Winhall, VT Homes

/37
$999,000
- 4 Beds
- 3.5 Baths
- 2,280 Sq Ft
17 Roundtree Rd, Winhall, VT 05340

Contemporary ski chalet on shuttle route located on a short cul-de-sac in the coveted North Brookwood neighborhood, a stone's throw from the Stratton base lodge. This 4 bedroom, 3 1⁄2 bath home boasts an open plan, walls of windows, and floor-to-ceiling stone fireplace in the Great Room. The pass-through kitchen was fully renovated in 2021 in addition to many other upgrades. Test your skills at

Sarah Nichols Winhall Real Estate

17 Roundtree Rd, Winhall, VT 05340
/41
$1,150,000 Sold Jul 25, 2025

35 Old Ridge Rd, Winhall, VT 05155
- 4 Beds
- 5.5 Baths
- 4,826 Sq Ft
- Built 1997
Last Sold Summary
- 38% Below List Price
- $238/SF
- 369 Days On Market
Last Listing Agent Mike England Michael England Real Estate

35 Old Ridge Rd, Winhall, VT 05155

/29
Est $673,850 Not Listed For Sale

32 Beaver St, Bondville, VT 05340
- 4 Beds
- 2.5 Baths
- 2,179 Sq Ft
- Built 2008
32 Beaver St, Bondville, VT 05340

Last Sold Summary
- 1% Above List Price
- $307/SF
- 7 Days On Market
Last Sold Price $668,000

Last Listing Agent Jamie Wylie Stratton Real Estate

/39
$735,000 Under Contract
- 4 Beds
- 3 Baths
- 2,091 Sq Ft
5 Wall St, Bondville, VT 05340

While temperatures outside may be freezing, step inside and take in the incredible views of Stratton while basking in sunlight from the living room of this Vermont home. Located just one mile from the base of the Stratton Access Road and only 20 minutes from Manchester, the setting offers exceptional convenience while remaining peacefully tucked away in the private woods of Winhall. The main

Cheyanne Pugliese

5 Wall St, Bondville, VT 05340
/43
$755,000 Sold Nov 14, 2025

43 Hilltop Rd, Winhall, VT 05340
- 4 Beds
- 4 Baths
- 3,020 Sq Ft
- Built 1988
Last Sold Summary
- 2% Above List Price
- $250/SF
- 0 Days On Market
Current Estimated Value $752,401

Last Listing Agent Daniel Preston KW Vermont Woodstock

43 Hilltop Rd, Winhall, VT 05340

/31
Est $555,551 Not Listed For Sale

22 Little Brook Rd, Winhall, VT 05340
- 3 Beds
- 2 Baths
- 1,896 Sq Ft
- Built 2004
22 Little Brook Rd, Winhall, VT 05340

Last Sold Summary
- 13% Above List Price
- $258/SF
- 10 Days On Market
Last Sold Price $490,000

Last Listing Agent TG Glazer Winhall Real Estate

/59
$2,800,000
- 3 Beds
- 3.5 Baths
- 3,938 Sq Ft
23 Valley View Rd, Winhall, VT 05340

Set at the end of a long, private driveway, this remarkable property unveils dramatic panoramic vistas that stretch nearly 40 miles. Offering a rare sense of seclusion & grandeur, the home is an ideal retreat where nature, privacy, and beauty converge.Designed w/a modern aesthetic,an expansive open-concept layout, the main floor features a stunning stone fireplace , enhanced by soaring ceilings

Kim Morgan-Wohler Wohler Realty Group

23 Valley View Rd, Winhall, VT 05340
/59
$1,082,500 Sold Aug 29, 2025

4 Garden Loop Rd, Winhall, VT 05340
- 3 Beds
- 3.5 Baths
- 4,054 Sq Ft
- Built 2005
Last Sold Summary
- 10% Below List Price
- $267/SF
- 45 Days On Market
Current Estimated Value $1,110,307

