Cheap Apartments for Rent in the Highwood Estates Neighborhood of Milwaukee, WI from $300 (48 Rentals)

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Search the lowest-cost Apartments available for rent right now in the Highwood Estates area of Milwaukee.

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3229 S 99th St
2 Bedroom Apartments

3229 S 99th St

3229 S 99th StMilwaukee, WI 53227
  • Utilities Included
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RES Apartments
1 to 2 Bedroom Apartments

RES Apartments

3301 S 100th StMilwaukee, WI 53227
  • Utilities Included

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.

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3235 S 48th St
1 Bedroom Apartments

3235 S 48th St

3235 S 48th StMilwaukee, WI 53219
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Hamilton Manor
1 to 2 Bedroom Apartments

Hamilton Manor

3700 S 61st StMilwaukee, WI 53220
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WestGlen
Studio to 1 Bedroom Apartments

WestGlen

7902 W National AveMilwaukee, WI 53214
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4138 S 51st St
1 to 2 Bedroom Apartments

4138 S 51st St

4138 S 51st StMilwaukee, WI 53220
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Becher Apartments
2 Bedroom Apartments

Becher Apartments

7726 W Becher StMilwaukee, WI 53219
Furnished
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9641-9651 W Beloit Rd
2 Bedroom Apartments

9641-9651 W Beloit Rd

9641-9651 W Beloit RdMilwaukee, WI 53227
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Roommate Matching: Finding the Right Fit and Avoiding Pitfalls

When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.

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Forrest Park
2 Bedroom Apartments

Forrest Park

3741 S 61st StMilwaukee, WI 53220
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6500 W Howard Avenue
2 Bedroom Apartments

6500 W Howard Avenue

6500 W Howard AveMilwaukee, WI 53220
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The Art of the Rental Viewing: What to look for during a property tour

Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

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2628 S 84th St
1 Bedroom Apartments

2628 S 84th St

2628 S 84th StWest Allis, WI 53227
  • Utilities Included

Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

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3046 S 99th St
2 Bedroom Apartments

3046 S 99th St

3046 S 99th StWest Allis, WI 53227
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9805 W Manitoba St
2 Bedroom Apartments

9805 W Manitoba St

9805 W Manitoba StWest Allis, WI 53227
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WestGlen
1 Bedroom Apartments

WestGlen

1624 S 75th StWest Allis, WI 53214
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1601 S 84th St
1 Bedroom Apartments

1601 S 84th St

1601 S 84th StWest Allis, WI 53214
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2232 S. 96th St.
1 Bedroom Apartments

2232 S. 96th St.

2232 S 96th StWest Allis, WI 53227
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Tara Hill Apartments
1 to 2 Bedroom Apartments

Tara Hill Apartments

3946 S Tara Hill DrGreenfield, WI 53220
  • Utilities Included

Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

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6709-6710 W Barnard Ave
2 Bedroom Apartments

6709-6710 W Barnard Ave

6709-6710 W Barnard AveGreenfield, WI 53220
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10253 W Cleveland Ave
1 Bedroom Apartments

10253 W Cleveland Ave

10253 W Cleveland AveWest Allis, WI 53227
  • Utilities Included

Highwood Estates, Milwaukee, WI Local Guide

Cheapest Available Highwood Estates Apartments for Rent

 

The cheapest available apartment rental in the Highwood Estates area of Milwaukee, WI is a 1 Bed unit found at 5302 W Burnham St. 6 Unit priced from $795. Garden Pool Apartments has the second lowest priced unit, which is a 1 Bed apartment currently listed from $855. Here are the most affordable Highwood Estates apartments for rent in Milwaukee, WI:

Apartment ListingModel NameBed/BathPriced From
5302 W Burnham St. 6 Unit1BR/1.0BA1BR,1BA$795
Garden Pool ApartmentsOne Bedroom1BR,1BA$855
3130 S 48th St. - 8 Family1BR/1.0BA1BR,1BA$875
Forest Arms ApartmentsOne Bedroom1BR,1BA$925
Colonial Manor Apartments1 Bed 1 Bath1BR,1BA$949
St. GregoryWarnimont1BR,1BA$960
3270 S 49th StOne Bed One Bath1BR,1BA$995
Morgan GroveGrafton1BR,1BA$999
Woodland CourtTurquoise1BR,1BA$1,045

Best Value Apartments for Rent in Highwood Estates, WI

As of December 28, 2025 the best value apartment in the Highwood Estates area is the $1.25 price per square foot 2710 S 68th St Model at 2710 S 68th St, Unit 2712 upper in the in the Southwest Side neighborhood starting from $1,500. The second greatest value Highwood Estates apartment is the 2370 S 107th St Model at 2370 S 107th St, Unit Apt. 6 starting at $990 with a $0.99 price per square foot in the Alcott Park neighborhood. Here is today’s list of the best values for Highwood Estates apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
2710 S 68th St, Unit 2712 upper2710 S 68th St3BR,1.5BA$1.25
2370 S 107th St, Unit Apt. 62370 S 107th St1BR,1BA$0.99
4912 W Oklahoma Ave4912 W. Oklahoma Ave. #12BR,1BA$1.23
Toldt Terrace Apartments2bed2BR,1BA$1.25
9531 W Beloit Rd2 BD 1 BA2BR,1BA$1.30
7319 W Tripoli Ave, Unit 27319 W Tripoli Ave2BR,1BA$1.20
3061 S 72nd St, Unit # 33061 S 72nd St2BR,1BA$1.35
Willowick Apartments2 Bed 1 Bath Upper2BR,1BA$1.36
English Meadows Apartment Homes, Greenfield WI1 Bedroom Large - 810 Sq Ft1BR,1BA$1.31
3270 S 49th StOne Bed One Bath1BR,1BA$1.23

Don't Settle: How to Negotiate Your Apartment Lease and Save Money

Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.

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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.

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Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting

Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.

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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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Pet Friendly Lifestyle
Highwood Estates, Milwaukee, WI

Ranked #156

Among cities in Wisconsin for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

4.0
Pet Friendly

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Lifestyle Ratings

ApartmentHomeLiving brings you our detailed rental analysis called 'Lifestyle Ratings' - a comparison of rentals and neighborhoods across the USA, including Milwaukee. LifeStyle Ratings are a useful tool for comparing and sorting apartments and neighborhoods when choosing your rental home. This takes in many factors including rankings of the best places for proximity to parks, luxury amenities, pet-friendly features, places that make kids happy, proximity to transit, in addition to floorplans, availablity, and pricing. Find Lifestyle Search in the filter options (above). Happy Searching!

Frequently Asked Questions about Cheap Highwood Estates Apartments

What is the Cheapest Studio apartment in Highwood Estates?

Currently the most affordable Cheap Studio Apartment in Highwood Estates is at VMP Senior Living Apartments listed at $1,133.

How much is rent for a Cheap One Bedroom Highwood Estates Apartment?

The lowest price for a Cheap One Bedroom Highwood Estates Apartment is $795 at 5302 W Burnham St. 6 Unit.

What is the lowest price for a Cheap Two Bedroom Highwood Estates Apartment for rent?

Today's best deal for a Cheap Two Bedroom Apartment in Highwood Estates is starting from $1,086 at Morgan Grove.

What is the most affordable Highwood Estates Three Bedroom Apartment?

The best deal on a cheap Highwood Estates Three Bedroom Apartment rental is at 8900-8916 W Howard Ave and starts from $1,695.

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.

Articles, How-To's, and Tips

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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.

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How to Make Your Apartment Holiday-Ready: Renter-Friendly Tips

Written by: Justin Habersaat

Getting your apartment ready for the holidays can be exciting but sometimes challenging in a smaller space. Here are some modern tips to keep things festive, safe, and inviting this season.

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Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.

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Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.