Chester Vermont Homes for Sale

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3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 1

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 2

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 3

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 4

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 5

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 6

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 7

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 8

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 9

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 10

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 11

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 12

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 13

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 14

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 15

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 16

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 17

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 18

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 19

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 20

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 21

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 22

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 23

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 24

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 25

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 26

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 27

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 28

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 29

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 30

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 31

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 32

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 33

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 34

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 35

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 36

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 37

3668 VT Route 103 North Chester, VT MLS# 5097621 - Image 38

1 of 38

$249,500

Beds

3.0

Baths

1,922

Sq.Ft.

3668 VT Route 103 North

Chester, VT

Courtesy of MARY W. DAVIS REALTOR & ASSOC., INC.

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 1

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 2

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 3

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 4

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 5

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 6

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 7

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 8

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 9

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 10

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 11

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 12

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 13

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 14

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 15

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 16

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 17

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 18

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 19

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 20

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 21

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 22

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 23

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 24

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 25

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 26

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 27

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 28

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 29

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 30

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 31

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 32

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 33

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 34

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 35

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 36

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 37

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 38

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 39

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 40

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 41

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 42

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 43

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 44

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 45

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 46

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 47

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 48

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 49

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 50

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 51

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 52

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 53

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 54

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 55

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 56

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 57

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 58

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 59

3781 Flamstead Road Chester, VT MLS# 5102142 - Image 60

Recently Listed

1 of 60

$250,000

Beds

2.0

Baths

1,500

Sq.Ft.

3781 Flamstead Road

Chester, VT

Courtesy of EXP REALTY

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 1

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 2

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 3

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 4

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 5

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 6

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 7

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 8

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 9

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 10

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 11

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 12

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 13

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 14

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 15

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 16

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 17

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 18

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 19

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 20

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 21

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 22

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 23

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 24

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 25

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 26

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 27

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 28

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 29

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 30

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 31

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 32

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 33

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 34

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 35

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 36

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 37

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 38

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 39

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 40

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 41

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 42

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 43

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 44

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 45

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 46

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 47

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 48

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 49

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 50

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 51

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 52

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 53

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 54

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 55

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 56

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 57

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 58

3781 Flamstead Road Chester, VT MLS# 5102143 - Image 59

Recently Listed

1 of 59

$250,000

Studio

Beds

0.0

Baths

3781 Flamstead Road

Chester, VT

Courtesy of EXP REALTY

THE TIME TO SELL IS NOW!