Last Listing Agent Lucy Ferrada Heney Realtors - Element Real Estate (Montpelier)

4 Garden Loop Rd, Winhall, VT 05340

/40
Est $862,090 Not Listed For Sale

34 Raspberry Hill Rd, Winhall, VT 05340
- 4 Beds
- 3 Baths
- 2,872 Sq Ft
- Built 1975
34 Raspberry Hill Rd, Winhall, VT 05340

Last Sold Summary
- 6% Above List Price
- $282/SF
- 5 Days On Market
Last Sold Price $810,000

Last Listing Agent Jamie Luke TPW Real Estate

/56
$2,999,000 Under Contract
- 6 Beds
- 6.5 Baths
- 6,650 Sq Ft
25 Mountain Haunts Rd, Winhall, VT 05340

Exceptional 40.8 acre newly expanded and renovated Stratton Mountain estate with unrivaled views of Stratton just minutes from the Base Lodge or Sun Bowl. This is your own personal winter playground where you can hit the slopes or snowmobile and hike on your own land with additional acreage available.This Grand Lodge NOW BOASTS 4 ensuite bedroom, 3 stone fireplaces, huge lodge room w/ large beams

Kim Morgan-Wohler Wohler Realty Group

25 Mountain Haunts Rd, Winhall, VT 05340
/33
$740,000 Sold Jan 02, 2026

G12 Cobble Ridge Rd, Winhall, VT 05340
- 4 Beds
- 4 Baths
- 2,764 Sq Ft
- Built 1985
Last Sold Summary
- 5% Below List Price
- $268/SF
- 1 Day On Market
Current Estimated Value $728,333

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

G12 Cobble Ridge Rd, Winhall, VT 05340

/35
Est $444,436 Not Listed For Sale

383 Winhall Hollow Rd, Bondville, VT 05340
- 3 Beds
- 2 Baths
- 1,470 Sq Ft
- Built 1950
383 Winhall Hollow Rd, Bondville, VT 05340

Last Sold Summary
- 19% Above List Price
- $255/SF
- 2 Days On Market
Last Sold Price $375,000

Last Listing Agent Carrie Mathews Winhall Real Estate

/11
$2,425,000 New Construction
- 4 Beds
- 3.5 Baths
- 4,536 Sq Ft
6 Stone Lodge Rd, Winhall, VT 05340

SHOWINGS BEGIN at Thursday February 12. Premier New Construction, offering 4500+ SF of luxury living on three levels, perched on 2.5 acres to maximize panoramic mountain and Bromley views. Just minutes to the Stratton Resort Base Lodge, this exceptional 4 bedroom/3.5 bath floor plan combines contemporary design, craftsmanship of the highest caliber and energy efficiency.Thoughtfully designed for

Kim Morgan-Wohler Wohler Realty Group

6 Stone Lodge Rd, Winhall, VT 05340
/58
$975,000 Sold Nov 27, 2025

20 Jamie Ln, Winhall, VT 05340
- 5 Beds
- 3.5 Baths
- 3,500 Sq Ft
- Built 1987
Last Sold Summary
- $279/SF
- 38 Days On Market
Current Estimated Value $986,588

Last Listing Agent David Powers 42 North LP

20 Jamie Ln, Winhall, VT 05340

/25
Est $350,620 Not Listed For Sale

84 Lower Taylor Hill Rd, Winhall, VT 05340
- 4 Beds
- Built 1900
84 Lower Taylor Hill Rd, Winhall, VT 05340

Last Sold Summary
- 50% Above List Price
- $122/SF
- 4 Days On Market
Last Sold Price $233,000

Last Listing Agent Julie Lowe Lowe's Real Estate, LLC

/38
$1,095,000
- 4 Beds
- 3 Baths
- 3,252 Sq Ft
E1 Rock Ridge Rd, Winhall, VT 05155

Ideally situated near the renowned Stratton Mountain Resort and offering convenient shuttle service to the slopes, this spacious four-bedroom, three-bath ski condo is thoughtfully designed for year-round enjoyment. A true retreat for outdoor enthusiasts, the home provides effortless access to world-class skiing in the winter and outstanding hiking and mountain biking throughout the warmer months.

