Montgomery Real Estate

Welcome to Montgomery, New York – a charming village nestled in the heart of Orange County, where small-town charm meets modern convenience. With its rich history dating back to the 18th century, Montgomery offers a unique blend of historical significance and contemporary living, making it an ideal place to call home.

As you stroll through the picturesque streets, you'll be captivated by the quaint architecture and vibrant community spirit. Montgomery is known for its friendly residents, who take pride in their town and actively participate in local events. The village hosts seasonal festivals, farmer's markets, and community gatherings, fostering a strong sense of belonging and camaraderie.

Nature enthusiasts will find plenty to love about Montgomery, too! The surrounding area boasts stunning landscapes, including hiking trails, parks, and the scenic Wallkill River. Whether you enjoy a peaceful walk in the park or an adventurous day of kayaking, there’s something for everyone to enjoy in this beautiful region.

Education is a cornerstone of Montgomery, with highly-rated schools that prioritize the academic and personal growth of students. Families will appreciate the safe neighborhoods and supportive community, making it a perfect environment for raising children.

Conveniently located just a short drive from the bustling cities of New York and New Jersey, Montgomery offers easy access to urban amenities while maintaining its tranquil, rural charm. With a variety of local shops, restaurants, and recreational activities, residents have everything they need right at their fingertips.

Discover the allure of Montgomery, NY – where history, community, and nature come together to create a truly enchanting place to live. Your dream home awaits in this delightful village!

Newest Listings in Montgomery

$675,000

4 Beds ⋅ 3 Baths ⋅ 1053066 MLS

Welcome Home! Set on approximately 1.9 acres, this spacious bi-level home offers an impressive 3,062 square feet of living space with 4 bedrooms, 3 full bathrooms, two large sheds and an attached 2-car garage. Step inside to a thoughtfully designed layout with generous living spaces and plenty of room to make the home your own. The recently remodeled kitchen brings a fresh, updated feel to the heart of the home and flows naturally into the dining area, while the large living room provides an inviting setting for both everyday living and entertaining. The home offers four generously sized bedrooms, with three featuring walk-in closets, an exceptional amount of storage and a feature not often found throughout multiple bedrooms. Three full bathrooms add convenience across the home's spacious bi-level layout. Just off the rear patio, a bonus sitting room creates another inviting space to relax, entertain, or enjoy the connection between the home's interior and outdoor areas. With multiple living and gathering spaces throughout, the layout offers excellent flexibility to adapt to a variety of needs. Outside, approximately 1.9 acres provide plenty of room to enjoy the property, whether you're spending time on the patio, entertaining outdoors, or simply appreciating the additional space surrounding the home. The attached 2-car garage provides everyday convenience along with additional storage possibilities.

8 Acorn Drive, Montgomery

$449,900

4 Beds ⋅ 3 Baths ⋅ 1052235 MLS

4 Bedroom, 2.5 Bathroom Colonial on 14.40 acres in T/Montgomery! Rocking chair front porch, plenty of room inside and out for entertaining. Close to shopping, schools and amenities. Property is being Sold As-Is, seller will not make repairs. Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. Please see agent remarks for access, showing instructions and offer presentation remarks.

64 Enright Lane, Montgomery

$629,900

4 Beds ⋅ 3 Baths ⋅ 1051813 MLS

NEW CONSTRUCTION IN THE VALLEY CENTRAL SCHOOL DISTRICT—READY TO MOVE IN. This affordable, practical four-bedroom home offers three full bathrooms, more than 2,000' square feet of living space, central air, a propane fireplace, a two-car garage, and a newly graded and seeded yard. Concrete walkways lead to a covered front porch and an inviting main entrance. Inside, the spacious foyer provides direct access to the family room featuring a propane fireplace with ceramic-tiled accents, a wood mantel, recessed lighting, and a sliding door to the backyard. Nearby is the laundry room with window, a full bathroom with ceramic-tile flooring and a tub, plus a private first-floor bedroom. A few steps up to the next level opens to an impressive floor plan with 12-foot ceilings, abundant natural light, and recessed lighting. The kitchen includes an island, pantry, quartz countertops, soft-close drawers and cabinet doors, under-cabinet lighting, all appliances, with propane range. The second floor has full bathroom with tub and ceramic-tile flooring, along with two cozy bedrooms with hardwood floors. The primary bedroom features hardwood flooring, a lighted walk-in closet, and a private bathroom with a ceramic-tile shower and flooring. The home also offers three heating zones—one on each level—central air throughout, and a spacious two-car garage with automatic openers. Short drive to the local golf course make this location special in many ways.

9 Union School Road, Montgomery

$529,000

3 Beds ⋅ 3 Baths ⋅ 1050379 MLS

Offering first-time-on-the-market quality, this well-maintained raised ranch sits on a quiet cul-de-sac in a peaceful Village of Montgomery neighborhood. Cherished and impeccably cared for by its original owners, this 3-bedroom, 3-bath home spans approximately 2,504 square feet of flexible living space, highlighted by soaring cathedral ceilings that create an open, airy atmosphere. The primary main level blends comfort and function, while the fully finished lower level offers versatile bonus rooms tailored for a home office, gym, or recreation space. Three full bathrooms (two with soaking tubs, one with a shower stall) ensure convenience for relatives and guests, alongside a dedicated lower-level laundry room with washer and dryer hookups. Central air conditioning keeps the home comfortable year-round. Step out back to your private outdoor oasis designed for ultimate entertaining. The fully equipped yard features a large, heated above-ground pool, an expansive deck, a cozy covered seating area, and additional patio space. A convenient storage shed keeps lawn care and pool equipment tucked away cleanly. Situated in the desirable Valley Central School District, you are just minutes from the charming shops, local dining, and vibrant community amenities of the Village of Montgomery. A rare opportunity to own a meticulously kept, original-owner home with an exceptional outdoor setup!

104 Ayers Court, Montgomery

$99,900

1047396 MLS

Beautiful Commercial lot in the Town of Montgomery. Offers 30,955 sq ft/ .71 acre. Zoned vacant commercial-330. Has over 150 feet of road frontage. High traffic area and corner lot. Great commuter location- close to 84, 87, 17, and Stewart INTL Airport. Blank canvas and pretty level.

St Rte 208 Ws, Montgomery

$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

$298,500

1043878 MLS

Great land opportunity at the corner of Rt. 17K and Collabar Rd. in the Town of Crawford, raw land of ~3.6 relatively level acres. This land will inspire a new owner to create their successful vision on the important Rte. 17k corridor. 17K is a main thoroughfare from Newburgh to Bloomingburg and up to Rt. 17 (future 86). High visibility corner parcel with Town of Crawford "BP" Business Park zoning overlay (underlying zone may be residential). Approximately 500 feet of frontage on 17K and approximately 380 feet of frontage on County Rte. 43. Currently wooded and undeveloped, with no known engineering or improvements. BP Zoning Town of Crawford shows potential uses of: general retail, personal service, general business office, medical office, banks, restaurant. Further uses in the zone by special permit. Ideally situated just minutes from the thriving Village of Montgomery, NY, the hamlet of Pine Bush, great proximity to Middletown and Newburgh, and convenient to major transportation hubs such as Orange County Airport and Stewart International Airport.

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

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