Bennington Vermont Homes for Sale

279 total properties
View 551 West Fields Road Manchester, VT MLS# 5052301
  • New Construction with Virtual Tour
Save 551 West Fields Road Manchester, VT MLS# 5052301
1 of 55
$10,300,000
6

Beds

7.2

Baths

10,993

Sq.Ft.

551 West Fields Road

Manchester, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 515 West Fields Road Manchester, VT MLS# 4974441
  • Virtual Tour
Save 515 West Fields Road Manchester, VT MLS# 4974441
1 of 40
$6,900,000
5

Beds

5.1

Baths

6,500

Sq.Ft.

515 West Fields Road

Manchester, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 178 Conservation Way Sunderland, VT MLS# 5036338
Save 178 Conservation Way Sunderland, VT MLS# 5036338
1 of 3
$5,850,000
58,000

Sq.Ft.

178 Conservation Way

Sunderland, VT

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Courtesy of HOSPITALITY CONSULTANTS, LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1060 Upper Hollow Road Dorset, VT MLS# 5075285
Save 1060 Upper Hollow Road Dorset, VT MLS# 5075285
1 of 60
$5,600,000
5

Beds

5.1

Baths

4,674

Sq.Ft.

1060 Upper Hollow Road

Dorset, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 1182 1184 East Manchester Road Manchester, VT MLS# 5063499
  • Virtual Tour
Save 1182 1184 East Manchester Road Manchester, VT MLS# 5063499
1 of 60
$5,250,000
9

Beds

7.3

Baths

7,900

Sq.Ft.

1182 1184 East Manchester Road

Manchester, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 507 Benson Road Manchester, VT MLS# 5011616
  • Virtual Tour
Save 507 Benson Road Manchester, VT MLS# 5011616
1 of 37
$4,975,000
5,445

Sq.Ft.

507 Benson Road

Manchester, VT

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Courtesy of LANDVEST, INC/WOODSTOCK
View 527 Benson Road Manchester, VT MLS# 5011880
  • Virtual Tour
Save 527 Benson Road Manchester, VT MLS# 5011880
1 of 38
$4,975,000
5

Beds

4.0

Baths

6,998

Sq.Ft.

527 Benson Road

Manchester, VT

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Courtesy of LANDVEST, INC/WOODSTOCK
View 318 Spring Hill Lane Dorset, VT MLS# 5042119
  • Virtual Tour
Save 318 Spring Hill Lane Dorset, VT MLS# 5042119
1 of 50
$4,500,000
7

Beds

10.0

Baths

7,422

Sq.Ft.

318 Spring Hill Lane

Dorset, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 466 Three Maple Drive Manchester, VT MLS# 5065200
Save 466 Three Maple Drive Manchester, VT MLS# 5065200
1 of 56
$3,350,000
3

Beds

4.1

Baths

3,059

Sq.Ft.

466 Three Maple Drive

Manchester, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 114 Cemetery Avenue Manchester, VT MLS# 5064256
Save 114 Cemetery Avenue Manchester, VT MLS# 5064256
1 of 51
$3,250,000
8,288

Sq.Ft.

114 Cemetery Avenue

Manchester, VT

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Courtesy of WOHLER REALTY GROUP
View 67 High Meadow Road Winhall, VT MLS# 5074118
Save 67 High Meadow Road Winhall, VT MLS# 5074118
1 of 58
$3,075,000
6

Beds

4.2

Baths

6,437

Sq.Ft.

67 High Meadow Road

Winhall, VT

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Courtesy of WOHLER REALTY GROUP
View 25 Mountain Haunts Road Winhall, VT MLS# 5029450
Save 25 Mountain Haunts Road Winhall, VT MLS# 5029450
1 of 56
$2,999,000
6

Beds

6.1

Baths

6,650

Sq.Ft.

25 Mountain Haunts Road

Winhall, VT

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Courtesy of WOHLER REALTY GROUP
View 230 School Street Bennington, VT MLS# 5058163
Save 230 School Street Bennington, VT MLS# 5058163
1 of 21
$2,950,000
75,000

Sq.Ft.

230 School Street

Bennington, VT

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Courtesy of TPW REAL ESTATE
View 23 Valley View Road Winhall, VT MLS# 5053750
Save 23 Valley View Road Winhall, VT MLS# 5053750
1 of 59
$2,800,000
3

Beds

3.1

Baths

3,938

Sq.Ft.

23 Valley View Road

Winhall, VT

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Courtesy of WOHLER REALTY GROUP
View 384 Riverbend Drive Manchester, VT MLS# 5072981
Save 384 Riverbend Drive Manchester, VT MLS# 5072981
1 of 60
$2,750,000
4

Beds

7.1

Baths

8,586

Sq.Ft.

384 Riverbend Drive

Manchester, VT

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Courtesy of JOSIAH ALLEN REAL ESTATE, INC.
View 00 VT Route 11 Peru, VT MLS# 5072898
Save 00 VT Route 11 Peru, VT MLS# 5072898
1 of 14
$2,500,000
Studio

Beds

0.0

Baths

00 VT Route 11

Peru, VT

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Courtesy of FOUR SEASONS SOTHEBY'S INT'L REALTY
View 3912 Main Street Manchester, VT MLS# 5046338
Save 3912 Main Street Manchester, VT MLS# 5046338
1 of 26
$2,495,000
9,094

Sq.Ft.

3912 Main Street

Manchester, VT

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Courtesy of TPW REAL ESTATE
View Lot 6 Stone Lodge Road Winhall, VT MLS# 5076149
  • Recently Listed
Save Lot 6 Stone Lodge Road Winhall, VT MLS# 5076149
1 of 11
$2,425,000
4

Beds

3.1

Baths

4,536

Sq.Ft.

Lot 6 Stone Lodge Road

Winhall, VT

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Courtesy of WOHLER REALTY GROUP
View 215 VT Route 30 Dorset, VT MLS# 5056222
Save 215 VT Route 30 Dorset, VT MLS# 5056222
1 of 43
$2,300,000
Studio

Beds

0.0

Baths

215 VT Route 30

Dorset, VT

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Courtesy of WOHLER REALTY GROUP
View 288 Cedar Lane Peru, VT MLS# 5061819
Save 288 Cedar Lane Peru, VT MLS# 5061819
1 of 56
$2,300,000
9

Beds

6.2

Baths

5,512

Sq.Ft.

288 Cedar Lane

Peru, VT

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Courtesy of CUMMINGS & CO

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 2/26/2026”

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