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2031 State Route 17K, Montgomery
$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

21 Francis Harrison Court, Montgomery
$699,900
4 Beds ⋅ 3 Baths ⋅ 1055225 MLS
Your search for a beautiful new home in the Hudson Valley may have just come to an end. Located on a peaceful cul-de-sac in Montgomery and set on a spacious one-acre property, this newly built home offers nearly 2,700 square feet of beautifully finished living space, generous rooms, and a layout designed to accommodate both relaxed family living and entertaining. From the moment you enter, you'll appreciate the bright, inviting atmosphere created by large windows and beautiful hardwood flooring throughout the main living areas. The thoughtfully designed floor plan offers an ideal balance of open gathering spaces and private areas, providing flexibility for today's lifestyle. The impressive kitchen is designed to be both stylish and functional, featuring elegant quartz countertops, abundant cabinetry, recessed lighting, and plenty of preparation and storage space. It opens naturally to the spacious family room, creating a comfortable setting for everyday living and entertaining. A formal dining area provides the perfect space for holiday gatherings and special occasions. A versatile additional room on the main level can easily adapt to your needs and would make an ideal home office, study, sitting room, playroom, or guest space. A convenient half bath completes the main level. Upstairs, the spacious primary suite provides a private retreat at the end of the day. The luxurious en-suite bathroom features a relaxing soaking tub, double vanity and beautifully tiled walk-in shower. A generous walk-in closet provides excellent storage, while oversized windows bring in natural light and create an airy, comfortable feel. Three additional bedrooms offer plenty of space for family members, guests, or additional office and hobby needs. The upper level is completed by a well-appointed full bathroom and thoughtfully designed spaces that provide both comfort and versatility. The walk-out lower level adds valuable flexibility and substantial storage space. The attached two-car garage features durable epoxy flooring and quiet electric garage door openers, providing a clean, functional space for vehicles, equipment, and additional storage. Outside, the full-acre setting offers room to enjoy the privacy and peaceful surroundings. The cul-de-sac location provides a quieter residential atmosphere while remaining conveniently close to everything Montgomery and the surrounding Hudson Valley have to offer. Enjoy easy access to local restaurants, charming shops, wineries, farm markets, parks, City Winery Hudson Valley, Angry Orchard, and the Orange County Arboretum. For commuters, the property is conveniently located near major highways I-84, I-87, Stewart International Airport, and Metro-North connections. Offering the benefits of brand-new construction, an expansive floor plan, modern finishes, a private one-acre setting, and a convenient Hudson Valley location, this exceptional Montgomery home is ready to welcome its next owners.

21 Francis Harrison Court, Montgomery

8 Acorn Drive, Montgomery
$675,000
4 Beds ⋅ 3 Baths ⋅ 1053066 MLS
Welcome Home! Set on approximately 1.9 acres, this spacious bi-level home offers an impressive 3,062 square feet of living space with 4 bedrooms, 3 full bathrooms, two large sheds and an attached 2-car garage. Step inside to a thoughtfully designed layout with generous living spaces and plenty of room to make the home your own. The recently remodeled kitchen brings a fresh, updated feel to the heart of the home and flows naturally into the dining area, while the large living room provides an inviting setting for both everyday living and entertaining. The home offers four generously sized bedrooms, with three featuring walk-in closets, an exceptional amount of storage and a feature not often found throughout multiple bedrooms. Three full bathrooms add convenience across the home's spacious bi-level layout. Just off the rear patio, a bonus sitting room creates another inviting space to relax, entertain, or enjoy the connection between the home's interior and outdoor areas. With multiple living and gathering spaces throughout, the layout offers excellent flexibility to adapt to a variety of needs. Outside, approximately 1.9 acres provide plenty of room to enjoy the property, whether you're spending time on the patio, entertaining outdoors, or simply appreciating the additional space surrounding the home. The attached 2-car garage provides everyday convenience along with additional storage possibilities.

8 Acorn Drive, Montgomery

9 Union School Road, Montgomery
$629,900
4 Beds ⋅ 3 Baths ⋅ 1051813 MLS
NEW CONSTRUCTION IN THE VALLEY CENTRAL SCHOOL DISTRICT—READY TO MOVE IN. This affordable, practical four-bedroom home offers three full bathrooms, more than 2,000' square feet of living space, central air, a propane fireplace, a two-car garage, and a newly graded and seeded yard. Concrete walkways lead to a covered front porch and an inviting main entrance. Inside, the spacious foyer provides direct access to the family room featuring a propane fireplace with ceramic-tiled accents, a wood mantel, recessed lighting, and a sliding door to the backyard. Nearby is the laundry room with window, a full bathroom with ceramic-tile flooring and a tub, plus a private first-floor bedroom. A few steps up to the next level opens to an impressive floor plan with 12-foot ceilings, abundant natural light, and recessed lighting. The kitchen includes an island, pantry, quartz countertops, soft-close drawers and cabinet doors, under-cabinet lighting, all appliances, with propane range. The second floor has full bathroom with tub and ceramic-tile flooring, along with two cozy bedrooms with hardwood floors. The primary bedroom features hardwood flooring, a lighted walk-in closet, and a private bathroom with a ceramic-tile shower and flooring. The home also offers three heating zones—one on each level—central air throughout, and a spacious two-car garage with automatic openers. Short drive to the local golf course make this location special in many ways.

