27 PLEASANT ST
Valuation
Tax & Assessment
Property Facts
Transaction History(11)
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: Milton School District
Neighborhood · ZIP 02186These 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 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 68% of homes in Norfolk County
- Costs less per square foot than 74% of homes in Milton 02186
- Has a bigger lot than 80% of homes in Milton 02186
- Older than 98% of homes in Norfolk County
What homes are worth in Milton 02186
Each bar is how many homes fall in that price range. The marker is this home.
This home is worth more than 35% of homes in Milton 02186.
How it measures up in Milton 02186
The dot is this home. The mark in the middle is the typical home in Milton 02186.
Pricier than 35% of homes nearby
Pricier than 26% of homes nearby
Bigger than 46% of homes nearby
Bigger than 80% of homes nearby
Newer than 3% of homes nearby
| Measure | This home | Milton 02186 | Norfolk County |
|---|---|---|---|
| Estimated valuepricier than | $920,718 | 35% of homes | 68% of homes |
| Price per ft²pricier than | $495 | 26% of homes | 63% of homes |
| Living areabigger than | 1,861 ft² | 46% of homes | 58% of homes |
| Lot sizebigger than | 0.5 ac | 80% of homes | 63% of homes |
| Year builtnewer than | 1874 | 3% of homes | 2% of homes |
About 27 Pleasant St
How much is 27 Pleasant St, Milton, MA worth?
The TopHap Estimate for 27 Pleasant St, Milton, MA is $920,718 as of Aug 30, 2026. The likely range is $884,378 to $957,058. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 27 Pleasant St, Milton, MA last sell?
27 Pleasant St, Milton, MA last sold on Feb 19, 1971, according to the county's recorded deed.
How big is 27 Pleasant St, Milton, MA?
27 Pleasant St, Milton, MA has 3 bedrooms, 3 bathrooms, 1,861 square feet of living space and a 0.50-acre lot.
When was 27 Pleasant St, Milton, MA built?
27 Pleasant St, Milton, MA was built in 1874, making it 152 years old. The building has 2 stories.
What schools serve 27 Pleasant St, Milton, MA?
27 Pleasant St, Milton, MA is assigned to Cunningham School (elementary), rated A; Milton High School (high), rated A+; Charles S Pierce Middle School (middle), rated B. All sit in Milton School District. Attendance boundaries change — confirm with the district before relying on an assignment.
How does 27 Pleasant St, Milton, MA compare to other homes in Milton 02186?
Among the 8,308 homes in Milton 02186, it is worth more than 35% of them ($920,718 against a typical $1,032,698), its price per square foot is higher than 26% of them ($495 against a typical $555), it is bigger than 46% of them (1,861 ft² against a typical 1,938 ft²), its lot is bigger than 80% of them (0.5 ac against a typical 0.18 ac) and it is newer than 3% of them (1874 against a typical 1938). Measured against all of Norfolk County, it is worth more than 68% 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 Pleasant St, Milton, MA?
The 2025 property tax bill for 27 Pleasant St, Milton, MA was $7,879. The county assessed it at $710,500.
More homes on Pleasant St
- 211 Pleasant St$1.3M3 bd · 2 ba · 1,846 ft² · Sold $2.9M · Aug 2026
- 207 Pleasant St$1.6M4 bd · 1.5 ba · 2,490 ft² · Sold $1.6M · Aug 2026
- 98 Pleasant St$728K3 bd · 1 ba · 1,047 ft² · Sold $725K · Jul 2026
- 73 Pleasant St$598K2 bd · 1.5 ba · 981 ft² · Sold $595K · Jul 2026
- 111 Pleasant St # 1134 bd · 5 ba · 2,916 ft² · Sold $1.5M · Jun 2026
- 97 Pleasant St$916K3 bd · 1.5 ba · 1,350 ft² · Sold $900K · Apr 2026
- 639 Pleasant St$792K2 bd · 1.5 ba · 1,471 ft² · Sold $760K · Jan 2026
- 32 Pleasant St$1.3M4 bd · 2.5 ba · 2,504 ft² · Sold $1.2M · Nov 2025
- 418 Pleasant St4 bd · 2 ba · 2,630 ft² · Sold $950K · Oct 2025
- 36 Pleasant St$821K3 bd · 1 ba · 1,004 ft² · Sold $785K · Oct 2025
- 641 Pleasant St$788K2 bd · 1.5 ba · 1,710 ft² · Sold $735K · Aug 2025
- 349 Pleasant St$796K3 bd · 2 ba · 1,654 ft² · Sold $754K · Aug 2025
Closest homes
- 19 Pleasant St78 ft · 4 bd · 2 ba · 2,443 ft²
- 5 Jill Kathleen Ln102 ft · 4 bd · 2.5 ba · 3,240 ft² · Sold $525K · Sep 2017
- 7 Jill Kathleen Ln$1.8M101 ft · 4 bd · 3.5 ba · 3,489 ft² · Sold $525K · May 2017
- 3 Jill Kathleen Ln$1.8M154 ft · 4 bd · 3.5 ba · 3,150 ft² · Sold $1.2M · Jul 2017
- 9 Jill Kathleen Ln$1.9M185 ft · 4 bd · 4.5 ba · 3,530 ft² · Sold Jan 1900
- 26 Pleasant St220 ft · 4 bd · 2 ba · 2,174 ft² · Sold $385K · Nov 2012
- 672 Randolph Ave$867K247 ft · 3 bd · 2 ba · 1,741 ft² · Sold $725K · Nov 2021
- 4 Jill Kathleen Ln$2M248 ft · 4 bd · 3.5 ba · 3,327 ft² · Sold $1.4M · Apr 2019
More homes in Milton 02186
- 51 Bradford Rd$1.4M5 bd · 3.5 ba · 2,992 ft² · Sold $1.7M · Aug 2026
- 91 Atherton St$1.1M4 bd · 1.5 ba · 1,824 ft² · Sold $1000K · Aug 2026
- 82 Dyer Ave$765K3 bd · 1 ba · 1,400 ft² · Sold $765K · Aug 2026
- 213 School St$2.1M4 bd · 3.5 ba · 4,314 ft² · Sold $2.1M · Aug 2026
- 17 Landon Rd$880K3 bd · 1 ba · 1,430 ft² · Sold $880K · Aug 2026
- 88 Wharf St$729K1 bd · 2 ba · 1,297 ft² · Sold $729K · Aug 2026
- 18 Capen St$865K3 bd · 1.5 ba · 1,642 ft² · Sold $725K · Aug 2026
- 285 Brush Hill Rd$1.7M3 bd · 3 ba · 3,803 ft² · Sold $1.7M · Aug 2026
- 79 Hilltop St$1.1M3 bd · 3.5 ba · 2,257 ft² · Sold $1.1M · Aug 2026
- 7 Saint Marys Rd$1M3 bd · 1.5 ba · 1,850 ft² · Sold $1M · Aug 2026
- 52 Nancy Rd$992K3 bd · 1.5 ba · 1,602 ft² · Sold $945K · Aug 2026
- 263 Adams St$2.9M4 bd · 5 ba · 5,062 ft² · Sold $2.9M · Aug 2026
Assigned schools
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