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Single Family ResidenceResidential
$745,405$415 / 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 94How 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 $655,000 on Jan 22, 2024

299 HILLSMERE DR

ANNAPOLIS, MD 21403
2
Baths
1,798 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.
0.39 ac
Lot SizeThe size of the land the home sits on, from county records.
1973
Year BuiltThe year the home was originally built, according to county records.
2
StoriesHow many floors the home has above ground.
2
ParkingThe number of parking spaces on the property, including the garage.

Valuation

$745K
$700K low$791K high
Last SaleThe most recent sale price and date from the recorded deed. Transfers between family members or companies may not reflect market value.$655,000 · Jan 22, 2024

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$5,840 (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.$501,100 (2026)
Assessed LandThe share of the county's assessed value that comes from the land itself, not the buildings.$258,400
Assessed ImprovementsThe share of the county's assessed value that comes from the buildings and other structures on the land.$242,700
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$476,200
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$501,100

Climate Risk

Overall riskThe average of the five hazard scores below, on a 0 to 100 scale. Higher means greater projected risk over the coming decades.6
1
FloodProjected flooding risk from rivers, heavy rain, and storm surge, scored 0 to 100. Higher is riskier.
20
WildfireProjected wildfire risk, scored 0 to 100, based on how much land burns in a typical year. Higher is riskier.
9
DroughtProjected water shortage risk, scored 0 to 100. Higher means more strain on the local water supply.
FEMA Flood ZoneFEMA's flood zone for this address. Zones starting with A or V are high risk, and lenders usually require flood insurance there.minimal

Scores 0–100; higher = greater projected risk.

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
CountyANNE ARUNDEL
Lot (acres)The size of the land the home sits on, from county records.0.39
RoofThe main material covering the roof, such as asphalt shingle or tile.Composition Shingle
HeatingThe type of heating system in the home.Yes
CoolingThe type of cooling or air conditioning in the home.Central
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.No
FeaturesExtra features found in county records. Records are not complete everywhere, so a missing feature does not always mean the home lacks it.Porch · 48 ft²

Transaction History(2)

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
Hillsmere Elementary SchoolA
Elementary · Grades EE–5 · 0.4 mi
M
Annapolis Middle SchoolC
Middle · Grades 6–8 · 1.4 mi
H
Annapolis High SchoolC
High · Grades 9–12 · 4.5 mi

District: Anne Arundel County Public Schools

Neighborhood · ZIP 21403These 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.130
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.85
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.34

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.92%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.32%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.8.5%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.0.9%
PopulationHow many people live in this area.32,838
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.2,339 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$117,902
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$161,719
Average tempThe average temperature here across a full year.57°F
Annual precipHow much rain and melted snow falls here in a typical year.45 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

299 Hillsmere 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 79% of homes in Anne Arundel County
  • Costs more per square foot than 91% of homes in Anne Arundel County
  • Has a bigger lot than 81% of homes in Annapolis 21403
  • Older than 66% of homes in Hillsmere Shores

What homes are worth in Annapolis 21403

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

This home
$263K$2.8M

This home is worth more than 60% of homes in Annapolis 21403.

How it measures up in Annapolis 21403

The dot is this home. The mark in the middle is the typical home in Annapolis 21403.

Estimated value$745,405
CheaperTypical $652,159Pricier

Pricier than 60% of homes nearby

Price per ft²$415
CheaperTypical $363Pricier

Pricier than 64% of homes nearby

Living area1,798 ft²
SmallerTypical 1,712 ft²Bigger

Bigger than 54% of homes nearby

Lot size0.39 ac
SmallerTypical 0.2 acBigger

Bigger than 81% of homes nearby

Year built1973
OlderTypical 1980Newer

Newer than 38% of homes nearby

How 299 Hillsmere Dr ranks against every home in each area.
MeasureThis homeHillsmere ShoresAnnapolis 21403Anne Arundel County
Estimated valuepricier than$745,40564% of homes60% of homes79% of homes
Price per ft²pricier than$41585% of homes64% of homes91% of homes
Living areabigger than1,798 ft²43% of homes54% of homes47% of homes
Lot sizebigger than0.39 ac79% of homes81% of homes76% of homes
Year builtnewer than197334% of homes38% of homes37% of homes

About 299 Hillsmere Dr

How much is 299 Hillsmere Dr, Annapolis, MD worth?

The TopHap Estimate for 299 Hillsmere Dr, Annapolis, MD is $745,405 as of Sep 24, 2026. The likely range is $700,074 to $790,736. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 299 Hillsmere Dr, Annapolis, MD last sell?

299 Hillsmere Dr, Annapolis, MD last sold on Jan 22, 2024 for $655,000, according to the county's recorded deed. TopHap holds 2 recorded sales for this parcel.

How big is 299 Hillsmere Dr, Annapolis, MD?

299 Hillsmere Dr, Annapolis, MD has 2 bathrooms, 1,798 square feet of living space and a 0.39-acre lot.

When was 299 Hillsmere Dr, Annapolis, MD built?

299 Hillsmere Dr, Annapolis, MD was built in 1973, making it 53 years old. It is a conventional home. The building has 2 stories.

What schools serve 299 Hillsmere Dr, Annapolis, MD?

299 Hillsmere Dr, Annapolis, MD is assigned to Hillsmere Elementary School (elementary), rated A; Annapolis Middle School (middle), rated C; Annapolis High School (high), rated C. All sit in Anne Arundel County Public Schools. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 299 Hillsmere Dr, Annapolis, MD compare to other homes in Annapolis 21403?

Among the 11,835 homes in Annapolis 21403, it is worth more than 60% of them ($745,405 against a typical $652,159), its price per square foot is higher than 64% of them ($415 against a typical $363), it is bigger than 54% of them (1,798 ft² against a typical 1,712 ft²), its lot is bigger than 81% of them (0.39 ac against a typical 0.2 ac) and it is newer than 38% of them (1973 against a typical 1980). Measured against all of Anne Arundel County, it is worth more than 79% 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 299 Hillsmere Dr, Annapolis, MD?

The 2025 property tax bill for 299 Hillsmere Dr, Annapolis, MD was $5,840. The county assessed it at $501,100.

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