Montgomery, NY Homes

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  /34

  $899,900

  $50K PRICE DROP Pending

  • 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

  

  Chris Ogden

  Realty Promotions Inc

  41 Fern Wood Way, Montgomery, NY 12549
• Explore Montgomery

• 

  

  

  /15

  $1,600 Per Month

  • 1 Bed
  • 1 Bath
  • 780 Sq Ft
  • Apartment for Rent

  174 Clinton St, Montgomery, NY 12549

  VILLAGE LIVING!!! FIRST FLOOR UNIT!!! Check out this 1 Bedroom, 1 Bathroom first floor apartment nestled in the Village of Montgomery and in the VC School District. This apartment is surrounded by Village amenities including local eateries/restaurants, local shopping, banking centers, Village parks, local entertainment venues, and within 10 minutes drive to most major highways including

  

  Richard Baxter

  Keller Williams Realty

  174 Clinton St, Montgomery, NY 12549
• 

  

  

  /45

  $677,500

  Sold Aug 27, 2025

  95 Heritage Ln, Montgomery, NY 12549

  • 3 Beds
  • 3.5 Baths
  • 3,966 Sq Ft
  • Built 1994

  Last Sold Summary

  • 7% Below List Price
  • $171/SF
  • 44 Days On Market

  Current Estimated Value $692,442

  Last Listing Agent Linda Majetich Hansen BHHS HUDSON VALLEY PROP-NP

  95 Heritage Ln, Montgomery, NY 12549
• 

  Est $692,992

  Not Listed For Sale

  382 Bailey Rd, Montgomery, NY 12549

  • 4 Beds
  • 3 Baths
  • 2,549 Sq Ft
  • Built 2018

  382 Bailey Rd, Montgomery, NY 12549

  Last Sold Summary

  • 33 Days On Market
• 

  

  

  /42

  $465,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,693 Sq Ft

  243 Union St, Montgomery, NY 12549

  Charming Corner Ranch in the Heart of Montgomery Village Welcome to this beautifully updated and maintained corner ranch in the desirable Village of Montgomery! This move-in ready home features 3 spacious bedrooms and 2 fully updated bathrooms. The modern kitchen is a chef’s delight, complete with sleek granite countertops, stainless steel appliances, and fresh paint throughout. Step outside to

  

  Joy Gallagher

  Weichert Realtors

  243 Union St, Montgomery, NY 12549
• 

  

  /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
• 

  $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 $301,842

  Last Listing Agent Lisa Wade-Sebring Hudson Valley Home Connection

  58 Union St, Montgomery, NY 12549
• 

  Not Listed For Sale

  985 Route 17k, Montgomery, NY 12449

  985 Route 17k, Montgomery, NY 12449

  Last Sold Summary

  • 0 Days On Market
• 

  

  /33

  $399,999

  • 3 Beds
  • 1 Bath
  • 1,184 Sq Ft

  393 Goodwill Rd, Montgomery, NY 12549

  Enjoy the perfect balance of country living and everyday convenience in this inviting 3 bedroom, 1 bath ranch set on a spacious 1 acre lot. The ease of single level living, the home features a functional layout, updated kitchen and an island, comfortable living room set up for a pellet stove, and abundant natural light throughout. The property provides plenty of room to enjoy the outdoors,

  

  Jennifer Loprieno

  Howard Hanna Rand Realty

  393 Goodwill Rd, Montgomery, NY 12549
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  /7

  $1,900 Per Month

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

  148 Clinton St Unit 4, Montgomery, NY 12549

  2 Bedroom Apartment for Rent – Montgomery | Valley Central Schools Well-kept 2 bedroom, 1 bathroom apartment located in Montgomery in the Valley Central School District. This unit features updated flooring throughout, a simple kitchen with full-size appliances, and a bright living space with natural light. The bedroom offers a comfortable layout and the unit includes a full bathroom and

  

  Richard Baxter

  Keller Williams Realty

  148 Clinton St Unit 4, Montgomery, NY 12549
• 

  $610,000

  Sold Sep 08, 2025

  38 Wavey Willow Ln, Montgomery, NY 12549

  • 4 Beds
  • 2.5 Baths
  • 2,648 Sq Ft
  • Built 1998

  Last Sold Summary

  • 1% Above List Price
  • $230/SF
  • 10 Days On Market

  Current Estimated Value $646,863

  Last Listing Agent Annette Bauer Century 21 E & M Williams Rlty

  38 Wavey Willow Ln, Montgomery, NY 12549
• 

  Est $586,013

  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
• 

  

  /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

  

  Richard Baxter

  Keller Williams Realty

  294 Comfort Trail, Montgomery, NY 12549
• 

  /2

  Call for Price

  • 1 Bed

  1006 Mill Place, Montgomery, NY 12549

  Paltz River Apartments

  1006 Mill Place, Montgomery, NY 12549
• 

  $665,000

  Sold Jul 18, 2025

  4 Barley Hill Rd, Montgomery, NY 12549

  • 4 Beds
  • 2.5 Baths
  • 2,790 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $238/SF
  • 33 Days On Market

  Current Estimated Value $697,970

  Last Listing Agent Anita S. Cristiano HomeSmart Homes & Estates

  4 Barley Hill Rd, Montgomery, NY 12549
• 

  Est $770,496

  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
• 

  

  /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

  2056 State Route 17k, Montgomery, NY 12549
• 

  /2

  $1,900 Per Month

  • 2 Beds
  • 1.5 Baths
  • 850 Sq Ft
  • Apartment for Rent

  546 County Route 17 Unit B, Montgomery, NY 12549

  COMING SOON TO THE MARKET

  

  Richard Baxter

  Keller Williams Realty

  546 County Route 17 Unit B, Montgomery, NY 12549
• 

  $450,000

  Sold Aug 18, 2025

  201 Tompkins Rd, Montgomery, NY 12549

  • 4 Beds
  • 2.5 Baths
  • 1,670 Sq Ft
  • Built 1987

  Last Sold Summary

  • 3% Below List Price
  • $269/SF
  • 68 Days On Market

  Current Estimated Value $451,921

  Last Listing Agent Tremaine Selby Weichert Realtors

  201 Tompkins Rd, Montgomery, NY 12549
• 

  Est $591,546

  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
• 

  

  /20

  $349,999

  Coming Soon

  • 1 Bed
  • 1 Bath
  • 1,098 Sq Ft

  36 Charles St, Montgomery, NY 12549

  Coming Soon to the market!!!

