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.

 

49 Currently Available
51 Seminary Street, Middlebury

51 Seminary Street

Middlebury

Price: $550,000

MLS# 4795324

House
9
3
5,432
6
1820
NA
2/25/2020
211 Creek Road, Middlebury

211 Creek Road

Middlebury

Price: $297,900

MLS# 4795297

House
3
2
1,488
0.29
2010
$5,783
2/25/2020
46 Ossie Road, Middlebury

46 Ossie Road

Middlebury

Price: $146,500

MLS# 4795292

House
3
2
1,694
0.3
1957
$4,652
2/25/2020
781 Burnham Drive, Middlebury

781 Burnham Drive

Middlebury

Price: $495,000

MLS# 4795046

House
4
4
2,904
11.63
1981
$10,675
2/23/2020
72 Ossie Road, Middlebury

72 Ossie Road

Middlebury

Price: $199,700

MLS# 4794935

House
3
2
1,440
0.22
1930
$4,009
2/21/2020
70 Maple Street, Middlebury

70 Maple Street

Middlebury

Price: $485,000

MLS# 4794839

Condo
2
3
1,603
2006
$10,635
2/21/2020
1 Harrow Way, Middlebury

1 Harrow Way

Middlebury

Price: $299,900

MLS# 4794588

House
3
2
1,672
0.4
1978
$7,150
2/19/2020
81 Court Street, Middlebury

81 Court Street

Middlebury

Price: $210,000

MLS# 4794331

House
3
1
1,105
0.22
1900
$4,659
2/17/2020
33 Twin Circle, Middlebury

33 Twin Circle

Middlebury

Price: $227,000

MLS# 4794312

Condo
2
2
1,412
1990
$5,013
2/17/2020
95 Seymour Street, Middlebury

95 Seymour Street

Middlebury

Price: $289,900

MLS# 4794224

House
3
2
1,715
1.5
1800
$6,256
2/17/2020
337 Burnham Drive, Middlebury

337 Burnham Drive

Middlebury

Price: $259,000

MLS# 4793558

House
3
2
2,184
1.15
1985
$6,277
2/11/2020
26 South Street, Middlebury

26 South Street

Middlebury

Price: $430,000

MLS# 4793466

House
4
3
2,152
0.4
1905
$8,037
2/11/2020
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
2/10/2020
32 Morningside Drive, Middlebury

32 Morningside Drive

Middlebury

Price: $625,000

MLS# 4792055

House
4
5
4,616
0.44
1944
$13,544
1/30/2020
20 Stonegate Drive, Middlebury

20 Stonegate Drive

Middlebury

Price: $204,000

MLS# 4788327

House
3
1
1,288
0.35
1967
$5,346
12/18/2019
75 Court Street, Middlebury

75 Court Street

Middlebury

Price: $229,900

MLS# 4786718

Multi-Family
2
4
3
2,000
1973
$5,243
11/26/2019
0 Pratt Road, Middlebury

0 Pratt Road

Middlebury

Price: $450,000

MLS# 4784476

Land
rural residential
215
1000 Ft
11/06/2019
250 Halladay Road, Middlebury

250 Halladay Road

Middlebury

Price: $157,500

MLS# 4784184

House
3
2
1,161
1.6
1962
$5,381
11/04/2019
4 Little Pond Road, Middlebury

4 Little Pond Road

Middlebury

Price: $475,000

MLS# 4784137

Condo
2
3
1,516
1989
$8,473
11/04/2019
TBD Case Street, Middlebury

TBD Case Street

Middlebury

Price: $40,000

MLS# 4783751

Land
Forest District
19
Ft
10/29/2019
55 Monroe Street, Middlebury

55 Monroe Street

Middlebury

Price: $329,000

MLS# 4781077

House
2
1
1,264
0.17
2005
$5,496
10/11/2019
1890 North Branch Road, Middlebury

1890 North Branch Road

Middlebury

Price: $450,000

MLS# 4777370

House
3
3
2,112
5.16
2000
$8,361
9/19/2019
36 Seymour Street, Middlebury

36 Seymour Street

Middlebury

Price: $244,000

MLS# 4776797

Multi-Family
2
6
2
2,048
1875
$4,819
9/16/2019
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
9/03/2019
14 Maecliff Court, Middlebury

