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 72% 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 28% 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 28% of homes nearby
Pricier than 44% 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 | $333,562 | 28% of homes | 65% of homes |
| Price per ft²pricier than | $229 | 44% of homes | 64% of homes |
| Living areabigger than | 1,459 ft² | 38% of homes | 49% 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 $333,562 as of Aug 30, 2026. The likely range is $308,877 to $358,247. 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 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 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 28% of them ($333,562 against a typical $370,418), its price per square foot is higher than 44% of them ($229 against a typical $235), it is bigger than 38% of them (1,459 ft² against a typical 1,588 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 65% 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$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
- 5416 Middleton Dr$338K3 bd · 1.5 ba · 1,092 ft² · Sold $215K · Jun 2017
- 5321 Middleton Dr$304K4 bd · 1.5 ba · 2,156 ft² · Sold $105K · Apr 2017
Closest homes
- 5412 Middleton Dr$320K64 ft · 3 bd · 2 ba · 1,243 ft² · Sold $150K · Mar 2010
- 5416 Middleton Dr$338K65 ft · 3 bd · 1.5 ba · 1,092 ft² · Sold $215K · Jun 2017
- 5420 Middleton Dr$354K130 ft · 2 bd · 1.5 ba · 1,107 ft² · Sold $260K · May 2020
- 5408 Middleton Dr$327K128 ft · 4 bd · 1.5 ba · 1,252 ft² · Sold $170K · Jun 2013
- 5417 Mansfield Dr$278K128 ft · 3 bd · 1 ba · 1,020 ft² · Sold Jan 1900
- 5413 Mansfield Dr$355K128 ft · 3 bd · 1.5 ba · 1,591 ft² · Sold Jan 1900
- 5421 Mansfield Dr$339K170 ft · 3 bd · 1 ba · 1,369 ft² · Sold Jan 1900
- 5426 Middleton Dr$401K203 ft · 3 bd · 1.5 ba · 1,194 ft² · Sold $400K · Jul 2026
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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