About The Bailey Team
Family-owned real estate since 1970. Northern Virginia since 1988. Three generations of brokers serving Virginia, Washington D.C., Maryland, and West Virginia — with more than 7,500 closed transactions and a single way of working: personally, transparently, and with a long view.
Our Story
The Bailey Team has been a family real estate practice since 1970, and we've called Northern Virginia home since 1988. Across three generations of brokers, what's stayed constant is the way we operate — relationship-first, never transaction-first. We build careers around clients who stay with us for life, who introduce us to their kids and their parents, who call us before they call anyone else when a family member needs to move.
Today the team is led by Gayle T. Bailey II, who carries the family practice forward alongside her partner Jenna. Gayle and Jenna are high school sweethearts who built their lives together in Virginia Run, Centreville, where they're raising their two boys. Gayle brings the family real estate legacy, the regional broker relationships, and the deep commercial bench through KW Commercial; Jenna brings the marketing instincts and the attention to detail that make every transaction feel intentional. The two of them have anchored the next generation of the family business, and most of our new business still comes from referrals.
What We Do
The Bailey Team is unusual in that we offer five distinct real estate disciplines under one roof — most teams specialize in one. Our cross-disciplinary breadth means a single relationship can carry a client through residential moves, commercial purchases, ALF transitions for aging family members, and business sales — all without handing them off to another team.
- Residential — the heart of what we do, with deep coverage across the DC Metro, NoVA, and outer counties
- Commercial — through KW Commercial, with Gayle T. Bailey II as Senior Director. Office, retail, industrial, multifamily, land, and special-purpose properties across the four-state region
- Assisted Living Facility brokerage — as the official regional representative for My ALF Consultant in VA, DC, MD, and WV
- Business brokerage — for owners selling small to mid-market businesses where real estate is part of the deal
- Rentals and rental-portfolio sales — the often-overlooked piece of a full-service practice, and a long-standing strength
Where We Work
The Bailey Team is fully licensed in Virginia, Maryland, Washington D.C., and West Virginia. Our primary marketing footprint is Northern Virginia — but for commercial transactions and Assisted Living Facility listings, we travel anywhere in our four-state region. Virginia Beach, Roanoke, Morgantown, Ocean City, the Eastern Shore. If the deal warrants the travel, we're there.
What Makes Us Different
Three generations of family ownership. Most NoVA real estate teams are 5-10 years old. We've been in real estate since 1970 — which translates to deeper relationships, more reliable comparables, and a broker reputation that opens doors on confidential transactions.
Cross-disciplinary bench. Most teams do residential and nothing else. We bring residential, commercial, ALF, business brokerage, and rental disciplines to every client — which matters when a commercial deal also involves an executive's home sale, or when a senior downsize involves both a family home and an ALF transition.
Reston-based, regionally licensed. Keller Williams Realty out of Reston anchors our residential practice. KW Commercial extends our commercial reach. Multi-state licensure means we follow our clients wherever their lives take them.
We live where we work. Gayle and Jenna live in Centreville. We don't farm neighborhoods we don't know — we work the communities we're part of.
Brokerage
The Bailey Team operates under Keller Williams Realty, with our primary office at 11710 Plaza America Dr Ste 710, Reston, VA 20190. Our commercial practice operates through KW Commercial, where Gayle T. Bailey II serves as Senior Director. Additional offices in Winchester, Ashburn, Fairfax, and Richmond extend our reach across the region.
Contact
Call: (571) 240-4495
Email: Gayle@GayleBailey.com
Licensed in: VA, MD, DC, WV
License #: 0225189171
Areas We Serve
The Bailey Team has been serving Northern Virginia and the wider DC region since 1988 — a third-generation, family-owned real estate team licensed in Virginia, Maryland, DC, and West Virginia. Below are the markets where we operate most often, but our footprint runs further than this list.
And Everywhere Else
The list above is where we work most often, but we're licensed across all of Virginia, Maryland, DC, and West Virginia and we serve clients statewide in each. Explore the full DMV — Fredericksburg, Spotsylvania, Culpeper, Madison, Rappahannock, Frederick County VA, Winchester, Clarke, Warren, Manassas, Manassas Park, Prince George's County MD, Charles County MD, Calvert County MD, Frederick County MD, Jefferson County WV, and Washington DC — via the sidebar on any page.
For commercial transactions and Assisted Living Facility listings, we travel anywhere in our four-state region — Virginia Beach, Roanoke, Morgantown, Ocean City, the Eastern Shore. If the deal makes sense and you want a team that already understands the regulatory landscape and broker community, call us.
