Amanda Stapleton
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About Amanda

Amanda Stapleton smiles in a white outfit, seated beside a large palm plant.

Amanda Stapleton

Chicago Real Estate Advisor | Investor | Entrepreneur | Certified Negotiation Expert | Mentor | Philanthropist

Amanda Stapleton is a Chicago-based real estate professional, investor, entrepreneur, mentor, and philanthropist with more than 12 years of experience representing buyers, sellers, investors, and developers throughout Chicago and surrounding Illinois markets.

As a top-producing agent who has closed millions of dollars in real estate sales, Amanda has built a respected brand centered on integrity, discretion, strategic representation, and an elevated client experience. Her business has expanded beyond the local market, allowing her to serve a growing network of international clients seeking real estate opportunities and trusted representation in Chicago.

Amanda specializes in luxury residential real estate, new construction, development, and investment properties. As a real estate investor with her own portfolio, she understands real estate from both sides of the table and brings an ownership and wealth-building perspective to every transaction.

As a Certified Negotiation Expert, Amanda brings advanced negotiation strategy to her representation, advocating for her clients’ interests while navigating complen This version positions you more strongly for the luxury/international market while still allowing people to connect with Amanda the mother, mentor, investor, philanthropist, and entrepreneur not only Amanda the Realtor.

Beyond real estate, Amanda is passionate about philanthropy, youth development, and teen mentorship. She believes exposure, education, confidence, and access to positive role models can change the trajectory of a young person’s life. Giving back and creating opportunities for the next generation remain an important part of her personal mission.

After more than a decade in the industry, Amanda has also expanded her platform to educate real estate professionals. Through The AS Academy, she teaches agents how to develop their brands, create sustainable systems, increase their income, and evolve from simply working as an agent to thinking and operating like a CEO.

As a mother, entrepreneur, investor, mentor, and avid traveler, Amanda believes success extends far beyond professional accomplishments. Her life and brand represent a commitment to ownership, financial freedom, meaningful experiences, community impact, and building a legacy.

For Amanda, real estate isn’t simply about buying and selling property. It’s about creating opportunities, building wealth, protecting her clients’ interests, and leaving an impact that extends far beyond the closing table.

Real Estate. Wealth. Impact. Lifestyle. Legacy.

Contact Details

Email address [email protected]
Primary phone (773) 305-6528
Address 58 E 26th St Chicago IL, 60616
License #475.165609
Chicago Agent Magazine
PropertySpark
Chicago Association of REALTORS

112+

Closed Sales

$33.5M+

Total Value

$650K

Average Price

$200K - $1.5M

Price Range

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Featured Properties

  • Two-story white-sided house with a driveway, front lawn, and mature trees. For Sale

    $795,000

    1950 Monroe Avenue, Glenview, IL 60025

    • 6 Beds
    • 4 Baths
    • 2,500 Sq.Ft.
  • Two-story stone home with a wooden porch, bay windows, and a flower-filled fenced garden. Pending

    $425,000

    5140 S Union Avenue, Chicago, IL 60609

    • 6 Beds
    • 2 Baths
  • Gray multi-story house with a steep front gable, white-trimmed windows, and fenced driveway. For Sale

    $394,000

    5043 S Racine Avenue, Chicago, IL 60609

    • 7 Beds
    • 3 Baths
  • Two-story gray house with steep gables, a covered porch, and fenced yard at dusk. For Sale

    $378,000

    6621 S Green Street, Chicago, IL 60621

    • 6 Beds
    • 2 Baths
  • Blue two-story house with warmly lit bay windows, a raised wooden porch, and a fenced front yard. Active Under Contract

    $320,000

    4203 W MAYPOLE Avenue, Chicago, IL 60624

    • 6 Beds
    • 2 Baths
  • Two-story blue-gray house with a lit entry and fenced front steps at dusk. Active Under Contract

    $315,000

    1117 W 57th Street, Chicago, IL 60621

    • 4 Beds
    • 2 Baths
  • Detached double garage between brick buildings, with a snow-covered driveway and leafless tree. For Lease

    $2,700/mo

    6444 S Eberhart Avenue, Chicago, IL 60637

    • 5 Beds
    • 3 Baths
    • 2,000 Sq.Ft.
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See Why My Clients Love Me

Testimonials

I recently purchased my first multi-unit building with Amanda’s Stapleton. I worked very closely with Eunique who is a broker for the Amanda Stapleton Real Estate team. I love how I was able to ask both ladies and guests without any hesitation. They were honest, reliable, and patient with me. They listened to what I wanted, encouraged me to stick to my plans, and helped me find an amazing building. I am more than happy with my experience with the company and will be sending their information to any and everyone I know. Thank you ladies!
I recently purchased my first multi-unit building with Amanda’s Stapleton. I worked very closely with Eunique who is a broker for the Amanda Stapleton Real Estate team. I love how I was able to ask both ladies and guests without any hesitation. They were honest, reliable, and patient with me. They listened to what I wanted, encouraged me to stick to my plans, and helped me find an amazing building. I am more than happy with my experience with the company and will be sending their information to any and everyone I know. Thank you ladies!
Keya G.
Mrs Amanda helped me find the best investment property for me and my family. I have been a client since 2013 and she has helped me transition from a renter to a homeowner in a matter of months. Every obstacle I faced she defeated. I was able to close with a low down payment and also walk away with over 50k in equity. Thanks so much for your outstanding professionalism and great negotiating skills. I can’t wait for our future deals.
Mrs Amanda helped me find the best investment property for me and my family. I have been a client since 2013 and she has helped me transition from a renter to a homeowner in a matter of months. Every obstacle I faced she defeated. I was able to close with a low down payment and also walk away with over 50k in equity. Thanks so much for your outstanding professionalism and great negotiating skills. I can’t wait for our future deals.
Tatiana
Amanda was very helpful with the home-buying process. She was very informative and helped me put a great team together from the inspector to the lawyer, she made the process easy. She listened to what I wanted in a home and she delivered. She made the process enjoyable. She is definitely proof that if you love what you do you will work hard at it. You can’t go wrong with her as your realtor. She is definitely a real estate rock star.
Amanda was very helpful with the home-buying process. She was very informative and helped me put a great team together from the inspector to the lawyer, she made the process easy. She listened to what I wanted in a home and she delivered. She made the process enjoyable. She is definitely proof that if you love what you do you will work hard at it. You can’t go wrong with her as your realtor. She is definitely a real estate rock star.
Raven H.

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