Montgomery, NY Homes

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  $724,999

  $25K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,030 Sq Ft

  165 Benedict Rd, Montgomery, NY 12549

  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,

  

  Richard Baxter

  Keller Williams Realty

  165 Benedict Rd, Montgomery, NY 12549
• Explore Montgomery

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  /11

  $1,550 Per Month

  • 2 Beds
  • 1 Bath
  • 741 Sq Ft
  • Apartment for Rent

  205 Union St Unit 2, Montgomery, NY 12549

  Welcome to this charming second-floor rental opportunity perfectly situated on the main road through the historic Village of Montgomery! Nestled within the Valley Central School District, this inviting 2-bedroom, 1-bathroom apartment offers the ultimate in village living, putting local shopping boutiques, quaint coffee shops, and fantastic local restaurants just steps from your door. When you

  

  Richard Baxter

  Keller Williams Realty

  205 Union St Unit 2, Montgomery, NY 12549
• 

  $335,000

  Sold Jul 08, 2026

  24 Emperor Ln, Montgomery, NY 12549

  • 4 Beds
  • 2.5 Baths
  • 2,340 Sq Ft
  • Built 1978

  Last Sold Summary

  • 4% Below List Price
  • $143/SF
  • 34 Days On Market

  Current Estimated Value $390,259

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  24 Emperor Ln, Montgomery, NY 12549
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  Est $659,170

  Not Listed For Sale

  27 Whalen Dr, Montgomery, NY 12549

  • 4 Beds
  • 2.5 Baths
  • 2,462 Sq Ft
  • Built 2017

  27 Whalen Dr, Montgomery, NY 12549

  Last Sold Summary

  • 45 Days On Market

  Last Listing Agent Soleil Jackman Howard Hanna Rand Realty
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  $899,900

  • 4 Beds
  • 2.5 Baths
  • 2,871 Sq Ft

  64 W Corbett Rd, Montgomery, NY 12549

  Turn off the main road and the noise drops away. By the time the fields open up on both sides you have rolled the windows down without deciding to, and the last few minutes of the drive stop counting as a commute.Right now this is 3.35 acres and nothing else, which is the best part of it. Ground has not been broken. Nothing has been framed, poured, painted or decided. The approvals are

  

  Brian Caplicki

  KW Hudson Valley United

  64 W Corbett Rd, Montgomery, NY 12549
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  /15

  Starting at $1,750 Per Month

  • 1 Bed

  90 Hawkins Dr, Montgomery, NY 12549

  Nestled in the charming village of Montgomery, NY, Hawkins Apartments offers the perfect balance of comfort, convenience, and community.Whether grabbing coffee, dining out, or running errands, everything you need is just minutes from your doorstep. The property is also ideally positioned near major routes such as Route 208, Route 17K, and I-84, making commutes and travel throughout the

  Hawkins Apartments

  

  90 Hawkins Dr, Montgomery, NY 12549
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  $293,000

  Sold Dec 19, 2025

  58 Union St, Montgomery, NY 12549

  • 3 Beds
  • 1 Bath
  • 1,140 Sq Ft
  • Built 1900

  Last Sold Summary

  • 30% Below List Price
  • $257/SF
  • 71 Days On Market

  Current Estimated Value $309,731

  Last Listing Agent Lisa Wade-Sebring Hudson Valley Home Connection

  58 Union St, Montgomery, NY 12549
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  Not Listed For Sale

  34 Peale Place, Montgomery, NY 12549

  • 4 Beds
  • Built 2025

  34 Peale Place, Montgomery, NY 12549

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Richard Baxter Keller Williams Realty
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  $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

  

  Richard Baxter

  Keller Williams Realty

  294 Comfort Trail, Montgomery, NY 12549
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  $2,795 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,306 Sq Ft
  • House for Rent

  67 Union St, Montgomery, NY 12549

  Charming Victorian Home for Lease the Village of Montgomery.Welcome to 67 Union Street, a beautiful Victorian home filled with original character, timeless charm, and classic architectural details. Ideally situated in the heart of the Village, this special three-bedroom residence offers the opportunity to enjoy the warmth and character of a historic home while being just steps from everything

  Dawn Gregg Curasi Realty, Inc.

