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

$769,000

4 Beds ⋅ 3 Baths ⋅ 1036991 MLS

Picture-perfect country living starts right here. From the wraparound porch out front to the almost 6 acres surrounding it, 28 Enright Lane sets the tone for a slower, more spacious way of living the moment you arrive. This beautifully maintained 4-bedroom, 2.1-bathroom Colonial offers almost 3,100 square feet of thoughtfully designed living space. Inside, a foyer flows into a cozy TV room, a bright living room with soaring ceilings, an eat-in kitchen, and a formal dining room. Also on the main level is a dedicated laundry room with a sink, situated next to the attached 2-car garage. Upstairs, you'll find 4 sizable bedrooms, including a large primary suite with a private full bathroom. Down below, a full-sized unfinished basement adds even more potential, ready to be transformed into a home gym, media room, or additional living space to suit your needs. The grounds themselves are the real showstopper. Acres of the perfect combination of open lawn and mature trees, ideal for recreation, hobbies, or simply breathing room. From the paved driveway, a gravel trail leads to a large 2-story barn offering exceptional flexibility, perfect for extra parking, storage, or the workshop you've always wanted. And the location doesn't disappoint. Just under 2 hours from NYC, you're a short drive from local shops and restaurants, including the celebrated City Winery Hudson Valley and Angry Orchard Brewery, making weekend outings as easy as staying home. In a world that never slows down, 28 Enright Lane is a continuous breath of fresh air. Space to think, room to create, and a setting that gives your mind the true freedom.

28 Enright Lane, Montgomery

$729,999

4 Beds ⋅ 3 Baths ⋅ 1046076 MLS

Welcome to a home designed for comfortable everyday living, memorable celebrations and making the most of every season. Built in 2017, this spacious four-bedroom residence offers room to gather, relax, work and entertain. The main level features warm hardwood floors, inviting formal living and dining rooms, and a beautifully appointed kitchen where everyone can come together. Granite countertops, a large center island, stainless-steel appliances, abundant cabinetry, a butler’s pantry and an additional pantry closet make meals and entertaining effortless. Upstairs, four generously sized bedrooms with impressive walk-in closets provide comfortable private retreats. The spacious primary suite includes a spa-inspired bath with a double vanity, bidet and oversized dual-head shower. The basement offers extra storage space. Step outside and enjoy your own backyard getaway, complete with a heated saltwater pool, composite decking, an expansive stone patio, firepit and hot tub beneath a gazebo. The vinyl-fenced yard provides plenty of space for outdoor fun, gardening and summer gatherings, while a large shed keeps everything organized. Owned solar panels, central air and a two-car garage with 220-volt service add everyday convenience. Located in the Town of Montgomery within the Valley Central School District, this welcoming home is close to shopping, local amenities and major highways—offering the space and lifestyle you have been waiting for.

392 Bailey Road, Montgomery

$7,499,999

1040970 MLS

*Brand New Industrial Property for Sale* This state-of-the-art industrial building boasts brand new construction, featuring a stunning 32-foot ceiling height, beautifully appointed offices, modern kitchens, and a spacious conference room. With 6 loading docks, this property is perfect for businesses seeking a premier industrial location with exceptional amenities, high visibility, and easy accessibility along Route 17B. Additionally, this unique offering includes a separate residential property, providing a potential source of monthly income $3400. Selling together for $7,999,000.

