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Can I sell my investment real estate using a 1031 exchange and buy a vacation home that I can enjoy with my family during the summer months?
No. You can sell your investment real estate and reinvest the gain, tax deferred, to purchase your vacation or second home, the challenge is making sure it will qualify as a 1031 investment property. Meaning that during the initial 24 months of ownership there are strict rules to follow regarding personal use. The important rule is that you can only use the property for 14 days each year or 10% of the actual days that you rent it out. For example, if you lease it for 200 days each year, your personal use can be up to 20 days. If you are able to abide by these rules, after two years the dream vacation home is yours to use as often as you like without any more requirements.
Jack Papaleonti, GRI/Realtor®; The Anchor Team of Academy Realty
Are home prices expected to go down anytime soon?
In most markets, a significant drop in home prices is unlikely because inventory remains relatively low and buyer demand continues to outpace supply. While some areas may see slower appreciation or minor price adjustments, experts generally expect home values to remain stable or continue growing at a more moderate pace.
Leslie Shafer; Omnia Real Estate
Are we on the back end of the “real estate boom”?
The boom is over. Data has conclusively shown the boom was the “Covid Years” from mid-2020 through 2022. The market plummeted from 12,152 homes sold in 2021 to 6970 homes sold in 2023. In 2024, we observed the market flatten out with the number of homes similar to the prior year. Naturally, the number of homes sold is related to the number of listings presented to the market. Here’s the catch; demand is outpacing supply, so we remain in a seller’s market and pricing is holding firm. The flattening of sales could be misleading on the surface without a deeper understanding of all market factors. Data leaves clues!!
David Orso; The David Orso Team of Berkshire Hathaway Home Services | Pen Fed Realty
Has the luxury real estate market shifted, or does it still favor sellers?
The luxury market has entered a more balanced phase, and that’s a healthy shift. Well-positioned homes continue to perform when pricing, timing, and presentation are handled thoughtfully. Today’s buyers are informed and intentional, which rewards sellers who approach the market with clarity and a strong strategy from the start. When those elements align, luxury properties continue to trade at a high level.
Brad Kappel; TTR | Sotheby’s International Realty
Many clients come to you specifically for buyer representation. What do they tend to be looking for?
Most buyers want the same thing. They want someone who listens, tells them the truth, and helps them make smart decisions without pressure. Especially in competitive markets, buyers do not want to feel rushed or outmatched. They want a plan. My role is to help them understand their options clearly and move forward with confidence, whether that means acting quickly or waiting for the right opportunity.
Alex Clark; TTR | Sotheby’s International Realty
When is the best time to list a waterfront home?
To really understand this question starts with an understanding that most waterfront buyers have specific criteria and take their time to find a home which meet their requirements. Therefore, it is less about timing the market and more important to present the home properly with content rich information for the discerning buyers. The fact is 65% of waterfront homes were listed in the first half of the year so the competition is heaviest in the spring market. The reason for the early presentation of inventory is simply because most waterfront home sellers think their home presents the best in the spring with landscape in full bloom and the strong desire of buyers to be out on the water.
Sue Steward; The David Orso Team of Berkshire Hathaway Home Services | Pen Fed Realty
How important is pricing a home correctly in today’s market?
Proper pricing is one of the most important factors in a successful home sale. Buyers have access to extensive market data and quickly recognize when a home is overpriced. Pricing a property accurately from day one helps maximize interest, increase showing activity, and may even lead to multiple offers. A thoughtful pricing strategy based on current market conditions gives sellers the best opportunity to achieve the highest possible value.
Bridgette Jacobs; Long & Foster Real Estate - Severna Park Office
What distinct lifestyle elements or community characteristics make the Annapolis real estate market so uniquely special?