  67 Union St, Montgomery, NY 12549
• 

  $650,000

  Sold Aug 28, 2026

  30 Wavey Willow Ln, Montgomery, NY 12549

  • 4 Beds
  • 2.5 Baths
  • 2,168 Sq Ft
  • Built 1997

  Last Sold Summary

  • 4% Below List Price
  • $300/SF
  • 32 Days On Market

  Current Estimated Value $672,013

  Last Listing Agent Paul Biagini Biagini Realty

  30 Wavey Willow Ln, Montgomery, NY 12549
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  Not Listed For Sale

  58 Peale Place, Montgomery, NY 12549

  • 4 Beds
  • 2.5 Baths
  • 2,680 Sq Ft
  • Built 2025

  58 Peale Place, Montgomery, NY 12549

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Richard Baxter Keller Williams Realty
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  $649,900

  Pending

  • 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

  

  Matthew Morreale

  J. Morreale, LTD

  2056 State Route 17k, Montgomery, NY 12549
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  /14

  $1,825

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Condo for Rent

  3 Fedorko Ln Unit B, Montgomery, NY 12549

  2 bedrooms / 1 full bathroomTop-floor apartment in a two-unit buildingModern updated kitchenGleaming hardwood floorsBright, modern luxury vinyl flooringFreshly updated bathroomPlentiful closet spacePrivate mudroom entrance with coat closetIn-unit washer/dryer hookupsLarge private backyardStorage shedOff-street

  3 Fedorko Ln Unit B, Montgomery, NY 12549
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  $1,300,000

  Sold Jun 18, 2026

  0 Route 17k Unit KEY808699, Montgomery Town, NY 12575

  • Land
  • 6 Acres
  • $216,667 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 125 Days On Market

  Last Listing Agent George Koudounas RE/MAX Benchmark Realty Group

  0 Route 17k Unit KEY808699, Montgomery Town, NY 12575
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  Not Listed For Sale

  28 Peale Place, Montgomery, NY 12550

  • 4 Beds
  • 2.5 Baths
  • 3,085 Sq Ft
  • Built 2024

  28 Peale Place, Montgomery, NY 12550

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Richard Baxter Keller Williams Realty
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  $546,900

  $52K PRICE DROP Pending

  • 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 living space 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
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  $271,250

  Sold Jul 31, 2026

  506 Berea Rd, Montgomery, NY 12549

  • 2 Beds
  • 1 Bath
  • 1,137 Sq Ft
  • Built 1943

  Last Sold Summary

  • 18% Above List Price
  • $239/SF
  • 12 Days On Market

  Current Estimated Value $235,940

  Last Listing Agent Matthew Gibbs KW Hudson Valley United

  506 Berea Rd, Montgomery, NY 12549
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  Not Listed For Sale

  50 Harmony Ln, Montgomery, NY 12549

  • 2 Beds
  • 1 Bath
  • 540 Sq Ft
  • Built 1963

  50 Harmony Ln, Montgomery, NY 12549

  Last Sold Summary

  • 49 Days On Market

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group
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  $454,900

  • 3 Beds
  • 1 Bath
  • 1,824 Sq Ft

  49 Bailey Rd, Montgomery, NY 12549

  Welcome to this charming 3-bedroom, 1-bathroom Cape Cod style home nestled in the picturesque Town of Montgomery, offering the perfect blend of updated living and ultimate commuter convenience. Offering quick access to the Interstate 84 on-ramp from the nearby State Route 17K and Route 208 intersection, and situated just a short drive from local shopping plazas, neighborhood dining, banking,

  

