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Courtney Chipouras

Courtney Chipouras
Real Estate Agent (Salesperson)
Easton MD

Salesperson (MD: 666505)

9 years experience

REALTOR® 5 Active Listings Serves Talbot County, MD
View on Realtor.com

Contact Information

Brokerage
Ttr Sotheby's International Realty

Office Website
Office Address
17 Goldsborough St
Easton, MD  21601
(Talbot County)
Office Phone
410-673-3344
Office Fax
Mobile
410-200-1224
Email
cour****@****************.com
Show Email for $5

About Courtney Chipouras

**Courtney Chipouras - Realtor® / MBA / RSPS - Resort & Second Home Specialist**

Courtney Chipouras, a native of the Eastern Shore, brings a wealth of experience to Benson & Mangold after a successful 19-year career as a top producer in a prominent global communications and technology firm. With real estate deeply rooted in her family—her mother, aunt, and uncle all held Realtor licenses—Courtney possesses an innate understanding of the industry. Her extensive exposure to various properties, from historic homes to new constructions, has honed her keen eye for design, further enhanced by her recent venture into renovating her own fixer-upper.

A graduate of Salisbury University, where she was a member of the varsity tennis team, Courtney also earned her MBA in Marketing from Wilmington University. She and her husband currently reside on the Eastern Shore. Committed to community service, she serves on the board of Rebuilding Together Kent County and the Queen Anne's Mental Health Committee. In her leisure time, Courtney enjoys traveling, golfing, and fishing whenever she can.

Talbot County, MD Real Estate Market Analysis (Single Family Homes)

$1,226,137
Avg. Listing Price
From Courtney's portfolio
3.5 / 3.0
Avg. Beds/Baths
Typical property size
2,864 sf
Avg. Square Footage
Interior living space
246
Active Listings
Current inventory

Talbot County, Maryland represents one of the Eastern Shore's most distinctive real estate markets, where waterfront properties and historic charm create a unique investment landscape. The county's real estate sector is supported by 362 total actively licensed agents, all of whom maintain current email contact information, reflecting a highly connected and professional agent network that serves this specialized market.

What makes Talbot County particularly intriguing is its blend of luxury waterfront estates along the Chesapeake Bay and more affordable inland properties, creating diverse opportunities for both investors and homebuyers. The market here operates with a level of sophistication that belies the county's rural character, driven largely by proximity to major metropolitan areas and the enduring appeal of Eastern Shore living.

Major Talbot County, Maryland Real Estate Markets

Easton serves as the county seat and primary commercial hub, featuring a mix of historic downtown properties, suburban developments, and executive homes that attract professionals commuting to Baltimore and Washington D.C. The town's strategic location and cultural amenities, including the Academy Art Museum and numerous festivals, have made it increasingly attractive to buyers seeking small-town charm with metropolitan accessibility.

St. Michaels and Oxford represent the county's premium waterfront markets, where historic maritime villages command some of Maryland's highest property values outside of major metropolitan areas. These communities attract second-home buyers, retirees, and investors drawn to the combination of Chesapeake Bay access, preserved colonial architecture, and yacht-friendly harbors that define Eastern Shore luxury living.

Market Dynamics and Geographic Complexity

Talbot County's real estate market operates on distinct seasonal patterns, with waterfront properties experiencing peak activity during spring and summer months when buyers can fully appreciate the maritime lifestyle. The county's geography, characterized by numerous creeks, rivers, and bay frontage, creates micro-markets where waterfront access, view quality, and proximity to marinas significantly impact property values and marketing strategies.

Agricultural preservation easements and historical district regulations add layers of complexity to property transactions, requiring agents with specialized knowledge of conservation programs, zoning restrictions, and renovation guidelines. These factors create opportunities for buyers seeking preserved landscapes and architectural integrity, while also presenting unique challenges that demand experienced local representation.

Why Businesses Need Talbot County, Maryland Agent Contact Data

Real estate service providers, from mortgage lenders to home inspectors, find Talbot County's concentrated agent network particularly valuable for building referral relationships in a market where personal connections drive business success. With all 362 licensed agents maintaining current email addresses, service companies can efficiently reach decision-makers who handle everything from historic home renovations to luxury waterfront transactions.

Property technology companies and investment firms targeting the Eastern Shore market benefit from direct access to agents who understand the nuances of waterfront property marketing, agricultural land sales, and the unique buyer profiles drawn to this region. These agents serve as gatekeepers to a sophisticated market where traditional marketing approaches must be adapted to reflect the county's distinct character and buyer expectations.

Current Property Listings

As of 2/17/2026, Courtney Chipouras has 5 properties for sale in Easton and surrounding areas.

$560,000

Listed 2026-02-14

118 Touhey Dr
Stevensville, MD  21666

Beds: 4.0
Baths: 2.5
Sq Ft: 2,302
Lot: 20,038 sf
Single Family Map
View Full Details

$850,000

Listed 2024-10-30

4938 Huntingfield Rd
Rock Hall, MD  21661

Beds: 4.0
Baths: 3.5
Sq Ft: 2,174
Lot: 36,155 sf
Single Family Map
View Full Details

$5,900,000

Listed 2025-03-17

5135 Crosby Rd
Rock Hall, MD  21661

Beds: 6.0
Baths: 4.5
Sq Ft: 4,214
Lot: 9,273,053 sf
Single Family Map
View Full Details

$725,000

Listed 2026-01-21

1410 Bennett Point Rd
Queenstown, MD  21658

Beds: 5.0
Baths: 3.0
Sq Ft: 2,464
Lot: 89,298 sf
Single Family Map
View Full Details

$310,000

Listed 2026-01-06

21103 Striper Run
Rock Hall, MD  21661

Beds: 3.0
Baths: 2.5
Sq Ft: 1,628
Lot: 5,663 sf
Townhomes Map
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$499,900

Listed 2025-10-24

906 Auckland Way
Chester, MD  21619

Beds: 3.0
Baths: 3.5
Sq Ft: 2,076
Condos Map
View Full Details

Current Property Rentals

Courtney Chipouras currently has no rental properties available in Easton and surrounding areas. Check back later.