By What’s Up? Media
Local agents share their opinions and experiences with our market
Real estate is an ambitious and ever-evolving industry highlighted by market statistics and technology intersecting with “boots-on-the-ground” expertise and perspectives. One real estate agent could describe a property on the market differently than another. Prices fluctuate with economic pressures and consumer trends. Amenities that are fashionable one year may not hold as much value as the next. And, of course, buyers and sellers may or may not agree when negotiating a property. When they do, it can feel like heaven for both parties.
What’s Up? Media wants to help you along the golden road toward home ownership. And so, we’ve pinged local real estate professionals for their market insights and advice. The following Q&A will hopefully help guide you toward your next purchase or sale. We begin by asking…
The public sentiment seems to lean toward the market being a “sellers’ market,” but buyers are finding great value and opportunity, too. What is your assessment of the local/regional real estate market and its near future?
“There’s been a shift towards a more balanced market as inventory levels have continued to rise. Sellers are still benefiting from high buyer demand and several years of appreciation but are becoming more flexible with regards to pricing and buyer negotiations. A successful home sale always comes down to price and condition. The ‘Pie in the sky’ pricing strategy, especially without the necessary exemplary condition/location that this required, has backfired in the recent resale market and some sellers are understanding they have to realistically price in order to successfully sell. As market sentiment continues to settle, more buyers may reenter the home buying market.”—Christy Bishop of Berkshire Hathaway HomeServices PenFed Realty
“The Annapolis and Eastern Shore luxury waterfront markets remain incredibly resilient. Inventory is still tight in some segments, particularly for turnkey homes with deep-water access, but there are opportunities for serious buyers who are ready to act quickly. As we move through 2025, I anticipate a continued uptick in well-priced listings and a healthy demand from buyers who value the Chesapeake Bay lifestyle. Even in a seller’s market, knowledgeable buyers are finding long-term value—especially when they work with an agent who knows the waterfront inside and out.”—Brad Kappel of TTR Sotheby’s International Realty
“The interesting thing about today’s market is the market segmentation. For example, it is a tremendous seller’s market for homes just under a million dollars in water privileged communities in preferred school districts. On the other hand, it is a deep buyer’s market in the same zip codes for waterfront homes above three million dollars. It is uneducated to apply a label to the whole market. A discerning professional examines the segment closely and uses absorption rate to label the market.” —David Orso of Berkshire Hathaway HomeServices PenFed Realty
What excites you about real estate today, and the industry overall?
“How dynamic and ever evolving the industry is. Every market shift, whether it’s technology-driven or economic, creates new opportunities to serve clients better. I’m especially inspired by how innovation—like AI, virtual tours, and advanced data analytics—is enhancing the way we market properties, understand trends, and provide value. It’s making the buying and selling experience more efficient, informed, and personal than ever before.”—Mia Anderson of Berkshire Hathaway HomeServices Homesale Realty
“Our local area is thriving on the same principles, which led to tremendous growth 50 years ago. Proximity to major metropolitan markets, access to airports, superior outdoor living and water access, small town vibes, and a sense of community. We stand on the same foundation and a renaissance is in full effect.”—David Orso of Berkshire Hathaway HomeServices PenFed Realty
“Recent innovations passed nationally for selling investment properties that avoid or delay capital gains through nontraditional 1031 exchanges, so sellers are not required to purchase more brick-and-mortar properties, yet still able to access tax advantages like a traditional 1031 tax deferred exchange. Locally here, Anne Arundel County’s passage of Accessory Dwelling Unit (ADU) legislation to expand housing options affordably by allowing a homeowner to build a second dwelling unit on their existing property.”—Christy Bishop of Berkshire Hathaway HomeServices PenFed Realty
What are some best practices for buyers entering the market and how they can approach finding their dream home?
“Start with clarity—define what matters most: water depth, commute, school district, or proximity to downtown Annapolis or Eastport. Then, align yourself with a seasoned waterfront specialist who understands tidal data, riparian rights, and FEMA flood zones. In this competitive market, being pre-approved and prepared to act is essential. Buyers who trust the process and stay engaged will find the right home—and often, off-market opportunities are through a well-connected agent.”—Brad Kappel of TTR Sotheby’s International Realty
“Buyers entering the market are going to set themselves up for greater success by making sure they get their best team of representation together up front. This means pairing up with an experienced professional agent that already has a network to pave the path for success for them. Thinking you can educate yourself or just use a friend who has a license will be a hard lesson. Mistakes can be really expensive in real estate, from costly home inspection misses to extreme risks to your health from things like radon gas not being tested in this area. An experienced agent is priceless when it comes to buying a home.”—Christy Bishop of Berkshire Hathaway HomeServices PenFed Realty
For sellers considering listing their home, what preparations should they take in advance of pricing and marketing it?
