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Single Family ResidenceResidential
$1,045,850$294 / 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 87How 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 $900,000 on Dec 11, 2023

39 PENNYWHISTLE DR

WINDHAM, ME 04062
3
Beds
2.5
Baths
3,556 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.
0.9 ac
Lot SizeThe size of the land the home sits on, from county records.
2021
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.

Valuation

$1M
$913K low$1.2M high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$900,000 · Dec 11, 2023

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$10,803 (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.$895,800 (2025)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$154,600
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$741,200
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$858,200

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
CountyCUMBERLAND
Lot (acres)The size of the land the home sits on, from county records.0.90
RoofThe main material covering the roof, such as asphalt shingle or tile.Asphalt
HeatingThe type of heating system in the home.Heat Pump
FireplaceWhether the home has a fireplace, and what kind.Yes
PoolWhether the property has a pool, and what kind, such as in-ground.No

Transaction History(1)

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.

H
Windham High SchoolB-
High · Grades 9–12 · 2.7 mi
E
Windham Primary SchoolC+
Elementary · Grades KG–3 · 2.8 mi
M
Windham Middle SchoolC
Middle · Grades 6–8 · 2.8 mi

District: Regional School Unit 14

Neighborhood · ZIP 04062These 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.80
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.88
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.89

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.91%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.31%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.3.8%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.0.8%
PopulationHow many people live in this area.19,269
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.383 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$102,304
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$123,314
Average tempThe average temperature here across a full year.45°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.57%

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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

39 Pennywhistle 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 more than 97% of homes in Windham 04062
  • Costs less per square foot than 84% of homes in Cumberland County
  • Bigger than 98% of homes in Windham 04062
  • Newer than 97% of homes in Windham 04062

What homes are worth in Windham 04062

Each bar is how many homes fall in that price range. The marker is this home.

This home
$292K$1.2M

This home is worth more than 97% of homes in Windham 04062.

How it measures up in Windham 04062

The dot is this home. The mark in the middle is the typical home in Windham 04062.

Estimated value$1,045,850
CheaperTypical $493,100Pricier

Pricier than 97% of homes nearby

Price per ft²$294
CheaperTypical $341Pricier

Pricier than 28% of homes nearby

Living area3,556 ft²
SmallerTypical 1,440 ft²Bigger

Bigger than 98% of homes nearby

Lot size0.9 ac
SmallerTypical 0.97 acBigger

Bigger than 47% of homes nearby

Year built2021
OlderTypical 1988Newer

Newer than 97% of homes nearby

How 39 Pennywhistle Dr ranks against every home in each area.
MeasureThis homeWindham 04062Cumberland County
Estimated valuepricier than$1,045,85097% of homes87% of homes
Price per ft²pricier than$29428% of homes16% of homes
Living areabigger than3,556 ft²98% of homes96% of homes
Lot sizebigger than0.9 ac47% of homes58% of homes
Year builtnewer than202197% of homes97% of homes

About 39 Pennywhistle Dr

How much is 39 Pennywhistle Dr, Windham, ME worth?

The TopHap Estimate for 39 Pennywhistle Dr, Windham, ME is $1,045,850 as of Sep 24, 2026. The likely range is $912,952 to $1,178,748. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 39 Pennywhistle Dr, Windham, ME last sell?

39 Pennywhistle Dr, Windham, ME last sold on Dec 11, 2023 for $900,000, according to the county's recorded deed.

How big is 39 Pennywhistle Dr, Windham, ME?

39 Pennywhistle Dr, Windham, ME has 3 bedrooms, 2.5 bathrooms, 3,556 square feet of living space and a 0.90-acre lot.

When was 39 Pennywhistle Dr, Windham, ME built?

39 Pennywhistle Dr, Windham, ME was built in 2021, making it 5 years old. It is a colonial home. The building has 2 stories.

What schools serve 39 Pennywhistle Dr, Windham, ME?

39 Pennywhistle Dr, Windham, ME is assigned to Windham High School (high), rated B-; Windham Primary School (elementary), rated C+; Windham Middle School (middle), rated C. All sit in Regional School Unit 14. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 39 Pennywhistle Dr, Windham, ME compare to other homes in Windham 04062?

Among the 7,616 homes in Windham 04062, it is worth more than 97% of them ($1,045,850 against a typical $493,100), its price per square foot is higher than 28% of them ($294 against a typical $341), it is bigger than 98% of them (3,556 ft² against a typical 1,440 ft²), its lot is bigger than 47% of them (0.9 ac against a typical 0.97 ac) and it is newer than 97% of them (2021 against a typical 1988). Measured against all of Cumberland County, it is worth more than 87% 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 39 Pennywhistle Dr, Windham, ME?

The 2025 property tax bill for 39 Pennywhistle Dr, Windham, ME was $10,803. The county assessed it at $895,800.

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