2265 State Route 17k, Montgomery

$850,000

4 Beds ⋅ 3 Baths ⋅ 1044645 MLS

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 developed campsite. Swim all summer in the 33-foot above-ground pool, sit beside a crackling fire all winter, and enjoy the kind of privacy that’s becoming harder and harder to find in Orange County. At 960 County Route 17, you don’t have to choose-you can have the house, the land AND the lifestyle. Spanning over 27 acres across three parcels, this extraordinary property offers a rare combination of usable acreage, recreation and extreme privacy-with so much of the work already done for you. And then there’s the house. This beautiful Bi-lonial was built just four years ago with exceptional attention to detail. With 4 bedrooms and 3 full baths, this home offers approximately 2,592 finished square feet of beautifully maintained living space with all the modern amenities you would want without sacrificing the country setting you’ve been searching for. Upgraded spray foam insulation, central air, a whole-house generator, water softener system and wood-burning fireplace provide comfort, efficiency and peace of mind in every season. The primary suite is a true retreat with its own en-suite bath, jetted tub and two walk-in closets; while a dedicated laundry room, generous storage and thoughtfully designed living spaces make the home as functional as it is inviting. A 12’ x 18’ shed provides additional storage for all the equipment, tools and toys that come with enjoying a property like this. But perhaps the greatest luxury here is something you simply can’t manufacture: space, privacy and freedom. This isn’t simply a house with acreage-it’s the opportunity to come home, shut out the rest of the world and enjoy a lifestyle that has already been created for you!

960 County Route 17, Montgomery

$419,900

3 Beds ⋅ 2 Baths ⋅ 1041824 MLS

This beautifully renovated ranch-style home offers 3 bedrooms, 2 full baths, and 1,104 sq ft of modern, move-in-ready living in the Town of Montgomery. Set right on Route 17K, this property combines the comfort of a fully updated home with the convenience of being close to everything—major highways, shopping, schools, parks, and everyday amenities. Every major upgrade has already been completed, giving buyers true peace of mind. The home features a new roof and gutters, new blacktop driveway, new boiler, new electric panel, new AC system, and new windows. Inside, the renovations continue with refinished hardwood floors, a brand-new kitchen showcasing granite countertops, new appliances, tile flooring, and a stylish backsplash. Both full bathrooms have been completely remodeled with fresh, contemporary finishes, and recessed lighting adds a bright, modern touch throughout. With its thoughtful updates, single-level layout, and unbeatable location, this turnkey ranch offers the perfect blend of comfort, convenience, and quality—an ideal choice for buyers seeking a beautifully finished home in the heart of the Hudson Valley.

995 State Route 17K, Montgomery

$484,999

4 Beds ⋅ 3 Baths ⋅ 1042236 MLS

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 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 main living area 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, versatile living space.

77 Union Street, Montgomery

$759,000

4 Beds ⋅ 3 Baths ⋅ 1042126 MLS

Welcome home! This 4 bed, 3 bath Colonial situated on just over 18 acres. FIRST FLOOR PRIMARY ENSUITE! Step inside to the spacious foyer, each room offers dedicated living spaces and hardwood flooring throughout. Formal dining, eat in kitchen with granite & SS appliances, conveniently located laundry/mudroom off garage. Spacious living room featuring a gas fireplace and large windows with abundant light. Extra room for office space on second and first floor. Offering plenty of privacy, room to roam, and endless possibilities. Set well off the road in a peaceful country setting, this home provides the perfect combination of space and convenience.