“Understand the 2025 market. Covid is over; that was four years ago. Recency of sales and trends is extremely important. Dig deep on research and understand the important relationship between the condition of the home and pricing of the home.”—David Orso of Berkshire Hathaway HomeServices PenFed Realty
Technology has greatly enhanced the marketing experience in the past decade; what are some of your favorite tech/marketing tools that you utilize?
“We leverage every digital touchpoint available—from cinematic video tours and drone flyovers to SEO-optimized listing pages and social media content and geo-targeted ads. Our proprietary media partnerships and GPS ad units allow us to showcase listings in national publications. The goal is simple: maximum exposure to the most qualified buyers—locally and beyond.”—Brad Kappel of TTR Sotheby’s International Realty
What are some of the most sought-after property amenities that buyers are asking for?
“Buyer preferences can shift over time, but there are definitely some consistent trends we’re seeing in today’s market. Right now, some of the most in-demand property amenities include:
“Home Office Space: With remote and hybrid work becoming more common, buyers are placing a high value on having a dedicated, quiet workspace—often with good natural light and privacy.
“Outdoor Living Areas: Features like covered patios, outdoor kitchens, decks, and well-landscaped yards are very popular, especially in regions with mild climates. People want space to entertain or relax outside.
“Updated Kitchens and Bathrooms: These rooms still top the list in terms of ROI and desirability. Buyers often look for modern appliances, quartz or granite countertops, and walk-in showers or soaking tubs.
“Energy Efficiency: Features such as solar panels, high-efficiency HVAC systems, double-pane windows, and smart thermostats are increasingly important as buyers look to lower utility costs and reduce their environmental impact.” .”—Mia Anderson of Berkshire Hathaway HomeServices Homesale Realty
Where are the most sought-after communities on the western side of the Bay Bridge? And on the Eastern Shore?
“On the western shore, Annapolis remains the crown jewel—particularly communities like Bay Ridge, Wardour, and Fishing Creek Farm. Eastport continues to draw buyers who want a walkable lifestyle near Spa Creek and downtown. On the Shore, we’re seeing increased demand in Queenstown, Stevensville, and the Bay Bridge Marina area, where new developments like Sunset Wharf are bringing luxury waterfront living, with Hinckley owned and operated marina access to the Eastern Shore.”—Brad Kappel of TTR Sotheby’s International Realty
Besides realtors and their roles in negotiating a property transaction, what other contracted services must buyers and sellers be aware of and carefully vet?
“A real estate transaction is truly multifaceted. While Realtors play a central role in guiding negotiations and managing the flow of the transaction, there are several other contracted services that both buyers and sellers must be mindful of, each of which can significantly impact the success and smoothness of the deal. Carefully vetting these professionals is essential:
“Home Inspectors: For buyers especially, a home inspection is one of the most critical steps. A thorough, unbiased inspector can uncover issues that may not be visible during a showing. It’s important to choose someone licensed, experienced, and with a reputation for honest, detailed reporting—not someone who glosses over problems to keep a deal moving.
“Contractors/Repair Professionals: Sellers often need pre-listing repairs or improvements, and buyers may need estimates for future work. Reliable contractors with a history of quality workmanship in a timely manner and fair pricing are invaluable—and hard to come by on short notice. Always vet early.
“Insurance Agents: Buyers will need homeowner’s insurance to close. Rates and coverage vary widely, especially in areas with weather or liability risks. Choose agents who can shop multiple carriers and understand the unique nuances of the property.
“The bottom line is that every professional involved in a real estate transaction plays a part in its success—or failure. As an experienced Realtor, I’ve built a trusted network of vetted professionals and always guide my clients toward quality and integrity at every step. The details matter—and so do the people handling them.”—Mia Anderson of Berkshire Hathaway HomeServices Homesale Realty
