16 WINDSOR DR
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.Foreclosure Filings(2)
Assigned SchoolsThe public schools this address is zoned for. Boundaries change, so confirm with the district before you count on it.
District: Ashland School District
Neighborhood · ZIP 01721These 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
16 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.
- Worth less than 68% of homes in Middlesex County
- Costs less per square foot than 76% of homes in Middlesex County
- Has a smaller lot than 87% of homes in Ashland 01721
- Older than 75% of homes in Ashland 01721
What homes are worth in Ashland 01721
Each bar is how many homes fall in that price range. The marker is this home.
This home is worth more than 44% of homes in Ashland 01721.
How it measures up in Ashland 01721
The dot is this home. The mark in the middle is the typical home in Ashland 01721.
Pricier than 44% of homes nearby
Pricier than 34% of homes nearby
Bigger than 47% of homes nearby
Bigger than 13% of homes nearby
Newer than 25% of homes nearby
| Measure | This home | Ashland 01721 | Middlesex County |
|---|---|---|---|
| Estimated valuepricier than | $653,220 | 44% of homes | 32% of homes |
| Price per ft²pricier than | $370 | 34% of homes | 24% of homes |
| Living areabigger than | 1,765 ft² | 47% of homes | 47% of homes |
| Lot sizebigger than | 0.34 ac | 13% of homes | 52% of homes |
| Year builtnewer than | 1958 | 25% of homes | 50% of homes |
About 16 Windsor Dr
How much is 16 Windsor Dr, Ashland, MA worth?
The TopHap Estimate for 16 Windsor Dr, Ashland, MA is $653,220 as of Jul 14, 2026. The likely range is $604,053 to $702,387. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 16 Windsor Dr, Ashland, MA last sell?
16 Windsor Dr, Ashland, MA last sold on Dec 28, 2015 for $291,000, according to the county's recorded deed. TopHap holds 2 recorded sales for this parcel.
How big is 16 Windsor Dr, Ashland, MA?
16 Windsor Dr, Ashland, MA has 5 bedrooms, 2 bathrooms, 1,765 square feet of living space and a 0.34-acre lot.
When was 16 Windsor Dr, Ashland, MA built?
16 Windsor Dr, Ashland, MA was built in 1958, making it 68 years old. The building has 2 stories.
What schools serve 16 Windsor Dr, Ashland, MA?
16 Windsor Dr, Ashland, MA is assigned to Henry E Warren Elementary School (elementary); Ashland High School (high), rated A; Ashland Middle School (middle), rated A. All sit in Ashland School District. Attendance boundaries change — confirm with the district before relying on an assignment.
How does 16 Windsor Dr, Ashland, MA compare to other homes in Ashland 01721?
Among the 6,092 homes in Ashland 01721, it is worth more than 44% of them ($653,220 against a typical $683,354), its price per square foot is higher than 34% of them ($370 against a typical $390), it is bigger than 47% of them (1,765 ft² against a typical 1,792 ft²), its lot is bigger than 13% of them (0.34 ac against a typical 0.73 ac) and it is newer than 25% of them (1958 against a typical 1984). Measured against all of Middlesex County, it is worth more than 32% 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 16 Windsor Dr, Ashland, MA?
The 2025 property tax bill for 16 Windsor Dr, Ashland, MA was $7,057. The county assessed it at $552,600.
Closest homes
- 12 Windsor Dr$841K103 ft · 3 bd · 3.5 ba · 1,428 ft² · Sold $810K · Sep 2025
- 20 Windsor Dr$761K106 ft · 3 bd · 2 ba · 2,005 ft² · Sold $483K · Aug 2020
- 9 Tudor Ln$552K126 ft · 4 bd · 1 ba · 962 ft² · Sold $350K · Nov 2018
- 5 Tudor Ln$647K162 ft · 2 bd · 2 ba · 1,404 ft² · Sold $605K · Sep 2022
- 17 Windsor Dr$630K184 ft · 2 bd · 1.5 ba · 1,326 ft² · Sold $417K · Nov 2019
- 15 Tudor Ln$592K165 ft · 4 bd · 2.5 ba · 1,382 ft² · Sold $240K · Aug 2014
- 8 Windsor Dr$578K199 ft · 3 bd · 1 ba · 962 ft² · Sold $221K · Jan 2013
- 1 Tudor Ln$633K243 ft · 4 bd · 2 ba · 1,272 ft² · Sold $551K · Oct 2022
More homes in Ashland 01721
- 89 Leland Farm Rd$531K2 bd · 1.5 ba · 1,316 ft² · Sold $493K · Jul 2026
- 26 Christy Ln$995K4 bd · 2.5 ba · 2,304 ft² · Sold $1.1M · Jul 2026
- 41 Lincoln Rd$747K2 bd · 1.5 ba · 1,932 ft² · Sold $850K · Jul 2026
- 219 Prospect St$599K3 bd · 2 ba · 1,386 ft² · Sold $617K · Jul 2026
- 33 Birch Hill Rd$635K3 bd · 2 ba · 1,600 ft² · Sold $730K · Jul 2026
- 9 Running Brook Cir$875K3 bd · 2.5 ba · 2,015 ft² · Sold $1M · Jul 2026
- 10 Roberts Rd$399K3 bd · 2 ba · 1,260 ft² · Sold $350K · Jul 2026
- 217 Meeting House Path$516K3 bd · 2.5 ba · 1,332 ft² · Sold $495K · Jul 2026
- 60 Cross St$789K3 bd · 1.5 ba · 2,152 ft² · Sold $500K · Jul 2026
- 4 Indian Brook Rd$995K4 bd · 2.5 ba · 2,871 ft² · Sold $1.1M · Jul 2026
- 29 Carriage House Path$800K3 bd · 2 ba · 2,198 ft² · Sold $860K · Jul 2026
- 8 Blue Jay Ln$973K4 bd · 2.5 ba · 2,732 ft² · Sold $1.2M · Jul 2026
Assigned schools
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