5416 MIDDLETON DR
Valuation
Tax & Assessment
Climate Risk
Scores 0–100; higher = greater projected risk.
Property Facts
Transaction History(3)
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
5416 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 70% of homes in Greendale 53129
- Costs more per square foot than 92% of homes in Milwaukee County
- Smaller than 92% of homes in Greendale 53129
- Has a smaller lot than 84% of homes in Greendale 53129
- Older than 78% of homes in Greendale 53129
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 30% 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 30% of homes nearby
Pricier than 91% of homes nearby
Bigger than 8% of homes nearby
Bigger than 16% of homes nearby
Newer than 22% of homes nearby
| Measure | This home | Greendale 53129 | Milwaukee County |
|---|---|---|---|
| Estimated valuepricier than | $337,798 | 30% of homes | 66% of homes |
| Price per ft²pricier than | $309 | 91% of homes | 92% of homes |
| Living areabigger than | 1,092 ft² | 8% of homes | 22% of homes |
| Lot sizebigger than | 0.18 ac | 16% of homes | 67% of homes |
| Year builtnewer than | 1958 | 22% of homes | 71% of homes |
About 5416 Middleton Dr
How much is 5416 Middleton Dr, Greendale, WI worth?
The TopHap Estimate for 5416 Middleton Dr, Greendale, WI is $337,798 as of Aug 30, 2026. The likely range is $323,737 to $351,859. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 5416 Middleton Dr, Greendale, WI last sell?
5416 Middleton Dr, Greendale, WI last sold on Jun 19, 2017 for $215,200, according to the county's recorded deed. TopHap holds 2 recorded sales for this parcel.
How big is 5416 Middleton Dr, Greendale, WI?
5416 Middleton Dr, Greendale, WI has 3 bedrooms, 1.5 bathrooms, 1,092 square feet of living space and a 0.18-acre lot.
When was 5416 Middleton Dr, Greendale, WI built?
5416 Middleton Dr, Greendale, WI was built in 1958, making it 68 years old. The building has 1 story.
What schools serve 5416 Middleton Dr, Greendale, WI?
5416 Middleton Dr, Greendale, WI is assigned to Greendale Middle School (middle), rated A-; Greendale High School (high), rated B+; Highland View Elementary School (elementary), rated A-. All sit in Greendale School District. Attendance boundaries change — confirm with the district before relying on an assignment.
How does 5416 Middleton Dr, Greendale, WI compare to other homes in Greendale 53129?
Among the 4,467 homes in Greendale 53129, it is worth more than 30% of them ($337,798 against a typical $370,382), its price per square foot is higher than 91% of them ($309 against a typical $235), it is bigger than 8% of them (1,092 ft² against a typical 1,591 ft²), its lot is bigger than 16% of them (0.18 ac against a typical 0.25 ac) and it is newer than 22% of them (1958 against a typical 1964). Measured against all of Milwaukee County, it is worth more than 66% 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 5416 Middleton Dr, Greendale, WI?
The 2025 property tax bill for 5416 Middleton Dr, Greendale, WI was $2,593. The county assessed it at $296,200.
More homes on Middleton Dr
- 5426 Middleton Dr$401K3 bd · 1.5 ba · 1,194 ft² · Sold $400K · Jul 2026
- 5413 Middleton Dr$378K3 bd · 2 ba · 1,829 ft² · Sold $360K · May 2025
- 5324 Middleton Dr$334K3 bd · 1.5 ba · 1,210 ft² · Sold $327K · Aug 2023
- 5405 Middleton Dr$374K3 bd · 1 ba · 1,101 ft² · Sold $338K · May 2023
- 5404 Middleton Dr$300K3 bd · 1.5 ba · 1,097 ft² · Sold $181K · Sep 2020
- 5420 Middleton Dr$354K2 bd · 1.5 ba · 1,107 ft² · Sold $260K · May 2020
- 5312 Middleton Dr$348K2 bd · 1 ba · 1,221 ft² · Sold $263K · Sep 2019
- 5421 Middleton Dr$426K3 bd · 1 ba · 1,624 ft² · Sold $300K · Jun 2018
- 5318 Middleton Dr$329K2 bd · 1.5 ba · 1,247 ft² · Sold $225K · Jan 2018
- 5309 Middleton Dr$332K3 bd · 2 ba · 1,200 ft² · Sold $195K · Nov 2017
- 5321 Middleton Dr$304K4 bd · 1.5 ba · 2,156 ft² · Sold $105K · Apr 2017
- 5409 Middleton Dr$357K3 bd · 1.5 ba · 1,409 ft² · Sold $183K · Jan 2016
Closest homes
- 5420 Middleton Dr$354K65 ft · 2 bd · 1.5 ba · 1,107 ft² · Sold $260K · May 2020
- 5414 Middleton Dr$334K65 ft · 3 bd · 1.5 ba · 1,459 ft² · Sold $74K · Nov 2011
- 5412 Middleton Dr$320K129 ft · 3 bd · 2 ba · 1,243 ft² · Sold $150K · Mar 2010
- 5426 Middleton Dr$401K140 ft · 3 bd · 1.5 ba · 1,194 ft² · Sold $400K · Jul 2026
- 5417 Mansfield Dr$278K123 ft · 3 bd · 1 ba · 1,020 ft² · Sold Jan 1900
- 5421 Mansfield Dr$339K137 ft · 3 bd · 1 ba · 1,369 ft² · Sold Jan 1900
- 5408 Middleton Dr$327K193 ft · 4 bd · 1.5 ba · 1,252 ft² · Sold $170K · Jun 2013
- 5413 Mansfield Dr$355K159 ft · 3 bd · 1.5 ba · 1,591 ft² · Sold Jan 1900
More homes in Greendale 53129
- 5989 Sugarbush Ln$436K0.23 ac · Sold $436K · Aug 2026
- 6131 Twin Oak Dr$361K3 bd · 1.5 ba · 1,483 ft² · Sold $390K · Aug 2026
- 7227 Edgehill Rd$326K4 bd · 1.5 ba · 1,151 ft² · Sold $326K · Aug 2026
- 7232 Dartmoor Ave$588K3 bd · 1.5 ba · 1,244 ft² · Sold $588K · Aug 2026
- 5806 Glen Flora Dr$478K3 bd · 1.5 ba · 3,087 ft² · Sold $478K · Aug 2026
- 6401 W Edgerton Ave$450K4 bd · 2 ba · 1,815 ft² · Sold $450K · Aug 2026
- 8841 Greenhill Ln$370K3 bd · 2 ba · 1,772 ft² · Sold $370K · Aug 2026
- 7222 Enfield Ave$390K3 bd · 1.5 ba · 1,160 ft² · Sold $390K · Aug 2026
- 5594 Arrowwood St$290K3 bd · 1 ba · 1,276 ft² · Sold $290K · Aug 2026
- 5611 Apricot Ct$255K2 bd · 1 ba · 1,150 ft² · Sold $255K · Aug 2026
- 6085 Trail Ridge Dr$420K4 bd · 1.5 ba · 2,176 ft² · Sold $420K · Aug 2026
- 5249 Lakeside Dr$400K3 bd · 1.5 ba · 1,483 ft² · Sold $400K · Aug 2026
Assigned schools
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