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. Learn more about Addison County.

Interested in Selling a Home in Middlebury? Contact Us Today!

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

19 Real Estate Listings and Homes for Sale
4 Wilmar Street, Middlebury

4 Wilmar Street

Middlebury

Price: $150,000

MLS# 5041838

Land
Res
0.52
180 Ft
5/19/25
For Sale
2 Wilmar Street, Middlebury

2 Wilmar Street

Middlebury

Price: $150,000

MLS# 5041836

Land
Res
0.54
177 Ft
5/19/25
For Sale
719 Washington Street Extension, Middlebury

719 Washington Street Extension

Middlebury

Price: $695,000

MLS# 5041770

House
4
3
2,930
3
1880
NA
5/19/25
For Sale
72 Juniper Lane, Middlebury

72 Juniper Lane

Middlebury

Price: $695,000

MLS# 5040906

House
4
3
3,788
2.2
1967
$10,604
5/14/25
For Sale
35 Twin Circles, Middlebury

35 Twin Circles

Middlebury

Price: $350,000

MLS# 5040344

Condo
2
2
1,432
1990
$6,263
5/12/25
For Sale
795 Lower Foote Street, Middlebury

795 Lower Foote Street

Middlebury

Price: $395,000

MLS# 5038931

Multi-Family
2
0
0
2,610
1900
$8,207
5/01/25
5/11/25
For Sale with Contract
795 Lower Foote Street, Middlebury

795 Lower Foote Street

Middlebury

Price: $395,000

MLS# 5038907

House
5
2
1,986
1.42
1900
$8,207
5/01/25
5/20/25
For Sale with Contract
503 Weybridge Street, Middlebury

503 Weybridge Street

Middlebury

Price: $439,000

MLS# 5038795

House
3
1
1,380
0.4
1963
$7,298
5/01/25
5/02/25
For Sale with Contract
810 Lower Foote Street, Middlebury

810 Lower Foote Street

Middlebury

Price: $439,000

MLS# 5038278

House
2
2
1,400
0.55
2005
$7,360
4/28/25
5/21/25
For Sale with Contract
915 Lower Foote Street, Middlebury

915 Lower Foote Street

Middlebury

Price: $469,000

MLS# 5037886

House
3
2
1,584
0.4
1998
$6,340
4/24/25
For Sale
49 South Street, Middlebury

49 South Street

Middlebury

Price: $995,000

MLS# 5036319

House
5
3
2,640
0.57
1920
$11,406
4/15/25
5/08/25
For Sale with Contract
1 East Road, Middlebury

1 East Road

Middlebury

Price: $614,000

MLS# 5036080

House
3
2
1,976
0.34
1980
$5,777
4/13/25
For Sale
91 Old Pasture Lane, Middlebury

91 Old Pasture Lane

Middlebury

Price: $1,355,000

MLS# 5035239

House
6
5
4,503
10.73
1979
$17,232
4/08/25
For Sale
53 Stonecrop Road, Middlebury

53 Stonecrop Road

Middlebury

Price: $430,000

MLS# 5028020

House
3
3
2,019
0
2025
NA
1/29/25
For Sale
60-62 Main Street, Middlebury

60-62 Main Street

Middlebury

Price: $599,000

MLS# 5022266

Multi-Family
3
1
3
4,506
1900
$16,169
11/15/24
For Sale
436 A Middle Road, Middlebury

436 A Middle Road

Middlebury

Price: $375,000

MLS# 5020805

House
3
1
2,442
0.57
1979
NA
11/01/24
For Sale
45 Court St.(Route 7) Street, Middlebury

45 Court St.(Route 7) Street

Middlebury

Price: $697,000

MLS# 4999647

House
5
3
3,120
0.2
1840
$8,172
6/09/24
For Sale
45 Court Street, Middlebury

45 Court Street

Middlebury

Price: $697,000

MLS# 4999633

Multi-Family
3
5
3
3,120
1840
$8,172
6/09/24
For Sale
103 Court Street, Middlebury

103 Court Street

Middlebury

Price: $798,000

MLS# 4980065

House
5
4
4,810
2.4
1995
$11,308
12/12/23
For Sale
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