Courtney Chipouras

Easton MD

TTR Sotheby's International Realty

141 Closed Sales

$106.3M Total Value

$37K - $4.7M Price Range

$753.9K Average Price

Prior 5 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, Manufactured, Townhouse, Lot/Land, Commercial

Years of Experience: 9

Education: MBA- Wilmington University BA- Salisbury University

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	19
Total Value	$13,784,200
Average Sale Price	$725,484
Price Range	$68K - $3.4M

Buyer Deals
Total Deals	13
Total Value	$8,252,463
Average Sale Price	$634,805
Price Range	$375K - $1.7M

1 Year View by Quarter

Seller Deals
Total Deals	35
Total Value	$24,855,300
Average Sale Price	$710,151
Price Range	$68K - $3.4M

Buyer Deals
Total Deals	26
Total Value	$17,126,148
Average Sale Price	$658,698
Price Range	$150K - $2.4M

2 Year View by Quarter

Seller Deals
Total Deals	69
Total Value	$52,429,100
Average Sale Price	$759,842
Price Range	$68K - $4.7M

Buyer Deals
Total Deals	72
Total Value	$53,863,870
Average Sale Price	$748,109
Price Range	$37K - $4.1M

5 Year View

Neighborhoods Courtney is Experienced In

Courtney's Active Listings

$5,400,000
- 5 Beds
- 4.5 Baths
- 6,156 Sq Ft
2800 Bennett Point Rd

Queenstown, MD
Coming soon. A unique offering on Maryland’s Eastern Shore, this architect-designed contemporary home sits on nearly 18 private waterfront acres across 2 parcels with 1,400 feet of shoreline along sought-after Greenwood Creek. Thoughtfully designed for seamless indoor-outdoor living, the home features floor-to-ceiling windows, open entertaining spaces, a chef’s kitchen, home theater, billiards

Courtney Chipouras TTR Sotheby's International Realty

$750,000
- 4 Beds
- 4 Baths
- 3,180 Sq Ft
11122 Boyer Ln

Worton, MD
Thoughtfully designed and built in 2017, this private retreat sits on nearly 7 peaceful acres just 5 minutes north of historic Chestertown and 30 minutes from Middletown, Delaware. Surrounded by farmland and mature landscaping, the property offers the perfect balance of modern comfort, flexibility, and quiet Eastern Shore living. The heart of the home is the stunning chef’s kitchen featuring

Courtney Chipouras TTR Sotheby's International Realty

$865,000
- 4 Beds
- 3.5 Baths
- 3,312 Sq Ft
232 Evelyne St

Chester, MD
Situated on one of the largest lots in sought-after Gibson’s Grant, this 4-bedroom, 3.5-bath home offers space, flexibility, and room to grow. High ceilings and an open layout create an airy feel, with an oversized kitchen flowing seamlessly into the family room and a separate main-level office for work or quiet retreat. The main level also features a formal dining room and living room. Upstairs,

Courtney Chipouras TTR Sotheby's International Realty

$299,900
- 3 Beds
- 2.5 Baths
- 1,628 Sq Ft
21103 Striper Run

Rock Hall, MD
Easy, low-maintenance living in the heart of Rock Hall. New roof, heat, and central air in Spring 2026. This updated 3-bedroom, 2.5-bath townhome with garage is perfectly positioned just steps from marinas, Main Street shops, favorite restaurants, and the community beach. Recent improvements include luxury vinyl plank flooring, newer appliances, new roof, heat, central air, and fresh paint

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

Recently Sold

$485,000

Sold May 21, 2026
- 2 Beds
- 2 Baths
- 2,810 Sq Ft
204 Overture Way

Centreville, MD
- $173/SF
- 0 Days On Market
- Current Est. Value $509K
Courtney Chipouras TTR Sotheby's International Realty

$362,000

Sold May 4, 2026
- 3 Beds
- 2 Baths
- 1,358 Sq Ft
5883 Williams St

Rock Hall, MD
- 3% Below List
- $267/SF
- 12 Days On Market
- Current Est. Value $370K
Courtney Chipouras TTR Sotheby's International Realty

$370,000

Sold May 1, 2026
- 3 Beds
- 1.5 Baths
- 1,404 Sq Ft
217 Philosophers Terrace

Chestertown, MD
- 14% Above List
- $264/SF
- 3 Days On Market
- Current Est. Value $336K
Courtney Chipouras TTR Sotheby's International Realty

$370,000

Sold Apr 29, 2026
- 3 Beds
- 2 Baths
- 1,364 Sq Ft
21235 Rock Hall Ave

Rock Hall, MD
- 1% Below List
- $271/SF
- 4 Days On Market
- Current Est. Value $366K
Courtney Chipouras TTR Sotheby's International Realty

$570,000

Sold Mar 13, 2026
- 4 Beds
- 2.5 Baths
- 2,302 Sq Ft
118 Touhey Dr

Stevensville, MD
- 2% Above List
- $248/SF
- 4 Days On Market
- Current Est. Value $568K
Courtney Chipouras TTR Sotheby's International Realty

$725,000

Sold Feb 27, 2026
- 5 Beds
- 3 Baths
- 2,464 Sq Ft
1410 Bennett Point Rd

Queenstown, MD
- $294/SF
- 3 Days On Market
- Current Est. Value $736K
Courtney Chipouras TTR Sotheby's International Realty

$490,000

Sold Feb 19, 2026
- 3 Beds
- 3.5 Baths
- 2,076 Sq Ft
906 Auckland Way

Chester, MD
- $236/SF
- 74 Days On Market
- Current Est. Value $513K
Courtney Chipouras TTR Sotheby's International Realty

$850,000

Sold Feb 17, 2026
- 4 Beds
- 3.5 Baths
- 2,174 Sq Ft
4938 Huntingfield Rd

Rock Hall, MD
- $391/SF
- 432 Days On Market
- Current Est. Value $849K
Courtney Chipouras TTR Sotheby's International Realty

$1,600,000

Sold Dec 23, 2025
- 6 Beds
- 5.5 Baths
- 4,016 Sq Ft
1026 Long Point Rd

Grasonville, MD
- $398/SF
- 48 Days On Market
- Current Est. Value $2M
Courtney Chipouras TTR Sotheby's International Realty

Agent License: Maryland #666505

Courtney Chipouras

(667) 243-8103

Homes for Sale by City

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 is Experienced In

Courtney's Listings and Deals

Courtney's Active Listings

Recently Sold