Winhall, VT Homes

/29
$699,000 Under Contract
- 3 Beds
- 3 Baths
- 2,317 Sq Ft
9 F Cobble Ridge Rd, Winhall, VT 05340

Step into a lifestyle of luxury and convenience at Piper Ridge D9! This stunning community offers the perfect blend of comfort and excitement, with fantastic amenities like a sparkling swimming pool, tennis courts, a clubhouse for social gatherings, and even a weekend shuttle service in the winter—ideal for enjoying the nearby slopes! Inside the impeccably maintained townhouse, you'll find a cozy

Carrie Mathews Winhall Real Estate

9 F Cobble Ridge Rd, Winhall, VT 05340
/22
$445,000 Sold Sep 16, 2025

163 Vt Route 30, Winhall, VT 05340
- 3 Beds
- 2 Baths
- 1,590 Sq Ft
- Built 1970
Last Sold Summary
- 1% Below List Price
- $280/SF
- 13 Days On Market
Current Estimated Value $449,583

Last Listing Agent Timothy Apps Four Seasons Sotheby's Int'l Realty

163 Vt Route 30, Winhall, VT 05340

/31
Not Listed For Sale

71 Todd Hill Rd, Jamaica, VT 05343
- 5 Beds
- 5.5 Baths
- 3,624 Sq Ft
- Built 2006
71 Todd Hill Rd, Jamaica, VT 05343

Last Sold Summary
- $635/SF
- 4 Days On Market
- Last Sold Price $2,300,000
- Apr 05, 2024
Last Listing Agent Kevin Moran Four Seasons Sotheby's Int'l Realty

/12
$299,999
- Land
- 10.05 Acres
- $29,851 per Acre
00 Garden Loop Rd, Winhall, VT 05340

The largest remaining vacant lot on the Stratton Mountain access road. Ten acres deeded for one magnificent home. The lot is wooded with some clearing on the east side. There's a roughed-in driveway here too, making it the best spot for construction. In the center of the property is a small pond--about a tenth of an acre--and west of that a scenic perennial creek winds its way downhill along the

David White OwnerEntry.com

00 Garden Loop Rd, Winhall, VT 05340
/2
$205,000 Sold Sep 15, 2025

24 Stratton Rd W, Winhall, VT 05340
- 2 Beds
- 1 Bath
- 665 Sq Ft
- Built 1970
Last Sold Summary
- $308/SF
- 0 Days On Market
Current Estimated Value $209,196

Last Listing Agent Cheyanne Pugliese

24 Stratton Rd W, Winhall, VT 05340

/10
Not Listed For Sale

Lot 44 Moose Hollow Rd, Winhall, VT 05340
Lot 44 Moose Hollow Rd, Winhall, VT 05340

Last Sold Summary
- 114 Days On Market
- Last Sold Price $64,000
- Mar 12, 2025
Last Listing Agent Tatsiana Clark Four Seasons Sotheby's Int'l Realty

/39
$895,000 Under Contract
- 4 Beds
- 4 Baths
- 2,673 Sq Ft
F2 Cobble Ridge Rd Unit F2, Winhall, VT 05340

Own your piece of Piper Ridge, a prestigious condo complex, in Stratton, Vermont. This 4-bedroom, 4-bathroom townhome received significant improvements over the past two years, making it move-in ready for maximum relaxation in the mountains. This spacious open floor plan has been upgraded with new hardwood flooring on the first and second floors and kitchen renovations with new countertops and

Mike England Michael England Real Estate

F2 Cobble Ridge Rd Unit F2, Winhall, VT 05340
/53
$775,000 Sold Aug 13, 2025

E12 Rock Ridge Rd, Winhall, VT 05155
- 3 Beds
- 3 Baths
- 1,842 Sq Ft
- Built 1986
Last Sold Summary
- 3% Below List Price
- $421/SF
- 7 Days On Market
Last Listing Agent Cheyanne Pugliese