39 Jacob Rumph Court, Montgomery

$454,900

3 Beds ⋅ 1 Baths ⋅ 1040825 MLS

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, postal services, area schools, and parks, this location is hard to beat. Inside, the home has been meticulously updated to feature a stunning modern open-concept main floor. The kitchen is a true centerpiece, boasting sleek white shaker-style cabinets with modern silver hardware, elegant butcher block countertops throughout, a matching central island, a charming window over the sink with a view, and a full suite of stainless steel appliances including an electric range and over-the-range microwave. This space flows seamlessly under a rustic wood-wrapped beam into a sun-drenched, expansive living and dining area featuring dark plank flooring, highlighted by a cozy painted grey brick fireplace, a distinct caged industrial-style chandelier over the dining area, large windows, and inviting French doors that open to the outside. Stepping through these French doors, you are welcomed into an expansive enclosed rear porch that offers an ideal space for entertaining or relaxing while enjoying the outdoor scenery. This rustic retreat boasts rich wood flooring and a striking exposed wood-beam ceiling. The room is framed by warm wood-paneled lower walls and a continuous band of sliding windows that flood the space with natural light and provide panoramic views of the backyard. A smooth grey-painted interior wall seamlessly ties the space back to the main home's modern aesthetic, while a white exterior door offers direct, convenient access to the yard. The tranquil bedrooms provide a peaceful retreat, showcasing warm, glowing hardwood floors, crisp white trim, fresh light grey walls, and bright multi-pane windows. Serving the home is a beautifully updated full bathroom that pairs classic elements, like a crisp white pedestal sink, with striking modern matte black fixtures and dark tile flooring. Heading upstairs, you will discover a sprawling, versatile upper level characteristic of classic Cape Cod architecture, accessed by a central staircase with white posts. This expansive open room boasts stunning wide-plank wood flooring and charming sloped ceilings painted crisp white against light grey knee walls. Bathed in natural light from multiple multi-pane dormer windows, the space includes classic flush-mount dome lighting and multiple convenient access doors for eaves storage. Downstairs, this property also features a full unfinished basement equipped with convenient laundry hookups, providing abundant storage space. The exterior of the property is just as inviting, presenting classic brown siding, dual dormers, and a charming covered front porch accented by black railings and a decorative glass front door. A paved driveway leads to an attached lower-level garage, flanked by attractive stone retaining walls and hardscaped steps. In the rear, you will find an expansive, lush green lawn bordered partially by a white privacy fence and mature shade trees. Outdoor entertaining is a breeze on the lovely flagstone patio situated just off the back entrance and screened porch. Adding incredible versatility to the sprawling yard are two unique outbuildings set against a tranquil wooded backdrop: a single-story storage shed with a metal roof and double doors, and a distinct two-story playhouse featuring an adjacent paved parking pad and external wooden stairs leading to an upper-level entrance. With modern fixtures and thoughtful updates inside and out, this meticulous, move-in-ready home perfectly positions you to enjoy the best of Montgomery living from your very first day.

49 Bailey Road, Montgomery

$325,000

3 Beds ⋅ 1 Baths ⋅ 1039803 MLS

WELL MAINTAINED RANCH!!! This 3 bedroom ranch in the Town of Montgomery offers a beautiful eat-in-kitchen and a sunroom perfect for relaxing or entertaining. It ideally located close to Schools, Restaurants, Parks, Shops, the train, bus and major highways. Make an Appointment Today!

973 State Route 17K, Montgomery

$1,100,000

4 Beds ⋅ 3 Baths ⋅ 1033185 MLS

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 designed living space, this gorgeous farmhouse colonial makes a stunning first impression with charcoal-grey siding and an expansive wrap-around front porch, a 2-car attached garage and plenty of driveway parking, all beautifully nestled within the exciting new subdivision, The Ponds at Montgomery and located in the Valley Central School District. The property is perfectly positioned just off Route 17K for easy access to major shopping and restaurants, sitting just a five-minute drive from the Historic Village of Montgomery's fine dining, boutiques, and Veterans Memorial Park, and Wallkill River while also being a mere 10 minutes from Winding Hills Park, Thomas Bull Park and 20 minutes from Stewart International Airport via the nearby Interstate 84 on-ramp. Inside, expansive light wide-plank wood flooring flows throughout the main level, which includes a custom mudroom with a built-in bench, a sleek powder room, and a great room defined by soaring vaulted ceilings, exposed white beams, and an impressive floor-to-ceiling white shiplap fireplace with a rustic wood mantel. The heart of the home is a state-of-the-art chef’s kitchen featuring crisp white Shaker cabinetry, a custom wood-toned range hood, marble-patterned quartz countertops, and a generous contrasting wood-grain island illuminated by striking globe pendant lights. A grand staircase with oak treads and modern black balusters leads upstairs to the opulent primary suite, a serene retreat featuring a massive, organized walk-in closet with custom shelving and a spa-like ensuite bathroom boasting a warm wood-toned double vanity, a deep freestanding soaking tub beneath a large picture window, and an enormous architectural shower with a dark charcoal textured accent wall. Completing this exceptional second floor are three additional sun-drenched bedrooms with spacious double-door closets, a beautifully appointed full hallway bathroom with a massive white double vanity and grey stone-look floor tiles, and a highly functional dedicated laundry room outfitted with white Shaker upper cabinetry, a utility sink, and a long dark charcoal folding counter designed to conveniently house rolling laundry hampers underneath.

29 Peale Place, 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

$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

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