1175 Quarry Road Chester, VT MLS# 5058824 - Image 1

1175 Quarry Road Chester, VT MLS# 5058824 - Image 2

1175 Quarry Road Chester, VT MLS# 5058824 - Image 3

1175 Quarry Road Chester, VT MLS# 5058824 - Image 4

1175 Quarry Road Chester, VT MLS# 5058824 - Image 5

1175 Quarry Road Chester, VT MLS# 5058824 - Image 6

1175 Quarry Road Chester, VT MLS# 5058824 - Image 7

1175 Quarry Road Chester, VT MLS# 5058824 - Image 8

1175 Quarry Road Chester, VT MLS# 5058824 - Image 9

1175 Quarry Road Chester, VT MLS# 5058824 - Image 10

1175 Quarry Road Chester, VT MLS# 5058824 - Image 11

1175 Quarry Road Chester, VT MLS# 5058824 - Image 12

1175 Quarry Road Chester, VT MLS# 5058824 - Image 13

1175 Quarry Road Chester, VT MLS# 5058824 - Image 14

1175 Quarry Road Chester, VT MLS# 5058824 - Image 15

1175 Quarry Road Chester, VT MLS# 5058824 - Image 16

1175 Quarry Road Chester, VT MLS# 5058824 - Image 17

1175 Quarry Road Chester, VT MLS# 5058824 - Image 18

1175 Quarry Road Chester, VT MLS# 5058824 - Image 19

1175 Quarry Road Chester, VT MLS# 5058824 - Image 20

1175 Quarry Road Chester, VT MLS# 5058824 - Image 21

1175 Quarry Road Chester, VT MLS# 5058824 - Image 22

1175 Quarry Road Chester, VT MLS# 5058824 - Image 23

1175 Quarry Road Chester, VT MLS# 5058824 - Image 24

1175 Quarry Road Chester, VT MLS# 5058824 - Image 25

1175 Quarry Road Chester, VT MLS# 5058824 - Image 26

1175 Quarry Road Chester, VT MLS# 5058824 - Image 27

1 of 27

$270,000

Studio

Beds

0.0

Baths

1175 Quarry Road

Chester, VT

Courtesy of BHG MASIELLO KEENE

39 S Main Street Chester, VT MLS# 5100522 - Image 1

39 S Main Street Chester, VT MLS# 5100522 - Image 2

39 S Main Street Chester, VT MLS# 5100522 - Image 3

39 S Main Street Chester, VT MLS# 5100522 - Image 4

39 S Main Street Chester, VT MLS# 5100522 - Image 5

39 S Main Street Chester, VT MLS# 5100522 - Image 6

39 S Main Street Chester, VT MLS# 5100522 - Image 7

39 S Main Street Chester, VT MLS# 5100522 - Image 8

39 S Main Street Chester, VT MLS# 5100522 - Image 9

Recently Listed

1 of 9

$285,000

1,802

Sq.Ft.

39 S Main Street

Chester, VT

Courtesy of WILLIAM RAVEIS REAL ESTATE VERMONT PROPERTIES

106 Contro Road Chester, VT MLS# 5069928 - Image 1

106 Contro Road Chester, VT MLS# 5069928 - Image 2

106 Contro Road Chester, VT MLS# 5069928 - Image 3

106 Contro Road Chester, VT MLS# 5069928 - Image 4

106 Contro Road Chester, VT MLS# 5069928 - Image 5

106 Contro Road Chester, VT MLS# 5069928 - Image 6

106 Contro Road Chester, VT MLS# 5069928 - Image 7

106 Contro Road Chester, VT MLS# 5069928 - Image 8

106 Contro Road Chester, VT MLS# 5069928 - Image 9

106 Contro Road Chester, VT MLS# 5069928 - Image 10

106 Contro Road Chester, VT MLS# 5069928 - Image 11

106 Contro Road Chester, VT MLS# 5069928 - Image 12

106 Contro Road Chester, VT MLS# 5069928 - Image 13

106 Contro Road Chester, VT MLS# 5069928 - Image 14

1 of 14

$289,000

Beds

2.1

Baths

1,475

Sq.Ft.

106 Contro Road

Chester, VT

Courtesy of BRATTLEBORO AREA REALTY

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 1

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 2

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 3

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 4

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 5

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 6

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 7

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 8

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 9

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 10

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 11

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 12

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 13

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 14

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 15

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 16

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 17

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 18

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 19

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 20

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 21

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 22

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 23

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 24

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 25

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 26

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 27

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 28

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 29

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 30

1397 Popple Dungeon Road Chester, VT MLS# 5073930 - Image 31

1 of 31

$299,000

Beds

2.0

Baths

1,788

Sq.Ft.

1397 Popple Dungeon Road

Chester, VT

Courtesy of BARRETT AND VALLEY ASSOCIATES INC.