14 Maecliff Court

Middlebury

Price: $59,500

MLS# 4773238

Land
MDR
0.34
40 Ft
8/27/2019
Page 2
209 Happy Valley Road, Middlebury

209 Happy Valley Road

Middlebury

Price: $199,000

MLS# 4771305

House
4
3
2,632
0.61
2000
$6,457
8/16/2019
17 Forest Ridge, Middlebury

17 Forest Ridge

Middlebury

Price: $215,000

MLS# 4769949

House
2
2
1,844
2.21
1986
$5,427
8/09/2019
46 Washington Street, Middlebury

46 Washington Street

Middlebury

Price: $280,000

MLS# 4769200

House
3
2
1,890
0.31
1840
$7,529
8/05/2019
62 Otterside Court, Middlebury

62 Otterside Court

Middlebury

Price: $179,900

MLS# 4763648

Condo
2
2
1,420
1974
$3,478
7/08/2019
1917 Case Street, Middlebury

1917 Case Street

Middlebury

Price: $314,900

MLS# 4758985

House
3
3
1,719
0.64
1968
$5,626
6/17/2019
1138 Case Street, Middlebury

1138 Case Street

Middlebury

Price: $199,900

MLS# 4755762

House
3
1
1,248
0.49
1966
$4,611
6/03/2019
3408 Case Street, Middlebury

3408 Case Street

Middlebury

Price: $127,000

MLS# 4754694

Land
AR/FOR
45.02
60 Ft
5/29/2019
49 Seymour Street, Middlebury

49 Seymour Street

Middlebury

Price: $169,500

MLS# 4752489

Multi-Family
2
4
3
2,169
1860
$4,379
5/17/2019
153 Wildflower Lane, Middlebury

153 Wildflower Lane

Middlebury

Price: $575,000

MLS# 4723868

House
4
4
4,671
4.48
1984
$12,653
10/16/2018
0 Route 7 Route, Middlebury

0 Route 7 Route

Middlebury

Price: $249,000

MLS# 4719512

Land
Multiple
178
Ft
9/20/2018
00 Painter Road Highway, Middlebury

00 Painter Road Highway

Middlebury

Price: $1,600,000

MLS# 4713068

Land
Ag
100
Ft
8/14/2018
TBD Route 7 South, Middlebury

TBD Route 7 South

Middlebury

Price: $350,000

MLS# 4639868

Land
AR
111.3
670 Ft
6/09/2017
 South Ridge, Middlebury

South Ridge

Middlebury

Price: $195,000

MLS# 4450390

Land
MDR
22.24
575 Ft
9/11/2015
 South Ridge, Middlebury

South Ridge

Middlebury

Price: $155,000

MLS# 4450389

Land
MDR
4.9
140 Ft
9/11/2015
277 Meadow Glen, Middlebury

277 Meadow Glen

Middlebury

Price: $135,000

MLS# 4450385

Land
MDR
1.97
320 Ft
9/11/2015
239 Meadow Glen, Middlebury

239 Meadow Glen

Middlebury

Price: $155,000

MLS# 4450384

Land
MDR
2.94
320 Ft
9/11/2015
411 South Ridge, Middlebury

411 South Ridge

Middlebury

Price: $105,000

MLS# 4450379

Land
MDR
1.01
125 Ft
9/11/2015
376 South Ridge, Middlebury

376 South Ridge

Middlebury

Price: $85,000

MLS# 4450375

Land
MDR
0.6
Ft
9/11/2015
34 Meadow Glen, Middlebury

34 Meadow Glen

Middlebury

Price: $98,500

MLS# 4450365

Land
MDR
1.28
197 Ft
9/11/2015
234 South Ridge, Middlebury

234 South Ridge

Middlebury

Price: $95,000

MLS# 4450362

Land
MDR
0.78
87 Ft
9/11/2015
192 South Ridge, Middlebury

192 South Ridge

Middlebury

Price: $95,000

MLS# 4450361

Land
MDR
0.88
120 Ft
9/11/2015
92 South Ridge, Middlebury

92 South Ridge

Middlebury

Price: $95,000

MLS# 4313244

Land
MDR
0.52
121 Ft
9/03/2013
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