5414 MIDDLETON DR
Valuation
Tax & Assessment
Climate Risk
Scores 0–100; higher = greater projected risk.
Property Facts
Transaction History(4)
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: Greendale School District
Neighborhood · ZIP 53129These 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
5414 Middleton 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 78% of homes in Greendale 53129
- Costs less per square foot than 65% of homes in Greendale 53129
- Has a smaller lot than 81% of homes in Greendale 53129
- Newer than 73% of homes in Milwaukee County
What homes are worth in Greendale 53129
Each bar is how many homes fall in that price range. The marker is this home.
This home is worth more than 22% of homes in Greendale 53129.
How it measures up in Greendale 53129
The dot is this home. The mark in the middle is the typical home in Greendale 53129.
Pricier than 22% of homes nearby
Pricier than 35% of homes nearby
Bigger than 38% of homes nearby
Bigger than 19% of homes nearby
Newer than 31% of homes nearby
| Measure | This home | Greendale 53129 | Milwaukee County |
|---|---|---|---|
| Estimated valuepricier than | $319,853 | 22% of homes | 61% of homes |
| Price per ft²pricier than | $219 | 35% of homes | 58% of homes |
| Living areabigger than | 1,459 ft² | 38% of homes | 50% of homes |
| Lot sizebigger than | 0.19 ac | 19% of homes | 70% of homes |
| Year builtnewer than | 1959 | 31% of homes | 73% of homes |
About 5414 Middleton Dr
How much is 5414 Middleton Dr, Greendale, WI worth?
The TopHap Estimate for 5414 Middleton Dr, Greendale, WI is $319,853 as of Sep 24, 2026. The likely range is $293,303 to $346,403. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 5414 Middleton Dr, Greendale, WI last sell?
5414 Middleton Dr, Greendale, WI last sold on Nov 11, 2011 for $74,300, according to the county's recorded deed.
How big is 5414 Middleton Dr, Greendale, WI?
5414 Middleton Dr, Greendale, WI has 3 bedrooms, 1.5 bathrooms, 1,459 square feet of living space and a 0.19-acre lot.
When was 5414 Middleton Dr, Greendale, WI built?
5414 Middleton Dr, Greendale, WI was built in 1959, making it 67 years old. The building has 1 story.
What schools serve 5414 Middleton Dr, Greendale, WI?
5414 Middleton Dr, Greendale, WI is assigned to Greendale Middle School (middle), rated A; Greendale High School (high), rated A+; Highland View Elementary School (elementary), rated B+. All sit in Greendale School District. Attendance boundaries change — confirm with the district before relying on an assignment.
How does 5414 Middleton Dr, Greendale, WI compare to other homes in Greendale 53129?
Among the 4,467 homes in Greendale 53129, it is worth more than 22% of them ($319,853 against a typical $371,809), its price per square foot is higher than 35% of them ($219 against a typical $234), it is bigger than 38% of them (1,459 ft² against a typical 1,590 ft²), its lot is bigger than 19% of them (0.19 ac against a typical 0.25 ac) and it is newer than 31% of them (1959 against a typical 1964). Measured against all of Milwaukee County, it is worth more than 61% 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 5414 Middleton Dr, Greendale, WI?
The 2025 property tax bill for 5414 Middleton Dr, Greendale, WI was $2,776. The county assessed it at $305,800.
More homes on Middleton Dr
- 5426 Middleton Dr$403K3 bd · 1.5 ba · 1,194 ft² · Sold $400K · Jul 2026
- 5413 Middleton Dr$382K3 bd · 2 ba · 1,829 ft² · Sold $360K · May 2025
- 5324 Middleton Dr$335K3 bd · 1.5 ba · 1,210 ft² · Sold $327K · Aug 2023
- 5405 Middleton Dr$379K3 bd · 1 ba · 1,101 ft² · Sold $338K · May 2023
- 5404 Middleton Dr$301K3 bd · 1.5 ba · 1,097 ft² · Sold $181K · Sep 2020
- 5420 Middleton Dr$367K2 bd · 1.5 ba · 1,107 ft² · Sold $260K · May 2020
- 5312 Middleton Dr$351K2 bd · 1 ba · 1,221 ft² · Sold $263K · Sep 2019
- 5421 Middleton Dr$427K3 bd · 1 ba · 1,624 ft² · Sold $300K · Jun 2018
- 5318 Middleton Dr$341K2 bd · 1.5 ba · 1,247 ft² · Sold $225K · Jan 2018
- 5309 Middleton Dr$351K3 bd · 2 ba · 1,200 ft² · Sold $195K · Nov 2017
- 5416 Middleton Dr$355K3 bd · 1.5 ba · 1,092 ft² · Sold $215K · Jun 2017
- 5321 Middleton Dr$306K4 bd · 1.5 ba · 2,156 ft² · Sold $105K · Apr 2017
Closest homes
- 5412 Middleton Dr$316K64 ft · 3 bd · 2 ba · 1,243 ft² · Sold $150K · Mar 2010
- 5416 Middleton Dr$355K65 ft · 3 bd · 1.5 ba · 1,092 ft² · Sold $215K · Jun 2017
- 5420 Middleton Dr$367K130 ft · 2 bd · 1.5 ba · 1,107 ft² · Sold $260K · May 2020
- 5408 Middleton Dr$329K128 ft · 4 bd · 1.5 ba · 1,252 ft² · Sold $170K · Jun 2013
- 5417 Mansfield Dr$266K128 ft · 3 bd · 1 ba · 1,020 ft² · Sold Jan 1900
- 5413 Mansfield Dr$361K128 ft · 3 bd · 1.5 ba · 1,591 ft² · Sold Jan 1900
- 5421 Mansfield Dr$330K170 ft · 3 bd · 1 ba · 1,369 ft² · Sold Jan 1900
- 5426 Middleton Dr$403K203 ft · 3 bd · 1.5 ba · 1,194 ft² · Sold $400K · Jul 2026
More homes in Greendale 53129
- 8894 Greenmeadow Ln$599K3,281 ft² · Sold $616K · Oct 2026
- 5879 Ramona Dr$349K3 bd · 1.5 ba · 1,514 ft² · Sold $431K · Oct 2026
- 4800 Sussex Ln$447K3 bd · 1.5 ba · 1,818 ft² · Sold $493K · Oct 2026
- 5800 Lakeview Dr$393K3 bd · 1.5 ba · 1,736 ft² · Sold $300K · Oct 2026
- 4954 S 79th St$385K3 bd · 1.5 ba · 1,651 ft² · Sold $400K · Oct 2026
- 5152 Maplewood Dr$372K3 bd · 2.5 ba · 1,596 ft² · Sold $172K · Oct 2026
- 5111 Maplewood Dr$490K2,812 ft² · Sold $435K · Oct 2026
- 8880 Garden Ln$439K3 bd · 2 ba · 1,816 ft² · Sold $465K · Sep 2026
- 5208 Millbank Rd$470K3 bd · 2 ba · 1,395 ft² · Sold $470K · Sep 2026
- 6109 Thornridge Ln$425K3 bd · 1.5 ba · 1,466 ft² · Sold $435K · Sep 2026
- 6619 Manchester Dr$350K3 bd · 1 ba · 1,124 ft² · Sold $350K · Sep 2026
- 6712 Manchester Dr$390K3 bd · 1.5 ba · 2,594 ft² · Sold $390K · Sep 2026
Assigned schools
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