Social Media
★★★★★
"Eli and Regan are top class, a force to be reckoned with. They jumped on our project and were incredibly responsive and thoughtful in their approach. Supported us with data and experience, helping us make decisions throughout the selling process. Would happily recommend them to others looking to buy or sell in the Chicago area."
- Angelo R.
★★★★★
"I cannot recommend Second City Agents or Regan enough!! Going through this journey with Regan felt full circle as she was the realtor who helped me find my first rental in the city to finding my first condo in the city. Since day one she was attentive, walked me through the process, & answered every question I asked (even when I asked it multiple times)! Regan goes beyond being a realtor- she’s your biggest advocate & supporter and as a first time buyer that’s all you can ask! Thank you thank you thank you Regan!"
- Gabriella M.
★★★★★
"Fantastic experience working with Second City and Regan! Professional but also felt like you were working with someone who genuinely wanted what was best for you!
"
- Katherine S.
★★★★★
"Regan and Eli were absolutely fantastic to work with for our first home buying experience.
Eli's access - due to be a top real estate agent in Chicago - to exclusive listings and resources were top notch and allowed us to be competitive in today's limited market.
Regan's professionalism and expertise was incredibly impressive and helpful throughout the experience. Her knowledge of building details AND unit features made us feel even more confident that we were investing in a stable, safe property with no hidden surprises post-sale. Every text, call, or question was promptly responded with a thoughtful and educational response which was extremely helpful for us being first-time home buyers.
When we finally found the property of our dreams, Regan was able to negotiate to ensure favorable terms and beat out multiple offers.
In today's competitive real estate market, working with a best-in-class team is essential, and we could not recommend Eli & Regan more! Thank you again, Eli & Regan!!"
- Lexi H.
★★★★★
"Regan helped me as a first time buyer find my dream condo! She is extremely knowledgeable & responsive, and was able to give guidance every step of the way. Regan was an awesome support system through the biggest decision of my life thus far. She had great intuition, an eye for detail, & has a contact for everything (paint, contractors, cleaners). If my next home is in Chicago, I know who to call!/em>"
- Taite P.
Specialties
- Buyer's Agent
- Seller's Agent
- Luxury Homes & Condos
- First-Time Home Buyers
- Relocation to Chicago
- Investment Properties
- Multi-Unit Properties
- Condo Sales
- New Construction
- Personalized Listing Marketing
- Strategic Negotiation
- Pricing Strategy
- Off-Market Opportunities
Education
Regan Grabill is a Chicago real estate broker with Second City Agents, helping buyers, sellers, investors, and those relocating confidently navigate Chicago's ever-changing real estate market. She is known for her personalized approach, strong negotiation skills, creative marketing strategies, and commitment to making every client feel informed and supported throughout the buying or selling process.
Marketing isn't just part of her job—it's her background. Before transitioning into real estate, Regan built a career in marketing, advertising, user experience, and market research after earning degrees in Interactive Media Studies and Entrepreneurship from Miami University (Ohio). Today, she combines that experience with deep market knowledge to give her clients a competitive advantage.
In today's market, getting a home sold takes more than putting it on the MLS. It takes thoughtful pricing, strategic marketing, compelling storytelling, and skilled negotiation. That's where Regan thrives. She creates customized marketing strategies designed to maximize exposure, attract the right buyers, and deliver the strongest possible results.
Since launching her real estate career in 2022, Regan has helped clients buy and sell homes across Chicago—from first homes and luxury condos to investment properties and relocations. She believes every client deserves a strategy tailored to their goals because no two moves are ever the same.
Regan specializes in Chicago's most sought-after neighborhoods, including Fulton Market, West Loop, River North, Gold Coast, Old Town, Lincoln Park, Lakeview, Bucktown, Wicker Park, and West Town. Having lived in several of these neighborhoods herself, she provides firsthand insight into the lifestyle, market trends, and opportunities that help clients make confident decisions.
Above all, Regan believes real estate is about relationships. Her clients appreciate her responsiveness, honesty, attention to detail, and ability to make what can feel like a stressful process both seamless and enjoyable. Whether buying, selling, investing, or relocating, Regan is committed to delivering exceptional service long after closing day.
Outside of real estate, Regan enjoys traveling, playing pickleball, taking classes at Barry's Bootcamp and Ritual Hot Yoga, cooking, and exploring Chicago's incredible restaurant scene with friends and family.
Regan Grabill’s Listings
$2,319,000
- 3
- Bedrooms
- 4
- Bathrooms
- 3,200
- Square Feet
- Unavailable
- Acres
$1,049,000
- Unavailable
- Bedrooms
- Unavailable
- Bathrooms
- Unavailable
- Square Feet
- 0.06
- Acres
Regan Grabill’s Transactions
$5,365,000
3228 W Palmer St
Chicago
$3,277,408
545 N Mcclurg Ct
Chicago
$2,650,000
3049-51 N Spaulding Ave
Chicago
$2,500,000
1444 W Erie St
Chicago
$4,679
202 W Hill St, Unit 1501
Chicago