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Winhall, VT

Stratton Area Homes for Sale

177Results

View all residential listings in the Stratton area of Southern Vermont and find a variety of beautiful homes to explore.

Homes for Sale in Southern Vermont

Contact Winhall Real Estate at 802-297-1550 or online if you're interested in a particular property or have any questions.

Price High to Low
24 Sawmill Road Stratton VT 05155

$4,500,000

Stratton, VT

24 Sawmill Road

  • 5 Beds
  • 6 Baths
  • 1.6 Acre
  • 5,700 SqFt
  • 34 Days on Market
MLS#: 5095419

$2,495,000

Dorset, VT

3039 Route 30

  • 4 Beds
  • 6 Baths
  • 6 Acres
  • 4,506 SqFt
  • 63 Days on Market
MLS#: 5089828
New Listing

$1,500,000

Jamaica, VT

251 Pratt Bridge Road

  • 7 Beds
  • 8 Baths
  • 16.05 Acres
  • 8,364 SqFt
  • 21 Days on Market
MLS#: 5097566

$1,475,000

Jamaica, VT

691 Black Bear Road

  • 2 Beds
  • 2 Baths
  • 199.73 Acres
  • 1,601 SqFt
  • 34 Days on Market
MLS#: 5095401

$1,295,000

Jamaica, VT

4427 West Hill Road South

  • 5 Beds
  • 4 Baths
  • 11.12 Acres
  • 3,040 SqFt
  • 60 Days on Market
MLS#: 5090616
New Listing

$775,000

Winhall, VT

12 Stratton Ridge Road

  • 4 Beds
  • 4 Baths
  • 2.39 Acres
  • 3,520 SqFt
  • 25 Days on Market
MLS#: 5097091
Open House

$645,000

Londonderry, VT

1161 Little Pond Road

NEXT OPEN HOUSE:

Sun 7/26 11:00 AM to 1:00 PM

  • 4 Beds
  • 3 Baths
  • 0.42 Acres
  • 2,740 SqFt
  • 6 Days on Market
MLS#: 5100212

$625,000

Winhall, VT

1 Beaver Street

  • 3 Beds
  • 2 Baths
  • 1.05 Acre
  • 2,288 SqFt
  • 40 Days on Market
MLS#: 5094344

$595,000

Jamaica, VT

9 Mountain Acres Road

  • 4 Beds
  • 2 Baths
  • 0.7 Acres
  • 1,430 SqFt
  • 63 Days on Market
MLS#: 5089830
New Listing

$549,000

Londonderry, VT

202 Twin Brook Circle

  • 4 Beds
  • 3 Baths
  • 1.54 Acre
  • 1,936 SqFt
  • 29 Days on Market
MLS#: 5096153
Active Under Contract

$495,000

Winhall, VT

140 Route 30

  • 4 Beds
  • 2 Baths
  • 0.4 Acres
  • 1,824 SqFt
  • 55 Days on Market
MLS#: 5091404
New Listing

$480,000

Jamaica, VT

3327 Route 30

  • 5 Beds
  • 2 Baths
  • 1.25 Acre
  • 2,194 SqFt
  • 21 Days on Market
MLS#: 5097573

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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 July 21, 2026 10:54 PM EDT