Montgomery Homes with Pine Bush School district

Welcome to Montgomery, New York—a charming town nestled in the picturesque Orange County, where the beauty of nature meets the warmth of community. Known for its rich history and stunning landscapes, Montgomery offers a delightful blend of small-town charm and modern convenience. With its scenic views, lush parks, and friendly atmosphere, it's no wonder that Montgomery is a sought-after destination for families and individuals alike.

One of the standout features of this lovely town is its connection to the highly regarded Pine Bush School District. Families looking to settle down will appreciate the district's commitment to academic excellence and holistic development. With dedicated educators and a variety of extracurricular activities, Pine Bush schools provide a nurturing environment that fosters growth and learning, ensuring that children receive a quality education that prepares them for future success.

Real estate in Montgomery offers a diverse range of homes, from cozy single-family residences to spacious properties with sprawling yards—perfect for those who enjoy outdoor living. Many of these homes are situated in tranquil neighborhoods, where you can enjoy peaceful evenings while being just a short drive from local amenities, shopping, and dining options.

In addition to its family-friendly atmosphere and excellent school district, Montgomery is conveniently located near major highways, making it easy to commute to nearby cities while still enjoying the serenity of suburban life. Whether you’re a first-time homebuyer or looking to upgrade, Montgomery is a community that welcomes you with open arms and endless possibilities. Come explore the charm of Montgomery and discover your dream home today!

Newest Montgomery Homes with Pine Bush School district

$499,000

3 Beds ⋅ 3 Baths ⋅ 1023226 MLS

Come see all the great features this home has to offer. The main living area offers three bedrooms, two full baths, a spacious living room, and a large eat in kitchen which connects to a large deck. The lower level has multiple finished rooms that offer endless possibilities. There is storage space, a full bathroom, washer/dryer, and a connected garage all on the lower level. The lower level has a walk out onto a concrete patio that is covered by the large second store deck. These two outdoor spaces make this home feel even larger than it is and offer a great space for entertaining and outside leisure activities. A long garage with room for multiple vehicles, tankless water heater, water treatment system, pull down stairs to the attic, extensive cabinets, freshly painted deck, invisible dog fence, and wood burning stove are some of the many amazing features this home has to offer. Come book your showing today!

326 Bullville Road, 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

$675,000

3 Beds ⋅ 2 Baths ⋅ 1012189 MLS

Charming, authentic Farmhouse, maintaining plenty of rustic charm with some exposed hand hewn beams, but with every modern update. Private in ground pool, big bonus room over garage, all systems updated or replaced. Central air, new septic tank. Fully furnished for the right buyer. Photos dont do it justice. This home is warm and interesting, you will be refreshed. Just had major price reduction. COME AND SEE!

291 Comfort Trail, Montgomery

$449,900

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. 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

$519,000

4 Beds ⋅ 3 Baths ⋅ 1007894 MLS

Priced to sell and fully available. Come see this beautiful, recently and tastefully refreshed 8 room, 4 bedroom, 2.5 bath, 1800 sq. ft. colonial, perched atop a lovely, private, 1.5 acre property, in an area of upscale homes and in the Pine Bush School District. It features an open floor plan on the first level with superb kitchen, 4 year old stainless steel appliances, granite countertops, with breakfast nook that opens to a large, gracious,gathering/entertainment room, formal dining room with hardwood floors & spacious living room. There is a primary bedroom on the second level with primary bath with shower, 3 other bedrooms & bath with tub. Recently painted, new roof in 2012, professionally landscaped in the front, paver patio in the back to barbeque or enjoy nature, and fenced back yard. Close to great Montgomery Village shopping, restaurants & shops, City Winery, Winding Hill Park & golf course & more. Also close to major malls, mediical facilities , hospital, supermarkets in Middletown. Why wait? Start enjoying life.

7 Judson Road, Montgomery

$546,900

6 Beds ⋅ 4 Baths ⋅ 1006008 MLS

"We know this property is worth more, but we're letting the market decide! Welcome to 145 Youngblood Road, a rare opportunity where endless possibilities meet peaceful country living. This oversized ranch style home offers exceptional flexibility with a separate apartment above the garage, creating the perfect setup for multigenerational living, owner occupied investment opportunities, guest accommodations, or additional rental income. Nestled in a serene setting, this property is much more than a home. It is a true opportunity property. Previously operating as a highly successful Airbnb with SUPERHOST status, the home enjoyed strong occupancy and consistent demand throughout the year. Today, it remains an attractive option for long term or mid term rentals and has generated interest from companies seeking housing accommodations for employees and contractors. Adding to its appeal, the property is zoned Residential/Mixed Use Commercial, opening the door for a variety of potential uses. Whether you are looking to establish a home based business, create a multigenerational compound, generate rental income, or simply enjoy the abundance of living space, this property offers flexibility that is increasingly difficult to find. Inside, you will discover spacious rooms, multiple bathrooms, and a floor plan designed to accommodate a variety of lifestyles. Outside, enjoy the peace and privacy that make this property such a sought after destination. The sellers are motivated and ready to pass this unique opportunity on to the next owner. Whether you are an investor, entrepreneur, or homeowner seeking space and versatility, 145 Youngblood Road delivers the rare chance to own what feels like two homes in one. Bring your vision, bring your ideas, and unlock the tremendous potential this property has to offer.

145 Youngblood 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

$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

$1,145,000

4 Beds ⋅ 3 Baths ⋅ 975612 MLS

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

170 Dickerson Avenue, Montgomery

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