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Single Family ResidenceResidential
$935,076$455 / 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 73How well the pricing models agreed with each other on this home. Higher means the estimate rests on stronger, more consistent data.· as of Oct 21, 2026

28555 JOLLY ROGER DR

SUMMERLAND KEY, FL 33042
3
Beds
3
Baths
2,057 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.
0.18 ac
Lot SizeThe size of the land the home sits on, from county records.
1968
Year BuiltThe year the home was originally built, according to county records.
2
StoriesHow many floors the home has above ground.

Valuation

$935K
$682K low$1.2M high

Tax & Assessment

Property TaxThe property tax billed for this tax year. It usually pays for schools, roads, and local services.$3,509 (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.$345,280 (2025)
Previous AssessedThe county's assessed value from the year before, useful for seeing how the assessment changed.$335,550
Assessor Market ValueThe county assessor's own opinion of market value. It is separate from our estimate and updates on the county's schedule.$901,427

Climate Risk

Projected Flood DepthHow deep a serious flood is expected to get here at some point in the next 30 years. Shown in inches.55 in
30-Year Flood ChanceThe chance of at least one serious flood here in the next 30 years, not in any single year.100%
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.1 percent flood zone

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
CountyMONROE
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.2004
Lot (acres)The size of the land the home sits on, from county records.0.18
ConstructionThe main material the home's frame and walls are built from.Wood (Unspecified)
FoundationWhat the home is built on, such as a concrete slab, a crawl space, or a basement.Mat/Raft Foundation (Slab)
RoofThe main material covering the roof, such as asphalt shingle or tile.Metal
HeatingThe type of heating system in the home.None
CoolingThe type of cooling or air conditioning in the home.None
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.Patio · 99 ft²Porch · 834 ft²Boat access

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.

E
Sugarloaf SchoolB-
Elementary · Grades PK–8 · 9.1 mi
H
Key West High SchoolC
High · Grades 9–12 · 25.6 mi

District: Monroe County School District

Neighborhood · ZIP 33042These 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.88
Air pollutionOverall air pollution compared with the rest of the country, where 100 is average. Lower is cleaner.81
EarthquakeEarthquake risk and likely building damage compared with the rest of the country, where 100 is average. Scores can run far above 100.2

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.69%
Bachelor's or higherThe share of adults 25 and older whose highest degree is a bachelor's degree.25%
Poverty rateThe share of people whose household income falls below the federal poverty line, which varies by family size.10%
UnemploymentThe share of men 16 and older who are out of work and actively looking. Only men are counted in this figure.0.6%
PopulationHow many people live in this area.5,645
DensityPeople per square mile. Higher numbers mean a more crowded, urban area.45 / mi²
Median incomeThe middle household income here — half of households earn more, half earn less.$102,582
Average incomeThe average household income. It runs higher than the median when a few high earners pull it up.$147,417
Average tempThe average temperature here across a full year.78°F
Annual precipHow much rain and melted snow falls here in a typical year.43 in
SunshineThe share of daylight hours that get direct sun in a typical year, counting cloud cover.76%

Owner Tools

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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

28555 Jolly Roger 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.

  • Costs less per square foot than 95% of homes in Summerland Key 33042
  • Bigger than 82% of homes in Summerland Key 33042
  • Older than 92% of homes in Summerland Key 33042

What homes are worth in Summerland Key 33042

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

This home
$548K$3.5M

This home is worth more than 41% of homes in Summerland Key 33042.

How it measures up in Summerland Key 33042

The dot is this home. The mark in the middle is the typical home in Summerland Key 33042.

Estimated value$935,076
CheaperTypical $1,026,782Pricier

Pricier than 41% of homes nearby

Price per ft²$455
CheaperTypical $728Pricier

Pricier than 5% of homes nearby

Living area2,057 ft²
SmallerTypical 1,350 ft²Bigger

Bigger than 82% of homes nearby

Lot size0.18 ac
SmallerTypical 0.17 acBigger

Bigger than 54% of homes nearby

Year built1968
OlderTypical 1989Newer

Newer than 8% of homes nearby

How 28555 Jolly Roger Dr ranks against every home in each area.
MeasureThis homeSummerland Key 33042Monroe County
Estimated valuepricier than$935,07641% of homes46% of homes
Price per ft²pricier than$4555% of homes10% of homes
Living areabigger than2,057 ft²82% of homes80% of homes
Lot sizebigger than0.18 ac54% of homes57% of homes
Year builtnewer than19688% of homes22% of homes

About 28555 Jolly Roger Dr

How much is 28555 Jolly Roger Dr, Summerland Key, FL worth?

The TopHap Estimate for 28555 Jolly Roger Dr, Summerland Key, FL is $935,076 as of Oct 21, 2026. The likely range is $682,477 to $1,187,675. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.

When did 28555 Jolly Roger Dr, Summerland Key, FL last sell?

28555 Jolly Roger Dr, Summerland Key, FL last sold on May 10, 2007, according to the county's recorded deed.

How big is 28555 Jolly Roger Dr, Summerland Key, FL?

28555 Jolly Roger Dr, Summerland Key, FL has 3 bedrooms, 3 bathrooms, 2,057 square feet of living space and a 0.18-acre lot.

When was 28555 Jolly Roger Dr, Summerland Key, FL built?

28555 Jolly Roger Dr, Summerland Key, FL was built in 1968, making it 58 years old. The building has 2 stories.

What schools serve 28555 Jolly Roger Dr, Summerland Key, FL?

28555 Jolly Roger Dr, Summerland Key, FL is assigned to Sugarloaf School (elementary), rated B-; Key West High School (high), rated C. All sit in Monroe County School District. Attendance boundaries change — confirm with the district before relying on an assignment.

How does 28555 Jolly Roger Dr, Summerland Key, FL compare to other homes in Summerland Key 33042?

Among the 4,624 homes in Summerland Key 33042, it is worth more than 41% of them ($935,076 against a typical $1,026,782), its price per square foot is higher than 5% of them ($455 against a typical $728), it is bigger than 82% of them (2,057 ft² against a typical 1,350 ft²), its lot is bigger than 54% of them (0.18 ac against a typical 0.17 ac) and it is newer than 8% of them (1968 against a typical 1989). Measured against all of Monroe County, it is worth more than 46% 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 28555 Jolly Roger Dr, Summerland Key, FL?

The 2025 property tax bill for 28555 Jolly Roger Dr, Summerland Key, FL was $3,509. The county assessed it at $345,280.

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