49 WINDSOR DR
Valuation
Tax & Assessment
Climate Risk
Scores 0–100; higher = greater projected risk.
Property Facts
Transaction History(3)
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
49 Windsor Dr 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.
- Among the least valuable homes in Middlesex County
- Costs less per square foot than 82% of homes in Middlesex County
- Among the smallest homes in Holliston 01746
- Has a bigger lot than 91% 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 2% 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 2% of homes nearby
Pricier than 25% of homes nearby
Smaller than almost all homes nearby
Bigger than 85% of homes nearby
Newer than 57% of homes nearby
| Measure | This home | Holliston 01746 | Middlesex County |
|---|---|---|---|
| Estimated valuepricier than | $227,520 | 2% of homes | almost no homes |
| Price per ft²pricier than | $343 | 25% of homes | 18% of homes |
| Living areabigger than | 664 ft² | almost no homes | 2% of homes |
| Lot sizebigger than | 2.71 ac | 85% of homes | 91% of homes |
| Year builtnewer than | 1970 | 57% of homes | 64% of homes |
About 49 Windsor Dr
How much is 49 Windsor Dr, Holliston, MA worth?
The TopHap Estimate for 49 Windsor Dr, Holliston, MA is $227,520 as of Sep 24, 2026. The likely range is $210,642 to $244,398. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 49 Windsor Dr, Holliston, MA last sell?
49 Windsor Dr, Holliston, MA last sold on Oct 29, 2013 for $110,000, according to the county's recorded deed. TopHap holds 2 recorded sales for this parcel.
How big is 49 Windsor Dr, Holliston, MA?
49 Windsor Dr, Holliston, MA has 1 bedrooms, 1.5 bathrooms and 664 square feet of living space.
When was 49 Windsor Dr, Holliston, MA built?
49 Windsor Dr, Holliston, MA was built in 1970, making it 56 years old. The building has 1 story.
What schools serve 49 Windsor Dr, Holliston, MA?
49 Windsor Dr, Holliston, MA is assigned to Placentino Elementary School (elementary); Robert H. Adams Middle School (middle), rated A; Holliston High School (high), rated A-. All sit in Holliston School District. Attendance boundaries change — confirm with the district before relying on an assignment.
How does 49 Windsor Dr, Holliston, MA compare to other homes in Holliston 01746?
Among the 5,229 homes in Holliston 01746, it is worth more than 2% of them ($227,520 against a typical $718,255), its price per square foot is higher than 25% of them ($343 against a typical $387), it is bigger than almost none of them (664 ft² against a typical 1,901 ft²), its lot is bigger than 85% of them (2.71 ac against a typical 0.7 ac) and it is newer than 57% of them (1970 against a typical 1968). Measured against all of Middlesex County, it is worth more than almost no 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 49 Windsor Dr, Holliston, MA?
The 2025 property tax bill for 49 Windsor Dr, Holliston, MA was $2,825. The county assessed it at $192,800.
More homes on Windsor Dr
- 49 Windsor Dr # 105$272K2 bd · 1.5 ba · 851 ft² · Sold $293K · Jun 2025
- 49 Windsor Dr # 307$244K2 bd · 1.5 ba · 960 ft² · Sold $270K · Oct 2024
- 49 Windsor Dr # 108$248K1 bd · 1.5 ba · 743 ft² · Sold $275K · Oct 2024
- 49 Windsor Dr # 102$205K1 bd · 1.5 ba · 654 ft² · Sold $220K · Jul 2024
- 49 Windsor Dr # 106$356K3 bd · 1.5 ba · 1,088 ft² · Sold $285K · May 2022
- 30 Windsor Dr$813K4 bd · 1.5 ba · 2,319 ft² · Sold $595K · Sep 2021
- 49 Windsor Dr # 204$274K2 bd · 1.5 ba · 852 ft² · Sold $200K · Jun 2021
- 49 Windsor Dr # 310$294K2 bd · 1.5 ba · 860 ft² · Sold $215K · Jun 2021
- 49 Windsor Dr # 308$334K2 bd · 1.5 ba · 938 ft² · Sold $240K · Apr 2021
- 17 Windsor Dr # D$310K2 bd · 1 ba · 999 ft² · Sold $235K · Mar 2021
- 49 Windsor Dr # 109$288K2 bd · 1.5 ba · 850 ft² · Sold $189K · Dec 2020
- 49 Windsor Dr # 309$279K2 bd · 1.5 ba · 860 ft² · Sold $190K · Jul 2020
Closest homes
- 49 Windsor Dr$304K0 ft · 2 bd · 1.5 ba · 933 ft² · Sold $26K · Feb 1996
- 49 Windsor Dr$229K0 ft · 1 bd · 1.5 ba · 669 ft² · Sold $150K · Mar 2005
- 49 Windsor Dr$272K0 ft · 2 bd · 1.5 ba · 853 ft² · Sold $136K · Sep 2010
- 49 Windsor Dr$226K0 ft · 1 bd · 1.5 ba · 672 ft² · Sold $119K · Nov 2017
- 49 Windsor Dr$244K0 ft · 2 bd · 1.5 ba · 960 ft² · Sold $270K · Oct 2024
- 49 Windsor Dr$288K0 ft · 2 bd · 1.5 ba · 880 ft² · Sold $130K · Jun 2016
- 49 Windsor Dr$293K0 ft · 2 bd · 1.5 ba · 867 ft² · Sold $99K · Mar 1988
- 49 Windsor Dr$286K0 ft · 2 bd · 1.5 ba · 852 ft² · Sold $141K · May 2003
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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