Refine Search
Map
Sort by
$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
$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
$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
$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
$669,000
4 Beds ⋅ 3 Baths ⋅ 1026839 MLS
One incredibly upgraded home with two driveways and two garages! This fully renovated 4-bedroom, 2.5-bath, 2,646-square-foot Colonial checks boxes you didn't even know you had. A second driveway leads to a heated 24x30 workshop with a car lift, ideal for hobbyists or anyone needing serious workspace, plus a portable garage for extra storage. Inside, hardwood floors run throughout the freshly painted main level, complemented by crown molding, solid wood doors, custom built-ins, and two fireplaces. The updated kitchen features quartz counters, a marble island, and stainless steel appliances. New Andersen sliders open to a covered Trex deck with overhead fans and lighting — a true all-weather entertaining space. The finished basement (not included in square footage) adds bonus living space perfect for a game room, media room, or home gym. Upstairs, the primary suite offers an updated ensuite bath and a custom California closet with pocket door. Major systems have been thoughtfully updated: new roof (2024), high-efficiency Ascent furnace (2024), Roth oil tank (2025), expansion tank (2026), car lift (2025), Andersen sliders (2023), and carpet (2024). Kitchen, bathrooms, and lighting have all been refreshed within the last two years. Set on 1.7 private acres with fruit trees — and the pool table and hot tub are included. Move-in ready with nothing left to do but enjoy it.

83 Little Collabar Road, Montgomery
$1,099,000
4 Beds ⋅ 5 Baths ⋅ 1025121 MLS
Set on 11.9 private, wooded acres with sweeping easterly views toward the Hudson River ridgeline, this French Country-inspired estate blends old-world architecture with modern comfort. A dramatic turret, multiple gables, and an arched stone entry portico set the tone before you even step inside. A soaring two-story foyer welcomes you home, with a custom wrought-iron and oak staircase leading to an open catwalk overlooking the great room below. The great room itself impresses with a vaulted, beamed ceiling, a stone-mantled gas fireplace, and a wall of French doors framing long-range views. A formal dining room with designer Venetian plaster-style walls and an arched picture window offers an elegant space for entertaining, flowing easily into the gourmet kitchen, where a professional 6-burner gas range, oversized granite island, custom oak cabinetry, and a sun-filled eat-in dining area create a true chef's kitchen. The first-floor primary suite is a private retreat, with French doors opening to the wraparound deck, a spa-style bathroom featuring a corner jacuzzi tub, dual-sink vanity, glass walk-in shower, and radiant heated floors for year-round comfort. The finished lower level extends the home's entertaining possibilities with a full wet bar, a double-sided wood-burning fireplace shared with the family room, a dedicated home theater, a cedar-lined sauna, an exercise room, a full bathroom, and a versatile bonus room ideal as a den, guest space, or office. Outside, enjoy a wraparound deck connecting to the primary suite, a screened-in sitting area, and a hot tub included in the sale, all overlooking a private, tree-lined setting. A whole-house backup generator, Buderus high-efficiency heating system, radon mitigation system, and Andersen windows and doors round out this thoughtfully maintained home. Additional highlights include a second-floor ensuite, a home office, and a spacious bonus room over the garage. This is a rare opportunity to own a private, amenity-rich retreat just minutes from the Village of Montgomery's shops, restaurants, and parks, with easy access to commuting routes throughout the Hudson Valley.