As a mother, grandmother, real estate professional, and proud Annapolis resident for more than 40 years, I’ve come to believe that life here is truly defined by the water. From sunrise paddles on quiet creeks to afternoons spent on the Chesapeake Bay, the area’s natural beauty becomes part of everyday life. Annapolis is a community where boating, sailing, waterfront traditions, and the freshest local seafood create an unmatched way of living. Residents enjoy strolling historic streets, browsing locally owned shops, attending live theater and music, and gathering at waterfront restaurants with spectacular views. Parks, marinas, and miles of shoreline encourage an active outdoor lifestyle year-round. Conveniently located between Washington, DC, Baltimore, and the Eastern Shore, Annapolis offers a rich environment where history, recreation, and the Chesapeake Bay come together. Buyers aren’t simply purchasing a home—they’re embracing a lifestyle built on community, natural beauty, and lifelong memories.
Michele Cordle; Annapolis Fine Homes of Long & Foster Real Estate
Do we need to make repairs or updates before we list our home?
Before you spend a dollar, let’s talk. I’ll walk through your home and tell you what will actually increase buyer interest and value—and what you can skip. If updates make sense, I can connect you with trusted, licensed pros, and in some cases the cost can be deferred until after closing. The goal is simple: maximize your return and avoid wasted time and money.
Christy Bishop; Associate Broker; Berkshire Hathaway HomeServices PenFed Realty
What is the biggest challenge for Annapolis home sellers right now?
The biggest challenge is assuming the market will do all the work. We are still seeing strong buyer demand in Annapolis, Severna Park, and the surrounding communities, but buyers are more selective than they were a few years ago. Pricing, preparation, and presentation matter. The homes getting the best results are the ones that feel ready, show well online, and are positioned correctly from day one. Sellers do not need to overdo every update, but they do need a smart plan. The right strategy can create stronger interest, better terms, and a smoother path to the closing table.
Jen Holden; The Jen Holden Group of Compass
In today’s ever-changing real estate landscape, where do you see the future of real estate?
After thirty years in real estate, I know one thing for certain: this business never stands still. Technology, data, digital marketing, artificial intelligence, and consumer expectations are changing faster than ever. The agents and companies who stay ahead of those changes will create a better, more efficient client experience. Those who do not will be left behind. But technology alone will never replace experience, judgment, and relationships. The future of real estate belongs to professionals who can combine innovation with true service using every available tool to simplify the process, anticipate challenges, and guide clients with confidence from the first conversation to the closing table.
Sandra Libby; Annapolis Fine Homes of Long & Foster Real Estate
How do I choose the best agent to sell my property?
When you are selling what is probably one of your largest assets, it’s important to have a true professional on your team. Your listing agent should have years of experience so they can deal with any issue that comes up during the negotiation or inspection period. Ask what preparation and marketing resources they will provide (staging? advertising?). Does their website get the kind of traffic your property deserves? Lastly, does your favorite candidate have an excellent reputation in the real estate community? It’s OK to ask for referrals! Kindness matters – along with all the professional attributes.
Buckley Waterfront Homes; Long & Foster Real Estate - Annapolis Eastport Office
What can I do to attract more showings and possibly receive multiple offers on my home?
Taking the time to get your home in prime condition is so important. A qualified Realtor will have the resources to guide you to be the hottest house in town. Buyers want new paint, new flooring, upgraded baths, and great new upgraded kitchen with updated appliances.
Giving your home a facelift prior to entering the market will pay off in price, a short time on the market and the possibility of multiple offers.
Christina Janosik Palmer; Christina Janosik Palmer Group of Keller Williams Flagship of Maryland
My property survey shows that a fence crosses the property line. Should I be concerned?
Not necessarily. Fence encroachments are relatively common and do not always prevent a real estate transaction from moving forward. An encroachment occurs when a fence extends onto a neighboring property or vice versa. Depending on the situation, the seller may agree to move the fence before closing, or the neighboring property owners may sign an agreement allowing it to remain in its current location. In some cases, a minor encroachment may be acceptable to the buyer, lender, and title insurer. Because encroachments can affect property rights and future use of the property, buyers should discuss the issue with their real estate agent, lender, title company, or attorney before closing.
