Montgomery Homes under $500,000

Welcome to Montgomery, New York – a charming town nestled in the heart of Orange County, where picturesque landscapes meet a rich tapestry of history and community spirit. With its convenient location just a short drive from both New York City and the scenic beauty of the Hudson Valley, Montgomery offers the perfect blend of suburban tranquility and urban accessibility.

As you explore this vibrant town, you’ll discover a variety of delightful amenities, including quaint shops, local eateries, and beautiful parks, making it an ideal place for families, young professionals, and retirees alike. Montgomery is also known for its excellent school district and a strong sense of community, hosting events throughout the year that bring residents together and celebrate local culture.

For those seeking to make Montgomery their home, there’s an exciting opportunity to find beautiful properties under $500,000. The housing market here features a diverse selection of charming single-family homes, townhouses, and even some cozy condos, all offering great value for your investment. Whether you’re looking for a starter home, a place to raise a family, or a serene retreat, Montgomery has something to suit every taste and budget.

Imagine waking up to scenic views of the surrounding mountains and enjoying a leisurely stroll through the town's welcoming streets. With its affordable housing options, rich community life, and proximity to both nature and urban conveniences, Montgomery, NY is not just a place to live; it’s a place to thrive. Come and discover your dream home in this enchanting town today!

Newest Montgomery Homes under $500,000

$324,000

3 Beds ⋅ 1 Baths ⋅ 1057815 MLS

Get ready to enjoy your new home in a choice location situated on nearly 6 acres of property. The features abound including level yard space, low taxes, a multi-story accessory building and plenty of room for future expansion. The list of perks continue as you open the door to your updated home. You will notice the wide open floor plan that flows from the dining area towards the kitchen and the charming living room. Your kitchen is complete with a breakfast bar, stainless steel appliances, ample storage and counter space as well as a side door that could lead way for a future patio. Just down the hall you will find three bedrooms and a well appointed bathroom featuring a stall shower and the convenience of a stackable washer/dryer. The property itself provides a multitude of options for hobby farming, recreational activities, gardening and entertainment space. The multi-level accessory building is excellent for additional storage, workshop, a dedicated workspace/office, home gym and more. The convenient location along with amenities such as central AC, on demand water heater, double pane windows and ample parking just add to the value of this property. Enjoy the proximity to Winding Hills county park, golfing, shops, hiking, restaurants and so much more.

2031 State Route 17K, Montgomery

$349,750

3 Beds ⋅ 3 Baths ⋅ 1057617 MLS

Rare opportunity in Spring Meadow! 18 Autumn Leaf Court offers three bedrooms, two and a half baths, and approximately 1,437 sq. ft. Three bedroom units in this sought after community rarely become available, making this an opportunity buyers have been waiting for. Spring Meadow offers the ease of condominium living in an established, well-maintained community just moments from everything the Village of Montgomery has to offer. Valley Central Schools. Enjoy convenient access to local restaurants, shops, parks and village events, with I-84 and other major commuter routes nearby. Opportunities like this within the community, let alone Montgomery, do not come around often. Don't miss it.

18 Autumn Leaf Court, Montgomery

$399,900

4 Beds ⋅ 3 Baths ⋅ 1043339 MLS

Lovely level lot offers charming setting for this Large Colonial home. Featuring 4 bedrooms, 3 full baths and large unfinished basement. This diamond in the rough has generous sized living/dining room and very spacious kitchen. Some work is need but well worth the effort!! Great value in lovely village location offers easy access to major highways and commuting.

24 Fairview Avenue, 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

$449,999

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

$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

$415,000

4 Beds ⋅ 3 Baths ⋅ 1014332 MLS

Welcome home to this spacious 4-bedroom, 3 bath residence with finished lower level on a cul-de-sac including a full acre of land! Solidly maintained with newer roof and updated systems (h/w heater, furnace). Offering space, flexibility, and comfort both inside and out. The home features a top floor open-concept layout filled with natural light and an inviting eat-in kitchen, creating the perfect setting for everyday living and entertaining. The fully finished lower level expands the living space and offers incredible versatility, complete with an over sized family room, an additional bedroom, a kitchenette, a dedicated carpentry/workshop room, and a convenient laundry area. Whether you're looking for extra living quarters, a recreation space, or room for hobbies and projects, this lower level provides endless possibilities. Situated on a full acre of usable property, the outdoor space is ideal for gatherings, gardening, recreation, or simply enjoying the privacy and tranquility of your surroundings. An outdoor shed provides additional storage for tools, equipment, and seasonal items. This property offers the perfect combination of indoor living space and outdoor enjoyment, making it an exceptional place to call home. Schedule your private showing today!

