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Single Family ResidenceResidential
$485,332$243 / ft²
TopHap EstimateOur estimate of what this home would sell for today, based on nearby sales, the home's size and features, and local price trends. It is a starting point, not an appraisal.· confidence 95How well the pricing models agreed with each other on this home. Higher means the estimate rests on stronger, more consistent data.· as of Sep 24, 2026
Last sold for $257,900 on Jan 28, 2013

105 WINESAP RD

PITTSFIELD, MA 01201
4
Beds
2.5
Baths
1,998 ft²
Living AreaTotal finished area of the structures, from county records. Some counties include shared space like hallways or a building gym, so it may not match a listing.
0.3 ac
Lot SizeThe size of the land the home sits on, from county records.
1985
Year BuiltThe year the home was originally built, according to county records.
2
StoriesHow many floors the home has above ground.
8
RoomsThe total room count in county records. Counties differ on which rooms they count, so compare it loosely.
1
ParkingThe number of parking spaces on the property, including the garage.

Valuation

$485K
$460K low$511K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$257,900 · Jan 28, 2013

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$8,769 (2025)
Assessed ValueThe value the county assigns to this home to calculate property tax. It is often lower than what the home would sell for.$488,800 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$91,100
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$397,700

Property Facts

Property TypeThe broad category the county puts this property in, such as residential or commercial.Single Family Residence
StyleThe architectural style of the home, such as ranch or colonial.Colonial
CountyBERKSHIRE
Lot (acres)The size of the land the home sits on, from county records.0.30
HeatingThe type of heating system in the home.Hot Water
CoolingThe type of cooling or air conditioning in the home.Yes
FireplaceWhether the home has a fireplace, and what kind.Yes
GarageWhether the property has a garage, and details like whether it is attached to the home.Garage, Attached
PoolWhether the property has a pool, and what kind, such as in-ground.In-Ground Pool
FeaturesExtra features found in county records. Records are not complete everywhere, so a missing feature does not always mean the home lacks it.Deck

Transaction History(8)

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.

E
WilliamsB
Elementary · Grades PK–5 · 0.9 mi
M
Theodore Herberg Middle SchoolD-
Middle · Grades 6–8 · 2.3 mi
H
Pittsfield High SchoolC
High · Grades 9–12 · 2.4 mi

District: Pittsfield School District

Neighborhood · ZIP 01201These are comparison scores, not percentages. 100 equals the national average, so 150 means about 50% above average.

CrimeLocal crime compared with the rest of the country, where 100 is average. It reflects things like population density, income, and how crime gets reported.90
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.87
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.52

Index scale: 100 = US average (tick). Lower is better.

Homes occupiedThe share of homes here that someone lives in. The rest sit empty, including vacation and for-sale homes.90%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.22%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.15%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.1.2%
PopulationHow many people live in this area.45,556
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.639 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$69,277
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$91,002
Average tempThe average temperature here across a full year.44°F
Annual precipHow much rain and melted snow falls here in a typical year.47 in
SunshineThe share of daylight hours that get direct sun in a typical year, counting cloud cover.50%

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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

105 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 85% of homes in Pittsfield 01201
  • Costs more per square foot than 67% of homes in Pittsfield 01201
  • Bigger than 69% of homes in Pittsfield 01201
  • Has a bigger lot than 65% of homes in Pittsfield 01201
  • Newer than 89% 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
$144K$907K

This home is worth more than 85% 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.

Estimated value$485,332
CheaperTypical $311,414Pricier

Pricier than 85% of homes nearby

Price per ft²$243
CheaperTypical $222Pricier

Pricier than 67% of homes nearby

Living area1,998 ft²
SmallerTypical 1,566 ft²Bigger

Bigger than 69% of homes nearby

Lot size0.3 ac
SmallerTypical 0.24 acBigger

Bigger than 65% of homes nearby

Year built1985
OlderTypical 1945Newer

Newer than 89% of homes nearby

How 105 Winesap Rd ranks against every home in each area.
MeasureThis homePittsfield 01201Berkshire County
Estimated valuepricier than$485,33285% of homes65% of homes
Price per ft²pricier than$24367% of homes47% of homes
Living areabigger than1,998 ft²69% of homes66% of homes
Lot sizebigger than0.3 ac65% of homes36% of homes
Year builtnewer than198589% of homes78% of homes

About 105 Winesap Rd

How much is 105 Winesap Rd, Pittsfield, MA worth?

The TopHap Estimate for 105 Winesap Rd, Pittsfield, MA is $485,332 as of Sep 24, 2026. The likely range is $460,086 to $510,578. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 105 Winesap Rd, Pittsfield, MA last sell?

105 Winesap Rd, Pittsfield, MA last sold on Jan 28, 2013 for $257,900, according to the county's recorded deed. TopHap holds 6 recorded sales for this parcel.

How big is 105 Winesap Rd, Pittsfield, MA?

105 Winesap Rd, Pittsfield, MA has 4 bedrooms, 2.5 bathrooms, 1,998 square feet of living space and a 0.30-acre lot.

When was 105 Winesap Rd, Pittsfield, MA built?

105 Winesap Rd, Pittsfield, MA was built in 1985, making it 41 years old. It is a colonial home. The building has 2 stories.

What schools serve 105 Winesap Rd, Pittsfield, MA?

105 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 105 Winesap Rd, Pittsfield, MA compare to other homes in Pittsfield 01201?

Among the 14,716 homes in Pittsfield 01201, it is worth more than 85% of them ($485,332 against a typical $311,414), its price per square foot is higher than 67% of them ($243 against a typical $222), it is bigger than 69% of them (1,998 ft² against a typical 1,566 ft²), its lot is bigger than 65% of them (0.3 ac against a typical 0.24 ac) and it is newer than 89% of them (1985 against a typical 1945). Measured against all of Berkshire County, it is worth more than 65% 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 105 Winesap Rd, Pittsfield, MA?

The 2025 property tax bill for 105 Winesap Rd, Pittsfield, MA was $8,769. The county assessed it at $488,800.

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