Charlestown Real Estate

Take a dash of Beacon Hill, mix with waterfront charm, deduct some price per square foot and you might arrive in Charlestown. As one of Boston’s oldest neighborhoods, Charlestown reflects its long, colorful history with colonial brick homes, gas-lit streets, constant views of harbor and skyline, plus inspired modern architecture. For many, it’s the best way to live in the heart of Boston.

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    The Charlestown Real Estate Market

    Although Charlestown’s historic glory is often linked to the Revolutionary War, its roots actually extend back to the 1620s. Back then it covered miles of territory. But as small hamlets (like Everett, Woburn and Malden) grew up and broke away, Charlestown finally settled into its current, one square mile of peninsula.

    By 1786, the first bridge across the Charles River connected Boston and Charlestown; in 1800, Charlestown’s famous Navy Yard was established. Businesses and light industry formed around existing churches and taverns. And an influx of Irish immigration in the 1860s helped create a close-knit, working class community in the red brick row houses along its cobbled streets.

    Charlestown did go through a rough period that peaked in the 1960s. But like similar areas in Boston, it began to gentrify in the ‘80s and ‘90s. Today, Charlestown is almost fully restored and highly coveted for its vintage beauty and easy access to Boston’s North End and downtown.


    Yet another of Boston’s towns-within-a town, the Charlestown community is known for its warmth and friendliness. Size has something to do with that, as well as its unique, waterside setting. Charlestown can truly feel like a world apart, with all the charm of a small New England village. Its monuments to Bunker Hill, the Freedom Trail and the U.S.S. Constitution (“Old Ironsides”) only add to its illusion of time standing still.

    But the fact is that today’s Charlestown is quite diverse and forward-facing. Here, a mix of wealthy and middle-class homes, housing projects and a large working-class, Irish-American culture create a uniquely Boston feel.

    Extremely walkable, with jaw-dropping views and fine shops and restaurants to discover on its main street and town square, Charlestown offers its residents plenty to smile about. If you’re thinking of living away from the hustle of Boston while remaining within striking distance, Charlestown could be for you.

    Is Now A Good Time To Buy In Charlestown?

    As a lower-priced option to its bigger, noisier neighbor, Charlestown has been consistently appealing year after year—especially for families and empty nesters. And Charlestown’s prestige continues to rise in the world. There may never be a better time to find your place in this one-of-a-kind neighborhood.

    Charlestown Properties

    143 High Street #1 Charlestown

    143 High Street #1

    List Price: $849,000
    2 Beds / 2 Full Baths
    1,126 SqFt

    262 Medford Street Charlestown

    262 Medford Street

    Sale Price: $959,000
    3 Beds / 2 Full Baths / 1 Half Bath
    1,915 SqFt

    8 Hancock Street Charlestown

    8 Hancock Street

    Sale Price: $700,000
    3 Beds / 2 Full Baths / 1 Half Bath
    1735 SqFt

    Some of the other Greater Boston neighborhoods we specialize in include:


    Brookline features abundant green space and a thriving cultural community. From historic Coolidge Corner to iconic restaurants and bars, Brookline combines the convenience of city living with the serenity of the suburbs.

    Learn more about Brookline real estate.


    Having experienced a development boom over the past decade, the Seaport is constantly evolving. This seaside neighborhood is known for modern, upscale living, and is home to much of the thriving Boston tech scene. And with some of the most popular restaurants and bars in Boston, the Seaport is attracting a diverse array of buyers and investors.

    More about Seaport real estate.

    South Boston

    Alongside the Seaport, South Boston has also been constantly evolving over the last several decades. Home to an array of individual neighborhoods, South Boston features a wide variety of single and multifamily homes and condos.

    Back Bay

    Located alongside the picturesque Charles River, the Back Bay is one of the most sought-after parts of downtown Boston. From Newbury Street shopping to summer afternoons in the Public Garden, many of Boston’s well-known landmarks can be found within this charming and historic neighborhood.

    More about Back Bay real estate.


    Located near the heart of the financial district in downtown Boston, Midtown is home to some of the most luxurious lifestyle condo buildings in the city. Buyers seek out Midtown for quintessential city living, with ample public transportation and many of Boston’s attractions within easy walking distance to the theater district.


    Perhaps best known as the home of Harvard University, Cambridge has a European, intellectual feel to it. With plenty of green space and some of the best running and biking paths near the city, Cambridge sits just across the river from downtown Boston.

    South End

    The epitome of a diverse neighborhood, the South End has something for everyone. With some of the hottest restaurants and most happening nightlife spots in Boston, the real estate market in the South End ranges from modern luxury condos to renovated historic brownstones and everything in-between.

    More about South End real estate.

    Beacon Hill

    Beacon Hill is perhaps the most historic neighborhood in Boston. Situated under the golden dome of the State House, and a short walk from the Boston Common, charm permeates the cobblestone streets of this quintessential Boston district.

    More about Beacon Hill real estate.