Serving Key West as a hands-on, boutique brokerage, the Brenda Donnelly Real Estate team brings deep market knowledge and genuine local perspective to every client experience.
Founded by Brenda Donnelly, the firm has more than two decades of experience in one of the country’s most unique markets — where inventory is limited and preservation matters. Many buyers seek more than just a home. They’re investing in a lifestyle. At Brenda Donnelly Real Estate, we are known for understanding those nuances and guiding clients through the process with clarity, confidence, and care.
As a boutique firm by design, we represent buyers and sellers of exceptional homes throughout the island — from historic residences to waterfront retreats and investment properties. Our clients work closely with senior leadership and a dedicated team from start to finish. Every listing is thoughtfully positioned, every strategy is tailored, and every client relationship is valued as a top priority.
We regularly work with buyers relocating to the island, second-home owners, and sellers who value trusted, on-the-ground representation. In testimonial after testimonial, clients value our firm’s approachable style, strong communication, and deep-rooted connection to the community.
At its heart, Brenda Donnelly Real Estate reflects the way Brenda herself works: knowledgeable but welcoming, experienced yet personable, and deeply committed to helping clients feel at home in Key West — whether they’re arriving for the first time or moving on to their next chapter.
Starts Here
No one knows Key West real estate quite like Brenda Donnelly. The award-winning multi-million dollar top producer is a distinguished luxury real estate broker and owner of Historic Key West Vacation Rentals based in the Southernmost city of Key West, Florida. With an unwavering passion for the island's unique charm and a deep understanding of the luxury market, as well as a vast knowledge of all types of investment properties, Brenda is a trusted advisor to clients seeking exceptional opportunities in paradise.
With a wealth of experience in the industry, Brenda has built an impressive reputation for her professionalism, integrity, and personalized service. She possesses an extensive knowledge of Key West’s diverse neighborhoods and the finest properties available, allowing her to expertly match discerning buyers with their dream homes.
In addition to her real estate prowess, Brenda is deeply rooted in the local community. Her passion for Key West’s rich history, culture, and natural beauty makes her an invaluable resource for newcomers and long-time residents alike. She goes above and beyond to connect her clients with the best that Key West has to offer, often sharing insider knowledge on the area’s hidden gems.
Whether you’re seeking a luxurious waterfront estate, a charming historic home, or a stunning vacation/investment property, Brenda Donnelly is the go-to expert who will help you navigate Key West’s luxury real estate market with confidence and ease.
Callie Harris serves as Senior Real Estate Agent with The Donnelly Advisory Group, working closely alongside Brenda Donnelly in the representation of luxury properties throughout Old Town and the Lower Florida Keys. Her practice is distinguished by a deep understanding of waterfront ownership, coastal environments, and the lifestyle considerations unique to island living.
A full-time resident of the Keys since 2005, Callie brings firsthand knowledge of neighborhood character, boating access, marine conditions, and the regulatory nuances that influence waterfront real estate. She is particularly valued by clients seeking guidance on coastal homes, live-aboard suitability, dockage considerations, and environmentally sensitive properties.
Prior to her career in real estate, Callie spent more than 15 years in marine science education and conservation, working with respected organizations including The Turtle Hospital, Reef Relief, and MOTE Marine Laboratory. She holds a degree in wildlife studies and a U.S. Coast Guard 100-Ton Captain’s License — credentials that provide clients with rare, practical insight into the maritime aspects of property ownership in the Keys.
Callie’s approach is calm, analytical, and detail driven. She is known for helping clients understand not only the property itself, but the broader coastal environment, regulatory framework, and lifestyle alignment that inform long-term value and enjoyment.
Working in partnership with Brenda, Callie provides highly personalized, informed experience for buyers and sellers seeking exceptional representation in Old Town and the waterfront communities of Key West.
Lauren Hodges is the operational backbone of Brenda Donnelly Real Estate and the connective force behind the firm’s daily excellence. As Office Coordinator, she ensures that every transaction, communication, and client interaction is executed with precision, professionalism, and care.
Lauren oversees internal operations, transaction management, scheduling, documentation, and team coordination. Her attention to detail and anticipatory problem-solving creates a seamless experience for both clients and agents.
Known internally as the glue that holds the team together, Lauren plays a critical role in maintaining the firm’s boutique service model while upholding institutional-level standards.
Together, Brenda, Callie, and Lauren operate as The Donnelly Advisory Group — a coordinated real estate practice delivering strategic guidance, waterfront expertise, and seamless operational support at every stage of the real estate process. By integrating market authority, environmental insight, and meticulous transaction management, they provide clients with a discreet, highly personalized experience.
This collaborative structure ensures continuity, responsiveness, and careful attention to detail — hallmarks of luxury representation in Key West.
