5408 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
5408 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 69% of homes in Milwaukee County
- Costs less per square foot than 78% of homes in Greendale 53129
- Has a smaller lot than 74% of homes in Greendale 53129
- 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 40% 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 40% of homes nearby
Pricier than 22% of homes nearby
Bigger than 58% of homes nearby
Bigger than 26% of homes nearby
Newer than 61% of homes nearby
| Measure | This home | Greendale 53129 | Milwaukee County |
|---|---|---|---|
| Estimated valuepricier than | $354,383 | 40% of homes | 69% of homes |
| Price per ft²pricier than | $204 | 22% of homes | 50% of homes |
| Living areabigger than | 1,736 ft² | 58% of homes | 64% of homes |
| Lot sizebigger than | 0.21 ac | 26% of homes | 73% of homes |
| Year builtnewer than | 1966 | 61% of homes | 80% of homes |
About 5408 Montgomery Dr
How much is 5408 Montgomery Dr, Greendale, WI worth?
The TopHap Estimate for 5408 Montgomery Dr, Greendale, WI is $354,383 as of Sep 24, 2026. The likely range is $321,705 to $387,061. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 5408 Montgomery Dr, Greendale, WI last sell?
5408 Montgomery Dr, Greendale, WI last sold on Nov 6, 1998 for $139,700, according to the county's recorded deed.
How big is 5408 Montgomery Dr, Greendale, WI?
5408 Montgomery Dr, Greendale, WI has 3 bedrooms, 1.5 bathrooms, 1,736 square feet of living space and a 0.21-acre lot.
When was 5408 Montgomery Dr, Greendale, WI built?
5408 Montgomery Dr, Greendale, WI was built in 1966, making it 60 years old. The building has 2 stories.
What schools serve 5408 Montgomery Dr, Greendale, WI?
5408 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 5408 Montgomery Dr, Greendale, WI compare to other homes in Greendale 53129?
Among the 4,467 homes in Greendale 53129, it is worth more than 40% of them ($354,383 against a typical $372,702), its price per square foot is higher than 22% of them ($204 against a typical $235), it is bigger than 58% of them (1,736 ft² against a typical 1,590 ft²), its lot is bigger than 26% of them (0.21 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 69% 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 5408 Montgomery Dr, Greendale, WI?
The 2025 property tax bill for 5408 Montgomery Dr, Greendale, WI was $2,742. The county assessed it at $312,400.
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
- 5406 Montgomery Dr$498K75 ft · 4 bd · 2 ba · 2,765 ft² · Sold $199K · Oct 2012
- 5410 Montgomery Dr$418K97 ft · 3 bd · 1.5 ba · 1,596 ft² · Sold $326K · Aug 2021
- 6809 Greenway$358K132 ft · 3 bd · 1.5 ba · 1,458 ft² · Sold Jan 1900
- 6805 Greenway$376K139 ft · 3 bd · 1.5 ba · 1,491 ft² · Sold $226K · Aug 2007
- 5400 Montgomery Dr$413K162 ft · 5 bd · 2 ba · 2,251 ft² · Sold $156K · Oct 1999
- 5412 Montgomery Dr$480K159 ft · 5 bd · 2 ba · 3,058 ft² · Sold $178K · Mar 2002
- 5413 Montgomery Dr$403K187 ft · 4 bd · 2 ba · 1,830 ft² · Sold Jan 1900
- 5409 Montgomery Dr$390K173 ft · 3 bd · 2.5 ba · 1,551 ft² · Sold Jan 1900
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
Explore the area
See this home in context
Open 5408 Montgomery Dr on TopHap’s interactive map to compare it against every sale nearby, overlay school zones and flood risk, and run a CMA.
Open in map