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
216 Washington St Extension, Middlebury

216 Washington St Extension

Middlebury

Price: $315,000

MLS# 4820362

House
3
2
1,203
0.42
1952
$4,374
8/03/20
For Sale
70 Maple Street, Middlebury

70 Maple Street

Middlebury

Price: $359,000

MLS# 4818699

Condo
1
1
1,024
2007
$7,122
7/25/20
For Sale
920 Washington Street Extension, Middlebury

920 Washington Street Extension

Middlebury

Price: $399,000

MLS# 4818392

House
2
2
2,354
0.9
1965
$6,441
7/23/20
For Sale
2 Forrest Lane, Middlebury

2 Forrest Lane

Middlebury

Price: $475,000

MLS# 4816526

House
3
4
2,245
0.67
1959
$6,307
7/14/20
For Sale
28 Drew Lane, Middlebury

28 Drew Lane

Middlebury

Price: $179,000

MLS# 4816270

House
3
2
1,728
0.48
1971
$3,573
7/10/20
For Sale
288 Weybridge Street, Middlebury

288 Weybridge Street

Middlebury

Price: $729,000

MLS# 4815801

House
3
3
3,705
0.67
1981
$12,678
7/10/20
For Sale
10 South Street, Middlebury

10 South Street

Middlebury

Price: $499,000

MLS# 4815545

House
3
3
2,187
0.34
1800
$8,581
7/09/20
7/19/20
For Sale with Contract
13 Elm Street, Middlebury

13 Elm Street

Middlebury

Price: $395,000

MLS# 4815056

House
3
3
1,712
0.55
1900
$5,606
7/07/20
For Sale
1892 Munger Street, Middlebury

1892 Munger Street

Middlebury

Price: $775,000

MLS# 4814601

House
4
4
4,524
23.5
2005
$14,855
7/01/20
For Sale
398 East Main Street, Middlebury

398 East Main Street

Middlebury

Price: $229,000

MLS# 4811351

House
2
2
1,338
0.24
1830
$4,984
6/17/20
7/16/20
For Sale with Contract
800 Routh 7 South, Middlebury

800 Routh 7 South

Middlebury

Price: $240,000

MLS# 4810765

House
3
2
2,300
1.7
1965
$5,287
6/13/20
6/20/20
For Sale with Contract
88 Charles Avenue, Middlebury

88 Charles Avenue

Middlebury

Price: $229,000

MLS# 4808397

House
3
1
1,696
0.44
1960
$4,241
5/31/20
6/16/20
For Sale with Contract
4863 Case Street, Middlebury

4863 Case Street

Middlebury

Price: $755,000

MLS# 4802466

House
4
3
3,592
109.2
1840
$11,160
4/24/20
For Sale
48 Court Street, Middlebury

48 Court Street

Middlebury

Price: $239,000

MLS# 4797081

House
3
2
1,548
0.28
1900
NA
3/09/20
7/16/20
For Sale with Contract
51 Seminary Street, Middlebury

51 Seminary Street

Middlebury

Price: $550,000

MLS# 4795324

House
9
3
5,432
6
1820
NA
2/25/20
For Sale
888 Three Mile Bridge Road, Middlebury

888 Three Mile Bridge Road

Middlebury

Price: $549,900

MLS# 4793440

House
4
5
3,726
11.9
1978
$12,171
2/10/20
For Sale
0 Pratt Road, Middlebury

0 Pratt Road

Middlebury

Price: $450,000

MLS# 4784476

Land
rural residential
215
1000 Ft
11/06/19
For Sale
TBD Case Street, Middlebury

TBD Case Street

Middlebury

Price: $40,000

MLS# 4783751

Land
Forest District
19
Ft
10/29/19
For Sale
377 East Main Street, Middlebury

377 East Main Street

Middlebury

Price: $249,500

MLS# 4774386

House
3
2
1,964
1.19
1986
$5,552
9/03/19
7/02/20
For Sale with Contract
14 Maecliff Court, Middlebury

14 Maecliff Court

Middlebury

Price: $59,500

MLS# 4773238

Land
MDR
0.34
40 Ft
8/27/19
For Sale
00 Painter Road Highway, Middlebury

00 Painter Road Highway

Middlebury

Price: $999,000

MLS# 4713068

Land
Ag
100
Ft
8/14/18
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
For Sale
 South Ridge, Middlebury

South Ridge

Middlebury

Price: $195,000

MLS# 4450390

Land
MDR
22.24
575 Ft
9/11/15
For Sale
277 Meadow Glen, Middlebury

277 Meadow Glen

Middlebury

Price: $135,000

MLS# 4450385

Land
MDR
1.97
320 Ft
9/11/15
For Sale
239 Meadow Glen, Middlebury

239 Meadow Glen

Middlebury

Price: $155,000

MLS# 4450384

Land
MDR
2.94
320 Ft
9/11/15
For Sale
376 South Ridge, Middlebury

376 South Ridge

Middlebury

Price: $85,000

MLS# 4450375

Land
MDR
0.6
Ft
9/11/15
For Sale
34 Meadow Glen, Middlebury

34 Meadow Glen

Middlebury

Price: $98,500

MLS# 4450365

Land
MDR
1.28
197 Ft
9/11/15
For Sale
Loading More