11 Kevin Court, Montgomery

$429,900

3 Beds ⋅ 3 Baths ⋅ 994511 MLS

Looking for a quiet home in Montgomery with space to relax and grow? This 3-bedroom, 3-bath home at 68 Weaver Street offers a comfortable layout, thoughtful updates throughout, and a peaceful neighborhood feel—all within the Valley Central School District. This home comes with valuable upgrades including a renovated kitchen, updated roof, and finished basement, giving you peace of mind and move-in-ready convenience. The kitchen is designed for everyday cooking and gathering, while the upgraded roof and basement add long-term durability and flexible living space. Built for everyday living, this 3068 sq ft home sits on a oversized village lot, offering plenty of room for outdoor entertaining, gardening, or simply enjoying fresh air. Natural light fills the home during the day, and the layout creates a calm, comfortable flow for daily life. A whole house standby generator upgrade adds an extra layer of reliability, keeping essential systems powered during unexpected outages. Located in Orange County, you’ll enjoy easy access to local shops, dining, and commuter routes while still embracing a small-town lifestyle. Whether you're starting out or looking to settle down, this home blends comfort, updates, and convenience in one inviting package.

68 Weaver Street, Montgomery

$429,900

4 Beds ⋅ 2 Baths ⋅ 984326 MLS

Welcome to 555 State Route 416 in the heart of Montgomery, NY—Enjoy Village Charm and country life!!! This spacious 4-bedroom, 2-bath home offers comfortable living with plenty of room to grow. Enjoy an inviting eat-in kitchen featuring new stainless steel appliances, a dedicated dining area, and a large living room perfect for family gatherings and entertaining. An unfinished, easily accessible basement provides ample storage space and potential for future use. Additional highlights include central air conditioning, a generator hookup, a breezeway connecting to the garage, and a shed for extra storage. The property also boasts a large, flat backyard—ideal for outdoor entertaining, gardening, or relaxing. Conveniently located near shops, restaurants, schools, and parks, this home offers the perfect balance of convenience and tranquility. Ice Shield wiring installed to protect Roof.

555 State Route 416, Montgomery

$409,000

2 Beds ⋅ 1 Baths ⋅ 948942 MLS

Welcome to Holbrow House at 46 Union Street, a lovingly maintained and updated 1818 home in the quaint Village of Montgomery. As soon as you enter, you're greeted by the warmth of the historic wide plank wood floors and rooms filled with natural light. The main living area offers great flexibility with an additional room that can be used as an office, den or guest space. Charming details throughout the home include French doors, solid bluestone windowsills, and a restored working gas fireplace. The kitchen blends old and new, with newer stainless steel appliances, while highlighting the original stone foundation and historic doors. An attached utility room has a dedicated space for your washer and dryer. Upstairs, the primary bedroom features vaulted ceilings, along with a second bedroom and another bonus space that can adapt to your needs. Outside, the fenced-in yard feels private and inviting, with mature trees, established plantings and seasonal flowers. A shed provides convenient storage for gardening tools and outdoor equipment. Located just moments from Montgomery's shops, coffee houses, restaurants, pickleball, tennis and basketball courts, baseball fields, hiking trails and access to the Wallkill River. This home offers the best of village living in a truly special setting. 11 minute drive to Campbell Hall Train Station; 22 minute drive to Beacon Train Station; 90 minute train ride to NYC. You will not want to miss this special home.

46 Union Street, Montgomery

$330,000

6 Beds ⋅ 2 Baths ⋅ 875699 MLS

This spacious 6-bedroom home is full of potential and ready for your vision. Set in a highly desirable area, it offers a rare opportunity to create your dream home in a prime location. With five bedrooms upstairs and a large main-level bedroom, this layout is ideal for multi-generational living or flexible space needs. The home features an oversized living room, two full bathrooms, a dedicated office, and classic old-style charm throughout. A generous driveway provides ample parking for family and guests. Whether you're an investor or a homeowner looking to renovate and build equity, this property offers the perfect canvas. Bring your ideas and unlock the full potential of this well-located gem! New furnace (2023), newer water heater. Valley Central School District, Close to Wineries, Breweries, Restaurants, Hiking, Legoland etc.

265 Goodwill Road, Montgomery

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