250 Corbett Road, Montgomery
$2,700,000
3 Beds ⋅ 3 Baths ⋅ 1026440 MLS
Labors of love are the best kind. They’re ones that carry projects further than any fuel can. At just 60 miles northwest of NYC, this bucolic equine estate served as a private polo field, equestrian center and most importantly a place to live within a landscape that could just as easily be the fields of France or Orange County. When purchased in 2011 the current owners enlisted a renowned architect to complete an extensive historic renovation and restoration project that both reimagined and preserved the architectural integrity of this 1910 farmhouse. Most notably, hand-hewn beams were uncovered and the living room ceiling opened up to create a dramatic space that spans from front to back of the house and flows seamlessly to the outdoors through the French doors that lead to the bluestone patio, pool and rolling fields. The kitchen was also updated complete with a La Cornue stove that now takes center stage. Designed as the hub of the house for preparing meals and entertaining, the kitchen flows to the dining room and leads to the screened in sunroom for panoramic meals made for lingering amongst the landscape. The stone basement was also finished as part of the renovation and serves as a family room with both an office nook and extra space for guests. On the 2nd floor, dormers were added to bring more natural light into the upstairs bedrooms. The owners also purchased surrounding parcels to add to the existing acreage. The total is now 80.4 acres which provides an array of opportunities for further development. Outbuildings include a 10-stall barn with tack room, work room, bathroom, washer and dryer and apartment for staff or a clubhouse, as well as a large garage/barn for parking or equipment storage. The property also features a 550-ft by 220-ft crusher dust arena and track, a 300-yard by 130-yard polo field, a 6-horse walker with roof and variable speed and 2 run-in sheds. Wooded and open trails meander throughout the property offering the space to slow the pace, recalibrate, and connect with the landscape for a return to a natural circadian rhythm. Revel in the raw textures of the trees and fields as far as the eye can see and soak in the sun as it lights up the land and shimmers on the pool. 11 minutes to Middletown grocery stores like Adams Fairacre Farms, restaurants and shopping. 15 minutes to City Winery and it’s new affiliated hospitality project Milk Factory. For the car enthusiast Monticello Motor Club, is just 32 minutes away.

123 Collabar Road, Montgomery
$519,299
1017454 MLS
Ideal location close to interstate 84 with multiple uses and the property includes a 3-bedroom, 1 bath and a one car attached garage that is nestled.40 acre of fairly level land.

2075 State Route 208 Road, Montgomery
$749,999
3 Beds ⋅ 3 Baths ⋅ 1015155 MLS
VALLEY CENTRAL SCHOOLS! Situated within a 15-minute drive of everyday shopping centers and dining options ranging from casual diners to quick-service eateries. Enjoy outdoor recreation just minutes away at Winding Hills Park, featuring boating, fishing, hiking trails, and playgrounds, or take a quick 10-minute drive into the historic Village of Montgomery to explore boutique shopping, local pubs, eateries, and wineries. The location is just the start - this 3-bedroom, 2.5-bathroom Colonial/Farmhouse-style home is situated on 3 acres boasting the upmost privacy. Inside, you are welcomed by an inviting foyer featuring wide-plank wood floors, classic white wainscoting, and a traditional staircase that sets a warm, rustic tone throughout the residence. The spacious living room is anchored by a traditional brick fireplace, oversized windows allow natural light to pour in while framing peaceful woodland views. Seamless archways and wide openings lead into the formal dining room. At the heart of the home is a stunning country kitchen defined by character and craftsmanship, boasting exposed wooden ceiling beams, custom knotty pine cabinetry with glass-front display accents, and durable tile flooring. The kitchen is fully equipped for the culinary enthusiast with premium stainless steel appliances—including a gas range and built-in microwave, a custom tile backsplash, an integrated wine and beverage cooler, and a versatile breakfast bar peninsula offering stool seating. Adjacent to the kitchen, a sun-drenched breakfast nook and casual dining area with large sliding glass doors that open directly onto the outdoor living space. The main level also thoughtfully features a dedicated office or study with rich wood flooring and crown molding, alongside a convenient first-floor full laundry room. On the upper level, the residence continues to impress with its signature wide-plank wood flooring and solid knotty pine doors. The second floor hosts three spacious bedrooms, including a primary suite featuring a bright natural lighting, elegant crown molding, and a private en-suite bathroom equipped with durable tile flooring, a separate glass-enclosed walk-in shower, and a deep soaking whirlpool tub set beneath a bright window looking out to the trees. Two additional generously sized bedrooms offer comfortable layouts, ample closet storage and picturesque views of the surrounding foliage. Located off the hallway is a full bathroom featuring an expansive vanity with a sleek granite countertop, generous cabinetry storage, and modern fixtures. Down below, the home features a full basement that expands your utility/storage options, complete with a private infrared sauna. Outside, the home is surrounded by a mature canopy of trees that ensures total seclusion, featuring classic neutral grey siding, a traditional brick chimney, a two-car attached garage with ample storage, and a paved driveway providing generous driveway parking. The backyard serves as a private resort-style oasis. An expansive multi-level wooden deck spans the rear of the residence, providing generous space for open-air dining, lounging, and soaking in the relaxing hot tub. Step down to discover a custom in-ground swimming pool surrounded by a stamped concrete patio. Combining timeless architectural charm, exceptional interior craftsmanship, and a backyard paradise—all just minutes from local parks, shops, and dining—this Montgomery property is an extraordinary country retreat.

