What $500K Buys You in Chestertown in 2026

If you’re shopping in the $500,000 range on Maryland’s Eastern Shore, Chestertown might be one of the most underrated opportunities in 2026. 

Unlike bridge adjacent areas — where $500K can feel tight — Chestertown offers space, character, and flexibility at this price point. 

Here’s exactly what the data shows right now. 

📊 The Chestertown $500K Snapshot 

Current residential listings unfer $550,000 show: 

• 25 total listings in this range  

• Median list price: $334,000  

• Average list price: $361,756  

• Median price per square foot: $203.65  

• Median property age: 33 years 

 Featured Property: 109 Metcalf Rd, Chestertown, MD 21620 

• Price: $264,900  

• Type: Townhouse / New Construction  

• Beds/Baths: 3 beds | 1.5 baths  

• Size: ~1,280 sq ft  

• Year Built: 2025  

• Lot: ~3,920 sq ft  

• Status: Active for sale  

This brand-new townhome in Chester Arms combines modern construction with affordability — perfect for first-time buyers, investors, or those seeking low-maintenance living in Chestertown’s historic context.  

Features include stainless steel appliances, granite counters, walk-in closets, a covered patio, and no HOA — all at a price point well under half a million.  

📐 How Much Space Do You Get? 

Across all active listings in this price range: 

• Median square footage: 1,666 sq ft  

• Average square footage: 1,758 sq ft  

• Average lot size: ~0.5 acres  

But once you approach the $450K–$525K level, square footage jumps significantly into the 2,400–3,000+ range. 

In many Eastern Shore towns, $500K gets you entry-level waterfront or a smaller home. 

In Chestertown, it often gets you: 

✔️ 4+ bedrooms 
✔️ Newer construction (2004–2010 range) 
✔️ Established neighborhoods 
✔️ Room to grow 

🌊 The Lifestyle Factor 

Chestertown offers: 

• Historic downtown charm 

• Washington College 

• River access 

• Larger lots than many bridge-adjacent towns 

• Less congestion 

If your priority is: 

• Space 

• Value per square foot 

• Quiet Eastern Shore living 

Chestertown stretches your dollar further than most surrounding markets. 

 

💡 The Big Takeaway 

$500K in Chestertown buys: 

More bedrooms. 
More land. 
More flexibility. 
More house. 

It’s one of the few markets where half a million dollars still feels substantial. 

 

Thinking About Buying in Chestertown? 

If you’d like: 

• A curated list of the best homes under $500K 

• A breakdown of which neighborhoods hold value best 

• Or a comparison of Chestertown vs. Kent Island at this price point 

Send us an email and just say “Chestertown.” 

I’ll send you a custom breakdown tailored to your goals — no pressure, just real numbers. 

Get your free home valuation or see homes before they hit the market by contacting David J. Moore & Associates: 

• Phone: 443-733-6477 

• Website:www.ChesapeakeShoresRealtor.com 

• Email: connect@davidjmoore.net 

Your Home Sold at 100% of Asking Price—Guaranteed, or We'll Pay You the Difference.*