559 WINTER ST
Valuation
Tax & Assessment
Climate Risk
Scores 0–100; higher = greater projected risk.
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: 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.
Ownership
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
559 Winter 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 81% of homes in Holliston 01746
- Costs less per square foot than 84% of homes in Middlesex County
- Has a bigger lot than 84% of homes in Middlesex County
- Older than 93% of homes in Holliston 01746
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 19% 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 19% of homes nearby
Pricier than 22% of homes nearby
Bigger than 45% of homes nearby
Bigger than 72% of homes nearby
Newer than 7% of homes nearby
| Measure | This home | Holliston 01746 | Middlesex County |
|---|---|---|---|
| Estimated valuepricier than | $584,499 | 19% of homes | 23% of homes |
| Price per ft²pricier than | $338 | 22% of homes | 16% of homes |
| Living areabigger than | 1,729 ft² | 45% of homes | 45% of homes |
| Lot sizebigger than | 1.2 ac | 72% of homes | 84% of homes |
| Year builtnewer than | 1900 | 7% of homes | 15% of homes |
About 559 Winter St
How much is 559 Winter St, Holliston, MA worth?
The TopHap Estimate for 559 Winter St, Holliston, MA is $584,499 as of Jul 14, 2026. The likely range is $558,627 to $610,371. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 559 Winter St, Holliston, MA last sell?
559 Winter St, Holliston, MA last sold on Jan 1, 1900, according to the county's recorded deed.
How big is 559 Winter St, Holliston, MA?
559 Winter St, Holliston, MA has 3 bedrooms, 2 bathrooms, 1,729 square feet of living space and a 1.20-acre lot.
When was 559 Winter St, Holliston, MA built?
559 Winter St, Holliston, MA was built in 1900, making it 126 years old. It is a conventional home. The building has 3 stories.
What schools serve 559 Winter St, Holliston, MA?
559 Winter St, Holliston, MA is assigned to Holliston High School (high), rated A; Placentino Elementary School (elementary); Robert H. Adams Middle School (middle), rated A-. All sit in Holliston School District. Attendance boundaries change — confirm with the district before relying on an assignment.
How does 559 Winter St, Holliston, MA compare to other homes in Holliston 01746?
Among the 5,229 homes in Holliston 01746, it is worth more than 19% of them ($584,499 against a typical $726,039), its price per square foot is higher than 22% of them ($338 against a typical $390), it is bigger than 45% of them (1,729 ft² against a typical 1,901 ft²), its lot is bigger than 72% of them (1.2 ac against a typical 0.7 ac) and it is newer than 7% of them (1900 against a typical 1968). Measured against all of Middlesex County, it is worth more than 23% 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 559 Winter St, Holliston, MA?
The 2025 property tax bill for 559 Winter St, Holliston, MA was $6,068. The county assessed it at $414,200.
Closest homes
- 571 Winter St$436K285 ft · 1 bd · 1 ba · 572 ft² · Sold $30K · Oct 1986
- 542 Winter St$787K240 ft · 3 bd · 2 ba · 1,658 ft² · Sold $58K · May 1978
- 562 Winter St$606K281 ft · 3 bd · 1.5 ba · 1,144 ft² · Sold $300K · Jun 2003
- 525 Winter St$486K362 ft · 2 bd · 1 ba · 756 ft² · Sold $291K · Oct 2007
- 576 Winter St$710K409 ft · 3 bd · 2.5 ba · 1,194 ft² · Sold $400K · Jun 2017
- 583 Winter St$980K486 ft · 3 bd · 3.5 ba · 2,519 ft² · Sold Oct 2017
- 31 Westfield Dr$753K524 ft · 4 bd · 1.5 ba · 1,728 ft² · Sold $322K · Jan 2012
- 521 Winter St$582K524 ft · 4 bd · 2.5 ba · 1,092 ft² · Sold $172K · Apr 1999
More homes in Holliston 01746
- 15 Saddle Ridge Rd$1.4M4 bd · 2.5 ba · 3,040 ft² · Sold $1.4M · Jul 2026
- 147 Turner Rd$215K1 bd · 1.5 ba · 702 ft² · Sold $215K · Jul 2026
- 140 Goulding St$1.1M5 bd · 3 ba · 3,084 ft² · Sold $1.1M · Jul 2026
- 135 Locust St$675K2 bd · 1 ba · 1,547 ft² · Sold $675K · Jul 2026
- 157 Rolling Meadow Dr$950K4 bd · 2.5 ba · 2,449 ft² · Sold $930K · Jul 2026
- 55 Concord St$1.1M5 bd · 4 ba · 4,214 ft² · Sold $1M · Jul 2026
- 3 Danforth Dr0.76 ac · Sold $1.6M · Jul 2026
- 5 Short Rd$658K4 bd · 3 ba · 1,897 ft² · Sold $1.4M · Jul 2026
- 48 N Mill St7 bd · 4 ba · 1,450 ft² · Sold $1.1M · Jul 2026
- 6 Trailside Ct$820K2 bd · 2.5 ba · 2,248 ft² · Sold $860K · Jul 2026
- 125 Hemlock Dr$725K3 bd · 2 ba · 1,428 ft² · Sold $720K · Jul 2026
- 40 Union St$704K3 bd · 1.5 ba · 1,689 ft² · Sold $670K · Jul 2026
Assigned schools
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