  Richard Baxter

  Keller Williams Realty

  49 Bailey Rd, Montgomery, NY 12549
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  $257,500

  Sold Sep 08, 2026

  20 Barron Rd, Montgomery, NY 12549

  • 2 Beds
  • 1 Bath
  • 584 Sq Ft
  • Built 1940

  Last Sold Summary

  • 8% Below List Price
  • $441/SF
  • 127 Days On Market

  Current Estimated Value $264,883

  Last Listing Agent Kathy Dawson Howard Hanna Rand Realty

  20 Barron Rd, Montgomery, NY 12549
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  Est $624,050

  Not Listed For Sale

  128 Beaver Dam Rd, Montgomery, NY 12549

  • 3 Beds
  • 4 Baths
  • 2,324 Sq Ft
  • Built 2012

  128 Beaver Dam Rd, Montgomery, NY 12549

  Last Sold Summary

  • 63 Days On Market

  Last Listing Agent Richard Baxter Keller Williams Realty
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  /11

  $974,999

  New Construction Pending

  • 4 Beds
  • 2.5 Baths
  • 2,702 Sq Ft

  65 Peale Place, Montgomery, NY 12549

  Welcome to The Ponds at Montgomery—a beautifully designed 4-bedroom, 2.5-bath ranch-style home set in the desirable Town of Montgomery. Ideally located just minutes from upscale dining and local eateries, boutique shopping, corporate banking, premier golf courses, schools, parks, hiking trails, and professional fitness centers, this home also offers quick access to Interstate 84 and other major

  

  Richard Baxter

  Keller Williams Realty

  65 Peale Place, Montgomery, NY 12549
• 

  $360,000

  Sold Apr 10, 2026

  241 Freida St, Montgomery, NY 12549

  • 3 Beds
  • 1 Bath
  • 978 Sq Ft
  • Built 1957

  Last Sold Summary

  • 4% Below List Price
  • $368/SF
  • 74 Days On Market

  Current Estimated Value $361,950

  Last Listing Agent Lynelle Alessi KW Hudson Valley United

  241 Freida St, Montgomery, NY 12549
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  Not Listed For Sale

  985 Route 17k, Montgomery, NY 12449

  985 Route 17k, Montgomery, NY 12449

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Arnold Restivo Keller Williams Realty
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  $994,999

  New Construction Pending

  • 4 Beds
  • 3.5 Baths
  • 3,528 Sq Ft

  64 Peale Place, Montgomery, NY 12549

  Welcome to The Ponds at Montgomery—a beautifully designed 4-bedroom, 3.5-bath two-story home set on 2.30 private acres in the desirable Town of Montgomery. Ideally located just minutes from upscale dining, boutique shopping, and premier golf courses, this home also offers quick access to Interstate 84 and other major highways. Inside, the thoughtfully planned layout features a well-appointed

  

  Richard Baxter

  Keller Williams Realty

  64 Peale Place, Montgomery, NY 12549
• 

  $625,000

  Sold Feb 19, 2026

  135 Benedict Rd, Montgomery, NY 12549

  • 4 Beds
  • 3.5 Baths
  • 2,912 Sq Ft
  • Built 1991

  Last Sold Summary

  • $215/SF
  • 55 Days On Market

  Current Estimated Value $635,453

  Last Listing Agent Richard Baxter Keller Williams Realty

  135 Benedict Rd, Montgomery, NY 12549
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  Not Listed For Sale

  0 Bracken Rd Unit KEY822010, Montgomery, NY 12549

  0 Bracken Rd Unit KEY822010, Montgomery, NY 12549

  Last Sold Summary

  • 106 Days On Market

  Last Listing Agent Jay Feinberg KW Hudson Valley United
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  $1,100,000

  New Construction Open Tue 2PM - 4PM

  • 4 Beds
  • 2.5 Baths
  • 2,639 Sq Ft

  29 Peale Place, Montgomery, NY 12549

  A true masterpiece conceptualized by the renowned DeGraw and DeHaan Architects, this luxury 4-bedroom, 2.5-bathroom residence stands as a testament to over 40 years of elite design expertise. The home boasts a brilliant open floor plan, sophisticated finishes, and masterful architectural flourishes that create an inviting yet grand atmosphere. Offering over 2,600 square feet of impeccably

  