E12 Rock Ridge Rd, Winhall, VT 05155

/52
Not Listed For Sale

E11 Rock Ridge Rd, Winhall, VT 05155
- 3 Beds
- 3 Baths
- 2,300 Sq Ft
- Built 1986
E11 Rock Ridge Rd, Winhall, VT 05155

Last Sold Summary
- $348/SF
- 47 Days On Market
- Last Sold Price $800,000
- Feb 13, 2025
Last Listing Agent Terry Hill Berkshire Hathaway HomeServices Stratton Home

/8
$150,000
- Land
- 2.26 Acres
- $66,372 per Acre
0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340

Welcome to the Stratton Gardens Community. Build your Vermont home on this 2+ acre parcel in Stratton Gardens. Ease of access right off the Stratton Mountain Access Road, and all the amenities of Stratton Gardens Association- highlights include-Private Shuttle Bus service to the Mountain, Road Maintenance, Plowing, Landscaping, and Trash removal.State Waste Water Permit in place for approved

Tara van de Velde Four Seasons Sotheby's Int'l Realty

0 Stratton Gardens Rd Unit 5072896, Winhall, VT 05340
/2
$400,000 Sold Mar 09, 2026

97 N Branch Rd, Winhall, VT 05155
- Land
- 1.18 Acres
- $338,983 per Acre
Last Sold Summary
- 11% Below List Price
- 29 Days On Market
Last Listing Agent John Sikes Stratton Real Estate

97 N Branch Rd, Winhall, VT 05155

/55
Est $894,422 Not Listed For Sale

45 Hilltop Rd, Winhall, VT 05340
- 5 Beds
- 4 Baths
- 2,900 Sq Ft
- Built 1996
45 Hilltop Rd, Winhall, VT 05340

Last Sold Summary
- 1% Below List Price
- $310/SF
- 7 Days On Market
- Last Sold Price $899,000
- Jan 13, 2025
Last Listing Agent Terry Hill Berkshire Hathaway HomeServices Stratton Home

/34
$579,000
- 3 Beds
- 2 Baths
- 1,455 Sq Ft
4 Pearl Buck Dr, Winhall, VT 05340

Just minutes from the slopes of Stratton Mountain Resort, this three bedroom plus den, two bath home offers an easy four season retreat with stunning views of Stratton Mountain. Set on 2 acres, it gives you convenient access to everything the area is known for, from winter ski days to summer mountain biking, golf, hiking, and village events. The home has been thoughtfully improved over time,

Andie Fusco Four Seasons Sotheby's Int'l Realty

4 Pearl Buck Dr, Winhall, VT 05340
/22
$265,500 Sold Jul 15, 2025

18 Stratton Ridge Rd, Winhall, VT 05340
- 3 Beds
- 2 Baths
- 1,332 Sq Ft
- Built 1970
Last Sold Summary
- 16% Below List Price
- $199/SF
- 72 Days On Market
Last Listing Agent Derek Greene Derek Greene

18 Stratton Ridge Rd, Winhall, VT 05340

/35
Est $584,269 Not Listed For Sale

20 Deep Woods Cir, Winhall, VT 05255
- 3 Beds
- 2 Baths
- 1,592 Sq Ft
- Built 2005
20 Deep Woods Cir, Winhall, VT 05255

Last Sold Summary
- 1% Above List Price
- $364/SF
- 8 Days On Market
- Last Sold Price $580,000
- Oct 21, 2024
Last Listing Agent Sara Buckley Josiah Allen Real Estate, Inc.