9 Union School Road, Montgomery

104 Ayers Court, Montgomery
$529,000
3 Beds ⋅ 3 Baths ⋅ 1050379 MLS
Offering first-time-on-the-market quality, this well-maintained raised ranch sits on a quiet cul-de-sac in a peaceful Village of Montgomery neighborhood. Cherished and impeccably cared for by its original owners, this 3-bedroom, 3-bath home spans approximately 2,504 square feet of flexible living space, highlighted by soaring cathedral ceilings that create an open, airy atmosphere. The primary main level blends comfort and function, while the fully finished lower level offers versatile bonus rooms tailored for a home office, gym, or recreation space. Three full bathrooms (two with soaking tubs, one with a shower stall) ensure convenience for relatives and guests, alongside a dedicated lower-level laundry room with washer and dryer hookups. Central air conditioning keeps the home comfortable year-round. Step out back to your private outdoor oasis designed for ultimate entertaining. The fully equipped yard features a large, heated above-ground pool, an expansive deck, a cozy covered seating area, and additional patio space. A convenient storage shed keeps lawn care and pool equipment tucked away cleanly. Situated in the desirable Valley Central School District, you are just minutes from the charming shops, local dining, and vibrant community amenities of the Village of Montgomery. A rare opportunity to own a meticulously kept, original-owner home with an exceptional outdoor setup!

104 Ayers Court, Montgomery

392 Bailey Road, Montgomery
$714,999
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

960 County Route 17, Montgomery
$824,999
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! Bring your vision of a horse property to life with room to imagine pastures, paddocks and a barn of your own. 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

77 Union Street, 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

49 Bailey Road, 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

64 W Corbett 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

83 Little Collabar Road, 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

250 Corbett Road, Montgomery
$999,000
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

272 Beaver Dam Road, Montgomery
$674,999
4 Beds ⋅ 4 Baths ⋅ 1025068 MLS
The original owners say it's time to move and pass this home to new owners. This property sits on 1.36 acres and offers over 2500 sq feet of living space. It has 2 primary bedrooms one on the first floor which has an its own bathroom and laundry. Upstairs is another primary bedroom 2 additional bedrooms, laundry, a bathroom and bonus space. Use your imagination and use it how you want to. There is a full front porch you can sit and drink your morning coffee. If you don't want to sit there sit out on the back deck that is located off the dining room. The Kitchen is open up to the living room. This home offers a lot of natural light. it is close to i84 for commuters, local shops and 208,17k. This home is energy effect with geothermal heating and cooling. Also, feeds the hot water. High ceiling throughout and a full unfinished basement with bilco doors. Plenty of room for storage.

272 Beaver Dam Road, Montgomery

165 Benedict Road, Montgomery
$724,999
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 plus office, 2.5-bathroom Colonial/Farmhouse-style home is situated on 3 acres boasting the utmost 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. In addition to the three bedrooms, the main level thoughtfully features a dedicated office or study with rich wood flooring and crown molding, perfect for working from home, 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 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

27 Grosso Court, Montgomery
$724,000
4 Beds ⋅ 3 Baths ⋅ 1018110 MLS
Private 6.5-acre Victorian retreat with heated salt water pool! Tucked away on a quiet cul-de-sac, this impressive home features a dramatic two-story foyer, soaring ceilings, creates a grand first impression and leads to spacious living areas throughout the home and a flexible floor plan with exceptional potential on each floor including the walk out basement. Enjoy scenic views, generous indoor and outdoor living, and a prime location just minutes from shopping, dining, and Woodbury Common Premium Outlets. The main level features a generously sized formal dining room, ideal for entertaining, holiday gatherings, and everyday living. A private den or home office provides the perfect space for remote work, studying, or a quiet retreat. One of the home’s standout features is the expansive bonus room, larger than the primary suite and complete with its own private entrance. This versatile space offers endless possibilities, whether used for multigenerational living, guest accommodations, a second home office, a media or game room, fitness studio, or creative workspace. The spacious eat-in kitchen provides ample room for casual dining and opens directly to a deck overlooking the above ground pool and the breathtaking natural surroundings. Enjoy peaceful mornings, outdoor dining, and unforgettable sunsets while taking in the beauty and privacy of approximately 6.5 acres. The expansive property also offers room for future enhancements or expansion. A conveniently located first-floor laundry room with a utility sink adds everyday practicality and convenience. The spacious primary suite serves as a private retreat, showcasing a distinctive octagonal tray ceiling, an en-suite bathroom, and an oversized walk-in closet with abundant storage. The walk-out basement expands the home’s possibilities by providing direct access to the outdoor patio, creating a seamless connection between indoor and outdoor living while offering additional space for recreation, entertaining, or future finishing. The shed presents an exciting opportunity to create a charming pool cabana, hobby space or workshop. Additional highlights include above-ground oil heating and an attached two-car garage. Whether you’re searching for privacy, versatility, scenic surroundings, or room to grow, this exceptional Victorian estate offers a rare opportunity to create the lifestyle you’ve been dreaming of. Make an appointment for a private tour and experience this beauty for yourself!

27 Grosso Court, Montgomery

11 Kevin Court, 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

97 Svenski Road, Montgomery
$875,000
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

42 Philip Drive, 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

24 Francis Harrison Court, 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

68 Weaver Street, 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

65 Judson Road, 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

555 State Route 416, 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

294 Comfort Trail, 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

46 Union Street, 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

265 Goodwill Road, 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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