18 WINESAP RD
Valuation
Tax & Assessment
Property Facts
Transaction History(6)
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: Pittsfield School District
Neighborhood · ZIP 01201These 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
18 Winesap Rd 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 more than 83% of homes in Pittsfield 01201
- Bigger than 71% of homes in Pittsfield 01201
- Has a bigger lot than 69% of homes in Pittsfield 01201
- Newer than 87% of homes in Pittsfield 01201
What homes are worth in Pittsfield 01201
Each bar is how many homes fall in that price range. The marker is this home.
This home is worth more than 83% of homes in Pittsfield 01201.
How it measures up in Pittsfield 01201
The dot is this home. The mark in the middle is the typical home in Pittsfield 01201.
Pricier than 83% of homes nearby
Pricier than 55% of homes nearby
Bigger than 71% of homes nearby
Bigger than 69% of homes nearby
Newer than 87% of homes nearby
| Measure | This home | Pittsfield 01201 | Berkshire County |
|---|---|---|---|
| Estimated valuepricier than | $448,790 | 83% of homes | 61% of homes |
| Price per ft²pricier than | $220 | 55% of homes | 38% of homes |
| Living areabigger than | 2,037 ft² | 71% of homes | 67% of homes |
| Lot sizebigger than | 0.33 ac | 69% of homes | 38% of homes |
| Year builtnewer than | 1980 | 87% of homes | 75% of homes |
About 18 Winesap Rd
How much is 18 Winesap Rd, Pittsfield, MA worth?
The TopHap Estimate for 18 Winesap Rd, Pittsfield, MA is $448,790 as of Aug 30, 2026. The likely range is $429,246 to $468,334. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 18 Winesap Rd, Pittsfield, MA last sell?
18 Winesap Rd, Pittsfield, MA last sold on Aug 4, 2000 for $146,900, according to the county's recorded deed.
How big is 18 Winesap Rd, Pittsfield, MA?
18 Winesap Rd, Pittsfield, MA has 2 bedrooms, 2 bathrooms, 2,037 square feet of living space and a 0.33-acre lot.
When was 18 Winesap Rd, Pittsfield, MA built?
18 Winesap Rd, Pittsfield, MA was built in 1980, making it 46 years old. It is a cape cod home. The building has 2 stories.
What schools serve 18 Winesap Rd, Pittsfield, MA?
18 Winesap Rd, Pittsfield, MA is assigned to Williams (elementary), rated B; Theodore Herberg Middle School (middle), rated D-; Pittsfield High School (high), rated C. All sit in Pittsfield School District. Attendance boundaries change — confirm with the district before relying on an assignment.
How does 18 Winesap Rd, Pittsfield, MA compare to other homes in Pittsfield 01201?
Among the 14,716 homes in Pittsfield 01201, it is worth more than 83% of them ($448,790 against a typical $301,330), its price per square foot is higher than 55% of them ($220 against a typical $214), it is bigger than 71% of them (2,037 ft² against a typical 1,570 ft²), its lot is bigger than 69% of them (0.33 ac against a typical 0.24 ac) and it is newer than 87% of them (1980 against a typical 1944). Measured against all of Berkshire County, it is worth more than 61% 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 18 Winesap Rd, Pittsfield, MA?
The 2025 property tax bill for 18 Winesap Rd, Pittsfield, MA was $7,612. The county assessed it at $424,300.
More homes on Winesap Rd
- 86 Winesap Rd$423K1 bd · 3 ba · 2,299 ft² · Sold $415K · Mar 2026
- 78 Winesap Rd$384K3 bd · 2 ba · 1,530 ft² · Sold $365K · Jul 2025
- 15 Winesap Rd$457K3 bd · 2 ba · 1,368 ft² · Sold $427K · Mar 2025
- 6 Winesap Rd$431K3 bd · 2 ba · 1,934 ft² · Sold Mar 2024
- 12 Winesap Rd$389K3 bd · 2 ba · 1,494 ft² · Sold $360K · Nov 2023
- 66 Winesap Rd$438K3 bd · 2 ba · 2,200 ft² · Sold $387K · Oct 2023
- 94 Winesap Rd$469K4 bd · 4 ba · 2,676 ft² · Sold $423K · Feb 2023
- 27 Winesap Rd$368K4 bd · 2 ba · 1,468 ft² · Sold $311K · Nov 2022
- 36 Winesap Rd$371K3 bd · 2.5 ba · 1,720 ft² · Sold $279K · Oct 2021
- 48 Winesap Rd$407K3 bd · 2 ba · 1,634 ft² · Sold $268K · Dec 2019
- 68 Winesap Rd$436K4 bd · 2.5 ba · 2,224 ft² · Sold $290K · Nov 2019
- 109 Winesap Rd$467K4 bd · 2.5 ba · 2,176 ft² · Sold $342K · Sep 2019
Closest homes
- 24 Winesap Rd$424K82 ft · 4 bd · 4 ba · 1,973 ft² · Sold $244K · Feb 2007
- 12 Winesap Rd$389K83 ft · 3 bd · 2 ba · 1,494 ft² · Sold $360K · Nov 2023
- 30 Winesap Rd$361K164 ft · 3 bd · 1.5 ba · 1,473 ft² · Sold $128K · Oct 1999
- 6 Winesap Rd$431K166 ft · 3 bd · 2 ba · 1,934 ft² · Sold Mar 2024
- 36 Winesap Rd$371K245 ft · 3 bd · 2.5 ba · 1,720 ft² · Sold $279K · Oct 2021
- 1826 East St$349K296 ft · 3 bd · 1 ba · 1,562 ft² · Sold $161K · Sep 2006
- 25 Winesap Rd$375K233 ft · 3 bd · 2.5 ba · 1,610 ft² · Sold $177K · Dec 2012
- 27 Winesap Rd$368K251 ft · 4 bd · 2 ba · 1,468 ft² · Sold $311K · Nov 2022
More homes in Pittsfield 01201
- 106 E Housatonic St$200K2 bd · 1 ba · 803 ft² · Sold $190K · Sep 2026
- 65 Cecelia Ter$217K2 bd · 1 ba · 816 ft² · Sold $147K · Sep 2026
- 28 Adelaide Ave$329K4 bd · 3 ba · 1,575 ft² · Sold $340K · Sep 2026
- 62 Pomeroy Ave$349K4 bd · 2 ba · 2,158 ft² · Sold $340K · Sep 2026
- 17 Chatham St$280K3 bd · 1 ba · 1,056 ft² · Sold $250K · Sep 2026
- 82 Parkside Ave6 bd · 2 ba · 2,432 ft² · Sold $301K · Sep 2026
- 24 Rockland Dr$475K3 bd · 2.5 ba · 1,702 ft² · Sold $455K · Sep 2026
- 160 Chestnut Rd$325K3 bd · 1 ba · 768 ft² · Sold $315K · Aug 2026
- 31 Osceola St$297K3 bd · 1.5 ba · 1,196 ft² · Sold $280K · Aug 2026
- 61 Harding St$295K3 bd · 1 ba · 1,282 ft² · Sold $300K · Aug 2026
- 38 Crofut St$902K5 bd · 3.5 ba · 3,877 ft² · Sold $1.2M · Aug 2026
- 21 Newell St6 bd · 2 ba · 2,352 ft² · Sold $213K · Aug 2026
Assigned schools
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