Michelle Howerton is a Senior Real Estate Agent with The Howerton Group, bringing more than two decades of residential real estate experience, including extensive work throughout the Florida Keys. Within the team, she helps guide listing strategy, presentation standards, and transaction management with a disciplined, detail-driven approach.
Michelle is particularly valued where presentation, pricing, and negotiation intersect. Her background enables sellers to position their homes effectively in a competitive market, while buyers benefit from her careful analysis and structured guidance throughout the process.
She holds a bachelor’s degree in interior design and is a Graduate Realtor Institute (GRI) designee. Michelle is also the founder of Somewhere South Staging, providing professional staging services that enhance visual appeal, support strategic pricing, and strengthen market positioning.
Clients rely on Michelle for her contract expertise, organization, and consistent communication from listing preparation through closing. Her steady oversight and strategic insight help ensure each transaction progresses with clarity, confidence, and attention to detail.
Wil Howerton provides clients with specialized insight into construction, infrastructure, and regulatory considerations unique to property ownership in the Florida Keys. As a licensed Realtor®, he contributes to representation with both transactional knowledge and technical expertise.
With more than two decades of experience in the building trades, Wil offers extensive knowledge of Monroe County zoning, permitting processes, and construction practices. A master electrician and former generator company owner, he brings practical expertise regarding electrical systems, resiliency planning, structural considerations, and the mechanical infrastructure essential to island properties.
Wil’s background supports informed decision-making for buyers and sellers evaluating renovations, insurance requirements, storm-hardening measures, and long-term property feasibility. His guidance is particularly valuable during due diligence, helping clients understand compliance requirements, system integrity, and potential costs before closing.
Wil provides a technical perspective that strengthens client confidence and helps safeguard long-term property value in one of the country’s most environmentally and structurally complex coastal markets.
Samantha Bowman supports residential buyers and sellers throughout the Florida Keys with a focus on organization, communication, and follow-through. Working within The Howerton Group, she ensures a seamless experience for clients by coordinating details and maintaining continuity across each transaction
Together, Michelle, Wil, and Samantha operate as The Howerton Group, a family-led real estate practice grounded in trust, continuity, and shared commitment to client care. Their combined strengths — strategic presentation and negotiation, construction and infrastructure insight, and attentive transaction coordination — provide clients with well-rounded guidance at every stage of the process.
This integrated approach ensures clarity, responsiveness, and practical expertise, supporting informed decisions and a seamless real estate experience throughout the Florida Keys.
Megan McDowell transitioned into real estate in 2018 after a successful career in marketing. She represents residential and commercial clients throughout the Florida Keys, integrating strategic marketing expertise with attentive, hands-on client service.
Megan is actively involved in the community, serving on the Board of Directors for the Key West Rotary Club and the Anne McKee Artists Fund, and previously serving with the Key West Association of Realtors and Friends of the Key West Library.
Her background in marketing informs a thoughtful and results-driven approach to positioning properties and guiding clients through each stage of the transaction process. Clients appreciate her responsiveness, clear communication, and ability to navigate both lifestyle and investment considerations in a dynamic island market.
As part of Brenda Donnelly Real Estate, Megan values contributing to a boutique brokerage known for discretion, collaboration, and elevated standards of representation. This environment allows her to provide a highly personalized experience grounded in professionalism, strategic insight, and enduring client relationships.
Allison Findlay serves with Brenda Donnelly Real Estate, bringing deep market knowledge and a calm, strategic approach to representing buyers, sellers, and investors throughout Key West. A full-time resident for more than 17 years, she offers valuable local insight and a nuanced understanding of the island’s neighborhoods, architectural character, and lifestyle appeal.
Allison’s practice includes exclusive seller representation, strategic listing preparation, and personalized guidance for buyers seeking property in Old Town, Casa Marina, and the greater Key West area. Clients value her ability to evaluate opportunities, anticipate challenges, and position properties effectively within a sophisticated and highly competitive market.
With a professional background in hospitality and elevated client service, Allison is known for her responsiveness, transparency, and composed, solutions-oriented style. She believes trust, clarity, and advocacy are essential to meaningful client relationships — many of which continue long after closing, as clients rely on her for local insight, trusted vendor connections, and long-term property stewardship.
As part of Brenda Donnelly Real Estate, Allison values contributing to a boutique brokerage defined by discretion, collaboration, and elevated standards of representation. This structure allows her to deliver a refined, highly personalized experience grounded in professionalism and enduring client relationships.
Nika Stroble leads visual strategy and digital storytelling for Brenda Donnelly Real Estate. With a background in professional photography and design, she oversees the firm’s social media presence, brand aesthetics, and visual communications.
Her work ensures consistency, refinement, and authenticity across all platforms, supporting the brokerage’s luxury positioning and client experience.
Marci Bracco Cain oversees brand strategy, messaging, and public relations for Brenda Donnelly Real Estate. Her work focuses on institutional tone, narrative clarity, and global referral readiness across all marketing channels.
