50 CHESTNUT ST
Valuation
Tax & Assessment
Climate Risk
Scores 0–100; higher = greater projected risk.
Property Facts
Transaction History(6)
Sales and refinances filed with the county for this home. Not every transfer is a normal sale, so check the type before comparing prices.Neighborhood · ZIP 05301These are comparison scores, not percentages. 100 equals the national average, so 150 means about 50% above average.
Index scale: 100 = US average (tick). Lower is better.
Owner Tools
Data by ATTOM. Valuations are automated estimates, not appraisals. Photos from Google Street View and may not depict the current property state.
How this home compares
50 Chestnut St measured against every home in its neighborhood, its ZIP code and its county, using county assessor records refreshed nightly. A home can stand out in one of those areas and look ordinary in another, because each one holds a different mix of homes.
- Costs less per square foot than 75% of homes in Windham County
- Has a smaller lot than 86% of homes in Windham County
- Older than 72% of homes in Windham County
What homes are worth in Brattleboro 05301
Each bar is how many homes fall in that price range. The marker is this home.
This home is worth more than 56% of homes in Brattleboro 05301.
How it measures up in Brattleboro 05301
The dot is this home. The mark in the middle is the typical home in Brattleboro 05301.
Pricier than 56% of homes nearby
Pricier than 36% of homes nearby
Bigger than 59% of homes nearby
Bigger than 21% of homes nearby
Newer than 32% of homes nearby
| Measure | This home | Brattleboro 05301 | Windham County |
|---|---|---|---|
| Estimated valuepricier than | $342,436 | 56% of homes | 44% of homes |
| Price per ft²pricier than | $201 | 36% of homes | 25% of homes |
| Living areabigger than | 1,704 ft² | 59% of homes | 58% of homes |
| Lot sizebigger than | 0.25 ac | 21% of homes | 14% of homes |
| Year builtnewer than | 1933 | 32% of homes | 28% of homes |
About 50 Chestnut St
How much is 50 Chestnut St, Brattleboro, VT worth?
The TopHap Estimate for 50 Chestnut St, Brattleboro, VT is $342,436 as of Aug 30, 2026. The likely range is $316,645 to $368,227. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 50 Chestnut St, Brattleboro, VT last sell?
50 Chestnut St, Brattleboro, VT last sold on Nov 7, 2019 for $209,000, according to the county's recorded deed. TopHap holds 5 recorded sales for this parcel.
How big is 50 Chestnut St, Brattleboro, VT?
50 Chestnut St, Brattleboro, VT has 3 bedrooms, 1 bathrooms, 1,704 square feet of living space and a 0.25-acre lot.
When was 50 Chestnut St, Brattleboro, VT built?
50 Chestnut St, Brattleboro, VT was built in 1933, making it 93 years old. It is a colonial home. The building has 2 stories.
How does 50 Chestnut St, Brattleboro, VT compare to other homes in Brattleboro 05301?
Among the 5,717 homes in Brattleboro 05301, it is worth more than 56% of them ($342,436 against a typical $323,948), its price per square foot is higher than 36% of them ($201 against a typical $219), it is bigger than 59% of them (1,704 ft² against a typical 1,522 ft²), its lot is bigger than 21% of them (0.25 ac against a typical 1.2 ac) and it is newer than 32% of them (1933 against a typical 1966). Measured against all of Windham County, it is worth more than 44% of homes there. These shares are recounted nightly from the full county assessor record for each area, not from active listings.
What are the property taxes on 50 Chestnut St, Brattleboro, VT?
The 2025 property tax bill for 50 Chestnut St, Brattleboro, VT was $3,129. The county assessed it at $178,380.
More homes on Chestnut St
- 164 Chestnut St3 bd · 1 ba · 882 ft² · Sold $265K · Aug 2026
- 105 Chestnut St4 bd · 2 ba · 2,715 ft² · Sold $395K · Nov 2025
- 108 Chestnut St$338K4 bd · 1.5 ba · 1,544 ft² · Sold $322K · Jul 2025
- 22 Chestnut St # 5$202KCondominium · Sold $193K · Jan 2025
- 44 Chestnut St4 bd · 2 ba · 2,497 ft² · Sold $350K · May 2024
- 36 Chestnut St$353K3 bd · 2 ba · 1,614 ft² · Sold $330K · Nov 2022
- 176 Chestnut St$314K2 bd · 1 ba · 1,728 ft² · Sold $240K · Mar 2021
- 106 Chestnut St2 bd · 1 ba · 1,056 ft² · Sold $140K · Jul 2020
- 155 Chestnut St$254K3 bd · 1.5 ba · 1,594 ft² · Sold $172K · Dec 2019
- 104 Chestnut St$293K3 bd · 1.5 ba · 1,688 ft² · Sold $175K · Aug 2019
- 185 Chestnut St$367K4 bd · 2 ba · 1,512 ft² · Sold Nov 2018
- 62 Chestnut St4 bd · 3 ba · 2,856 ft² · Sold Oct 2018
Closest homes
- 58 Chestnut St$228K66 ft · 3 bd · 1.5 ba · 1,952 ft² · Sold $110K · Mar 2016
- 44 Chestnut St66 ft · 4 bd · 2 ba · 2,497 ft² · Sold $350K · May 2024
- 49 Vine St163 ft · 2,079 ft² · Sold $300K · Nov 2020
- 62 Chestnut St134 ft · 4 bd · 3 ba · 2,856 ft² · Sold Oct 2018
- 36 Chestnut St$353K136 ft · 3 bd · 2 ba · 1,614 ft² · Sold $330K · Nov 2022
- 55 Vine St$231K196 ft · 3 bd · 1 ba · 960 ft² · Sold $141K · May 2021
- 35 Vine St193 ft · 7 bd · 3 ba · 1,806 ft² · Sold Jan 1900
- 51 Chestnut St217 ft · 4 bd · 4 ba · 2,172 ft² · Sold $172K · Jun 2005
More homes in Brattleboro 05301
- 2336 Sweet Pond Rd$246K2 bd · 2 ba · 1,248 ft² · Sold $340K · Sep 2026
- 120 Carriage Hill Rd$369K3 bd · 1.5 ba · 1,440 ft² · Sold $369K · Sep 2026
- 36 Pauls Rd3.46 ac · Sold $325K · Sep 2026
- 50 Spring Hill Rd$179K2 bd · 2 ba · 864 ft² · Sold $195K · Sep 2026
- 1288 Green River Rd$228K2 bd · 2 ba · 942 ft² · Sold $38K · Sep 2026
- 135 S Main St5 bd · 3 ba · 2,682 ft² · Sold $94K · Sep 2026
- 136 Oak Grove Ave$295K3 bd · 1 ba · 1,350 ft² · Sold $275K · Sep 2026
- 671 Kelly Rd1 bd · 1 ba · 600 ft² · Sold $59K · Sep 2026
- 20 Homestead Pl4 bd · 2 ba · 2,430 ft² · Sold $111K · Sep 2026
- 87 Orchard St$359K4 bd · 3.5 ba · 2,794 ft² · Sold $359K · Sep 2026
- 211 Pleasant Valley Rd2 bd · 1 ba · 1,104 ft² · Sold $525K · Sep 2026
- 390 Pleasant Valley Rd$1.2M4 bd · 3.5 ba · 4,866 ft² · Sold $1.2M · Sep 2026
Explore the area
See this home in context
Open 50 Chestnut St on TopHap’s interactive map to compare it against every sale nearby, overlay school zones and flood risk, and run a CMA.
Open in map