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.

35 Currently Available
30 Pinewood Road, Middlebury

30 Pinewood Road

Middlebury

Price: $158,500

MLS# 4830742

Condo
2
1
1,122
1988
$2,713
9/25/20
For Sale
142 May Apple Lane, Middlebury

142 May Apple Lane

Middlebury

Price: $498,000

MLS# 4828112

House
4
3
2,950
0.88
2005
$12,229
9/11/20
For Sale
107 Butternut Ridge Drive, Middlebury

107 Butternut Ridge Drive

Middlebury

Price: $425,000

MLS# 4827984

House
5
3
3,743
4.13
1969
$8,254
9/10/20
9/15/20
For Sale with Contract
35 Lower Plains Road, Middlebury

35 Lower Plains Road

Middlebury

Price: $275,000

MLS# 4827147

House
4
2
1,694
0.3
1920
$5,374
9/05/20
For Sale
3420 Case Street, Middlebury

3420 Case Street

Middlebury

Price: $95,000

MLS# 4827709

Land
Ag/Rural & Forest
45.02
58 Ft
9/04/20
For Sale
8 Nedde Lane, Middlebury

8 Nedde Lane

Middlebury

Price: $499,000

MLS# 4826595

Condo
3
4
2,358
1989
$10,443
9/03/20
For Sale
56 Court Street, Middlebury

56 Court Street

Middlebury

Price: $565,000

MLS# 4825854

Multi-Family
3
6
3
3,438
1870
$8,158
8/31/20
9/04/20
For Sale with Contract
381 East Main Street, Middlebury

381 East Main Street

Middlebury

Price: $199,500

MLS# 4826210

House
3
1
1,482
0.26
1940
$4,000
8/30/20
9/17/20
For Sale with Contract
127 Oak Drive, Middlebury

127 Oak Drive

Middlebury

Price: $397,000

MLS# 4825498

House
3
3
2,522
1.31
1987
$8,632
8/28/20
For Sale
00 Munger Street, Middlebury

00 Munger Street

Middlebury

Price: $350,000

MLS# 4824651

Land
AR
29
1628 Ft
8/25/20
For Sale
50 Short Shannon Street, Middlebury

50 Short Shannon Street

Middlebury

Price: $335,000

MLS# 4824541

House
3
2
1,548
0.2
1951
$6,167
8/24/20
8/30/20
For Sale with Contract
516 Weybridge Street, Middlebury

516 Weybridge Street

Middlebury

Price: $389,000

MLS# 4824368

House
4
3
2,048
0.39
1900
$7,843
8/24/20
9/21/20
For Sale with Contract
8 Kings Row Road, Middlebury

8 Kings Row Road

Middlebury

Price: $249,900

MLS# 4824164

House
3
1
1,428
0.34
1950
$5,608
8/21/20
For Sale
21 Lower Plains Road, Middlebury

21 Lower Plains Road

Middlebury

Price: $225,000

MLS# 4823419

House
3
1
1,896
1.4
1900
$4,149
8/18/20
For Sale
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
998 Quarry Road, Middlebury

998 Quarry Road

Middlebury

Price: $225,000

MLS# 4822188

House
3
1
1,290
0.87
1850
$4,189
8/12/20
8/22/20
For Sale with Contract
54 Otterside Court, Middlebury

54 Otterside Court

Middlebury

Price: $169,900

MLS# 4821458

Condo
2
2
1,272
1974
$3,677
8/08/20
8/22/20
For Sale with Contract
2399 Route 7 Highway, Middlebury

2399 Route 7 Highway

Middlebury

Price: $145,000

MLS# 4821352

House
2
1
868
0.19
1940
$2,862
8/07/20
8/12/20
For Sale with Contract
100 Birch Drive, Middlebury

100 Birch Drive

Middlebury

Price: $425,000

MLS# 4821127

House
4
3
2,352
3
1996
$7,356
8/04/20
8/31/20
For Sale with Contract
70 Maple Street, Middlebury

70 Maple Street

Middlebury

Price: $349,000

MLS# 4818699

Condo
1
1
1,024
2007
$7,122
7/25/20
8/24/20
For Sale with Contract
920 Washington Street Extension, Middlebury

920 Washington Street Extension

Middlebury

Price: $385,000

MLS# 4818392

House
2
2
2,354
0.9
1965
$6,441
7/23/20
9/13/20
For Sale with Contract
2 Forrest Lane, Middlebury

2 Forrest Lane

Middlebury

Price: $400,000

MLS# 4816526

House
3
4
2,245
0.67
1959
$6,307
7/14/20
9/18/20
For Sale with Contract
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
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
4863 Case Street, Middlebury

4863 Case Street

Middlebury

Price: $699,000

MLS# 4802466

House
4
3
3,592
109.2
1840
$11,160
4/24/20
For Sale
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
Page 2
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
14 Maecliff Court, Middlebury

14 Maecliff Court

Middlebury

Price: $57,500

MLS# 4773238

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

00 Painter Road Highway

Middlebury

Price: $899,000

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
277 Meadow Glen, Middlebury

277 Meadow Glen

Middlebury

Price: $135,000

MLS# 4450385

Land
MDR
1.97
320 Ft
9/11/15
8/06/20
For Sale with Contract
376 South Ridge, Middlebury

376 South Ridge

Middlebury

Price: $85,000

MLS# 4450375

Land
MDR
0.6
Ft
9/11/15
For Sale
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