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$479,900

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!

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

$499,999

Full of classic character and versatility, this mother-daughter home at 77 Union Street offers a fantastic opportunity for investors or owner-occupants alike, located in the Valley Central School District. The property features a spacious 3-bedroom unit alongside a comfortable 1-bedroom efficiency, ideal for generating rental income or providing space for extended 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 3-bedroom unit 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 multi-unit flexibility.

4 Beds ⋅ 3 Baths ⋅ 1032648 MLS

Full of classic character and versatility, this mother-daughter home at 77 Union Street offers a fantastic opportunity for investors or owner-occupants alike, located in the Valley Central School District. The property features a spacious 3-bedroom unit alongside a comfortable 1-bedroom efficiency, ideal for generating rental income or providing space for extended 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 3-bedroom unit 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 multi-unit flexibility.

77 Union Street, Montgomery

$669,000

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.

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

$1,250,000

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.

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

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.

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

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.

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

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.

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

$449,000

AVAILABLE! Welcome to this beautifully renovated 3-bedroom ranch set on a private 1-acre lot in Hamptonburgh, directly across from Thomas Bull Memorial Park. recently renovated and move-in ready, this home features refinished hardwood flooring, a bright updated kitchen with casual dining area, 1 full bath, new roof, new siding, and a charming new front porch. new driveway, new ductless air conditioning and heating units, freshly painted. The covered rear deck is perfect for relaxing, entertaining, or simply enjoying the peaceful surroundings. A large detached 2-car garage with water and electric provides excellent space for parking, storage, hobbies, or a workshop. With its fresh updates, inviting layout, and scenic location near parks, recreation, and commuter conveniences, this home is a wonderful Hudson Valley find.

3 Beds ⋅ 1 Baths ⋅ 1018676 MLS

AVAILABLE! Welcome to this beautifully renovated 3-bedroom ranch set on a private 1-acre lot in Hamptonburgh, directly across from Thomas Bull Memorial Park. recently renovated and move-in ready, this home features refinished hardwood flooring, a bright updated kitchen with casual dining area, 1 full bath, new roof, new siding, and a charming new front porch. new driveway, new ductless air conditioning and heating units, freshly painted. The covered rear deck is perfect for relaxing, entertaining, or simply enjoying the peaceful surroundings. A large detached 2-car garage with water and electric provides excellent space for parking, storage, hobbies, or a workshop. With its fresh updates, inviting layout, and scenic location near parks, recreation, and commuter conveniences, this home is a wonderful Hudson Valley find.

230 Route 416, Montgomery

$349,999

Welcome to this charming Ranch-style home beautifully nestled on a corner lot in the Village of Montgomery within the Valley Central School District. Showcasing lovely curb appeal with a landscaped front yard, this inviting 1-bedroom, 1-bathroom residence features a versatile office or bonus room to suit your lifestyle. Step inside to discover a bright living room highlighted by gleaming hardwood floors and a cozy corner wood-burning stove resting on a tiled hearth. The spacious, eat-in kitchen boasts rustic wood cabinetry, a decorative backsplash, and ample space for cooking and dining. The well-appointed full bathroom provides a large vanity, tile flooring, and a step-in shower. The living spaces extend into comfortable sleeping and working quarters, including a vibrant bonus room with sliding glass doors leading to the exterior, as well as a spacious primary bedroom featuring large windows and beautiful hardwood floors. Downstairs, a full basement offers excellent storage or expansion potential. Outside, enjoy relaxing or entertaining on the expansive side deck, which overlooks a level, partially fenced yard area. The property also features an attached two-car garage with plenty of interior workspace and an additional detached storage shed for your convenience. Ideally located just two blocks from Veterans Memorial Park and the Village center—which features a variety of eateries, shopping boutiques, local pubs, and the Village hall—this home also provides fantastic commuter convenience, situated close to Route 211, Route 17K, and just a 10-minute drive to Interstate 84.

