27 PLEASANT ST
Valuation
Tax & Assessment
Climate Risk
Scores 0–100; higher = greater projected risk.
Property Facts
Transaction History(16)
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: Holliston School District
Neighborhood · ZIP 01746These 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 less than 77% of homes in Holliston 01746
- Smaller than 68% of homes in Holliston 01746
- Has a smaller lot than 96% of homes in Holliston 01746
- Older than 98% of homes in Middlesex County
What homes are worth in Holliston 01746
Each bar is how many homes fall in that price range. The marker is this home.
This home is worth more than 23% of homes in Holliston 01746.
How it measures up in Holliston 01746
The dot is this home. The mark in the middle is the typical home in Holliston 01746.
Pricier than 23% of homes nearby
Pricier than 63% of homes nearby
Bigger than 32% of homes nearby
Bigger than 4% of homes nearby
Newer than 3% of homes nearby
| Measure | This home | Holliston 01746 | Middlesex County |
|---|---|---|---|
| Estimated valuepricier than | $603,325 | 23% of homes | 26% of homes |
| Price per ft²pricier than | $418 | 63% of homes | 38% of homes |
| Living areabigger than | 1,444 ft² | 32% of homes | 32% of homes |
| Lot sizebigger than | 0.26 ac | 4% of homes | 44% of homes |
| Year builtnewer than | 1865 | 3% of homes | 2% of homes |
About 27 Pleasant St
How much is 27 Pleasant St, Holliston, MA worth?
The TopHap Estimate for 27 Pleasant St, Holliston, MA is $603,325 as of Sep 24, 2026. The likely range is $571,085 to $635,565. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 27 Pleasant St, Holliston, MA last sell?
27 Pleasant St, Holliston, MA last sold on Dec 17, 2015 for $381,000, according to the county's recorded deed. TopHap holds 5 recorded sales for this parcel.
How big is 27 Pleasant St, Holliston, MA?
27 Pleasant St, Holliston, MA has 3 bedrooms, 1.5 bathrooms, 1,444 square feet of living space and a 0.26-acre lot.
When was 27 Pleasant St, Holliston, MA built?
27 Pleasant St, Holliston, MA was built in 1865, making it 161 years old. It is a conventional home. The building has 2 stories.
What schools serve 27 Pleasant St, Holliston, MA?
27 Pleasant St, Holliston, MA is assigned to Robert H. Adams Middle School (middle), rated A; Holliston High School (high), rated A-; Placentino Elementary School (elementary). All sit in Holliston School District. Attendance boundaries change — confirm with the district before relying on an assignment.
How does 27 Pleasant St, Holliston, MA compare to other homes in Holliston 01746?
Among the 5,229 homes in Holliston 01746, it is worth more than 23% of them ($603,325 against a typical $719,548), its price per square foot is higher than 63% of them ($418 against a typical $387), it is bigger than 32% of them (1,444 ft² against a typical 1,890 ft²), its lot is bigger than 4% of them (0.26 ac against a typical 0.7 ac) and it is newer than 3% of them (1865 against a typical 1968). Measured against all of Middlesex County, it is worth more than 26% 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, Holliston, MA?
The 2025 property tax bill for 27 Pleasant St, Holliston, MA was $8,484. The county assessed it at $579,100.
More homes on Pleasant St
- 41 Pleasant St$1.1M4 bd · 2.5 ba · 2,924 ft² · Sold $1.1M · Jul 2025
- 36 Pleasant St$740K3 bd · 2.5 ba · 1,794 ft² · Sold $700K · Aug 2024
- 67 Pleasant St$647K5 bd · 2 ba · 1,729 ft² · Sold $607K · Aug 2024
- 51 Pleasant St$399K2 bd · 1 ba · 882 ft² · Sold $350K · Mar 2024
- 59 Pleasant St$838K3 bd · 3.5 ba · 2,544 ft² · Sold Jan 2018
- 28 Pleasant St$607K3 bd · 2 ba · 1,631 ft² · Sold $438K · Jun 2015
- 19 Pleasant St$767K3 bd · 2 ba · 2,183 ft² · Sold $375K · Aug 2010
- 35 Pleasant St5 bd · 3 ba · 2,160 ft² · Sold $161K · Jul 1997
- 22 Pleasant St$757K3 bd · 2.5 ba · 2,593 ft² · Sold $155K · May 1994
- 11 Pleasant St$658K4 bd · 2 ba · 1,759 ft² · Sold $30K · Jul 1978
- 45 Pleasant St$670K3 bd · 2.5 ba · 2,195 ft² · Sold Jan 1900
- 50 Pleasant St$642K2 bd · 2 ba · 1,786 ft² · Sold Jan 1900
Closest homes
- 19 Pleasant St$767K93 ft · 3 bd · 2 ba · 2,183 ft² · Sold $375K · Aug 2010
- 35 Pleasant St142 ft · 5 bd · 3 ba · 2,160 ft² · Sold $161K · Jul 1997
- 28 Pleasant St$607K172 ft · 3 bd · 2 ba · 1,631 ft² · Sold $438K · Jun 2015
- 41 Pleasant St$1.1M188 ft · 4 bd · 2.5 ba · 2,924 ft² · Sold $1.1M · Jul 2025
- 11 Pleasant St$658K205 ft · 4 bd · 2 ba · 1,759 ft² · Sold $30K · Jul 1978
- 22 Pleasant St$757K240 ft · 3 bd · 2.5 ba · 2,593 ft² · Sold $155K · May 1994
- 36 Pleasant St$740K215 ft · 3 bd · 2.5 ba · 1,794 ft² · Sold $700K · Aug 2024
- 908 Washington St277 ft · 3 bd · 2 ba · 2,112 ft² · Sold $750K · Jul 2024
More homes in Holliston 01746
- 66 Lakeshore Dr$404K3 bd · 1 ba · 1,060 ft² · Sold $310K · Oct 2026
- 1804 Washington St$795K2 bd · 2 ba · 2,358 ft² · Sold $785K · Oct 2026
- 208 Mohawk Path$1.4M4 bd · 4.5 ba · 4,440 ft² · Sold $1.4M · Sep 2026
- 47 Westfield Dr$785K4 bd · 2.5 ba · 1,932 ft² · Sold $785K · Sep 2026
- 21 Foxwood Cv$1.2M4 bd · 3.5 ba · 2,982 ft² · Sold $1.1M · Sep 2026
- 33 Copper Ln$675K3 bd · 2 ba · 1,190 ft² · Sold $670K · Sep 2026
- 152 Turner Rd$210K1 bd · 1.5 ba · 698 ft² · Sold $215K · Sep 2026
- 65 Briarcliff Ln$850K3 bd · 2 ba · 1,888 ft² · Sold $835K · Sep 2026
- 10 Winston Rd$1.1M4 bd · 3 ba · 3,648 ft² · Sold $1.1M · Sep 2026
- 361 Winter St$982K4 bd · 2.5 ba · 2,264 ft² · Sold $980K · Aug 2026
- 54 Jarbrook Rd$802K4 bd · 2 ba · 1,736 ft² · Sold $800K · Aug 2026
- 100 Marilyn St$691K3 bd · 2 ba · 1,393 ft² · Sold $689K · Aug 2026
Assigned schools
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