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.
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
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.
- Costs less per square foot than 69% 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 52% 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 52% of homes nearby
Pricier than 44% 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 | $690,355 | 52% of homes | 38% of homes |
| Price per ft²pricier than | $391 | 44% of homes | 31% 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 $690,355 as of Sep 24, 2026. The likely range is $629,284 to $751,426. 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 52% of them ($690,355 against a typical $686,184), its price per square foot is higher than 44% of them ($391 against a typical $404), it is bigger than 47% of them (1,765 ft² against a typical 1,808 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 38% 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.
More homes on Windsor Dr
- 12 Windsor Dr$846K3 bd · 3.5 ba · 1,428 ft² · Sold $810K · Sep 2025
- 20 Windsor Dr$763K3 bd · 2 ba · 2,005 ft² · Sold $483K · Aug 2020
- 17 Windsor Dr$634K2 bd · 1.5 ba · 1,326 ft² · Sold $417K · Nov 2019
- 4 Windsor Dr$617K3 bd · 1.5 ba · 1,142 ft² · Sold $371K · Nov 2017
- 8 Windsor Dr$565K3 bd · 1 ba · 962 ft² · Sold $221K · Jan 2013
- 19 Windsor Dr$615K3 bd · 2.5 ba · 2,144 ft² · Sold $100K · Dec 1996
- 7 Windsor Dr$675K3 bd · 2 ba · 1,524 ft² · Sold Jan 1900
Closest homes
- 12 Windsor Dr$846K103 ft · 3 bd · 3.5 ba · 1,428 ft² · Sold $810K · Sep 2025
- 20 Windsor Dr$763K106 ft · 3 bd · 2 ba · 2,005 ft² · Sold $483K · Aug 2020
- 9 Tudor Ln$581K126 ft · 4 bd · 1 ba · 962 ft² · Sold $350K · Nov 2018
- 5 Tudor Ln$656K162 ft · 2 bd · 2 ba · 1,404 ft² · Sold $605K · Sep 2022
- 17 Windsor Dr$634K184 ft · 2 bd · 1.5 ba · 1,326 ft² · Sold $417K · Nov 2019
- 15 Tudor Ln$634K165 ft · 4 bd · 2.5 ba · 1,382 ft² · Sold $240K · Aug 2014
- 8 Windsor Dr$565K199 ft · 3 bd · 1 ba · 962 ft² · Sold $221K · Jan 2013
- 1 Tudor Ln$666K243 ft · 4 bd · 2 ba · 1,272 ft² · Sold $551K · Oct 2022
More homes in Ashland 01721
- 30 Woodland Rd$450K3 bd · 2 ba · 888 ft² · Sold $470K · Oct 2026
- 14 Running Brook Cir$995K4 bd · 2.5 ba · 3,550 ft² · Sold $975K · Oct 2026
- 60 Algonquin Trl$774K2 bd · 2.5 ba · 1,850 ft² · Sold $546K · Oct 2026
- 254 Captain Eames Cir$667K2 bd · 2.5 ba · 1,758 ft² · Sold $435K · Oct 2026
- 49 Indian Brook Rd$1.3M4 bd · 2.5 ba · 3,187 ft² · Sold $1.3M · Oct 2026
- 8 Voyagers Ln$567K2 bd · 2.5 ba · 1,814 ft² · Sold $575K · Oct 2026
- 17 Metropolitan Ave$700K3 bd · 1.5 ba · 1,558 ft² · Sold $733K · Sep 2026
- 281 Meeting House Path$602K3 bd · 2.5 ba · 1,328 ft² · Sold $430K · Sep 2026
- 60 Cross St$503K3 bd · 1.5 ba · 2,152 ft² · Sold $685K · Sep 2026
- 54 Blue Jay Ln$1.3M4 bd · 4 ba · 3,045 ft² · Sold $350K · Sep 2026
- 30 Rossi Ln$1.2M4 bd · 3.5 ba · 3,262 ft² · Sold $1.1M · Sep 2026
- 33 Half Crown Cir$549K2 bd · 2.5 ba · 2,052 ft² · Sold $540K · Sep 2026
Assigned schools
Explore the area
See this home in context
Open 16 Windsor Dr on TopHap’s interactive map to compare it against every sale nearby, overlay school zones and flood risk, and run a CMA.
Open in map