Montgomery Homes with Valley Central (Montgomery) School district

Welcome to Montgomery, New York—a charming town nestled in the picturesque Hudson Valley in Orange County. Known for its rich history and vibrant community, Montgomery is a delightful blend of small-town charm and modern convenience. With its scenic landscapes, friendly atmosphere, and a strong sense of community, it’s no wonder why so many families are drawn to this captivating area.

Montgomery boasts a variety of homes that cater to diverse lifestyles, from cozy single-family residences to more spacious properties. One of the standout features of this area is its affiliation with the Valley Central School District, renowned for its commitment to academic excellence and holistic student development. Families residing in Montgomery can take pride in the quality education their children receive, with schools that emphasize both academic achievement and extracurricular engagement.

The town is also home to an array of local amenities, including parks, shops, and dining options that reflect the warm community spirit. Outdoor enthusiasts will appreciate the nearby hiking trails and recreational areas, perfect for weekend adventures with family and friends.

In Montgomery, you’ll find not just a house, but a place to call home—where neighbors become friends and every street tells a story. Whether you’re looking to settle down or invest in property, Montgomery offers an inviting environment that perfectly balances tranquility and accessibility. Come explore the charm of Montgomery, where your dream home awaits!

Newest Montgomery Homes with Valley Central (Montgomery) School district

$529,000

3 Beds ⋅ 3 Baths ⋅ 1050379 MLS

A well-maintained raised ranch in the Village of Montgomery, set back from the street on a quiet cul-de-sac in a peaceful, family-friendly area. This 3-bedroom, 3-bath home offers approximately 2,504 square feet of living space, including a spacious finished lower level with versatile rooms and plenty of potential. The home features three full bathrooms, including two with tubs and one with a shower stall. The lower level also includes a separate laundry room with washer and dryer hookups. Step outside to enjoy a private backyard retreat featuring a large heated above-ground pool, expansive deck, covered outdoor seating area, and additional patio space, perfect for entertaining and enjoying the warmer months. A storage shed provides convenient space for outdoor equipment and belongings. Additional highlights include central air conditioning. Located in the Valley Central School District and close to the Village of Montgomery's shops, restaurants, and local amenities. A unique home offering flexible living space, a peaceful setting, and 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

$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

$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

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