397 River Street Chester, VT MLS# 5087965 - Image 1

397 River Street Chester, VT MLS# 5087965 - Image 2

397 River Street Chester, VT MLS# 5087965 - Image 3

397 River Street Chester, VT MLS# 5087965 - Image 4

397 River Street Chester, VT MLS# 5087965 - Image 5

397 River Street Chester, VT MLS# 5087965 - Image 6

397 River Street Chester, VT MLS# 5087965 - Image 7

397 River Street Chester, VT MLS# 5087965 - Image 8

397 River Street Chester, VT MLS# 5087965 - Image 9

397 River Street Chester, VT MLS# 5087965 - Image 10

397 River Street Chester, VT MLS# 5087965 - Image 11

397 River Street Chester, VT MLS# 5087965 - Image 12

397 River Street Chester, VT MLS# 5087965 - Image 13

397 River Street Chester, VT MLS# 5087965 - Image 14

397 River Street Chester, VT MLS# 5087965 - Image 15

397 River Street Chester, VT MLS# 5087965 - Image 16

397 River Street Chester, VT MLS# 5087965 - Image 17

397 River Street Chester, VT MLS# 5087965 - Image 18

397 River Street Chester, VT MLS# 5087965 - Image 19

397 River Street Chester, VT MLS# 5087965 - Image 20

397 River Street Chester, VT MLS# 5087965 - Image 21

397 River Street Chester, VT MLS# 5087965 - Image 22

397 River Street Chester, VT MLS# 5087965 - Image 23

397 River Street Chester, VT MLS# 5087965 - Image 24

397 River Street Chester, VT MLS# 5087965 - Image 25

397 River Street Chester, VT MLS# 5087965 - Image 26

397 River Street Chester, VT MLS# 5087965 - Image 27

397 River Street Chester, VT MLS# 5087965 - Image 28

397 River Street Chester, VT MLS# 5087965 - Image 29

397 River Street Chester, VT MLS# 5087965 - Image 30

397 River Street Chester, VT MLS# 5087965 - Image 31

397 River Street Chester, VT MLS# 5087965 - Image 32

397 River Street Chester, VT MLS# 5087965 - Image 33

397 River Street Chester, VT MLS# 5087965 - Image 34

397 River Street Chester, VT MLS# 5087965 - Image 35

397 River Street Chester, VT MLS# 5087965 - Image 36

397 River Street Chester, VT MLS# 5087965 - Image 37

397 River Street Chester, VT MLS# 5087965 - Image 38

397 River Street Chester, VT MLS# 5087965 - Image 39

397 River Street Chester, VT MLS# 5087965 - Image 40

397 River Street Chester, VT MLS# 5087965 - Image 41

1 of 41

$325,000

Beds

3.0

Baths

3,332

Sq.Ft.

397 River Street

Chester, VT

Courtesy of CUMMINGS & CO

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 1

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 2

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 3

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 4

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 5

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 6

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 7

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 8

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 9

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 10

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 11

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 12

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 13

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 14

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 15

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 16

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 17

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 18

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 19

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 20

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 21

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 22

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 23

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 24

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 25

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 26

302 Davidson Hill Road Chester, VT MLS# 5102316 - Image 27

Recently Listed

1 of 27

OPEN HOUSE: Sunday 8/9 1:00 PM - 3:00 PM

$359,000

Beds

1.0

Baths

900

Sq.Ft.

302 Davidson Hill Road

Chester, VT

Courtesy of VERMONT REAL ESTATE COMPANY

145 South Main Street Chester, VT MLS# 5097411 - Image 1

145 South Main Street Chester, VT MLS# 5097411 - Image 2

145 South Main Street Chester, VT MLS# 5097411 - Image 3

145 South Main Street Chester, VT MLS# 5097411 - Image 4

145 South Main Street Chester, VT MLS# 5097411 - Image 5

145 South Main Street Chester, VT MLS# 5097411 - Image 6

145 South Main Street Chester, VT MLS# 5097411 - Image 7

145 South Main Street Chester, VT MLS# 5097411 - Image 8

145 South Main Street Chester, VT MLS# 5097411 - Image 9

145 South Main Street Chester, VT MLS# 5097411 - Image 10

1 of 10

$385,000

3,608

Sq.Ft.

