Montgomery Homes with Oversized Parking features

Welcome to Montgomery, New York – a charming town nestled in the heart of Orange County, where picturesque landscapes meet a vibrant community spirit. Known for its rich history and welcoming atmosphere, Montgomery offers a perfect blend of small-town charm and modern conveniences. With its lush parks, scenic trails, and a variety of local shops and eateries, residents enjoy a lifestyle that celebrates both relaxation and recreation.

One of the standout features of homes in Montgomery is the availability of properties with oversized parking. For those with multiple vehicles, recreational toys, or simply a love for spacious living, these homes provide the perfect solution. Imagine arriving home to a driveway that can accommodate not just your car but also your RV, boat, or guest vehicles, all while maintaining a neat and organized appearance. Oversized parking is not just a luxury; it’s a practical necessity for families and individuals who value convenience and accessibility.

In addition to the generous parking options, Montgomery boasts a diverse selection of homes, from charming historic houses to modern new builds. The community is known for its friendly neighbors and active lifestyle, with events and activities that cater to all ages. Whether you’re exploring the local farmer's market, enjoying a leisurely walk in one of the scenic parks, or taking part in community events, Montgomery's warm and inviting atmosphere makes it easy to feel right at home.

Discover the allure of Montgomery, where oversized parking meets the charm of small-town living, and find your perfect home today!

Newest Montgomery Homes with Oversized Parking features

$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

$546,900

6 Beds ⋅ 4 Baths ⋅ 1006008 MLS

"We know this property is worth more, but we're letting the market decide! Welcome to 145 Youngblood Road, a rare opportunity where endless possibilities meet peaceful country living. This oversized ranch style home offers exceptional flexibility with a separate apartment above the garage, creating the perfect setup for multigenerational living, owner occupied investment opportunities, guest accommodations, or additional rental income. Nestled in a serene setting, this property is much more than a home. It is a true opportunity property. Previously operating as a highly successful Airbnb with SUPERHOST status, the home enjoyed strong occupancy and consistent demand throughout the year. Today, it remains an attractive option for long term or mid term rentals and has generated interest from companies seeking housing accommodations for employees and contractors. Adding to its appeal, the property is zoned Residential/Mixed Use Commercial, opening the door for a variety of potential uses. Whether you are looking to establish a home based business, create a multigenerational compound, generate rental income, or simply enjoy the abundance of living space, this property offers flexibility that is increasingly difficult to find. Inside, you will discover spacious rooms, multiple bathrooms, and a floor plan designed to accommodate a variety of lifestyles. Outside, enjoy the peace and privacy that make this property such a sought after destination. The sellers are motivated and ready to pass this unique opportunity on to the next owner. Whether you are an investor, entrepreneur, or homeowner seeking space and versatility, 145 Youngblood Road delivers the rare chance to own what feels like two homes in one. Bring your vision, bring your ideas, and unlock the tremendous potential this property has to offer.

145 Youngblood Road, Montgomery

$649,900

6 Beds ⋅ 4 Baths ⋅ 999867 MLS

Two adjacent properties offered together as a single opportunity (2056 & 2060 Rt 17K): a preserved 1840 historic farmhouse paired with a separate 2-bedroom residence, with a combined total of approximately 4 acres, 6 bedrooms, 4 baths, and roughly 2,500 square feet of combined living space in Montgomery's Town of Crawford. Built in 1840 and preserved with rare integrity by just two families in almost 200 years, the 4 bedroom primary farmhouse delivers the kind of atmosphere that new construction cannot replicate. Hand-hewn beams, ultra-wide plank floors, natural woodwork, and four fireplaces anchor the home's historic character throughout the kitchen, living room, primary bedroom, and basement. Thoughtfully maintained rather than modernized into anonymity, the 1,704-square-foot residence blends authentic craftsmanship with practical comfort, including updated windows, modern heating, and a large rear deck that wraps the L-shaped footprint and opens toward the kitchen garden and wooded views across the combined acreage. The second parcel adds a separate 2-bedroom, 1-bath residence with its own entrance, porch, and utilities. Previously rented, it offers flexibility as income-producing space, extended family housing, guest quarters, or private workspace. A 1,200-square-foot pole barn adds additional utility for storage, workshop use, equipment, or creative pursuits. Valley Central School District. No HOA. For the buyer who understands that authenticity cannot be recreated, this is a true Hudson Valley farmhouse property with flexibility, income potential, and preserved historic character. Please note; Taxes, beds, baths and acreage are the combined totals of both properties.

2056 State Route 17K, Montgomery

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