Our Stratton Luxury Listings

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Scroll down to search all Southern Vermont luxury homes for sale brokered by our expert agents. All homes and condos are listed at more than $1 million and offer some wonderful features.

Stratton Area Luxury Real Estate

Price Low to High

$1,295,000

Jamaica, VT

4427 West Hill Road South

5 Beds
4 Baths
11.12 Acres
3,040 SqFt
62 Days on Market

MLS#: 5090616

$1,475,000

Jamaica, VT

691 Black Bear Road

2 Beds
2 Baths
199.73 Acres
1,601 SqFt
36 Days on Market

MLS#: 5095401

New Listing

$1,500,000

Jamaica, VT

251 Pratt Bridge Road

7 Beds
8 Baths
16.05 Acres
8,364 SqFt
23 Days on Market

MLS#: 5097566

Active Under Contract

$2,250,000

Stratton, VT

9 Mountain Reach Mews Road, Unit 9

3 Beds
4 Baths
2,824 SqFt
41 Days on Market

MLS#: 5094589

$2,300,000

Springfield, VT

55 Cherry Hill

6 Beds
5 Baths
2 Acres
8,656 SqFt
63 Days on Market

MLS#: 5090495

$2,495,000

Dorset, VT

3039 Route 30

4 Beds
6 Baths
6 Acres
4,506 SqFt
65 Days on Market

MLS#: 5089828

$4,500,000

Stratton, VT

24 Sawmill Road

5 Beds
6 Baths
1.6 Acre
5,700 SqFt
36 Days on Market

MLS#: 5095419

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

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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 23, 2026 10:24 PM EDT