Courtney Chipouras

Easton MD

TTR Sotheby's International Realty

151 Closed Sales

$108.6M Total Value

$11.3K - $4.7M Price Range

$719.4K Average Price

Prior five years

About Courtney

I’m an Eastern Shore native and Vice President with TTR Sotheby’s International Realty, bringing both local insight and business expertise to every client relationship. Before entering real estate in 2017, I spent nearly two decades in corporate sales and negotiation, experience that now helps me market homes effectively and advocate for my clients with confidence. Whether you’re buying your first home on the Eastern Shore, searching for a waterfront retreat, or preparing to sell, I’ll listen carefully, understand your goals, and provide clear guidance every step of the way. If you’re looking for an agent who combines sharp market knowledge with genuine care, I’d love to help you make your next move.

Home Types: House, Lot/Land, Townhouse, Manufactured, Commercial

Years of Experience: 8

Education: MBA- Wilmington University BA- Salisbury University

Transaction History

1 Year
2 Year
5 Year

Seller Deals

Total Deals

Total Value

$14,318,200

Average Sale Price

$842,247

Price Range

$68K - $3.4M

Buyer Deals

Total Deals

Total Value

$6,692,148

Average Sale Price

$557,679

Price Range

$356K - $1.1M

1 Year View by Quarter

Seller Deals

Total Deals

Total Value

$28,588,600

Average Sale Price

$866,321

Price Range

$68K - $3.4M

Buyer Deals

Total Deals

Total Value

$19,135,138

Average Sale Price

$659,832

Price Range

$145K - $2.4M

2 Year View by Quarter

Seller Deals

Total Deals

Total Value

$47,736,100

Average Sale Price

$734,402

Price Range

$11K - $4.7M

Buyer Deals

Total Deals

Total Value

$60,889,170

Average Sale Price

$708,014

Price Range

$37K - $4.1M

5 Year View

Neighborhoods Courtney Has the Most Experience In

Queenstown

16 Sales
Chestertown

8 Sales
Easton

5 Sales
Centreville

4 Sales
Grasonville

4 Sales
Chester

4 Sales

Courtney's Active Listings

$369,900
- 3 Beds
- 2 Baths
- 1,851 Sq Ft
221 Old Bridge Rd

Chestertown, MD
Coming Soon! Charming American Foursquare on a half-acre corner lot, just one block from the Chester River on the Queen Anne's County side of Historic Chestertown. The home features a welcoming front porch, 3 bedrooms, 2 full baths, an office on the main level, hardwood floors, and many original details. Recent updates include a new upstairs bathroom, new electric panel, and a 2-year-old roof.

Courtney Chipouras TTR Sotheby's International Realty

$264,900
- 2 Beds
- 1 Bath
- 1,110 Sq Ft
24415 Chestertown Rd

Chestertown, MD
Minutes from the heart of Chestertown and a short drive to Rock Hall, this 2-bedroom, 1-bath home offers the perfect balance of small-town convenience and peaceful countryside living. Inside, you’ll find warm hardwood floors and an unfinished basement—ideal for storage, a home gym, or even your future office space. Outside, the large, level yard provides plenty of room to garden, play, or simply

Courtney Chipouras TTR Sotheby's International Realty

$590,000
- 3 Beds
- 2 Baths
- 1,836 Sq Ft
205 Piney Point Landing

Grasonville, MD
Nestled on a private cul-de-sac peninsula in the highly desirable Prospect Bay community, this 3-bedroom, 2-bath rancher offers water views from both the front and back. From the front, enjoy tranquil vistas of Little Greenwood Creek, while the backyard looks out to scenic Prospect Bay. Set on a full acre, this home features a single-level layout ready for your personal touch. The primary suite

Courtney Chipouras TTR Sotheby's International Realty

$100,000
- Land
- 25 Acres
- $4,000 per Acre
0 Grange Hall Rd

Unit MDQA2013276

Centreville, MD
Wooded lot. No perc. Ideal for hunting. Located between Stafford Road and Poplar School Road. Contact Queen Anne's County for additional information on possible use and right of way access.

Courtney Chipouras TTR Sotheby's International Realty

$5,900,000
- 6 Beds
- 4.5 Baths
- 4,214 Sq Ft
5135 Crosby Rd

Rock Hall, MD
A true sportsman’s paradise and a family compound, this impressive 212 +/-acre farm offers breathtaking water views and unparalleled outdoor recreation. The solidly built, colonial style home is designed to capture the beauty of Davis Creek from nearly every room. The kitchen and dining area are perfectly positioned for waterfront entertaining, seamlessly flowing into the family room with gas

Courtney Chipouras TTR Sotheby's International Realty

$5,900,000
- 6 Beds
- 4.5 Baths
- 4,214 Sq Ft
5135 Crosby Rd

Rock Hall, MD
A true sportsman’s paradise and a family compound, this impressive 212 +/-acre farm offers breathtaking water views and unparalleled outdoor recreation. The solidly built, colonial style home is designed to capture the beauty of Davis Creek from nearly every room. The kitchen and dining area are perfectly positioned for waterfront entertaining, seamlessly flowing into the family room with gas

Courtney Chipouras TTR Sotheby's International Realty

$799,900
- 5 Beds
- 3 Baths
- 1,660 Sq Ft
21736 Sunnyside Ave

Rock Hall, MD
This 3-bedroom, 2-bath home with office offers the perfect blend of privacy and waterfront living. Raised above the flood plain and surrounded by mature landscaping, the property feels like a true retreat.The great room boasts vaulted ceilings, a wall of windows with sweeping Grays Inn Creek views, and one of two propane fireplaces. Outdoor living shines with a covered porch and outdoor

Courtney Chipouras TTR Sotheby's International Realty

$1,070,000
- 5 Beds
- 3.5 Baths
- 2,174 Sq Ft
4938 Huntingfield Rd

Rock Hall, MD
Nestled on .83 acres, this captivating Chesapeake Bay waterfront home offers the perfect blend of comfort and coastal charm just outside of Rock Hall. The property includes a 3-bedroom plus bonus room, 2 1/2-bath main house and a detached garage with a 1-bedroom, 1-bath efficiency apartment, ideal for guests or potential rental use. Step inside to be welcomed by a stunning wall of windows

Courtney Chipouras TTR Sotheby's International Realty

Agent License: Maryland #666505

Courtney Chipouras

(667) 243-8103

Courtney Chipouras

About Courtney

Transaction History

Seller Deals

Buyer Deals

Production Over Time

1 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

2 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Courtney Has the Most Experience In

Courtney's Listings and Deals

Courtney's Active Listings