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Bennington Homes for Sale

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  • /50

    $629,900

    $20K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,554 Sq Ft

    1589 Bailey Rd, Cowlesville, NY 14037

    Welcome to 1589 Bailey Rd, a one-of-a-kind custom-built ranch nestled on 5 acres! Built in 2002, this impressive home offers approx. 3,500 sq. ft. of living space (per plans), featuring 4 beds, 3 full baths & 1 half bath. A property like this is nearly impossible to duplicate at today's construction costs.Step inside to an inviting open-concept layout with soaring vaulted ceilings &

    Sarah Kieffer Listing by HUNT Real Estate ERA

    1589 Bailey Rd, Cowlesville, NY 14037
  • /19

    $249,000

    • Land
    • 25.3 Acres
    • $9,842 per Acre

    0 Tinkham Rd Unit B1712401, Bennington, NY 14011

    Holy opportunity with this incredible acreage on Tinkham Road in Bennington. Enjoy the entire 25 acres for yourself and/or the ability for (5) five acre building lots. Almost 1600' of road frontage. Beautiful, wooded lots, a dream back drop for your new build! Awesome recreational land with wildlife abound! Delayed negotiations through Monday, September 14, 2026 @ 2PM.

    Susan Kautz Listing by Howard Hanna Rochester Inc.

    0 Tinkham Rd Unit B1712401, Bennington, NY 14011
  • /50

    $485,000

    $110K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,825 Sq Ft

    311 Ortner Rd, Darien Center, NY 14040

    Set on a stunning 17-acre parcel, on a country road located on the edge of a wooded area this charming and unique 4-bedroom, 2 full bath 'Geodesic Home' offers the perfect blend of privacy, nature, and comfort. Surrounded by mature gardens and scenic hiking trails, the property invites you to enjoy the outdoors year-round. A large pond provides the ideal setting for fishing, swimming, or simply

    Bridget Rivellino Listing by Rivellino Realty

    311 Ortner Rd, Darien Center, NY 14040
  • /40

    $399,900

    $10K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,116 Sq Ft

    13 N Shore Dr, Alden, NY 14004

    Wake up to the sound of the water and sip your morning coffee from your back deck overlooking the lake. This is the lifestyle 13 n Shore delivers. Tucked away in a private setting with a true backyard oasis, this 4-bed, 3-bath multi-level home blends comfortable everyday living with spectacular outdoor access. The main level welcomes you with a bright, open living room featuring a fireplace and

    Wendy Dominique Listing by Nichol City Realty

    13 N Shore Dr, Alden, NY 14004
  • /19

    $50,000

    $10K PRICE DROP
    • 4 Beds
    • 1 Bath
    • 1,836 Sq Ft

    270 Clinton St, Cowlesville, NY 14037

    Good Bones and History is what you get with 270 Clinton St. This home has had the same family for over 100 years. Now it is time for a fresh start and the next chapter of history. Sitting on just over an acre this home features newer furnace and HWT. No space was spared as this house has room after room. 5 rooms upstairs with two entry ways. 6 more rooms downstairs with spacious dining room at

    Matthew Foss Listing by Trank Real Estate

    270 Clinton St, Cowlesville, NY 14037
  • /2

    $250,000

    • 5 Beds
    • 3 Baths
    • 2,392 Sq Ft

    246 Clinton St, Cowlesville, NY 14037

    Solid rental in high demand area. Side by side unit. 3 bedrooms and 2 full bath owner unit. 2 bedrooms and 1 bath. Additional barn for parking or storage.

    Joseph Wyzykiewicz Listing by HUNT Real Estate ERA

    246 Clinton St, Cowlesville, NY 14037

Bennington, NY, NY Home Prices vs. Nearby Neighborhoods

Bennington Darien Sheldon Marilla
Median Home Price
$309,000
$219,949
$324,450
$382,450
Median Sale Price
$304,000
+2% YoY
$285,000
-14% YoY
$375,500
+65% YoY
$370,000
+2% YoY
Median Single Family Price
$305,000
$260,000
$300,000
$397,500
Total Active Listings
4 listings
3 listings
4 listings
7 listings
Market Conditions
2 Months of Supply
Seller's Market
2 Months of Supply
Seller's Market
3 Months of Supply
Seller's Market
3 Months of Supply
Seller's Market

Frequently Asked Questions Why Live in Bennington

Is Bennington a good place to live?
Bennington is a good place to live. It has a median age of 50. The average household income is $102,860 which is below the national average. College graduates make up 23.4% of residents. A majority of residents in Bennington are home owners, with 11% of residents renting and 89% of residents owning their home. A local real estate agent serving Bennington can help you decide if this neighborhood is the right one for you. Learn more on our Bennington neighborhood guide.
How much do you need to make to afford a house in Bennington?
The median home price in Bennington is $309,000. If you put a 20% down payment of $61,800 and had a 30-year fixed mortgage with an interest rate of 6.71%, your estimated principal and interest payment would be $1,600 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $69K a year to afford the median home price in Bennington. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Bennington is $103K.
What are the best public schools in Bennington?
The best public schools that serve Bennington are:
What are the most popular zip codes in Bennington, Bennington, NY?
The most popular zip codes in Bennington, Bennington, NY include 14011, 14040, 14004, 14052 and 14167.
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