  Richard Baxter

  Keller Williams Realty

  29 Peale Place, Montgomery, NY 12549
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  $649,000

  Sold Oct 01, 2025

  73 Tweddle Farm Ln, Montgomery, NY 12549

  • 4 Beds
  • 2.5 Baths
  • 2,800 Sq Ft
  • Built 2010

  Last Sold Summary

  • $232/SF
  • 37 Days On Market

  Current Estimated Value $672,615

  Last Listing Agent Jordan Spordone HomeSmart Homes & Estates

  73 Tweddle Farm Ln, Montgomery, NY 12549
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  Est $575,813

  Not Listed For Sale

  394 Bailey Rd, Montgomery, NY 12549

  • 4 Beds
  • 3 Baths
  • 2,141 Sq Ft
  • Built 2017

  394 Bailey Rd, Montgomery, NY 12549

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Donna Brunell RE/MAX Benchmark Realty Group
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  $699,999

  New Construction $50K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 2,705 Sq Ft

  30 Northern Ave, Montgomery, NY 12586

  NEW CONSTRUCTION!!! Check out this 4 Bedroom, 2.5 Bathroom Colonial nestled in the Town of Montgomery and located in the Valley Central School District. This home is located a short drive to an array of local eateries/restaurants, shopping center, close to several local parks, a quarter mile from the Walden/Wallkill Walking Rail Trail, Wallkill River, and a short drive to most major highways

  

  Richard Baxter

  Keller Williams Realty

  30 Northern Ave, Montgomery, NY 12586
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  $360,000

  Sold Sep 14, 2026

  36 Charles St, Montgomery, NY 12549

  • 1 Bed
  • 1 Bath
  • 1,098 Sq Ft
  • Built 1956

  Last Sold Summary

  • 3% Above List Price
  • $328/SF
  • 29 Days On Market

  Current Estimated Value $352,293

  Last Listing Agent Richard Baxter Keller Williams Realty

  36 Charles St, Montgomery, NY 12549
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  Est $739,387

  Not Listed For Sale

  31 Lauren Ln, Montgomery, NY 12549

  • 3 Beds
  • 2.5 Baths
  • 2,627 Sq Ft
  • Built 2017

  31 Lauren Ln, Montgomery, NY 12549

  Last Sold Summary

  • 37 Days On Market

  Last Listing Agent Lorrainne Pisciotta Weichert Realtors
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  /49

  $699,000

  $40K PRICE DROP Pending

  • 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

  Antoinette Caruso Stonewall Realty Group LLC

  41 Philip Dr, Montgomery, NY 12549
• 

  $530,000

  Sold Apr 07, 2026

  1085 County Route 17, Montgomery, NY 12549

  • 4 Beds
  • 3 Baths
  • 3,144 Sq Ft
  • Built 1986

  Last Sold Summary

  • 1% Below List Price
  • $169/SF
  • 74 Days On Market

  Current Estimated Value $557,370

  Last Listing Agent Thomas Lawrenson Howard Hanna Rand Realty

  1085 County Route 17, Montgomery, NY 12549
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  Est $591,856

  Not Listed For Sale

  28 Eager Rd, Montgomery, NY 12549

  • 5 Beds
  • 2.5 Baths
  • 2,832 Sq Ft
  • Built 1786

  28 Eager Rd, Montgomery, NY 12549

  Last Sold Summary

  • 158 Days On Market

  Last Listing Agent Matthew Gibbs KW Hudson Valley United
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  /38

  $429,900

  $69K 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
• 

  $406,500

  Sold Sep 29, 2025

  303 Chandler Ln, Montgomery, NY 12549

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft
  • Built 1969

  Last Sold Summary

  • 2% Above List Price
  • $302/SF
  • 34 Days On Market

  Current Estimated Value $402,522

  Last Listing Agent Frank Gerbes RE/MAX Benchmark Realty Group

  303 Chandler Ln, Montgomery, NY 12549
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  Not Listed For Sale

  31 Francis Harrison Ct, Montgomery, NY 12549

  • 4 Beds
  • 2.5 Baths
  • 2,688 Sq Ft
  • Built 2023

  31 Francis Harrison Ct, Montgomery, NY 12549

  Last Sold Summary

  • 226 Days On Market

  Last Listing Agent George Koudounas RE/MAX Benchmark Realty Group

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