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.

21 Real Estate Listings and Homes for Sale
12 Overbrook Drive, Middlebury

12 Overbrook Drive

Middlebury

Price: $425,000

MLS# 5001554

Condo
3
2
1,875
1988
$6,416
6/20/24
For Sale
2225 7 South Route, Middlebury

2225 7 South Route

Middlebury

Price: $625,000

MLS# 5001576

House
4
2
2,584
0.89
1930
$7,260
6/18/24
For Sale
436 Middle Road, Middlebury

436 Middle Road

Middlebury

Price: $249,000

MLS# 5000861

House
3
2
1,476
0.92
1940
NA
6/17/24
For Sale
11 Willard Street, Middlebury

11 Willard Street

Middlebury

Price: $239,000

MLS# 5000742

House
3
2
1,526
0.09
1850
$4,200
6/15/24
For Sale
45 Court St.(Route 7) Street, Middlebury

45 Court St.(Route 7) Street

Middlebury

Price: $725,000

MLS# 4999647

House
6
3
3,120
0.2
1840
$7,039
6/09/24
6/17/24
For Sale with Contract
45 Court Street, Middlebury

45 Court Street

Middlebury

Price: $725,000

MLS# 4999633

Multi-Family
3
4
3
3,120
1840
$7,039
6/09/24
6/17/24
For Sale with Contract
5 Case Street, Middlebury

5 Case Street

Middlebury

Price: $315,000

MLS# 4998734

House
3
1
1,144
0.48
1967
$4,758
6/04/24
6/11/24
For Sale with Contract
152 Maple Street, Middlebury

152 Maple Street

Middlebury

Price: $429,000

MLS# 5000162

Condo
0
1
1,500
1990
$3,472
5/29/24
For Sale
276 Monroe Street, Middlebury

276 Monroe Street

Middlebury

Price: $378,500

MLS# 4997757

House
3
2
1,704
0.22
1980
$6,570
5/28/24
6/10/24
For Sale with Contract
111 South Main Street, Middlebury

111 South Main Street

Middlebury

Price: $1,200,000

MLS# 4997190

Multi-Family
6
9
7
5,497
1873
$10,852
5/24/24
6/04/24
For Sale with Contract
12 East Road, Middlebury

12 East Road

Middlebury

Price: $299,000

MLS# 4996467

Condo
2
1
864
1981
$3,887
5/20/24
For Sale
235 Rogers Road, Middlebury

235 Rogers Road

Middlebury

Price: $415,000

MLS# 4996002

House
3
1
1,120
0.29
1979
$5,813
5/16/24
For Sale
9 Woodbridge Lane, Middlebury

9 Woodbridge Lane

Middlebury

Price: $215,000

MLS# 4995769

Condo
2
2
1,080
1981
$3,252
5/15/24
5/29/24
For Sale with Contract
442 East Main Street, Middlebury

442 East Main Street

Middlebury

Price: $419,000

MLS# 4994716

House
4
2
1,815
0.26
1870
$5,407
5/08/24
5/12/24
For Sale with Contract
2776 Case Street, Middlebury

2776 Case Street

Middlebury

Price: $434,900

MLS# 4993787

House
2
1
1,128
0.93
1950
$4,949
5/02/24
For Sale
74 Court Street, Middlebury

74 Court Street

Middlebury

Price: $675,000

MLS# 4989606

Multi-Family
4
6
4
1,440
1920
$8,981
3/29/24
For Sale
76 Court Street, Middlebury

76 Court Street

Middlebury

Price: $799,000

MLS# 4988342

House
2
3
4,607
0.55
1928
$13,703
3/18/24
4/16/24
For Sale with Contract
3210 Case Street, Middlebury

3210 Case Street

Middlebury

Price: $520,000

MLS# 4987283

House
3
3
2,656
1
1977
$6,194
3/07/24
For Sale
118 Three Mile Bridge Road, Middlebury

118 Three Mile Bridge Road

Middlebury

Price: $420,000

MLS# 4985673

House
3
2
2,232
1.1
1820
$4,761
2/21/24
For Sale
103 Court Street, Middlebury

103 Court Street

Middlebury

Price: $990,000

MLS# 4980065

House
5
4
4,810
2.4
1995
$11,308
12/12/23
For Sale
79 Court Street, Middlebury

79 Court Street

Middlebury

Price: $450,000

MLS# 4979907

House
2
3
2,485
0.31
1890
$7,045
12/11/23
For Sale
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