5550 ROLLINGWOOD DR
Valuation
Tax & Assessment
Climate Risk
Scores 0–100; higher = greater projected risk.
Property Facts
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.
District: Sarasota County School District
Neighborhood · ZIP 34232These 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
5550 Rollingwood 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 more per square foot than 73% of homes in Sarasota 34232
- Smaller than 68% of homes in Sarasota County
- Older than 75% of homes in Sarasota County
What homes are worth in Sarasota 34232
Each bar is how many homes fall in that price range. The marker is this home.
This home is worth more than 54% of homes in Sarasota 34232.
How it measures up in Sarasota 34232
The dot is this home. The mark in the middle is the typical home in Sarasota 34232.
Pricier than 54% of homes nearby
Pricier than 73% of homes nearby
Bigger than 42% of homes nearby
Bigger than 63% of homes nearby
Newer than 33% of homes nearby
| Measure | This home | Central Sarasota | Sarasota 34232 | Sarasota County |
|---|---|---|---|---|
| Estimated valuepricier than | $340,916 | 46% of homes | 54% of homes | 40% of homes |
| Price per ft²pricier than | $261 | 65% of homes | 73% of homes | 60% of homes |
| Living areabigger than | 1,308 ft² | 36% of homes | 42% of homes | 32% of homes |
| Lot sizebigger than | 0.23 ac | 57% of homes | 63% of homes | 58% of homes |
| Year builtnewer than | 1974 | 40% of homes | 33% of homes | 25% of homes |
About 5550 Rollingwood Dr
How much is 5550 Rollingwood Dr, Sarasota, FL worth?
The TopHap Estimate for 5550 Rollingwood Dr, Sarasota, FL is $340,916 as of Sep 24, 2026. The likely range is $307,162 to $374,670. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 5550 Rollingwood Dr, Sarasota, FL last sell?
5550 Rollingwood Dr, Sarasota, FL last sold on Jan 26, 2017, according to the county's recorded deed. TopHap holds 3 recorded sales for this parcel.
How big is 5550 Rollingwood Dr, Sarasota, FL?
5550 Rollingwood Dr, Sarasota, FL has 3 bedrooms, 2 bathrooms, 1,308 square feet of living space and a 0.23-acre lot.
When was 5550 Rollingwood Dr, Sarasota, FL built?
5550 Rollingwood Dr, Sarasota, FL was built in 1974, making it 52 years old. The building has 1 story.
What schools serve 5550 Rollingwood Dr, Sarasota, FL?
5550 Rollingwood Dr, Sarasota, FL is assigned to Brentwood Elementary School (elementary), rated B; McIntosh Middle School (middle), rated B-; Sarasota High School (high), rated B-. All sit in Sarasota County School District. Attendance boundaries change — confirm with the district before relying on an assignment.
How does 5550 Rollingwood Dr, Sarasota, FL compare to other homes in Sarasota 34232?
Among the 13,866 homes in Sarasota 34232, it is worth more than 54% of them ($340,916 against a typical $327,604), its price per square foot is higher than 73% of them ($261 against a typical $234), it is bigger than 42% of them (1,308 ft² against a typical 1,416 ft²), its lot is bigger than 63% of them (0.23 ac against a typical 0.2 ac) and it is newer than 33% of them (1974 against a typical 1979). Measured against all of Sarasota County, it is worth more than 40% 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 5550 Rollingwood Dr, Sarasota, FL?
The 2025 property tax bill for 5550 Rollingwood Dr, Sarasota, FL was $1,966. The county assessed it at $208,359.
More homes on Rollingwood Dr
- 5537 Rollingwood Dr$359K4 bd · 2 ba · 1,636 ft² · Sold $370K · Sep 2025
- 5509 Rollingwood Dr$341K3 bd · 2 ba · 1,122 ft² · Sold Jun 2024
- 5526 Rollingwood Dr$399K3 bd · 2 ba · 1,440 ft² · Sold $440K · May 2024
- 5545 Rollingwood Dr$444K4 bd · 3 ba · 1,968 ft² · Sold $460K · Nov 2023
- 5544 Rollingwood Dr$373K3 bd · 2 ba · 1,634 ft² · Sold $100 · Nov 2021
- 5553 Rollingwood Dr$416K4 bd · 3 ba · 1,686 ft² · Sold Aug 2021
- 5514 Rollingwood Dr$334K3 bd · 2 ba · 1,185 ft² · Sold $260K · Dec 2020
- 5556 Rollingwood Dr$358K3 bd · 2 ba · 1,501 ft² · Sold $252K · Dec 2019
- 5541 Rollingwood Dr$336K3 bd · 2 ba · 1,370 ft² · Sold $237K · May 2017
- 5508 Rollingwood Dr$308K3 bd · 2 ba · 1,077 ft² · Sold $100 · Apr 2017
- 5525 Rollingwood Dr$350K3 bd · 2 ba · 1,426 ft² · Sold $203K · Jan 2017
- 5549 Rollingwood Dr$329K3 bd · 2 ba · 1,224 ft² · Sold $236K · Jun 2016
Closest homes
- 5544 Rollingwood Dr$373K80 ft · 3 bd · 2 ba · 1,634 ft² · Sold $100 · Nov 2021
- 5556 Rollingwood Dr$358K101 ft · 3 bd · 2 ba · 1,501 ft² · Sold $252K · Dec 2019
- 5543 Homewood Dr$331K110 ft · 3 bd · 2 ba · 1,240 ft² · Sold $75K · Jun 1996
- 5537 Homewood Dr$315K127 ft · 2 bd · 2 ba · 1,211 ft²
- 5549 Homewood Dr$317K148 ft · 2 bd · 2 ba · 1,184 ft² · Sold $165K · Dec 2015
- 5538 Rollingwood Dr$379K157 ft · 3 bd · 2 ba · 1,627 ft² · Sold $59K · Oct 1984
- 5545 Rollingwood Dr$444K160 ft · 4 bd · 3 ba · 1,968 ft² · Sold $460K · Nov 2023
- 5541 Rollingwood Dr$336K183 ft · 3 bd · 2 ba · 1,370 ft² · Sold $234K · May 2017
More homes in Sarasota 34232
- 5578 Burnt Branch Cir$465K3 bd · 2 ba · 2,137 ft² · Sold $440K · Oct 2026
- 3676 Fescue Ln$456K3 bd · 3 ba · 2,081 ft² · Sold $500K · Oct 2026
- 1307 Ingram Ave$292K3 bd · 2 ba · 1,457 ft² · Sold $315K · Oct 2026
- 3105 Baldwin Ave$395K3 bd · 2 ba · 1,466 ft² · Sold $395K · Oct 2026
- 5300 Southerly Way$430K3 bd · 2 ba · 1,662 ft² · Sold $400K · Oct 2026
- 3953 Glen Oaks Manor Dr$397K2 bd · 2 ba · 1,630 ft² · Sold $355K · Oct 2026
- 3977 Lemonwood Dr$339K2 bd · 2 ba · 1,088 ft² · Sold $325K · Oct 2026
- Bacon Ave0.27 ac · Sold $100K · Oct 2026
- 2546 Fireflag Ln$638K3 bd · 2.5 ba · 2,419 ft² · Sold $638K · Oct 2026
- 4617 Ardale St$350K3 bd · 2 ba · 1,291 ft² · Sold $360K · Oct 2026
- 811 Hampton Wood Ct$554K3 bd · 2 ba · 2,498 ft² · Sold $375K · Oct 2026
- 5337 Colewood Pl$425K4 bd · 3 ba · 2,362 ft² · Sold $425K · Oct 2026
Assigned schools
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