1 Beds ⋅ 1 Baths ⋅ 1017517 MLS

Welcome to this charming Ranch-style home beautifully nestled on a corner lot in the Village of Montgomery within the Valley Central School District. Showcasing lovely curb appeal with a landscaped front yard, this inviting 1-bedroom, 1-bathroom residence features a versatile office or bonus room to suit your lifestyle. Step inside to discover a bright living room highlighted by gleaming hardwood floors and a cozy corner wood-burning stove resting on a tiled hearth. The spacious, eat-in kitchen boasts rustic wood cabinetry, a decorative backsplash, and ample space for cooking and dining. The well-appointed full bathroom provides a large vanity, tile flooring, and a step-in shower. The living spaces extend into comfortable sleeping and working quarters, including a vibrant bonus room with sliding glass doors leading to the exterior, as well as a spacious primary bedroom featuring large windows and beautiful hardwood floors. Downstairs, a full basement offers excellent storage or expansion potential. Outside, enjoy relaxing or entertaining on the expansive side deck, which overlooks a level, partially fenced yard area. The property also features an attached two-car garage with plenty of interior workspace and an additional detached storage shed for your convenience. Ideally located just two blocks from Veterans Memorial Park and the Village center—which features a variety of eateries, shopping boutiques, local pubs, and the Village hall—this home also provides fantastic commuter convenience, situated close to Route 211, Route 17K, and just a 10-minute drive to Interstate 84.

36 Charles Street, Montgomery

$675,000

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!

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

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!

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

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.

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

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.

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

"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.

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

$975,000

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.

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

$699,000

Welcome to 41 Philip Drive, a beautifully maintained Colonial built by Hillside Homes and set within Montgomery’s desirable Winding Oaks subdivision. Located on a quiet cul-de-sac and positioned on a private, landscaped lot backing to woods, this home offers exceptional curb appeal with a long paved driveway, mature trees, and a peaceful residential setting. Inside, the home features a bright, comfortable layout with hardwood floors, abundant natural light, and inviting spaces designed for everyday living and entertaining. The open kitchen and breakfast area include warm wood cabinetry, generous counter space, recessed lighting, a center island with seating, and sliding glass doors that extend the living space outdoors. The kitchen flows naturally into the surrounding living and dining areas, creating an ideal environment for gathering. The spacious family room enhances the home’s appeal with hardwood floors, a vaulted ceiling, ceiling fan, large windows, and a welcoming fireplace that anchors the room. A formal dining area provides an elegant setting for meals and celebrations, while the overall floor plan offers flexibility for work, relaxation, and hosting. The primary suite includes a private bath with double sinks for added comfort and convenience. The finished lower level adds approximately 1,200 square feet of versatile bonus space, offering multiple rooms ideal for a media room, playroom, fitness area, office, hobby space, or guest accommodations, complete with an additional full bathroom. Outdoors, the property features a fully usable backyard bordered by mature woods, creating a private and picturesque setting. Expansive lawn areas and established landscaping offer ample room for recreation, gardening, outdoor dining, or simply enjoying the tranquility of the surroundings. A whole-house generator adds valuable peace of mind year-round. Located in the scenic Hudson Valley, this home provides convenient access to Montgomery’s shopping, dining, parks, schools, commuter routes, and regional attractions. With its timeless design, generous living spaces, wooded privacy, and inviting indoor-outdoor flow, 41 Philip Drive presents an exceptional opportunity in one of Montgomery’s most sought-after neighborhoods.

4 Beds ⋅ 4 Baths ⋅ 1002140 MLS

Welcome to 41 Philip Drive, a beautifully maintained Colonial built by Hillside Homes and set within Montgomery’s desirable Winding Oaks subdivision. Located on a quiet cul-de-sac and positioned on a private, landscaped lot backing to woods, this home offers exceptional curb appeal with a long paved driveway, mature trees, and a peaceful residential setting. Inside, the home features a bright, comfortable layout with hardwood floors, abundant natural light, and inviting spaces designed for everyday living and entertaining. The open kitchen and breakfast area include warm wood cabinetry, generous counter space, recessed lighting, a center island with seating, and sliding glass doors that extend the living space outdoors. The kitchen flows naturally into the surrounding living and dining areas, creating an ideal environment for gathering. The spacious family room enhances the home’s appeal with hardwood floors, a vaulted ceiling, ceiling fan, large windows, and a welcoming fireplace that anchors the room. A formal dining area provides an elegant setting for meals and celebrations, while the overall floor plan offers flexibility for work, relaxation, and hosting. The primary suite includes a private bath with double sinks for added comfort and convenience. The finished lower level adds approximately 1,200 square feet of versatile bonus space, offering multiple rooms ideal for a media room, playroom, fitness area, office, hobby space, or guest accommodations, complete with an additional full bathroom. Outdoors, the property features a fully usable backyard bordered by mature woods, creating a private and picturesque setting. Expansive lawn areas and established landscaping offer ample room for recreation, gardening, outdoor dining, or simply enjoying the tranquility of the surroundings. A whole-house generator adds valuable peace of mind year-round. Located in the scenic Hudson Valley, this home provides convenient access to Montgomery’s shopping, dining, parks, schools, commuter routes, and regional attractions. With its timeless design, generous living spaces, wooded privacy, and inviting indoor-outdoor flow, 41 Philip Drive presents an exceptional opportunity in one of Montgomery’s most sought-after neighborhoods.

