27 CHESTNUT ST
Valuation
Tax & Assessment
Property Facts
Transaction History(20)
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: Boston School District
Neighborhood · ZIP 02108These 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.
- Worth more than 94% of homes in Suffolk County
- Costs more per square foot than 93% of homes in Suffolk County
- Has a bigger lot than 86% of homes in Beacon Hill
- Older than 94% of homes in Suffolk County
What homes are worth in Boston 02108
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 Boston 02108.
How it measures up in Boston 02108
The dot is this home. The mark in the middle is the typical home in Boston 02108.
Pricier than 56% of homes nearby
Pricier than 43% of homes nearby
Bigger than 55% of homes nearby
Bigger than 75% of homes nearby
Newer than 29% of homes nearby
| Measure | This home | Beacon Hill | Boston 02108 | Suffolk County |
|---|---|---|---|---|
| Estimated valuepricier than | $1,952,681 | 68% of homes | 56% of homes | 94% of homes |
| Price per ft²pricier than | $1401 | 50% of homes | 43% of homes | 93% of homes |
| Living areabigger than | 1,394 ft² | 64% of homes | 55% of homes | 47% of homes |
| Lot sizebigger than | 1,675 ft² | 86% of homes | 75% of homes | 41% of homes |
| Year builtnewer than | 1880 | 26% of homes | 29% of homes | 6% of homes |
About 27 Chestnut St
How much is 27 Chestnut St, Boston, MA worth?
The TopHap Estimate for 27 Chestnut St, Boston, MA is $1,952,681 as of Aug 30, 2026. The likely range is $1,536,020 to $2,369,342. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 27 Chestnut St, Boston, MA last sell?
27 Chestnut St, Boston, MA last sold on Jun 5, 2026 for $1,955,000, according to the county's recorded deed. TopHap holds 11 recorded sales for this parcel.
How big is 27 Chestnut St, Boston, MA?
27 Chestnut St, Boston, MA has 2 bedrooms, 2 bathrooms, 1,394 square feet of living space and a 0.04-acre lot.
When was 27 Chestnut St, Boston, MA built?
27 Chestnut St, Boston, MA was built in 1880, making it 146 years old. The building has 2 stories.
What schools serve 27 Chestnut St, Boston, MA?
27 Chestnut St, Boston, MA is assigned to Boston Adult Technical Academy (high); Josiah Quincy Elementary School (elementary), rated B; Quincy Upper School (middle), rated D. All sit in Boston School District. Attendance boundaries change — confirm with the district before relying on an assignment.
How does 27 Chestnut St, Boston, MA compare to other homes in Boston 02108?
Among the 1,489 homes in Boston 02108, it is worth more than 56% of them ($1,952,681 against a typical $1,652,009), its price per square foot is higher than 43% of them ($1401 against a typical $1446), it is bigger than 55% of them (1,394 ft² against a typical 1,291 ft²), its lot is bigger than 75% of them (1,675 ft² against a typical 1,133 ft²) and it is newer than 29% of them (1880 against a typical 1899). Measured against all of Suffolk County, it is worth more than 94% 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 27 Chestnut St, Boston, MA?
The 2025 property tax bill for 27 Chestnut St, Boston, MA was $18,805. The county assessed it at $1,623,900.
More homes on Chestnut St
- 33 Chestnut St # 5$1.2M1 bd · 1 ba · 1,440 ft² · Sold $2.8M · Aug 2026
- 107 Chestnut St # 3$4M2 bd · 2.5 ba · 2,180 ft² · Sold $4M · Jul 2026
- 41 Chestnut St$5.6M5 bd · 4 ba · 3,849 ft² · Sold $5.6M · Jul 2026
- 62 Chestnut St$7M5 bd · 6.5 ba · 3,765 ft² · Sold $7M · Jul 2026
- 92 Chestnut St # 92a5,280 ft² · Sold $5.5M · Jun 2026
- 104 Chestnut St4 bd · 3.5 ba · 3,021 ft² · Sold $4.6M · Jun 2026
- 107 Chestnut St # 5$8.6M2 bd · 2.5 ba · 2,928 ft² · Sold $8.6M · Jun 2026
- 109 Chestnut St # 5$2M1 bd · 1 ba · 718 ft² · Sold $2M · Jun 2026
- 32 Chestnut St # 1$3.3M2 bd · 2 ba · 2,095 ft² · Sold $3.3M · May 2026
- 32 Chestnut St # 2$2.9M4 bd · 2 ba · 2,244 ft² · Sold $2.9M · May 2026
- 82 Chestnut St # 30$1.8M2 bd · 1 ba · 1,260 ft² · Sold $1.8M · Apr 2026
- 46 Chestnut St$10M6 bd · 8.5 ba · 6,682 ft² · Sold $22M · Feb 2026
Closest homes
- 70 Mount Vernon St$1.3M0 ft · 2 bd · 1 ba · 1,019 ft² · Sold Jan 1900
- 70 Mount Vernon St$2.3M0 ft · 2 bd · 2.5 ba · 1,673 ft² · Sold $1.1M · Sep 2010
- 70 Mount Vernon St$1.6M0 ft · 1 bd · 1 ba · 835 ft² · Sold Jan 2017
- 70 Mount Vernon St$3.7M0 ft · 2 bd · 2.5 ba · 2,176 ft² · Sold $3.2M · Sep 2016
- 70 Mount Vernon St$6.3M0 ft · 5 bd · 4.5 ba · 4,035 ft² · Sold $9.8M · Jul 2021
- 70 Mount Vernon St$2.6M0 ft · 2 bd · 2 ba · 1,612 ft² · Sold $940K · Sep 2001
- 70 Mount Vernon St$1.1M0 ft · 2 bd · 1 ba · 833 ft² · Sold $320K · Jun 1999
- 70 Mount Vernon St$2.3M0 ft · 3 bd · 2 ba · 1,674 ft² · Sold $925K · Jan 1999
More homes in Boston 02108
- 46 Beacon St39,917 ft² · Sold $9M · Sep 2026
- 21 Beacon St$456K1 bd · 1 ba · 535 ft² · Sold $619K · Sep 2026
- 92 Beacon St$1.4M2 bd · 2 ba · 1,019 ft² · Sold $1.3M · Sep 2026
- 15 River St$850K1 bd · 1 ba · 721 ft² · Sold $820K · Aug 2026
- 22 River St$985K1 bd · 1 ba · 700 ft² · Sold $950K · Aug 2026
- 10 Byron St$4.5M2 bd · 4 ba · 2,436 ft² · Sold $6.5M · Aug 2026
- 101 Mount Vernon St$2.6M2 bd · 2 ba · 1,414 ft² · Sold $2.6M · Aug 2026
- 21 Beacon St$565K1 bd · 1 ba · 588 ft² · Sold $565K · Aug 2026
- 25 Beacon St$8.4M3 bd · 3.5 ba · 3,578 ft² · Sold $8.4M · Aug 2026
- 48 Beacon St$1.8M2 bd · 1.5 ba · 1,448 ft² · Sold $1.8M · Aug 2026
- 48 Beacon St$1.1M1 bd · 1 ba · 779 ft² · Sold $1.1M · Jul 2026
- 63 Mount Vernon St$4M2 bd · 2.5 ba · 2,317 ft² · Sold $4M · Jul 2026
Assigned schools
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