Your Central Florida
Real Estate Expert
at Keller Williams.
Buying, selling, or investing in the Orlando area? Stacy Ann Stephens brings 24+ years of deep local knowledge and real estate expertise — right here at Keller Williams Realty Winter Park.
Expert Real Estate Guidance
in the Orlando Area
With over 24 years in real estate across Connecticut and Florida, Stacy Ann Stephens has built a practice rooted in honesty, advocacy, and genuine results. As a REALTOR® with Keller Williams Realty Winter Park, she brings market-deep knowledge and a client-first approach to every transaction.
Whether you’re buying your first home, selling to upgrade, or building a real estate portfolio — Stacy is the kind of agent who answers the phone, knows the neighborhoods, and never makes you feel like a file number.
- Deep expertise across 15+ Central Florida communities
- Investor-friendly — DSCR strategies, cash-flow analysis, STR markets
- ITIN & foreign national buyer specialist — international clients welcome
- Former IRS Enrolled Agent — unmatched financial literacy for complex transactions
- MBA in Project Management — your transaction stays on time and on track
Full-Service Real Estate
Across Central Florida
From first showing to closing day — and every step of the process in between.
Buy a Home
Find the right home in the right neighborhood — with guidance you can trust from someone who actually knows Central Florida. First-timers, families, and relocators all welcome.
Search Listings
Sell Your Home
Strategic pricing, professional marketing, and expert negotiation — backed by KW’s global network. We get your home sold for what it’s worth, on your timeline.
Get a Free Valuation
Invest in Real Estate
Long-term rentals, short-term rental markets, or portfolio growth — Stacy understands the numbers investors need to see, and the Central Florida markets where they pencil out.
Investor ResourcesBrowse Homes for Sale in Central Florida
Every Buyer Deserves
an Expert in Their Corner
Stacy built her practice for the clients who need more than a lockbox and a contract. If you have questions, she has answers.
First-Time Buyers
Not sure where to start? That’s exactly where Stacy comes in. She walks first-timers through every step — neighborhood selection, offer strategy, and closing — without the overwhelm.
Start Your Search →ITIN Holders
You don’t need a Social Security number to own property in Florida. Stacy has deep experience working with ITIN buyers and connecting them with the right financing resources.
Learn More →Foreign Nationals
International buyers choose Central Florida for vacation homes, investment properties, and permanent relocation. Stacy navigates cross-border transactions and compliance with care.
International Buyers →Real Estate Investors
Cash flow analysis, STR market intelligence, DSCR financing resources — Stacy brings the investor-friendly knowledge most residential agents simply don’t have.
Investor Resources →Sellers & Upsizers
Ready to move up? Stacy’s market knowledge helps sellers price strategically, time their listing, and negotiate from strength — especially in competitive Central Florida submarkets.
Selling Your Home →Corporate Relocators
Moving to Central Florida for work? Stacy helps corporate transferees find the right community fast — with neighborhood guides, school data, and commute intelligence built in.
Relocation Guide →
I Built This Practice
for the Clients
Who Needed It Most.
“I came to this country from Jamaica. I know what it feels like to need someone who will actually take the time to explain, advocate, and fight for you.”
Stacy Ann Stephens has been in real estate for over 24 years — but she didn’t build her practice for the easy clients. She built it for the ITIN holder told they couldn’t own property. For the relocating family overwhelmed by a new market. For the investor who needed an agent who could actually read the numbers.
As a REALTOR® with Keller Williams Realty Winter Park, she brings the full power of the KW network — and 24 years of hard-won expertise — to every transaction she touches.
What Clients Say
About Working with Stacy
Stacy knew Winter Park inside and out. She helped us narrow down neighborhoods in days, not months — and her negotiation got us $18K under asking. We couldn’t have done it without her.
As a Venezuelan national, I didn’t know if I could even buy property in the U.S. Stacy walked me through every step — legal, financial, practical — and I closed on my Orlando home in 45 days.
I’ve bought investment properties with three different agents over the years. Stacy is the only one who actually understood the numbers — cap rate, cash flow, STR potential. She’s the real deal.
Answers to the Questions
Clients Ask First
Central Florida Real
Estate Insights
Ready to Buy, Sell,
or Start Exploring?
No pressure, no obligation. Just a real conversation with a REALTOR® who knows Central Florida and will tell you the truth about the market — whether it’s what you want to hear or not.
147 W Lyman Ave, Winter Park FL 32789