Debbie Mangold Lipscomb Eastern Shore MD Realtor

Debbie Mangold Lipscomb Eastern Shore MD Realtor 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.

OPEN SATURDAY 🏡 | NOW $569,000Close to town. More room to breathe. And a new price.If you love the idea of being minutes...
09/18/2026

OPEN SATURDAY 🏡 | NOW $569,000

Close to town. More room to breathe. And a new price.

If you love the idea of being minutes from downtown Easton, the YMCA and Idlewild Park—but don't necessarily want the smaller lot and close neighbors that can come with an in-town location—11 Londonderry Drive deserves a look.

Set on more than half an acre in Thread Haven, this 3-bedroom, 2.5-bath home offers a fenced backyard, two-car garage, wraparound porch, fireplace and a long list of thoughtful improvements.

Come see it for yourself this Saturday.

OPEN HOUSE
đź“Ť 11 Londonderry Drive, Easton
đź“… Saturday, September 20
⏰ 11:00-1:00
đź’° NEW PRICE | $569,000

Sometimes a home makes much more sense once you walk through the door. Come take a look!

✨ NEW PRICE | $569,000Looking for the convenience of being close to downtown Easton—but with a little more room to breat...
09/16/2026

✨ NEW PRICE | $569,000

Looking for the convenience of being close to downtown Easton—but with a little more room to breathe?

11 Londonderry Drive offers the best of both worlds.

Located in the highly sought-after Thread Haven neighborhood, this thoughtfully updated home sits on more than half an acre with no HOA, a fenced backyard, two-car garage, wraparound front porch and a wonderful private setting.

And the location? Minutes from downtown Easton, the YMCA, Idlewild Park, restaurants, shopping and everything that makes Easton such a great place to call home.

🏡 3 Bedrooms | 2.5 Baths
🌳 .57± Acre
đźš— 2-Car Garage
🔥 Fireplace + New Outdoor Fire Pit
✨ Numerous Recent Updates
đź“Ť Thread Haven | Easton, Maryland
đź’° Now Offered at $569,000

OPEN HOUSE THIS SATURDAY
September 22 11:00AM-1:00PM

If you’ve been waiting for the right Easton home—or the right price—come take another look.

đź“Ť 11 Londonderry Drive, Easton, MD

✨ OFFICIALLY UNDER CONTRACT | 92 LONG CREEK ROAD ✨This exceptional Kent Island waterfront property is officially UNDER C...
09/08/2026

✨ OFFICIALLY UNDER CONTRACT | 92 LONG CREEK ROAD ✨

This exceptional Kent Island waterfront property is officially UNDER CONTRACT!

With more than 2.5 acres, a private pier, swimming pool, outdoor kitchen, six-car garage space, and plenty of room for family and friends, 92 Long Creek Road offered something increasingly hard to find: a true waterfront retreat designed for weekends on the Shore.

From boating and pool days to sunset dinners and long weekends with a house full of guests, this property captured exactly what so many buyers are looking for when they dream about an Eastern Shore getaway.

I’m thrilled for my sellers as we move toward closing—and excited for the buyers who will soon get to call this special place their own.

Thinking about selling a waterfront or second home on Maryland’s Eastern Shore? The right positioning, presentation, and targeted exposure can make all the difference.

đź“Ť 92 Long Creek Road | Stevensville, Maryland

JUST SOLD | 24645 Long Haul Road, St. MichaelsThere’s nothing better than handing over the keys to the right home—especi...
09/08/2026

JUST SOLD | 24645 Long Haul Road, St. Michaels

There’s nothing better than handing over the keys to the right home—especially when the journey to get there had a few twists and turns along the way.

I’m absolutely thrilled for my clients, who are officially settling into the Eastern Shore lifestyle on beautiful Long Haul Creek in St. Michaels.

Real estate isn’t always smooth sailing. Sometimes getting from contract to closing takes persistence, creative problem-solving, strong local relationships, and the right resources behind the scenes. That’s when experience really matters.

So happy we were able to navigate the challenges, bring this one across the finish line, and get my clients exactly where they wanted to be.

Welcome home! ⚓️🏡

đź“Ť24645 Long Haul Road | St. Michaels, Maryland

08/27/2026

Think 22+ private waterfront acres, more than 1,000 feet of shoreline, sweeping southwest water views, resort-style outdoor living, and gracious spaces designed for gathering—all in one extraordinary setting on Maryland’s Eastern Shore.
Life at 24679 Deep Neck Road looks like:

Morning light streaming into beautifully appointed living spaces overlooking the water.

