Montgomery Homes with Heated Garage Parking features

Welcome to Montgomery, New York – a charming village nestled in the heart of Orange County, where historic charm meets modern convenience. Known for its picturesque landscapes and vibrant community, Montgomery offers a delightful blend of small-town warmth and urban accessibility. With its rich history, highlighted by beautifully preserved architecture and a strong sense of community, this area is perfect for families, retirees, and everyone in between.

As you explore Montgomery, you'll be captivated by its scenic parks, local shops, and friendly neighborhoods. The village boasts a variety of recreational activities, from hiking along the scenic trails to enjoying summer festivals that bring residents together. Montgomery’s strategic location provides easy access to major highways, making it a commuter’s dream while still allowing you to enjoy the tranquility of suburban living.

For those seeking homes that offer both comfort and convenience, Montgomery features an impressive selection of properties with heated garage parking. Imagine stepping into your warm, cozy car on a chilly winter morning, ready to tackle the day ahead without the hassle of scraping ice off your windshield. These homes not only enhance your daily routine but also provide added value and protection for your vehicles.

Whether you’re looking for a quaint cottage or a spacious family home, Montgomery has something to suit every lifestyle. Embrace the warmth of this inviting community and discover the perfect home with the features you desire. Montgomery awaits – come and experience the charm for yourself!

Newest Montgomery Homes with Heated Garage Parking features

$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

$2,499,900

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

Start Your Search

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.