Debbie Mangold Lipscomb Associate Broker with Benson & Mangold Real Estate

Debbie Mangold Lipscomb Associate Broker with Benson & Mangold Real Estate Local Trusted Connected This led me to co-found Eastern Shore Vacation Rentals, which I successfully owned and operated for 15 years.

Introducing Your Trusted Advisor for Maryland's Eastern Shore
With over 15 years of experience as a licensed agent and a track record as a top-producing salesperson, I am your trusted advisor for all your real estate needs on Maryland's Eastern Shore. Having grown up in this beautiful region, I possess an intimate understanding of its local intricacies and strong connections within the community.

My journey in real estate was influenced by my background in marketing and tourism, coupled with an unwavering passion for showcasing the wonders of the Eastern Shore to clients and friends alike. Through this venture, I built a vast customer base of individuals seeking memorable experiences on the Eastern Shore. For those interested in second homes or vacation rental investments, I possess a comprehensive knowledge of the market, rules, and regulations, as well as the income potential within each county. I can guide you through the intricacies of property ownership and help you make informed decisions based on your unique goals and preferences. The Eastern Shore offers a plethora of lifestyle options, from raising a family to embracing retirement, and from investing in second homes to seeking lucrative opportunities. I am committed to understanding your individual vision and helping you find the perfect version of the Eastern Shore lifestyle that aligns with your aspirations. As a proud graduate of Saints Peter and Paul High School in Easton and Mary Washington College, I am deeply rooted in the Eastern Shore community. I currently reside in Easton with my husband Darrin and our three sons, Sam, Will, and George. This personal connection to the area enables me to provide you with tailored advice and personalized service, ensuring your real estate journey is smooth and fulfilling. Let me be your guide and ally on Maryland's Eastern Shore as we embark on this exciting journey together. Reach out to me, and together we'll discover your perfect version of the Eastern Shore lifestyle.

Lavender season is in full bloom 🌿💜 Experience beautiful fields, live music, local vendors, and family-friendly fun at W...
06/04/2026

Lavender season is in full bloom 🌿💜
Experience beautiful fields, live music, local vendors, and family-friendly fun at Wildwood Lavender Farm this weekend.

06/04/2026
06/03/2026

POV: You just found the waterfront property you’ve been dreaming about. ✨

Acres of pristine lawn.
Breathtaking water views.
A setting that feels like a private retreat every single day.

Some homes check boxes.
Others create a lifestyle.

HELLO JUNE 🌿There’s something special about June on Maryland’s Eastern Shore.Hydrangeas begin to bloom, waterfront eveni...
06/01/2026

HELLO JUNE 🌿

There’s something special about June on Maryland’s Eastern Shore.

Hydrangeas begin to bloom, waterfront evenings stretch a little longer, and life slows down just enough to savor the season.

From historic homes and quiet docks to farmers markets and sunset cruises — this is the time of year that reminds people why they fall in love with the Shore.

What’s your favorite part of summer here?

🏡 UNDER CONTRACT | 29569 Porpoise Creek RoadEvery property has a story—and sometimes success comes from knowing when to ...
06/01/2026

🏡 UNDER CONTRACT | 29569 Porpoise Creek Road

Every property has a story—and sometimes success comes from knowing when to change the narrative.

After reassessing our marketing strategy and repositioning this beautiful homesite to better connect with today's buyers, we generated renewed interest that resulted in multiple offers and a successful contract.

Real estate isn't just about putting a property on the market; it's about understanding the market, recognizing opportunities, and adapting when needed.

Congratulations to my sellers! Thank you for trusting me throughout the process.

If you're considering selling and wondering how strategic marketing can impact your results, I'd be happy to discuss your options.

Coastal perfection and completely summer-ready ☀️🌊Tucked away in one of Oxford’s most charming locations, this beautiful...
05/26/2026

Coastal perfection and completely summer-ready ☀️🌊

Tucked away in one of Oxford’s most charming locations, this beautifully reimagined cottage delivers effortless Eastern Shore living just blocks from the waterfront, marinas, shops, restaurants, parks, and local market.

Inside, every space has been thoughtfully redesigned with light-filled interiors, custom built-ins, vaulted ceilings, a gourmet chef’s kitchen, formal dining room, cozy family room with gas fireplace, and seamless indoor-outdoor flow.

Step outside to your private backyard retreat featuring a fabulous rear deck, lush manicured gardens, and an in-ground pool made for long summer days and unforgettable evenings. 🏖️✨

A separate guest cottage with kitchenette and full bath adds the perfect touch for hosting family and friends or creating your own private escape.

Move-in ready and made for the coastal lifestyle you’ve been dreaming about.
Comment COTTAGE for a full listing details.

There is nothing quite like the sound of powerboats roaring across the Choptank to signal the start of summer. 🚤☀️The Ca...
05/21/2026

There is nothing quite like the sound of powerboats roaring across the Choptank to signal the start of summer. 🚤☀️

The Cambridge Classic PowerBoat Races on May 23 are one of those long-standing Eastern Shore traditions that locals look forward to all year. The energy along the waterfront is incredible — boats flying across the river, families gathered on docks and lawns, restaurants buzzing, and that unmistakable sense that boating season has officially arrived.

Events like this are part of what makes Cambridge so special. This is a town built around the water — from its working maritime roots to its vibrant yacht culture today. When clients ask me what waterfront living here truly feels like, I tell them to picture a day like race day: friends pulling up by boat, sunset over the Choptank, and a front-row seat to the action right from your own pier.

Cambridge offers everything from historic homes near the downtown marina to expansive waterfront estates just outside town — each with direct access to the kind of lifestyle that days like this represent.

If you’re coming into town for the races and find yourself imagining what it would be like to live on the water full-time, I’m always happy to share what’s available — and what makes each stretch of shoreline unique.

Summer on the Eastern Shore starts here. 🌊

On May 23, Chestertown does something truly special — it turns back the clock. 🇺🇸⚓The Chestertown Tea Party Festival is ...
05/20/2026

On May 23, Chestertown does something truly special — it turns back the clock. 🇺🇸⚓

The Chestertown Tea Party Festival is one of the most unique celebrations on the Eastern Shore, commemorating the town’s bold stand in 1774 when local patriots responded to British taxation by staging their own “tea party” in the Chester River.

For one weekend, history comes alive. You’ll see colonial reenactors marching through town, tall ships along the waterfront, live music, local vendors, and — of course — the dramatic reenactment of tea being tossed overboard. It’s immersive, festive, and a powerful reminder of the deep Revolutionary roots that shape so many of our waterfront communities.

History, community, and life on the water — that’s the Eastern Shore at its finest.

Address

31 Goldsborough Street
Easton, MD
21601

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