9

Middlebury, VT Homes for Sale under $500,000

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  • /29

    $399,000

    $74K PRICE INCREASE
    • 3 Beds
    • 1 Bath
    • 1,724 Sq Ft

    26 and 28 Kings Row, Middlebury, VT 05753

    ***NEW PRICING*** Now includes +/- .48 building lot located at 28 Kings Row. Property has tremendous potential with the ability to purchase two lots. 26 Kings has a thoughtfully designed one-level home tucked away off the town maintained cul-de-sac, offering tranquility and privacy while keeping you close to the convenience and amenities of downtown living. Located at the end of Kings Row, the

    Agent Photo

    Levi Doria

    IPJ Real Estate

    26 and 28 Kings Row, Middlebury, VT 05753
  • /14

    $220,000

    • Land
    • 9.8 Acres
    • $22,449 per Acre

    TBD Route 7 S, Middlebury, VT 05753

    Great piece of land in a great location! Secluded when you go up the old road/driveway. Easy access to Rutland or Burlington. Close to everything Middlebury has to offer including stores, restaurants and Middlebury College.

    Agent Photo

    Beth Stanway

    IPJ Real Estate

    TBD Route 7 S, Middlebury, VT 05753
  • /5

    $388,900

    New Construction
    • 2 Beds
    • 1.5 Baths
    • 1,516 Sq Ft

    35 Barnes Brook Rd Unit 9.4, Middlebury, VT 05753

    Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This two-bedroom townhome will be ready for occupancy in May of 2026. With energy efficiency at the forefront, each unit will

    Agent Photo

    Sarah Peluso

    IPJ Real Estate

    35 Barnes Brook Rd Unit 9.4, Middlebury, VT 05753
  • /6

    $499,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,938 Sq Ft

    86 Birch Dr Unit 10.7, Middlebury, VT 05753

    Special pricing for qualified buyers! Inquire with your agent to see if you qualify. Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This three-bedroom duplex will be ready for occupancy in the fall of 2026. To be built with energy efficiency at the forefront,

    Agent Photo

    Sarah Peluso

    IPJ Real Estate

    86 Birch Dr Unit 10.7, Middlebury, VT 05753
  • /8

    $388,900

    New Construction
    • 2 Beds
    • 1.5 Baths
    • 1,516 Sq Ft

    41 Barnes Brook Rd Unit 9.2, Middlebury, VT 05753

    Welcome to Stonecrop Meadows, Middlebury's newest neighborhood! Located just 1/2 mile from downtown Middlebury, where restaurants, shopping, theater, and more will be at your fingertips. This two-bedroom townhome will be ready for occupancy in May 2026. To be built with energy efficiency at the forefront, each unit will be heated and cooled with mini split technology, with a whole-house

    Agent Photo

    Sarah Peluso

    IPJ Real Estate

    41 Barnes Brook Rd Unit 9.2, Middlebury, VT 05753
  • /43

    $479,000

    $70K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 2,213 Sq Ft

    35 Ossie Rd, Middlebury, VT 05753

    Spacious East Middlebury Ranch on 1.20 Acres with Mountain ViewsSet on a generous 1.20-acre lot with a beautiful Green Mountain backdrop, this inviting ranch-style home offers comfort, flexibility, and room to grow. The property includes an attached two-car garage plus a separate detached building—perfect for hobbies, a workshop, or a small business—complete with its own power supply. Home

    Roxanna Emilo Emilo Real Estate, LLC

    35 Ossie Rd, Middlebury, VT 05753
  • /33

    $400,000

    $49K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,815 Sq Ft

    442 E Main St, Middlebury, VT 05753

    This inviting home offers a bright, comfortable layout designed for easy everyday living. The main level flows naturally between the kitchen, dining and living spaces, creating a welcoming environment for gatherings or quiet evenings at home. The updated kitchen blends the convenience of modern living with the charm and character of an older home. Upstairs, a large full bath serves the bedroom

    Heather Foster-Provencher Champlain Valley Properties

    442 E Main St, Middlebury, VT 05753
  • /28

    $489,000

    $16K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,916 Sq Ft

    95 Seminary Street Extension, Middlebury, VT 05753

    OPEN HOUSE JULY 19TH from 1 to 3PM! Buyer Brokers honored. This updated mid-century home features new flooring and fresh interior paint. Step outside onto the new back deck — the perfect place to entertain, relax, and take in views of your own private slice of Vermont.Set on 1.1 acres, the property offers plenty of space for a vegetable garden and complements the existing perennial plantings.

    Sean Dye BHHS Vermont Realty Group/Vergennes

    95 Seminary Street Extension, Middlebury, VT 05753
  • /56

    $299,000

    • 4 Beds
    • 2 Baths
    • 1,344 Sq Ft

    89 Court St, Middlebury, VT 05753

    This vintage farmhouse-style home is full of character and classic architectural details. Original woodwork, solid wood doors, hardwood floors, and a seasonal sleeping porch showcase the home's timeless appeal. The main level features a centrally located propane stove in the living room, a spacious kitchen, and a first-floor bedroom with 3⁄4 bathroom. Upstairs, you'll find three additional

    Bianca Perta Coldwell Banker Hickok and Boardman

    89 Court St, Middlebury, VT 05753

Home Price Trends

Median Sale Price
$480,000
Median Single Family Sale Price
$499,000
Median Townhouse Sale Price
$425,000
Median 2 Bedroom Sale Price
$425,000
Median 1 Bedroom Sale Price
$139,000
Average Price Per Sq Ft
$309
Number of Homes for Sale
19
Last 12 months Home Sales
84
Months of Supply
2.70
Median List Price
$494,700
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
14%
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