4042 CHESSWOOD DR
Valuation
Tax & Assessment
Climate Risk
Scores 0–100; higher = greater projected risk.
Property Facts
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.
District: Pasco County School District
Neighborhood · ZIP 34691These 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
4042 Chesswood 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 81% of homes in Pasco County
- Smaller than 80% of homes in Pasco County
- Has a smaller lot than 73% of homes in Pasco County
- Older than 94% of homes in Pasco County
What homes are worth in Holiday 34691
Each bar is how many homes fall in that price range. The marker is this home.
This home is worth more than 42% of homes in Holiday 34691.
How it measures up in Holiday 34691
The dot is this home. The mark in the middle is the typical home in Holiday 34691.
Pricier than 42% of homes nearby
Pricier than 59% of homes nearby
Bigger than 45% of homes nearby
Bigger than 51% of homes nearby
Newer than 11% of homes nearby
| Measure | This home | Holiday 34691 | Pasco County |
|---|---|---|---|
| Estimated valuepricier than | $220,597 | 42% of homes | 19% of homes |
| Price per ft²pricier than | $188 | 59% of homes | 51% of homes |
| Living areabigger than | 1,173 ft² | 45% of homes | 20% of homes |
| Lot sizebigger than | 0.13 ac | 51% of homes | 27% of homes |
| Year builtnewer than | 1966 | 11% of homes | 6% of homes |
About 4042 Chesswood Dr
How much is 4042 Chesswood Dr, Holiday, FL worth?
The TopHap Estimate for 4042 Chesswood Dr, Holiday, FL is $220,597 as of Sep 24, 2026. The likely range is $212,264 to $228,930. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 4042 Chesswood Dr, Holiday, FL last sell?
4042 Chesswood Dr, Holiday, FL last sold on Mar 2, 2012 for $65,000, according to the county's recorded deed. TopHap holds 2 recorded sales for this parcel.
How big is 4042 Chesswood Dr, Holiday, FL?
4042 Chesswood Dr, Holiday, FL has 1.5 bathrooms, 1,173 square feet of living space and a 0.13-acre lot.
When was 4042 Chesswood Dr, Holiday, FL built?
4042 Chesswood Dr, Holiday, FL was built in 1966, making it 60 years old. The building has 1 story.
What schools serve 4042 Chesswood Dr, Holiday, FL?
4042 Chesswood Dr, Holiday, FL is assigned to Paul R. Smith Middle School (middle), rated D; Anclote High School (high), rated D+; Gulfside Elementary School (elementary), rated D-. All sit in Pasco County School District. Attendance boundaries change — confirm with the district before relying on an assignment.
How does 4042 Chesswood Dr, Holiday, FL compare to other homes in Holiday 34691?
Among the 11,181 homes in Holiday 34691, it is worth more than 42% of them ($220,597 against a typical $232,360), its price per square foot is higher than 59% of them ($188 against a typical $181), it is bigger than 45% of them (1,173 ft² against a typical 1,218 ft²), its lot is bigger than 51% of them (0.13 ac against a typical 0.13 ac) and it is newer than 11% of them (1966 against a typical 1972). Measured against all of Pasco County, it is worth more than 19% 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 4042 Chesswood Dr, Holiday, FL?
The 2025 property tax bill for 4042 Chesswood Dr, Holiday, FL was $980. The county assessed it at $89,470.
More homes on Chesswood Dr
- 4031 Chesswood Dr$224K1 ba · 1,224 ft² · Sold $225K · Aug 2026
- 4025 Chesswood Dr$140K1.5 ba · 1,257 ft² · Sold $145K · Jul 2025
- 4037 Chesswood Dr$210K1.5 ba · 1,124 ft² · Sold $219K · Jun 2025
- 4114 Chesswood Dr$219K1 ba · 988 ft² · Sold $230K · Mar 2025
- 4043 Chesswood Dr$208K1.5 ba · 988 ft² · Sold $222K · Jul 2023
- 4051 Chesswood Dr$217K1.5 ba · 1,128 ft² · Sold $252K · May 2022
- 4115 Chesswood Dr$235K2 ba · 1,464 ft² · Sold $14M · Apr 2022
- 4108 Chesswood Dr$230K1.5 ba · 1,084 ft² · Sold $216K · Dec 2021
- 4109 Chesswood Dr$193K1 ba · 1,306 ft² · Sold $125K · Jul 2020
- 4030 Chesswood Dr$195K1 ba · 816 ft² · Sold $76K · Jan 2020
- 4102 Chesswood Dr$225K1.5 ba · 1,464 ft² · Sold $130K · Dec 2018
- 4036 Chesswood Dr$197K2 ba · 916 ft² · Sold $44K · Oct 2017
Closest homes
- 4036 Chesswood Dr$197K61 ft · 2 ba · 916 ft² · Sold $44K · Oct 2017
- 4050 Chesswood Dr$199K61 ft · 1 ba · 1,092 ft² · Sold $38K · Jun 2013
- 4043 Ironware Dr$240K91 ft · 1.5 ba · 1,258 ft² · Sold $235K · Jan 2022
- 4051 Ironware Dr$190K109 ft · 1.5 ba · 956 ft² · Sold $69K · Jul 2004
- 4037 Ironware Dr$183K110 ft · 1 ba · 1,124 ft² · Sold $81K · Nov 2017
- 4030 Chesswood Dr$195K122 ft · 1 ba · 816 ft² · Sold $76K · Jan 2020
- 4102 Chesswood Dr$225K122 ft · 1.5 ba · 1,464 ft² · Sold $130K · Dec 2018
- 4043 Chesswood Dr$208K141 ft · 1.5 ba · 988 ft² · Sold $222K · Jul 2023
More homes in Holiday 34691
- 3609 Springfield Dr$253K2 ba · 1,470 ft² · Sold $250K · Oct 2026
- 2025 Shady Cove Dr1 ba · 668 ft² · Sold $50K · Oct 2026
- 3811 Cedarwood Dr$225K1.5 ba · 948 ft² · Sold $225K · Oct 2026
- 3636 Winder Dr$194K2 ba · 1,189 ft² · Sold $100 · Oct 2026
- 1447 Weyford Ln$185K1.5 ba · 1,047 ft² · Sold $185K · Oct 2026
- 3129 Holiday Lake Dr$194K1.5 ba · 1,323 ft² · Sold $168K · Oct 2026
- 2019 Hess Dr$225K1 ba · 984 ft² · Sold $225K · Oct 2026
- 1937 Us Highway 192 ba · 880 ft² · Sold $1.9M · Oct 2026
- 3750 Lighthouse Way$280K2 ba · 1,334 ft² · Sold $290K · Oct 2026
- 3521 Oakhurst Dr$200K1 ba · 1,026 ft² · Sold $200K · Oct 2026
- 2542 Sandy Hill Ct$350K2 ba · 2,019 ft² · Sold $329K · Oct 2026
- 3427 Pinon Dr$199K1 ba · 1,032 ft² · Sold $129K · Oct 2026
Assigned schools
Explore the area
See this home in context
Open 4042 Chesswood Dr on TopHap’s interactive map to compare it against every sale nearby, overlay school zones and flood risk, and run a CMA.
Open in map