The picturesque town of Middlebury is where you can find a friendly blend of small-town warmth and cultural depth., and is home to the prestigious Middlebury College. Dine, shop, or attend the theater in Middlebury's downtown. Burlington is just a short drive away, but you will never feel forced to make the trip with all of the services, shopping, and entertainment you need just minutes away.

The mountains, forests, and lakes invite you to pack a picnic, jump into a swimming hole, hike trails, or go camping. In the summer golf, tennis, and biking are popular pastimes, as well as enjoying nearby Lake Champlain. In the winter cross-country skiing or downhill skiing at the Middlebury College Snow Bowl are just a few ways to enjoy the snow.

Search our complete listing of homes & real estate for sale in Middlebury, Vermont.

27 Currently Available
87 Cottage Lane, Middlebury

87 Cottage Lane

Middlebury

Price: $360,000

MLS# 4866821

House
3
3
1,819
0.15
2012
$7,055
6/15/21
For Sale
11 Elm Street, Middlebury

11 Elm Street

Middlebury

Price: $279,000

MLS# 4866591

House
3
2
1,233
0.04
1912
$5,531
6/14/21
For Sale
424 Quarry Road, Middlebury

424 Quarry Road

Middlebury

Price: $424,900

MLS# 4866169

House
4
3
2,790
1.04
1984
NA
6/11/21
For Sale
288 Weybridge Street, Middlebury

288 Weybridge Street

Middlebury

Price: $729,000

MLS# 4865190

House
3
3
3,732
0.67
1981
$12,852
6/07/21
For Sale
46 Ossie Road, Middlebury

46 Ossie Road

Middlebury

Price: $340,000

MLS# 4865109

House
3
3
1,694
0.3
1957
$4,716
6/07/21
For Sale
1 Stonegate Drive, Middlebury

1 Stonegate Drive

Middlebury

Price: $315,000

MLS# 4864837

House
2
2
1,885
0.08
1992
$5,491
6/04/21
6/08/21
For Sale with Contract
2263 Route 7 South, Middlebury

2263 Route 7 South

Middlebury

Price: $379,000

MLS# 4864481

House
3
3
1,992
1.8
1958
$7,230
6/03/21
6/08/21
For Sale with Contract
442 East Main Street, Middlebury

442 East Main Street

Middlebury

Price: $260,000

MLS# 4863611

House
4
2
1,815
0.26
1870
$4,198
5/29/21
For Sale
229 Daisy Lane, Middlebury

229 Daisy Lane

Middlebury

Price: $375,000

MLS# 4862146

House
3
3
1,680
0.58
2017
$6,935
5/21/21
5/25/21
For Sale with Contract
92 Grand View Road, Middlebury

92 Grand View Road

Middlebury

Price: $225,000

MLS# 4860966

House
2
2
1,764
0.11
1990
$4,299
5/15/21
For Sale
999 Happy Valley Road, Middlebury

999 Happy Valley Road

Middlebury

Price: $425,000

MLS# 4860683

House
3
2
2,459
1.21
1900
$7,633
5/13/21
5/31/21
For Sale with Contract
61 Seminary St Extension, Middlebury

61 Seminary St Extension

Middlebury

Price: $750,000

MLS# 4859708

Land
Residential
29.2
Ft
5/08/21
For Sale
48 Court Street, Middlebury

48 Court Street

Middlebury

Price: $275,000

MLS# 4859381

House
4
2
1,548
0.28
1900
NA
5/06/21
5/24/21
For Sale with Contract
Lot 4-5 Mead Lane, Middlebury

Lot 4-5 Mead Lane

Middlebury

Price: $99,900

MLS# 4859241

Land
R
3.74
500 Ft
5/05/21
For Sale
6 Cones Road, Middlebury

6 Cones Road

Middlebury

Price: $250,000

MLS# 4858734

House
2
2
1,430
0.59
1975
$4,857
5/01/21
6/07/21
For Sale with Contract
13 Washington Street Extension, Middlebury

13 Washington Street Extension

Middlebury

Price: $545,000

MLS# 4857230

Multi-Family
4
4
4
3,618
1850
$9,644
4/23/21
For Sale
13 Washington Street Extension, Middlebury

13 Washington Street Extension

Middlebury

Price: $545,000

MLS# 4857227

House
5
5
3,618
0.51
1850
$9,644
4/23/21
For Sale
147 Rolling Acres, Middlebury

147 Rolling Acres

Middlebury

Price: $349,500

MLS# 4856376

House
3
2
1,366
0.64
1965
$5,709
4/19/21
5/19/21
For Sale with Contract
39 Court Street, Middlebury

39 Court Street

Middlebury

Price: $289,000

MLS# 4856329

House
3
2
1,511
0.32
1900
$4,595
4/19/21
5/11/21
For Sale with Contract
31 Evergreen Lane, Middlebury

31 Evergreen Lane

Middlebury

Price: $249,000

MLS# 4856292

Condo
2
2
1,397
1984
$4,730
4/18/21
4/22/21
For Sale with Contract
TBD Munger Street, Middlebury

TBD Munger Street

Middlebury

Price: $550,000

MLS# 4853578

Land
AR
98
1000 Ft
4/01/21
For Sale
3472 Case Street, Middlebury

3472 Case Street

Middlebury

Price: $199,000

MLS# 4852383

House
3
1
1,524
0.89
1910
$4,554
3/24/21
For Sale
0 Case Street, Middlebury

0 Case Street

Middlebury

Price: $125,000

MLS# 4844269

Land
Agricultural/residential
26.89
800 Ft
1/14/21
For Sale
2815 South St. Extension, Middlebury

2815 South St. Extension

Middlebury

Price: $449,000

MLS# 4835836

House
4
2
1,768
5.35
1977
$8,111
10/23/20
5/04/21
For Sale with Contract
36 Seymour Street, Middlebury

36 Seymour Street

Middlebury

Price: $269,000

MLS# 4823828

House
4
2
2,048
0.34
1875
$4,819
8/16/20
For Sale
TBD Route 7 South, Middlebury

TBD Route 7 South

Middlebury

Price: $350,000

MLS# 4639868

Land
AR
111.3
670 Ft
6/09/17
3/15/21
For Sale with Contract
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