5414 MONTGOMERY 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: 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 Montgomery 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 more than 80% of homes in Milwaukee County
- Costs more per square foot than 81% of homes in Milwaukee County
- Has a bigger lot than 91% of homes in Milwaukee County
- Newer than 80% 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 68% 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 68% of homes nearby
Pricier than 76% of homes nearby
Bigger than 45% of homes nearby
Bigger than 84% of homes nearby
Newer than 61% of homes nearby
| Measure | This home | Greendale 53129 | Milwaukee County |
|---|---|---|---|
| Estimated valuepricier than | $415,991 | 68% of homes | 80% of homes |
| Price per ft²pricier than | $268 | 76% of homes | 81% of homes |
| Living areabigger than | 1,552 ft² | 45% of homes | 55% of homes |
| Lot sizebigger than | 0.4 ac | 84% of homes | 91% of homes |
| Year builtnewer than | 1966 | 61% of homes | 80% of homes |
About 5414 Montgomery Dr
How much is 5414 Montgomery Dr, Greendale, WI worth?
The TopHap Estimate for 5414 Montgomery Dr, Greendale, WI is $415,991 as of Sep 24, 2026. The likely range is $379,804 to $452,178. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 5414 Montgomery Dr, Greendale, WI last sell?
5414 Montgomery Dr, Greendale, WI last sold on Jul 17, 2012 for $197,500, according to the county's recorded deed.
How big is 5414 Montgomery Dr, Greendale, WI?
5414 Montgomery Dr, Greendale, WI has 3 bedrooms, 1.5 bathrooms, 1,552 square feet of living space and a 0.40-acre lot.
When was 5414 Montgomery Dr, Greendale, WI built?
5414 Montgomery Dr, Greendale, WI was built in 1966, making it 60 years old. The building has 1 story.
What schools serve 5414 Montgomery Dr, Greendale, WI?
5414 Montgomery 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 Montgomery Dr, Greendale, WI compare to other homes in Greendale 53129?
Among the 4,467 homes in Greendale 53129, it is worth more than 68% of them ($415,991 against a typical $372,702), its price per square foot is higher than 76% of them ($268 against a typical $235), it is bigger than 45% of them (1,552 ft² against a typical 1,590 ft²), its lot is bigger than 84% of them (0.4 ac against a typical 0.25 ac) and it is newer than 61% of them (1966 against a typical 1964). Measured against all of Milwaukee County, it is worth more than 80% 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 Montgomery Dr, Greendale, WI?
The 2025 property tax bill for 5414 Montgomery Dr, Greendale, WI was $3,152. The county assessed it at $357,000.
More homes on Montgomery Dr
- 5438 Montgomery Dr$431K4 bd · 2.5 ba · 2,137 ft² · Sold $399K · Dec 2024
- 6733 Montgomery Dr$398K3 bd · 1.5 ba · 1,124 ft² · Sold $360K · Aug 2023
- 6631 Montgomery Dr$432K3 bd · 1.5 ba · 1,102 ft² · Sold $348K · Oct 2022
- 6644 Montgomery Dr$358K3 bd · 1.5 ba · 1,145 ft² · Sold $308K · May 2022
- 6701 Montgomery Dr$340K0.39 ac · Sold Jan 2022
- 5425 Montgomery Dr$413K3 bd · 2 ba · 1,407 ft² · Sold $325K · Sep 2021
- 5410 Montgomery Dr$418K3 bd · 1.5 ba · 1,596 ft² · Sold $326K · Aug 2021
- 5429 Montgomery Dr$627K5 bd · 2.5 ba · 3,003 ft² · Sold $327K · Nov 2018
- 5417 Montgomery Dr$413K4 bd · 2.5 ba · 1,725 ft² · Sold $230K · Jun 2018
- 6730 Montgomery Dr$351K3 bd · 1 ba · 1,371 ft² · Sold $186K · Mar 2017
- 6720 Montgomery Dr$337K3 bd · 1 ba · 1,043 ft² · Sold $150K · Jan 2017
- 5433 Montgomery Dr$496K3 bd · 1.5 ba · 1,904 ft² · Sold $268K · Oct 2014
Closest homes
- 5412 Montgomery Dr$480K119 ft · 5 bd · 2 ba · 3,058 ft² · Sold $178K · Mar 2002
- 5418 Montgomery Dr$367K95 ft · 3 bd · 1.5 ba · 1,657 ft² · Sold Jan 1900
- 5426 Montgomery Dr$377K128 ft · 4 bd · 1.5 ba · 1,836 ft² · Sold $210K · Jul 2013
- 5444 Montgomery Dr$406K196 ft · 4 bd · 2.5 ba · 2,177 ft² · Sold Jan 1900
- 5410 Montgomery Dr$418K202 ft · 3 bd · 1.5 ba · 1,596 ft² · Sold $326K · Aug 2021
- 5438 Montgomery Dr$431K207 ft · 4 bd · 2.5 ba · 2,137 ft² · Sold $399K · Dec 2024
- 5408 Montgomery Dr$354K245 ft · 3 bd · 1.5 ba · 1,736 ft² · Sold $140K · Nov 1998
- 5486 Moorehead Ln$364K216 ft · 1,078 ft² · Sold $130K · Aug 2011
More homes in Greendale 53129
- 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
- 7003 Dryden Ct$300K3 bd · 1.5 ba · 2,047 ft² · Sold $300K · Sep 2026
- 5818 Currant Ln$340K3 bd · 1 ba · 1,276 ft² · Sold $340K · Sep 2026
- 5888 Riverside Dr$387K4 bd · 1.5 ba · 1,847 ft² · Sold $420K · Sep 2026
- 5576 Angle Ln$340K3 bd · 1 ba · 1,276 ft² · Sold $340K · Sep 2026
- 8246 Firwood Ln$784K4 bd · 2.5 ba · 2,995 ft² · Sold $784K · Sep 2026
- 9111 Westlake Dr$321K0.13 ac · Sold $320K · Aug 2026
- 5792 Finch Ln$803K3 bd · 2 ba · 1,568 ft² · Sold $800K · Aug 2026
- 5989 Sugarbush Ln$438K0.23 ac · Sold $436K · Aug 2026
- 6131 Twin Oak Dr$392K3 bd · 1.5 ba · 1,483 ft² · Sold $390K · Aug 2026
- 7227 Edgehill Rd$327K4 bd · 1.5 ba · 1,151 ft² · Sold $326K · Aug 2026
Assigned schools
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