has something for everyone. Embrace the charm of this delightful town, where your dream home awaits!

Newest Montgomery Homes with Driveway Parking features

$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

$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

$519,299

1017454 MLS

Ideal location close to interstate 84 with multiple uses and the property includes a 3-bedroom, 1 bath and a one car attached garage that is nestled.40 acre of fairly level land.

2075 State Route 208 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

$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

$349,999

1 Beds ⋅ 1 Baths ⋅ 1017517 MLS

Welcome to this charming Ranch-style home beautifully nestled on a corner lot in the Village of Montgomery within the Valley Central School District. Showcasing lovely curb appeal with a landscaped front yard, this inviting 1-bedroom, 1-bathroom residence features a versatile office or bonus room to suit your lifestyle. Step inside to discover a bright living room highlighted by gleaming hardwood floors and a cozy corner wood-burning stove resting on a tiled hearth. The spacious, eat-in kitchen boasts rustic wood cabinetry, a decorative backsplash, and ample space for cooking and dining. The well-appointed full bathroom provides a large vanity, tile flooring, and a step-in shower. The living spaces extend into comfortable sleeping and working quarters, including a vibrant bonus room with sliding glass doors leading to the exterior, as well as a spacious primary bedroom featuring large windows and beautiful hardwood floors. Downstairs, a full basement offers excellent storage or expansion potential. Outside, enjoy relaxing or entertaining on the expansive side deck, which overlooks a level, partially fenced yard area. The property also features an attached two-car garage with plenty of interior workspace and an additional detached storage shed for your convenience. Ideally located just two blocks from Veterans Memorial Park and the Village center—which features a variety of eateries, shopping boutiques, local pubs, and the Village hall—this home also provides fantastic commuter convenience, situated close to Route 211, Route 17K, and just a 10-minute drive to Interstate 84.

36 Charles Street, Montgomery

$675,000

3 Beds ⋅ 2 Baths ⋅ 1012189 MLS

Charming, authentic Farmhouse, maintaining plenty of rustic charm with some exposed hand hewn beams, but with every modern update. Private in ground pool, big bonus room over garage, all systems updated or replaced. Central air, new septic tank. Fully furnished for the right buyer. Photos dont do it justice. This home is warm and interesting, you will be refreshed. Just had major price reduction. COME AND SEE!

291 Comfort Trail, Montgomery

$449,900

4 Beds ⋅ 3 Baths ⋅ 1014332 MLS

Welcome home to this spacious 4-bedroom, 3 bath residence with finished lower level on a cul-de-sac including a full acre of land! Solidly maintained with newer roof and updated systems (h/w heater, furnace). Offering space, flexibility, and comfort both inside and out. The home features a top floor open-concept layout filled with natural light and an inviting eat-in kitchen, creating the perfect setting for everyday living and entertaining. The fully finished lower level expands the living space and offers incredible versatility, complete with an over sized family room, an additional bedroom, a kitchenette, a dedicated carpentry/workshop room, and a convenient laundry area. Whether you're looking for extra living quarters, a recreation space, or room for hobbies and projects, this lower level provides endless possibilities. Situated on a full acre of usable property, the outdoor space is ideal for gatherings, gardening, recreation, or simply enjoying the privacy and tranquility of your surroundings. An outdoor shed provides additional storage for tools, equipment, and seasonal items. This property offers the perfect combination of indoor living space and outdoor enjoyment, making it an exceptional place to call home. Schedule your private showing today!

11 Kevin Court, Montgomery

$2,499,900

3 Beds ⋅ 3 Baths ⋅ 1006189 MLS

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 appreciate both refined living and outdoor adventure. Beyond the gated entrance, a winding driveway passes fenced paddocks, open meadows, a pond, farm animal run-in sheds and a row barn, before arriving at the impressive log home, complete with a wraparound covered porch, metal roof, and expansive courtyard driveway with ample space for oversized vehicles and equipment. Inside, the home showcases rich wood craftsmanship, soaring ceilings, and breathtaking views of the surrounding mountains, koi ponds, and manicured gardens. The chef's kitchen features custom wood cabinetry, granite countertops, a center island, and spacious dining area, while a practical mudroom includes a convenient dog washing station. The dramatic great room serves as the heart of the home with floor-to-ceiling windows and a striking stone fireplace. The main level offers a private office, full bathroom, and a luxurious primary suite complete with a walk-in closet and spa-inspired ensuite featuring a floating jetted soaking tub, oversized tiled shower, and double vanity. Nearly every room opens directly to inviting outdoor living spaces that seamlessly connect the home to its natural surroundings. Upstairs, two generously sized bedrooms share a full bath, while a peaceful loft-style sitting area overlooks both the great room below and the picturesque grounds beyond. The partially finished lower level provides endless potential with a full bathroom and bar area already in place, awaiting your personal finishing touches. Step outside and discover a true resort-style oasis. The spectacular multi-level heated pool features a slide, wading area, and extensive lounging spaces. The pool house includes a tiki bar, full bathroom, and outdoor shower, while dual Thor grills, granite serving stations, and a shaded pergola create the ultimate setting for unforgettable gatherings. The estate continues to impress with a heated two-story showroom garage offering over 7,000 square feet of commercial grade space. The upper level includes two guest apartments, each with kitchenettes, bedrooms, and bathrooms, creating exceptional opportunities for extended family, guests, or staff accommodations. Equestrian enthusiasts will appreciate the classic red two-story barn currently configured for five horses with room for expansion, along with a massive hay loft, multiple fenced paddocks, and supporting run-ins. An impressive 6000 sq ft commercial grade mechanic's garage and workshop sits farther down the drive, providing privacy and flexibility for hobbyists, collectors, or business pursuits. Completing this extraordinary offering is a stunning 1+ acre pond featuring docks, a waterfall, and waterside grilling patio—an idyllic backdrop for fishing, entertaining, or simply enjoying the peace and beauty of the Hudson Valley countryside. Rarely does a property offer this level of privacy, recreation, functionality, and luxury. Whether envisioned as a compound, equestrian estate, entertainer's paradise, or Hudson Valley retreat, this iconic property delivers a lifestyle unlike any other.

95 Judson Road, Montgomery

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