2026 BUYER GUIDE — CHARLESTOWN, MA (02129)

Charlestown Proper, Navy Yard & 2026 Market Expectations

Charlestown, MA continues to be one of Boston’s most stable and desirable neighborhoods for buyers entering the 2026 market. Whether you're focused on the historic charm of Charlestown Proper, the waterfront lifestyle of the Navy Yard, or the boutique condo buildings off Main Street and Bunker Hill Street, the last five years of market data tell a clear story: Charlestown appreciates steadily, even when wider Boston shows volatility.

This guide breaks down everything buyers want to know going into 2026 — including real pricing data, PSF trends, financing expectations, and what it’s actually like competing in the 02129 market.

1. What Charlestown Buyers Should Expect in 2026 (Backed by Real Data)

Single-Family Home Prices (2021–2025)

Charlestown’s single-family segment has shown consistent growth:

• 2021: $1,357,167 avg sale
  
  

• 2022: $1,495,687 avg sale
  
  

• 2023: $1,743,955 avg sale
  
  

• 2024: $1,743,720 avg sale
  
  

• 2025: $1,756,768 avg sale
  
  

The biggest jump happened between 2022 → 2023, driven by ultra-low supply in Monument Square, the Training Field area, and the Gaslight District.

Condominium Prices (2021–2025)

Condo buyers will have a slightly more approachable entry point:

• 2021: $839,951 avg sale
  
  

• 2022: $921,490 avg sale
  
  

• 2023: $915,825 avg sale
  
  

• 2024: $1,015,931 avg sale
  
  

• 2025: $1,015,230 avg sale
  
  

Charlestown condos crossed the $1M average starting in 2024, especially influenced by Navy Yard buildings like Flagship Wharf, Parris Landing, Constellation Wharf, and more boutique buildings near City Square.

2. Price Per Square Foot (PSF)

Single-Family

• 2021: $714/sq ft
  
  

• 2025: $841/sq ft
  
  

A ~17% increase over four years — surprisingly stable for a Boston submarket this small.

Condos

• 2021: $763/sq ft
  
  

• 2025: $864/sq ft
  
  

Navy Yard waterfront units tend to exceed the neighborhood average.

3. Hyperlocal Breakdown: What Buyers Ask About Most

Charlestown Proper (02129)

Most buyer demand centers around:

• Monument Square
  
  

• Bunker Hill Street (Gaslight District)
  
  

• Warren St. corridors
  
  

• The School Street / High Street hilltops
  
  

• The Main Street retail spine
  
  

Historic brick and brownstone homes dominate this part of Charlestown — and buyers here often ask about renovation limits, historic encumbrances, and parking availability.

Navy Yard

Buyers focused on Navy Yard usually want:

• Waterfront living
  
  

• Elevator buildings
  
  

• Garage parking
  
  

• Modern amenities
  
  

Top buildings remain:

• Flagship Wharf
  
  

• Parris Landing
  
  

• Constellation Wharf

4. Parking Is Still the #1 Buyer Concern

With many homes built in the 1800s–1900s, Charlestown Proper has limited off-street parking.

Typical questions:

• “How hard is street parking near Montmorenci Ave?”
  
  

• “Does a Town Hill condo include a deeded space?”
  
  

• “Are Navy Yard garage spots deeded or rented?”
  
  

Parking adds $60K–$150K in value depending on location, with Main Street and Bunker Hill spots on the high end.

5. Flood & Insurance Questions

Navy Yard buyers especially ask:

• Is Flagship Wharf in a FEMA flood zone?
  
  

• Are premiums reasonable for a waterfront unit?
  
  

• What elevation protections exist?
  
  

Most waterfront condo associations have updated mitigation since 2020, keeping costs manageable.

6. Financing Realities in 2026

Most Charlestown buyers fall into:

• Conventional 20%–30% down
  
  

• Jumbo financing (common above $1.5M)
  
  

• VA buyers around Navy Yard (due to proximity to military history & base access)

But it doesn’t have to look that way for everyone - Some instances end up with the buyer putting as little as 3-5% down. Reach out to us to see if that can be a possibility for you.

7. How Charlestown Compares to the Rest of Boston

According to LINK Analytics:

Charlestown remains:

• More affordable than Beacon Hill, Back Bay, Downtown, Seaport
  
  

• More expensive than East Boston, West End, and North End
  
  

This keeps demand extremely strong, especially for buyers priced out of Back Bay but still wanting historic charm.

Ready to take the next step in finding your perfect property? Click here for our Buyer’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.