27 CAYMAN 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: Oswego Community Unit School District 308
Neighborhood · ZIP 60538These 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
27 Cayman 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 67% of homes in Kendall County
- Costs more per square foot than 66% of homes in Kendall County
- Smaller than 71% of homes in Kendall County
- Has a smaller lot than 65% of homes in Kendall County
- Older than 86% of homes in Kendall County
What homes are worth in Montgomery 60538
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 Montgomery 60538.
How it measures up in Montgomery 60538
The dot is this home. The mark in the middle is the typical home in Montgomery 60538.
Pricier than 54% of homes nearby
Pricier than 58% of homes nearby
Bigger than 47% of homes nearby
Bigger than 54% of homes nearby
Newer than 28% of homes nearby
| Measure | This home | Montgomery 60538 | Kendall County |
|---|---|---|---|
| Estimated valuepricier than | $328,683 | 54% of homes | 33% of homes |
| Price per ft²pricier than | $210 | 58% of homes | 66% of homes |
| Living areabigger than | 1,568 ft² | 47% of homes | 29% of homes |
| Lot sizebigger than | 0.21 ac | 54% of homes | 35% of homes |
| Year builtnewer than | 1970 | 28% of homes | 14% of homes |
About 27 Cayman Dr
How much is 27 Cayman Dr, Montgomery, IL worth?
The TopHap Estimate for 27 Cayman Dr, Montgomery, IL is $328,683 as of Sep 24, 2026. The likely range is $311,502 to $345,864. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 27 Cayman Dr, Montgomery, IL last sell?
27 Cayman Dr, Montgomery, IL last sold on Oct 28, 2005 for $205,000, according to the county's recorded deed.
How big is 27 Cayman Dr, Montgomery, IL?
27 Cayman Dr, Montgomery, IL has 3 bedrooms, 1.5 bathrooms, 1,568 square feet of living space and a 0.21-acre lot.
When was 27 Cayman Dr, Montgomery, IL built?
27 Cayman Dr, Montgomery, IL was built in 1970, making it 56 years old. The building has 1 story.
What schools serve 27 Cayman Dr, Montgomery, IL?
27 Cayman Dr, Montgomery, IL is assigned to Boulder Hill Elementary School (elementary), rated B-; Thompson Junior High School (middle), rated C+; Oswego High School (high), rated A-. All sit in Oswego Community Unit School District 308. Attendance boundaries change — confirm with the district before relying on an assignment.
How does 27 Cayman Dr, Montgomery, IL compare to other homes in Montgomery 60538?
Among the 9,148 homes in Montgomery 60538, it is worth more than 54% of them ($328,683 against a typical $318,575), its price per square foot is higher than 58% of them ($210 against a typical $199), it is bigger than 47% of them (1,568 ft² against a typical 1,620 ft²), its lot is bigger than 54% of them (0.21 ac against a typical 0.21 ac) and it is newer than 28% of them (1970 against a typical 1998). Measured against all of Kendall County, it is worth more than 33% 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 27 Cayman Dr, Montgomery, IL?
The 2024 property tax bill for 27 Cayman Dr, Montgomery, IL was $6,366. The county assessed it at $96,907.
More homes on Cayman Dr
- 18 Cayman Dr$366K3 bd · 1.5 ba · 1,092 ft² · Sold $363K · Jul 2026
- 40 Cayman Dr$334K3 bd · 1 ba · 1,400 ft² · Sold $331K · Jul 2026
- 39 Cayman Dr$357K3 bd · 2 ba · 1,700 ft² · Sold $345K · Jan 2026
- 24 Cayman Dr$379K5 bd · 1 ba · 1,432 ft² · Sold $360K · Sep 2025
- 35 Cayman Dr$352K3 bd · 2 ba · 1,602 ft² · Sold Apr 2024
- 22 Cayman Dr$358K3 bd · 1 ba · 1,556 ft² · Sold $300K · Feb 2023
- 7 Cayman Dr$293K3 bd · 2 ba · 1,156 ft² · Sold $240K · Aug 2022
- 38 Cayman Dr$417K4 bd · 2 ba · 1,976 ft² · Sold $290K · Jan 2021
- 8 Cayman Dr$279K3 bd · 1 ba · 1,156 ft² · Sold $139K · Dec 2020
- 36 Cayman Dr$358K3 bd · 2 ba · 1,622 ft² · Sold $200K · Aug 2018
- 26 Cayman Dr$323K3 bd · 2 ba · 1,144 ft² · Sold $195K · Jul 2017
- 6 Cayman Dr$321K3 bd · 2 ba · 1,056 ft² · Sold $180K · Oct 2016
Closest homes
- 2 Cayman Ct$312K79 ft · 3 bd · 2 ba · 1,056 ft² · Sold $220K · Apr 2021
- 4 Cayman Ct$339K131 ft · 3 bd · 3 ba · 1,602 ft² · Sold $232K · Dec 2020
- 29 Cayman Dr$319K105 ft · 3 bd · 1 ba · 1,056 ft² · Sold $41K · Sep 1997
- 205 Boulder Hill Pass$310K120 ft · 3 bd · 1 ba · 1,324 ft² · Sold $170K · Jul 2016
- 203 Boulder Hill Pass$275K168 ft · 3 bd · 1 ba · 1,404 ft² · Sold Jan 1900
- 26 Cayman Dr$323K217 ft · 3 bd · 2 ba · 1,144 ft² · Sold $195K · Jul 2017
- 6 Cayman Ct$364K216 ft · 3 bd · 2 ba · 1,890 ft² · Sold $260K · Apr 2021
- 24 Cayman Dr$379K227 ft · 5 bd · 1 ba · 1,432 ft² · Sold $360K · Sep 2025
More homes in Montgomery 60538
- 2182 Kyla Ct$388K3 bd · 2 ba · 1,633 ft² · Sold $383K · Oct 2026
- 2466 Prescott Dr$466K4 bd · 2.5 ba · 2,668 ft² · Sold $462K · Sep 2026
- 1935 Springhaven Ct$389K3 bd · 1.5 ba · 1,819 ft² · Sold $390K · Sep 2026
- 135 Garden Dr$233K2 bd · 1 ba · 1,142 ft² · Sold $230K · Sep 2026
- 1805 Grandview Pl$270K2 bd · 2.5 ba · 1,434 ft² · Sold $270K · Sep 2026
- 125 Riverside Dr$295K3 bd · 1 ba · 900 ft² · Sold $295K · Sep 2026
- 3355 Big Bend Dr$445K3 bd · 2.5 ba · 2,108 ft² · Sold $438K · Sep 2026
- 1808 Candlelight Cir$301K1,754 ft² · Sold $301K · Sep 2026
- 3245 Millrace Ln$404K4 bd · 2.5 ba · 1,867 ft² · Sold $403K · Sep 2026
- 207 Hartway Ct$356K3 bd · 2.5 ba · 1,360 ft² · Sold $355K · Sep 2026
- 24 Marnel Rd$342K3 bd · 1 ba · 1,880 ft² · Sold $342K · Sep 2026
- 200 Fernwood Rd$360K3 bd · 2 ba · 1,512 ft² · Sold $348K · Sep 2026
Assigned schools
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