5429 MONTGOMERY DR
Valuation
Tax & Assessment
Climate Risk
Scores 0–100; higher = greater projected risk.
Property Facts
Transaction History(6)
Sales and refinances filed with the county for this home. Not every transfer is a normal sale, so check the type before comparing prices.Foreclosure Filings(1)
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
5429 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 95% of homes in Greendale 53129
- Costs less per square foot than 76% of homes in Greendale 53129
- Bigger than 95% of homes in Milwaukee County
- Has a bigger lot than 74% of homes in Milwaukee County
- Newer than 81% 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 95% 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 95% of homes nearby
Pricier than 24% of homes nearby
Bigger than 94% of homes nearby
Bigger than 28% of homes nearby
Newer than 68% of homes nearby
| Measure | This home | Greendale 53129 | Milwaukee County |
|---|---|---|---|
| Estimated valuepricier than | $611,088 | 95% of homes | 94% of homes |
| Price per ft²pricier than | $203 | 24% of homes | 50% of homes |
| Living areabigger than | 3,003 ft² | 94% of homes | 95% of homes |
| Lot sizebigger than | 0.21 ac | 28% of homes | 74% of homes |
| Year builtnewer than | 1967 | 68% of homes | 81% of homes |
About 5429 Montgomery Dr
How much is 5429 Montgomery Dr, Greendale, WI worth?
The TopHap Estimate for 5429 Montgomery Dr, Greendale, WI is $611,088 as of Aug 30, 2026. The likely range is $577,464 to $644,712. The estimate is modelled from recorded sales, assessments and the property's own characteristics — it is not an appraisal.
When did 5429 Montgomery Dr, Greendale, WI last sell?
5429 Montgomery Dr, Greendale, WI last sold on Nov 5, 2018 for $327,000, according to the county's recorded deed. TopHap holds 2 recorded sales for this parcel.
How big is 5429 Montgomery Dr, Greendale, WI?
5429 Montgomery Dr, Greendale, WI has 5 bedrooms, 2.5 bathrooms, 3,003 square feet of living space and a 0.21-acre lot.
When was 5429 Montgomery Dr, Greendale, WI built?
5429 Montgomery Dr, Greendale, WI was built in 1967, making it 59 years old. The building has 1 story.
What schools serve 5429 Montgomery Dr, Greendale, WI?
5429 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 5429 Montgomery Dr, Greendale, WI compare to other homes in Greendale 53129?
Among the 4,467 homes in Greendale 53129, it is worth more than 95% of them ($611,088 against a typical $370,630), its price per square foot is higher than 24% of them ($203 against a typical $234), it is bigger than 94% of them (3,003 ft² against a typical 1,590 ft²), its lot is bigger than 28% of them (0.21 ac against a typical 0.25 ac) and it is newer than 68% of them (1967 against a typical 1964). Measured against all of Milwaukee County, it is worth more than 94% 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 5429 Montgomery Dr, Greendale, WI?
The 2025 property tax bill for 5429 Montgomery Dr, Greendale, WI was $4,733. The county assessed it at $529,200.
More homes on Montgomery Dr
- 5438 Montgomery Dr$426K4 bd · 2.5 ba · 2,137 ft² · Sold $399K · Dec 2024
- 6733 Montgomery Dr$394K3 bd · 1.5 ba · 1,124 ft² · Sold $360K · Aug 2023
- 6631 Montgomery Dr$394K3 bd · 1.5 ba · 1,102 ft² · Sold $348K · Oct 2022
- 6644 Montgomery Dr$346K3 bd · 1.5 ba · 1,145 ft² · Sold $308K · May 2022
- 6701 Montgomery Dr$319K0.39 ac · Sold Jan 2022
- 5425 Montgomery Dr$408K3 bd · 2 ba · 1,407 ft² · Sold $325K · Sep 2021
- 5410 Montgomery Dr$398K3 bd · 1.5 ba · 1,596 ft² · Sold $326K · Aug 2021
- 5417 Montgomery Dr$408K4 bd · 2.5 ba · 1,725 ft² · Sold $230K · Jun 2018
- 6730 Montgomery Dr$335K3 bd · 1 ba · 1,371 ft² · Sold $186K · Mar 2017
- 6720 Montgomery Dr$308K3 bd · 1 ba · 1,043 ft² · Sold $150K · Jan 2017
- 5433 Montgomery Dr$472K3 bd · 1.5 ba · 1,904 ft² · Sold $268K · Oct 2014
- 5426 Montgomery Dr$380K4 bd · 1.5 ba · 1,836 ft² · Sold $210K · Jul 2013
Closest homes
- 5425 Montgomery Dr$408K85 ft · 3 bd · 2 ba · 1,407 ft² · Sold $325K · Sep 2021
- 5433 Montgomery Dr$472K123 ft · 3 bd · 1.5 ba · 1,904 ft² · Sold $268K · Oct 2014
- 5421 Montgomery Dr$393K163 ft · 5 bd · 2.5 ba · 1,581 ft² · Sold $184K · Jul 2000
- 5437 Montgomery Dr$527K199 ft · 3,625 ft² · Sold $141K · Jul 2012
- 5417 Montgomery Dr$408K240 ft · 4 bd · 2.5 ba · 1,725 ft² · Sold $230K · Jun 2018
- 5438 Montgomery Dr$426K213 ft · 4 bd · 2.5 ba · 2,137 ft² · Sold $399K · Dec 2024
- 5413 Montgomery Dr$408K314 ft · 4 bd · 2 ba · 1,830 ft² · Sold Jan 1900
- 5426 Montgomery Dr$380K252 ft · 4 bd · 1.5 ba · 1,836 ft² · Sold $210K · Jul 2013
More homes in Greendale 53129
- 5818 Currant Ln$340K3 bd · 1 ba · 1,276 ft² · Sold $340K · Sep 2026
- 5888 Riverside Dr$425K4 bd · 1.5 ba · 1,847 ft² · Sold $420K · Sep 2026
- 5576 Angle Ln$345K3 bd · 1 ba · 1,276 ft² · Sold $340K · Sep 2026
- 8246 Firwood Ln$760K4 bd · 2.5 ba · 2,995 ft² · Sold $784K · Sep 2026
- 9111 Westlake Dr$330K0.13 ac · Sold $320K · Aug 2026
- 5792 Finch Ln$800K3 bd · 2 ba · 1,568 ft² · Sold $800K · Aug 2026
- 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
Assigned schools
Explore the area
See this home in context
Open 5429 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