Find Your VT Dream Home
Address Search
Winhall VT Real Estate: Homes for Sale Near Stratton and Bromley
Updated September 27, 2026 by Tony Walton, Principal Broker, New England Landmark Realty
Quick Answer
Winhall is a Bennington County town that includes the village of Bondville and the Stratton Mountain Access Road, putting many of its homes minutes from Stratton Mountain Resort, with Bromley and Manchester close by. In 2026 through September 27, 46 single-family homes sold in Winhall at a median of $834,500, from $340,000 to $3,025,000. The median home sold in 22 days, at 97.3% of its original list price.
Key Takeaways
Two-Sentence Summary
Winhall is southern Vermont's busiest ski-country market among the towns we cover, with 46 single-family sales in 2026 and 17 of them at $1 million or more. Unlike slower nearby markets, most Winhall homes sold within a month and close to asking.
If You Only Remember 3 Things
- The 2026 Winhall median was $834,500 across 46 single-family sales.
- Well-priced homes move: 30 of 46 sold within 30 days, at a median of 100% of list price.
- There's a wide range: 8 homes sold under $500,000, and 5 sold for $2 million or more.
Quick Facts
- Single-family sales, Jan 1 to Sept 27, 2026: 46, median $834,500, range $340,000 to $3,025,000
- By price: 8 under $500,000; 12 from $500,000 to $749,999; 9 from $750,000 to $999,999; 8 from $1 million to $1.49 million; 4 from $1.5 million to $1.99 million; 5 at $2 million or more
- Median days on market: 22
- Typical home (medians): 4 bedrooms, about 2,730 square feet, built around 1980, on about 1.4 acres
- ZIP code: 05340 (Bondville)
The Winhall Market Right Now
Winhall's 2026 single-family market was active. The median home sold in 22 days, 11 of 46 sold within a week, and 17 sold at or above their original list price. The 30 homes that sold within 30 days closed at a median of 100% of list price, while the 10 that took 100 days or more closed at a median of 91.6%.
Check live numbers in our Winhall market report, and see The Art of Pricing Your Vermont Home.
What Winhall Homes Sell For
- 1960s and 1970s ski-era homes: 19 sales at a median of $670,500. They account for 8 of the 11 sales under $600,000.
- 1980s and 1990s homes: 18 sales, including four on High Meadow Road from $941,000 to $3,025,000.
- Homes built since 2000: 7 sales, from $945,000 to $2,850,000.
- Land: 9 sales had 5 acres or more, and 7 had 10 acres or more.
Why Buyers Choose Winhall
- Skiing: the Stratton Mountain Access Road starts in Bondville, and Bromley is a short drive away.
- Four seasons: hiking and mountain biking in the Green Mountains, plus summer activities at the ski areas.
- Manchester nearby: shopping, dining, and services in Manchester, plus Burr and Burton Academy.
Nearby markets: see our Manchester and Dorset pages.
Schools
Winhall does not operate its own public school. The town has historically paid tuition for students to attend approved schools, including Burr and Burton Academy in Manchester for high school. Vermont's education rules are changing, so confirm current options with the Winhall School District through the Bennington-Rutland Supervisory Union.
Costs to Plan For
Vermont's property transfer tax on a primary residence is 0.5% on the first $200,000 and 1.47% above that, about $10,300 at the $834,500 Winhall median. A second home pays 3.62%, about $30,200. A VHFA-financed primary residence is exempt on the first $250,000. If the home won't be your primary residence, budget for the second-home rate, and check your town's short-term rental rules if you plan to rent it. See our Vermont closing costs guide.
Frequently Asked Questions
What is the median home price in Winhall, VT?
Single-family homes in Winhall sold at a median of $834,500 across 46 sales from January 1 to September 27, 2026.
How fast do homes sell in Winhall?
The median Winhall home sold in 22 days in 2026. 30 of 46 sold within 30 days at a median of 100% of list price.
Is Winhall the same as Stratton?
No. Winhall and Stratton are separate towns. Stratton Mountain Resort sits mostly in Stratton, while Winhall includes Bondville and the Stratton Mountain Access Road, so many Winhall homes are close to the resort.
Can I find a home under $500,000 in Winhall?
Sometimes. 8 of Winhall's 46 single-family sales in 2026 were under $500,000.
Where do Winhall students go to school?
