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Homes for Sale in 12549

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  • /34

    $899,900

    $50K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 3,668 Sq Ft

    41 Fern Wood Way, Montgomery, NY 12549

    Nestled within the sought-after Winding Hills Estates, this exceptional home is set on a quiet cul-de-sac and backs directly to the rolling greens of the picturesque Winding Hills Golf Course, an executive 18-hole course surrounded by manicured landscaping. From the moment you arrive, the home impresses with Hardie board siding, a metal roof, blacktopped driveways, paver walkways, covered front

    Agent Photo

    Chris Ogden

    Realty Promotions Inc

    (845) 493-3644

    41 Fern Wood Way, Montgomery, NY 12549
  • /50

    $499,900

    • 3 Beds
    • 1.5 Baths
    • 2,212 Sq Ft

    5319 Searsville Rd, Pine Bush, NY 12566

    Welcome to this beautifully maintained and updated home, located on a quiet country road in Pine Bush, NY, on nearly an acre of property. This lovely home offers 3 bedrooms, 1.5 bathrooms, a 2-car garage, and hardwood floors throughout. The updated kitchen features stainless steel appliances, granite countertops, and easy access to a charming three-season enclosed room. The warm and inviting

    Agent Photo

    Dulce M Ferrera

    KW Hudson Valley Untied

    (845) 681-6622

    5319 Searsville Rd, Pine Bush, NY 12566
  • /45

    $874,999

    • 3 Beds
    • 2 Baths
    • 1,796 Sq Ft

    294 Comfort Trail, Montgomery, NY 12549

    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

    Agent Photo

    Richard Baxter

    Keller Williams Realty

    (845) 622-8077

    294 Comfort Trail, Montgomery, NY 12549
  • /50

    $649,900

    • 6 Beds
    • 4 Baths
    • 2,488 Sq Ft

    2056 State Route 17k, Montgomery, NY 12549

    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

    Matthew Morreale

    J. Morreale, LTD

    (845) 552-9678

    2056 State Route 17k, Montgomery, NY 12549
  • /49

    $719,900

    $19K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,011 Sq Ft

    41 Philip Dr, Montgomery, NY 12549

    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,

    Antoinette Caruso Stonewall Realty Group LLC

    41 Philip Dr, Montgomery, NY 12549
  • /49

    $679,900

    • 4 Beds
    • 2.5 Baths
    • 2,168 Sq Ft

    30 Wavey Willow Ln, Montgomery, NY 12549

    Welcome to this beautifully renovated 4-bedroom, 2.5-bath Colonial that perfectly blends timeless charm with modern updates. From top to bottom, this home has been completely renovated and thoughtfully updated, offering truly move-in-ready living. The spacious floor plan features bright, sun-filled rooms, a stunning updated kitchen, beautifully renovated bathrooms, and quality finishes

    Paul Biagini Biagini Realty

    30 Wavey Willow Ln, Montgomery, NY 12549
  • /20

    $399,000

    • 2 Beds
    • 1 Bath
    • 928 Sq Ft

    1084 State Route 17k, Montgomery, NY 12549

    Enjoy peaceful living in this charming, newly updated private ranch set on over one acre of beautiful property. This inviting home offers the perfect blend of comfort and convenience, featuring a beautifully renovated kitchen and bathroom with modern finishes throughout. A new roof adds additional value and peace of mind.Imagine having a golf course right in your backyard! This property

    Larry Curasi Curasi Realty, Inc.

    1084 State Route 17k, Montgomery, NY 12549
  • /32

    $269,000

    $11K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 584 Sq Ft

    20 Barron Rd, Montgomery, NY 12549

    Newly added! A Pioneer mini split for central air (comes thru existing ducts)! And, the exterior has been freshly painted! This sweet ranch is perfect for 1st time home buyers, or people that just like to have really low living expenses! You'll enjoy the large deck off the kitchen for enjoying BBQ's or hanging outside. You'll also enjoy the small & quiet neighborhood! At the end of Barron Rd, is

