Apartments for Rent in the Highwood Estates Neighborhood of Milwaukee, WI (360 Rentals)

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An Insider's Guide to Apartment Living Near Milwaukee's Four Employer Clusters

Discover Milwaukee apartment living from Downtown lofts to affordable suburban homes. We detail neighborhoods near the four major employment hubs: urban, leafy, and everything in between.

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property at 3754 S 81st St

$1,825

Total Monthly Price

Total Monthly Price

Base Rent
$1,825
Total Monthly Price
$1,825

3 Bedroom, 1.5 Bath Townhome for Rent

Available Oct 23

3754 S 81st St

MilwaukeeWI53220
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3759 S 58th St, Unit Upper
$1,825
Total Monthly Price

Total Monthly Price

Base Rent
$1,825
Total Monthly Price
$1,825
3 Bedroom Apartment Available Sep 15

3759 S 58th St, Unit Upper

3759 S 58th StMilwaukee, WI 53220
Affordability
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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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property at 3819 S 74th St

$1,400

Total Monthly Price

Total Monthly Price

Base Rent
$1,400
Total Monthly Price
$1,400

2 Bedroom, 1 Bath Townhome for Rent

Available Sep 1

3819 S 74th St

MilwaukeeWI53220
property at 3655 S 90th St

$1,895

Total Monthly Price

Total Monthly Price

Base Rent
$1,895
Total Monthly Price
$1,895

3 Bedroom, 1.5 Bath Home for Rent

Available Now

3655 S 90th St

MilwaukeeWI53228
property at 4839 W Lynndale Ave

$1,700

Total Monthly Price

Total Monthly Price

Base Rent
$1,700
Total Monthly Price
$1,700

3 Bedroom, 1 Bath Townhome for Rent

Available Sep 1

4839 W Lynndale Ave

MilwaukeeWI53220

A Local Expert's Guide to Milwaukee: Neighborhoods, Traditions, and the Cozy Spirit of Gemütlichkeit

Uncover Milwaukee's affordable, vibrant neighborhoods and down-to-earth charm. Get a local expert's take on the city's renaissance, favorite traditions, and famous Gemütlichkeit (cozy spirit).

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Check Out Milwaukee’s Best Affordable Neighborhoods

Learn about Milwaukee and the best places to live with original content written by our Local Expert Tim Brown

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How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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Highwood Estates, Milwaukee, WI Local Guide

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.

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18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Tour smarter and choose with confidence. Get the essential 18 questions that reveal the truth about a rental property's maintenance, utilities, and safety.

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Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

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Quick Rent Budget Calculator

How much rent can you afford?

The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.

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Best Local Schools in
Highwood Estates, Milwaukee, WI

School data provided by Great Schools

Lifestyle Ratings

Our team is proud to bring you our detailed rental analysis called 'Lifestyle Ratings' - a comparison of rentals in areas across the United States and customized analysis for Southwestern Milwaukee, WI. LifeStyle Ratings are a useful tool for comparing and sorting apartments and neighborhoods when choosing your rental home. This takes in many factors including our Star Ratings to compare for proximity to parks, luxury amenities, kid and pet-friendly communities, availability of transit options, and other valuable search options. Use Lifestyle Search in the site filter options on this page - and find your Perfect place!

Family-Friendly Rating

Renting with a son or daughter (or both!)? Amongst all of the communities in Milwaukee, this residential submarket is known as one of our favorite neighborhoods for families, with a score of 4.0 out of 4. Family Friendly communities have features that support parents and kids in having fun and being healthy together. These features include things like green spaces, recreation and A/V rooms, trails, and access to highly-rated education resources.

Outdoors Rating

For some, access to parks and greenspace is a must-have. Highwood Estates is providing favorable access to nice outdoor spaces, with a score of 4.0 out of 4.

Luxury Living Rating

This residential area has come to be amongst the finest luxury submarkets in town, with a score of 4.0 out of 4. Luxury Lifestyle Scoring is based on having high-end community amenities like pools, saunas, workout spaces, maid services, park access, and amenities like granite countertops, range hoods, and high-end appliances. Luxury neighborhoods also often offer tile or hardwood floors, tennis courts, and for some communities, even a doorman to greet residents.

Pet Friendly Rating

There's good news if you raise furry friends. This part of Milwaukee ranks highly for raising pets (dogs and cats), with a score of 4.0 out of 4.

Frequently Asked Questions about Highwood Estates

What is the current pricing and availability for apartments for rent in the Highwood Estates area of Milwaukee, WI?

As of today, August 26, 2026, there are currently 360 available Highwood Estates apartments priced from $550 to $4,167, with an average monthly rent of $1,581.

How much are Studio apartments in Highwood Estates?

There are currently 40 Studio Apartments in Highwood Estates with rent ranges from $984 to $2,857 with an average price of $1,854.

What is the current price range for One Bedroom Highwood Estates Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Highwood Estates ranges from $550 to $3,523 with an average monthly rent of $1,460.

What does renting a Two Bedroom Apartment in Highwood Estates cost?

The monthly rent prices of Two Bedroom Apartments currently available in Highwood Estates range from $661 to $4,167. Today's average rental price for Two Bedrooms here is $1,610.

How expensive are Highwood Estates Three Bedroom Apartments?

There are currently 37 Three Bedroom Apartments listings available in Highwood Estates on ApartmentHomeLiving.com. The pricing ranges from $1,500 to $2,895 - averaging $2,001 for the location.

Expert Rental Resources

The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.

Helpful Local Expert Guides

decorative image for An Insider's Guide to Apartment Living Near Milwaukee's Four Employer Clusters article

An Insider's Guide to Apartment Living Near Milwaukee's Four Employer Clusters

Written by: Tim Brown

Having grown up in Milwaukee and lived in Waukesha for several years, I have come to realize that the Milwaukee metro area offers diverse employment and housing opportunities.

decorative image for A Local Expert's Guide to Milwaukee: Neighborhoods, Traditions, and the Cozy Spirit of Gemütlichkeit article

A Local Expert's Guide to Milwaukee: Neighborhoods, Traditions, and the Cozy Spirit of Gemütlichkeit

Written by: Tim Brown

I'm Tim, your ApartmentHomeLiving.com Local Expert for Milwaukee, Wisconsin. Growing up in the city and then blocks outside the border, Milwaukee's neighborhoods have been home to friends and family for years.

decorative image for The Top Neighborhoods for Off-Campus Housing for Milwaukee-Area College Students article

The Top Neighborhoods for Off-Campus Housing for Milwaukee-Area College Students

Written by: Tim Brown

I'm Tim, your ApartmentHomeLiving.com Local Expert for Milwaukee, Wisconsin. Growing up in the city and then blocks outside the border, many of the Milwaukee neighborhoods profiled here have been home to friends and family.

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Finding The Best Affordable Milwaukee Neighborhoods to Rent

Written by: Tim Brown

I'm Tim, your ApartmentHomeLiving.com Local Expert for Milwaukee, Wisconsin. Growing up in the city and then just blocks outside the border, many Milwaukee neighborhoods have been home to friends and family for many years.

Articles, How-To's, and Tips

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

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First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

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Apartment Occupancy Rates: Renter Attraction vs Renter Retention

Written by: Robin Stewart

There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.