Christine Chovan

E1 Rock Ridge Rd, Winhall, VT 05155
/30
$717,500 Sold Feb 13, 2026

32 Cobble Ridge Rd Unit D10, Winhall, VT 05155
- 3 Beds
- 3 Baths
- 2,317 Sq Ft
- Built 1985
Last Sold Summary
- 2% Below List Price
- $310/SF
- 60 Days On Market
Last Listing Agent Elyn Bischof Berkshire Hathaway HomeServices Stratton Home

32 Cobble Ridge Rd Unit D10, Winhall, VT 05155

/15
Est $503,112 Not Listed For Sale

6 Old Snow Valley Rd, Winhall, VT 05340
- 2 Beds
- 2 Baths
- 1,416 Sq Ft
- Built 1957
6 Old Snow Valley Rd, Winhall, VT 05340

Last Sold Summary
- 98% Above List Price
- $179/SF
- 4 Days On Market
Last Sold Price $254,000

Last Listing Agent Joseph Cajzer Josiah Allen Real Estate, Manchester Branch Office

/2
$125,000
- Land
- 1.45 Acres
- $86,207 per Acre
L/O River Rd, Winhall, VT 05340

This 1.45+/- acre building lot offers a rare combination of privacy, recreation, and convenience. An approved Vermont wastewater permit for a 3-bedroom single-family home is already in place, streamlining the path toward building a year-round residence or mountain getaway. The property is located just one mile from the base of the Stratton Access Road and only twenty minutes from Manchester’s

Cheyanne Pugliese

L/O River Rd, Winhall, VT 05340
/29
$750,000 Sold May 12, 2025

12 Jamie Ln, Jamaica, VT 05343
- 4 Beds
- 3.5 Baths
- 3,084 Sq Ft
- Built 2003
Last Sold Summary
- 6% Below List Price
- $243/SF
- 82 Days On Market
Last Listing Agent Kevin Moran Four Seasons Sotheby's Int'l Realty

12 Jamie Ln, Jamaica, VT 05343

/20
Est $489,005 Not Listed For Sale

109 Sylvan Ridge Rd, Winhall, VT 05340
- 4 Beds
- 2 Baths
- 1,212 Sq Ft
- Built 1969
109 Sylvan Ridge Rd, Winhall, VT 05340

Last Sold Summary
- 19% Above List Price
- $338/SF
- 1 Day On Market
Last Sold Price $410,000

Last Listing Agent Andie Fusco Four Seasons Sotheby's Int'l Realty

/22
$375,000
- 3 Beds
- 2 Baths
- 1,344 Sq Ft
3 Kimball Hill Rd Unit 1, Winhall, VT 05340

Escape to the mountains in this charming A-frame, ideally located between the bustling town of Manchester and the area's best ski mountains. This home is your perfect base for year-round adventure, putting you just minutes from world-class skiing, hiking, mountain biking, and shopping.Inside, you'll find a comfortable layout featuring 3 bedrooms, 2 bathrooms, and a home office that can

Robin Apps Four Seasons Sotheby's Int'l Realty

3 Kimball Hill Rd Unit 1, Winhall, VT 05340
/40
$1,000,000 Sold Feb 24, 2026

19 Roundtree Rd, Bondville, VT 05340
- 4 Beds
- 2.5 Baths
- 3,086 Sq Ft
- Built 1978
Last Sold Summary
- 2% Below List Price
- $324/SF
- 80 Days On Market
Current Estimated Value $1,010,436

Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

19 Roundtree Rd, Bondville, VT 05340

/39
Est $1,028,955 Not Listed For Sale

19 Maple Hill Rd, Winhall, VT 05340
- 3 Beds
- 2.5 Baths
- 2,814 Sq Ft
- Built 1978
19 Maple Hill Rd, Winhall, VT 05340

Last Sold Summary
- 16% Below List Price
- $435/SF
- 6 Days On Market
Last Sold Price $1,225,000

Last Listing Agent Kim Morgan-Wohler Wohler Realty Group

/12
$450,000
- Land
- 10.26 Acres
- $43,860 per Acre
4.1 Pearl Buck Dr, Winhall, VT 05340

One of the last significant VIEW lots available on the mountain , with unrivaled 360 degree views, including dead on views of Stratton Mountain trails. The pinnacle of this 10.26 acre lot is deserving of an exceptionally designed and expansive home in this premium location with commanding views.Prime for a legacy property in a most desirable location, just 5 minutes to the Stratton Base Area,

Kim Morgan-Wohler Wohler Realty Group

4.1 Pearl Buck Dr, Winhall, VT 05340
/44
$702,000 Sold Oct 24, 2025

86 Benson Fuller Dr, Bondville, VT 05340
- 4 Beds
- 2 Baths
- 2,040 Sq Ft
- Built 1983
Last Sold Summary
- 6% Below List Price
- $344/SF
- 42 Days On Market
Current Estimated Value $690,903

Last Listing Agent Sandy Laserte Berkshire Hathaway HomeServices Stratton Home

86 Benson Fuller Dr, Bondville, VT 05340

/36
Est $735,511 Not Listed For Sale

11 Todd Hill Rd, Winhall, VT 05340
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
- Built 1973
11 Todd Hill Rd, Winhall, VT 05340

Last Sold Summary
- 1% Above List Price
- $403/SF
- 30 Days On Market
Last Sold Price $725,000

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

/38
$375,000
- Land
- 1.23 Acres
- $304,878 per Acre
0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340

Exceptional offering. This premier parcel defines phase II of Ravenwood, an enclave of distinctive and premier mountain residences. This notable site offers extraordinary mountain views, direct access from Winhall Hollow Road and still enjoys all the benefits and amenities of The Ravenwood Neighborhood Association. Combining, privacy, natural beauty and convenience, this well-established

Kim Morgan-Wohler Wohler Realty Group

0 Winhall Hollow Rd Unit 5073717, Bondville, VT 05340
/20
$500,000 Sold Nov 26, 2025

374 Winhall Hollow Rd, Winhall, VT 05340
- 4 Beds
- 3 Baths
- 1,920 Sq Ft
- Built 1986
Last Sold Summary
- 1% Above List Price
- $260/SF
- 3 Days On Market
Current Estimated Value $511,075

Last Listing Agent Annette Gallo Real Broker LLC

374 Winhall Hollow Rd, Winhall, VT 05340

/40
Est $841,651 Not Listed For Sale

40 Loop Rd, Winhall, VT 05340
- 3 Beds
- 3 Baths
- 2,196 Sq Ft
- Built 2006
40 Loop Rd, Winhall, VT 05340

Last Sold Summary
- 5% Above List Price
- $365/SF
- 5 Days On Market
Last Sold Price $802,000

Last Listing Agent Terry Hill Berkshire Hathaway HomeServices Stratton Home

/33
$485,000
- 3 Beds
- 1 Bath
- 1,344 Sq Ft
3 Strattonwald Rd, Winhall, VT 05340

Lovingly renovated and move-in ready, this 3-bedroom chalet is your ideal mountain escape in the sought-after Strattonwald neighborhood. Take in beautiful views of Stratton Mountain from the comfort of your home while enjoying the warmth and character of this thoughtfully updated retreat. Inside, you'll find a brand-new kitchen and updated bathroom, stone wood burning fireplace, gleaming hardwood

