$565,000 Under Contract
- 4 Beds
- 2.5 Baths
- 2,149 Sq Ft
66 Hilltop Rd, Londonderry, VT 05155
Alison Cummings
Cummings & Co
(802) 553-3290
$565,000 Under Contract
66 Hilltop Rd, Londonderry, VT 05155
Alison Cummings
Cummings & Co
(802) 553-3290
$2,000 per month
13 Winhall Hollow Rd, Winhall, VT 05340
Amazing Location!! This recently renovated home (2023) offers modern comfort in a quiet, wooded setting just minutes to Stratton Mountain. With 2.5 bedrooms, a full kitchen, and living spaces on both floors, it's an ideal year-roundresidence or seasonal ski retreat.The main bedrooms are spacious and bright, while the additional "half" bedroom features built-in bunks andlaundry perfect
Sandy Laserte Berkshire Hathaway HomeServices Stratton Home
$125,000 Sold Dec 11, 2025
0 Dalewood Rd Unit 4955807, Jamaica, VT 05343
Last Sold Summary
Last Listing Agent Mike England Michael England Real Estate
0 Dalewood Rd Unit 4955807, Jamaica, VT 05343Est $609,780 Not Listed For Sale
78 Middle Ridge Rd Unit 102, Stratton, VT 05155
78 Middle Ridge Rd Unit 102, Stratton, VT 05155$75,000
92 Founders Hill Rd Unit 5A, Stratton, VT 05340
Trent Stephens
Wohler Realty Group
(802) 521-2464
$10,000 per month
37 Burnt Hill Rd, Winhall, VT 05340
MARCH 2026 ONLY. Location, Stratton ski shuttle, style, and so much space: Welcome to your mountain home! This luxurious Strattonwald home offers bedrooms for the whole crew, plus loads of living space, light, a well-equipped, gourmet kitchen for cooking and entertaining, and a hot tub for après-ski memories. It is well-built, lovingly cared-for, and a rare opportunity to rent for just one month
Jamie Luke TPW Real Estate
$340,000 Sold Aug 14, 2025
290 Melendy Hill Rd, South Londonderry, VT 05155
Last Sold Summary
Current Estimated Value $344,695
Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home
290 Melendy Hill Rd, South Londonderry, VT 05155Est $499,370 Not Listed For Sale
476 Edie Ln, Jamaica, VT 05343
476 Edie Ln, Jamaica, VT 05343$275,000
0 W Hill Rd, Jamaica, VT 05343
0 W Hill Rd, Jamaica, VT 05343$18,000 per month
67 Vermont Route 100, Jamaica, VT 05155
Discover the charm of this delightful rental nestled along a quintessential river in Vermont! With its prime location on a major road, you're just 7 miles away from the slopes of the Stratton Mountain ski resort, making it the perfect getaway for winter sports enthusiasts. This spacious home boasts multiple living areas, ensuring everyone has their own space to relax and unwind. With four
Sandy Laserte Berkshire Hathaway HomeServices Stratton Home
$200,000 Sold Oct 17, 2025
533 Pratt Bridge Rd, Jamaica, VT 05343
Last Sold Summary
Last Listing Agent Mike England Michael England Real Estate
533 Pratt Bridge Rd, Jamaica, VT 05343Not Listed For Sale
30 Styles Branch Rd Unit 307, Stratton, VT 05360
30 Styles Branch Rd Unit 307, Stratton, VT 05360$495,000
0 W Hill Rd, Jamaica, VT 05343
0 W Hill Rd, Jamaica, VT 05343$35,000 per month
2 Aspen Ln, Winhall, VT 05340
*Available for a partial season discount.* Stratton views, sunlight, space, and location: this ski chalet has it all! The open floor plan of the main level brings everyone together around the spacious kitchen, dining area, and living room, under a vaulted cathedral ceiling and with a wall of windows overlooking the forest below and Stratton's peak ahead. Front deck offers dining area and a grill
Jamie Luke TPW Real Estate
$700,000 Sold Jul 21, 2025
40 Founders Hill Rd, Stratton, VT 05360
Last Sold Summary
Current Estimated Value $706,547
Last Listing Agent Margretta Fischer Wohler Realty Group
40 Founders Hill Rd, Stratton, VT 05360Not Listed For Sale
30 Styles Branch Rd Unit 309, Stratton, VT 05360
30 Styles Branch Rd Unit 309, Stratton, VT 05360$195,000
0 W Hill Rd, Jamaica, VT 05343
0 W Hill Rd, Jamaica, VT 05343$40,000 per month
1303 Goodaleville Rd, South Londonderry, VT 05155
Stunning expansive farmhouse ready for your winter enjoyment. Just ten minutes from Stratton's access road entrance . Located on a beautiful country road. 5 attractive bedrooms , 3 full baths, 2 half baths. Yoga room. Sauna. Wood burning fireplace. Garage. This decorator appointed home is the perfect winter vacation respite for you and your family and friends. Utilities , Owners's
Terry Hill Berkshire Hathaway HomeServices Stratton Home
$750,000 Sold Aug 14, 2025
573 Middletown Rd, Londonderry, VT 05148
