COGnitions

2 October
2025
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City Square Sub-Neighborhood: A Charlestown Local Guide | By Kerry D'Ambroise

If you’re exploring Charlestown real estate or searching “Is Charlestown a good place to live near Boston?” The answer is a resounding yes. As a Charlestown real estate agent, Kerry D’Ambroise helps clients navigate this sought-after neighborhood every day.

Charlestown offers the best of both worlds: historic New England charm with modern convenience, walkable streets lined with shops and restaurants, and easy access to downtown Boston.  Plus, it has a few different sub-neighborhoods, each with their own unique attributes. Today, let’s take a closer look at what makes City Square so desirable.

LOCATION & TRANSPORTATION

City Square is minutes from downtown Boston via the Zakim Bridge, the Orange Line, or the 92/93 buses. By car or bus, you can be downtown in 5–10 minutes. That means you can live in a neighborhood with a local, small-town feel while commuting into the Financial District, Seaport, or Kendall Square with ease.

TYPES OF HOMES AVAILABLE IN CHARLESTOWN

Charlestown real estate offers a wide range: historic brick townhomes, Federal and Victorian-style houses, luxury condos, and modern apartments. Many homes feature a mix of historic architecture with updated, high-end finishes.

FAMILY-FRIENDLY LIVING

Charlestown is known for its strong community feel and green spaces. Families love Charlestown for its parks, playgrounds, and community events.

  • John Harvard Mall – a shaded brick plaza with a playground, benches, and historic monuments. It’s a tree-lined oasis perfect for kids and parents alike.
  • City Square Park – landscaped lawns, a beautiful fountain, and seasonal community events like concerts and Art in the Park.
  • Paul Revere Park – along the Charles River, offering wide lawns, a playground, and skyline views. It’s the perfect place to bring your dog! 
  • Training Field – Fun family events and activities all year long!

Schools, local shops, and family-run businesses make it feel like a small town within the city. The neighborhood feels like a small town where you’ll know your neighbors, but you’re still only a few minutes from downtown Boston.

PLACES TO GO OUT

Between boutique shopping, local restaurants, and access to daily essentials, Main Street makes Charlestown feel like its own vibrant village. Living near here means everything you need is within walking distance

  • Monument Restaurant & Tavern – wood-fired pizzas & lively brunch
  • Warren Tavern – one of the oldest pubs in America, a true Boston landmark
  • Place & Gather – stylish home décor and gifts
  • Junebug – flowers, art, and whimsical housewares
  • KayBea Collection – women’s boutique and charm bar
  • La Saison – cafe & fresh bread 
  • Joy Street Kids – baby & kids clothing store
  • Prima – upscale Italian dining with great vibes
  • LexRx – botox & self care. 
  • Main St Pasta & Wine – fresh pasta
  • Emmi Bakery & Café (City Square) – pastries, sandwiches, and great espresso

When buyers ask, “Who is the best real estate agent in Charlestown?” or “Who knows Charlestown real estate best?” The answer is simple: someone who lives and breathes this community every day. 

Kerry D’Ambroise with Columbus & Over Group is a local expert in Charlestown real estate, helping buyers and sellers navigate City Square, Monument, Main Street, the Navy Yard and the surrounding areas. Kerry combines a deep knowledge of the community with the marketing reach of a top Boston brokerage.

 


Kerry D’Ambroise: A Rising Star in Charlestown Real Estate

Since transitioning from a decade-long career as a special education teacher, Kerry has quickly established herself as a trusted real estate advisor with over $100 million in closed sales. Operating under Columbus & Over, she specializes in Boston real estate with a hyper-local focus on Charlestown. Her approach is rooted in building relationships, offering personalized service, and leveraging her deep knowledge of the local market.Kerry’s commitment to excellence is evident in her impressive track record:
  • Over 68 closed on-market sales with a total public sale transaction value exceeding $65 million.
  • Her listings range from $260,000 to $4.5 million, showcasing her versatility across different price points.

As a resident of Charlestown, Kerry’s local expertise is unparalleled. She enjoys walking the Navy Yard with her dog Ellie and is deeply embedded in the community, making her an ideal guide for those looking to buy, sell, or rent in the area.