By The Whitcomb Group
Most real estate teams are built around a single person's ambition. Ours was built around a family's connection to a place. Stan and Scott Whitcomb grew up in Naples at a time when much of what you see today was still open land and undeveloped coastline. That history, knowing this market before it became what it is and watching it grow through every cycle, is not something you can replicate with a license and a few years of sales experience. It is what makes the results we deliver possible.
Key Takeaways
- The Whitcomb Group is a third-generation Naples real estate team with over $550 million in career sales
- The team has a documented track record of record-setting sales across Naples neighborhoods, including Naples Park
- Stan and Scott Whitcomb bring complementary expertise: Stan in luxury marketing and development sales, Scott in long-term local market knowledge
- The team serves buyers and sellers across Naples, Marco Island, Bonita Springs, Estero, and Fort Myers
Three Generations Rooted in Naples
Real estate runs in the Whitcomb family. Stan and Scott's father was a builder, and that exposure to construction, development, and the physical nature of real estate gave both brothers a foundation that most agents never acquire. Stan began his career in media and advertising, working with multiple Fortune 500 companies before moving into luxury real estate development sales with some of the largest developers in Southwest Florida. Scott has spent more than 33 years building relationships in Naples and developing a depth of neighborhood knowledge that comes only from decades of direct market experience.
Together, they bring more than 40 years of combined expertise to every transaction, along with a team of professionals who share their standards for client service and local knowledge.
Together, they bring more than 40 years of combined expertise to every transaction, along with a team of professionals who share their standards for client service and local knowledge.
What three generations in Naples means for our clients
- Relationships with builders, developers, and community insiders across every major Naples neighborhood
- Firsthand knowledge of how specific communities have evolved in value, character, and buyer profile over time
- A track record that spans multiple market cycles, including boom years, correction years, and recovery years
- Access to off-market opportunities that never reach the public listings
A Track Record Built on Results
Over $550 million in career sales is a number worth putting in context. In a market where the median luxury transaction often exceeds $2 million, that volume represents hundreds of clients who trusted us to deliver and received results that reflected it.
Our record-breaking sales are not the product of favorable market timing alone. They come from precise pricing, strategic positioning, and the kind of buyer network that only a team with deep roots and long-standing relationships can access.
Our record-breaking sales are not the product of favorable market timing alone. They come from precise pricing, strategic positioning, and the kind of buyer network that only a team with deep roots and long-standing relationships can access.
Notable results that define our approach
- Record sale price in Naples Park with a contract signed in three days. This is the outcome of accurate pricing and strong buyer network activation, not luck.
- Beachfront sales in difficult buyer markets where clients have cited our ability to identify qualified buyers for challenging properties under competitive conditions.
- Uninhabitable properties sold quickly because we have represented sellers with properties most agents would decline, finding multiple interested buyers within days through creative positioning and network reach.
- Luxury development sales including direct sales at Talis Park, one of Naples' most prestigious gated communities, where Stan helped establish pricing benchmarks that shaped the broader North Naples market.
Every record sale we set reflects a specific combination of preparation, market knowledge, and execution. None of them happen by accident.
The Markets We Know Best
The Whitcomb Group serves the full sweep of Southwest Florida's most desirable communities. Within each market, we bring granular knowledge of which streets command premiums, which communities are positioned for appreciation, and which developments deliver on their amenity promises.
Our primary markets
- Naples covers everything from Old Naples and Port Royal on the waterfront to North Naples, Pelican Bay, and the gated communities along Vanderbilt Beach Road.
- Marco Island includes waterfront estates, Gulf-front condominiums, and the distinct lifestyle of Southwest Florida's largest barrier island.
- Bonita Springs and Estero are growing communities with strong new construction activity and proximity to both Naples and Fort Myers.
- Fort Myers offers a broader market with significant investment activity and a diverse range of property types.
Naples has more gated communities per capita than nearly anywhere else in the country, and each one has its own pricing dynamics, HOA structures, and buyer profile. Understanding those nuances is what separates a local expert from a generalist.
What Sets The Whitcomb Group Apart
The Naples luxury market in 2026 is more competitive and more informed than at any point in its history. Buyers arrive with research, specific requirements, and the expectation that their agent can match their level of preparation. Sellers need someone who can position a property precisely, market it to the right audience, and close at a number that reflects actual market value.
Our approach to every transaction
- Seller representation includes strategic pricing grounded in micro-market data, combined with marketing reach across print, digital, and agent-to-agent networks.
- Buyer representation follows a patient, methodical search strategy that prioritizes long-term value over short-term availability.
- New construction guidance draws on direct relationships with developers across Naples' active communities, with the insight to assess which projects are worth the premium and which carry hidden risk.
- Off-market access comes from a buyer database and agent network built over decades, creating opportunities that never appear on the MLS.
Our clients do not just get a transaction. They get a team that stays connected to their real estate interests long after the closing.
FAQs
How long has The Whitcomb Group been operating in Naples?
The Whitcomb Group is a third-generation Naples real estate team. Stan and Scott Whitcomb grew up in Naples and have been active in the market for a combined total of more than 40 years. Their family's history in Florida real estate and construction extends well beyond that.
What types of properties does The Whitcomb Group specialize in?
We specialize in luxury residential properties across Southwest Florida, including waterfront estates, Gulf-front condominiums, gated community homes, and new construction. We also have extensive experience with investment properties and golf course communities across the Naples, Bonita Springs, and Estero markets. The Naples Area Board of REALTORS® provides public market data that gives buyers and sellers additional context for understanding current conditions in the communities we serve.
Does The Whitcomb Group work with buyers who are relocating from out of state?
Yes, and this is a significant part of what we do. Buyers relocating from California, New York, Illinois, and other states make up a large share of the Naples luxury market. We guide out-of-state buyers through the full process, from community selection and lifestyle fit to contract review and closing logistics, so that the decision feels informed rather than rushed.
Work With The Whitcomb Group in Naples
Three generations of Naples knowledge, over $550 million in career sales, and a client-first approach that treats every transaction as a long-term relationship. That is what we bring to every buyer and seller we work with. Reach out to us to learn more about our work in Naples and how we can help you buy or sell.
