Middlebury Vermont Homes for Sale

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17 Twin Circle Middlebury, VT MLS# 5071045 - Image 1

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 2

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 3

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 4

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 5

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 6

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 7

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 8

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 9

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 10

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 11

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 12

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 13

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 14

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 15

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 16

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 17

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 18

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 19

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 20

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 21

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 22

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 23

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 24

17 Twin Circle Middlebury, VT MLS# 5071045 - Image 25

1 of 25

$385,000

Beds

2.1

Baths

1,894

Sq.Ft.

17 Twin Circle

Middlebury, VT

Courtesy of CHAMPLAIN VALLEY PROPERTIES

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 1

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 2

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 3

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 4

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 5

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 6

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 7

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 8

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 9

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 10

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 11

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 12

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 13

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 14

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 15

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 16

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 17

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 18

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 19

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 20

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 21

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 22

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 23

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 24

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 25

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 26

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 27

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 28

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 29

44 Lower Plains Road Middlebury, VT MLS# 5065257 - Image 30

1 of 30

$349,900

Beds

3.0

Baths

2,415

Sq.Ft.

44 Lower Plains Road

Middlebury, VT

Courtesy of COLDWELL BANKER HICKOK AND BOARDMAN

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 1

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 2

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 3

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 4

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 5

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 6

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 7

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 8

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 9

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 10

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 11

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 12

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 13

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 14

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 15

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 16

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 17

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 18

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 19

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 20

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 21

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 22

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 23

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 24

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 25

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 26

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 27

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 28

12 Stonegate Drive Middlebury, VT MLS# 5072835 - Image 29

1 of 29

$319,000

Beds

1.0

Baths

1,040

Sq.Ft.

12 Stonegate Drive

Middlebury, VT

Courtesy of RE/MAX NORTH PROFESSIONALS

THE TIME TO SELL IS NOW!

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 1

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 2

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 3

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 4

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 5

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 6

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 7

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 8

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 9

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 10

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 11

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 12

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 13

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 14

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 15

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 16

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 17

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 18

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 19

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 20

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 21

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 22

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 23

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 24

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 25

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 26

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 27

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 28

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 29

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 30

82 Ossie Road Middlebury, VT MLS# 5068676 - Image 31

Virtual Tour

1 of 31

$315,000

Beds

1.1

Baths

1,330

Sq.Ft.