    Kathy Dawson Howard Hanna Rand Realty

    20 Barron Rd, Montgomery, NY 12549
  • /38

    $474,999

    $24K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,734 Sq Ft

    555 State Route 416, Montgomery, NY 12549

    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

    Nancy Sayegh Coldwell Banker Realty

    555 State Route 416, Montgomery, NY 12549
  • /2

    $499,000

    $60K PRICE DROP
    • Land
    • 7.6 Acres
    • $65,658 per Acre

    0 New York 17k, Montgomery, NY 12549

    Introducing a prime commercial investment opportunity on State Rt 17K, Montgomery, NY, 12549. Comprised of two lots togther - Apn #334289-027-000-0005-003.000-0000 9 (6.6 acres) and Apn#334289-027-000-0005-002.000-0000 (one acre) this 7.6-total acre property, zoned B4 Highway Commercial, offers exceptional potential for a multitude of uses. With 600 Ft of highway frontage and a signalized

    Jay Feinberg KW Hudson Valley Untied

    0 New York 17k, Montgomery, NY 12549
  • /50

    $2,499,900

    • 3 Beds
    • 3 Baths
    • 3,448 Sq Ft

    95 Judson Rd, Montgomery, NY 12549

    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

    Danielle Bartula Howard Hanna Rand Realty

    95 Judson Rd, Montgomery, NY 12549
  • /36

    $599,000

    • 6 Beds
    • 3.5 Baths
    • 4,760 Sq Ft

    145 Youngblood Rd, Montgomery, NY 12549

    "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

    Anesha Nesbitt eXp Realty

    145 Youngblood Rd, Montgomery, NY 12549
  • /25

    $675,000

    • 5 Beds
    • 3 Baths
    • 2,982 Sq Ft

    40 Bailey Rd, Montgomery, NY 12549

    Welcome to this exceptional ranch-style home offering the perfect combination of space, versatility, and lifestyle. Thoughtfully designed and currently configured as a sprawling single-family residence, this home provides an ideal setup for today's multi-generational living with separate areas that offer both privacy and togetherness. The main level features 3 spacious bedrooms, 2 full baths, an

    Nancy LaBarbera KW Hudson Valley Untied

    40 Bailey Rd, Montgomery, NY 12549
  • /50

    $975,000

    Open Sun 11AM - 12:30PM
    • 7 Beds
    • 4.5 Baths
    • 1,632 Sq Ft

    97 Svenski Rd, Montgomery, NY 12549

    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.

    Leon Klein Keller Williams Hudson Valley

    97 Svenski Rd, Montgomery, NY 12549
  • /35

    $499,000

    • 5 Beds
    • 2.5 Baths
    • 2,360 Sq Ft

    82 Wallkill Ave, Montgomery, NY 12549

    LOVELY HISTORIC HOME IN THE VILLAGE OF MONTGOMERY! This 2360 sq.ft. home has a lot to offer, historical charm with hardwood floors, an old wooden staircaseand a claw foot tub, yet all the conveniences to suit your needs. Five bedrooms with 2-1/2 bathrooms and a spacious walk-up attic. This corner lot features a great deal of privacywith a beautiful in ground pool. There is plenty of room

    Stacy Brescia-Spreer Curasi Realty, Inc.

    82 Wallkill Ave, Montgomery, NY 12549
  • /50

    $475,000

    • 4 Beds
    • 2.5 Baths
    • 2,288 Sq Ft

    11 Kevin Ct, Montgomery, NY 12549

    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

    Amanda Ferrantello Hudson Valley Griffith

    11 Kevin Ct, Montgomery, NY 12549
  • /49

    $474,900

    $85K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,096 Sq Ft

    68 Weaver St, Montgomery, NY 12549

    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

    Matthew Gibbs KW Hudson Valley Untied

    68 Weaver St, Montgomery, NY 12549
  • /36

    $449,900

    • 4 Beds
    • 2.5 Baths
    • 1,710 Sq Ft

    70 County Route 17, Pine Bush, NY 12566

    What a great buy! Hurry, don't wait. Enjoy the ease of one level living. Come see this beautifully remodeled, 1710 sf, 4 bedroom, 2.5 bath brick ranch with contemporary style & flair, on .97 lovely country acre in the Pine Bush School District. It features a superb new kitchen with stainless steel range, refrigerator, stove & microwave with stunning white marble look, ceramic tile floors and

