Heather Dolan, Realtor at Chesapeake Real Estate Associates, LLC

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Heather Dolan, Realtor at Chesapeake Real Estate Associates, LLC

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REALTOR® | Chesapeake Real Estate Associates, LLC | Serving MD's Eastern Shore + Beyond Coffee in hand, keys in the other ☕️🗝️
📲 443-404-4332
📧[email protected]

06/18/2026

Loving the sunshine, summer dresses, and these longer days. ☀️💕

It’s been a busy week filled with waterfront buyer tours, end-of-school-year celebrations, staging projects, cleaning houses, and getting a beautiful new listing ready for the market. Photos were taken today, and I can’t wait to share this one with you later this week.

Summer is officially here, and I’m looking forward to packing a few suitcases, making memories with my family, and squeezing in some adventures along the way.

Life is busy, a little chaotic at times, and exactly where I want to be.

Heather Dolan, REALTOR®
Maryland Real Estate
Chesapeake Real Estate Associates, LLC
📲 443-404-4332 | 📞 443-215-HOME
🔗 https://linktr.ee/heatherdolanrealtor

06/17/2026

Today was a big day. 🎓💐

One graduated PRE-K, and one completed 1st GRAD! ✏️

This morning, we started the day with their school’s annual End-of-the-Year Celebration—a special concert where the students sang for us, followed by certificates from their wonderful teachers. It was such a sweet way to celebrate everything they accomplished this year.

The day continued with time at the park, ice cream, and lots of celebrating. 🍦☀️

As proud as I am of what they’ve learned this year, I’m even more proud of the kind, sweet, thoughtful little girls they’re becoming. Their teachers absolutely adore them, and watching them grow in confidence, friendships, and independence has been such a gift.

This past year has been a busy one for me in real estate, and through all the showings, appointments, contracts, and long days, these girls have been some of my biggest supporters. They love hearing about houses, celebrating the wins, and cheering me on—even when they don’t always love sharing mom with work. ❤️

They’ve handled it all with so much grace, and I think that says a lot about who they are.

Now it’s officially summer, and we are ready for all of it: beach days, little adventures, family vacations, baseball weekends and making memories wherever we can squeeze them in between the beautiful chaos of real estate and everyday life. ☀️⚾🏖️

So proud of these girls and so excited for the summer ahead. 💕

Heather Dolan, REALTOR®
Maryland Real Estate
Chesapeake Real Estate Associates, LLC
📲 443-404-4332 | 📞 443-215-HOME
🔗 https://linktr.ee/heatherdolanrealtor

06/16/2026

A few of the homes I’ve been touring with buyers this week… 🏡✨

One thing I love about real estate is that no two buyers are ever looking for the exact same thing.

This week’s tours included everything from peaceful wooded lots and spacious family homes to charming historic properties and homes with room to grow.

Every showing helps narrow the search, refine the wish list, and get one step closer to finding the right fit.

The Eastern Shore continues to offer such a wide variety of homes, lifestyles, and communities—and getting out to explore them is always one of my favorite parts of the job.

Which home would you be stopping to see first? 👀

See something you love? DM me "HOME SEARCH" or text me at + 443-404-4332 for more details.

Heather Dolan, REALTOR®
Maryland Real Estate
Chesapeake Real Estate Associates, LLC
📲 443-404-4332 | 📞 443-215-HOME
🔗 https://linktr.ee/heatherdolanrealtor

06/12/2026

June is all about settling into summer and making the most of the longer days ahead. ☀️🌊🏡

This month’s checklist focuses on keeping your home comfortable, welcoming, and ready for everything summer brings—from backyard cookouts and porch evenings to family visits and days spent on the water.

A few simple seasonal check-ins now can help prevent bigger headaches later, while keeping your home feeling fresh all season long.

✨ Part six of my 2026 monthly home maintenance series. Same simple approach, new seasonal focus each month. Save this one and check back next month for July’s checklist.

Whether you’re planning summer projects, enjoying life along the Chesapeake Bay, or thinking about a future move, I’m always here to help. ☕🏡

Heather Dolan, REALTOR®
Maryland Real Estate
Chesapeake Real Estate Associates, LLC
📲 443-404-4332 | 📞 443-215-HOME
🔗 https://linktr.ee/heatherdolanrealtor

06/10/2026

Turns out some of the skills that help me as a Realtor® started long before real estate. 🪴

I was the kid rearranging my bedroom furniture at 11pm on a Wednesday, constantly redecorating spaces, and somehow always ending up in the home décor aisle.

These days, that same energy gets put toward helping sellers prepare their homes for the market, adding thoughtful staging touches, and helping buyers see a home’s full potential.

It’s probably also why HomeGoods remains one of my favorite places to wander… even when I don’t actually need anything. 🛍️

Some things never change.

Anyone else spend way too much time rearranging their room growing up?

Heather Dolan, REALTOR®
Maryland Real Estate
Chesapeake Real Estate Associates, LLC
📲 443-404-4332 | 📞 443-215-HOME
🔗 https://linktr.ee/heatherdolanrealtor

06/09/2026

Some closings are a little harder than others. ☀️

Over the last several months, I’ve had the privilege of helping Clayton & Katelen through multiple real estate transactions, major life transitions, and the closing of more than one chapter along the way. Now, they’re beginning their next adventure in Florida. 🌴

One of the things I love most about this business isn’t just helping clients buy and sell property—it’s building relationships. Being trusted through important chapters of someone’s life is something I never take for granted.

I put together a few Florida essentials I got from to help them settle into their next adventure. A little something for the road trip, a little something for the beach, and a reminder of how much I’ve enjoyed being part of their journey.

Clayton & Katelen, thank you for your trust, your loyalty, and for allowing me to help guide you through these transitions. Wishing you safe travels, endless sunshine, and so much happiness as you begin this next chapter back in Florida. 🌴☀️

Maryland won’t be quite the same without you both. 🌅🏡

Heather Dolan, REALTOR®
Maryland Real Estate
Chesapeake Real Estate Associates, LLC
📲 443-404-4332 | 📞 443-215-HOME
🔗 https://linktr.ee/heatherdolanrealtor

06/07/2026

A busy week called for a change of scenery. ☀️🌊

With Devin’s baseball tournament nearby this weekend, we decided to turn it into a little family getaway and spend some time in chincoteague island.

The girls have been living their best lives in the pool, we’ve enjoyed some beautiful waterfront views, and for a little while the schedules, phone calls, and never-ending to-do lists have taken a back seat.

One thing I love about living and working in this part of the world is that places like this are never too far away. A little sunshine, time by the water, and extra family time have been exactly what we needed.

I think we’ve already decided we’ll be back later this summer. There’s still so much more to explore, and the girls would happily spend another day in that pool.

Back to baseball tomorrow, but tonight we’re enjoying the view. ⚾️🌊

📍Chincoteague Island, VA

Heather Dolan, REALTOR®
Maryland Real Estate
Chesapeake Real Estate Associates, LLC
📲 443-404-4332 | 📞 443-215-HOME
🔗 https://linktr.ee/heatherdolanrealtor

Address

302 Park Row
Chestertown, MD
21620

Website

https://heatherdolan.chesapeakerealestateassociates.com/

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