  

  Richard Baxter

  Keller Williams Realty

  36 Charles St, Montgomery, NY 12549
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  /8

  Starting at $486 Per Month

  • 1 Bed

  4-6 Brescia Way, Montgomery, NY 12549

  Our Montgomery apartments offer a comfortable yet stylish lifestyle right in the heart of the community. With a wide range of amenities and an efficient room plan, each airy one-bedroom apartment provides the perfect solution for comfortable senior living.Close proximity to the charming village of Montgomery makes for a life of convenience and serenity for Montgomery Manor residents,

  Montgomery Manor

  

  4-6 Brescia Way, Montgomery, NY 12549
• 

  $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
• 

  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
• 

  

  /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
• 

  

  /5

  $1,350 Per Month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Apartment for Rent

  49 Walnut St Unit 3, Montgomery, NY 12549

  Located on a quiet street near the intersection on Route 17K and Route 208, this charming one-bedroom apartment offers the perfect combination of comfort and convenience. Just minutes from I-84, Stewart International Airport, Amazon Warehouse, major commuter routes, and the beautiful village of Montgomery. You will enjoy easy access to work, shopping, dining, and recreation. Features

  Roxanne Hartman Timothy W. Kramer

  49 Walnut St Unit 3, 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 $361,121

  Last Listing Agent Lynelle Alessi KW Hudson Valley United

  241 Freida St, Montgomery, NY 12549
• 

  Est $617,230

  Not Listed For Sale

  644 Bullville Rd, Montgomery, NY 12549

  • 4 Beds
  • 3 Baths
  • 2,460 Sq Ft
  • Built 2019

  644 Bullville Rd, Montgomery, NY 12549

  Last Sold Summary

  • 18 Days On Market
• 

  

  /6

  $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
• 

  $485,000

  Sold Aug 27, 2025

  269 Wilson St, Montgomery, NY 12549

  • 3 Beds
  • 2.5 Baths
  • 1,870 Sq Ft
  • Built 1973

  Last Sold Summary

  • 3% Below List Price
  • $259/SF
  • 29 Days On Market

  Current Estimated Value $476,073

  Last Listing Agent Frank Muccari Cronin & Company Real Estate

  269 Wilson St, Montgomery, NY 12549
• 

  Est $682,929

  Not Listed For Sale

  19 Grosso Ct, Montgomery, NY 12549

  • 6 Beds
  • 5 Baths
  • 3,200 Sq Ft
  • Built 1999

  19 Grosso Ct, Montgomery, NY 12549

  Last Sold Summary

  • 77 Days On Market
• 

  

  /39

  $699,999

  New Construction Open Sun 12PM - 2PM $50K PRICE DROP

  • 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
• 

  $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 $623,847

  Last Listing Agent Richard Baxter Keller Williams Realty

  135 Benedict Rd, Montgomery, NY 12549
• 

  Est $659,281

  Not Listed For Sale

  10 Dickerson Dr, Montgomery, NY 12549

  • 3 Beds
  • 2.5 Baths
  • 3,050 Sq Ft
  • Built 2001

  10 Dickerson Dr, Montgomery, NY 12549

  Last Sold Summary

  • 31 Days On Market
• 

  

  /37

  $724,999

  New Construction Open Sun 12PM - 2PM $25K PRICE DROP

  • 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
• 

  $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 $668,422

  Last Listing Agent Jordan Spordone HomeSmart Homes & Estates

  73 Tweddle Farm Ln, Montgomery, NY 12549
• 

  Est $624,219

  Not Listed For Sale

  182 W Searsville Rd, Montgomery, NY 12549

  • 4 Beds
  • 2.5 Baths
  • 2,034 Sq Ft
  • Built 2002

  182 W Searsville Rd, Montgomery, NY 12549

  Last Sold Summary

  • 28 Days On Market
• 

  

  /21

  $349,900

  Pending

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

  24 Emperor Ln, Montgomery, NY 12549

  Nestled at the top of a gentle hill in a quiet cul-de-sac, this 4-bedroom, oversized raised ranch offers a rare opportunity to create something truly special. Set on a one-acre parcel, the property provides both privacy and space—an ideal backdrop for your vision. Owned by the same family for over 50 years, this home is ready for its next chapter. While it requires updating and renovation, the

  Patricia Sassi RE/MAX Benchmark Realty Group

  24 Emperor Ln, 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 $540,783

  Last Listing Agent Thomas Lawrenson Howard Hanna Rand Realty

  1085 County Route 17, Montgomery, NY 12549
• 

  

  /94

  Est $1,150,495

  Not Listed For Sale

  278 Hill Ave, Montgomery, NY 12549

  • 4 Beds
  • 3.5 Baths
  • 3,700 Sq Ft
  • Built 1996

  278 Hill Ave, Montgomery, NY 12549

  Last Sold Summary

  • 147 Days On Market

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