21 CASTLEWOOD 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: Monroe School District
Neighborhood · ZIP 06468These 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
21 Castlewood 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 Monroe 06468
- Smaller than 73% of homes in Monroe 06468
- Among the smallest lots in Monroe 06468
- Newer than 96% of homes in Monroe 06468
What homes are worth in Monroe 06468
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 Monroe 06468.
How it measures up in Monroe 06468
The dot is this home. The mark in the middle is the typical home in Monroe 06468.
Pricier than 18% of homes nearby
Pricier than 51% of homes nearby
Bigger than 27% of homes nearby
Smaller than almost all homes nearby
Newer than 96% of homes nearby
| Measure | This home | Monroe 06468 | Greater Bridgeport County |
|---|---|---|---|
| Estimated valuepricier than | $489,460 | 18% of homes | 37% of homes |
| Price per ft²pricier than | $312 | 51% of homes | 38% of homes |
| Living areabigger than | 1,568 ft² | 27% of homes | 44% of homes |
| Lot sizebigger than | 1,598 ft² | almost no homes | almost no homes |
| Year builtnewer than | 2005 | 96% of homes | 96% of homes |
About 21 Castlewood Dr
How much is 21 Castlewood Dr, Monroe, CT worth?
The TopHap Estimate for 21 Castlewood Dr, Monroe, CT is $489,460 as of Jul 14, 2026. The likely range is $462,196 to $516,724. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 21 Castlewood Dr, Monroe, CT last sell?
21 Castlewood Dr, Monroe, CT last sold on Sep 25, 2006 for $237,834, according to the county's recorded deed. TopHap holds 2 recorded sales for this parcel.
How big is 21 Castlewood Dr, Monroe, CT?
21 Castlewood Dr, Monroe, CT has 3 bedrooms, 2.5 bathrooms, 1,568 square feet of living space and a 0.04-acre lot.
When was 21 Castlewood Dr, Monroe, CT built?
21 Castlewood Dr, Monroe, CT was built in 2005, making it 21 years old. It is a condo/apartment home. The building has 2 stories.
What schools serve 21 Castlewood Dr, Monroe, CT?
21 Castlewood Dr, Monroe, CT is assigned to Jockey Hollow School (middle), rated A-; Fawn Hollow Elementary School (elementary), rated A+; Masuk High School (high), rated A+. All sit in Monroe School District. Attendance boundaries change — confirm with the district before relying on an assignment.
How does 21 Castlewood Dr, Monroe, CT compare to other homes in Monroe 06468?
Among the 6,749 homes in Monroe 06468, it is worth more than 18% of them ($489,460 against a typical $649,150), its price per square foot is higher than 51% of them ($312 against a typical $311), it is bigger than 27% of them (1,568 ft² against a typical 2,126 ft²), its lot is bigger than almost none of them (1,598 ft² against a typical 1.05 ac) and it is newer than 96% of them (2005 against a typical 1975). Measured against all of Greater Bridgeport County, it is worth more than 37% 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 21 Castlewood Dr, Monroe, CT?
The 2025 property tax bill for 21 Castlewood Dr, Monroe, CT was $5,598. The county assessed it at $195,272.
More homes on Castlewood Dr
- 7 Castlewood Dr$757K3 bd · 2.5 ba · 2,658 ft² · Sold $700K · Sep 2025
- 27 Castlewood Dr$698K3 bd · 3 ba · 2,232 ft² · Sold $599K · Dec 2024
- 38 Castlewood Dr$797K3 bd · 3.5 ba · 2,811 ft² · Sold $660K · Aug 2024
- 6 Castlewood Dr$737K3 bd · 2.5 ba · 2,218 ft² · Sold $575K · May 2024
- 11 Castlewood Dr$793K3 bd · 2.5 ba · 2,220 ft² · Sold $600K · Aug 2023
- 2 Castlewood Dr$799K3 bd · 2.5 ba · 2,279 ft² · Sold $575K · Jun 2023
- 9 Castlewood Dr$816K3 bd · 2.5 ba · 2,281 ft² · Sold $385K · Jan 2019
- 34 Castlewood Dr$786K3 bd · 2.5 ba · 2,281 ft² · Sold $321K · Oct 2018
- 15 Castlewood Dr$563K3 bd · 2.5 ba · 1,568 ft² · Sold $272K · May 2018
- 32 Castlewood Dr$546K3 bd · 2.5 ba · 1,568 ft² · Sold $285K · Jan 2017
- 23 Castlewood Dr$815K3 bd · 3 ba · 2,281 ft² · Sold $360K · Nov 2016
- 4 Castlewood Dr$774K3 bd · 2.5 ba · 2,281 ft² · Sold $430K · Apr 2016
Closest homes
- 34 Castlewood Dr$786K0 ft · 3 bd · 2.5 ba · 2,281 ft² · Sold $321K · Oct 2018
- 5 Stonecroft Way$768K0 ft · 3 bd · 2.5 ba · 2,140 ft² · Sold $570K · Aug 2022
- 25 Castlewood Dr$676K0 ft · 3 bd · 2.5 ba · 1,892 ft² · Sold $465K · May 2006
- 10 Stonecroft Way$585K0 ft · 3 bd · 2.5 ba · 2,140 ft² · Sold $153K · Dec 2005
- 7 Castlewood Dr$757K0 ft · 3 bd · 2.5 ba · 2,658 ft² · Sold $700K · Sep 2025
- 19 Castlewood Dr$813K0 ft · 3 bd · 2.5 ba · 2,281 ft² · Sold $4.6M · Jul 2005
- 8 Stonecroft Way$751K0 ft · 3 bd · 2.5 ba · 2,208 ft² · Sold $469K · Oct 2006
- 1 Stonecroft Way$719K0 ft · 3 bd · 2.5 ba · 2,281 ft² · Sold $370K · Jun 2012
More homes in Monroe 06468
- 94 Moosup Trl$299K4 bd · 2 ba · 1,512 ft² · Sold $270K · Aug 2026
- 18 Belle Vale St$699K4 bd · 2.5 ba · 2,512 ft² · Sold $740K · Aug 2026
- 6 Rosewood Cir1 bd · 1.5 ba · 1,444 ft² · Sold $420K · Aug 2026
- 368 Webb Cir$450K3 bd · 1 ba · 1,314 ft² · Sold $429K · Aug 2026
- 104 Cutlers Farm Rd$942K4 bd · 3.5 ba · 3,296 ft² · Sold $978K · Aug 2026
- 95 Bart Rd$730K4 bd · 3 ba · 2,628 ft² · Sold $730K · Aug 2026
- 53 Hidden Knolls Cir$231K1 bd · 1 ba · 765 ft² · Sold $205K · Aug 2026
- 6 Deepwood Cir$414K1 bd · 1.5 ba · 1,444 ft² · Sold $455K · Aug 2026
- 3 Stonecroft Way$794K3 bd · 2.5 ba · 2,281 ft² · Sold $635K · Aug 2026
- 109 Gay Bower Rd$699K4 bd · 2.5 ba · 2,730 ft² · Sold $710K · Aug 2026
- 34 Overlook Dr$400K1 bd · 1.5 ba · 1,444 ft² · Sold $420K · Jul 2026
- 30 Block Farm Rd$949K4 bd · 3.5 ba · 4,728 ft² · Sold $935K · Jul 2026
Assigned schools
Explore the area
See this home in context
Open 21 Castlewood 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