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Single Family ResidenceResidential
$464,142$478 / 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 92How well the pricing models agreed with each other on this home. Higher means the estimate rests on stronger, more consistent data.· as of Jul 14, 2026
Last sold for $228,500 on Feb 13, 2012

99 WINTER ST

HOLLISTON, MA 01746
2
Beds
1
Baths
971 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.
1.4 ac
Lot SizeThe size of the land the home sits on, from county records.
1940
Year BuiltThe year the home was originally built, according to county records.
2
StoriesHow many floors the home has above ground.
5
RoomsThe total room count in county records. Counties differ on which rooms they count, so compare it loosely.

Valuation

$464K
$428K low$500K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$228,500 · Feb 13, 2012
Est. Owner EquityRoughly how much of the home's value the owner would keep after paying off known loans. It is our estimate minus the loans still owed.$54,142
Est. Lendable EquityThe part of the owner's equity a lender would typically let them borrow against — about 80% of their equity.$43,314
Loan-to-ValueHow much is still owed on the home compared to what it is worth. 80% means loans equal 80% of our estimate, so it shifts when the estimate does.85%
1st MortgageA loan still believed to be open on this home, in the order lenders get repaid. The first position is paid back before the second.$410,000
UNIBANK FOR SAVINGS · recorded Oct 15, 2025

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$6,036 (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.$412,000 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$294,400
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$117,600
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$450,870

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.Conventional
CountyMIDDLESEX
Effective Year BuiltAn adjusted build year that accounts for condition and major remodels. A big renovation can make a home count as newer than it is.1970
Lot (acres)The size of the land the home sits on, from county records.1.40
ConstructionThe main material the home's frame and walls are built from.Stone
RoofThe main material covering the roof, such as asphalt shingle or tile.Asphalt
HeatingThe type of heating system in the home.Forced Air With Air Conditioning
CoolingThe type of cooling or air conditioning in the home.Yes
GarageWhether the property has a garage, and details like whether it is attached to the home.Garage, Detached
PoolWhether the property has a pool, and what kind, such as in-ground.No

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.

Assigned SchoolsThe public schools this address is zoned for. Boundaries change, so confirm with the district before you count on it.

E
Placentino Elementary School
Elementary · Grades PK–2 · 0.5 mi
M
Robert H. Adams Middle SchoolA-
Middle · Grades 6–8 · 0.6 mi
H
Holliston High SchoolA
High · Grades 9–12 · 0.8 mi

District: Holliston School District

Neighborhood · ZIP 01746These 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.11
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.93
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.67

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.97%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.39%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.3.1%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.1.4%
PopulationHow many people live in this area.15,460
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.813 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$148,945
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$184,552
Average tempThe average temperature here across a full year.49°F
Annual precipHow much rain and melted snow falls here in a typical year.48 in
SunshineThe share of daylight hours that get direct sun in a typical year, counting cloud cover.58%

Ownership

OccupancyWhether the owner appears to live here or somewhere else. It is inferred from the mailing address on record.Owner occupied
Company ownedWhether the owner is a company or trust rather than a person.No

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

99 Winter St 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 93% of homes in Holliston 01746
  • Costs more per square foot than 78% of homes in Holliston 01746
  • Smaller than 92% of homes in Holliston 01746
  • Has a bigger lot than 86% of homes in Middlesex County
  • Older than 90% of homes in Holliston 01746

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
$232K$1.5M

This home is worth more than 7% 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.

Estimated value$464,142
CheaperTypical $726,992Pricier

Pricier than 7% of homes nearby

Price per ft²$478
CheaperTypical $390Pricier

Pricier than 78% of homes nearby

Living area971 ft²
SmallerTypical 1,897 ft²Bigger

Bigger than 8% of homes nearby

Lot size1.4 ac
SmallerTypical 0.7 acBigger

Bigger than 75% of homes nearby

Year built1940
OlderTypical 1968Newer

Newer than 10% of homes nearby

How 99 Winter St ranks against every home in each area.
MeasureThis homeHolliston 01746Middlesex County
Estimated valuepricier than$464,1427% of homes11% of homes
Price per ft²pricier than$47878% of homes54% of homes
Living areabigger than971 ft²8% of homes10% of homes
Lot sizebigger than1.4 ac75% of homes86% of homes
Year builtnewer than194010% of homes36% of homes

About 99 Winter St

How much is 99 Winter St, Holliston, MA worth?

The TopHap Estimate for 99 Winter St, Holliston, MA is $464,142 as of Jul 14, 2026. The likely range is $428,471 to $499,813. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 99 Winter St, Holliston, MA last sell?

99 Winter St, Holliston, MA last sold on Feb 13, 2012 for $228,500, according to the county's recorded deed. TopHap holds 4 recorded sales for this parcel.

How big is 99 Winter St, Holliston, MA?

99 Winter St, Holliston, MA has 2 bedrooms, 1 bathrooms, 971 square feet of living space and a 1.40-acre lot.

When was 99 Winter St, Holliston, MA built?

99 Winter St, Holliston, MA was built in 1940, making it 86 years old. It is a conventional home. The building has 2 stories.

What schools serve 99 Winter St, Holliston, MA?

99 Winter St, 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 99 Winter St, Holliston, MA compare to other homes in Holliston 01746?

Among the 5,229 homes in Holliston 01746, it is worth more than 7% of them ($464,142 against a typical $726,992), its price per square foot is higher than 78% of them ($478 against a typical $390), it is bigger than 8% of them (971 ft² against a typical 1,897 ft²), its lot is bigger than 75% of them (1.4 ac against a typical 0.7 ac) and it is newer than 10% of them (1940 against a typical 1968). Measured against all of Middlesex County, it is worth more than 11% 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 99 Winter St, Holliston, MA?

The 2025 property tax bill for 99 Winter St, Holliston, MA was $6,036. The county assessed it at $412,000.

Closest homes

More homes in Holliston 01746

Assigned schools

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