ABOUT | BUYING | SELLING | IN GOOD HANDS | ACTIVE LISTINGS

The Dobbs Group welcomes you to Wicker Park!

Straddling the trendy bars and boutiques along Milwaukee and North Avenue, find yourself whisked into the world that is the fabulous and bustling Wicker Park. Perhaps you’re searching for your first home, or considering a relocation to this wonderful city, either from the suburbs or out of state and Wicker Park is on your short list of neighborhoods to explore? Or maybe you live in Wicker Park or nearby and want more space? Are you on the selling side and you need a realtor that specializes in Wicker Park to sell your beautiful home? Whatever your real estate needs may be, I am confident we can be your thoughtful and knowledgeable guides in exploring Wicker Park and the many housing styles this wonderful neighborhood offers.

Neighborhood Overview

With just a 10-15 minute commute downtown via the CTA blue line, Wicker Park has emerged as one of the most competitive real estate markets in the city. The residential side streets give off Bohemian, Brooklyn-esque vibes with ‘hipster’ flats, duplexes, loft-style condos, and beautiful modernized single family homes. The charming vibe extends to the retail streets that wrap around the neighborhood, featuring reclaimed warehouse spaces and newly built storefronts showcasing the many restaurants, bars, and boutiques that call Wicker Park home.

The average price for single family homes in the area is around $630K, along with rental housing that average around $2K per month. Wicker Park is considered one of the city’s hotspots for a ‘walker’s paradise,’ with its high walk score and most daily errands can be accomplished on foot, or bicycle via bike-friendly routes. Milwaukee avenue is a major biking stretch, as well as Wicker Park’s easily accessible entrances to the 606 trail.

Our Favorite Places

Located at the intersection of North Avenue, Milwaukee and Damen is the Robey Hotel’s Up Bar, which showcases an amazing view of Chicago’s skyline from their 13th floor rooftop lounge. It’s an excellent backdrop for a photo opp with the skyline as your view! Our favorite drinks on their menu are the flights of mezcal and whiskey from destinations around the world.

The Violet Hour bar is one of the best kept secrets in Wicker Park. As a Chicago aficionado, Debra and her team know their way around the most treasured gems in every Chicagoland neighborhood! Casually strolling down Damen avenue, it’s easy to miss the Violet Hour’s hidden entrance at first glance. Upon entering, take a trip back in time and sip creative cocktails while feeling like Marie Antoinette herself, surrounded by a lush Victorian, prohibition style atmosphere.

Fluevog Shoes is one of our favorite Wicker Park retailers. John Fluevog is a world renowned Canadian shoe designer, inspired by art-deco style features and his shoes are handcrafted to perfection. Fluevog also offers expert shoe restoration and repair services that are second to none. Whether you’re looking for a unique gift or just want to treat yourself, you are in for a treat at Fluevog.

Let’s Talk Wicker Park! Click to chat or call Debra at 312-307-4909

Wicker Park Neighborhood Chicago

How the Dobbs Group can help you buying a home?

Defender of your Interests

Debra is known as a fierce advocate for her clients’ best interests. She will ensure you buy your ideal home at the best price and at terms structured to meet your goals.
Neighborhood Specialist

There are so many amazing neighborhoods and sub-neighborhoods in Chicago that might be just the perfect place for you to live in. Let Debra be your expert guide!
Integrity & Professionalism

Debra is proud to hold the 5-Star Award of Excellence for 10 years running, with top marks from her clients and peers for her professionalism and adherence to highest standards of ethics and integrity.
Deep Knowledge of the Market

Debra’s passion for data means she is an authoritative voice for pricing, market time, neighborhood trends, and school ratings. Debra knows the market and will help you make an informed decision. Check out The Dobbs Report.
Helping Hand

Debra likes to say the real works starts once the offer is submitted and all the way through to the closing. Debra and her team will be at your side, guiding you through the entire process and ensuring your path to closing is smooth.
Legalities

Debra works with a handful of the best residential real estate attorneys to make certain every aspect of the contract review process is managed with your best interests at heart. Your attorney and Debra will get you to the closing table on time and minimizing the friction along the way.
Negotiations

38 years of experience negotiating hundreds of real estate transactions, many of them nail biters, gives Debra THE edge when negotiating on your behalf.
Paperwork and Administration

