Courtney Chipouras, TTR Sotheby’s International Realty

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Courtney Chipouras, TTR Sotheby’s International Realty

Courtney Chipouras REALTOR® is an Eastern Shore Native and Vice President at TTR Sotheby’s International Realty.

08/25/2026

$5,000 toward closing costs in Rock Hall! 🏡

The sellers of 21103 Striper Run are now offering $5,000 in closing cost assistance with an acceptable offer—giving buyers a little extra flexibility to make this home their own.

Offered at $299,900, this 3-bedroom, 2.5-bath townhome features 1,628 square feet, a garage, and low-maintenance living close to Main Street, marinas, restaurants and the beach. A new roof, heat and central air were also installed this spring.

Whether you’re looking for a full-time home or a weekend place in Rock Hall, this is a good time to take another look.

https://mychesapeakehome.com/listings/21103-striper-run-rock-hall-md/

Contact me to schedule a showing or learn more.

Courtney Chipouras
TTR Sotheby’s International Realty
(410) 200-1224 Mobile
(410) 673-3344 Office
[email protected]
mychesapeakehome.com

08/24/2026

Blue Heron Oyster House & Inn is for sale—but it is NOT closing. 🦪

This is an opportunity to purchase an established Rock Hall restaurant along with the real estate.

Since opening in 2022, Blue Heron has built a loyal following with both locals and visitors. The property was completely renovated inside and out in 2022 and includes:

• 4,000+ square feet
• Indoor and outdoor dining + bars
• Seating for approximately 147 during the season
• Commercial kitchen and extensive cold storage
• FF&E less than five years old
• Three upstairs inn rooms that are not currently being rented
• 24 on-site parking spaces plus overflow on Coleman Rd & Rt. 20

The restaurant is open and operating as usual. The owners are simply ready to retire and pass the business on to its next owner.

Qualified buyers can receive additional business information and a complete FF&E inventory after signing an NDA.

Full details: mychesapeakehome.com/listings/20658-wilkins-ave-rock-hall-md-21661/

Interested—or know someone who might be? Send me a DM.

Courtney Chipouras
TTR Sotheby’s International Realty
(410) 200-1224 Mobile
(410) 673-3344 Office
[email protected]
mychesapeakehome.com

08/20/2026

OPEN HOUSE
SATURDAY, AUGUST 22ND
10 AM–12 PM

If you’ve been considering a move to Kent Island, stop by 232 Evelyne Street in Chester this Saturday and take a look around.

Located in Gibson’s Grant, this 4-bedroom, 3.5-bath home offers 3,312 square feet of living space in one of Kent Island’s most sought-after communities.

📍 232 Evelyne Street, Chester, MD�
📅 Saturday, August 22�
⏰ 10 AM–12 PM�
💰 Offered at $840,000

Come see the home—and the neighborhood—for yourself.

Full listing details: https://mychesapeakehome.com/listings/232-evelyne-st-chester-md/

Courtney Chipouras
TTR Sotheby’s International Realty
(410) 200-1224 Mobile
(410) 673-3344 Office
[email protected]
mychesapeakehome.com

08/18/2026

Comment LISTING and I’ll send you everything you need to know.

Think modern, waterfront living on nearly 18 acres with 180 degree western-facing views.

Life in this home looks like:
Morning coffee looking out your oversized windows that make you feel as you’re one with nature.
Cooking in a kitchen designed for real use, not just photos.
Working, relaxing, and gathering with a layout that actually supports your day.
A primary suite that is its own private wing.
Evenings on the screened-in porch watching sunset over Greenwood Creek and the Eastern Bay.
Privacy, calm, and space within minutes of Kent Island conveniences.

Located on the Bennett Point peninsula, this home offers the lifestyle buyers hope to find when they wait for the right property in Queenstown, MD.

Just 30 minutes to Easton airport, 1 hour to BWI and DCA, and under 2 hours from PHL.

Comment LISTING and I’ll send you all the information.

Courtney Chipouras | Eastern Shore Realtor | Follow me Courtney Chipouras - Eastern Shore Realtor®

08/17/2026

JUST SOLD | 246 Upland Lane, Centreville

Some buyers find the right house quickly. For this family, it took more than a year—and I’m so glad they waited for the one that felt right.

We closed on this 4-bedroom Centreville home for $624,900. I was also able to negotiate a $15,000 seller credit for my buyers.

I really enjoyed getting to know this family throughout the process. The review they left me after closing was one of those that makes you remember why you do this:

“Courtney went above and beyond to help our family find the right house to grow into! She stuck with us for OVER A YEAR, never once trying to push us to buy something that wasn’t a good fit and always giving the best advice.”

In a challenging housing market, sometimes the best advice is simply not to force it. We kept looking, stayed on top of new and coming-soon listings, and waited until the right opportunity came along.

Very happy for this family as they settle into their new home!

Courtney Chipouras
TTR Sotheby’s International Realty
(410) 200-1224 Mobile
(410) 673-3344 Office
[email protected]
mychesapeakehome.com

08/14/2026

Did you spend Pirates & Wenches Weekend in Rock Hall and think, “I could get used to this…”? 🏴‍☠️⚓

You might want to take a look at 21103 Striper Run.

This 3-bedroom, 2.5-bath townhome offers low-maintenance living close to Main Street, marinas, restaurants and the beach—with a garage for the golf cart and boating gear, plus a new roof, heat and central air installed this spring.

Offered at $299,900, it could be a full-time home or weekend escape—a very good excuse to spend a lot more time in Rock Hall.

Ready to come back to look at real estate? Send me a DM to schedule a showing.

https://mychesapeakehome.com/listings/21103-striper-run-rock-hall-md/

Courtney Chipouras
TTR Sotheby’s International Realty
(410) 200-1224 Mobile
(410) 673-3344 Office
[email protected]
mychesapeakehome.com

08/13/2026

If you’re looking for more space on Kent Island without giving up convenience, 232 Evelyne Street is worth a closer look.

Located on one of the larger lots in Gibson’s Grant, this 4-bedroom home offers more than 3,300 square feet, a dedicated home office, spacious primary suite, fenced backyard with patio and fire pit, plus an unfinished walkout basement with plenty of potential.

And the neighborhood is a big part of the appeal—pool, clubhouse, fitness center, walking trails, community pier and kayak launch, all just about five minutes from the Bay Bridge.

📍 232 Evelyne Street | Chester
4 Bedrooms | 3.5 Baths | 3,312 Sq. Ft.
Offered at $840,000

https://mychesapeakehome.com/listings/232-evelyne-st-chester-md/

Take a closer look or contact me to schedule a showing.

Courtney Chipouras
TTR Sotheby’s International Realty
(410) 200-1224 Mobile
(410) 673-3344 Office
[email protected]
mychesapeakehome.com

08/07/2026

Kind of chic… to live in a home that feels just as relevant today as it will 20 years from now.

Modern architecture has always been about thoughtful design, clean lines, and a connection to the landscape. At 2800 Bennett Point Road, floor-to-ceiling glass, western waterfront views, and seamless indoor-outdoor living make the setting just as important as the home itself.

Some homes follow trends. Others quietly stand apart.

📍Queenstown, Maryland
18± acres • Approx. 1,400’ of shoreline • Offered at $4,995,000

DM me for details…

Courtney Chipouras | Eastern Shore Realtor | Follow me Courtney Chipouras - Eastern Shore Realtor®

Address

17 Goldsborough Street
Easton, MD
21601

Telephone

+14102001224

Website

http://www.mychesapeakehome.com/

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