41 Philip Drive, Montgomery

$649,900

Two adjacent properties offered together as a single opportunity (2056 & 2060 Rt 17K): a preserved 1840 historic farmhouse paired with a separate 2-bedroom residence, with a combined total of approximately 4 acres, 6 bedrooms, 4 baths, and roughly 2,500 square feet of combined living space in Montgomery's Town of Crawford. Built in 1840 and preserved with rare integrity by just two families in almost 200 years, the 4 bedroom primary farmhouse delivers the kind of atmosphere that new construction cannot replicate. Hand-hewn beams, ultra-wide plank floors, natural woodwork, and four fireplaces anchor the home's historic character throughout the kitchen, living room, primary bedroom, and basement. Thoughtfully maintained rather than modernized into anonymity, the 1,704-square-foot residence blends authentic craftsmanship with practical comfort, including updated windows, modern heating, and a large rear deck that wraps the L-shaped footprint and opens toward the kitchen garden and wooded views across the combined acreage. The second parcel adds a separate 2-bedroom, 1-bath residence with its own entrance, porch, and utilities. Previously rented, it offers flexibility as income-producing space, extended family housing, guest quarters, or private workspace. A 1,200-square-foot pole barn adds additional utility for storage, workshop use, equipment, or creative pursuits. Valley Central School District. No HOA. For the buyer who understands that authenticity cannot be recreated, this is a true Hudson Valley farmhouse property with flexibility, income potential, and preserved historic character. Please note; Taxes, beds, baths and acreage are the combined totals of both properties.

6 Beds ⋅ 4 Baths ⋅ 999867 MLS

Two adjacent properties offered together as a single opportunity (2056 & 2060 Rt 17K): a preserved 1840 historic farmhouse paired with a separate 2-bedroom residence, with a combined total of approximately 4 acres, 6 bedrooms, 4 baths, and roughly 2,500 square feet of combined living space in Montgomery's Town of Crawford. Built in 1840 and preserved with rare integrity by just two families in almost 200 years, the 4 bedroom primary farmhouse delivers the kind of atmosphere that new construction cannot replicate. Hand-hewn beams, ultra-wide plank floors, natural woodwork, and four fireplaces anchor the home's historic character throughout the kitchen, living room, primary bedroom, and basement. Thoughtfully maintained rather than modernized into anonymity, the 1,704-square-foot residence blends authentic craftsmanship with practical comfort, including updated windows, modern heating, and a large rear deck that wraps the L-shaped footprint and opens toward the kitchen garden and wooded views across the combined acreage. The second parcel adds a separate 2-bedroom, 1-bath residence with its own entrance, porch, and utilities. Previously rented, it offers flexibility as income-producing space, extended family housing, guest quarters, or private workspace. A 1,200-square-foot pole barn adds additional utility for storage, workshop use, equipment, or creative pursuits. Valley Central School District. No HOA. For the buyer who understands that authenticity cannot be recreated, this is a true Hudson Valley farmhouse property with flexibility, income potential, and preserved historic character. Please note; Taxes, beds, baths and acreage are the combined totals of both properties.

2056 State Route 17K, Montgomery

$769,900

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.

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

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.

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

$449,900

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.

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

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.

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

$449,900

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.

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

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!!!

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

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.

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

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.

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