165 Benedict 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
$2,499,900
3 Beds ⋅ 3 Baths ⋅ 1006189 MLS
Welcome to one of the Hudson Valley's most iconic private estates; an extraordinary 38+ acre retreat offering luxury, recreation, equestrian amenities, abundant space for custom vehicle enthusiasts and unmatched entertaining spaces. Known locally as the famed "Orange County Choppers House," this remarkable property blends rustic elegance with modern comfort in a setting designed for those who appreciate both refined living and outdoor adventure. Beyond the gated entrance, a winding driveway passes fenced paddocks, open meadows, a pond, farm animal run-in sheds and a row barn, before arriving at the impressive log home, complete with a wraparound covered porch, metal roof, and expansive courtyard driveway with ample space for oversized vehicles and equipment. Inside, the home showcases rich wood craftsmanship, soaring ceilings, and breathtaking views of the surrounding mountains, koi ponds, and manicured gardens. The chef's kitchen features custom wood cabinetry, granite countertops, a center island, and spacious dining area, while a practical mudroom includes a convenient dog washing station. The dramatic great room serves as the heart of the home with floor-to-ceiling windows and a striking stone fireplace. The main level offers a private office, full bathroom, and a luxurious primary suite complete with a walk-in closet and spa-inspired ensuite featuring a floating jetted soaking tub, oversized tiled shower, and double vanity. Nearly every room opens directly to inviting outdoor living spaces that seamlessly connect the home to its natural surroundings. Upstairs, two generously sized bedrooms share a full bath, while a peaceful loft-style sitting area overlooks both the great room below and the picturesque grounds beyond. The partially finished lower level provides endless potential with a full bathroom and bar area already in place, awaiting your personal finishing touches. A full house generator offers peace of mind all year long. Step outside and discover a true resort-style oasis. The spectacular multi-level heated pool features a slide, wading area, and extensive lounging spaces. The pool house includes a tiki bar, full bathroom, and outdoor shower, while dual Thor grills, granite serving stations, and a shaded pergola create the ultimate setting for unforgettable gatherings. The estate continues to impress with a heated two-story showroom garage offering over 7,000 square feet of commercial grade space. The upper level includes two guest apartments, each with kitchenettes, bedrooms, and bathrooms, creating exceptional opportunities for extended family, guests, or staff accommodations. Equestrian enthusiasts will appreciate the classic red two-story barn currently configured for five horses with room for expansion, along with a massive hay loft, multiple fenced paddocks, and supporting run-ins. An impressive 6000 sq ft commercial grade mechanic's garage and workshop sits farther down the drive, providing privacy and flexibility for hobbyists, collectors, or business pursuits. Completing this extraordinary offering is a stunning 1+ acre pond featuring docks, a waterfall, and waterside grilling patio—an idyllic backdrop for fishing, entertaining, or simply enjoying the peace and beauty of the Hudson Valley countryside. Rarely does a property offer this level of privacy, recreation, functionality, and luxury. Whether envisioned as a compound, equestrian estate, entertainer's paradise, or Hudson Valley retreat, this iconic property delivers a lifestyle unlike any other.

