Montgomery Homes for Sale

Welcome to Montgomery, New York – a charming town nestled in the picturesque Orange County. Known for its rich history and vibrant community, Montgomery offers a perfect blend of small-town charm and modern conveniences. With its scenic landscapes, historic landmarks, and a welcoming atmosphere, it’s no wonder that Montgomery is an ideal place to call home.

As you explore this delightful town, you’ll find a variety of recreational opportunities, from hiking in the nearby Hudson Highlands to enjoying a leisurely day at one of the local parks. Montgomery is also home to a thriving arts scene and hosts several community events throughout the year, fostering a strong sense of belonging among residents.

When it comes to finding your dream home, Montgomery has an impressive selection of properties for sale. Whether you’re seeking a cozy single-family home, a spacious townhouse, or a charming historic residence, the real estate market here offers something for everyone. Many homes feature beautiful gardens and outdoor spaces, perfect for enjoying the serene surroundings.

With its excellent schools, family-friendly neighborhoods, and convenient access to major highways and public transportation, Montgomery is an ideal location for commuters and families alike. The local economy is thriving, with quaint shops, restaurants, and essential services just a stone's throw away.

If you’re considering a move to Montgomery, now is the perfect time to explore the homes for sale in this enchanting town. Experience the warmth and charm of Montgomery, and discover why so many are proud to call this beautiful community home!

Newest Montgomery Homes for Sale

$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

$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

$899,900

4 Beds ⋅ 3 Baths ⋅ 1037546 MLS

Turn off the main road and the noise drops away. By the time the fields open up on both sides you have rolled the windows down without deciding to, and the last few minutes of the drive stop counting as a commute. Right now this is 3.35 acres and nothing else, which is the best part of it. Ground has not been broken. Nothing has been framed, poured, painted or decided. The approvals are already in hand, so there is no planning board to sit through and no year of paperwork standing between you and a shovel. Everything still open is the part you actually want to decide. Start with what the land gives you. Room for a fire pit far enough out that the smoke never matters and nobody within earshot minds how late it runs. Room for the garden to get as ambitious as you want. Room for the dog to open up at a full sprint instead of a lap. A tent in July, and a snowfall in January that stays clean all the way to the tree line because nothing is close enough to track it up. Evenings out here run long, and that is the part people underestimate until they have it. The plan runs 2,871 square feet, and the layout is what will get you. A formal dining room for the nights that deserve a real table, and an eat-in kitchen with an island that opens to everything else, because that is where everyone ends up anyway no matter how nicely you set the other room. Ceilings on the first floor run 9 feet so the light carries. Real wood trim around the windows and doors. A fireplace to hold the main living space through those four months when a Hudson Valley evening asks for one. Upstairs, 4 bedrooms, walk-in closets, and a primary suite with a big walk-in shower behind glass doors. Two and a half baths, and a real laundry room instead of a closet with a hookup in it. The cabinets, the counters, the hardware, the paint, the floors in every room are all yours to choose, which means you will never lose a Saturday undoing a decision you had no part in. The basement opens straight out to the yard at ground level, wide glass door and a real window, so it will never read as a basement. A whole extra floor waiting on whatever you decide it should become. A deck off the back steps down into the grass, and the covered front porch will get more use than you are picturing, because sitting outside watching nothing happen turns out to be the entire point of a place like this. The garage takes 2 cars and everything else you keep meaning to sort out. None of the quiet costs you anything either. Dinner at Ward's Bridge Inn when the week has earned one, mornings at Java Blue on Clinton Street, walking loops at Benedict Farm Park, the Walden Wallkill Rail Trail a few minutes up the road. I-84 puts Newburgh and New Paltz within easy reach, the train at Salisbury Mills is about 20 minutes out, and Manhattan sits 70 miles off on the days you need it to. Everything will be new, so nothing needs replacing and nothing sits waiting to surprise you three years in. But that is not what you will remember about this place. You will remember walking this land before a single thing stood on it, and already knowing exactly how the first night on that porch was going to feel.

64 W Corbett 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

$549,900

3 Beds ⋅ 3 Baths ⋅ 1039103 MLS

fast sale needed. Horse property with 7 stall barn and fenced in corrals.. House is fine, but owner removed the flooring down to the floorboards.. also kitchen appliances have been removed.. not a total rehab, but in need of carpet or hardwood, kitchen appliances and some brush hogging.. truly a diamond in the rough .. fantastic views! this place boarded horses only a few years ago.. this is the opportunity you were waiting for..property sold 'as is'

36 W Searsville Road, 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

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.