Montgomery, NY Homes

• 

  Est $706,133 Not Listed For Sale

  177 W Searsville Rd, Montgomery, NY 12549

  • 4 Beds
  • 2.5 Baths
  • 4,178 Sq Ft
  • Built 1998

  177 W Searsville Rd, Montgomery, NY 12549

  Last Sold Summary

  • 17% Above List Price
  • $145/SF
  • 194 Days On Market

  Last Sold Price $605,000

  Last Listing Agent Carol Cruz Keller Williams Hudson Valley
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• 

  

  

  /30

  $279,900

  • 2 Beds
  • 1 Bath
  • 584 Sq Ft

  20 Barron Rd, Montgomery, NY 12549

  This sweet cottage is great for 1st time home buyers, or people that just like to have low living expenses! You'll enjoy the large deck off the kitchen for enjoying BBQ's or the outside. You'll also enjoy the small neighborhood! At the end of Barron Rd, you can enjoy the Stewart State Forest, where there are more than 22 miles of major trails for hiking, biking, horseback riding, hunting, dog

  Kathy Dawson Howard Hanna Rand Realty

  20 Barron Rd, Montgomery, NY 12549
• 

  $875,000 Sold Jun 24, 2025

  24 Bridge St, Montgomery, NY 12549

  • 3 Beds
  • 2.5 Baths
  • 2,120 Sq Ft
  • Built 1885

  Last Sold Summary

  • 2% Below List Price
  • $413/SF
  • 19 Days On Market

  Current Estimated Value $848,625

  Last Listing Agent John Ruggieri BHHS Hudson Valley Properties

  24 Bridge St, Montgomery, NY 12549
• 

  Est $746,524 Not Listed For Sale

  47 Bookstaver Ln, Montgomery, NY 12549

  • 4 Beds
  • 2.5 Baths
  • 2,863 Sq Ft
  • Built 2000

  47 Bookstaver Ln, Montgomery, NY 12549

  Last Sold Summary

  • 4% Above List Price
  • $251/SF
  • 34 Days On Market

  Last Sold Price $720,000

  Last Listing Agent Marion Bruhns Howard Hanna Rand Realty
• 

  

  /2

  $559,000

  • Land
  • 7.6 Acres
  • $73,553 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 Keller Williams Hudson Valley

  0 New York 17k, Montgomery, NY 12549
• 

  $430,000 Sold May 13, 2025

  307 Bailey Rd, Montgomery, NY 12549

  • 2 Beds
  • 2.5 Baths
  • 2,172 Sq Ft
  • Built 1940

  Last Sold Summary

  • 16% Above List Price
  • $198/SF
  • 14 Days On Market

  Current Estimated Value $438,755

  Last Listing Agent Jennifer Loprieno Howard Hanna Rand Realty

  307 Bailey Rd, Montgomery, NY 12549
• 

  Est $747,543 Not Listed For Sale

  66 Bookstaver Ln, Montgomery, NY 12549

  • 4 Beds
  • 2.5 Baths
  • 3,101 Sq Ft
  • Built 1999

  66 Bookstaver Ln, Montgomery, NY 12549

  Last Sold Summary

  • 2% Above List Price
  • $235/SF
  • 55 Days On Market

  Last Sold Price $730,000

  Last Listing Agent Marc Windheuser RE/MAX Team
• 

  

  /45

  $479,900

  • 3 Beds
  • 1.5 Baths
  • 1,692 Sq Ft

  205 Oriole Dr, Montgomery, NY 12549

  Come join the wonderful world of Sweet Montgomery with village and country life at its best! This lovely home located in a desirable tree lined neighborhood has space for everyone to relax and enjoy the lifestyle of a charming town with quaint main street, wonderful shops, museum, restaurants, beautiful village park with fun for all ages (playground, pickleball, basketball & more!) and of course

  Rose Daversa Hudson Valley Home Connection

  205 Oriole Dr, Montgomery, NY 12549
• 

  $800,000 Sold Feb 20, 2026

  200 Hill Ave, Montgomery, NY 12549

  • 4 Beds
  • 3.5 Baths
  • 3,127 Sq Ft
  • Built 2025

  Last Sold Summary

  • $256/SF
  • 30 Days On Market

  Current Estimated Value $802,833

  Last Listing Agent Richard Baxter Keller Williams Realty

  200 Hill Ave, Montgomery, NY 12549
• 

  Est $485,558 Not Listed For Sale

  21 Ronaldson Rd, Montgomery, NY 12549

  • 3 Beds
  • 2.5 Baths
  • 1,792 Sq Ft
  • Built 1985

  21 Ronaldson Rd, Montgomery, NY 12549

  Last Sold Summary

  • 17% Above List Price
  • $232/SF
  • 47 Days On Market

  Last Sold Price $415,000

  Last Listing Agent Amanda Ferrantello Hudson Valley Griffith
• 

  

