20 PLEASANT ST
Valuation
Tax & Assessment
Climate Risk
Scores 0–100; higher = greater projected risk.
Property Facts
Transaction History(1)
Sales and refinances filed with the county for this home. Not every transfer is a normal sale, so check the type before comparing prices.Assigned SchoolsThe public schools this address is zoned for. Boundaries change, so confirm with the district before you count on it.
District: Windsor Central Unified Union School District
Neighborhood · ZIP 05091These 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
20 Pleasant 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.
- Worth more than 90% of homes in Windsor County
- Costs more per square foot than 82% of homes in Windsor County
- Bigger than 82% of homes in Windsor County
- Has a smaller lot than 79% of homes in Woodstock 05091
- Older than 95% of homes in Windsor County
What homes are worth in Woodstock 05091
Each bar is how many homes fall in that price range. The marker is this home.
This home is worth more than 72% of homes in Woodstock 05091.
How it measures up in Woodstock 05091
The dot is this home. The mark in the middle is the typical home in Woodstock 05091.
Pricier than 72% of homes nearby
Pricier than 63% of homes nearby
Bigger than 68% of homes nearby
Bigger than 21% of homes nearby
Newer than 11% of homes nearby
| Measure | This home | Woodstock 05091 | Windsor County |
|---|---|---|---|
| Estimated valuepricier than | $943,104 | 72% of homes | 90% of homes |
| Price per ft²pricier than | $388 | 63% of homes | 82% of homes |
| Living areabigger than | 2,428 ft² | 68% of homes | 82% of homes |
| Lot sizebigger than | 0.67 ac | 21% of homes | 26% of homes |
| Year builtnewer than | 1840 | 11% of homes | 5% of homes |
About 20 Pleasant St
How much is 20 Pleasant St, Woodstock, VT worth?
The TopHap Estimate for 20 Pleasant St, Woodstock, VT is $943,104 as of Sep 24, 2026. The likely range is $677,270 to $1,208,938. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 20 Pleasant St, Woodstock, VT last sell?
20 Pleasant St, Woodstock, VT last sold on Dec 16, 2019 for $725,000, according to the county's recorded deed.
How big is 20 Pleasant St, Woodstock, VT?
20 Pleasant St, Woodstock, VT has 3 bedrooms, 2 bathrooms, 2,428 square feet of living space and a 0.67-acre lot.
When was 20 Pleasant St, Woodstock, VT built?
20 Pleasant St, Woodstock, VT was built in 1840, making it 186 years old. The building has 1 story.
What schools serve 20 Pleasant St, Woodstock, VT?
20 Pleasant St, Woodstock, VT is assigned to Woodstock Elementary School (elementary), rated A; Woodstock Union Middle / High School (middle), rated A. All sit in Windsor Central Unified Union School District. Attendance boundaries change — confirm with the district before relying on an assignment.
How does 20 Pleasant St, Woodstock, VT compare to other homes in Woodstock 05091?
Among the 1,848 homes in Woodstock 05091, it is worth more than 72% of them ($943,104 against a typical $676,076), its price per square foot is higher than 63% of them ($388 against a typical $349), it is bigger than 68% of them (2,428 ft² against a typical 1,920 ft²), its lot is bigger than 21% of them (0.67 ac against a typical 3.26 ac) and it is newer than 11% of them (1840 against a typical 1969). Measured against all of Windsor County, it is worth more than 90% 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 20 Pleasant St, Woodstock, VT?
The 2025 property tax bill for 20 Pleasant St, Woodstock, VT was $16,773. The county assessed it at $628,900.
More homes on Pleasant St
- 47 Pleasant St # B677 ft² · Sold $159K · Apr 2026
- 75 Pleasant St$552K3 bd · 1.5 ba · 1,064 ft² · Sold $525K · Jan 2026
- 2 Pleasant St$2.4M4 bd · 3.5 ba · 3,998 ft² · Sold $2.4M · Dec 2025
- 29 Pleasant St0.56 ac · Sold $925K · Oct 2025
- 28 Pleasant St0.61 ac · Sold $1.3M · Jan 2023
- 15 Pleasant St$1.1M3 bd · 3.5 ba · 3,190 ft² · Sold $1.4M · Jul 2022
- 72 Pleasant St$411K2 bd · 1 ba · 964 ft² · Sold $353K · Mar 2022
- 53 Pleasant St$730K2.5 ba · 1,964 ft² · Sold $339K · Nov 2021
- 21 Pleasant St$1.3M10 bd · 10 ba · 5,460 ft² · Sold $950K · Feb 2021
- 47 Pleasant St # C1 bd · 2,148 ft² · Sold $199K · Jul 2020
- 73 Pleasant St$260K2 bd · 1 ba · 1,140 ft² · Sold $185K · May 2020
- 43 Pleasant St9 bd · 8.5 ba · 4,146 ft² · Sold $455K · Mar 2020
Closest homes
- 26 Pleasant St$856K72 ft · 3 bd · 3 ba · 2,616 ft² · Sold $400K · Mar 2013
- 18 Pleasant St$1.1M79 ft · 4 bd · 2.5 ba · 3,294 ft² · Sold $854K · Apr 2019
- 28 Pleasant St143 ft · 0.61 ac · Sold $1.3M · Jan 2023
- 16 Pleasant St$2.3M169 ft · 4 bd · 4 ba · 3,337 ft² · Sold $1.8M · Aug 2014
- Central St268 ft · 0.15 ac · Sold Jan 1900
- 17 Pleasant St$499K316 ft · 1 bd · 1.5 ba · 1,666 ft² · Sold $362K · Oct 2007
- 12 Pleasant St$739K260 ft · 2 bd · 2 ba · 1,813 ft² · Sold $255K · Jan 1990
- 30 Pleasant St$1.2M274 ft · 0.55 ac · Sold Jan 1900
More homes in Woodstock 05091
- 124 Riverbend Way2 bd · 1 ba · 888 ft² · Sold $8K · Oct 2026
- 217 S Perry Rd$840K3 bd · 3 ba · 2,667 ft² · Sold $805K · Oct 2026
- 418 Fletcher Hill Rd3 bd · 2.5 ba · 2,434 ft² · Sold $1.5M · Oct 2026
- 40 Deer Ridge Way$560K4 bd · 2 ba · 2,671 ft² · Sold $400K · Sep 2026
- 648 Church Hill Rd$1.2M3 bd · 3 ba · 2,358 ft² · Sold $1.2M · Sep 2026
- 598 E Woodstock Rd$520K4 bd · 3 ba · 3,190 ft² · Sold $520K · Sep 2026
- 2256 E Woodstock Rd$413K4 bd · 1 ba · 2,160 ft² · Sold $195K · Sep 2026
- 37 South St$680K3 bd · 2 ba · 1,660 ft² · Sold $670K · Sep 2026
- 16 Mountain Ave$1.1M3 bd · 3.5 ba · 2,880 ft² · Sold $10K · Sep 2026
- 88 Happy Valley Rd$515K4 bd · 3 ba · 1,824 ft² · Sold $515K · Sep 2026
- 185 Riverbend Way3 bd · 2 ba · 980 ft² · Sold $45K · Aug 2026
- 2605 Cox District Rd$742K6 bd · 3.5 ba · 3,284 ft² · Sold $738K · Aug 2026
Assigned schools
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