/41
$950,000
- 4 Beds
- 3.5 Baths
- 3,031 Sq Ft
7 Roundtree Rd, Winhall, VT 05340

Discover the perfect mountain retreat at 7 Roundtree Road, a contemporary and beautifully designed 4-bedroom home set on 1.37 private acres in one of Stratton’s most sought-after neighborhoods. Ideally located just a quick drive to the Base Lodge—or simply hop on the convenient shuttle for effortless access to the slopes—this property offers the best of Stratton living in every season.Step

Bob Maisey Berkshire Hathaway HomeServices Stratton Home

7 Roundtree Rd, Winhall, VT 05340
/46
$1,270,000 Sold Mar 20, 2026

33 Forest Haunts Rd, Winhall, VT 05340
- 4 Beds
- 4 Baths
- 4,640 Sq Ft
- Built 1989
Last Sold Summary
- 15% Below List Price
- $274/SF
- 487 Days On Market
Current Estimated Value $1,335,445

Last Listing Agent Timothy Apps Four Seasons Sotheby's Int'l Realty

33 Forest Haunts Rd, Winhall, VT 05340

/30
Not Listed For Sale

20 Maple Beech Rd Unit 20, Winhall, VT 05340
- 3 Beds
- 3 Baths
- 1,650 Sq Ft
- Built 1984
20 Maple Beech Rd Unit 20, Winhall, VT 05340

Last Sold Summary
- $333/SF
- 4 Days On Market
- Last Sold Price $550,000
- Oct 03, 2024
Last Listing Agent Christiane Carroccio TPW Real Estate

/32
$695,000 Pending
- 5 Beds
- 3.5 Baths
- 2,888 Sq Ft
22 Sylvan Ridge Rd, Winhall, VT 05340

Renovated Manchester Mountain VT Retreat, located just minutes from Bromley, Stratton and Manchester, your perfect year-round Vermont vacation home awaits. With 3 levels and an entertain room on each, this home is extremely comfortable for large groups to gather and enjoy. The kitchen, dining room, primary en-suite bedroom, and powder room and rear deck are all located on the main level

Jason Saphire www.HomeZu.com

22 Sylvan Ridge Rd, Winhall, VT 05340
/32
$350,000 Sold Mar 20, 2026

44 Lake Rd, Bondville, VT 05340
- 5 Beds
- 3 Baths
- 2,303 Sq Ft
- Built 1976
Last Sold Summary
- 22% Below List Price
- $152/SF
- 5 Days On Market
Current Estimated Value $448,702

Last Listing Agent Timothy Apps Four Seasons Sotheby's Int'l Realty

44 Lake Rd, Bondville, VT 05340

/25
Not Listed For Sale

0 Cobble Ridge Rd Unit D2, Winhall, VT 05340
- 4 Beds
- 3 Baths
- 2,317 Sq Ft
- Built 1988
0 Cobble Ridge Rd Unit D2, Winhall, VT 05340

Last Sold Summary
- $356/SF
- 135 Days On Market
- Last Sold Price $825,000
- Mar 14, 2025
Last Listing Agent Jamie Wylie Stratton Real Estate

/15
$825,000
- Land
- 77.6 Acres
- $10,631 per Acre
0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340

Large wooded parcel located in the heart of Southern Vermont’s ski country, just minutes from Stratton Mountain. This undeveloped Winhall property offers a rare opportunity for a variety of potential uses, from a private estate to recreational land or possible future development. The land consists primarily of wooded acreage with a gently rolling landscape and natural Vermont forest. Located on

Trent Stephens Wohler Realty Group

0 Winhall Hollow Rd Unit 5079556, Bondville, VT 05340
/26
$795,000 Sold Aug 21, 2025

5 Founders Hill Rd, Winhall, VT 05360
- 3 Beds
- 3 Baths
- 1,624 Sq Ft
- Built 1970
Last Sold Summary
- $490/SF
- 0 Days On Market
Last Listing Agent Jamie Wylie Stratton Real Estate

5 Founders Hill Rd, Winhall, VT 05360

/30
Est $672,837 Not Listed For Sale

6 Golden Triangle Rd, Winhall, VT 05340
- 3 Beds
- 3 Baths
- 1,680 Sq Ft
- Built 2004
6 Golden Triangle Rd, Winhall, VT 05340

Last Sold Summary
- 11% Above List Price
- $360/SF
- 10 Days On Market
- Last Sold Price $605,000
- Oct 08, 2024
Last Listing Agent TG Glazer Winhall Real Estate

/13
$135,000 Under Contract
- Land
- 1.36 Acres
- $99,265 per Acre
0 Stratton View Rd Unit 14, Winhall, VT 05340

Stratton View Road lives up to its name. Big Views of Stratton, just 3 minutes to Stratton access road. Minutes to the snow making pond, great for walking and a dip in. the summer. There are 3 ski resorts with in 15 minutes as well as Manchester for shopping and dining. Own your piece of Vermont.