82 Ossie Road

Middlebury, VT

Courtesy of THE REAL ESTATE COMPANY OF VERMONT, LLC

53 High Street Middlebury, VT MLS# 5045832 - Image 1

53 High Street Middlebury, VT MLS# 5045832 - Image 2

53 High Street Middlebury, VT MLS# 5045832 - Image 3

53 High Street Middlebury, VT MLS# 5045832 - Image 4

53 High Street Middlebury, VT MLS# 5045832 - Image 5

53 High Street Middlebury, VT MLS# 5045832 - Image 6

53 High Street Middlebury, VT MLS# 5045832 - Image 7

53 High Street Middlebury, VT MLS# 5045832 - Image 8

53 High Street Middlebury, VT MLS# 5045832 - Image 9

53 High Street Middlebury, VT MLS# 5045832 - Image 10

53 High Street Middlebury, VT MLS# 5045832 - Image 11

53 High Street Middlebury, VT MLS# 5045832 - Image 12

53 High Street Middlebury, VT MLS# 5045832 - Image 13

53 High Street Middlebury, VT MLS# 5045832 - Image 14

53 High Street Middlebury, VT MLS# 5045832 - Image 15

53 High Street Middlebury, VT MLS# 5045832 - Image 16

53 High Street Middlebury, VT MLS# 5045832 - Image 17

53 High Street Middlebury, VT MLS# 5045832 - Image 18

53 High Street Middlebury, VT MLS# 5045832 - Image 19

53 High Street Middlebury, VT MLS# 5045832 - Image 20

53 High Street Middlebury, VT MLS# 5045832 - Image 21

53 High Street Middlebury, VT MLS# 5045832 - Image 22

53 High Street Middlebury, VT MLS# 5045832 - Image 23

53 High Street Middlebury, VT MLS# 5045832 - Image 24

53 High Street Middlebury, VT MLS# 5045832 - Image 25

53 High Street Middlebury, VT MLS# 5045832 - Image 26

53 High Street Middlebury, VT MLS# 5045832 - Image 27

53 High Street Middlebury, VT MLS# 5045832 - Image 28

53 High Street Middlebury, VT MLS# 5045832 - Image 29

53 High Street Middlebury, VT MLS# 5045832 - Image 30

53 High Street Middlebury, VT MLS# 5045832 - Image 31

53 High Street Middlebury, VT MLS# 5045832 - Image 32

53 High Street Middlebury, VT MLS# 5045832 - Image 33

53 High Street Middlebury, VT MLS# 5045832 - Image 34

53 High Street Middlebury, VT MLS# 5045832 - Image 35

53 High Street Middlebury, VT MLS# 5045832 - Image 36

53 High Street Middlebury, VT MLS# 5045832 - Image 37

53 High Street Middlebury, VT MLS# 5045832 - Image 38

1 of 38

$275,000

Beds

3.0

Baths

1,740

Sq.Ft.