Winhall does not run its own school and has historically paid tuition for students to attend approved schools, including Burr and Burton Academy for high school. Check current options with the Bennington-Rutland Supervisory Union.
How much is the transfer tax on a Winhall home?
At the $834,500 median, about $10,300 for a primary residence and about $30,200 for a second home.
What to Do Next
Call our office at 802-253-4711, reach Tony Walton directly at 802-233-4107, or contact us.
Want Vermont market updates and homeowner tips in your inbox? Sign up for Tony's newsletter. You can unsubscribe at any time.
Sources
- Winhall single-family sales: MLS search of single-family homes sold January 1 to September 27, 2026. Medians and ratios calculated by New England Landmark Realty from the individual sales.
- Bennington Banner, "Winhall will pay lower tuition to BBA, examine non-choice options"
- Bennington-Rutland Supervisory Union, Winhall School District
- Vermont Department of Taxes, Property Transfer Tax
Winhall Homes For Sale
Build your Stratton estate on the golf course. Two adjoining High Meadow building lots (E-13R and E-14R, 2.48± surveyed acres) that abut the Stratton golf course, with St...
- 5111789 MLS
- 2.48 Acres
Hilltop Hideaway: a bright saltbox retreat in Forest Farms, 5-10 minutes to Stratton. Cathedral glass-gable loft with brick fireplace, two more wood-burning fireplaces in...
- 3 Beds
- 4 Baths
- 5111784 MLS
- 1.52 Acres
Shred Shack: the portfolio's workhorse. A post-and-beam Stratton ski house with mountain views on 2.2 private acres, about 6 minutes to the base. Soaring timber great roo...
- 4 Beds
- 3 Baths
- 5111782 MLS
- 2.2 Acres
Wandering Moose: a rare heated-pool ski house on High Meadow, on the Stratton winter shuttle route. Rebuilt top to bottom in 2024 with a designer interior, then finished ...
- 4 Beds
- 5 Baths
- 5111781 MLS
- 1.08 Acres
First Chair Lair: a proven, turnkey Stratton rental on High Meadow, on the complimentary winter-weekend Stratton shuttle route and about 5 minutes to the base. Two-story ...
- 5 Beds
- 4 Baths
- 5111779 MLS
- 1 Acres
This picture perfect energy conscience geo-thermal (saves big on heating or AC) and electric vehicle friendly, well maintained log home is offered fully furnished! The ...
- 3 Beds
- 2 Baths
- 5110111 MLS
- 0.41000000000000003 Acres
Perched high on Pearl Buck Drive, this distinctive Vermont home is all about location—and the scenery is truly exceptional. Sweeping mountain vistas capture both Stratton...
- 3 Beds
- 2 Baths
- 5108777 MLS
- 3.5 Acres
Discover this truly exceptional Vermont Mountain Retreat just seven miles from Stratton Mountain, perfectly located for four-season living! Boasting an inviting open layo...
- 4 Beds
- 6 Baths
- 5108444 MLS
- 2.1 Acres
This 3-bedroom,3-bathroom, Tri-level Piper Ridge "Tunbridge" Townhome/Condo has a full facing view of the face of Stratton Mountain. It is basically in original condition...
- 3 Beds
- 3 Baths
- 5108248 MLS
***Open House Sunday 9/6/26 11:00-1:00*** Charming, comfortable, and ideally situated, this expanded 3-bedroom, 2-bath A-frame captures the essence of a Vermont retreat. ...
- 3 Beds
- 2 Baths
- 5108069 MLS
- 0.32 Acres
Escape to the mountains and enjoy everything Stratton, Vermont has to offer in this fabulous 4 bedroom, 4 bath contemporary home, ideally located on a private cul-de-sac ...
- 4 Beds
- 4 Baths
- 5107687 MLS
- 1.37 Acres
A rare Stratton ownership opportunity with exceptional amenities and possibilities. The purchase presents an opportunity for the buyer to bypass the Stratton Mountain Clu...
- 3 Beds
- 2 Baths
- 5107482 MLS
- 10.76 Acres
11 Round Tree Road, Winhall, VT 05340 A landmark on Round Tree Road, this house has inviting curb appeal with its stone façade and archway. With 1.83 acres the house has...
- 4 Beds
- 4 Baths
- 5107395 MLS
- 1.83 Acres
This exceptional 3.8-acre, partially-cleared Winhall lot offers potentially unobstructed views of Stratton mountain, and is permitted for a 4BR home perched at the top of...
