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$449,900
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

$535,000
4 Beds 3 Baths 992729 MLS
Set on 3.4 acres in Montgomery within a highly sought after neighborhood! This spacious rambler offers comfort, versatility, and room to grow. A welcoming covered front porch and expansive rear porch create ideal spaces for relaxing or entertaining. Inside, the generously sized kitchen features abundant cabinetry and a central island, perfect for gathering and everyday living. All bedrooms are conveniently located on the main level, providing easy and accessible living. Two basement spaces offer exceptional flexibility for storage, recreation, or perhaps future finished space. Please note that the laundry area is located downstairs in the basement. The property extends beyond the backyard treeline, forming a large rectangular lot with plenty of open space to enjoy. Solar panels are not yet owned and monthly payment is $215.73 monthly, the contract is eligible to be transferred to the next owners. Don’t miss the opportunity to experience this unique property—schedule your private tour today.

65 Judson Road, Montgomery

$7,100,000
985929 MLS
This full service equestrian facility, in the Montogmery area of Orange County, NY is less than 2 hours from NYC and sited on 129 acres. It has been currently improved as a horse traning and boarding facility. The property includes a 1/2 mile standardbred training track and equestrian related structures totaling 87,167 square feet. The on-site improvements include 9 stables that contain a total of 255 stalls, an exercise pavillion, swimming pond, viewing office and several multi-family dwellings for staff and/or on-site owners. There is both a veterinary building and a blacksmith facility. There are multiple residenes for staff, management and owners. Cash flow is there with a courrent occupancy of 150 stalls. This highly desirable area of the Hudson Valley offers surrounding features such as inns, restaurants and attractions such as City Winery. A horse therapy program for victims of PTSD, trauma, or those with developmental disabilites could easily be a thriving enterprize, when combined with the income of the current number horses boarded here. Build on this already thriving facility, with your own business acumen and enjoy life in the beautiful Hudson Valley. Other animal therapies and programs such as goat yoga, rescue operations etc may also be combined to add appeal and variety to this large property with so many possibilities!

261 Bullville Road, Montgomery

$449,900
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

$874,999
3 Beds 2 Baths 982897 MLS
TOWN OF CRAWFORD LOG HOME SITUATED ON 25+ ACRES OF SERENE WOODED LAND. This charming 3-bedroom, 2-bathroom log home is situated in the Town of Crawford, within the Pine Bush School District. Conveniently located just 10-15 minutes from local restaurants, shopping centers, and essential services such as banking and postal facilities, this home offers both comfort and accessibility. Surrounded by nature, it is near several parks, including the Crawford Walking Trail and Winding Hills County Park. Major highways, including Route 17K, Route 302, and Interstate 84, provide easy access to Orange County Airport and Stewart International Airport, making travel and commuting effortless. The location is just the start check out the amenities this home has to offer starting with the kitchen combining classic craftsmanship with contemporary convenience. Deep green cabinetry with black iron hardware is complemented by butcher block style countertops, offering both style and function. A farmhouse sink sits beneath a row of large windows, allowing natural light to fill the space while providing a view of the surrounding trees. Exposed log beams and wood-paneled ceilings add to the warm, rustic aesthetic, while stainless steel appliances integrate modern practicality. The open-concept living and dining areas highlight the home’s impressive architecture. Vaulted ceilings with exposed log rafters create an airy, spacious feel, while large windows frame the natural scenery. The dining space sits beneath a classic chandelier, while the adjacent living area is anchored by a floor-to-ceiling stone fireplace, complete with a wood-burning stove. The natural wood flooring enhances the seamless flow between spaces, emphasizing the home’s log cabin character. The main level bathroom features a modern-rustic blend of design elements, including a sleek vanity with matte black fixtures, a bold patterned tile floor, and a tiled shower with classic subway tile detailing. Upstairs, the lofted ceilings continue into the bedrooms, where exposed log beams create a distinctive, cozy atmosphere. Large windows allow for ample natural light, while the combination of wood and neutral-toned walls maintains a balanced aesthetic. Plush carpeting provides warmth underfoot, and built-in storage adds functionality to the space. The second bathroom reflects a refined yet rustic style, featuring a modern black vanity, a crisp white sink, and a walk-in shower with elegant marble-patterned tile. The contrast between the wood ceiling and the contemporary finishes gives the space a refined yet cohesive look. The property extends to an expansive backyard, bordered by mature trees for privacy and natural beauty. A secondary outbuilding offers additional storage, workspace options or an additional two car garage. The peaceful setting, combined with the home’s well-crafted details and thoughtful updates, makes this property a timeless retreat. This will not last long on the market, don't delay, call now for your showing!!!