53 High Street

Middlebury, VT

Courtesy of RE/MAX NORTH PROFESSIONALS, MIDDLEBURY

TBD Route 7 S Middlebury, VT MLS# 5070675 - Image 1

TBD Route 7 S Middlebury, VT MLS# 5070675 - Image 2

TBD Route 7 S Middlebury, VT MLS# 5070675 - Image 3

TBD Route 7 S Middlebury, VT MLS# 5070675 - Image 4

TBD Route 7 S Middlebury, VT MLS# 5070675 - Image 5

TBD Route 7 S Middlebury, VT MLS# 5070675 - Image 6

TBD Route 7 S Middlebury, VT MLS# 5070675 - Image 7

TBD Route 7 S Middlebury, VT MLS# 5070675 - Image 8

TBD Route 7 S Middlebury, VT MLS# 5070675 - Image 9

TBD Route 7 S Middlebury, VT MLS# 5070675 - Image 10

TBD Route 7 S Middlebury, VT MLS# 5070675 - Image 11

TBD Route 7 S Middlebury, VT MLS# 5070675 - Image 12

TBD Route 7 S Middlebury, VT MLS# 5070675 - Image 13

TBD Route 7 S Middlebury, VT MLS# 5070675 - Image 14

1 of 14

$220,000

Studio

Beds

0.0

Baths

TBD Route 7 S

Middlebury, VT

Courtesy of IPJ REAL ESTATE

376 South Ridge Drive # 31 Middlebury, VT MLS# 5068284 - Image 1

376 South Ridge Drive # 31 Middlebury, VT MLS# 5068284 - Image 2

376 South Ridge Drive # 31 Middlebury, VT MLS# 5068284 - Image 3

376 South Ridge Drive # 31 Middlebury, VT MLS# 5068284 - Image 4

376 South Ridge Drive # 31 Middlebury, VT MLS# 5068284 - Image 5

376 South Ridge Drive # 31 Middlebury, VT MLS# 5068284 - Image 6

376 South Ridge Drive # 31 Middlebury, VT MLS# 5068284 - Image 7

376 South Ridge Drive # 31 Middlebury, VT MLS# 5068284 - Image 8

376 South Ridge Drive # 31 Middlebury, VT MLS# 5068284 - Image 9

376 South Ridge Drive # 31 Middlebury, VT MLS# 5068284 - Image 10

376 South Ridge Drive # 31 Middlebury, VT MLS# 5068284 - Image 11

1 of 11

$199,000

Studio

Beds

0.0

Baths

376 South Ridge Drive # 31

Middlebury, VT

Courtesy of IPJ REAL ESTATE

20 Forest Ridge Drive # 14 Middlebury, VT MLS# 5072447 - Image 1

20 Forest Ridge Drive # 14 Middlebury, VT MLS# 5072447 - Image 2

20 Forest Ridge Drive # 14 Middlebury, VT MLS# 5072447 - Image 3

20 Forest Ridge Drive # 14 Middlebury, VT MLS# 5072447 - Image 4

20 Forest Ridge Drive # 14 Middlebury, VT MLS# 5072447 - Image 5

20 Forest Ridge Drive # 14 Middlebury, VT MLS# 5072447 - Image 6

20 Forest Ridge Drive # 14 Middlebury, VT MLS# 5072447 - Image 7

20 Forest Ridge Drive # 14 Middlebury, VT MLS# 5072447 - Image 8

1 of 8

$185,000

Studio

Beds

0.0

Baths

20 Forest Ridge Drive # 14

Middlebury, VT

Courtesy of BHHS VERMONT REALTY GROUP/MIDDLEBURY

6 Fred Johnson Circle # 17 Middlebury, VT MLS# 5072450 - Image 1

6 Fred Johnson Circle # 17 Middlebury, VT MLS# 5072450 - Image 2

6 Fred Johnson Circle # 17 Middlebury, VT MLS# 5072450 - Image 3

6 Fred Johnson Circle # 17 Middlebury, VT MLS# 5072450 - Image 4

6 Fred Johnson Circle # 17 Middlebury, VT MLS# 5072450 - Image 5

6 Fred Johnson Circle # 17 Middlebury, VT MLS# 5072450 - Image 6

1 of 6

$154,000

Studio

Beds

0.0

Baths

6 Fred Johnson Circle # 17

Middlebury, VT

Courtesy of BHHS VERMONT REALTY GROUP/MIDDLEBURY

TBD Middle Road North Middlebury, VT MLS# 5068334 - Image 1

TBD Middle Road North Middlebury, VT MLS# 5068334 - Image 2

TBD Middle Road North Middlebury, VT MLS# 5068334 - Image 3

1 of 3

$149,000

Studio

Beds

0.0

Baths

TBD Middle Road North

Middlebury, VT

Courtesy of IPJ REAL ESTATE

8 Fred Johnson Circle # 16 Middlebury, VT MLS# 5072452 - Image 1

8 Fred Johnson Circle # 16 Middlebury, VT MLS# 5072452 - Image 2

8 Fred Johnson Circle # 16 Middlebury, VT MLS# 5072452 - Image 3

8 Fred Johnson Circle # 16 Middlebury, VT MLS# 5072452 - Image 4

8 Fred Johnson Circle # 16 Middlebury, VT MLS# 5072452 - Image 5

8 Fred Johnson Circle # 16 Middlebury, VT MLS# 5072452 - Image 6

1 of 6

$149,000

Studio

Beds

0.0

Baths

8 Fred Johnson Circle # 16

Middlebury, VT

Courtesy of BHHS VERMONT REALTY GROUP/MIDDLEBURY

Upper Plains Road Middlebury, VT MLS# 5053030 - Image 1

Upper Plains Road Middlebury, VT MLS# 5053030 - Image 2

Upper Plains Road Middlebury, VT MLS# 5053030 - Image 3

Upper Plains Road Middlebury, VT MLS# 5053030 - Image 4

Upper Plains Road Middlebury, VT MLS# 5053030 - Image 5

Upper Plains Road Middlebury, VT MLS# 5053030 - Image 6

Upper Plains Road Middlebury, VT MLS# 5053030 - Image 7

Upper Plains Road Middlebury, VT MLS# 5053030 - Image 8

Upper Plains Road Middlebury, VT MLS# 5053030 - Image 9

1 of 9

$146,000

Studio

Beds

0.0

Baths

Upper Plains Road

Middlebury, VT

Courtesy of VERMONT FOREST AND FIELD, INC.

