Montgomery, NY Homes

/49
$719,900

$19K 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
$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 $400,442

Last Listing Agent Frank Gerbes RE/MAX Benchmark Realty Group

303 Chandler Ln, Montgomery, NY 12549

Est $562,150

Not Listed For Sale

87 Heritage Ln, Montgomery, NY 12549
- 3 Beds
- 2.5 Baths
- 2,080 Sq Ft
- Built 1994
87 Heritage Ln, Montgomery, NY 12549

Last Sold Summary
- 68 Days On Market

/49
$679,900
- 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
$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 $443,007

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

331 Lake Vue Dr, Montgomery, NY 12549

Est $754,058

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
- 34 Days On Market

/22
$399,000
- 2 Beds
- 1 Bath
- 928 Sq Ft
1084 State Route 17k, Montgomery, NY 12549

Enjoy peaceful living in this charming, newly updated private ranch set on over one acre of beautiful property. This inviting home offers the perfect blend of comfort and convenience, featuring a beautifully renovated kitchen and bathroom with modern finishes throughout. A new roof adds additional value and peace of mind.Imagine having a golf course right in your backyard! This property

Larry Curasi Curasi Realty, Inc.

1084 State Route 17k, Montgomery, NY 12549
$475,000

Sold Jun 15, 2026

205 Oriole Dr, Montgomery, NY 12549
- 3 Beds
- 1.5 Baths
- 1,692 Sq Ft
- Built 1973
Last Sold Summary
- 3% Below List Price
- $281/SF
- 220 Days On Market
Current Estimated Value $469,428

Last Listing Agent Rose Daversa Hudson Valley Home Connection

205 Oriole Dr, Montgomery, NY 12549

Est $750,404

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
- 55 Days On Market

/33
$229,900

Pending
- 2 Beds
- 1 Bath
- 1,137 Sq Ft
506 Berea Rd, Montgomery, NY 12549

Discover the potential of 506 Berea Road, a unique real estate opportunity located in the scenic town of Montgomery New York. This property is hitting the market for the first time in over forty years, having been held by the same owner since 1982. For buyers searching for a true Hudson Valley fixer upper or a rewarding investment property in Orange County, this ranch style home offers the

Matthew Gibbs KW Hudson Valley United

506 Berea Rd, 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 $787,922

Last Listing Agent Richard Baxter Keller Williams Realty

200 Hill Ave, Montgomery, NY 12549

Est $482,481

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
- 47 Days On Market

/31
$269,000

$11K PRICE DROP
- 2 Beds
- 1 Bath
- 584 Sq Ft
20 Barron Rd, Montgomery, NY 12549

Newly added! A Pioneer mini split for central air (comes thru existing ducts)! And, the exterior has been freshly painted! This sweet ranch is perfect for 1st time home buyers, or people that just like to have really low living expenses! You'll enjoy the large deck off the kitchen for enjoying BBQ's or hanging outside. You'll also enjoy the small & quiet neighborhood! At the end of Barron Rd, is

Kathy Dawson Howard Hanna Rand Realty

20 Barron Rd, 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 $547,695

Last Listing Agent Richard Baxter Keller Williams Realty

317 Angelo Dr, Montgomery, NY 12549

Est $551,930

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
- 20 Days On Market

/2
$499,000

$60K PRICE DROP
- Land
- 7.6 Acres
- $65,658 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 KW Hudson Valley United

0 New York 17k, 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 $494,496

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
- 42 Days On Market

/50
$2,499,900
- 3 Beds
- 3 Baths
- 3,448 Sq Ft
95 Judson Rd, Montgomery, NY 12549

Welcome to one of the Hudson Valley's most iconic private estates; an extraordinary 38+ acre retreat offering luxury, recreation, equestrian amenities, abundant space for custom vehicle enthusiasts and unmatched entertaining spaces. Known locally as the famed "Orange County Choppers House," this remarkable property blends rustic elegance with modern comfort in a setting designed for those who

Danielle Bartula Howard Hanna Rand Realty

95 Judson Rd, 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 $541,986

Last Listing Agent Richard Baxter Keller Williams Realty

12 Sycamore Dr, Montgomery, NY 12549

Est $477,924

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
- 22 Days On Market

/36
$599,000
- 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 apartment 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
$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 $597,087

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
- 25 Days On Market

/25
$675,000
- 5 Beds
- 3 Baths
- 2,982 Sq Ft
40 Bailey Rd, Montgomery, NY 12549

Welcome to this exceptional ranch-style home offering the perfect combination of space, versatility, and lifestyle. Thoughtfully designed and currently configured as a sprawling single-family residence, this home provides an ideal setup for today's multi-generational living with separate areas that offer both privacy and togetherness. The main level features 3 spacious bedrooms, 2 full baths, an

Nancy LaBarbera KW Hudson Valley United

40 Bailey 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
Current Estimated Value $445,678

Last Listing Agent Larry Curasi Curasi Realty, Inc.

