Bennington Vermont Homes for Sale

279 total properties
View 551 West Fields Road Manchester, VT MLS# 5052301
  • New Construction with Virtual Tour
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
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
$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
$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
$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
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
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
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
$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
$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
$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
$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
$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
$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
$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
$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
$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
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
$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
$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

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“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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