```html ```
top of page

HOME OF THE CHESAPEAKE REGION'S BEST AGENTS

  • Facebook
  • Instagram
  • LinkedIn
  • Spotify
  • TikTok
  • X
  • Youtube
Housecats Logo
Housecats Company

Eastern Shore

Waterfront towns and rural landscapes defined by heritage, privacy, and second-home appeal.

The Eastern Shore is characterized by waterfront towns, agricultural landscapes, and a slower, more intentional pace of life. Buyers are often motivated by lifestyle considerations, privacy, and long-term ownership, including second-home purchasers and those seeking an alternative to more densely populated markets. Real estate activity in the region reflects a strong connection to place and a preference for quality over speed.

Eastern Shore | 2025 Annual Market Report

2025 ANNUAL MARKET REPORT

Eastern Shore | 2025 Annual Market Report

Eastern Shore | 2024 Annual Market Report

2024 ANNUAL MARKET REPORT

Eastern Shore | 2024 Annual Market Report

annual market reports

A comprehensive look at pricing, demand, and market dynamics across the region

Eastern Shore | Q4 2025 Market Update

Q4 2025 MARKET UPDATE

Eastern Shore | Q4 2025 Market Update

Eastern Shore | Q3 2025 Market Update

Q3 2025 MARKET UPDATE

Eastern Shore | Q3 2025 Market Update

Eastern Shore | Q2 2025 Market Update

Q2 2025 MARKET UPDATE

Eastern Shore | Q2 2025 Market Update

Quarterly market reports

Timely updates that track market direction, buyer behavior, and emerging trends

Eastern Shore

SNAPSHOT

The snapshot below outlines overall residential market performance on the Eastern Shore, offering perspective on pricing, demand, and sales activity throughout the year.

Eastern Shore | 2025 Annual Market Report

$1,138,196,858

TOTAL SALES VOLUME

1,704

TOTAL TRANSACTIONS

$507,097

MEDIAN sales price

26

MEDIAN days on mkt

Eastern Shore | 2025 Annual Luxury Market Report

luxury markets

Luxury activity on the Eastern Shore in 2025 was closely tied to lifestyle-driven demand and long-term ownership goals. High-end buyers approached the market with patience, often prioritizing unique settings, privacy, and quality over transactional speed.


As demand strengthened in the latter half of the year, the luxury segment reflected renewed confidence, particularly for properties that delivered a clear sense of place. This behavior reinforced the Shore’s role as a destination market, where luxury is defined less by price alone and more by experience, setting, and longevity.

210

SALES IN

2025

$1,954,466

AVERAGE PRICE IN

2025

44

AVERAGE DOM IN

2025

Figures reflect full-year closed sales from the most recent annual market report.

waterfront markets

Waterfront real estate on the Eastern Shore in 2025 remained closely tied to lifestyle aspiration and long-term ownership goals. Buyers approached the market with intention, often prioritizing privacy, setting, and connection to the land and water over speed of execution.


As market conditions strengthened later in the year, waterfront properties that aligned with these priorities attracted renewed interest, reinforcing the Shore’s reputation as a destination market. Transactions reflected a balance between patience and conviction, underscoring the region’s sensitivity to demand shifts against a backdrop of limited and distinctive inventory.

Eastern Shore | 2025 Annual Waterfront Market Report

285

SALES IN

2025

$1,513,516

AVERAGE PRICE IN

2025

29

AVERAGE DOM

2025

Figures reflect full-year closed sales from the most recent annual market report.

buyer behavior

A closer look at how buyers are navigating today’s market

Buyer behavior on the Eastern Shore remains closely tied to lifestyle priorities and long-term ownership goals. Many purchasers approach the market with patience, prioritizing quality, privacy, and location over speed. This dynamic often results in longer evaluation periods, particularly for unique or waterfront properties, as buyers focus on fit rather than short-term market fluctuations.

Chestertown

Chestertown

Chestertown blends historic charm with a relaxed pace of life, attracting residents drawn to community, heritage, and a quieter Eastern Shore setting.

Easton

Easton

Easton offers a refined small-town lifestyle with a vibrant arts scene, dining, and everyday convenience, appealing to buyers seeking charm without isolation.

Oxford

Oxford

Oxford delivers a quiet, traditional waterfront lifestyle centered on boating, privacy, and historic architecture, appealing to buyers seeking understated coastal living.

St. Michaels

St. Michaels

St. Michaels is a quintessential waterfront town known for maritime charm, tourism, and long-term lifestyle appeal, attracting both primary and second-home buyers.

Stevensville

Stevensville

Accessible Eastern Shore living with water influence.

Towns & Communities

Each town within the region offers its own character, housing mix, and lifestyle appeal.

Explore local market snapshots to see how individual communities fit within the broader regional landscape.

Favicon.png

Whether you’re buying, selling, or simply staying informed, a deeper look

at your specific town or property type can provide valuable perspective.

More Than Real Estate.

It’s How You Live Here.

Buying or selling a home is just the start.

What matters is understanding the place around it — the market, the lifestyle, the culture, the communities, and the forces shaping what comes next.

That’s what we do.

HOUSECATS (20).png

2077 Somerville Rd

Annapolis, MD 21401

Favicon.png
bottom of page