Steve McClung, Esq.; Manor Title
Why should I choose a local REALTOR when buying or selling a home?
Local knowledge is one of the biggest advantages in real estate. For sellers, it means marketing not just the home, but the lifestyle that comes with it. For buyers, it means having someone who can answer the questions no listing can - where to find the best restaurants, parks, coffee shops, and community events. Having lived and worked on Maryland’s Eastern Shore nearly my whole life, I help clients understand what makes each community unique. A home is more than a property. It’s where life happens, and local expertise helps you find the right fit or attract the right buyer.
Elizabeth Arentz Boyer; Coldwell Banker Realty
What is the biggest mistake waterfront home sellers are making in today’s luxury market?
The biggest mistake is pricing based on yesterday’s market instead of today’s waterfront buyer. These buyers are exceptionally informed, comparing location, shoreline, water depth, flood risk, and overall lifestyle value - not just square footage. Your home’s debut is its most important marketing opportunity, making a strong first impression essential. Strategic pricing, elevated presentation, and targeted marketing generate early interest and qualified buyers. When a waterfront property is overpriced, it can quickly lose momentum, often resulting in longer market times and price reductions. The right launch strategy protects both value and negotiating power.
Biana Arentz; Coldwell Banker Realty
You hold a CIPS designation and host an international real estate series. How does that fit into a Maryland based business?
I’ve always been fascinated by how people choose where to live, not just the property, but the community and lifestyle behind it. The series started with Portugal: real people, real neighborhoods, what it’s actually like to buy, retire, or invest there, beyond the postcard version. It also translates directly into how I serve clients here. My CIPS designation and Sotheby’s sphere connects me to a vetted global network, which means my sellers aren’t just getting local exposure, their properties are marketed to qualified international buyers through Sotheby’s global reach. And for clients considering a move or purchase abroad, I’m not sending them off with a phone number and good luck. I personally connect them with trusted, vetted professionals in that market and stay involved, so they’re never navigating an unfamiliar country’s real estate process alone.
Erica Baker; TTR | Sotheby’s International Realty
In a market that continues to evolve, what do real estate professionals need most from their title partner today?
Today’s real estate professionals need more than a company that can simply get a transaction to the closing table. They need a partner they can trust to protect their clients, communicate proactively, and deliver a great experience from start to finish. A title company helps ensure a property’s ownership is clear, manages the closing process, and helps buyers and sellers transfer ownership safely. As technology and AI continue to reshape the industry, security, accuracy, and personal service have never been more important. Consumers also rely heavily on reviews and reputation, making trust the ultimate differentiator.
Brad Walsh, Esq.; President, Eagle Title
Should you stage your home when you sell?
Staging a home helps buyers emotionally connect with the property by showcasing its best features and maximizing its appeal. A well-staged home appears larger, brighter, cleaner, and more inviting, allowing buyers to envision themselves living there. Professional staging highlights functionality, minimizes distractions, and creates attractive spaces that photograph well for online marketing, where most buyers begin their search. Staged homes often receive more showings, generate stronger offers, spend less time on the market, and may sell for a higher price than un-staged homes. Investing in staging can provide an excellent return by helping your home stand out in a competitive real estate market.
DeeDee McCracken of Coldwell Banker Realty; O: 410-224-2200 | C: 410-739-7571
Affiliated real estate agents are independent contractor sales associates, not employees. ©2026 Coldwell Banker. All Rights Reserved. Coldwell Banker and the Coldwell Banker logos are trademarks of Coldwell Banker Real Estate LLC. The Coldwell Banker® System is comprised of company owned offices which are owned by a subsidiary of Realogy Brokerage Group LLC and franchised offices which are independently owned and operated. The Coldwell Banker System fully supports the principles of the Fair Housing Act and the Equal Opportunity Act.
What role do you think AI will play in the real estate industry?
