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.

06/08/2026

Honored to be recognized as a 2026 RealTrends Verified agent among the top real estate professionals in the country.

Very grateful to my clients, friends, family, and referral partners for the continued trust and support. Every transaction and relationship has helped build my business here on Maryland’s Eastern Shore.

Proud to represent TTR Sotheby’s International Realty and looking forward to what’s ahead.

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

06/05/2026

COMING SOON in Queenstown, MD

Some waterfront homes check the boxes.

Others leave an impression the second you pull into the driveway.

2800 Bennett Point Road blends clean modern design with relaxed Eastern Shore living—expansive water views, soaring ceilings, incredible entertaining spaces, and outdoor areas designed for long summer evenings by the water.

This is a special one.

Coming soon with TTR Sotheby’s International Realty.

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

If you’ve been considering a move to Maryland’s Eastern Shore, send me a message.

Courtney Chipouras | Eastern Shore Realtor | Follow me

06/04/2026

COMING SOON | Queenstown, MD

Some homes are impressive on paper. Others make you stop the moment you pull into the driveway.

2800 Bennett Point Road is one of those properties.

The water views, soaring ceilings, modern architecture, incredible outdoor spaces, and thoughtful design details all come together in a way that feels relaxed, elevated, and very “Eastern Shore.”

• Nearly 18 private acres on Greenwood Creek
• Over 6,000 square feet including a finished basement
• 180 degree, protected Western-facing views

This is the kind of waterfront home buyers wait for.

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

Message me if you’d like more details before it officially hits the market.

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

06/01/2026

UNDER CONTRACT 🏛️🍦🍬

A piece of Rock Hall history will be getting its next chapter soon.

The original Durding’s and adjacent Meyers Store at 5742 & 5746 Main Street are officially under contract. Originally opened by the Durding family in 1875, the store served generations of locals and visitors as a pharmacy, soda fountain, candy & ice cream shop, and gift store over the years.

Even more fascinating? The building was once home to Rock Hall’s first apothecary, owned by Alpheus Sharp—one of the co-founders of Merck Sharp & Dohme Corp. (now Merck).

Walking through the property feels like stepping back in time. Historic artifacts, old memorabilia, and so many stories still remain inside these walls.

Excited for my clients and looking forward to seeing them bring this iconic Main Street property back to its former glory. Small towns need people willing to preserve their history—and this one is worth preserving.

Rock Hall never ceases to surprise me. ⚓️

Courtney Chipouras | Eastern Shore Realtor Follow me

05/27/2026

There’s always more happening behind a successful sale than what shows up in the final numbers.

For this one, we focused on a thoughtful pricing strategy, strong positioning, and consistent communication from day one—and the result was multiple offers and a sale well above asking.

I’m incredibly grateful for clients who place their trust in me and allow me to guide the process from start to finish.

Barbara--Thank you for the kind words and congratulations again on a fantastic outcome.

If you’ve been wondering whether now is the right time to sell, I’m always happy to talk strategy.

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

05/24/2026

🏡 Coming Soon in Gibson’s Grant
232 Evelyne Street, Chester, MD

Situated on one of the largest lots in this sought-after Kent Island community, this 4BR | 3.5BA home offers the space and flexibility that can be hard to find.

Inside, you’ll find high ceilings, an open layout, oversized kitchen opening to the family room, and a separate office on the main level. Upstairs includes a spacious primary suite with sitting area, walk-in closet, and en-suite bath, plus three additional bedrooms and two full baths.

Need room to expand? The unfinished walkout basement already includes a rough-in for a future bath.

Outside, enjoy a fenced backyard with a patio and built-in fire pit—ready for summer evenings and fall gatherings alike.

Residents of Gibson’s Grant enjoy a pool, clubhouse, fitness center, walking trails, community pier, picnic area, and kayak launch—all just 5 minutes to the Bay Bridge.

Reach out if you’d like details before this one officially hits the market.

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

05/22/2026

SOLD! 🥳 204 Overture Way is officially closed—and this one never even hit the open market.

A turn-key home + the right preparation + the right buyer = a smooth, successful sale. Even with more inventory in Symphony Village, standout homes are still creating urgency—especially when buyers can step right in and start enjoying Eastern Shore living from day one.

This one is proof that Centreville buyers are still paying attention—they’re just being selective.

Congratulations to my sellers and welcome home to the buyers. 🏡

If you’re wondering whether now is the right time to list, my answer is: it depends… but strategy matters more than ever. DM me.

Courtney Chipouras | Eastern Shore Realtor | Follow me

05/15/2026

Two opportunities to tour homes in Waterman’s Estates this Saturday 🏡

Join us from 11am–1pm for a collaborative open house event hosted by TTR Sotheby’s International Realty and Rock Hall Properties.

📍 21103 Striper Run — listed by Courtney Chipouras, TTR Sotheby’s International Realty
Now priced below $300K, this updated home offers incredible value in Rock Hall with recent improvements (new roof, heat, & central AC) already completed so you can settle in before summer.

📍 5807 Blue Claw Court — listed by Cindy Genther, Rock Hall Properties
A beautifully maintained coastal-style home offering spacious living areas, an open layout, and easy access to everything in Rock Hall.

Whether you’re looking for a weekend retreat, investment property, or full-time Eastern Shore home, this is the perfect chance to compare two homes in one neighborhood.

Stop by, say hello, and spend your Saturday in Rock Hall.

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

https://www.sothebysrealty.com/ttrsir/eng/sales/detail/766-l-2106-mdke2006218/5807-blue-claw-court-rock-hall-md-21661

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

http://www.mychesapeakehome.com/

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