145 South Main Street

Chester, VT

Courtesy of NANCY JENKINS REAL ESTATE

663 Depot Street Chester, VT MLS# 5086202 - Image 1

663 Depot Street Chester, VT MLS# 5086202 - Image 2

663 Depot Street Chester, VT MLS# 5086202 - Image 3

663 Depot Street Chester, VT MLS# 5086202 - Image 4

663 Depot Street Chester, VT MLS# 5086202 - Image 5

663 Depot Street Chester, VT MLS# 5086202 - Image 6

663 Depot Street Chester, VT MLS# 5086202 - Image 7

663 Depot Street Chester, VT MLS# 5086202 - Image 8

663 Depot Street Chester, VT MLS# 5086202 - Image 9

663 Depot Street Chester, VT MLS# 5086202 - Image 10

663 Depot Street Chester, VT MLS# 5086202 - Image 11

663 Depot Street Chester, VT MLS# 5086202 - Image 12

663 Depot Street Chester, VT MLS# 5086202 - Image 13

663 Depot Street Chester, VT MLS# 5086202 - Image 14

663 Depot Street Chester, VT MLS# 5086202 - Image 15

663 Depot Street Chester, VT MLS# 5086202 - Image 16

663 Depot Street Chester, VT MLS# 5086202 - Image 17

663 Depot Street Chester, VT MLS# 5086202 - Image 18

663 Depot Street Chester, VT MLS# 5086202 - Image 19

663 Depot Street Chester, VT MLS# 5086202 - Image 20

663 Depot Street Chester, VT MLS# 5086202 - Image 21

663 Depot Street Chester, VT MLS# 5086202 - Image 22

663 Depot Street Chester, VT MLS# 5086202 - Image 23

663 Depot Street Chester, VT MLS# 5086202 - Image 24

663 Depot Street Chester, VT MLS# 5086202 - Image 25

663 Depot Street Chester, VT MLS# 5086202 - Image 26

663 Depot Street Chester, VT MLS# 5086202 - Image 27

663 Depot Street Chester, VT MLS# 5086202 - Image 28

663 Depot Street Chester, VT MLS# 5086202 - Image 29

663 Depot Street Chester, VT MLS# 5086202 - Image 30

663 Depot Street Chester, VT MLS# 5086202 - Image 31

663 Depot Street Chester, VT MLS# 5086202 - Image 32

663 Depot Street Chester, VT MLS# 5086202 - Image 33

663 Depot Street Chester, VT MLS# 5086202 - Image 34

663 Depot Street Chester, VT MLS# 5086202 - Image 35

663 Depot Street Chester, VT MLS# 5086202 - Image 36

663 Depot Street Chester, VT MLS# 5086202 - Image 37

663 Depot Street Chester, VT MLS# 5086202 - Image 38

663 Depot Street Chester, VT MLS# 5086202 - Image 39

663 Depot Street Chester, VT MLS# 5086202 - Image 40

663 Depot Street Chester, VT MLS# 5086202 - Image 41

663 Depot Street Chester, VT MLS# 5086202 - Image 42

663 Depot Street Chester, VT MLS# 5086202 - Image 43

663 Depot Street Chester, VT MLS# 5086202 - Image 44

663 Depot Street Chester, VT MLS# 5086202 - Image 45

663 Depot Street Chester, VT MLS# 5086202 - Image 46

663 Depot Street Chester, VT MLS# 5086202 - Image 47

663 Depot Street Chester, VT MLS# 5086202 - Image 48

663 Depot Street Chester, VT MLS# 5086202 - Image 49

663 Depot Street Chester, VT MLS# 5086202 - Image 50

663 Depot Street Chester, VT MLS# 5086202 - Image 51

1 of 51

$390,000

Beds

2.0

Baths

1,304

Sq.Ft.