    Marion Bruhns Howard Hanna Rand Realty

    70 County Route 17, Pine Bush, NY 12566
  • /34

    $599,999

    • 3 Beds
    • 2.5 Baths
    • 2,236 Sq Ft

    18 Locust Dr, Montgomery, NY 12549

    Privacy, space, and turn key comfort come together at this beautiful home in Montgomery, NY. Set back from the road on 2.5 partially wooded acres, this 3 bedroom (plus a large bonus room), 2.5 bathroom colonial offers the peaceful setting buyers want with the everyday convenience they need. Surrounded by trees for privacy, the property features flat, cleared land around the front, back, and sides

    JOHN SCARANO Keller Williams Realty

    18 Locust Dr, Montgomery, NY 12549
  • /5

    $165,000

    • Land
    • 2.5 Acres
    • $66,000 per Acre

    1460 State Route 52, Walden, NY 12586

    2.5 Acre commercial building lot with 378 ft frontage on Route 52 in Montgomery. Level, lightly wooded, zoned Tourist Commercial - zones are proposed for hospitality, short-term rentals, agribusiness, “fly-in” tourism, and other tourist and travel-related uses along with the type of uses generally permissible in Crossroad Commercial land use areas. Examples of appropriate uses include breweries,

    John Lease John J Lease REALTORS Inc

    1460 State Route 52, Walden, NY 12586
  • /50

    $2,895,000

    $100K PRICE DROP
    • 6 Beds
    • 9 Baths
    • 6,415 Sq Ft

    198 Corbett Rd, Montgomery, NY 12549

    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

    Nissim Levy Keller Williams Realty Liberty

    198 Corbett Rd, Montgomery, NY 12549
  • /41

    $580,000

    • 4 Beds
    • 2.5 Baths
    • 2,104 Sq Ft

    65 Judson Rd, Montgomery, NY 12549

    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

    Brittnai Pytlar RE/MAX Benchmark Realty Group

    65 Judson Rd, Montgomery, NY 12549
  • /50

    $699,900

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,681 Sq Ft

    24 Francis Harrison Ct, Montgomery, NY 12549

    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

    Nicholas Cuomo Keller Williams Realty

    24 Francis Harrison Ct, Montgomery, NY 12549
  • /34

    $525,000

    • 4 Beds
    • 2 Baths
    • 2,619 Sq Ft

    340 Dunn Rd, Montgomery, NY 12549

    Set on 1.4 picturesque acres, this beautifully updated farmhouse colonial offers the perfect blend of timeless character and modern comfort. From the moment you arrive, the home’s charm is undeniable—where classic design meets thoughtful updates throughout. Inside, you’ll find a warm and inviting layout designed for both everyday living and effortless entertaining. The heart of the home is the

    Christine Torres KW Hudson Valley Untied

    340 Dunn Rd, Montgomery, NY 12549
  • /50

    $834,400

    New Construction
    • 5 Beds
    • 3.5 Baths
    • 3,200 Sq Ft

    7 Morrow Ct, Walden, NY 12586

    New construction without the weight! This beautiful home with x Square feet of living space Has been completed and the seller can close quickly! This stunning Harrington II model by a respected local builder offers the perfect blend of luxury, space, and privacy on nearly 6 acres in the sought-after Post Road Estates community within the Valley Central School District. Step inside the impressive

    Sandra Spector Howard Hanna Rand Realty

    7 Morrow Ct, Walden, NY 12586
  • /33

    $799,000

    • 3 Beds
    • 2 Baths
    • 2,958 Sq Ft

    291 Comfort Trail, Montgomery, NY 12549

    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. COME AND SEE!

    Mark Tierney Howard Hanna Rand Realty

    291 Comfort Trail, Montgomery, NY 12549
  • /50

    $769,900

    • 3 Beds
    • 2.5 Baths
    • 3,400 Sq Ft

    42 Philip Dr, Montgomery, NY 12549

    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

    Johnette Berlingieri

    42 Philip Dr, Montgomery, NY 12549
  • /47

    $525,000

    • 4 Beds
    • 2.5 Baths
    • 1,800 Sq Ft

    7 Judson Rd, Montgomery, NY 12549

    Priced to sell! 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 nook that opens to