95 Judson Road, Montgomery
$899,000
7 Beds ⋅ 5 Baths ⋅ 973605 MLS
A private luxury retreat unlike anything else on the market. Set on 54.10 secluded acres at the end of a long private driveway, 97 Svenski offers an extraordinary combination of privacy, distinctive modern design, smart-home features, and fully renovated, move-in-ready living. This one-of-a-kind residence features 7 bedrooms, 4.5 bathrooms, 1,632+ sq. ft. above grade, plus an additional 1,006 sq. ft. fully finished walkout lower level, creating over 2,600 sq. ft. of thoughtfully finished living space across multiple levels. The open-concept main level is filled with natural light and enhanced by rich hardwood flooring, connecting the living room, dining area, and chef-inspired kitchen. Designed to impress, the kitchen features built-in electric cooking, double ovens, a full-size refrigerator, dishwasher, sleek modern countertops, professional-grade built-in range hood, and a striking skylight centerpiece. Sliding glass doors from the living room, kitchen, and primary suite open to an expansive 435 sq. ft. wraparound deck, creating seamless indoor-outdoor living surrounded by exceptional privacy. The primary suite is a true retreat, featuring a custom built-in bed frame with a dramatic ceiling mirror, private deck access, integrated closet and storage, and smart vanity and toilet features. Its spa-inspired bathroom is complete with a jacuzzi tub and steam shower, creating a relaxing private escape within the home. Upstairs, four spacious bedrooms and two full smart bathrooms are complemented by a one-of-a-kind suspended mesh sitting area overlooking the main level, adding a memorable architectural feature and a distinctive touch of modern design. The fully finished walkout lower level offers an impressive 1,006 sq. ft. of additional living space with the same elevated feel as the floors above. Ideal for guests, extended family, or recreation, this level includes two bedrooms, a full bathroom, recreation room, generous sitting room, polished concrete flooring, hallway wet bar, multiple private walkout entrances, patio access, dedicated utility room, and a full laundry area with washer and dryer. All mechanicals are brand new, including a high-efficiency HVAC system for heating and cooling, a new electric water heater, and a whole-house water softener system. Combining over 54 acres of privacy with modern luxury, smart technology, exceptional entertaining spaces, and truly unique design, 97 Svenski is a rare turnkey retreat created for buyers seeking something extraordinary. Schedule your private showing today.

97 Svenski Road, Montgomery
$739,000
3 Beds ⋅ 3 Baths ⋅ 977565 MLS
Thoughtfully designed, expertly built, and meticulously maintained, this 2003 Stunning Custom built Colonial by Hillside Homes is set on a private 2.2 acre wooded lot on a cul-de-sac in the Winding Oaks Subdivision. With 3400 square feet of modern luxury, this home features a large primary ensuite, two additional bedrooms, a bonus guestroom/study, an upstairs laundry room, and 2.5 bathrooms. The kitchen was fully remodeled in 2022 with modern cabinetry, quartz counter tops and a dual gas top with electric range. Nine-foot ceilings on the main level accentuate a magnificent fireplace in the family room and large upgraded windows, while oak flooring, arched doorways and pocket doors for privacy add elegance throughout the home. A spacious two-car garage includes a modern EV charger, and the side entrance to the home opens to a great built-in mudroom bench and closet for convenience. Downstairs, a walk-out basement offers a splendid recreation room with built-in bookshelves, a spacious office, and a large storage and utility room. The beautifully landscaped property features a well-maintained pool and a large stamped concrete patio making this home great for entertaining. It also features a 12 x 16 custom built shed and a practical fenced-in vegetable garden. Close to schools and shopping with convenient access to Metro North, this elegant home perfectly blends privacy, comfort and convenience, ideal for embracing the peaceful Hudson Valley Lifestyle.

42 Philip Drive, Montgomery
$699,900
4 Beds ⋅ 3 Baths ⋅ 997409 MLS
Set on a quiet cul-de-sac in the Valley Central School District, this newly constructed home offers just under 2,700 sq ft of thoughtfully designed living space on a full acre in one of Montgomery’s most desirable residential settings. Hardwood flooring flows throughout the home, complemented by expansive windows that fill the interior with natural light. The main level features a formal dining area, spacious family room, half bath, and a beautifully appointed kitchen with quartz countertops, recessed lighting, and abundant cabinetry for storage. A separate living room anchored by a sleek linear electric wall-mounted fireplace offers direct access to the private deck, while an additional flexible room is ideal for a home office, sitting room, or guest accommodations. The upper level showcases a spacious primary suite with oversized windows, a walk-in closet, soaking tub, double vanity, separate water closet, and tiled walk-in shower, while three additional bedrooms offer generous proportions and versatility throughout. The walk-out basement provides substantial storage space along with a two-car garage featuring epoxy flooring and quiet electric garage door openers. Conveniently located near local restaurants, boutique shopping, wineries, farm markets, parks, City Winery Hudson Valley, Angry Orchard, and the Orange County Arboretum, the property also offers easy access to I-84, Route 17/I-86, Stewart International Airport, and Metro-North connections, making it an appealing option for commuters seeking modern Hudson Valley living approximately 70 minutes from New York City.

24 Francis Harrison 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
$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
$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
$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
$999,999
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
$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
$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
board logo

© 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.