663 Depot Street

Chester, VT

Courtesy of REAL BROKER LLC

40 Fenton Road Chester, VT MLS# 5073147 - Image 1

40 Fenton Road Chester, VT MLS# 5073147 - Image 2

40 Fenton Road Chester, VT MLS# 5073147 - Image 3

40 Fenton Road Chester, VT MLS# 5073147 - Image 4

40 Fenton Road Chester, VT MLS# 5073147 - Image 5

40 Fenton Road Chester, VT MLS# 5073147 - Image 6

40 Fenton Road Chester, VT MLS# 5073147 - Image 7

40 Fenton Road Chester, VT MLS# 5073147 - Image 8

40 Fenton Road Chester, VT MLS# 5073147 - Image 9

40 Fenton Road Chester, VT MLS# 5073147 - Image 10

40 Fenton Road Chester, VT MLS# 5073147 - Image 11

40 Fenton Road Chester, VT MLS# 5073147 - Image 12

40 Fenton Road Chester, VT MLS# 5073147 - Image 13

40 Fenton Road Chester, VT MLS# 5073147 - Image 14

40 Fenton Road Chester, VT MLS# 5073147 - Image 15

40 Fenton Road Chester, VT MLS# 5073147 - Image 16

40 Fenton Road Chester, VT MLS# 5073147 - Image 17

40 Fenton Road Chester, VT MLS# 5073147 - Image 18

40 Fenton Road Chester, VT MLS# 5073147 - Image 19

40 Fenton Road Chester, VT MLS# 5073147 - Image 20

40 Fenton Road Chester, VT MLS# 5073147 - Image 21

40 Fenton Road Chester, VT MLS# 5073147 - Image 22

40 Fenton Road Chester, VT MLS# 5073147 - Image 23

40 Fenton Road Chester, VT MLS# 5073147 - Image 24

40 Fenton Road Chester, VT MLS# 5073147 - Image 25

40 Fenton Road Chester, VT MLS# 5073147 - Image 26

40 Fenton Road Chester, VT MLS# 5073147 - Image 27

40 Fenton Road Chester, VT MLS# 5073147 - Image 28

40 Fenton Road Chester, VT MLS# 5073147 - Image 29

40 Fenton Road Chester, VT MLS# 5073147 - Image 30

40 Fenton Road Chester, VT MLS# 5073147 - Image 31

40 Fenton Road Chester, VT MLS# 5073147 - Image 32

40 Fenton Road Chester, VT MLS# 5073147 - Image 33

40 Fenton Road Chester, VT MLS# 5073147 - Image 34

40 Fenton Road Chester, VT MLS# 5073147 - Image 35

40 Fenton Road Chester, VT MLS# 5073147 - Image 36

40 Fenton Road Chester, VT MLS# 5073147 - Image 37

1 of 37

$399,000

Beds

2.1

Baths

2,148

Sq.Ft.

40 Fenton Road

Chester, VT

Courtesy of TPW REAL ESTATE

176 Meadow Road Chester, VT MLS# 5082995 - Image 1

176 Meadow Road Chester, VT MLS# 5082995 - Image 2

176 Meadow Road Chester, VT MLS# 5082995 - Image 3

176 Meadow Road Chester, VT MLS# 5082995 - Image 4

176 Meadow Road Chester, VT MLS# 5082995 - Image 5

176 Meadow Road Chester, VT MLS# 5082995 - Image 6

176 Meadow Road Chester, VT MLS# 5082995 - Image 7

176 Meadow Road Chester, VT MLS# 5082995 - Image 8

176 Meadow Road Chester, VT MLS# 5082995 - Image 9

176 Meadow Road Chester, VT MLS# 5082995 - Image 10

176 Meadow Road Chester, VT MLS# 5082995 - Image 11

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176 Meadow Road Chester, VT MLS# 5082995 - Image 13

176 Meadow Road Chester, VT MLS# 5082995 - Image 14

176 Meadow Road Chester, VT MLS# 5082995 - Image 15

176 Meadow Road Chester, VT MLS# 5082995 - Image 16

176 Meadow Road Chester, VT MLS# 5082995 - Image 17

176 Meadow Road Chester, VT MLS# 5082995 - Image 18

176 Meadow Road Chester, VT MLS# 5082995 - Image 19

176 Meadow Road Chester, VT MLS# 5082995 - Image 20

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176 Meadow Road Chester, VT MLS# 5082995 - Image 25

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176 Meadow Road Chester, VT MLS# 5082995 - Image 39

176 Meadow Road Chester, VT MLS# 5082995 - Image 40

176 Meadow Road Chester, VT MLS# 5082995 - Image 41

176 Meadow Road Chester, VT MLS# 5082995 - Image 42

176 Meadow Road Chester, VT MLS# 5082995 - Image 43

1 of 43

$419,900

Beds

2.0

Baths

1,982

Sq.Ft.

176 Meadow Road

Chester, VT

Courtesy of BERKSHIRE HATHAWAY HOMESERVICES STRATTON HOME

81 Main Street Chester, VT MLS# 5095551 - Image 1

81 Main Street Chester, VT MLS# 5095551 - Image 2

81 Main Street Chester, VT MLS# 5095551 - Image 3

81 Main Street Chester, VT MLS# 5095551 - Image 4

81 Main Street Chester, VT MLS# 5095551 - Image 5

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81 Main Street Chester, VT MLS# 5095551 - Image 15

81 Main Street Chester, VT MLS# 5095551 - Image 16

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81 Main Street Chester, VT MLS# 5095551 - Image 46

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81 Main Street Chester, VT MLS# 5095551 - Image 55

81 Main Street Chester, VT MLS# 5095551 - Image 56

81 Main Street Chester, VT MLS# 5095551 - Image 57

81 Main Street Chester, VT MLS# 5095551 - Image 58

Virtual Tour

1 of 58

$450,000

Beds

4.0

Baths

3,865

Sq.Ft.