Cooking and entertaining in a kitchen designed to bring everyone together.

Working, relaxing, and gathering in a home that feels equally suited to quiet weekends and a house full of family and friends.

Long afternoons by the pool and spa, followed by bocce, cocktails around the fire pit, and spectacular Eastern Shore sunsets.

Evenings on the vaulted three-season porch, watching the light change across the water.

Privacy, calm, and room to breathe—yet just minutes from St. Michaels and Easton.

A main-level primary suite that feels like a private retreat, plus a beautifully appointed guest apartment that gives family and friends a space of their own.

Set on more than 22 acres in Royal Oak, 24679 Deep Neck Road offers something increasingly difficult to find: the privacy and scale of a true waterfront estate combined with the relaxed, effortless lifestyle that makes Maryland’s Eastern Shore so special.

This isn’t simply a beautiful home. It’s the kind of place where weekends become traditions.

JUST LISTED | YOUR CHESAPEAKE WEEKEND STARTS HERE âš“Imagine leaving the week behind and arriving to this: more than 2.5 p...
08/25/2026

JUST LISTED | YOUR CHESAPEAKE WEEKEND STARTS HERE âš“

Imagine leaving the week behind and arriving to this: more than 2.5 private waterfront acres, your own pier, a sparkling pool, outdoor kitchen, and plenty of room for everyone to stay for the weekend.

Welcome to 92 Long Creek Drive in Stevensville—a turnkey waterfront retreat where the hard work has already been done. Just bring your boat, your friends, and your plans for the weekend.

With 5 bedrooms, 4 baths and more than nearly 4000 square feet of finished living space, there’s room to gather without feeling crowded. Outside, the property becomes your own private resort—spend the day on the water, come home for a swim, fire up the outdoor kitchen, and settle in for a long evening by the pool.

And for the boaters, the private deep water pier puts the Chesapeake lifestyle right outside your door.

Best of all? This is the kind of second home that’s meant to be enjoyed, not managed. A turnkey furnished option makes it possible to start living the Eastern Shore lifestyle from day one.

đź“Ť 92 Long Creek Drive | Stevensville, Maryland
Now on the market.

Message me for details or to schedule a private tour or comment "Long" for a link to the full listing.

Debbie Mangold Lipscomb
Associate Broker | Benson & Mangold Real Estate

✨ Historic St. Michaels charm, beautifully reimagined.Welcome to the William J. Wrightson House , a beautifully restored...
08/24/2026

✨ Historic St. Michaels charm, beautifully reimagined.

Welcome to the William J. Wrightson House , a beautifully restored c. 1897 residence in the heart of St. Michaels—just steps from the waterfront, marinas, shops, and restaurants.

This distinctive 3-bedroom, 3-bath home blends timeless Eastern Shore character with the comfort and craftsmanship of an extensive top-to-bottom renovation.

Inside, natural light highlights original **heart pine and yellow pine floors, custom millwork, and gracious living spaces. A new gas fireplace anchors the living room, while the gourmet kitchen offers quartz countertops, top-tier appliances, generous cabinetry, and custom built-ins.

The showpiece of the home may be the extraordinary sunroom overlooking the English garden. With vaulted ceilings, shiplap, custom built-ins, and a beautifully designed butler’s pantry with beverage chiller and bar sink, it’s an inviting space made for relaxed gatherings and effortless entertaining. French doors open to a brick patio surrounded by lush gardens.

Upstairs, the serene primary suite features a luxurious marble bath with a clawfoot soaking tub, antique vanity, and glass-enclosed walk-in shower. Two additional bedrooms and a renovated hall bath welcome family and guests.

Outside, a private English garden filled with roses, hydrangeas, and crepe myrtles creates an enchanting retreat, framed by a charming French Gothic lattice fence.

Thoughtfully restored. Beautifully designed. Exceptionally located.

Historic St. Michaels living at its finest.

đź“Ť St. Michaels, Maryland
🏡 3 Bedrooms | 3 Baths
🌿 Private English Garden
âš“ Steps from the St. Michaels waterfront

DM me for additional details or to schedule a private showing.

✨ More space. More privacy. No HOA. And just minutes from downtown Easton.Welcome to 11 Londonderry Drive, a beautifully...
08/23/2026

✨ More space. More privacy. No HOA. And just minutes from downtown Easton.

Welcome to 11 Londonderry Drive, a beautifully updated home in Easton’s established Thread Haven neighborhood, where comfortable living meets the Eastern Shore lifestyle.