Lot 1C Daisy Lane # Lot 1C Middlebury, VT MLS# 5046645 - Image 1

Lot 1C Daisy Lane # Lot 1C Middlebury, VT MLS# 5046645 - Image 2

Lot 1C Daisy Lane # Lot 1C Middlebury, VT MLS# 5046645 - Image 3

Lot 1C Daisy Lane # Lot 1C Middlebury, VT MLS# 5046645 - Image 4

Lot 1C Daisy Lane # Lot 1C Middlebury, VT MLS# 5046645 - Image 5

Lot 1C Daisy Lane # Lot 1C Middlebury, VT MLS# 5046645 - Image 6

Lot 1C Daisy Lane # Lot 1C Middlebury, VT MLS# 5046645 - Image 7

Lot 1C Daisy Lane # Lot 1C Middlebury, VT MLS# 5046645 - Image 8

Lot 1C Daisy Lane # Lot 1C Middlebury, VT MLS# 5046645 - Image 9

Lot 1C Daisy Lane # Lot 1C Middlebury, VT MLS# 5046645 - Image 10

Lot 1C Daisy Lane # Lot 1C Middlebury, VT MLS# 5046645 - Image 11

1 of 11

$139,000

Studio

Beds

0.0

Baths

Lot 1C Daisy Lane # Lot 1C

Middlebury, VT

Courtesy of IPJ REAL ESTATE

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 1

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 2

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 3

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 4

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 5

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 6

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 7

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 8

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 9

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 10

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 11

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 12

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 13

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 14

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 15

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 16

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 17

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 18

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 19

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 20

31 Parkline Place Middlebury, VT MLS# 5073125 - Image 21

1 of 21

$75,000

Beds

1.0

Baths

728

Sq.Ft.

31 Parkline Place

Middlebury, VT

Courtesy of EMILO REAL ESTATE, LLC

20 Nashua Lane Middlebury, VT MLS# 5074069 - Image 1

20 Nashua Lane Middlebury, VT MLS# 5074069 - Image 2

20 Nashua Lane Middlebury, VT MLS# 5074069 - Image 3

20 Nashua Lane Middlebury, VT MLS# 5074069 - Image 4

20 Nashua Lane Middlebury, VT MLS# 5074069 - Image 5

20 Nashua Lane Middlebury, VT MLS# 5074069 - Image 6

20 Nashua Lane Middlebury, VT MLS# 5074069 - Image 7

20 Nashua Lane Middlebury, VT MLS# 5074069 - Image 8

20 Nashua Lane Middlebury, VT MLS# 5074069 - Image 9

20 Nashua Lane Middlebury, VT MLS# 5074069 - Image 10

20 Nashua Lane Middlebury, VT MLS# 5074069 - Image 11

20 Nashua Lane Middlebury, VT MLS# 5074069 - Image 12

20 Nashua Lane Middlebury, VT MLS# 5074069 - Image 13

20 Nashua Lane Middlebury, VT MLS# 5074069 - Image 14

1 of 14

$40,000

Beds

1.0

Baths

672

Sq.Ft.

20 Nashua Lane

Middlebury, VT

Courtesy of EMILO REAL ESTATE, LLC

About Middlebury

Listings in Middlebury, VT: 43
Estimated median home price: $407,000

Middlebury VT Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Middlebury, Vermont real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Middlebury, VT.

Homes for Sale by Price in Middlebury, VT

Price	Count
$0 - 100K	2
$100K - 200K	7
$200K - 300K	2
$300K - 400K	10
$400K - 500K	12
$500K - 600K	2
$600K - 700K	5
$700K - 800K	0
$800K - 900K	2
$900K - 1M	1
$1M - Max	0

Homes for Sale by Type in Middlebury, VT

Property Type	Count
Single Family	22
Townhouse	0
Condo	9
Commercial	2
Rental	2
Lots and Land	8
Condo/Town/CoOp	0
CoOp	0
Multi Family	0
Mobile Home	2
Farms	0

(Data as of 2/20/2026)

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Middlebury, VT Information

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05753

Information deemed reliable but not guaranteed.

“Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 2/20/2026”

Trends Information provided by ATTOM Data Solutions.

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Middlebury Vermont Homes for Sale

About Middlebury

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Middlebury Vermont Homes for Sale

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