81 Main Street

Chester, VT

Courtesy of REAL BROKER LLC

64 Maple Street Chester, VT MLS# 5087175 - Image 1

64 Maple Street Chester, VT MLS# 5087175 - Image 2

64 Maple Street Chester, VT MLS# 5087175 - Image 3

64 Maple Street Chester, VT MLS# 5087175 - Image 4

64 Maple Street Chester, VT MLS# 5087175 - Image 5

64 Maple Street Chester, VT MLS# 5087175 - Image 6

64 Maple Street Chester, VT MLS# 5087175 - Image 7

64 Maple Street Chester, VT MLS# 5087175 - Image 8

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64 Maple Street Chester, VT MLS# 5087175 - Image 16

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64 Maple Street Chester, VT MLS# 5087175 - Image 18

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64 Maple Street Chester, VT MLS# 5087175 - Image 21

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64 Maple Street Chester, VT MLS# 5087175 - Image 23

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64 Maple Street Chester, VT MLS# 5087175 - Image 56

64 Maple Street Chester, VT MLS# 5087175 - Image 57

64 Maple Street Chester, VT MLS# 5087175 - Image 58

64 Maple Street Chester, VT MLS# 5087175 - Image 59

64 Maple Street Chester, VT MLS# 5087175 - Image 60

Virtual Tour

1 of 60

$469,000

Beds

3.0

Baths

2,676

Sq.Ft.

64 Maple Street

Chester, VT

Courtesy of REAL BROKER LLC

3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 1

3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 2

3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 3

3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 4

3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 5

3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 6

3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 7

3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 8

3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 9

3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 10

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3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 14

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3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 16

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3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 18

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3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 22

3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 23

3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 24

3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 25

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3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 27

3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 28

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3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 31

3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 32

3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 33

3208 Green Mountain Turnpike Chester, VT MLS# 5095486 - Image 34

Virtual Tour

1 of 34

$489,000

Beds

2.0

Baths

1,626

Sq.Ft.

3208 Green Mountain Turnpike

Chester, VT

Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY

3078 VT Route 10 Chester, VT MLS# 5095371 - Image 1

3078 VT Route 10 Chester, VT MLS# 5095371 - Image 2

3078 VT Route 10 Chester, VT MLS# 5095371 - Image 3

3078 VT Route 10 Chester, VT MLS# 5095371 - Image 4

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3078 VT Route 10 Chester, VT MLS# 5095371 - Image 7

3078 VT Route 10 Chester, VT MLS# 5095371 - Image 8

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3078 VT Route 10 Chester, VT MLS# 5095371 - Image 57

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3078 VT Route 10 Chester, VT MLS# 5095371 - Image 59

3078 VT Route 10 Chester, VT MLS# 5095371 - Image 60

1 of 60

$495,000

Beds

2.0

Baths

1,800

Sq.Ft.

3078 VT Route 10

Chester, VT

Courtesy of KELLEY REAL ESTATE, INC.

3341 Trebo Road Chester, VT MLS# 5086105 - Image 1

3341 Trebo Road Chester, VT MLS# 5086105 - Image 2

3341 Trebo Road Chester, VT MLS# 5086105 - Image 3

3341 Trebo Road Chester, VT MLS# 5086105 - Image 4

3341 Trebo Road Chester, VT MLS# 5086105 - Image 5

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3341 Trebo Road Chester, VT MLS# 5086105 - Image 7

3341 Trebo Road Chester, VT MLS# 5086105 - Image 8

3341 Trebo Road Chester, VT MLS# 5086105 - Image 9

3341 Trebo Road Chester, VT MLS# 5086105 - Image 10

3341 Trebo Road Chester, VT MLS# 5086105 - Image 11

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3341 Trebo Road Chester, VT MLS# 5086105 - Image 13