  /33

  $725,000

  • 6 Beds
  • 4 Baths
  • 2,656 Sq Ft

  2040 State Route 17k, Montgomery, NY 12549

  Discover an exceptional investment or owner-occupied opportunity at this well-maintained legal two-family duplex, set on 2.7 acres in the Town of Montgomery. Built in 2002, this property offers modern construction, strong mechanicals, and a layout that supports long-term stability and income.Each unit features a bright and functional floor plan with comfortable living space, well-appointed

  Michelle Gruberger Real Estate Circuit Inc

  2040 State Route 17k, Montgomery, NY 12549
• 

  $554,000 Sold Mar 20, 2026

  317 Angelo Dr, Montgomery, NY 12549

  • 5 Beds
  • 2.5 Baths
  • 2,722 Sq Ft
  • Built 1998

  Last Sold Summary

  • 4% Below List Price
  • $204/SF
  • 73 Days On Market

  Current Estimated Value $561,204

  Last Listing Agent Richard Baxter Keller Williams Realty

  317 Angelo Dr, Montgomery, NY 12549
• 

  Est $551,454 Not Listed For Sale

  3 Chandler Cir, Montgomery, NY 12549

  • 4 Beds
  • 2.5 Baths
  • 1,944 Sq Ft
  • Built 1975

  3 Chandler Cir, Montgomery, NY 12549

  Last Sold Summary

  • $283/SF
  • 20 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Susan Mohart Rita Levine Real Estate
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  /41

  $365,000

  • 6 Beds
  • 2 Baths
  • 2,955 Sq Ft

  265 Goodwill Rd, Montgomery, NY 12549

  This spacious 6-bedroom home is full of potential and ready for your vision. Set in a highly desirable area, it offers a rare opportunity to create your dream home in a prime location. With five bedrooms upstairs and a large main-level bedroom, this layout is ideal for multi-generational living or flexible space needs. The home features an oversized living room, two full bathrooms, a dedicated

  Denise Clancy Curasi Realty, Inc.

  265 Goodwill Rd, Montgomery, NY 12549
• 

  $565,000 Sold Mar 26, 2025

  164 Pleasant Ave, Montgomery, NY 12549

  • 4 Beds
  • 2.5 Baths
  • 2,528 Sq Ft
  • Built 1966

  Last Sold Summary

  • 6% Below List Price
  • $223/SF
  • 179 Days On Market

  Current Estimated Value $595,322

  Last Listing Agent Ian Pinckney Curasi Realty, Inc.

  164 Pleasant Ave, Montgomery, NY 12549
• 

  Est $485,122 Not Listed For Sale

  8 Powers Ln, Montgomery, NY 12549

  • 4 Beds
  • 2 Baths
  • 2,314 Sq Ft
  • Built 1973

  8 Powers Ln, Montgomery, NY 12549

  Last Sold Summary

  • 7% Above List Price
  • $197/SF
  • 42 Days On Market

  Last Sold Price $455,000

  Last Listing Agent Stacy Brescia-Spreer Curasi Realty, Inc.
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  /27

  $449,900 Pending

  • 3 Beds
  • 2 Baths
  • 2,313 Sq Ft

  264 Wilson St, Montgomery, NY 12549

  Price Improved! Spacious and inviting, this raised ranch home offers over 2,300 square feet of living space in the highly sought-after Village of Montgomery. Featuring 3 bedrooms and 2 full baths, the home blends comfort and character with a cathedral and beamed ceiling that enhances the light-filled eat-in kitchen. Just off the kitchen, a versatile den or office space provides a perfect