294 Comfort Trail, Montgomery

$547,000
976242 MLS
Position your business for success with this outstanding commercially zoned (B-1) property ideally located seconds from Exit 5 on Interstate 84 visible to over 14000 vehicles per day in the heart of Montgomery. Offering excellent visibility and strong sightlines, this exceptionally well-maintained building benefits from steady traffic flow and easy accessibility. Currently operating as a successful salon, the property provides exceptional versatility for a wide range of permitted uses under B-1 zoning, including retail, office and service-oriented businesses. Previously home to a deli, the building retains an existing exhaust system and even a drive-up window - making it attractive for food service or grab-and-go concepts. The site includes 19 dedicated parking spaces and is surrounded by national retailers, popular fast-food establishments and other established businesses, enhancing both exposure and customer draw. Whether you're an owner-user looking to establish or expand your business, or an investor seeking a flexible, income-producing asset, this property offers a strategic location, strong visibility and endless potential.

2039 State Route 208, Montgomery

$1,145,000
4 Beds 3 Baths 975612 MLS
Your private retreat in the Hudson Valley, 80 minutes from the city. Ten estate-like acres, a heated pool, and total seclusion. With Stewart Airport just 30 minutes out and the best of the region within easy reach: golf, fishing, boating, lakes and rivers, miles of hiking, skiing, and the charming hamlets of the Valley, with the Shawangunk Ridge and the Catskills close by. The home lives up to the land. Renovated and move-in ready, it's an easy place to land — a bright, open layout, hardwood floors throughout, a chef's kitchen designed for gatherings and entertainment with a built-in wine fridge, and a primary suite that's its own escape, with a spa bath and soaking tub. Generous rooms flex to whatever you need — guests, media room, home gym, office. The massive basement is a blank canvas for any passion: wine cellar, fitness room, home theater, or all three. Major systems are done — bathrooms, floors, kitchen, pool, and deck renovated, plus new HVAC, water heater, and a meticulously maintained water-treatment system. Nothing to do but settle in. Outside, the grounds are made for it — a massive deck with built-in Sonos sound, a freshly redone 20x40 heated pool for long summer days, a fire pit for starry evenings, an enclosed garden with grapevines, a private orchard, a playground, and a pad with water and shore power for a camper, boat, or trailer. Woods and open space, entirely your own. Space, privacy, and the city never far. Come see it for yourself.

170 Dickerson Avenue, Montgomery

$2,895,000
6 Beds 9 Baths 970238 MLS
A Private Hudson Valley Estate 48.5 Acres of Luxury and Recreation Set across 48.5 breathtaking acres in Montgomery, New York, this extraordinary 6,415-square-foot estate offers a rare opportunity to own a private retreat where luxury, nature, and recreation exist in perfect harmony. Thoughtfully designed for both grand entertaining and comfortable living, the residence features six spacious bedrooms, each with its own private en-suite bath, along with three additional half baths for guests. Elegant living spaces are anchored by two fireplaces, creating warm and inviting settings throughout the home. Resort-style amenities elevate the lifestyle experience. Enjoy a private indoor swimming pool, a dedicated cinema room with nine plush theater seats, and an expansive game and recreation room featuring a pool table, foosball, and air hockey-perfect for gatherings and entertainment year-round. Outdoor living is equally impressive. Three expansive decks overlook the property's peaceful natural surroundings, while the grounds themselves present a remarkable blend of open fields and wooded privacy. Two scenic private ponds invite fishing, kayaking, paddleboarding, and quiet moments by the water, and a tennis court area provides additional recreational possibilities. Whether envisioned as a luxurious full-time residence, an exclusive weekend escape, or a high-end retreat destination, this remarkable estate offers exceptional versatility and investment potential. A property of this scale, privacy, and amenity is truly rare-offering a lifestyle defined by space, serenity, and elevated living in the heart of the Hudson Valley.

198 Corbett Road, Montgomery

$999,999
968171 MLS
PRIME INVESTMENT OPPORTUNITY IN THE HEART OF MONTGOMERY!!! Seize this incredible chance to start or bring your business to the Historic District of the Village of Montgomery! This unique property features two separate buildings just half a mile from the village center, offering excellent visibility and accessibility. Surrounded by a vibrant mix of established local eateries like Wards Bridge Inn, Wildfire Grill and the City Winery, charming Village boutiques and shops, banking and postal services, and community hubs such as the Montgomery Senior Center and Veterans Memorial Park, Paul Jr. Designs Dog-Park and near the scenic Wallkill River and all within the highly regarded Valley Central School District, this location ensures high foot traffic and community engagement. This property consists of TWO separate buildings - #135 currently utilized as a deli/pizzeria storefront, approximately 2,104 sqft and features a kitchen, office, half bathroom and ample parking space for 20+ vehicles. 2nd floor features a separate apartment with 3 Bedrooms, 1 Bathroom, approximately 1,124sqft. #139 Union St is the neighboring single family home with 2 Bedrooms, 1 bathroom, measuring approx 782 sqft. This unique offering presents both residential and commercial opportunities in a a prime location. Inquire today for more details.

