With more than 25 years as a licensed real estate broker in Florida and 13 years serving clients in South Carolina, Penelope Whichello brings a depth of experience shaped by relationships, design sensibility, and a lifelong appreciation for exceptional homes and coastal living. Currently with teams in both states.
Drawn naturally to real estate from an early age, Penelope has always felt a calling to the profession — a career that allows her to connect deeply with people while immersing herself in architecture, interior design, and the ever-changing landscapes of the communities she serves. For her, real estate has never been about transactions alone, but about guiding people through meaningful life moments with care, clarity, and confidence. Showing care to each individual clients equity goals.
Penelope's work spans select markets in South Florida, including historic downtown Stuart, Palm City, and Sewall’s Point, as well as the Lowcountry of Beaufort, Hilton Head & Bluffton, South Carolina, where coastal charm, Southern hospitality, and a slower pace of life define the lifestyle. She specializes in custom-quality homes and second residences, typically representing properties valued above $700,000, and offers a boutique, highly personalized level of service to each client.
What Penelope values most — and what defines her career — are the enduring relationships she builds. Many of her clients become lifelong friends, returning to her time and again for multiple transactions and inviting her into their lives well beyond the closing table. With approximately 64% of her business representing both the buying and selling side, her reputation is rooted in trust, loyalty, and consistent results. She approaches every transaction as if it were for a family member, advocating fiercely, listening intently, and negotiating with purpose and discretion. A trait her high net worth clients appreciate.
Known for her calm presence and steady leadership, Penelope has mastered the art of remaining grounded during high-stakes negotiations and emotionally charged moments. Over time, she has learned that clarity, composure, and genuine listening often create the strongest outcomes — not just financially, but personally.
Outside of real estate, Penelope is a devoted Aunt to two successful & beutiful nieces & a cat mom to her beloved kitty, Tinker, a passionate traveler with a love for Europe, and a dedicated mindfulness practitioner. She also operates an online business teaching meditation and mindfulness tools specifically for real estate professionals, helping others cultivate focus, balance, and success in a demanding industry.
Whether representing a refined coastal residence or guiding clients through their next chapter, Penelope Whichello offers a rare blend of experience, integrity, and grace — delivering a real estate experience that is personal, elevated, and enduring.
Penelope Properties Inc. is a project oriented brokerage firm that focuses on its clients desired end result. Whether a residential single family neighborhood home, a vacation rental investment or a legacy building Historic Plantation property purchase.
Penelope Properties Inc. has launched a second office loft location in the prestigious Southern Living Inspired community of Habersham in the Historic Low Country Coastal town of Beaufort, South Carolina. This community is home to the Coastal Living Magazine Homes & several Southern Living Magazine events. We have the privledge in serving our US Armed forces from the Marine Corps Air Station of Beaufort and Paris Island as well as civilians.
Penelope Properties Inc. is located on the first level of the live work marketplace lofts ~ 21B Market Loft #1.
Consultations by appointment
Immediate Live Zoom Conferencing from anywhere in the USA or Internationally for the convenience of the discerning buyer. contact us Directly @772.486.2096.