    Marion Bruhns Howard Hanna Rand Realty

    7 Judson Rd, Montgomery, NY 12549
  • /44

    $575,000

    • 4 Beds
    • 2.5 Baths
    • 3,038 Sq Ft

    20 County Highway 17, Thompson Ridge, NY 10985

    Centrally located within approximately 20 minutes of Resorts World Catskills, The Kartrite Resort & Indoor Waterpark, Minnewaska State Park, LEGOLAND New York, New Paltz, local wineries, shopping, MTA train access, Angry Orchard, and several sought-after Hudson Valley/Catskills golf destinations, this property offers the perfect blend of convenience, recreation, and lifestyle. Golf enthusiasts

    Michelle Gruberger Real Estate Circuit Inc

    20 County Highway 17, Thompson Ridge, NY 10985
  • /40

    $509,000

    • 3 Beds
    • 2 Baths
    • 1,796 Sq Ft

    479 River Rd, Montgomery, NY 12549

    Welcome to your own private retreat in the heart of Montgomery. Set on approximately 2 beautiful acres and surrounded by deeded agricultural preservation land, 479 River Rd offers something incredibly difficult to find today... long term protected privacy and peaceful country living without sacrificing convenience. This well cared for ranch style home offers the perfect opportunity for buyers

    Jason Madison eXp Realty

    479 River Rd, Montgomery, NY 12549
  • /40

    $1,190,000

    • 4 Beds
    • 2.5 Baths
    • 3,102 Sq Ft

    170 Dickerson Ave, Montgomery, NY 12549

    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

    Dylan Woods Howard Hanna Rand Realty

    170 Dickerson Ave, Montgomery, NY 12549
  • /40

    $699,000

    $11K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,646 Sq Ft

    83 Little Collabar Rd, Montgomery, NY 12549

    Fully renovated and thoughtfully upgraded, this stunning 4-bedroom, 2.5-bathroom, 2,646-square-foot Colonial in the Valley Central School District checks every box - and then a few you didn’t even know you wanted. A rare highlight is the two separate driveways - one leading to the home and attached garage, and the other to a heated 24x30 workshop with a car lift, making it a dream setup for car

    Wendy Beck Krumpfer Realty Group, LLC

    83 Little Collabar Rd, Montgomery, NY 12549
  • /18

    $499,000

    $26K PRICE DROP
    • Land
    • 12.2 Acres
    • $40,902 per Acre

    109 White Birch Ln, Montgomery, NY 12549

    Discover your own slice of the Hudson Valley at 109 White Birch Lane — a beautiful raw acreage parcel located on a private, dead-end road in the Town of Montgomery. This property offers a peaceful and secluded setting while still being just minutes from everything. Enjoy close proximity to the Villages of Montgomery and Walden, as well as easy access to I-84 and Stewart International Airport,

    Sean Drown Land and Water Realty LLC

    109 White Birch Ln, Montgomery, NY 12549
  • /38

    $409,000

    $20K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,448 Sq Ft

    46 Union St, Montgomery, NY 12549

    (***Previous deal fell through due to buyer financing***) Welcome to Holbrow House at 46 Union Street, a lovingly maintained and updated 1818 home in the quaint Village of Montgomery. As soon as you enter, you're greeted by the warmth of the historic wide plank wood floors and rooms filled with natural light. The main living area offers great flexibility with an additional room that can be used

    Andrea Mahoney Smitchger Realty

    46 Union St, Montgomery, NY 12549
  • /16

    $499,500

    $26K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,644 Sq Ft

    7 Didio Ln, Montgomery, NY 12549

    Perfect SHORT TERM RENTAL investment! AIRBNB ready. Fully furnished! Minutes to City Winery, Angry Orchard, and other attractions. Welcome to this beautifully updated home in the heart of Montgomery, New York, where comfort, style, and everyday convenience come together. Currently set up for SHORT TERM RENTAL investment, but perfect for buyers looking for a quiet neighborhood to settle into.

    James LaTempa Compass Greater NY, LLC

    7 Didio Ln, Montgomery, NY 12549
  • /50

    $515,000

    $10K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,260 Sq Ft

    5328 Searsville Rd, Pine Bush, NY 12566

    Welcome to this beautifully maintained 4 bedroom, 3 full bath home in the Pine Bush school district! Set on a picturesque 1 acre lot, and offering 2260 square feet of living space, this home combines classic charm with modern updates. Many updates and improvements have been completed within the last few years. Inside you will find hardwood floors, granite countertops, and a thoughtfully designed

    Gary MacEntee Keller Williams Realty

    5328 Searsville Rd, Pine Bush, NY 12566
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