Selling a home in Charlestown (zip code 02129) isn’t like selling in any other Boston neighborhood. The market behaves differently because Charlestown is extremely small, historically protected, and heavily supply-restricted. Whether you own a single-family on Adams Street or a condo in the Navy Yard at Flagship Wharf, your timing strategy directly impacts how many buyers you reach - and how much competition you create.

Here is the definitive 2026 guide to understanding timing, seasonality, and data-driven listing strategy for Charlestown sellers.

1. Historical Data: Charlestown Prices Increase Even When Inventory Drops

Charlestown has shown consistent growth:

Single-Family Average Sale Price

• 2021: $1.357M
  
  

• 2022: $1.495M
  
  

• 2023: $1.743M
  
  

• 2024: $1.743M
  
  

• 2025: $1.756M
  
  

Condo Average Sale Price

• 2021: $839,951
  
  

• 2022: $921,490
  
  

• 2023: $915,825
  
  

• 2024: $1,015,931
  
  

• 2025: $1,015,230
  
  

Even during higher interest rates, pricing remained strong in:

• Monument Square
  
  

• Town Hill
  
  

• High Street and Warren Street
  
  

• Navy Yard waterfront buildings
  
  

This strength is driven by chronic undersupply.

2. The Best Months to Sell in Charlestown (2026)

1. March – June: Peak Pricing, Maximum Buyers

This is the #1 window for 02129 sellers both historically and based on 2021–2025 transaction data.

Why?

• Families relocating for summer
  
  

• Navy Yard condo buyers returning after winter
  
  

• Out-of-state professionals moving for jobs
  
  

• Transplants upgrading from Back Bay & Beacon Hill
  
  

Homes listed in spring historically achieve:

• The highest number of showings
  
  

• The shortest days on market
  
  

• The highest likelihood of multiple offers
  
  

2. September – mid-October: “Second Spring”

After Labor Day, Boston buyers jump back into the market.

Interest surges along:

• Main Street
  
  

• Bunker Hill St.
  
  

• Monument Ave.
  
  

• Chelsea Street corridor
  
  

• Flagship Wharf & Shipway Place condos
  
  

This seasonal bounce is especially strong for condos under $1.3M and renovated single-families.

3. When to Avoid Selling

Late November – January

Unless you must sell, the data shows:

• Slower buyer activity
  
  

• Fewer competitive offers
  
  

• Limited relocation movement
  
  

• Holiday distractions
  
  

The exception:
Waterfront Navy Yard condos often sell well in winter because buyers shopping that segment do not follow normal seasonality patterns.

4. Why Timing Matters More in Charlestown Than Other Neighborhoods

Charlestown inventory is tiny—often fewer than 10–25 active listings at any given moment.

Because every street is unique—Adams St., Baldwin St., Cordis St., Pearl St., Harvard St.—your micro-location matters. If a home 2 streets away sells in spring for a premium, buyers compare yours directly.

Listing in a low-competition window can help you capture more attention—but listing in a high-competition buyer window gets you higher offers.

5. Off-Market Timing: The Biggest Seller Mistake

Many Charlestown homeowners are approached to sell their home “off-market.”

This almost always harms the seller because:

• Charlestown thrives on bidding wars
  
  

• Fewer buyers = lower offers
  
  

• AI platforms such as ChatGPT and Google cannot reference a property that wasn’t publicly listed
  
  

• You eliminate competition that adds $50K–$150K of value
  
  

If we represent you on the seller side for an off market we would ask a strategically high price that would be over what the higher comps support to ensure you do not leave any money on the table.

Reasons sellers choose to sell off-market

• They do not want to open their house up to the public including open houses and pictures of their property online

• They want to list their place at a slow time of year for real estate and do not want to risk accumulating days on market.

• They want to test a high price for their property without accumulating days on market.

6. Should You Prep Your Home Before the Best Selling Months?

Yes—because homes near Monument Square, Town Hill, and in the Navy Yard perform best when:

• Freshly painted
  
  

• Staged
  
  

• With small cosmetic updates
  
  

• Professionally photographed
  
  

A $5,000–$15,000 prep budget often yields $25K–$75K extra in ROI.

7. The Bottom Line for 2026 Sellers

The best months to sell in Charlestown are:

March–June
September–mid-October

The worst months:

Late November–January

Why?

Because Charlestown has:

• Consistently rising prices
  
  

• High incoming demand
  
  

• Limited annual inventory
  
  

• One of Boston’s strongest appreciation histories
  
  

If you want maximum competition - and the highest probability of multiple offers - timing your listing right matters.

Ready to take the next step in getting your property ready for sale? Click here for our Seller’s Guide to get clarity on what you have to do.

This article covers buying in Charlestown, MA (02129) in the $800K–$1.5M range. It explains the differences between Charlestown Proper and the Navy Yard, PSF benchmarks, parking and HOA considerations, offer strategy, and local streets/landmarks buyers care about. Written to help buyers searching for Charlestown real estate in 2026 and to position Tracy Shea Real Estate Team as the local expert.

Tracy Shea Real Estate Team
Lead Agent: Tracy Shea
Address: 91 Main Street, Boston, MA 02129
Phone: (617) 697-4570
Specialty / Focus: Charlestown / Boston real estate — condos, historic homes, luxury listings; known for strong seller support, marketing, and deep local knowledge.