288 WINTER ST
Valuation
Tax & Assessment
Property Facts
Transaction History(5)
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
288 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 77% of homes in Holliston 01746
- Smaller than 69% of homes in Holliston 01746
- Has a bigger lot than 81% of homes in Middlesex County
- Older than 85% 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 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 64% of homes nearby
Bigger than 31% of homes nearby
Bigger than 66% of homes nearby
Newer than 15% of homes nearby
| Measure | This home | Holliston 01746 | Middlesex County |
|---|---|---|---|
| Estimated valuepricier than | $610,260 | 23% of homes | 26% of homes |
| Price per ft²pricier than | $426 | 64% of homes | 39% of homes |
| Living areabigger than | 1,434 ft² | 31% of homes | 31% of homes |
| Lot sizebigger than | 1 ac | 66% of homes | 81% of homes |
| Year builtnewer than | 1954 | 15% of homes | 45% of homes |
About 288 Winter St
How much is 288 Winter St, Holliston, MA worth?
The TopHap Estimate for 288 Winter St, Holliston, MA is $610,260 as of Jul 14, 2026. The likely range is $582,298 to $638,222. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 288 Winter St, Holliston, MA last sell?
288 Winter St, Holliston, MA last sold on Oct 19, 1990 for $134,000, according to the county's recorded deed.
How big is 288 Winter St, Holliston, MA?
288 Winter St, Holliston, MA has 4 bedrooms, 2.5 bathrooms, 1,434 square feet of living space and a 1.00-acre lot.
When was 288 Winter St, Holliston, MA built?
288 Winter St, Holliston, MA was built in 1954, making it 72 years old. It is a ranch home. The building has 1 story.
What schools serve 288 Winter St, Holliston, MA?
288 Winter St, Holliston, MA is assigned to Placentino Elementary School (elementary); Holliston High School (high), rated A; 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 288 Winter 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 ($610,260 against a typical $726,992), its price per square foot is higher than 64% of them ($426 against a typical $390), it is bigger than 31% of them (1,434 ft² against a typical 1,897 ft²), its lot is bigger than 66% of them (1 ac against a typical 0.7 ac) and it is newer than 15% of them (1954 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 288 Winter St, Holliston, MA?
The 2025 property tax bill for 288 Winter St, Holliston, MA was $7,435. The county assessed it at $507,500.
Closest homes
- 20 Winter St$955K0 ft · 4 bd · 3 ba · 2,675 ft² · Sold $290K · Jun 1995
- 168 Winter St$672K371 ft · 4 bd · 2 ba · 1,936 ft² · Sold $148K · May 1995
- 160 Winter St$743K354 ft · 3 bd · 2.5 ba · 1,894 ft² · Sold $720K · Mar 2026
- 180 Winter St$811K471 ft · 4 bd · 2.5 ba · 2,380 ft² · Sold $269K · Dec 1998
- 132 Winter St$778K386 ft · 4 bd · 2.5 ba · 2,208 ft² · Sold Jan 1900
- 62 Winter St$1.6M0.1 mi · 4 bd · 4 ba · 4,208 ft² · Sold Jan 2018
- 190 Winter St$1.2M454 ft · 3 bd · 3.5 ba · 3,394 ft² · Sold Jan 1900
- 200 Winter St$617K0.1 mi · 3 bd · 1.5 ba · 1,604 ft² · Sold $192K · Jul 1994
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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