Middlebury, VT Homes for Sale under $600,000

/50
$529,000

$20K PRICE DROP
- 1,960 Sq Ft
2337 Vt Route 7, Middlebury, VT 05753

Here is a delightful opportunity to own a simply versatile property that has been carefully updated over the years. What started as a single family home has been beautifully transformed to this multi-use property. The larger section of the property includes 5 privately rented office spaces that share a conference room and a reception area as well as a full bath and small kitchenette. The total

Amey Ryan

IPJ Real Estate

2337 Vt Route 7, Middlebury, VT 05753
Explore Middlebury
/31
$549,000

$146K PRICE DROP
- 4 Beds
- 2 Baths
- 2,037 Sq Ft
30 South St, Middlebury, VT 05753

This classic village home is in a great location! Situated on South St., with sidewalks on both sides of the historical street as you head into town. You have no doubt driven by this home and admired its handsome Colonial facade many times. A brand new natural gas boiler has been installed! From the front door you enter into the living room space, with wood floors that continue throughout the

Sarah Peluso

IPJ Real Estate

30 South St, Middlebury, VT 05753
/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

Levi Doria

IPJ Real Estate

26 and 28 Kings Row, Middlebury, VT 05753
/7
$595,000

$30K PRICE DROP
- Land
- 7.2 Acres
- $82,639 per Acre
1332 Cider Mill Rd, Middlebury, VT 05753

This location does not come along often! Sited on the east side of Cider Mill road looking towards Middlebury College and the Green Mountains, and just 2.5 miles to downtown. Over 7 acres of land has been opened up to share the incredible eastern views. There is an old farmhouse on this land that is not currently livable. It would require a complete transformation or a new owner could start

Sarah Peluso

IPJ Real Estate

1332 Cider Mill Rd, 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,

Sarah Peluso

IPJ Real Estate

86 Birch Dr Unit 10.7, Middlebury, VT 05753
/8
$585,000

New Construction
- 2 Beds
- 1.5 Baths
- 1,516 Sq Ft
39 Barnes Brook Rd Unit 9.3, 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

Sarah Peluso

IPJ Real Estate

39 Barnes Brook Rd Unit 9.3, 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

Sarah Peluso

IPJ Real Estate

41 Barnes Brook Rd Unit 9.2, 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

Sarah Peluso

IPJ Real Estate

35 Barnes Brook Rd Unit 9.4, 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
/48
$549,000
- 3 Beds
- 2 Baths
- 1,976 Sq Ft
2801 Route 7 S, Middlebury, VT 05753

Looking for somewhere truly special to call home? This exceptional property offers 2,140 square feet of beautifully finished living space with 3 bedrooms, 2 baths, and breathtaking Green Mountain views from its private backyard and expansive deck. Meticulously rebuilt from top to bottom by the builder-owner, this home delivers the quality, efficiency, and peace of mind of new construction.

Rob Foley Flat Fee Real Estate

2801 Route 7 S, 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
/49
$549,000
- 5 Beds
- 4.5 Baths
- 3,630 Sq Ft
21 Seminary St, Middlebury, VT 05753

Built in 1813 by Timothy C. Strong, a Middlebury printer, 21 Seminary Street is an example of slow days from a different time. The property still boasts unique historical details like 25 inch wide pine flooring as well as the original staircase to the second floor. The home is currently setup as a single family with an apartment in the rear of the first floor, but is zoned to allow multiple

Katrina Roberts Vermont Real Estate Company

21 Seminary 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

Vermont Addison County

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 $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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Middlebury Types of Homes for Sale

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