Middlebury VT Real Estate & Homes for Sale

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.

31 Real Estate Listings and Homes for Sale

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1844 Halladay Road, Middlebury

1844 Halladay Road

Price: $1,100,000

MLS# 5091765

House Type

4 Beds

5 Baths

2,804 Sqft

12 Acres

1867 Built

$11,745 Taxes

5/29/26 List Date

Status: For Sale

21 Seminary Street, Middlebury

21 Seminary Street

Price: $549,000

MLS# 5091320

House Type

5 Beds

5 Baths

3,630 Sqft

0.22 Acres

1813 Built

$8,977 Taxes

5/28/26 List Date

Status: For Sale

95 Seminary Street Extension, Middlebury

95 Seminary Street Extension

Price: $489,000

MLS# 5090864

House Type

3 Beds

2 Baths

1,916 Sqft

1.1 Acres

1973 Built

$84,765 Taxes

5/25/26 List Date

Status: For Sale

2801 Route 7 South, Middlebury

2801 Route 7 South

Price: $549,000

MLS# 5090473

House Type

3 Beds

2 Baths

1,976 Sqft

0.5 Acres

1955 Built

$2,473 Taxes

5/22/26 List Date

Status: For Sale

2337 VT Route 7, Middlebury

2337 VT Route 7

Price: $549,000

MLS# 5089982

Multi-Family Type

3 Units

2 Beds

3 Baths

1,960 Sqft

1900 Built

$6,616 Taxes

5/20/26 List Date

Status: For Sale

29 Kings Row, Middlebury

29 Kings Row

Price: $679,000

MLS# 5088782

House Type

5 Beds

5 Baths

4,840 Sqft

1.73 Acres

2003 Built

$10,688 Taxes

5/13/26 List Date

Status: For Sale

41 Barnes Brook Road, Middlebury

41 Barnes Brook Road, 9.2

Price: $388,900

MLS# 5088391

House Type

2 Beds

2 Baths

1,516 Sqft

0 Acres

2026 Built

NA Taxes

5/12/26 List Date

5/12/26 Contract Date

Status: For Sale with Contract

31 Evergreen Lane, Middlebury

31 Evergreen Lane

Price: $370,000

MLS# 5087754

Condo Type

2 Beds

2 Baths

1,397 Sqft

1984 Built

$5,006 Taxes

5/08/26 List Date

Status: For Sale

442 East Main Street, Middlebury

442 East Main Street

Price: $439,000

MLS# 5086871

House Type

4 Beds

2 Baths

1,815 Sqft

0.26 Acres

1870 Built

$6,284 Taxes

5/04/26 List Date

Status: For Sale

30 Barnes Brook Road, Middlebury

30 Barnes Brook Road, 10.4

Price: $765,000

MLS# 5085570

House Type

3 Beds

3 Baths

1,938 Sqft

0 Acres

2026 Built

NA Taxes

4/27/26 List Date

4/27/26 Contract Date

Status: For Sale with Contract

7 Evergreen Lane, Middlebury

7 Evergreen Lane

Price: $275,000

MLS# 5084987

Condo Type

2 Beds

2 Baths

1,440 Sqft

1981 Built

$5,212 Taxes

4/23/26 List Date

Status: For Sale

2 Wilmar Street, Middlebury

2 Wilmar Street

Price: $150,000

MLS# 5084490

Land Type

Residential 2 (R-2) Zoning

0.54 Acres

303 Ft Road Frontage

4/20/26 List Date

Status: For Sale

4 Wilmar Road, Middlebury

4 Wilmar Road

Price: $150,000

MLS# 5084486

Land Type

Residential 2 (R-2) Zoning

0.52 Acres

180 Ft Road Frontage

4/20/26 List Date

Status: For Sale

110 Sarahs Way, Middlebury

110 Sarahs Way

Price: $435,000

MLS# 5083167

House Type

4 Beds

2 Baths

2,032 Sqft

0.48 Acres

2005 Built

$6,551 Taxes

4/11/26 List Date

5/23/26 Contract Date

Status: For Sale with Contract

78 Brush Lane, Middlebury

78 Brush Lane, 10.6

Price: $765,000

MLS# 5080963

House Type

3 Beds

3 Baths

1,938 Sqft

0 Acres

2026 Built

NA Taxes

3/26/26 List Date

Status: For Sale

