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.

41 Currently Available
88 Charles Avenue, Middlebury

88 Charles Avenue

Middlebury

Price: $235,000

MLS# 4808397

House
3
1
1,696
0.44
1960
$4,241
5/31/20
For Sale
68 North Pleasant Street, Middlebury

68 North Pleasant Street

Middlebury

Price: $199,900

MLS# 4807770

House
4
2
1,440
0.33
1900
$4,557
5/29/20
For Sale
99 Creek Road, Middlebury

99 Creek Road

Middlebury

Price: $134,900

MLS# 4804586

House
3
1
1,064
0.33
1967
$4,232
5/06/20
For Sale
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
200 Butternut Ridge Drive, Middlebury

200 Butternut Ridge Drive

Middlebury

Price: $79,000

MLS# 4802098

Land
Residential
0.4
Ft
4/22/20
5/22/20
For Sale with Contract
12 Seminary Street, Middlebury

12 Seminary Street

Middlebury

Price: $475,000

MLS# 4801600

House
3
2
1,650
0.11
1793
$7,550
4/17/20
For Sale
1136 Lower Foote Street, Middlebury

1136 Lower Foote Street

Middlebury

Price: $259,900

MLS# 4798246

House
2
2
3,280
1.5
1986
$6,497
3/16/20
5/12/20
For Sale with Contract
48 Court Street, Middlebury

48 Court Street

Middlebury

Price: $249,000

MLS# 4797081

House
3
2
1,548
0.28
1900
NA
3/09/20
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
211 Creek Road, Middlebury

211 Creek Road

Middlebury

Price: $279,500

MLS# 4795297

House
3
2
1,488
0.29
2010
$5,783
2/25/20
For Sale
46 Ossie Road, Middlebury

46 Ossie Road

Middlebury

Price: $103,000

MLS# 4795292

House
3
2
1,694
0.3
1957
$4,652
2/25/20
For Sale
81 Court Street, Middlebury

81 Court Street

Middlebury

Price: $199,000

MLS# 4794331

House
3
1
1,105
0.22
1900
$4,659
2/17/20
5/29/20
For Sale with Contract
33 Twin Circle, Middlebury

33 Twin Circle

Middlebury

Price: $222,000

MLS# 4794312

Condo
2
2
1,412
1990
$5,013
2/17/20
For Sale
337 Burnham Drive, Middlebury

337 Burnham Drive

Middlebury

Price: $259,000

MLS# 4793558

House
3
2
2,184
1.15
1985
$6,277
2/11/20
3/18/20
For Sale with Contract
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
250 Halladay Road, Middlebury

250 Halladay Road

Middlebury

Price: $138,900

MLS# 4784184

House
3
2
1,161
1.6
1962
$5,381
11/04/19
For Sale
4 Little Pond Road, Middlebury

4 Little Pond Road

Middlebury

Price: $449,000

MLS# 4784137

Condo
2
3
1,516
1989
$8,473
11/04/19
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
1890 North Branch Road, Middlebury

1890 North Branch Road

Middlebury

Price: $435,000

MLS# 4777370

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

36 Seymour Street

Middlebury

Price: $244,000

MLS# 4776797

Multi-Family
2
6
2
2,048
1875
$4,819
9/16/19
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
5/14/20
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
17 Forest Ridge, Middlebury

17 Forest Ridge

Middlebury

Price: $215,000

MLS# 4769949

House
2
2
1,844
2.21
1986
$5,427
8/09/19
4/21/20
For Sale with Contract
46 Washington Street, Middlebury

46 Washington Street

Middlebury

Price: $280,000

MLS# 4769200

House
3
2
1,890
0.31
1840
$7,529
8/05/19
For Sale
62 Otterside Court, Middlebury

62 Otterside Court

Middlebury

Price: $169,900

MLS# 4763648

Condo
2
2
1,420
1974
$3,478
7/08/19
For Sale
Page 2
1917 Case Street, Middlebury

1917 Case Street

Middlebury

Price: $314,900

MLS# 4758985

House
3
3
1,719
0.64
1968
$5,626
6/17/19
For Sale
3408 Case Street, Middlebury

3408 Case Street

Middlebury

Price: $127,000

MLS# 4754694

Land
AR/FOR
45.02
60 Ft
5/29/19
For Sale
153 Wildflower Lane, Middlebury

153 Wildflower Lane

Middlebury

Price: $550,000

MLS# 4723868

House
4
4
4,671
4.48
1984
$12,653
10/16/18
For Sale
00 Painter Road Highway, Middlebury

00 Painter Road Highway

Middlebury

Price: $1,250,000

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
 South Ridge, Middlebury

South Ridge

Middlebury

Price: $155,000

MLS# 4450389

Land
MDR
4.9
140 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
411 South Ridge, Middlebury

411 South Ridge

Middlebury

Price: $105,000

MLS# 4450379

Land
MDR
1.01
125 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
234 South Ridge, Middlebury

234 South Ridge

Middlebury

Price: $95,000

MLS# 4450362

Land
MDR
0.78
87 Ft
9/11/15
For Sale
192 South Ridge, Middlebury

192 South Ridge

Middlebury

Price: $95,000

MLS# 4450361

Land
MDR
0.88
120 Ft
9/11/15
For Sale
92 South Ridge, Middlebury

92 South Ridge

Middlebury

Price: $95,000

MLS# 4313244

Land
MDR
0.52
121 Ft
9/03/13
For Sale
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