22757 JOLLY ROGER DR
Valuation
Tax & Assessment
Climate Risk
Scores 0–100; higher = greater projected risk.
Property Facts
Transaction History(3)
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.
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.
Index scale: 100 = US average (tick). Lower is better.
Owner Tools
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
22757 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.
- Worth less than 82% of homes in Summerland Key 33042
- Costs more per square foot than 93% of homes in Summerland Key 33042
- Smaller than 98% of homes in Summerland Key 33042
- Older than 94% 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 is worth more than 18% 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.
Pricier than 18% of homes nearby
Pricier than 93% of homes nearby
Bigger than 2% of homes nearby
Bigger than 60% of homes nearby
Newer than 6% of homes nearby
| Measure | This home | Summerland Key 33042 | Monroe County |
|---|---|---|---|
| Estimated valuepricier than | $752,568 | 18% of homes | 30% of homes |
| Price per ft²pricier than | $1254 | 93% of homes | 86% of homes |
| Living areabigger than | 600 ft² | 2% of homes | 4% of homes |
| Lot sizebigger than | 0.2 ac | 60% of homes | 61% of homes |
| Year builtnewer than | 1963 | 6% of homes | 18% of homes |
About 22757 Jolly Roger Dr
How much is 22757 Jolly Roger Dr, Cudjoe Key, FL worth?
The TopHap Estimate for 22757 Jolly Roger Dr, Cudjoe Key, FL is $752,568 as of Aug 30, 2026. The likely range is $698,166 to $806,970. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 22757 Jolly Roger Dr, Cudjoe Key, FL last sell?
22757 Jolly Roger Dr, Cudjoe Key, FL last sold on Jul 13, 2021 for $598,000, according to the county's recorded deed. TopHap holds 3 recorded sales for this parcel.
How big is 22757 Jolly Roger Dr, Cudjoe Key, FL?
22757 Jolly Roger Dr, Cudjoe Key, FL has 2 bedrooms, 1 bathrooms, 600 square feet of living space and a 0.20-acre lot.
When was 22757 Jolly Roger Dr, Cudjoe Key, FL built?
22757 Jolly Roger Dr, Cudjoe Key, FL was built in 1963, making it 63 years old. The building has 2 stories.
What schools serve 22757 Jolly Roger Dr, Cudjoe Key, FL?
22757 Jolly Roger Dr, Cudjoe 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 22757 Jolly Roger Dr, Cudjoe Key, FL compare to other homes in Summerland Key 33042?
Among the 4,625 homes in Summerland Key 33042, it is worth more than 18% of them ($752,568 against a typical $1,027,601), its price per square foot is higher than 93% of them ($1254 against a typical $748), it is bigger than 2% of them (600 ft² against a typical 1,320 ft²), its lot is bigger than 60% of them (0.2 ac against a typical 0.17 ac) and it is newer than 6% of them (1963 against a typical 1989). Measured against all of Monroe County, it is worth more than 30% 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 22757 Jolly Roger Dr, Cudjoe Key, FL?
The 2024 property tax bill for 22757 Jolly Roger Dr, Cudjoe Key, FL was $6,475. The county assessed it at $745,932.
More homes on Jolly Roger Dr
- 22521 Jolly Roger Dr$1.1M4 bd · 2.5 ba · 1,728 ft² · Sold $1M · Nov 2025
- 22440 Jolly Roger Dr$2.1M2 bd · 2 ba · 1,292 ft² · Sold $2M · May 2025
- 22903 Jolly Roger Dr$720K3 bd · 2 ba · 1,152 ft² · Sold $685K · Dec 2024
- 22532 Jolly Roger Dr$1.7M3 bd · 2 ba · 1,288 ft² · Sold $1.6M · Nov 2024
- 22892 Jolly Roger Dr$1.9M3 bd · 2 ba · 1,767 ft² · Sold $1.7M · May 2022
- 22888 Jolly Roger Dr$1.1M2 bd · 3 ba · 1,250 ft² · Sold $1.3M · Jul 2021
- 22480 Jolly Roger Dr$2M3 bd · 2 ba · 1,494 ft² · Sold $1.1M · Nov 2020
- 22358 Jolly Roger Dr$1.7M4 bd · 3 ba · 2,668 ft² · Sold $990K · Aug 2020
- 22388 Jolly Roger Dr$1.4M3 bd · 2 ba · 1,872 ft² · Sold $1.1M · Aug 2020
- 22864 Jolly Roger Dr$1.5M2 bd · 2 ba · 1,120 ft² · Sold $870K · Mar 2018
- 22470 Jolly Roger Dr$2M2 bd · 3 ba · 1,368 ft² · Sold $1.1M · Mar 2017
- 22460 Jolly Roger Dr0.11 ac · Sold Mar 2017
Closest homes
- 175 Cutlass Ln$646K76 ft · 2 bd · 2 ba · 930 ft² · Sold $479K · Jan 2020
- 165 Cutlass Ln$1M136 ft · 4 bd · 3 ba · 2,448 ft² · Sold $1M · Aug 2026
- 22777 Jolly Roger Dr$1.2M132 ft · 3 bd · 2 ba · 1,713 ft² · Sold $630K · Oct 2019
- 22766 Jolly Roger Dr$1.9M151 ft · 3 bd · 2 ba · 1,884 ft² · Sold $1.8M · Nov 2024
- 194 Cutthroat Dr$946K163 ft · 3 bd · 2 ba · 1,338 ft² · Sold $35K · Nov 1991
- 22776 Jolly Roger Dr$1.4M174 ft · 3 bd · 2 ba · 1,056 ft² · Sold $550K · Jul 2003
- 22746 Jolly Roger Dr$1.3M172 ft · 3 bd · 2 ba · 1,278 ft² · Sold $50K · Nov 1987
- 22727 Jolly Roger Dr$836K174 ft · 2 bd · 2 ba · 1,008 ft² · Sold $800K · Feb 2025
More homes in Cudjoe Key 33042
- Bk14 Lt 1 Vacant Land0.16 ac · Sold $30K · Aug 2026
- 287 Airport Dr N$686K4 bd · 2 ba · 1,260 ft² · Sold $638K · Aug 2026
- 4039 Egret Ln$685K2 bd · 1 ba · 768 ft² · Sold $685K · Aug 2026
- 27372 W Indies Dr$1.3M3 bd · 2 ba · 1,800 ft² · Sold $1.3M · Aug 2026
- 27426 Martinique Ln$975K3 bd · 2 ba · 1,408 ft² · Sold $975K · Aug 2026
- 612 Blackbeard Rd$1.2M3 bd · 2 ba · 2,394 ft² · Sold $1.2M · Aug 2026
- 596 W Shore Dr3 bd · 3 ba · 2,832 ft² · Sold $975K · Aug 2026
- Vacant Lan Martinique Ln0.14 ac · Sold $975K · Aug 2026
- 27356 Dominica Ln$2.1M3 bd · 2 ba · 1,800 ft² · Sold $2.1M · Aug 2026
- Rocky Rd9.99 ac · Sold $330K · Aug 2026
- 22370 La Fitte Dr$889K2 bd · 2 ba · 864 ft² · Sold $176K · Aug 2026
- 17385 Keystone Rd$2.5M2 bd · 1 ba · 2,256 ft² · Sold $2.5M · Aug 2026
Assigned schools
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