- 5107343 MLS
- 3.8 Acres
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 bas...
- 3 Beds
- 2 Baths
- 5107205 MLS
- 1.03 Acres
This expansive building lot, situated just off the Stratton Access Road, offers breathtaking views of Bromley Mountain, presenting an ideal opportunity to construct your ...
- 5107127 MLS
- 10.06 Acres
Experience four season Vermont living at 33 Burnt Hill Road in Strattonwald, a recreational community in Winhall just minutes from Stratton Mountain. Set on 1.09 wooded a...
- 3 Beds
- 2 Baths
- 5106334 MLS
- 1.09 Acres
Discover the opportunity to create your own Vermont getaway on this beautiful 1-acre parcel on Sylvan Ridge Road in Winhall. Ideally situated between Stratton Mountain an...
- 5106244 MLS
- 1 Acres
Tucked at the end of a quiet back road less than one mile from the Stratton Access Road, The Winhall Condos offer a peaceful mountain retreat with convenient access to bo...
- 2 Beds
- 2 Baths
- 5106209 MLS
Set among sun-dappled woodlands along a peaceful country road, this distinctive post-and-beam home captures the charm of a Vermont sugar shack with the warmth of a classi...
- 3 Beds
- 2 Baths
- 5105544 MLS
- 1.78 Acres
TURN-KEY VERMONT MOUNTAIN RETREAT JUST MINUTES FROM BROMLEY & STRATTON! Beautifully renovated in 2021, this fully furnished 3-bedroom, 2-bath condominium offers the perfe...
- 3 Beds
- 2 Baths
- 5105387 MLS
- 3.2 Acres
Set among the trees just minutes from Stratton Resort, this spacious 3-bedroom, 3-bath mountain home combines beautiful views, flexible living spaces and plenty of room f...
- 3 Beds
- 3 Baths
- 5105009 MLS
- 1 Acres
Privately situated in a most beautiful setting, this grand Vermont estate commands a remarkable landscape, with Stratton Mountain rising majestically beyond the tree line...
- 7 Beds
- 10 Baths
- 5104104 MLS
- 42.93 Acres
Your Vermont adventure starts here. This 0.90 - acre parcel offers a fantastic location between Stratton, Bromley, and Magic Mountains, with easy access to the year round...
- 5104082 MLS
- 1 Acres
Selling very close to the assessed value of $1,126,100!!! This 2026 town assessment just made this property a REAL DEAL because the Owner wants 1,200,000. This property c...
- 6 Beds
- 4 Baths
- 5103259 MLS
- 0.77 Acres
Embrace Vermont living with this fully furnished, 4-bedroom, 3.5-bath contemporary home located just minutes from Stratton Mountain Resort. Situated on a serene 1-acre lo...
- 4 Beds
- 4 Baths
- 5102830 MLS
- 1 Acres
Set within the exclusive High Meadow community, one of Stratton's most prestigious mountain enclaves, 6 Sunset Ridge is an extraordinary resort residence of post and bea...
- 5 Beds
- 4 Baths
- 5101868 MLS
- 1.12 Acres
The 3.3-acre parcel of land located on Mt Haunts Road in Winhall has received approval for the construction of a four-bedroom residence, presenting an outstanding opportu...
- 5099438 MLS
- 3.3 Acres
Wooded one acre parcel off Rt 30 in Winhall, just past the west entrance to French Hollow Rd. and by Green Mountain National Forest and VTRT 30. This is a sloping /wooded...
- 5099207 MLS
- 0.99 Acres
Expansive Stratton Mountain Resort Residence with exceptional floor plan and renovation! Featuring an upscale redesign of two top floor primary suite bathrooms, updated ...
- 6 Beds
- 6 Baths
- 5098800 MLS
- 1 Acres
Where Mountains Meet Modern Living: Perched just moments from the energy of Stratton Mountain Resort, this contemporary mountain home reimagines what a Vermont getaway fe...
- 4 Beds
- 4 Baths
- 5098019 MLS
- 1 Acres
Your Ultimate Vermont Mountain Retreat Awaits! Luxury log home plus a 2,250 sqft guest house! Just 4 miles from Stratton & minutes to Bromley, this inviting log home is ...
