“She was great to work with. Professional, personable, responsive, and reliable. I highly recommend working with her.”
Realty of America
- Agent Pronto
- Wisconsin
- Milwaukee
- Highwood Estates
The best way to find top real estate agents in Highwood Estates, Milwaukee, WI
We analyze thousands of real estate agents in Milwaukee’s Highwood Estates neighborhood and nationwide to find you proven local professionals, for free.
- Client Testimonials and Reviews
- Local Market Reports
- Tailored Agent Recommendations
- Free Home Value Estimates
- Agent Sales Histories
- 100% Free, No Obligation
Compare top Highwood Estates real estate agents.
Agent Pronto analyzes transaction data, agent specialties, and client reviews to handpick the best agents in your area. Updated for October 2026.*
* Sales data is calculated based on transaction information available to Agent Pronto at the time of publishing and may not accurately reflect all transactions for a given agent.
The easiest way to find a top agent you can trust.
Sell faster. Buy smarter. Get matched with proven agents who know your market—all for free.
- Tell us what you need.
- Answer a few quick questions about your real estate goals.
- Get matched.
- We’ll find you top local agents based on performance, expertise, and customer reviews.
- Connect and compare.
- Review your personalized recommendations and choose who’s right for you.
- Move forward with confidence.
- Whether you’re buying, selling, or both, you’ll have a proven expert on your side.
Highwood Estates real estate Market Report.
Information and statistics on the latest trends in the Highwood Estates real estate market. *
Latest Rolling 3-Month Snapshot
Jul 1, 2026 - Sep 30, 2026
Median sale price
$302K
-12%
from Q2 '26
Median list price
$296K
-8.9%
from Q2 '26
Active listings
10
No change
from Q2 '26
Homes sold
5
-38%
from Q2 '26
New pendings
8
+33%
from Q2 '26
New listings
7
-13%
from Q2 '26
Quarterly Pricing Trends for Highwood Estates
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Highwood Estates
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Pricing Trends for Highwood Estates
Rolling three-month data ending on quarter boundaries when available.
Median sale price
Median list price
Quarterly Inventory and Sales Activity for Highwood Estates
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Highwood Estates
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
Quarterly Inventory and Sales Activity for Highwood Estates
Rolling three-month supply and activity totals for the selected period.
Active listings
Homes sold
New pendings
New listings
13
Seller’s Market
Seller’s Market
Buyer’s Market
0
20
40
60
80
100
0
25
50
75
100
Market gauge is calculated using active listings and pending sales from the most recently available reporting period (Jul 2026 - Sep 2026).
Year-over-year, Highwood Estates home values have dipped slightly, with the typical home value down a bit even as the median list price has edged up. Compared with the wider Milwaukee market, prices in the neighborhood remain higher overall, even as local values softened while the city’s typical sale price rose over the past year.
In the latest rolling three-month view through September 2026, supply has tightened compared with last year, with active listings down sharply and homes sold also declining. Months of supply has risen to 1.9 and is still below Milwaukee’s 2.9 months, reinforcing that conditions lean toward sellers despite slower sales.
Demand signals are strong in this period, with nearly four out of five homes selling above list price and the average sale-to-list ratio above 106 percent. Even with median days on market stretching to 43, a majority of homes go off the market within two weeks, so both buyers and sellers can benefit from an Agent Pronto–recommended real estate agent to navigate this fast-moving environment.
Learn more about what Highwood Estates has to offer.
Highwood Estates offers residents a welcoming, family-friendly community with well-kept homes, tree-lined streets, easy access to parks and local amenities, and a strong sense of neighborly pride.
Highwood Estates in Milwaukee offers a practical balance of quiet residential streets and everyday convenience, appealing to both long‑time residents and newcomers. Tucked on the northwest side of the city, the neighborhood provides mostly single‑family homes with yards, access to local schools, and a straightforward commute via nearby routes into Milwaukee and surrounding job centers.
Daily needs are close at hand, with shopping clusters along Appleton Avenue and frequent bus connections through the Milwaukee County transit network. Outdoor time is easy to plan. Residents can head a short distance to Dineen Park for fishing, playgrounds, and sports fields or enjoy the larger trail system and recreation facilities at Kern Park along the Milwaukee River. Families also appreciate access to nearby schools such as Rufus King International High School and community resources like the Milwaukee Public Library system.
Dining options range from neighborhood diners to global cuisine in adjacent areas such as Washington Heights and Riverwest, while entertainment and cultural venues downtown are a manageable drive. For those who prioritize practical livability, Highwood Estates offers a stable, accessible base with city amenities close by.
Choosing an agent who understands Highwood Estates and the broader Milwaukee market can make every step smoother. Agent Pronto connects buyers and sellers with local real estate professionals who know the streets, pricing trends, and nuances of this neighborhood, helping reduce stress from the first conversation through closing.
Trusted by over 500,000 buyers and sellers.
See why so many people rely on Agent Pronto to make their real estate journey a success.
“We were looking to move, and had a referral for Krag. We couldn't be more pleased. Krag made the entire process of buying and selling our homes stress free. He is very personable, quick to respond, and answered any and all questions/concerns we had. It was an excellent experience. We definitely recommend Krag, and wouldn't hesitate to have him as our agent again.”
RE/MAX Affiliates
“Renee is an incredibly knowledgeable agent that has a lot of experience, cares about her clients, and is trustworthy !! She knows the ins and outs of current real estate markets and how to strategically price a property so that it will sell in a timely manner but with the highest yield!! She has sold two of our properties over the last eight years (one in Illinois and one in Wisconsin) and we received more than we expected on each of the sales!! We cannot recommend her highly enough! Thank you so much, Renee!!”
