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$479,900
3 Beds 2 Baths 1026792 MLS
LOVELY HOME IN THE VILLAGE OF MONTGOMERY WITH RIVER VIEWS! This well maintained 1770 sq.ft. , 3 bedroom, 2 bathroom home has a lot to offer; an open floor plan with a spacious deck, with an awning, for entertaining or just relaxing and enjoying the river view. Stepping downstairs you will find a finished family room plus the 12x20 finished bonus room, Ideal for an office, game room, play room, fitness room or whatever fits your individual needs. Let's not stop there, there is a large unfinished area-great for storage. All this and it includes a cedar closet, a shed, and a freezer. Close to schools, parks, shopping, major highways, restaurants and all the charm the Village has to offer. COME TAKE A LOOK -YOU WON"T BE DISAPPOINTED!

168 Pleasant Avenue, Montgomery

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

83 Little Collabar Road, Montgomery

$1,250,000
4 Beds 5 Baths 1025121 MLS
Set on 11.9 private, wooded acres with sweeping easterly views toward the Hudson River ridgeline, this French Country-inspired estate blends old-world architecture with modern comfort. A dramatic turret, multiple gables, and an arched stone entry portico set the tone before you even step inside. A soaring two-story foyer welcomes you home, with a custom wrought-iron and oak staircase leading to an open catwalk overlooking the great room below. The great room itself impresses with a vaulted, beamed ceiling, a stone-mantled gas fireplace, and a wall of French doors framing long-range views. A formal dining room with designer Venetian plaster-style walls and an arched picture window offers an elegant space for entertaining, flowing easily into the gourmet kitchen, where a professional 6-burner gas range, oversized granite island, custom oak cabinetry, and a sun-filled eat-in dining area create a true chef's kitchen. The first-floor primary suite is a private retreat, with French doors opening to the wraparound deck, a spa-style bathroom featuring a corner jacuzzi tub, dual-sink vanity, glass walk-in shower, and radiant heated floors for year-round comfort. The finished lower level extends the home's entertaining possibilities with a full wet bar, a double-sided wood-burning fireplace shared with the family room, a dedicated home theater, a cedar-lined sauna, an exercise room, a full bathroom, and a versatile bonus room ideal as a den, guest space, or office. Outside, enjoy a wraparound deck connecting to the primary suite, a screened-in sitting area, and a hot tub included in the sale, all overlooking a private, tree-lined setting. A whole-house backup generator, Buderus high-efficiency heating system, radon mitigation system, and Andersen windows and doors round out this thoughtfully maintained home. Additional highlights include a second-floor ensuite, a home office, and a spacious bonus room over the garage. This is a rare opportunity to own a private, amenity-rich retreat just minutes from the Village of Montgomery's shops, restaurants, and parks, with easy access to commuting routes throughout the Hudson Valley.

250 Corbett Road, Montgomery

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

123 Collabar Road, Montgomery

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

272 Beaver Dam Road, Montgomery

$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

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

165 Benedict Road, Montgomery

$449,000
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
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

$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

$699,000
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

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

42 Philip Drive, Montgomery

$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

$449,900
4 Beds 2 Baths 984326 MLS
Welcome to 555 State Route 416 in the heart of Montgomery, NY—Enjoy Village Charm and country life!!! This spacious 4-bedroom, 2-bath home offers comfortable living with plenty of room to grow. Enjoy an inviting eat-in kitchen featuring new stainless steel appliances, a dedicated dining area, and a large living room perfect for family gatherings and entertaining. An unfinished, easily accessible basement provides ample storage space and potential for future use. Additional highlights include central air conditioning, a generator hookup, a breezeway connecting to the garage, and a shed for extra storage. The property also boasts a large, flat backyard—ideal for outdoor entertaining, gardening, or relaxing. Conveniently located near shops, restaurants, schools, and parks, this home offers the perfect balance of convenience and tranquility. Ice Shield wiring installed to protect Roof.

555 State Route 416, Montgomery

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

198 Corbett Road, Montgomery

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