  Patricia Sassi RE/MAX Benchmark Realty Group

  264 Wilson St, Montgomery, NY 12549
• 

  $998,373 Sold Jan 27, 2026

  77 Peale Place, Montgomery, NY 12549

  • 3 Beds
  • 2.5 Baths
  • 2,795 Sq Ft
  • Built 2026

  Last Sold Summary

  • 11% Above List Price
  • $357/SF
  • 8 Days On Market

  Last Listing Agent Richard Baxter Keller Williams Realty

  77 Peale Place, Montgomery, NY 12549
• 

  Est $472,232 Not Listed For Sale

  10 Powers Ln, Montgomery, NY 12549

  • 3 Beds
  • 2 Baths
  • 2,546 Sq Ft
  • Built 1971

  10 Powers Ln, Montgomery, NY 12549

  Last Sold Summary

  • 6% Above List Price
  • $175/SF
  • 22 Days On Market

  Last Sold Price $445,000

  Last Listing Agent Chativa Bowen Keller Williams Realty
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  /15

  $295,000

  • 2 Beds
  • 1.5 Baths
  • 1,362 Sq Ft

  27 Wintergreen Ct, Montgomery, NY 12549

  Welcome to 27 Wintergreen Ct, a well-maintained townhouse located in an established residential community in Montgomery, NY. This home offers a functional layout with comfortable living spaces, ideal for everyday living and entertaining. The main level features a bright living area that flows into the kitchen and dining space, while the upper level provides generously sized bedrooms and ample

  Nicholas Torsiello K. Fortuna Realty, Inc.

  27 Wintergreen Ct, Montgomery, NY 12549
• 

  $547,000 Sold Sep 19, 2025

  12 Sycamore Dr, Montgomery, NY 12549

  • 3 Beds
  • 2.5 Baths
  • 1,840 Sq Ft
  • Built 1997

  Last Sold Summary

  • 4% Above List Price
  • $297/SF
  • 36 Days On Market

  Current Estimated Value $538,345

  Last Listing Agent Richard Baxter Keller Williams Realty

  12 Sycamore Dr, Montgomery, NY 12549
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  Est $598,783 Not Listed For Sale

  18 Kool Ln, Montgomery, NY 12549

  • 5 Beds
  • 4 Baths
  • 2,642 Sq Ft
  • Built 1973

  18 Kool Ln, Montgomery, NY 12549

  Last Sold Summary

  • 3% Above List Price
  • $220/SF
  • 25 Days On Market

  Last Sold Price $580,000

  Last Listing Agent Larry Curasi Curasi Realty, Inc.
• 

  

  /50

  $2,995,000

  • 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
• 

  $885,820 Sold Sep 18, 2025

  58 Peale Place, Montgomery, NY 12549

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

  Last Sold Summary

  • 4% Above List Price
  • $331/SF
  • 3 Days On Market

  Last Listing Agent Richard Baxter Keller Williams Realty

  58 Peale Place, Montgomery, NY 12549
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  Est $571,944 Not Listed For Sale

  708 W Kaisertown Rd, Montgomery, NY 12549

  • 3 Beds
  • 3 Baths
  • 3,041 Sq Ft
  • Built 1986

  708 W Kaisertown Rd, Montgomery, NY 12549

  Last Sold Summary

  • 9% Above List Price
  • $173/SF
  • 221 Days On Market

  Last Sold Price $525,000

  Last Listing Agent Asha Keegan Howard Hanna Rand Realty
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  /11

  $974,999

  • 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
• 

  $460,000 Sold Dec 22, 2025

  114 Union St, Montgomery, NY 12549

  • 3 Beds
  • 1.5 Baths
  • 1,176 Sq Ft
  • Built 1924

  Last Sold Summary

  • 8% Above List Price
  • $391/SF
  • 6 Days On Market

  Current Estimated Value $459,712

  Last Listing Agent Larry Curasi Curasi Realty, Inc.

  114 Union St, Montgomery, NY 12549
• 

  Est $496,348 Not Listed For Sale

  739 W Kaisertown Rd, Montgomery, NY 12549

  • 3 Beds
  • 2.5 Baths
  • 2,167 Sq Ft
  • Built 1971

  739 W Kaisertown Rd, Montgomery, NY 12549

  Last Sold Summary

  • 13% Above List Price
  • $203/SF
  • 30 Days On Market

  Last Sold Price $440,000

  Last Listing Agent Jackie Siracuse Absolute Real Estate of NY Inc
• 

  

  /14

  $370,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 2,300 Sq Ft

  6 Tyler St, Montgomery, NY 12549

  New Roof, New Siding. Just needs cosmetic work on the inside. Great for someone looking to purchase at a discounted price and add some value from day one.

  Derek Greene Greene Realty Group

  6 Tyler St, Montgomery, NY 12549
• 

  $660,000 Sold Dec 19, 2025

  560 Winding Hill Rd, Montgomery, NY 12549

  • 4 Beds
  • 2.5 Baths
  • 2,644 Sq Ft
  • Built 2002

  Last Sold Summary

  • 2% Above List Price
  • $250/SF
  • 18 Days On Market

  Current Estimated Value $661,608

  Last Listing Agent Philip Szumlaski Keller Williams Realty

  560 Winding Hill Rd, Montgomery, NY 12549
• 

  Est $288,078 Not Listed For Sale

  60 Harmony Ln, Montgomery, NY 12549

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1958

  60 Harmony Ln, Montgomery, NY 12549

  Last Sold Summary

  • 15% Above List Price
  • $260/SF
  • 26 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Frank Muccari Cronin & Company Real Estate
• 

  

  /6

  $994,999

  • 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
• 

  $350,000 Sold Sep 22, 2025

  34 Peale Place, Montgomery, NY 12549

  • Land
  • 1.32 Acres
  • $265,152 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 3 Days On Market

  Last Listing Agent Richard Baxter Keller Williams Realty

  34 Peale Place, Montgomery, NY 12549
• 

  Est $417,341 Not Listed For Sale

  66 Ridge Rd, Montgomery, NY 12549

  • 2 Beds
  • 2 Baths
  • 1,952 Sq Ft
  • Built 1972

  66 Ridge Rd, Montgomery, NY 12549

  Last Sold Summary

  • 4% Above List Price
  • $205/SF
  • 51 Days On Market

  Last Sold Price $400,000

  Last Listing Agent Danielle Riggs Keller Williams Hudson Valley
• 

  

  /15

  $349,999

  • 2 Beds
  • 1.5 Baths
  • 1,353 Sq Ft

  20 Wintergreen Ct, Montgomery, NY 12549

  Don’t miss out on this rare find—a sought-after end unit tucked away in the quiet Spring Meadow community right in the heart of the Village of Montgomery. This home features a bright and comfortable living room that feels open and airy, leading right into a functional galley kitchen perfect for whipping up your favorite meals. The layout flows naturally into a cozy dining area, making the whole

  Peter Stika Curasi Realty, Inc.

  20 Wintergreen Ct, Montgomery, NY 12549
• 

  $450,000 Sold Oct 21, 2025

  24 Taft Ave, Montgomery, NY 12549

  • 3 Beds
  • 1.5 Baths
  • 1,569 Sq Ft
  • Built 1948

  Last Sold Summary

  • 3% Above List Price
  • $287/SF
  • 16 Days On Market

  Current Estimated Value $440,209

  Last Listing Agent Maureen Cronin Cronin & Company Real Estate

  24 Taft Ave, Montgomery, NY 12549
• 

  Est $319,105 Not Listed For Sale

  38 Harmony Ln, Montgomery, NY 12549

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1965

  38 Harmony Ln, Montgomery, NY 12549

  Last Sold Summary

  • 5% Above List Price
  • $305/SF
  • 38 Days On Market

  Last Sold Price $305,000

  Last Listing Agent Susan Mohart Rita Levine Real Estate
• 

  

  /13

  $59,999

  • Land
  • 0.69 Acre
  • $87,119 per Acre

  0 High Meadows Rd, Montgomery, NY 12586

  VACANT LOT!!! BUILD YOUR DREAM HOME!!! Check out this Walden lot nestled in the Town of Montgomery and in the Valley Central School District. This .69 acre parcel is close to a variety of amenities, including local shopping, restaurants, schools, close to all five village parks, Walden Wallkill Rail Trail, Wallkill River, a short 15 minutes drive to the all new Resorts World Hudson Valley Casino

  Heather Geissler Keller Williams Realty

  0 High Meadows Rd, Montgomery, NY 12586
• 

  $150,050 Sold Jul 24, 2025

  50 Harmony Ln, Montgomery, NY 12549

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

  Last Sold Summary

  • 8% Above List Price
  • $278/SF
  • 49 Days On Market

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  50 Harmony Ln, Montgomery, NY 12549
• 

  Est $648,767 Not Listed For Sale

  258 Goodwill Rd, Montgomery, NY 12549

  • 4 Beds
  • 2.5 Baths
  • 2,964 Sq Ft
  • Built 1997

  258 Goodwill Rd, Montgomery, NY 12549

  Last Sold Summary

  • 10% Above List Price
  • $200/SF
  • 29 Days On Market

  Last Sold Price $592,000

  Last Listing Agent Frank Muccari Cronin & Company Real Estate

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