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Samantha Grimes

Samantha Grimes
Real Estate Agent (Associate Broker)
Trappe MD

Associate Broker (MD: 535569)

25 years experience

REALTOR® 7 Active Listings Serves Talbot County, MD
View on Realtor.com

Contact Information

Brokerage
Chesapeake Real Estate Associates Llc
Office Address
29349 Maple Ave Ste 7
Trappe, MD  21673
(Talbot County)
Office Phone
410-476-2201
Office Fax
Mobile
410-310-6426
Email
samg*********@*****.com
Show Email for $5

Service Areas

Easton: MD Centreville: MD Price: MD Grasonville: MD Kent Narrows: MD Chester: MD Stevensville: MD

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

$1,226,137
Avg. Listing Price
From Samantha'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, Samantha Grimes has 7 properties for sale in Trappe and surrounding areas.

$384,000

Listed 2025-11-19

24029 Meadows Dr
Ridgely, MD  21660

Beds: 3.0
Baths: 2.0
Sq Ft: 1,792
Lot: 87,120 sf
Single Family Map
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$275,000

Listed 2025-07-29

21245 Tanyard Rd
Preston, MD  21655

Beds: 3.0
Baths: 3.0
Sq Ft: 2,128
Lot: 27,007 sf
Single Family Map
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$464,500

Listed 2026-01-08

208 Grasonville Cemetery Rd
Grasonville, MD  21638

Beds: 3.0
Baths: 2.0
Sq Ft: 2,044
Lot: 32,670 sf
Single Family Map
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$559,000

Listed 2025-11-02

216 Blakefield Dr
Chestertown, MD  21620

Beds: 4.0
Baths: 3.0
Sq Ft: 2,400
Lot: 43,560 sf
Single Family Map
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$940,000

Listed 2025-07-10

Eagle Manor Dr Lot 20
Church Hill, MD  21623

Beds: 5.0
Baths: 3.5
Sq Ft: 0
Lot: 43,560 sf
Single Family Map
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$1,053,900

Listed 2025-05-16

Finley Creek Dr Lot 4
Centreville, MD  21617

Beds: 3.0
Baths: 2.5
Sq Ft: 2,575
Lot: 54,450 sf
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$135,000

Listed 2025-07-10

Eagle Manor Dr
Church Hill, MD  21623

Beds:
Baths:
Sq Ft:
Lot: 43,560 sf
Land Map
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Current Property Rentals

As of 2/17/2026, Samantha Grimes has the following rental properties available in Trappe and surrounding areas.

$3,500

Listed 2026-01-13

151 Hammer Run
Centreville, MD  21617

Beds: 4.0
Baths: 3.0
Sq Ft: 2,517
Lot: 3,267,000 sf
Single Family Map
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