Courtney Chipouras, TTR Sotheby’s International Realty

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

NEW PRICE: Now $320,000If you’ve been looking for an easy Eastern Shore getaway in Rock Hall, 20705 Wilkins Avenue just ...
09/24/2026

NEW PRICE: Now $320,000

If you’ve been looking for an easy Eastern Shore getaway in Rock Hall, 20705 Wilkins Avenue just got a little more attractive.

This charming 4-bedroom cottage has been updated throughout and offers a screened porch, spacious yard, fire pit area and the option to purchase completely furnished—making it easy to start enjoying Rock Hall right away.

Close to restaurants, marinas, Main Street and Ferry Park Beach.
�Full-time home, weekend getaway or potential short-term rental

4 bedrooms, 1 bath31 acres

https://mychesapeakehome.com/listings/20705-wilkins-avenue-rock-hall-md-21661/?utm_source=facebook&utm_medium=social&utm_campaign=20705-wilkins-listing

Want to take a look? Send me a message to schedule a showing.

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

09/22/2026

A new price for a property that’s anything but ordinary.

2800 Bennett Point Road, Queenstown is now offered at $4,695,000.

Nearly 18 private acres. Approximately 1,400 feet of shoreline on Greenwood Creek. Western-facing views 🌅. A pier with 2 boat lifts. Private beach. Pool. An architect-designed home created to take full advantage of its incredible setting.

This is the kind of Eastern Shore property that gives you room to gather everyone you love, spend your days on the water, and stay awhile.

Maybe forever. 🤍

https://mychesapeakehome.com/listings/2800-bennett-point-rd-queenstown-md/?utm_source=facebook&utm_medium=social&utm_campaign=bennett-point-listing

DM me for more information or to schedule a private tour today.

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

09/18/2026

What if you could take in sunset every night from your own backyard? 🌅

Just five minutes from town, 21728 Sunnyside Avenue offers a private half-acre on Grays Inn Creek with protected western views, a private pier and 3–4 feet MLW.

And this isn’t a waterfront home that comes with a huge to-do list. Over the past six years, the sellers have updated the roof, siding, HVAC, kitchen, main-level bathroom, flooring, appliances and more.

The best part might be how easy it is to enjoy—whether you’re looking for a full-time home or a weekend place where you can keep the boat out back and head for the Chester River whenever you feel like it.

3 bedrooms, 2 baths, .5 acres�21728 Sunnyside Ave, Rock Hall, Maryland

Contact me to schedule a showing.

https://mychesapeakehome.com/listings/21728-sunnyside-ave-rock-hall-md-21661/?utm_source=facebook&utm_medium=social&utm_campaign=sunnyside-ave-listing

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

New waterfront listing in Rock Hall 🌅21728 Sunnyside Avenue sits on a private half-acre along Grays Inn Creek, just five...
09/17/2026

New waterfront listing in Rock Hall 🌅

21728 Sunnyside Avenue sits on a private half-acre along Grays Inn Creek, just five minutes from town. With protected western-facing views, 3–4 feet MLW and a private pier, it’s a great setup for anyone who wants to spend more time on the water—and less time maintaining a large property.

The home has had a long list of updates over the past six years, including the roof, siding, HVAC, kitchen, main-level bathroom, flooring, appliances and improvements to the pier. And the water views? You get them from the living room, dining area and main bedrooms.

From here, you can easily boat out to the Chester River and on to Chestertown, Kent Narrows or Rock Hall.

3 bedrooms, 2 bathrooms, .5 acres, $625,000

If you’ve been looking for an affordable waterfront option near Rock Hall, this one is worth a look. Send me a message to schedule a showing.

https://mychesapeakehome.com/listings/21728-sunnyside-ave-rock-hall-md-21661/?utm_source=facebook&utm_medium=social&utm_campaign=sunnyside-ave-listing

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

Clients apologize to me all the time for things they absolutely do not need to apologize for.Asking a million questions....
09/16/2026

Clients apologize to me all the time for things they absolutely do not need to apologize for.

Asking a million questions. Wanting to see a house a second time. Changing their mind. Taking their time. Texting me about a listing they just found.

Buying a home is a big decision. You should ask questions. You should take the time you need. You definitely shouldn’t feel pressured to buy a house that isn’t right for you.

My job is to give you good advice, answer your questions, point out the things you may not have considered, and help you make a decision you feel good about.

So if you’re thinking about buying in Kent, Queen Anne’s or Talbot County—or anywhere along Maryland’s Eastern Shore—reach out. I’m always happy to talk through what you’re looking for and where to start.

No apology required. 😉

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

09/10/2026

What if the beach was just two blocks from home? ⚓

At 20705 Wilkins Avenue, you’re an easy walk or bike ride from Ferry Park Beach, Main Street, restaurants, marinas and everything that makes Rock Hall such a fun place to spend a weekend—or a lot more time.

The 4-bedroom cottage has seen a number of recent updates and is being offered fully furnished, making it easy to move right in and start enjoying it. There’s also a screened porch, updated outdoor space with a fire pit, and a .31-acre lot.

Full-time home, weekend getaway or investment property—there are plenty of possibilities here.

https://mychesapeakehome.com/listings/20705-wilkins-avenue-rock-hall-md-21661/?utm_source=facebook&utm_medium=social&utm_campaign=20705-wilkins-listing

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

NEW PRICE | $825,000 🏡If you’ve had your eye on 232 Evelyne Street in Gibson’s Grant, now may be the time to take anothe...
09/04/2026

NEW PRICE | $825,000 🏡

If you’ve had your eye on 232 Evelyne Street in Gibson’s Grant, now may be the time to take another look.

Recently reduced to $825,000, this light-filled 4-bedroom, 3.5-bath home offers an open floor plan and a great location within one of Kent Island’s sought-after waterfront communities.

Gibson’s Grant offers a community pool, clubhouse, fitness center, waterfront pavilion, fishing pier, kayak launch, walking trails and more. Just 5 minutes from the Bay Bridge.

📍 232 Evelyne Street, Chester, MD�💰 Now offered at $825,000

Want to see it in person? Send me a message to schedule a showing.

https://mychesapeakehome.com/listings/232-evelyne-st-chester-md/?utm_source=facebook&utm_medium=social&utm_campaign=evelyne-st-listing

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

NEW PRICE | $1,500,000Blue Heron Oyster House & Inn in Rock Hall just had a significant $195,000 price adjustment.The sa...
09/04/2026

NEW PRICE | $1,500,000

Blue Heron Oyster House & Inn in Rock Hall just had a significant $195,000 price adjustment.

The sale includes both the real estate AND the established business, offering a buyer the opportunity to step into a completely renovated, turnkey restaurant with a loyal following in the heart of Rock Hall.

The property also includes four inn rooms that are not currently being rented—creating an opportunity for an additional revenue stream.

Now offered at $1,500,000.

And because this question always comes up: Blue Heron is NOT closing. The owners are simply ready to retire.

Interested in learning more? Send me a DM for details. Financials and FF&E information are available to qualified buyers with a signed NDA.

https://mychesapeakehome.com/listings/20658-wilkins-ave-rock-hall-md-21661/?utm_source=facebook&utm_medium=social&utm_campaign=wilkins-ave-commercial-listing

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

Address

17 Goldsborough Street
Easton, MD
21601

Telephone

+14102001224

Website

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