Set on more than half an acre, this inviting property gives you room to spread out—inside and out. Start your morning with coffee on the wraparound front porch, let the dogs or kids enjoy the fenced backyard, and end the day gathered around the new fire pit and flagstone path.

Inside, natural light and an easy, open flow make the home equally suited to quiet everyday living and entertaining. The kitchen features a newly constructed pantry, generous workspace, and statement pendant lighting by award-winning designer Lightexture.

Thoughtful updates continue throughout, including:

• New roof (2020)
• Custom primary bedroom closet
• Energy-efficient water heater
• Updated lighting throughout
• Fresh interior paint
• New front porch stairs & railing
• Re-stained deck and porch
• Refreshed landscaping
• Two-car garage
• Crawl-space v***r barrier

And one of the best features? No HOA.

With a spacious lot, welcoming outdoor spaces, smart updates, and easy access to downtown Easton, shopping, dining, parks and healthcare, 11 Londonderry Drive is ready for its next chapter.

đź“Ť 11 Londonderry Drive | Easton, MD

Come see why this one feels like home. Comment "Thread" for the link to pricing and more information.

Waterfront living, elevated. ⚓️Welcome to Wells Cove Townhomes & Marina, where sweeping Chesapeake Bay views, deep-water...
08/10/2026

Waterfront living, elevated. ⚓️

Welcome to Wells Cove Townhomes & Marina, where sweeping Chesapeake Bay views, deep-water boating, and effortless luxury come together in the heart of Kent Narrows.

This extensively renovated end-unit waterfront residence offers approximately 3,500 square feet across four beautifully designed levels—with a private elevator connecting them all.

✨ 4 Bedrooms | 4.5 Baths
✨ Private elevator to all four levels
✨ Four covered waterfront decks
✨ Deeded deep-water boat slip
✨ Oversized 2-car garage
✨ Two spacious owner suites
✨ Chef’s kitchen with custom cabinetry & premium appliances
✨ Loft + recreation room with wet bar
✨ Sweeping marina & Chesapeake Bay views

Thoughtfully renovated with rich hardwood floors, custom millwork, designer lighting, and sophisticated finishes, every detail has been designed for comfort, entertaining, and an effortless lock-and-leave waterfront lifestyle.

And for boaters? Your deeded slip offers approximately 4' mean low water with convenient access to the Chesapeake Bay—making it easy to go from your front door to open water.

Spend mornings with coffee overlooking the marina, afternoons cruising the Bay, and evenings watching spectacular Chesapeake sunsets from one of your four private decks.

All just moments from Kent Narrows’ waterfront restaurants, marinas, the Cross Island Trail, shopping, golf, and Route 50.

Turnkey. Waterfront. Exceptional.

Simply arrive, settle in, and start enjoying the Chesapeake Bay lifestyle from day one.

đź“Ť Wells Cove Townhomes & Marina | Kent Narrows, Maryland

DM me for pricing, additional details, or a private showing.

Some homes are simply owned. Others become part of history.Welcome to White Barn at Middlespring — an extraordinary 8-ac...
07/30/2026

Some homes are simply owned. Others become part of history.

Welcome to White Barn at Middlespring — an extraordinary 8-acre estate where nearly 200 years of Eastern Shore history meet timeless luxury. 🌿

At the end of a private quarter-mile drive, surrounded by open farmland, you'll discover a beautifully restored 1824 manor home, a historic 40' x 63' barn, and a detached 3-car garage with finished bonus space—all thoughtfully updated for today's lifestyle while preserving the property's remarkable character.

Inside, original wide-plank pine floors, three wood-burning fireplaces, exposed beams, and a stunning farmhouse kitchen create warm, inviting spaces designed for gathering. Recent renovations—including updated kitchens and baths, new windows, a new metal roof, composite decking, and a sunroom with a cozy propane stove—make this historic home completely move-in ready.

Step outside and experience the peaceful rhythm of Eastern Shore living. Sip your morning coffee overlooking eight private acres, entertain under the stars with landscape lighting illuminating the grounds, or simply enjoy the serenity that comes from having room to breathe.

✨ Even better? The home is offered fully furnished with curated pieces from Restoration Hardware, Arhaus, and Pottery Barn, making it effortless to begin your next chapter from day one.

This is more than a home—it's a legacy property offering history, privacy, and the quintessential Eastern Shore lifestyle just minutes from downtown Easton.

đź“© Message me for a private tour or additional details.

Address

31 Goldsborough Street
Easton, MD
21601

Telephone

+14103102830

Website

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