53 PLEASANT ST
Valuation
Tax & Assessment
Climate Risk
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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
53 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 74% of homes in Windsor County
- Costs more per square foot than 65% of homes in Windsor County
- Bigger than 70% of homes in Windsor County
- Has a smaller lot than 82% of homes in Woodstock 05091
- Older than 93% 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 47% 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 47% of homes nearby
Pricier than 48% of homes nearby
Bigger than 52% of homes nearby
Bigger than 18% of homes nearby
Newer than 15% of homes nearby
| Measure | This home | Woodstock 05091 | Windsor County |
|---|---|---|---|
| Estimated valuepricier than | $591,470 | 47% of homes | 74% of homes |
| Price per ft²pricier than | $301 | 48% of homes | 65% of homes |
| Living areabigger than | 1,964 ft² | 52% of homes | 70% of homes |
| Lot sizebigger than | 0.51 ac | 18% of homes | 22% of homes |
| Year builtnewer than | 1850 | 15% of homes | 7% of homes |
About 53 Pleasant St
How much is 53 Pleasant St, Woodstock, VT worth?
The TopHap Estimate for 53 Pleasant St, Woodstock, VT is $591,470 as of Jul 14, 2026. The likely range is $519,043 to $663,897. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 53 Pleasant St, Woodstock, VT last sell?
53 Pleasant St, Woodstock, VT last sold on Nov 1, 2021 for $339,000, according to the county's recorded deed.
How big is 53 Pleasant St, Woodstock, VT?
53 Pleasant St, Woodstock, VT has 2.5 bathrooms, 1,964 square feet of living space and a 0.51-acre lot.
When was 53 Pleasant St, Woodstock, VT built?
53 Pleasant St, Woodstock, VT was built in 1850, making it 176 years old. It is a colonial home.
What schools serve 53 Pleasant St, Woodstock, VT?
53 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 53 Pleasant St, Woodstock, VT compare to other homes in Woodstock 05091?
Among the 1,848 homes in Woodstock 05091, it is worth more than 47% of them ($591,470 against a typical $610,282), its price per square foot is higher than 48% of them ($301 against a typical $307), it is bigger than 52% of them (1,964 ft² against a typical 1,920 ft²), its lot is bigger than 18% of them (0.51 ac against a typical 3.22 ac) and it is newer than 15% of them (1850 against a typical 1969). Measured against all of Windsor County, it is worth more than 74% 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 53 Pleasant St, Woodstock, VT?
The 2025 property tax bill for 53 Pleasant St, Woodstock, VT was $15,696. The county assessed it at $723,500.
More homes on Pleasant St
- 47 Pleasant St # B677 ft² · Sold $159K · Apr 2026
- 75 Pleasant St$546K3 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$977K3 bd · 3.5 ba · 3,190 ft² · Sold $1.4M · Jul 2022
- 72 Pleasant St$338K2 bd · 1 ba · 964 ft² · Sold $353K · Mar 2022
- 21 Pleasant St$1.2M10 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$201K2 bd · 1 ba · 1,140 ft² · Sold $185K · May 2020
- 43 Pleasant St9 bd · 8.5 ba · 4,146 ft² · Sold $455K · Mar 2020
- 52 Pleasant St4 bd · 2 ba · 1,890 ft² · Sold $560K · Jan 2020
Closest homes
- 51 Pleasant St94 ft · 0.33 ac · Sold $199K · Mar 2014
- 47 Pleasant St172 ft · 677 ft² · Sold $159K · Apr 2026
- 47 Pleasant St$227K172 ft · 1.5 ba · 1,406 ft² · Sold $90K · Oct 2016
- 47 Pleasant St172 ft · 1 bd · 2,148 ft² · Sold $199K · Jul 2020
- 59 Pleasant St$515K177 ft · 4 bd · 3.5 ba · 1,960 ft² · Sold $319K · Aug 2015
- 4 Stanton St$686K254 ft · 4 bd · 2.5 ba · 1,859 ft² · Sold $655K · Dec 2025
- 52 Pleasant St281 ft · 4 bd · 2 ba · 1,890 ft² · Sold $560K · Jan 2020
- 54 Pleasant St$246K337 ft · 1 bd · 1 ba · 980 ft² · Sold Jan 1900
More homes in Woodstock 05091
- 2605 Cox District Rd$785K6 bd · 3.5 ba · 3,284 ft² · Sold $738K · Aug 2026
- 2358 Long Hill Rd$3.1M5 bd · 3.5 ba · 4,165 ft² · Sold $6.1M · Aug 2026
- 145 Riverbend Way3 bd · 2 ba · 1,064 ft² · Sold Aug 2026
- 1244 W Woodstock Rd$298K2 bd · 1 ba · 1,059 ft² · Sold $360K · Aug 2026
- 85 Townhouse Way$510K2 bd · 3 ba · 1,515 ft² · Sold $485K · Aug 2026
- 2 High St$1.2M4 bd · 1.5 ba · 1,590 ft² · Sold $1.1M · Jul 2026
- 2762 Vt Route 12$654K3 bd · 2.5 ba · 1,787 ft² · Sold $750K · Jul 2026
- 37 Maxham Rd352.61 ac · Sold Jul 2026
- 2748 E Woodstock Rd$115K1 bd · 1 ba · 691 ft² · Sold $200K · Jul 2026
- 5525 N Bridgewater Rd$893K2 bd · 2.5 ba · 2,732 ft² · Sold $1.5M · Jul 2026
- 616 Rose Hill Rd$817K3 bd · 2 ba · 1,440 ft² · Sold $775K · Jul 2026
- 29 Slayton Ter$498K4 bd · 1.5 ba · 1,708 ft² · Sold $304K · Jul 2026
Assigned schools
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