Debra and her team follow a 168 point checklist from the start to finish of every transaction, making certain no detail is overlooked. Debra and her operations team harness the best of technology while recognizing the importance of a personal touch.
Valuable Contacts

38 years of people, places and services at your disposal! Whether you need a home inspector, mortgage broker, moving co, dog walker, or you are looking for the best place for a French 75, or the latest trend in interior design, Debra is in the know and believes in sharing the wealth of her knowledge. Ask for a copy of Debra’s Little Black Book!
Stay in Touch

Debra strives to create a long-term relationship with each and every client. From her property tax seminar to her client appreciation party to her annual limited edition Limoncello, you want to be on her list! Get informed, have fun and meet people.

How the Dobbs Group can help you sell your home?

Evaluate Your Home

Accurately and effectively pricing your home to create the best market for the property. We will provide a Comparative Market Analysis for your house, highlighting the relevant competition, including listings that are active in the market, recently under contract and recently sold, and taking into account variables such as supply and demand; economic factors; seasonal demand; location; room count and square footage; views; condition of property; and desirability of unique features.
Provide Recommendations

We will provide recommendations to ensure your house or condo sells in a reasonable time frame. This will include thoughtful staging advice, a pre-listing inspection and maintenance plan, and a strategic marketing plan.
Maximize Exposure

We will market the property locally and globally. Compass is locally owned and the #1 brokerage in Chicago and the North Shore. We will market within the network of local brokers and also internationally.
Professional Marketing And IT Departments

Our in-house professional marketing and IT departments produce award-winning work and fresh ideas that distinguish our clients from the competition. Innovative technology and distinctive branding ads create positive and lasting impressions in the marketplace.
Market within the market

Before your home is officially listed, we will market internally to our network of more than 2,000 brokers and their client bases to reach prospects, buyers and referrals, the most efficient transaction environment in the marketplace.
Domain Name

Your listing will receive its own domain name so that interested buyers can pull up photos, video and property information in one easy step. We will also index the domain with top search engines including Google and Bing for improved search engine optimization.
Professional Photography

and video optimized for both print and the web are among the most important marketing tools when selling a house. Our digital marketing strategy raises online visibility.
High Quality Print And Online Marketing

High quality print brochures, print and online advertising, direct mail, unique URL, social media and e-blasts. Adwerx – a sophisticated digital marketing tactic known as retargeting, which puts your property in front of prospective homebuyers as they surf the web.
Most Desirable Property

Positioning your home as the most desirable property at a given price in a given area. Pricing accurately and making sure your home is in optimal showing condition will set it apart from the competition.
Staging The Home

To improve its marketability. Furnishing an empty home allows the home to show like a model home and stand out in a competitive marketplace.
Conduct Negotiations

With professionalism, attention to detail and a loyal representation of your interests conduct. Expect and receive confidentiality, responsiveness, resourcefulness, communication and strength.

In Good Hands

Debra Dobbs

What do you look for in the Top Wicker Park Real Estate Agents? Someone with a vast understanding of Chicago neighborhoods? How about an invaluable partner and fierce advocate? You should never settle for anyone who isn’t always striving to exceed your expectations!

What people are saying about working with Debra?

  • “Debra is an absolute joy to work with; she makes a process that can be overwhelming and frustrating relatively painless…when it came time for us to negotiate it was clear that Debra was our advocate. Debra has a strong intuition and is a great reader of people.” HOLLY WISNIEWSKI HAWES
  • “I can’t recommend Debra Dobbs enough for a buyer who needs a trustworthy, knowledgeable and professional real estate agent. She is more than an agent – she’s a well-respected consultant in her field and one of the best I have ever worked with.” KATIE SHANNON
  • “I have always found Debra to be professional, fair and sensitive to the needs of her clients. She puts her clients’ interests and needs first and foremost.” ELISSA SCRAFANO
  • “We never felt rushed to make a decision as Debra would routinely say: ‘I want you to get the property that’s right for you, and I’ll show you as many properties as it takes until you do’.” MITCH WALSH
  • “Debra was professional, knowledgeable and fought for us to get the deal closed when issues arose. Great job, Debra!” MICHAEL FEINGLASS

Homes For Sale in Wicker Park

The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Chicago, IL. All properties are subject to prior sale, changes, or withdrawal.
This site was last updated Mar-03-2025 7:25:23 am.
Rover IDX