74 Brush Lane, Middlebury

74 Brush Lane, 10.5

Price: $540,000

MLS# 5080959

House Type

3 Beds

3 Baths

1,938 Sqft

0 Acres

2026 Built

NA Taxes

3/26/26 List Date

Status: For Sale

33 Barnes Brook Road, Middlebury

33 Barnes Brook Road

Price: $430,000

MLS# 5079672

House Type

2 Beds

2 Baths

1,516 Sqft

0 Acres

2026 Built

NA Taxes

3/17/26 List Date

3/17/26 Contract Date

Status: For Sale with Contract

35 Ossie Road, Middlebury

35 Ossie Road

Price: $479,000

MLS# 5075441

House Type

3 Beds

2 Baths

2,213 Sqft

1.2 Acres

1969 Built

$5,497 Taxes

2/02/26 List Date

Status: For Sale

8 Fred Johnson Circle, Middlebury

8 Fred Johnson Circle

Price: $149,000

MLS# 5072452

Land Type

MDR Zoning

4.5 Acres

150 Ft Road Frontage

12/19/25 List Date

Status: For Sale

6 Fred Johnson Circle, Middlebury

6 Fred Johnson Circle

Price: $154,000

MLS# 5072450

Land Type

MDR Zoning

4 Acres

150 Ft Road Frontage

12/19/25 List Date

Status: For Sale

20 Forest Ridge Drive, Middlebury

20 Forest Ridge Drive

Price: $185,000

MLS# 5072447

Land Type

MDR Zoning

3.54 Acres

250 Ft Road Frontage

12/19/25 List Date

Status: For Sale

29 Barnes Brook Road, Middlebury

29 Barnes Brook Road, 9.6

Price: $482,500

MLS# 5072389

House Type

3 Beds

3 Baths

2,019 Sqft

0 Acres

2026 Built

NA Taxes

12/19/25 List Date

12/19/25 Contract Date

Status: For Sale with Contract

TBD Route 7 S, Middlebury

TBD Route 7 S

Price: $220,000

MLS# 5070675

Land Type

AR Zoning

9.8 Acres

780 Ft Road Frontage

11/25/25 List Date

Status: For Sale

376 South Ridge Drive, Middlebury

376 South Ridge Drive

Price: $199,000

MLS# 5068284

Land Type

R2 Zoning

0.6 Acres

Ft Road Frontage

11/03/25 List Date

Status: For Sale

30 South Street, Middlebury

30 South Street

Price: $549,000

MLS# 5064171

House Type

4 Beds

2 Baths

2,037 Sqft

0.21 Acres

1822 Built

$7,924 Taxes

10/03/25 List Date

Status: For Sale

47 Barnes Brook Road, Middlebury

47 Barnes Brook Road

Price: $482,500

MLS# 5060138

House Type

3 Beds

3 Baths

2,019 Sqft

0 Acres

2026 Built

NA Taxes

9/07/25 List Date

9/07/25 Contract Date

Status: For Sale with Contract

54 Brush Lane, Middlebury

54 Brush Lane, 8.4B

Price: $455,000

MLS# 5060117

Condo Type

3 Beds

2 Baths

1,660 Sqft

2026 Built

NA Taxes

9/07/25 List Date

5/19/26 Contract Date

Status: For Sale with Contract

Page 2▲

40 Brush Lane, Middlebury

40 Brush Lane, 8.3B

Price: $699,500

MLS# 5058429

Condo Type

3 Beds

2 Baths

1,660 Sqft

2026 Built

NA Taxes

8/27/25 List Date

Status: For Sale

35 Barnes Brook Road, Middlebury

35 Barnes Brook Road, 9.4

Price: $388,900

MLS# 5055963

House Type

2 Beds

2 Baths

1,516 Sqft

0 Acres

2026 Built

NA Taxes

8/11/25 List Date

Status: For Sale

39 Barnes Brook Road, Middlebury

39 Barnes Brook Road, 9.3

Price: $585,000

MLS# 5055964

House Type

2 Beds

2 Baths

1,516 Sqft

0 Acres

2026 Built

NA Taxes

8/09/25 List Date

Status: For Sale

103 Court Street, Middlebury

103 Court Street

Price: $570,000

MLS# 5052780

House Type

5 Beds

4 Baths

3,160 Sqft

2.4 Acres

1995 Built

$12,533 Taxes

7/22/25 List Date

6/01/26 Contract Date

Status: For Sale with Contract

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