Montgomery, NY Homes

• 

  

  

  /50

  $749,999

  • 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

• 

  

  

  /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
• 

  

  

  /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 $745,987

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

  95 Heritage Ln, Montgomery, NY 12549
• 

  Est $657,194

  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
• 

  

  

  /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
• 

  

  /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
• 

  $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
• 

  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
• 

  

  /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
• 

  $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
• 

  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
• 

  

  /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
• 

  

  /99

  $3,000

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • 1,290 Sq Ft
  • Condo for Rent

  1085 County Route 17 Unit Luxury Log Apartment, Montgomery, NY 12549

  Charming nearly 1300 sq foot Luxury Log Home Apartment – 2BR 1 BA in Montgomery, NY - Your Private Retreat Awaits!This stunning luxury log home apartment, tucked into a private, wooded area of Montgomery, NY, offers the perfect escape from the daily grind.Why You'll Love This Location:There's something powerful about coming home at the end of the day to a private place

  1085 County Route 17 Unit Luxury Log Apartment, 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 $645,164

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

  38 Wavey Willow Ln, Montgomery, NY 12549
• 

  Est $590,157

  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
• 

  

  /35

  $349,999

  Pending

  • 1 Bed
  • 1 Bath
  • 1,098 Sq Ft

  36 Charles St, Montgomery, NY 12549

  Welcome to this charming Ranch-style home beautifully nestled on a corner lot in the Village of Montgomery within the Valley Central School District. Showcasing lovely curb appeal with a landscaped front yard, this inviting 1-bedroom, 1-bathroom residence features a versatile office or bonus room to suit your lifestyle. Step inside to discover a bright living room highlighted by gleaming hardwood

  

  Richard Baxter

  Keller Williams Realty

  36 Charles St, Montgomery, NY 12549
• 

  

  /8

  $1,450 Per Month

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

  1232 State Route 17k Unit 1, Montgomery, NY 12549

  Valley Central School District! Nestled on the outskirts of the charming village of Montgomery, this exquisite apartment offers a rare blend of convenience and serenity. Situated on a sprawling four-acre lot, the property boasts a picturesque setting with a private pond, creating an idyllic haven for those seeking a peaceful retreat.

  Timothy Sheehan Keller Williams Realty

  1232 State Route 17k Unit 1, 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 $456,764

  Last Listing Agent Tremaine Selby Weichert Realtors

  201 Tompkins Rd, Montgomery, NY 12549
• 

  Est $783,535

  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
• 

  

  /33

  $399,999

  Pending

  • 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
• 

  

  /30

  $4,000 Per Month

  • 4 Beds
  • 2 Baths
  • 3,472 Sq Ft
  • House for Rent

  55 Union St, Montgomery, NY 12549

  Beautiful Village Colonial for Rent in the Heart of Montgomery – Utilities Included!Experience the charm of village living in this beautifully maintained 4-bedroom, 2-bath Colonial, ideally located in the quaint Village of Montgomery. Blending timeless character with modern updates, this spacious home features a grand foyer, wide plank pine floors, a formal living room and dining room, and an

  Annette Bauer Century 21 E & M Williams Rlty

  55 Union St, 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
• 

  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
• 

  

  /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
• 

  

  /50

  $4,000 Per Month

  • 2 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • House for Rent

  718 River Rd, Montgomery, NY 12549

  Furnished Farmhouse Retreat on 23-Acre Horse Farm: $4,000/MonthEscape to serene country living with this furnished farmhouse, available for a 6-month rental from November 1, 2026 to April 30, 2027, for $4,000 per month. This charming home offers two bedrooms plus a versatile den/office and 2.5 baths, providing ample space for comfortable living.Embrace the tranquility of the countryside

  Annette Bauer Century 21 E & M Williams Rlty

  718 River Rd, Montgomery, NY 12549
• 

  $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 $250,484

  Last Listing Agent Matthew Gibbs KW Hudson Valley United

  506 Berea Rd, Montgomery, NY 12549
• 

  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
• 

  

  /38

  $724,999

  New Construction $25K 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
• 

  

  /5

  $1,350 Per Month

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

  49 Walnut St Unit 3, Montgomery, NY 12549

  Hardwood floors will be redone prior to new tenant moving in!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

  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 $361,950

  Last Listing Agent Lynelle Alessi KW Hudson Valley United

  241 Freida St, Montgomery, NY 12549
• 

  Est $630,803

  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

  Last Listing Agent Richard Froehlich RE/MAX Benchmark Realty Group
• 

  

  /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
• 

  $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 $477,680

  Last Listing Agent Frank Muccari Cronin & Company Real Estate

  269 Wilson St, Montgomery, NY 12549
• 

  Est $669,163

  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

  Last Listing Agent Simone Edwards Edwards Properties
• 

  

  /49

  $699,000

  $40K 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
• 

  $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
• 

  Est $663,912

  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

  Last Listing Agent Richard Baxter Keller Williams Realty
• 

  

  /49

  $679,900

  Pending

  • 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
• 

  $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 $670,854

  Last Listing Agent Jordan Spordone HomeSmart Homes & Estates

  73 Tweddle Farm Ln, Montgomery, NY 12549

Showing Results 1 - 40, Page 1 of 18