Mike England Michael England Real Estate

0 Stratton View Rd Unit 14, Winhall, VT 05340
/22
$389,000 Sold Feb 23, 2026

2 Lower Stratton Valley Rd, Winhall, VT 05340
- 4 Beds
- 1.5 Baths
- 1,344 Sq Ft
- Built 1978
Last Sold Summary
- $289/SF
- 26 Days On Market
Current Estimated Value $402,301

Last Listing Agent Mike Masters Four Seasons Sotheby's Int'l Realty

2 Lower Stratton Valley Rd, Winhall, VT 05340

/32
Not Listed For Sale

1 Silver Birch Rd, Winhall, VT 05340
- 3 Beds
- 2 Baths
- 1,215 Sq Ft
- Built 1968
1 Silver Birch Rd, Winhall, VT 05340

Last Sold Summary
- $309/SF
- 61 Days On Market
- Last Sold Price $375,000
- Nov 25, 2024
Last Listing Agent Robin Apps Four Seasons Sotheby's Int'l Realty

/33
$1,650,000 Pending
- 4 Beds
- 3.5 Baths
- 2,813 Sq Ft
264 French Hollow Rd, Bondville, VT 05340

Step into this newly constructed 2022 residence offering a rare sense of elevation—both literal and figurative—without sacrificing ease of access. While the home feels perched above it all, it is reached via a gentle sloping driveway, providing everyday convenience alongside breathtaking views. Sweeping, uninterrupted vistas are enjoyed from nearly every room, creating a constant connection to

Kristin Pirie Winhall Real Estate

264 French Hollow Rd, Bondville, VT 05340
/49
$705,000 Sold Jan 06, 2026

A6 Ridge Unit A6, Winhall, VT 05340
- 4 Beds
- 3 Baths
- 2,118 Sq Ft
- Built 1982
Last Sold Summary
- 12% Below List Price
- $333/SF
- 225 Days On Market
Last Listing Agent Karin Hardy Berkshire Hathaway HomeServices Stratton Home

A6 Ridge Unit A6, Winhall, VT 05340

/60
Est $896,497 Not Listed For Sale

53 Stratton View Rd, Bondville, VT 05340
- 4 Beds
- 3.5 Baths
- 3,772 Sq Ft
- Built 1989
53 Stratton View Rd, Bondville, VT 05340

Last Sold Summary
- 10% Above List Price
- $217/SF
- 30 Days On Market
- Last Sold Price $817,500
- Dec 13, 2024
Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

/27
$609,000
- 4 Beds
- 3 Baths
- 1,650 Sq Ft
60 Hilltop Rd Unit 60, Winhall, VT 05340

Turn-key Stratton retreat in one of the area’s most desirable year-round communities. This 4-bedroom, 3-bath Intervale townhome offers the perfect blend of comfort and convenience—just minutes to the slopes with seasonal shuttle service right from the community. The open-concept living area is ideal for gathering after a day on the mountain, while five mini-split systems provide efficient heating

Timothy Apps Four Seasons Sotheby's Int'l Realty

60 Hilltop Rd Unit 60, Winhall, VT 05340
/30
$330,000 Sold May 09, 2025

21 Stratton Ridge Rd, Winhall, VT 05340
- 3 Beds
- 1.5 Baths
- 1,088 Sq Ft
- Built 1970
Last Sold Summary
- 13% Below List Price
- $303/SF
- 115 Days On Market
Last Listing Agent Andie Fusco Four Seasons Sotheby's Int'l Realty