- 3 Beds
- 4 Baths
- 5097749 MLS
- 1 Acres
First time on the market, this spacious mountain home has been lovingly maintained by one family since it was built in 1980. Tucked away on a generous double lot at the d...
- 4 Beds
- 4 Baths
- 5097091 MLS
- 2.39 Acres
Experience four-season Vermont living in this beautifully appointed end-unit townhome in the highly sought-after Highgate neighborhood at Piper Ridge, one of Stratton Mou...
- 3 Beds
- 3 Baths
- 5094616 MLS
Ideally located between Manchester and the mountains, this home offers the perfect blend of convenience, comfort, and Vermont charm. Just 10 minutes to Stratton, 5 minute...
- 3 Beds
- 2 Baths
- 5094344 MLS
- 1.05 Acres
Offered as a set, this property presents a rare opportunity to own two separately deeded parcels in a location that is only minutes from Stratton Mountain yet worlds away...
- 5093473 MLS
- 2.31 Acres
Direct views of Stratton Mountain set the stage for this exceptional post-and-beam residence, offering a rare combination of luxury living, entertaining space, and rental...
- 6 Beds
- 7 Baths
- 5092802 MLS
- 1.49 Acres
Tucked into Stratton Mountain Resort’s sought after High Meadow neighborhood, 6 Old Ridge Road offers the rare combination of substantial square footage, significant rece...
- 5 Beds
- 5 Baths
- 5090234 MLS
- 1 Acres
Exceptional Offering and Value Located in Stratton Resort’s sought-after High Meadow community, this beautifully maintained and turnkey home offers the perfect blend of c...
- 4 Beds
- 3 Baths
- 5090036 MLS
- 1.2 Acres
LABOR DAY WEEKEND BEGINS WITH A HUGE PRICE CHANGE! - Move into this brand new stunning custom contemporary set on over 3 acres in coveted Stratton ski country. This ...
- 4 Beds
- 5 Baths
- 5085635 MLS
- 3.43 Acres
Beautiful parcel located in a highly desirable Winhall neighborhood, just minutes to Bromley and Stratton Mountains, and a short drive to Manchester’s shops and dining. T...
- 5083719 MLS
- 1.2 Acres
Experience the pinnacle of Green Mountain living on this extraordinary 23.5-acre property. Perfectly positioned to capture a stunning, direct-line-of-sight view of Stratt...
- 1 Baths
- 5081867 MLS
- 23.5 Acres
Set in a prime location along Stratton Access Road, this Intervale townhouse offers an easygoing mountain lifestyle with everything you need close at hand—including weeke...
- 3 Beds
- 3 Baths
- 5080673 MLS
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 opportuni...
- 5079556 MLS
- 77.6 Acres
Experience Premiere Luxury living in this newly built mountain residence with extraordinary panoramic views . Just minutes to Stratton Mountain'sTrails and move in ready,...
- 4 Beds
- 4 Baths
- 5076149 MLS
- 2.5 Acres
Set along Lower Taylor Hill Road in Winhall, this 21.2 +/- acre offering captures the privacy, natural beauty, and four-season lifestyle that define Southern Vermont livi...
- 5074721 MLS
- 21.2 Acres
Exceptional offering. This premier parcel defines phase II of Ravenwood, an enclave of distinctive and premier mountain residences. This notable site offers extraordinar...
- 5073717 MLS
- 1.23 Acres
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 ...
- 5073637 MLS
- 10.26 Acres
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,...
- 5072896 MLS
- 2.26 Acres
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 soug...
- 4 Beds
- 4 Baths
- 5071605 MLS
- 1.37 Acres
Build your dream home on this ready-to-go 1-acre lot in the Green Mountains. Located on a private gravel road in Winhall, this mostly cleared parcel offers a gentle slope...
- 5070793 MLS
- 1 Acres
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 of...
- 5068233 MLS
- 8.01 Acres
Spectacular West and Southerly Views over Manchester Valley and boasts a bird's eye view across to the Equinox Mountain! Located on the Manchester side of Winhall, this p...
- 4963233 MLS
- 2.9 Acres
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, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .
Address Search
Search Popular Areas
What Are You?
What Are Homes Selling For in Your Town?
Build a free Vermont market report: recent sales, prices, and days on market for any town and price range.
Get My Free Market Report Estimate your payment and closing costs Or get Vermont market updates by email