114 Union St, Montgomery, NY 12549

Est $768,390

Not Listed For Sale

3 Eleanor Dr, Montgomery, NY 12549
- 4 Beds
- 3 Baths
- 3,870 Sq Ft
- Built 2002
3 Eleanor Dr, Montgomery, NY 12549

Last Sold Summary
- 26 Days On Market

/50
$975,000

Open Sun 11AM - 12:30PM
- 7 Beds
- 4.5 Baths
- 1,632 Sq Ft
97 Svenski Rd, Montgomery, NY 12549

A private luxury retreat unlike anything else on the market. Set on 54.10 secluded acres at the end of a long private driveway, 97 Svenski offers an extraordinary combination of privacy, distinctive modern design, smart-home features, and fully renovated, move-in-ready living. This one-of-a-kind residence features 7 bedrooms, 4.5 bathrooms, 1,632+ sq. ft. above grade, plus an additional 1,006 sq.

Leon Klein Keller Williams Hudson Valley

97 Svenski Rd, 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 $662,039

Last Listing Agent Philip Szumlaski Keller Williams Realty

560 Winding Hill Rd, Montgomery, NY 12549

Est $594,830

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
- 221 Days On Market

/35
$499,000
- 5 Beds
- 2.5 Baths
- 2,360 Sq Ft
82 Wallkill Ave, Montgomery, NY 12549

LOVELY HISTORIC HOME IN THE VILLAGE OF MONTGOMERY! This 2360 sq.ft. home has a lot to offer, historical charm with hardwood floors, an old wooden staircaseand a claw foot tub, yet all the conveniences to suit your needs. Five bedrooms with 2-1/2 bathrooms and a spacious walk-up attic. This corner lot features a great deal of privacywith a beautiful in ground pool. There is plenty of room

Stacy Brescia-Spreer Curasi Realty, Inc.

82 Wallkill Ave, 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 $498,271

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
- 30 Days On Market

/43
$719,000

Pending
- 4 Beds
- 2.5 Baths
- 2,984 Sq Ft
15 Ferrante Dr, Montgomery, NY 12549

There are homes and then there are homes filled with a lifetime of memories. Tucked in a small, quiet cul-de-sac in the Valley Central school district, this center hall colonial has been lovingly cared for by its original owners-- holidays were celebrated and the rhythms of everyday life became something truly meaningful. Hardwood floors carry throughout, grounding each space with a sense of

Patricia Sassi RE/MAX Benchmark Realty Group

15 Ferrante Dr, 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 $442,036

Last Listing Agent Maureen Cronin Cronin & Company Real Estate

24 Taft Ave, Montgomery, NY 12549

Est $294,343

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
- 26 Days On Market

/50
$475,000
- 4 Beds
- 2.5 Baths
- 2,288 Sq Ft
11 Kevin Ct, Montgomery, NY 12549

Welcome home to this spacious 4-bedroom, 3 bath residence with finished lower level on a cul-de-sac including a full acre of land! Solidly maintained with newer roof and updated systems (h/w heater, furnace). Offering space, flexibility, and comfort both inside and out. The home features a top floor open-concept layout filled with natural light and an inviting eat-in kitchen, creating the perfect

Amanda Ferrantello Hudson Valley Griffith

11 Kevin Ct, Montgomery, NY 12549
$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 $395,507

Not Listed For Sale

12 New Rd, Montgomery, NY 12549
- 3 Beds
- 1.5 Baths
- 1,600 Sq Ft
- Built 1941
12 New Rd, Montgomery, NY 12549

Last Sold Summary
- 60 Days On Market

/49
$474,900

$85K PRICE DROP
- 3 Beds
- 3 Baths
- 2,096 Sq Ft
68 Weaver St, Montgomery, NY 12549

Looking for a quiet home in Montgomery with space to relax and grow? This 3-bedroom, 3-bath home at 68 Weaver Street offers a comfortable layout, thoughtful updates throughout, and a peaceful neighborhood feel—all within the Valley Central School District. This home comes with valuable upgrades including a renovated kitchen, updated roof, and finished basement, giving you peace of mind and

Matthew Gibbs KW Hudson Valley United

68 Weaver St, Montgomery, NY 12549

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