135 - 139 Union Street, Montgomery

$409,000
2 Beds 1 Baths 948942 MLS
(***Previous deal fell through due to buyer financing***) 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

$449,999
945428 MLS
Opportunities Are Endless! An incredible expansion opportunity awaits with this commercial property, now available on the market! Strategically located in a prime area of the Town of Montgomery, this property offers versatile potential for various business ventures just perfect for investors, entrepreneurs, or those looking to expand their portfolio. This building offers exceptional accessibility as it is located near most major highways, including Interstate 84, Route 17K, Route 208 and this building is a short 20-minute drive to Stewart International Airport, making it ideal for businesses requiring regional or international connectivity. This property is located in the Industrial 1 zoning district which accommodates a wide range of both permitted & special permitted uses included (but not limited to) business, office, professional, utility, personal service shops, retail stores, food services, animal hospital/boarding facilities, and even non-intensive warehouse operations. Inquire about the proposed 6,700+ sqft expansion! Don’t miss this opportunity to establish or expand your business in a prime, rapidly developing area!

120 Bracken Road, Montgomery

$499,000
932689 MLS
Discover your own slice of the Hudson Valley at 109 White Birch Lane — a beautiful raw acreage parcel located on a private, dead-end road in the Town of Montgomery. This property offers a peaceful and secluded setting while still being just minutes from everything. Enjoy close proximity to the Villages of Montgomery and Walden, as well as easy access to I-84 and Stewart International Airport, making it both convenient and private. Whether you’re looking to build your dream home, create a private outdoor retreat, or establish a recreational getaway, this property offers endless potential. The natural surroundings provide a perfect backdrop for hiking, ATV riding, or simply enjoying the quiet and beauty of the countryside. If you’ve been searching for the ideal balance of privacy, location, and opportunity, 109 White Birch Lane delivers — a true Hudson Valley oasis ready for your vision. Fully surveyed lot with engineering plans and passed perc test!

109 White Birch Lane, Montgomery

$499,000
930755 MLS
Introducing a prime commercial investment opportunity on State Rt 17K, Montgomery, NY, 12549. Comprised of two lots togther - Apn #334289-027-000-0005-003.000-0000 9 (6.6 acres) and Apn#334289-027-000-0005-002.000-0000 (one acre) this 7.6-total acre property, zoned B4 Highway Commercial, offers exceptional potential for a multitude of uses. With 600 Ft of highway frontage and a signalized intersection situated at mid-frontage, this parcel ensures unparalleled visibility and accessibility. Its strategic location, less than one mile from the new Amazon Fullfillment Warehouse in Orange County, NY, further enhances its appeal for savvy investors. Don't miss out on the chance to capitalize on this versatile and high-traffic location in the heart of the thriving Montgomery area. Discover the potential of Rt 17K Coldenham, a vibrant hub for commercial investment in Montgomery, NY. This sought-after location offers landlords and retailers an exciting opportunity to tap into a high-traffic market. The dynamic market of Rt 17K Coldenham presents a wealth of potential for those seeking to establish a presence in a rapidly developing and prosperous commercial district.

State Route 17k Ss, Montgomery

$1,750,000
833668 MLS
LOCATION LOCATION LOCATION!!! $108k in annual rental income!!! 9 TOTAL BAYS OF SHOP SPACE! HIGH VISIBILITY LOCATION! Exceptional commercial opportunity in absolutely incredible location! This super visible commercial property is situated at the entrance to the Village of Montgomery on Route 17K, right next to Wards Bridge ensuring incredible visibility, traffic, and accessibility. Set on just under three quarters of an acre of land, the site is adaptable for multiple commercial uses, with I2 zoning the list is long! Over 6,500 total square feet between the two buildings/three spaces. Main shop is 3,000 sq. ft. with three 14' doors, a 16'x16' office space, bathroom and second level storage, second shop area is 2,160 sq. ft. with two 14' doors and two 12' doors. Upper street level shop is 1,350 sq. ft. with two 12' foot doors and an office. This is an absolutely amazing chance to own a riverfront industrial property in one of the most versatile locations to hit the market this year! Featuring 9 total bays of shop space, this property offers unmatched flexibility for a variety of businesses. Extensive recent upgrades, a well-maintained and renovated property with a long list of recent upgrades. Large rear parking area perfect for staff, equipment, or any additional business needs. This is an extraordinary opportunity if you’re looking for prime industrial space in an unbeatable location. Call today for a private viewing.

66-68 Ward Street, Montgomery

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