Keller Williams North Shore West
“Jim was brought into our search by my daughter who knows him. He was very helpful even though we weren't sure what we were looking to do. He was always available for chats when we needed him and had a sense of humor when we thought we were being a pain! Appreciate everything he did for us in the process of buying our home.”
Century 21 Ace Realty
“Levi fully understood our needs. He was always honest and direct. He told us what our house should list at and sold it very close to our asking price. We would highly recommend Levi to family and friends looking to buy or sell a home!”
RE/MAX Port Cities
“Kyle did a wonderful job for my family. My first time selling a home and he answered every question I threw at him with no hesitation. I never give anyone a 10 because they can always be perfect. I would definitely reach out to Klye again when I sell my home in the future.”
Forward Realty Partners
“Libby was so patient with me through the whole process. I changed locations and type of house I was looking amongst other things. It never seemed to bother her. She was very honest with me through every house we looked through. I could really tell she cared about me finding a house that felt right for me. She helped me get to the bottom of a question I had about the house I finally did purchase over a year later. I would highly recommend Libby to anyone looking to buy a home! She made me feel very taken care of and supported through the whole process.”
Berkshire Hathaway Bay Area Realty
“We worked with Matt and Candie on real estate transactions in Cape Coral, FL, Ft. Myers, FL and Madison, WI. With all 4 transactions, their knowledge of the market and neighborhoods was excellent. They have great negotiation skills when it came to purchasing and selling our homes. They were also very helpful in all the aspects of selling and buying a new home. Whether you needed help finding a service provider to get something repaired, coordinating with getting utilities switched over, or getting your modem out of the home before closing, Matt & Candie were always there. They are really great partners to have when selling or buying your home!”
Century 21 Selling Paradise
“Braylee was amazing with all the time and effort she put in to help us every step of the way!”
Resource One Realty
“Brian did a great job on helping us to find the right condo. We started our search without not really knowing what we were looking for. Brian helped us figure it out. I looked at a lot of properties, until we narrowed it down to 4 And we found what we were looking for. Thanks Brian!”
Coldwell Banker Realty
“Erika was great to work with and had a lot of good contacts to make the home buying process easy and efficient. I woukd definitely recommend her to people buying a house!”
Erika Braatz Exp Realty
“I felt immediately comfortable having Bob as my realtor. He explained everything clearly, discussed the plan for selling my property&never made me feel the sale of my property wasn't as important to him as it was to me. I highly recommend Bob for anyone looking for a dedicated realtor. He's dedicated, knowledgeable, calm&never once did I feel he wasn't motivated to sell my property. I was completely comfortable with Bob. If you're looking for someone who has your best interests in mind,hire Bob.”
Homestead Realty Inc.
“We strongly recommend Larry Nielson for selling/buying your next home. He was very knowledgeable, confident and easy to work with.”
Nielson Real Estate Services
“Jen Burns is extremely good realtor I was an out of state buyer and her help was greatly appreciated negotiating with the builders and making sure the house was done to my specifications. I greatly appreciated her help for the last 9 months to keep it on track. Thank you again Jen Burns I really appreciate. Jen also found me a realtor for my home in St. Louis Missouri Jen is very professional and experienced in her profession. Thank you again. Mark Ruess”
Century 21 Affiliated
“My experience with Mo Simmons was one of respect support and professionalism for my decision to sell my home of 41 years. From the first prompt contact until closing Mo has been available in all phases in the process with any suggestions or recommendations I was always aware of my options before making my decisions. It has been my pleasure to work with her.”
Synergy Real Estate Group
“They were very prompt. Within minutes of completing the AgentPronto form, I received a call. On a Saturday! Everyone was so nice, and they kept checking in to make sure the realtor was good and if I had questions. An overall good experience.”
Trimberger Realty
“The team was efficient, thoughtful, disciplined and committed. The access to immediate contractor support was also helpful.”
RE/MAX Advantage Plus
“Alyssa was very professional and accommodating. Definitely recommend her.”
eXp Realty
“Amy was very helpful and knowledgeable. Everything went well.”
Keller Williams Premier Realty
“Adam Adler is an excellent agent. We couldn't be more pleased.”
Coldwell Banker The Real Estate Group
Frequently Asked Questions
-
There are more than 2 million real estate agents across the U.S., and you want to be sure the one you partner with is an experienced and trustworthy professional with strong local expertise covering the housing market in and around Highwood Estates. Working with a proven agent will help you sell your home faster and for more money, and help you find your dream home at the best possible price.
-
Choosing a real estate agent to help you buy or sell property is one of the most important decisions you’ll make in your lifetime. You want to make sure your agent is an expert in your area, has a proven record helping people buy and sell similar homes to yours, and is well regarded by their previous clients. Let us know a few details about the property you are selling or the kind of home you want to buy, and Agent Pronto will match you with trusted real estate agents that have the experience you need. And before you interview an agent, check out our top five questions to ask a buyer’s agent and listing agent.
-
We consider performance metrics, close rates, specialties, and client reviews to qualify the best full-time agents. We then take the information you provide about the home you are selling or the kind of home you want to buy, and analyze the top local agents with the right experience for your specific needs. For more than a decade, we've helped hundreds of thousands of home buyers and sellers find the right agent. Get started now and find the perfect real estate agent.
-
No. Agent Pronto is a free service for home buyers and sellers and you are under no obligation to work with our recommended agents. Find your Highwood Estates Realtor® or real estate agent today.
Looking for an agent in a different Milwaukee neighborhood?
We’ll match you with top-rated real estate agents in just about any city—wherever your next move takes you.