Rooted in legacy. Driven by purpose. We’re building something bigger than transactions—we’re restoring homes, revitalizing communities, and helping families move forward with confidence.
Olive & Oak Property Group creates honest, human-centered real estate solutions that put people first. As a family-founded company backed by 40+ years of combined experience across real estate, finance, and trust services, we’re committed to delivering clarity, care, and confidence in every interaction.
Whether you’re navigating a life transition, dealing with a time-sensitive sale, or exploring smart investment opportunities, we’re here to guide you with integrity and intention. Our mission is simple: create lasting value for homeowners, investors, and communities across Chicagoland.
Revitalizing overlooked neighborhoods and restoring opportunity.
A legacy of integrity, passed down through generations.
40+ years across real estate, trust, finance, and marketing.
Expanding affordable, accessible housing solutions for local families.
Whether you’re facing a foreclosure, managing an inherited property, or simply ready for a fresh start, Olive & Oak will meet you where you are. We buy homes in any condition, make fair cash offers, and work around your timeline. Most importantly, we walk with you through every step of the process—no pressure, just partnership.
Skip the bidding wars and confusion. Whether you’re buying your first home or growing your portfolio, Olive & Oak makes the process clear and confident. Our homes are thoughtfully renovated, fairly priced, and ready when you are because buying real estate should feel exciting—not overwhelming.
Put your capital to work—while backing real, purpose-driven projects. Olive & Oak offers short-term, secured real estate lending opportunities with competitive returns. Every loan is backed by a mortgage or deed of trust, giving you confidence in every transaction.
Off-market. Below market. First access. At Olive & Oak, our investor partners get early access to rehab-ready and rental-friendly properties—before they hit the MLS. If you’re ready to move fast and think long-term, we’re ready to deliver the deals.
Founder
A visionary leader guided by purpose and integrity, Karen brings a strategic mindset and a belief in doing real estate the right way—for people, for families, and for the future. Her experience in real estate, creative operations, and project leadership allows her to navigate complex transactions with clarity, care, and confidence.
CO-FOUNDER
Driven by service and strategy, Sara combines sharp investment insight with a passion for helping families find peace of mind. With an eye for opportunity and a heart for community, she’s committed to strengthening neighborhoods and supporting buyers and sellers through every step of their journeys.
Not at all. In fact, the sooner we talk, the more options we can explore together. We specialize in helping homeowners avoid foreclosure by offering fast, fair, and respectful solutions. You’re not alone—and you’re not out of time.
No. We don’t charge commissions, listing fees, or hidden costs. When we make you an offer, that’s what you get. Simple, honest, and straightforward.
Most transactions close in as little as 7–14 days, depending on your needs. We work around *your* timeline, not ours. Whether you need to move quickly or need a little more time, we’ll make it work.
You’re not alone—this is more common than you think. We’ve helped families through probate and estate sales with care and guidance every step of the way. Let’s talk through what you’re facing and find a plan that works for you.
Absolutely. Buying a home should feel exciting—not overwhelming. We walk you through the process clearly and compassionately, helping you make confident decisions without pressure or confusion.
No. We don’t charge commissions, listing fees, or hidden costs. When we make you an offer, that’s what you get. Simple, honest, and straightforward.
Yes. We often sell off-market and give our community first access to select listings before they’re publicly advertised. Join our buyers list to get notified early.
Every loan is secured by a mortgage or deed of trust, recorded with the county, and backed by real property. We treat every lender relationship with transparency and professionalism because trust is at the heart of what we do.
No. We don’t charge commissions, listing fees, or hidden costs. When we make you an offer, that’s what you get. Simple, honest, and straightforward.
Yes. We handle the heavy lifting—from acquisition to renovation to resale. Your role is to fund the deal and receive your agreed-upon return. No hammers, no headaches—just a meaningful way to grow your wealth.
Sign up for our Investor Access list. Once we verify fit and interest, we’ll send you vetted, rehab-ready or rental-friendly properties before they go public.
No. We don’t charge commissions, listing fees, or hidden costs. When we make you an offer, that’s what you get. Simple, honest, and straightforward.
Mostly single-family homes, but we also work with small multis and value-add opportunities. We focus on underutilized properties with strong upside in appreciating neighborhoods.
We’re not agents, and we’re not just investors—we’re mission-driven partners. We buy, restore, and sell homes with purpose. Every deal we make is rooted in legacy, community, and compassion—not commissions.
No. We don’t charge commissions, listing fees, or hidden costs. When we make you an offer, that’s what you get. Simple, honest, and straightforward.
Always. No forms. No pressure. Just real people, ready to listen. We’ll walk you through your options and help you figure out what’s best for you—even if that means pointing you in a different direction.