AI has become a valuable tool in our business. I use it to refine marketing copy, identify the age, make, model, and specifications of home systems from a photo, brainstorm demographic advertising strategies, and examine pro forma data for commercial deals. Everything it produces still needs to be verified, but there’s no question it streamlines many of the technical, time-consuming tasks we encounter. I don’t see AI replacing experience or local knowledge. I see it as another tool that helps us work more efficiently, giving us more time to focus on our clients and the decisions that matter most.
Chuck Mangold Jr.; Benson & Mangold Real Estate
What do you recommend to buyers and sellers when they are searching for an agent on the Eastern Shore?
The most important thing is to work with an agent who truly understands the local market. Real estate is complex and specific — neighborhood trends, pricing strategies, off-market opportunities, and seasonal dynamics vary widely. Experienced agents with a deep knowledge of the area bring crucial insight into key factors such as critical areas, permitting requirements, and flood zones, to help avoid potential issues. Choose someone who communicates clearly, listens to your needs, advocates for you, and demonstrates integrity and professionalism. Buying or selling a home is a major financial and emotional decision — the right advisor can make all the difference.
Laura Carney; TTR | Sotheby’s International Realty
How do I know when it’s the right time to list my home?
While seasonality can play a role, the best time to list comes down to market conditions, not the calendar. We evaluate current inventory levels, buyer demand, competing listings, and how your property compares in today’s market. With inventory still limited across much of Maryland’s Eastern Shore, listing when competition is low can put your property in front of more qualified buyers, generate stronger interest, and help you achieve the best possible outcome.
Brian Gearhart; Realtor® | Team Lead; Chesapeake Bay Properties Team of Benson and Mangold
If you had one Saturday to introduce someone to the Eastern Shore, where would you go?
I’d start the morning at the Chestertown Farmers’ Market, then take a walk along the Chester River through Wilmer Park before heading to Rock Hall for lunch overlooking the harbor. From there, we’d hop on a charter boat, stop along Kent Narrows for a drink, and continue to St. Michaels for dinner. It’s a great way to experience the Eastern Shore’s small towns, scenic waterways, and relaxed pace—all in one Saturday.
Courtney Chipouras; TTR | Sotheby’s International Realty
Why are some homes selling quickly while others seem to sit on the market?
It usually comes down to preparation, pricing, and presentation. Today’s buyers are well-informed and emotional decision-makers—they know value and respond to homes that feel move-in ready and lifestyle-driven. Homes that are priced correctly, staged thoughtfully, and marketed with strong visuals and local insight consistently outperform the competition. In this market, it’s not just about listing a home—it’s about launching it the right way & choosing the right agent.
Tricia Wilson | Wilson Realty & Staging
Why is pricing strategy so critical when selling a waterfront home on the Eastern Shore?
Waterfront homes operate in a distinct market with fewer buyers and far more scrutiny. Pricing must be intentional and defensible. When pricing misses the mark, whether by stretching to test demand or misreading timing, momentum stalls quickly. Homes priced correctly from the start generate urgency, preserve negotiating power, and consistently achieve stronger results.
Joe Bray; TTR | Sotheby’s International Realty
How is the current Talbot County market?
Talbot County’s housing market is currently experiencing a mix of trends; indications of a more balanced market with the number of homes available for sale; yet the median sale price has increased compared to last year. My advice is to buy now for the market and not in the future for the interest rate.
Cornelia C.Heckenbach; Long & Foster Real Estate; Forbes Global Properties Specialist
You’ve been hired three times by HGTV. What was that experience like, and how has it influenced your business?
Being selected to work with HGTV three separate times was an incredible honor and a defining moment in my career. It reinforced what I’ve always believed—that thoughtful design has the power to transform not only a home, but the way buyers experience it. Those experiences sharpened my eye for detail, scale, flow, and presentation, and it continues to influence every home I prepare for market. While television is exciting, the greatest reward is bringing that same level of design expertise directly to my clients.
Jennifer Chaney; Chaney Homes
