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3 bedsNew constructionWith a pool
Homes Under $500K in Montgomery, NY
32 listings

Homes Under $500K in Montgomery, NY

Homes Under $500K in Montgomery, NY

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24 of 32 Listings
Map

Homes Under $500K in Montgomery, NY

24 of 32 Listings

  1. 30 Oakland Avenue — photo23Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #10311208632

Call Thomas

$439,900

4 bd · 2 ba · 2,000 sqft

30 Oakland Avenue, Montgomery, NY

Robin Kelly · Picture It Sold, LLC

  • 38 Valley Avenue — photo34Active

    $199,500

    4 bd · 2 ba · 1,440 sqft

    38 Valley Avenue, Montgomery, NY

    Robin D Cohen · Keller Williams Realty

  • 64 Enright Lane — photo15Active

    $449,900

    4 bd · 3 ba · 2,274 sqft

    64 Enright Lane, Montgomery, NY

    Brian T. Smith · River Realty Services, Inc.

  • 257 Orange Avenue — photo11Active

    $350,000

    2 bd · 1 ba · 944 sqft

    257 Orange Avenue, Montgomery, NY

    Margaret F Williams · Century 21 E & M Williams Rlty

  • 11 St Andrews Road — photo47Active

    $499,000

    4 bd · 2 ba · 1,564 sqft

    11 St Andrews Road, Montgomery, NY

    Virginia Corbett · eXp Realty

  • 19 Railroad Avenue — photo26Active

    $299,999

    2 bd · 1 ba · 1,168 sqft

    19 Railroad Avenue, Montgomery, NY

    Vincent Reda · Keller Williams Realty

  • 49 Bailey Road — photo49Active

    $454,900

    3 bd · 1 ba · 1,824 sqft

    49 Bailey Road, Montgomery, NY

    Richard Baxter · Keller Williams Realty

  • 995 State Route 17K — photo46Active

    $419,900

    3 bd · 2 ba · 1,104 sqft

    995 State Route 17K, Montgomery, NY

    Edwin G. Molina · RE/MAX Benchmark Realty Group

  • 140 N Drury Lane — photo33Active

    $350,000

    1 bd · 1 ba · 1,088 sqft

    140 N Drury Lane, Montgomery, NY

    George K Koudounas · RE/MAX Benchmark Realty Group

  • 77 Union Street — photoPrice Reduced48Active

    $449,999

    4 bd · 3 ba · 2,509 sqft

    77 Union Street, Montgomery, NY

    Vincent Reda · Keller Williams Realty

  • 158 High Meadows Road — photo43Active

    $499,999

    3 bd · 3 ba · 2,893 sqft

    158 High Meadows Road, Montgomery, NY

    Richard Baxter · Keller Williams Realty

  • 49 Gladstone Avenue — photo44Active

    $389,000

    4 bd · 2 ba · 1,308 sqft

    49 Gladstone Avenue, Montgomery, NY

    Pete Wolven · Hudson Valley Home Connection

  • 35 Highland Avenue — photo37Active

    $399,999

    2 bd · 1 ba · 1,180 sqft

    35 Highland Avenue, Montgomery, NY

    Richard Baxter · Keller Williams Realty

  • 168 Pleasant Avenue — photo22Active

    $479,900

    3 bd · 2 ba · 1,770 sqft

    168 Pleasant Avenue, Montgomery, NY

    Stacy Brescia-Spreer · Curasi Realty, Inc.

  • 38 Seely Street — photo28Active

    $325,000

    3 bd · 1 ba · 988 sqft

    38 Seely Street, Montgomery, NY

    Robert D. Villone · RE/MAX Classic Realty

  • 55 E Main Street — photoPrice Reduced22Active

    $215,000

    3 bd · 1 ba · 1,092 sqft

    55 E Main Street, Montgomery, NY

    Justin M. LaFalce · KW MidHudson

  • 132 North Montgomery Street C11 — photoPrice Reduced16Active

    $85,500

    2 bd · 1 ba · 840 sqft

    132 North Montgomery Street C11, Montgomery, NY

    Sandra Spector · Howard Hanna Rand Realty

  • 51 Mills Road — photoPrice Reduced32Active

    $375,000

    3 bd · 1 ba · 972 sqft

    51 Mills Road, Montgomery, NY

    Peter Panagiotis Kontrafouris · eXp Realty

  • 46 Pond Hill Lane — photoPrice Reduced38Active

    $385,000

    2 bd · 3 ba · 1,576 sqft

    46 Pond Hill Lane, Montgomery, NY

    Simone Barnes · RPM Westchester

  • 342 Coldenham Road — photo27Active

    $429,900

    3 bd · 2 ba · 1,276 sqft

    342 Coldenham Road, Montgomery, NY

    Louis J Shorette · Century 21 E & M Williams Rlty

  • 7 Lafayette Street — photoPrice Reduced34Active

    $424,999

    3 bd · 2 ba · 1,376 sqft

    7 Lafayette Street, Montgomery, NY

    Richard Baxter · Keller Williams Realty

  • 935 Homestead Avenue — photoPrice Reduced21Active

    $400,000

    3 bd · 2 ba · 2,288 sqft

    935 Homestead Avenue, Montgomery, NY

    Asa E Lennon · RE/MAX Benchmark Realty Group

  • 2812 State Route 208 — photoPrice Reduced31Active

    $309,900

    3 bd · 2 ba · 1,752 sqft

    2812 State Route 208, Montgomery, NY

    Suzanne Bongiorno · Century 21 E & M Williams Rlty

  • 36 Valley Avenue — photoPrice Reduced29Active

    $219,999

    3 bd · 2 ba · 1,216 sqft

    36 Valley Avenue, Montgomery, NY

    Richard Baxter · Keller Williams Realty

  • 12

    Explore Montgomery homes

    By price

    • Under $300K
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    • Under $700K
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    By bedrooms

    • 2 beds
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    By type

    • Single family
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    • Co-ops

    By feature

    • New construction
    • With a pool
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    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #10311208632

    Call Thomas

    Listing data & MLS disclosures

    OneKey MLS
    The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Copyright © 2026 OneKey MLS. All Rights Reserved

    Montgomery, NY community profile

    Population
    3,958
    Median income
    $92,197
    Housing units
    1,634
    People per sq. mi.
    97
    Area
    40.8 sq. mi.

    Source: HJN community data

    Montgomery housing market

    August 2026 · This period is still settling

    Homes on the market · MLS, as of Aug 24, 2026

    Median list price
    $672,000
    Homes for sale
    28

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Aug 19, 2026

    Median home size
    2,010 sq. ft.