6

Middlebury, VT Homes for Sale under $300,000

Section Image Section Image
  • 11 Ledgewood Ct, Middlebury, VT 05753
    11 Ledgewood Ct, Middlebury, VT 05753
    11 Ledgewood Ct, Middlebury, VT 05753
    /20

    $237,500

    • 3 Beds
    • 1 Bath
    • 1,122 Sq Ft

    11 Ledgewood Ct, Middlebury, VT 05753

    Welcome to this well-maintained 3-bedroom, 1-bath condominium in beautiful Middlebury, Vermont. This location is ideal for easy access to local shops, restaurants and parks and offers low-maintenance living. Inside, you'll find a bright, functional layout featuring newer carpeting, new kitchen appliances, and a new washer & dryer creating a fresh and inviting space to call home. The three

    Agent Photo

    Beth Stanway

    IPJ Real Estate

    11 Ledgewood Ct, Middlebury, VT 05753
  • TBD Route 7 S, Middlebury, VT 05753
    TBD Route 7 S, Middlebury, VT 05753
    TBD Route 7 S, 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
  • 2 Wilmar St, Middlebury, VT 05753
    2 Wilmar St, Middlebury, VT 05753
    2 Wilmar St, Middlebury, VT 05753
    /7

    $150,000

    • Land
    • 23,522 Sq Ft
    • $277,778 per Acre

    2 Wilmar St, Middlebury, VT 05753

    BUILD THE SOLUTION. Address the high demand for residential space in Middlebury with this fully permitted & shovel-ready parcel. Whether you're envisioning modern multi-unit apartments or an eco-village, this lot is engineered for efficiency & affordability. Permitted for up to12 Bedrooms: Ideal for a high-occupancy single-family home or large-scale multi-bedroom apartment units. Substantial

    Jason Saphire www.HomeZu.com

    2 Wilmar St, Middlebury, VT 05753
  • 76 N Forty Ln, Middlebury, VT 05753
    76 N Forty Ln, Middlebury, VT 05753
    76 N Forty Ln, Middlebury, VT 05753
    /30

    $299,000

    • 3 Beds
    • 2 Baths
    • 1,836 Sq Ft

    76 N Forty Ln, Middlebury, VT 05753

    Welcome to this well-maintained home offering comfortable one-level living on 1.4 wooded acres in a peaceful country setting. With over 1,800 square feet of living space, this 3-bedroom, 2-bath home features a spacious layout with generously sized rooms and plenty of opportunity to make it your own. The primary suite offers a private bath and ample closet space, while the additional bedrooms

    Brittanie Caggige Vermont Real Estate Company

    76 N Forty Ln, Middlebury, VT 05753
  • 4 Wilmar St, Middlebury, VT 05753
    4 Wilmar St, Middlebury, VT 05753
    4 Wilmar St, Middlebury, VT 05753
    /7

    $150,000

    • Land
    • 22,651 Sq Ft
    • $288,462 per Acre

    4 Wilmar St, Middlebury, VT 05753

    BUILD THE SOLUTION. Address the high demand for residential space in Middlebury with this fully permitted & shovel-ready parcel. Whether you're envisioning modern multi-unit apartments or an eco-village, this lot is engineered for efficiency & affordability. Permitted for up to12 Bedrooms: Ideal for a high-occupancy single-family home or large-scale multi-bedroom apartment units. Substantial

    Jason Saphire www.HomeZu.com

    4 Wilmar St, Middlebury, VT 05753
  • 89 Court St, Middlebury, VT 05753
    89 Court St, Middlebury, VT 05753
    89 Court St, 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
Vermont Addison County

Real Estate & Homes in Middlebury, VT under $300,000

Home Prices in Middlebury, VT

The median home sale price in Middlebury, VT is $480,000, up 14% year-over-year. Homes in Middlebury sell in 64 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price
$480,000
Median Single Family Sale Price
$495,000
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
$308
Number of Homes for Sale
20
Last 12 months Home Sales
84
Months of Supply
2.90
Median List Price
$488,600
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
14%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is 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.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group