Listed by Dana Waters • Dark Horse Realty. Bought with BHG Masiello Brattleboro.
Off Market Dec 2025 for $525K
$642,148
Est. refi paymentEst. refi$3,337/mo
4
bd
•
2 ba
•
2,380
sq ft
77 Winding Rd, Brownsville, VT 05037
About this home
Light and thoughtful architect designed home on a lovely 12 acre hilltop. Set in a magical landscape of exposed ledge, old stone walls & established perennial gardens. Stunning views of both Mt Ascutney and Little Ascutney. Spacious and airy, large windows and south-facing skylights provide passive solar warmth throughout the 4 bedroom home. Open layout is clean and efficient with cathedral ceilings & custom touches. Drilled well. The kitchen has smart, functional design. Dining/Family room and sunken living room. Large primary bedroom with ensuite bath, laundry, and deck. A perfect spot for anyone who enjoys the outdoors. Direct access to recreational trails. Close to Ascutney Outdoors, WW Town Forest & the Brownsville Butcher & Pantry. A peaceful homestead in a truly special corner of Vermont. Listing price adjusted to reflect older roof, decks & skylights. All still serviceable.
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Earn from this home
Refinance
$0
Est. cash available
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Rent
$2,292/mo
Redfin rental estimate
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Market trends in 05037, VT
Last updated August 2026
Buyer's Market
Seller's Market
Buyer's market
Sale-to-List Price
94.1%
2.7% MoM
Median sale price
$315K
$22K MoM
Avg. days on market
69d
9 days MoM
Recently sold homes
6
0 MoM
Provided by Redfin
Sale history for 77 Winding Rd
Date
Event
Price
PrimeMLS #5064038
Dec 15, 2025
Sold
$525,000
$221/sq ft
Oct 26, 2025
Contingent
—
Oct 2, 2025
Listed
$520,000
$218/sq ft
PrimeMLS #4466187
Nov 28, 2016
Sold
$280,000
$118/sq ft
Oct 2, 2016
Contingent
—
May 9, 2016
Price Changed
$299,000
$126/sq ft
Apr 11, 2016
Price Changed
$325,000
$137/sq ft
Jan 11, 2016
Listed
$345,000
$145/sq ft
+31
MUST SEE! Exceptional value. Fine 4BR 2 Bath Custom home privately sited with great views of Mt. Ascutney. Builder is known for energy efficient quality construction. Cathedral ceiling with skylights allow for passive solar heating as well as great sunlight all day long, woodstove in LR. Multi level living offers space for everyone. UPDATED KITCHEN! Decks overlook lawn with fruit trees & blueberry bushes. Xfinity (Comcast) high speed Internet. Active solar hot water system. Connect to recreational trails directly from house.
PrimeMLS #1
Jul 10, 2015
Price Changed
$355,000
$149/sq ft
Jun 19, 2015
Price Changed
$379,000
$159/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$5,954 (+3.5%)
$180,500 + $341,500
$522,000
2024
$5,751 (−2.6%)
$180,500 + $341,500
$522,000
2023
$5,902 (−14.3%)
$149,300 + $204,500
$353,800
2022
$6,884 (−8.7%)
$149,300 + $204,500
$353,800
2021
$7,538 (+4.3%)
$149,300 + $204,500
$353,800
2020
$7,226 (−5.4%)
$149,300 + $204,500
$353,800
2019
$7,638 (−7.0%)
$149,300 + $204,500
$353,800
2018
$8,213 (+21.8%)
$149,300 + $204,500
$353,800
2016
$6,745 (−7.4%)
$149,300 + $204,500
$353,800
2015
$7,284 (−2.2%)
$149,300 + $204,500
$353,800
2014
$7,445
$149,300 + $204,500
$353,800
2013
$149,300 + $204,500
$353,800
Tax history for 77 Winding Rd
Year
Property tax
Land + Additions
Assessment*
2025
$5,954 (+3.5%)
$180,500 + $341,500
$522,000
2024
$5,751 (−2.6%)
$180,500 + $341,500
$522,000
2023
$5,902 (−14.3%)
$149,300 + $204,500
$353,800
2022
$6,884 (−8.7%)
$149,300 + $204,500
$353,800
2021
$7,538 (+4.3%)
$149,300 + $204,500
$353,800
2020
$7,226 (−5.4%)
$149,300 + $204,500
$353,800
2019
$7,638 (−7.0%)
$149,300 + $204,500
$353,800
2018
$8,213 (+21.8%)
$149,300 + $204,500
$353,800
2016
$6,745 (−7.4%)
$149,300 + $204,500
$353,800
2015
$7,284 (−2.2%)
$149,300 + $204,500
$353,800
2014
$7,445
$149,300 + $204,500
$353,800
2013
$149,300 + $204,500
$353,800
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Directions: Route 44 to Westgate Road, immediate left onto Winding Road, at fork bear left on to driveway follow past shed on left, up hill to the house (you can't see it from road.)
Public facts
Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 12.2 acres
Style: Other
Year Built: —
Year Renovated: —
County: Windsor County
APN: 73823510591
Home facts updated by county records on Sep 2, 2026