Last Sold Summary
Current Estimated Value $724,802
Last Listing Agent Bob Maisey Berkshire Hathaway HomeServices Stratton Home
573 Middletown Rd, Londonderry, VT 05148Not Listed For Sale
12 Stratton Rd W Unit 12, Winhall, VT 05340
12 Stratton Rd W Unit 12, Winhall, VT 05340$650,000
0 W Hill Rd, Jamaica, VT 05343
0 W Hill Rd, Jamaica, VT 05343$5,800 per month
8 Rocky Rd, Winhall, VT 05340
Located in one of the most sought-after spots in the area. This three-bedroom "mid-century vibed" beauty is just a 10-minute drive to the Stratton Access Road and a 12-minute drive to Manchester. Bromley is literally around the corner and Magic is a quick 15-minute drive.There is a beautiful stream in the backyard that adds additional "802" ambiance to the property. Truly a peaceful setting
Peggy O'neill Cummings & Co
$640,000 Sold Apr 25, 2025
13 Winhall Station Rd, Londonderry, VT 05155
Last Sold Summary
Current Estimated Value $637,532
Last Listing Agent Julie Lowe Lowe's Real Estate, LLC
13 Winhall Station Rd, Londonderry, VT 05155Not Listed For Sale
43 High Point Dr Unit D23, Stratton, VT 05360
43 High Point Dr Unit D23, Stratton, VT 05360$1,750,000
148 Sunbowl Ridge Rd Unit 148B, Stratton, VT 05360
Andrew King Stratton Real Estate
$28,000 per month
35 Strattonwald Rd, Winhall, VT 05340
$28,000 Winter Rental Rate | Spend the winter in Vermont at this inviting 4-bedroom, 3-bath Strattonwald chalet, available mid-November through mid-April. Nestled among the woods yet just minutes from Stratton Mountain, this home offers a welcoming retreat and the perfect base for the ski season. The main living area features soaring vaulted ceilings and a pellet stove, creating a bright and cozy
Cheyanne Pugliese
$615,000 Sold Apr 15, 2025
29 Burnt Hill Rd, Winhall, VT 05340
Last Sold Summary
Current Estimated Value $697,506
Last Listing Agent Andie Fusco Four Seasons Sotheby's Int'l Realty
29 Burnt Hill Rd, Winhall, VT 05340Not Listed For Sale
27 Mountain View Rd, Winhall, VT 05360
27 Mountain View Rd, Winhall, VT 05360$995,000
56 Shattarack Rd Unit D6, Stratton, VT 05360
Kim Morgan-Wohler Wohler Realty Group
$2,500 per month
4591 Vermont 30, Jamaica, VT 05343
ITS NOT TOO LATE.. SNOW IS JUST STARTING TO FLY..This is a delightful Winter retreat...After a long fun day of skiing come home to this warm and cozy, meticulously maintained 4 bedroom home that is in great shape. Just 8 minutes from Stratton access Rd.Upstairs there are 2.5 bedrooms , kitchen, and living room with wood burning fireplace. Downstairs is another full bedroom and a 2nd kitchen,
Wilkie Bushby TPW Real Estate
$122,500 Sold Apr 18, 2025
10 Little Brook Rd, Winhall, VT 05340
Last Sold Summary
Current Estimated Value $125,886
Last Listing Agent Lauren Behm Berkshire Hathaway HomeServices Stratton Home
10 Little Brook Rd, Winhall, VT 05340Not Listed For Sale
6 Black Birch Rd, Winhall, VT 05340
6 Black Birch Rd, Winhall, VT 05340$430,000
8 Silver Birch Rd Unit 8, Winhall, VT 05340
Lauren Behm Berkshire Hathaway HomeServices Stratton Home
$30,000 per month
90 Turkey Run Rd, Winhall, VT 05340
Intervale Rental. Available for the winter 25-26 winter season. Also available for summer or fall monthly rental. Entry mud room for boot storage. Main floor has wood burning fire place, and the deck off the living room is a overlooks the pond. Main floor has primary suite. Two bedrooms plus a sleeping loft on the upper floor. One bedroom has an en suite bathroom, and a hallway full bathroom
Christiane Carroccio TPW Real Estate
$375,000 Sold May 05, 2025
61 Birch Hill Rd Unit 6, Winhall, VT 05340
Last Sold Summary
Last Listing Agent Christiane Carroccio TPW Real Estate
61 Birch Hill Rd Unit 6, Winhall, VT 05340Est $660,330 Not Listed For Sale
78 Middle Ridge Rd Unit 106, Stratton, VT 05155
78 Middle Ridge Rd Unit 106, Stratton, VT 05155$1,760,000
89 Sunbowl Ridge Rd Unit 89A, Stratton, VT 05360
Edwin Kevil Stratton Real Estate
$692,000 Sold Oct 03, 2025
19 Village Lodge Rd Unit 207, Stratton, VT 05155
Last Sold Summary
Last Listing Agent Kim Morgan-Wohler Wohler Realty Group
19 Village Lodge Rd Unit 207, Stratton, VT 05155Est $266,509 Not Listed For Sale
765 Thompsonburg Rd, South Londonderry, VT 05155
765 Thompsonburg Rd, South Londonderry, VT 05155$1,725,000
122 Sunbowl Ridge Rd, Stratton, VT 05360
John Sikes Stratton Real Estate
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