21 Stratton Ridge Rd, Winhall, VT 05340

/40
Est $891,838 Not Listed For Sale

36 Road To Millbrook, Winhall, VT 05340
- 4 Beds
- 3.5 Baths
- 3,119 Sq Ft
- Built 1996
36 Road To Millbrook, Winhall, VT 05340

Last Sold Summary
- 5% Above List Price
- $273/SF
- 168 Days On Market
- Last Sold Price $850,000
- Apr 04, 2025
Last Listing Agent Timothy Apps Four Seasons Sotheby's Int'l Realty

/15
$500,000
- Land
- 21.2 Acres
- $23,585 per Acre
56 Lower Taylor Hill Rd, Winhall, VT 05340

A rare opportunity to create a private Vermont retreat on 21.2 +/- acres along Lower Taylor Hill Road in Winhall. The property is supported by a State-approved wastewater permit for a six (6) bedroom single-family residence, offering flexibility to design a substantial home within permitted limits. Rolling terrain, natural clearings, and mature woodland provide multiple potential building sites,

Kevin Moran Four Seasons Sotheby's Int'l Realty

56 Lower Taylor Hill Rd, Winhall, VT 05340
/38
$779,000 Sold Oct 31, 2025

44 Hilltop Rd, Winhall, VT 05340
- 4 Beds
- 4 Baths
- 2,997 Sq Ft
- Built 1996
Last Sold Summary
- 1% Below List Price
- $260/SF
- 22 Days On Market
Current Estimated Value $799,193

Last Listing Agent Christiane Carroccio TPW Real Estate

44 Hilltop Rd, Winhall, VT 05340

/14
Not Listed For Sale

00 Kendall Farm To Black Cherry Ridge Rd, Winhall, VT 05340
00 Kendall Farm To Black Cherry Ridge Rd, Winhall, VT 05340

Last Sold Summary
- 120 Days On Market
- Last Sold Price $210,000
- Sep 20, 2024
Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

/55
$950,000
- 5 Beds
- 4.5 Baths
- 2,321 Sq Ft
24 N Branch Rd, Winhall, VT 05340

Location says it all ! Stratton Quarter Mile neighborhood on Shuttle, just a short walk home from the Village. This exceptional renovation offers an expanded floor plan with a third level.Beautiful upscale baths with tile work and craftsmanship of the highest caliber. Wood floors throughout. Open gourmet kitchen makes for premier apres ski gatherings. With 5 bedrooms/4 baths and multiple ensuite-

Kim Morgan-Wohler Wohler Realty Group

24 N Branch Rd, Winhall, VT 05340
/2
$815,000 Sold Mar 05, 2026

B15 Maple Ridge Rd Unit B15, Winhall, VT 05340
- 4 Beds
- 3 Baths
- 2,500 Sq Ft
- Built 1985
Last Sold Summary
- 1% Above List Price
- $326/SF
- 0 Days On Market
Last Listing Agent Andrew King Stratton Real Estate

B15 Maple Ridge Rd Unit B15, Winhall, VT 05340

/11
Not Listed For Sale

E3 Nearing Rd, Winhall, VT 05340
E3 Nearing Rd, Winhall, VT 05340

Last Sold Summary
- 212 Days On Market
- Last Sold Price $160,000
- Mar 19, 2025
Last Listing Agent Britt Wohler

/6
$99,000
- Land
- 1 Acre
- $99,000 per Acre
88A Sylvan Ridge Rd, Winhall, VT 05340

Wooded lot with hardwoods, evergreens and birch trees. Potential views of Bromley Mountain and beyond. Town maintained road. Close to VAST snowmobile trails. Build your dream home in the Golden Triangle of ski areas, Stratton, Bromley, and Magic Mountains. Only 10 minuets to Manchester. Available on request:Wastewater System and Potable Water Supply PermitSeptic Site PlanCovenants

Andrew King Stratton Real Estate

88A Sylvan Ridge Rd, Winhall, VT 05340

Showing Results 81 - 120, Page 3 of 18

Vermont Bennington County Winhall

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