3341 Trebo Road Chester, VT MLS# 5086105 - Image 14

3341 Trebo Road Chester, VT MLS# 5086105 - Image 15

3341 Trebo Road Chester, VT MLS# 5086105 - Image 16

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3341 Trebo Road Chester, VT MLS# 5086105 - Image 37

3341 Trebo Road Chester, VT MLS# 5086105 - Image 38

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3341 Trebo Road Chester, VT MLS# 5086105 - Image 41

3341 Trebo Road Chester, VT MLS# 5086105 - Image 42

3341 Trebo Road Chester, VT MLS# 5086105 - Image 43

3341 Trebo Road Chester, VT MLS# 5086105 - Image 44

3341 Trebo Road Chester, VT MLS# 5086105 - Image 45

3341 Trebo Road Chester, VT MLS# 5086105 - Image 46

3341 Trebo Road Chester, VT MLS# 5086105 - Image 47

1 of 47

$549,000

Beds

2.1

Baths

2,464

Sq.Ft.

3341 Trebo Road

Chester, VT

Courtesy of BARRETT AND VALLEY ASSOCIATES INC.

168 Chandler Road Chester, VT MLS# 5097737 - Image 1

168 Chandler Road Chester, VT MLS# 5097737 - Image 2

168 Chandler Road Chester, VT MLS# 5097737 - Image 3

168 Chandler Road Chester, VT MLS# 5097737 - Image 4

168 Chandler Road Chester, VT MLS# 5097737 - Image 5

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168 Chandler Road Chester, VT MLS# 5097737 - Image 15

168 Chandler Road Chester, VT MLS# 5097737 - Image 16

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168 Chandler Road Chester, VT MLS# 5097737 - Image 18

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168 Chandler Road Chester, VT MLS# 5097737 - Image 23

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168 Chandler Road Chester, VT MLS# 5097737 - Image 25

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168 Chandler Road Chester, VT MLS# 5097737 - Image 46

168 Chandler Road Chester, VT MLS# 5097737 - Image 47

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168 Chandler Road Chester, VT MLS# 5097737 - Image 49

168 Chandler Road Chester, VT MLS# 5097737 - Image 50

168 Chandler Road Chester, VT MLS# 5097737 - Image 51

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168 Chandler Road Chester, VT MLS# 5097737 - Image 53

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168 Chandler Road Chester, VT MLS# 5097737 - Image 55

168 Chandler Road Chester, VT MLS# 5097737 - Image 56

168 Chandler Road Chester, VT MLS# 5097737 - Image 57

168 Chandler Road Chester, VT MLS# 5097737 - Image 58

168 Chandler Road Chester, VT MLS# 5097737 - Image 59

168 Chandler Road Chester, VT MLS# 5097737 - Image 60

Virtual Tour

1 of 60

$649,000

Beds

2.0

Baths

2,204

Sq.Ft.

168 Chandler Road

Chester, VT

Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 1

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 2

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 3

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 4

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 5

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 6

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 7

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 8

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 9

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 10

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 11

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 12

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 13

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 14

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 15

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 16

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 17

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 18

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3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 21

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 22

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 23

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 24

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 25

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 26

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 27

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 28

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 29

3630 Vt Route 103 N Chester, VT MLS# 5044879 - Image 30

1 of 30

$650,000

Beds

3.0

Baths

4,324

Sq.Ft.

3630 Vt Route 103 N

Chester, VT

Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY

About Chester

Listings in Chester, VT: 48
Estimated median home price: $277,500

Chester VT Homes for Sale & Properties

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

Homes for Sale by Price in Chester, VT

Price	Count
$0 - 100K	8
$100K - 200K	9
$200K - 300K	10
$300K - 400K	5
$400K - 500K	5
$500K - 600K	1
$600K - 700K	4
$700K - 800K	2
$800K - 900K	0
$900K - 1M	1
$1M - Max	3

Homes for Sale by Type in Chester, VT

Property Type	Count
Single Family	24
Townhouse	0
Condo	0
Commercial	5
Rental	2
Lots and Land	16
Condo/Town/CoOp	0
CoOp	0
Multi Family	2
Mobile Home	1
Farms	0

(Data as of 8/4/2026)

Find Properties in Chester, VT

Chester, VT Information

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05143

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 8/7/2026”

Trends Information provided by ATTOM Data Solutions.

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