Associate Broker (MD: 517740)
28 years experience
Queen Annes County, Maryland represents one of the Eastern Shore's most dynamic real estate markets, where historic charm meets modern waterfront living. With 288 actively licensed real estate agents serving this diverse county, the market reflects a sophisticated blend of agricultural properties, waterfront estates, and suburban developments that attract buyers from across the Mid-Atlantic region.
The county's unique position between the Chesapeake Bay and Delaware River creates distinct micro-markets that require specialized local knowledge. All 288 licensed agents maintain email connectivity, reflecting the market's embrace of digital communication tools essential for serving both local residents and out-of-state buyers seeking Eastern Shore properties.
Centreville anchors the county as its seat of government and commercial hub, featuring a mix of historic homes and newer developments that appeal to families and retirees alike. Stevensville has emerged as a particularly sought-after market, benefiting from its proximity to the Bay Bridge and easy access to Annapolis and Baltimore, making it popular among commuters seeking waterfront lifestyles without urban price tags.
The Chester and Kent Island areas represent the county's premium waterfront markets, where luxury properties command top dollar for Chesapeake Bay access and stunning water views. Meanwhile, smaller communities like Queenstown and Grasonville offer more affordable entry points into the county's desirable school districts and recreational amenities, creating diverse opportunities across different price segments.
Queen Annes County's real estate landscape defies simple categorization, with agricultural preservation areas, established neighborhoods, and waterfront enclaves creating vastly different pricing structures within short distances. Properties can range from modest inland homes under $300,000 to multi-million dollar waterfront estates, requiring agents to understand multiple market segments and buyer demographics simultaneously.
Seasonal fluctuations play a significant role in market activity, with waterfront properties experiencing peak interest during spring and summer months when buyers can fully appreciate the county's recreational assets. The market has shown remarkable resilience, benefiting from Maryland's strong economy and the growing trend of remote work enabling more buyers to prioritize lifestyle over proximity to urban employment centers.
Real estate service providers, from mortgage lenders to home inspectors, find Queen Annes County's agent network essential for building referral relationships in this geographically dispersed market. The county's 288 agents represent valuable connections to affluent buyers and sellers who typically require comprehensive service packages, making these relationships particularly lucrative for complementary businesses.
Marketing companies and PropTech firms particularly benefit from direct agent contact data, as Queen Annes County's mix of luxury waterfront properties and traditional suburban homes creates demand for diverse marketing approaches and technological solutions. These agents serve clients ranging from first-time homebuyers to high-net-worth individuals seeking vacation properties, requiring sophisticated tools and services that justify premium pricing structures.
As of 2/17/2026, Tom Boeshore has 2 properties for sale in Chester and surrounding areas.
$79,900
Listed 2025-05-29
$189,900
Listed 2025-05-29
Tom Boeshore currently has no rental properties available in Chester and surrounding areas. Check back later.