27 CHESTNUT ST
Valuation
Tax & Assessment
Property Facts
Transaction History(4)
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: Weston School District
Neighborhood · ZIP 02493These 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
27 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.
- Among the most valuable homes in Middlesex County
- Costs more per square foot than 85% of homes in Middlesex County
- Among the largest homes in Middlesex County
- Has a bigger lot than 91% of homes in Weston 02493
- Older than 83% of homes in Weston 02493
What homes are worth in Weston 02493
Each bar is how many homes fall in that price range. The marker is this home.
This home is worth more than 85% of homes in Weston 02493.
How it measures up in Weston 02493
The dot is this home. The mark in the middle is the typical home in Weston 02493.
Pricier than 85% of homes nearby
Pricier than 54% of homes nearby
Bigger than 86% of homes nearby
Bigger than 91% of homes nearby
Newer than 17% of homes nearby
| Measure | This home | Weston 02493 | Middlesex County |
|---|---|---|---|
| Estimated valuepricier than | $3,711,085 | 85% of homes | almost all homes |
| Price per ft²pricier than | $684 | 54% of homes | 85% of homes |
| Living areabigger than | 5,426 ft² | 86% of homes | almost all homes |
| Lot sizebigger than | 3.07 ac | 91% of homes | 91% of homes |
| Year builtnewer than | 1934 | 17% of homes | 33% of homes |
About 27 Chestnut St
How much is 27 Chestnut St, Weston, MA worth?
The TopHap Estimate for 27 Chestnut St, Weston, MA is $3,711,085 as of Sep 24, 2026. The likely range is $3,365,398 to $4,056,772. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 27 Chestnut St, Weston, MA last sell?
27 Chestnut St, Weston, MA last sold on Apr 18, 2018 for $2,950,000, according to the county's recorded deed. TopHap holds 2 recorded sales for this parcel.
How big is 27 Chestnut St, Weston, MA?
27 Chestnut St, Weston, MA has 8 bedrooms, 6 bathrooms, 5,426 square feet of living space and a 3.07-acre lot.
When was 27 Chestnut St, Weston, MA built?
27 Chestnut St, Weston, MA was built in 1934, making it 92 years old. It is a colonial home. The building has 2 stories.
What schools serve 27 Chestnut St, Weston, MA?
27 Chestnut St, Weston, MA is assigned to Woodland (elementary), rated A+; Weston High School (high), rated A+; Weston Middle School (middle), rated A+. All sit in Weston School District. Attendance boundaries change — confirm with the district before relying on an assignment.
How does 27 Chestnut St, Weston, MA compare to other homes in Weston 02493?
Among the 3,712 homes in Weston 02493, it is worth more than 85% of them ($3,711,085 against a typical $2,182,760), its price per square foot is higher than 54% of them ($684 against a typical $664), it is bigger than 86% of them (5,426 ft² against a typical 3,339 ft²), its lot is bigger than 91% of them (3.07 ac against a typical 1.38 ac) and it is newer than 17% of them (1934 against a typical 1966). Measured against all of Middlesex County, it is worth more than almost all 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 27 Chestnut St, Weston, MA?
The 2026 property tax bill for 27 Chestnut St, Weston, MA was $40,031. The county assessed it at $3,679,300.
More homes on Chestnut St
- 21 Chestnut St$10M6 bd · 8 ba · 9,310 ft² · Sold $11M · Dec 2025
- 100 Chestnut St$7.7M5 bd · 6.5 ba · 7,064 ft² · Sold $7.3M · Oct 2025
- 70 Chestnut St$1.7M3 bd · 2.5 ba · 3,757 ft² · Sold $1.6M · Aug 2025
- 74 Chestnut St$2M5 bd · 3.5 ba · 3,112 ft² · Sold $1.8M · Apr 2025
- 109 Chestnut St$6.9M7 bd · 8 ba · 7,895 ft² · Sold $8.5M · Jun 2024
- 38 Chestnut St$1.4M4 bd · 2 ba · 2,270 ft² · Sold $700K · Jun 2022
- 84 Chestnut St$4.7M5 bd · 6 ba · 5,644 ft² · Sold $4.7M · Jul 2021
- 55 Chestnut St$5.8M6 bd · 8 ba · 7,948 ft² · Sold $5.1M · Jun 2021
- 34 Chestnut St5 bd · 3 ba · 2,304 ft² · Sold $535K · Oct 2020
- 36 Chestnut St$1.8M3 bd · 2 ba · 1,620 ft² · Sold $680K · Sep 2020
- 40 Chestnut St$1.8M3 bd · 2.5 ba · 3,320 ft² · Sold $1.3M · Jul 2020
- 73 Chestnut St$9.5M7 bd · 10 ba · 8,753 ft² · Sold $2.2M · Dec 2017
Closest homes
- 21 Chestnut St$10M228 ft · 6 bd · 8 ba · 9,310 ft² · Sold $11M · Dec 2025
- 15 Chadwick Rd$4.5M310 ft · 5 bd · 4.5 ba · 4,410 ft² · Sold $1.3M · Nov 1992
- 5 Chadwick Rd$3.1M323 ft · 4 bd · 4 ba · 4,630 ft² · Sold $500K · Dec 2000
- 23 Chadwick Rd$5.3M408 ft · 7 bd · 7 ba · 6,915 ft² · Sold $1.5M · Jul 1995
- 7 Chestnut St$7.8M391 ft · 5 bd · 5 ba · 4,773 ft² · Sold $4.4M · Jul 2000
- 2 Baldwin Cir$3.3M0.1 mi · 5 bd · 7 ba · 4,513 ft² · Sold $2M · Jul 2010
- 40 Chestnut St$1.8M498 ft · 3 bd · 2.5 ba · 3,320 ft² · Sold $1.3M · Jul 2020
- 22 Chadwick Rd$3.6M0.1 mi · 5 bd · 5 ba · 4,560 ft² · Sold $3.4M · Aug 2025
More homes in Weston 02493
- 81 Brook Rd2 bd · 3 ba · 1,634 ft² · Sold $875K · Oct 2026
- 63 Brook Rd$1.3M3 bd · 2.5 ba · 2,097 ft² · Sold $525K · Oct 2026
- 7 Pollywog Ln$2.3M4 bd · 4.5 ba · 4,808 ft² · Sold $4.2M · Oct 2026
- 242 Winter St$1.9M4 bd · 3.5 ba · 3,106 ft² · Sold $1.6M · Sep 2026
- 680 South Ave$1.3M2 bd · 2.5 ba · 1,917 ft² · Sold $1.7M · Sep 2026
- 302 Concord Rd$1.8M4 bd · 2.5 ba · 2,377 ft² · Sold $1.8M · Sep 2026
- 26 Arrowhead Rd$1.5M4 bd · 4 ba · 1,976 ft² · Sold $1.4M · Sep 2026
- 24 Trailside Rd$3.1M4 bd · 4.5 ba · 4,601 ft² · Sold $2.9M · Sep 2026
- 416 Conant Rd$2.4M4 bd · 4.5 ba · 2,676 ft² · Sold $2.3M · Sep 2026
- 40 Hobbs Brook Rd$1.7M3 bd · 2.5 ba · 1,853 ft² · Sold $1.7M · Sep 2026
- 678 Boston Post Rd$985K3 bd · 1.5 ba · 1,656 ft² · Sold $985K · Sep 2026
- 5 Summer St$2M5 bd · 3.5 ba · 4,208 ft² · Sold $1.7M · Sep 2026
Assigned schools
Explore the area
See this home in context
Open 27 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