Robin Apps Four Seasons Sotheby's Int'l Realty

3 Strattonwald Rd, Winhall, VT 05340
/29
$455,000 Sold Mar 28, 2025

2 Byington Ln Unit 5, Winhall, VT 05340
- 3 Beds
- 2 Baths
- 1,570 Sq Ft
- Built 1977
Last Sold Summary
- 7% Below List Price
- $290/SF
- 53 Days On Market
Last Listing Agent Robin Apps Four Seasons Sotheby's Int'l Realty

2 Byington Ln Unit 5, Winhall, VT 05340

/40
Est $533,224 Not Listed For Sale

381 Winhall Hollow Rd, Bondville, VT 05340
- 5 Beds
- 4 Baths
- 3,024 Sq Ft
- Built 1970
381 Winhall Hollow Rd, Bondville, VT 05340

Last Sold Summary
- 34% Above List Price
- $132/SF
- 10 Days On Market
Last Sold Price $399,000

Last Listing Agent Carrie Mathews Winhall Real Estate

/35
$695,000 Under Contract
- 4 Beds
- 2 Baths
- 2,715 Sq Ft
9 Old Route 30, Winhall, VT 05340

Classic Vermont farmhouse set on over 18 private acres with Bromley Mountain views, offering timeless character, privacy, and mountain views. This four-bedroom, two-bath home features a striking stone fireplace anchoring the main living space, along with a dedicated library and office—ideal for reading, work, or creative pursuits. Outdoor living shines with a spacious patio and stone firepit,

Carrie Mathews Winhall Real Estate

9 Old Route 30, 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 $439,270

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

163 Vt Route 30, Winhall, VT 05340

/36
Not Listed For Sale

43 Middle Ridge Rd Unit 416, Winhall, VT 05155
- 4 Beds
- 4 Baths
- 2,271 Sq Ft
- Built 2003
43 Middle Ridge Rd Unit 416, Winhall, VT 05155

Last Sold Summary
- $760/SF
- 80 Days On Market
Last Sold Price $1,725,000

Last Listing Agent Timothy Mich Doddridge Stratton Real Estate

/4
$400,000
- Land
- 8.01 Acres
- $49,938 per Acre
248 French Hollow Rd, Winhall, VT 05340

Legacy family property, held until now for its premier location and extraordinary views of Stratton Mountain. Acreage offers a building site that is privately situated off the road with a 4 bedroom state septic permit and ready for the mountain home you have been hoping to create! A beautiful parcel with level plateau for building and a moderate slope down to its lower boundary. Surrounded by a

Kim Morgan-Wohler Wohler Realty Group

248 French Hollow Rd, Winhall, VT 05340
/25
$825,000 Sold Mar 14, 2025

0 Cobble Ridge Rd Unit D2, Winhall, VT 05340
- 4 Beds
- 3 Baths
- 2,317 Sq Ft
- Built 1988
Last Sold Summary
- 8% Below List Price
- $356/SF
- 135 Days On Market
Last Listing Agent Jamie Wylie Stratton Real Estate

0 Cobble Ridge Rd Unit D2, Winhall, VT 05340

/39
Est $765,867 Not Listed For Sale

28 W Branch Rd, Winhall, VT 05340
- 4 Beds
- 3.5 Baths
- 2,300 Sq Ft
- Built 1989
28 W Branch Rd, Winhall, VT 05340

Last Sold Summary
- 51% Below List Price
- $678/SF
- 8 Days On Market
Last Sold Price $1,560,000

Last Listing Agent Jessica Marullo TPW Real Estate

/8
$65,000 Under Contract
- Land
- 1.02 Acres
- $63,725 per Acre
0 Stratton View Rd Unit 26, Winhall, VT 05340

Stratton View Rd Lot # 59 , 1.02 +- acres wooded parcel. 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. Addition lot MLS #5036988 available. Own your piece of Vermont.

Mike England Michael England Real Estate

0 Stratton View Rd Unit 26, Winhall, VT 05340

Showing Results 41 - 80, Page 2 of 18

Vermont Bennington County Winhall

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

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.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage