Montgomery, NY Homes

• 

  Est $732,968 Not Listed For Sale

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

  177 W Searsville Rd, Montgomery, NY 12549

  177 W Searsville Rd, Montgomery, NY 12549
• 

  

  

  /50

  $1,599,000 Pending

  • 6 Beds
  • 9 Baths
  • 6,415 Sq Ft

  198 Corbett Rd, Montgomery, NY 12549

  An Elevated Yellowstone-Inspired Retreat in Montgomery, NY Nestled on 48.5 expansive acres, this remarkable residence rises as if penned from a modern western saga. It is not merely a house; it is a sanctuary that blends the inviting, Yellowstone-inspired charm with the refined comforts of contemporary luxury. Spanning 6,415 square feet and offering six bedrooms each with its own bathroom, the

  Carmela Lopez Borrazas Keller Williams Realty

  198 Corbett Rd, 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

  Last Listing Agent Frank Gerbes RE/MAX Benchmark Realty Group

  303 Chandler Ln, Montgomery, NY 12549
• 

  Est $709,921 Not Listed For Sale

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

  47 Bookstaver Ln, Montgomery, NY 12549

  47 Bookstaver Ln, Montgomery, NY 12549
• 

  

  

  /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
• 

  $736,000 Sold May 29, 2025

  20 Daisy Ln, Montgomery, NY 12549

  • 3 Beds
  • 3.5 Baths
  • 3,199 Sq Ft
  • Built 2001

  Last Sold Summary

  • 5% Above List Price
  • $230/SF
  • 21 Days On Market

  Current Estimated Value $755,240

  Last Listing Agent Steve Moreau Tactical Realty LLC

  20 Daisy Ln, Montgomery, NY 12549
• 

  Est $749,599 Not Listed For Sale

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

  66 Bookstaver Ln, Montgomery, NY 12549

  66 Bookstaver Ln, Montgomery, NY 12549
• 

  

  /50

  $799,999

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

  200 Hill Ave, Montgomery, NY 12549

  NEW CONSTRUCTION!!! VALLEY CENTRAL SCHOOLS!!! Check out this 4 Bedroom, 3.5 bathroom stunning Ranch style home nestled in the Town of Montgomery and in the highly sought after Valley Central School District. This home offers a prime location with easy access to the picturesque Hamlet of Pine Bush, delightful Village of Walden and the vibrant Village of Montgomery. Each of these nearby locales is

  Richard Baxter Keller Williams Realty

  200 Hill Ave, Montgomery, NY 12549
• 

  $455,000 Sold Jul 07, 2025

  331 Lake Vue Dr, Montgomery, NY 12549

  • 5 Beds
  • 2 Baths
  • 1,872 Sq Ft
  • Built 1957

  Last Sold Summary

  • 5% Above List Price
  • $243/SF
  • 26 Days On Market

  Current Estimated Value $462,939

  Last Listing Agent Anne Marie O'Brien Curasi Realty, Inc.

  331 Lake Vue Dr, Montgomery, NY 12549
• 

  Est $391,847 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,720 Sq Ft

  724 State Route 211, Montgomery, NY 12549

  724 State Route 211, Montgomery, NY 12549
• 

  

  /42

  $574,999 Open Sun 1PM - 3PM

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

  317 Angelo Dr, Montgomery, NY 12549

  VALLEY CENTRAL SCHOOL DISTRICT!! Welcome to this beautifully maintained and spacious home, perfectly set in a quiet residential neighborhood and offering an ideal blend of comfort, functionality, and natural light. Step inside to find an inviting layout that begins with a bright and open living room featuring hardwood floors, large windows, and plenty of space for relaxing or gathering with loved

  Richard Baxter Keller Williams Realty

  317 Angelo Dr, 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 $887,500

  Last Listing Agent John Ruggieri BHHS Hudson Valley Properties

  24 Bridge St, Montgomery, NY 12549
• 

  Est $298,440 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,068 Sq Ft

  2029 State Route 208, Montgomery, NY 12549

  2029 State Route 208, Montgomery, NY 12549
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  /46

  $749,999 Open Sun 12PM - 2PM

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

  28 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

  28 Northern Ave, Montgomery, NY 12586
• 

  $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 $477,218

  Last Listing Agent Jennifer Loprieno Howard Hanna Rand Realty

  307 Bailey Rd, Montgomery, NY 12549
• 

  Est $508,898 Not Listed For Sale

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

  21 Ronaldson Rd, Montgomery, NY 12549

  21 Ronaldson Rd, Montgomery, NY 12549
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  /47

  $479,000 Pending

  • 4 Beds
  • 1.5 Baths
  • 1,844 Sq Ft

  200 Cardinal Dr, Montgomery, NY 12549

  Discover this inviting corner-lot home in the highly sought-after Montgomery Village neighborhood. The main level features three bedrooms and an open-concept living area with an island kitchen and dining room, all with hardwood floors. The heated, enclosed sunporch provides additional year-round living space.The lower level is a true bonus, offering a fourth bedroom, a large family room,

  Maureen Cronin Cronin & Company Real Estate

  200 Cardinal Dr, Montgomery, NY 12549
• 

  $740,000 Sold Feb 10, 2025

  96 Meadowood Rd, Montgomery, NY 12549

  • 3 Beds
  • 2.5 Baths
  • 3,212 Sq Ft
  • Built 1997

  Last Sold Summary

  • 5% Below List Price
  • $230/SF
  • 62 Days On Market

  Current Estimated Value $769,062

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  96 Meadowood Rd, Montgomery, NY 12549
• 

  Est $504,080 Not Listed For Sale

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

  8 Powers Ln, Montgomery, NY 12549

  8 Powers Ln, Montgomery, NY 12549
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  /41

  $375,000

  • 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
• 

  $380,000 Sold Jan 07, 2025

  248 Tompkins Rd, Montgomery, NY 12549

  • 3 Beds
  • 2.5 Baths
  • 2,180 Sq Ft
  • Built 1992

  Last Sold Summary

  • 12% Above List Price
  • $174/SF
  • 15 Days On Market

  Current Estimated Value $444,654

  Last Listing Agent Corey Gardner K. Fortuna Realty, Inc.

  248 Tompkins Rd, Montgomery, NY 12549
• 

  Est $559,822 Not Listed For Sale

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

  708 W Kaisertown Rd, Montgomery, NY 12549

  708 W Kaisertown Rd, Montgomery, NY 12549
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  /31

  $449,900

  • 2 Beds
  • 1.5 Baths
  • 1,513 Sq Ft

  1597 State Route 17k, Montgomery, NY 12549

  Welcome home to this beautifully updated 2-bedroom, 1.5-bath charmer—rebuilt in 2008 and perfectly situated just outside the Village of Montgomery. From the moment you arrive, you’ll appreciate the inviting covered front porch, back deck, stone walkways, and beautifully landscaped front and backyard, complete with a convenient storage shed. Inside, warm hardwood floors flow throughout, leading

  Chris Ogden Realty Promotions Inc

  1597 State Route 17k, 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 $608,460

  Last Listing Agent Ian Pinckney Curasi Realty, Inc.

  164 Pleasant Ave, Montgomery, NY 12549
• 

  Est $518,501 Not Listed For Sale

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

  739 W Kaisertown Rd, Montgomery, NY 12549

  739 W Kaisertown Rd, Montgomery, NY 12549
• 

  

  /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
• 

  $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 $555,989

  Last Listing Agent Richard Baxter Keller Williams Realty

  12 Sycamore Dr, Montgomery, NY 12549
• 

  Est $291,561 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  60 Harmony Ln, Montgomery, NY 12549

  60 Harmony Ln, Montgomery, NY 12549
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  /15

  $310,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,437 Sq Ft

  34 Summer Set Dr, Montgomery, NY 12549

  Three Bedroom ~ Three Bath Condo in Desirable Spring Meadows, Montgomery N. Y. Great Schools , Village Parks, Senior Building with many activities & Events + Pickle Ball Courts. Walk to Shops, Great Restaurants and Village Events & Historic Buildings & Montessori School. You ll Enjoy the 3 Season Porch with adjoining Storage closet. Garden Area with tall FENCE for PRIVACY. Spacious Master bedroom

  Margaret Williams CENTURY 21 ED & MARGARET WILLIAMS REALTY

  34 Summer Set Dr, 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
• 

  Est $429,549 Not Listed For Sale

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

  66 Ridge Rd, Montgomery, NY 12549

  66 Ridge Rd, Montgomery, NY 12549
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  /32

  $724,000

  • 4 Beds
  • 2.5 Baths
  • 3,126 Sq Ft

  822 W Kaisertown Rd, Montgomery, NY 12549

  Come view this excellent quality built private well maintained home set on 2.2 acres. Perfect for the holiday get togethers to accommodate family and friends in this large kitchen with a 7 foot center island. The dining room, living room and den with wood fireplace for those cozy nights. Parking will accommodate 15 plus cars. You won't be without heat and most lighting with the Generac Generator.

  Kimberly Behrens Howard Hanna Rand Realty

  822 W Kaisertown Rd, 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

  Last Listing Agent Larry Curasi Curasi Realty, Inc.

  114 Union St, Montgomery, NY 12549
• 

  Est $328,325 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  38 Harmony Ln, Montgomery, NY 12549

  38 Harmony Ln, Montgomery, NY 12549
• 

  

  /12

  $124,999

  • Land
  • 2.76 Acres
  • $45,289 per Acre

  TBD Saint Michaels Ln, Montgomery, NY 12586

  Nestled in a quiet and wooded setting, this raw, vacant parcel offers approximately 2.76 acres of prime rural-residential land. Surrounded by mature trees and natural beauty, the property provides privacy while still being conveniently located near local amenities and main roads. Featuring easy access via a 20’ wide lane and bordered by the NYC aqueduct line, it’s an ideal opportunity for

  Dulce Contreras Keller Williams Realty

  TBD Saint Michaels Ln, Montgomery, NY 12586
• 

  $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

  Last Listing Agent Philip Szumlaski Keller Williams Realty

  560 Winding Hill Rd, Montgomery, NY 12549
• 

  Est $634,370 Not Listed For Sale

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

  258 Goodwill Rd, Montgomery, NY 12549

  258 Goodwill Rd, Montgomery, NY 12549
• 

  

  /23

  $299,000 Pending

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft

  38 Jones Ln, Montgomery, NY 12549

  Charming Cottage Retreat in Montgomery — Goshen School District Tucked at the very end of a quiet dead-end road, 38 Jones Lane offers the rare combination of peaceful seclusion and convenient access to nearby amenities. Located in the sought-after Goshen School District, this 2-bedroom, 1-bath ranch-style cottage offers simplicity, efficiency, and charm on a low-maintenance .16-acre lot. Step

  Alyse Toffel Keller Williams Hudson Valley

  38 Jones Ln, 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
• 

  /2

  Est $486,731 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,637 Sq Ft

  2077 State Route 208, Montgomery, NY 12549

  2077 State Route 208, Montgomery, NY 12549

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