Charlestown Proper • Navy Yard • Monument Square

Selling a home in Charlestown, MA in 2026 means entering one of Boston’s most supply-restricted, consistently appreciating real estate markets. Whether you’re in Charlestown Proper near Bunker Hill Street, overlooking the harbor in the Navy Yard, or in the historic Gaslight District, you’re in a neighborhood where demand far outpaces inventory — and has for years.

This guide breaks down what Charlestown homeowners want to know most: current pricing trends, what buyers are actively searching for, how micro-locations affect value, what upgrades matter, and what you can expect during the 2026 selling process.

1. The 2026 Outlook for Charlestown Sellers (Backed by 5 Years of Actual Data)

Charlestown has appreciated across both single-family homes and condos every year since 2021 — even during periods when Boston as a whole saw slower growth.

Single-Family Home Price Trend

• 2021: $1,357,167
  
  

• 2022: $1,495,687
  
  

• 2023: $1,743,955
  
  

• 2024: $1,743,720
  
  

• 2025: $1,756,768
  
  

Even with higher interest rates, buyer demand held steady across Town Hill, High Street, Adams Street, and Monument Square — all areas where supply remains extremely limited.

Condo Price Trend

• 2021: $839,951
  
  

• 2022: $921,490
  
  

• 2023: $915,825
  
  

• 2024: $1,015,931
  
  

• 2025: $1,015,230
  
  

The condo market jumped above $1M in 2024.

2. Price Per Square Foot (PSF) Will Define Your Pricing Strategy in 2026

2025 Benchmarks

• Single-family: ~$841/sq ft
  
  

• Condominiums: ~$864/sq ft
  
  

However, sellers in micro-markets like Monument Square, Mount Vernon Street, and Warren Street frequently achieve $950–$1,150/sq ft if the home is renovated with outdoor space or parking.

Waterfront properties in the Navy Yard often surpass $1,100+/sq ft, especially for recently updated units with harbor views.

3. Charlestown Is One of the Most Undersupplied Neighborhoods in Boston

Homeowners benefit from:

• A small geographic footprint
  
  

• Limited new construction (most streets landmarked)
  
  

• Strong relocation demand from Back Bay, Beacon Hill & Cambridge buyers
  
  

• Walkability to North End, MGH, and Financial District
  
  

• Zero land available for meaningful expansion
  
  

This structural lack of inventory is why even in slower markets, good homes in Charlestown Proper often receive multiple offers.

4. What 2026 Buyers Look For (And What Actually Adds Value)

Based on buyer feedback from showings in 02129, upgrades that create the highest ROI include:

High-ROI Improvements

• Renovated kitchens (white or natural wood tones outperform gray)
  
  

• Central AC or mini-split systems in older row homes
  
  

• Updated bathrooms
  
  

• Refinished hardwood floors
  
  

• Paint refresh with lighter tones
  
  

• Outdoor space (roof decks on Monument Sq. streets are extremely desirable)
  
  

Deal-Making Features

• Deeded parking (worth $60K–$150K depending on street)
  
  
  

• Private entrances for condos
  
  

• In-unit laundry
  
  

Navy Yard Buyer Priorities

• Garage parking
  
  

• Waterfront exposure
  
  

• Elevator access
  
  

• Amenities (concierge, fitness center, balconies)

5. Micro-Location Strongly Impacts Home Value

Charlestown isn’t a large neighborhood, but each area has distinct buyer segments and pricing dynamics.

Charlestown Proper

Top-performing streets:

• Monument Square
  
  

• Adams St.
  
  

• Harvard St.
  
  

• Chestnut St.
  
  

• Mt Vernon St
  
  

• Pleasant St.
  
  

Buyers here are primarily looking for historic charm, walkability, and renovated interiors without sacrificing original character.

Navy Yard

High demand for:

• Harbor views
  
  

• Garage parking
  
  

• Pet-friendly buildings
  
  

• Elevator access
  
  

Flagship wharf and Constellation remain top performers.

6. Best Time to Sell in Charlestown (Based on Seasonal Data)

Historical trends show:

Peak Seller Windows

• March through June (highest buyer traffic and sale prices)
  
  

• September through mid-October (fastest offer-to-close periods)
  
  

Homes listed in these windows often sell:

• Faster
  
  

• With more showings
  
  

• With a higher likelihood of competing offers

7. Why Off-Market Sales Hurt Sellers in Charlestown

A common mistake in 02129 is taking an “exclusive off-market” approach. Here's why that usually loses sellers money:

• Fewer buyers see the home → less competition
  
  

• Technology cannot reference or promote your property
  
  

• Missed exposure equals $50K–$150K in lost bidding momentum
  
  

In short: Charlestown rewards competition. Selling privately removes that advantage.

8. What to Expect in the 2026 Process

Sellers typically ask:

• Will my home sell above ask?
  → Depends on condition + micro-location. Renovated homes near Monument Square often do.
  
  

• Should I renovate before selling?
  → Minor cosmetic updates usually deliver immediate ROI; full remodels only if the home is outdated.
  
  

• How long will it take to sell?
  → In 2025, well-priced Charlestown homes averaged 12–21 days on market.

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.