Charlestown Homes for Sale

Charlestown Homes for Sale

Welcome to Charlestown, a vibrant and historic neighborhood nestled in the heart of Boston, Massachusetts. With its rich history, charming architecture, and stunning waterfront views, Charlestown offers a unique blend of urban living and small-town charm. As one of Boston's oldest neighborhoods, Charlestown is renowned for its cobblestone streets, iconic Bunker Hill Monument, and the picturesque Charlestown Navy Yard, which is home to the USS Constitution.

Charlestown boasts a diverse array of homes for sale, catering to various tastes and lifestyles. From beautifully restored brownstones that echo the neighborhood's historic past to modern condominiums with breathtaking views of the Boston skyline, there’s something for everyone. Families will appreciate the spacious single-family homes with lush gardens, while young professionals may be drawn to contemporary lofts that offer a chic urban lifestyle.

Living in Charlestown means enjoying a tight-knit community atmosphere, complete with local shops, cozy cafes, and an array of dining options that highlight Boston's culinary scene. Residents also benefit from easy access to public transportation, making commuting to downtown Boston or exploring surrounding areas a breeze.

Whether you're a first-time homebuyer or looking to invest in a property with character and charm, Charlestown's homes for sale are an enticing opportunity. Discover the perfect blend of history, culture, and modern living in this exceptional Boston neighborhood. Come and experience the allure of Charlestown—your dream home awaits!

Newest Charlestown Homes for Sale

42 Harvard Street, Boston
$4,750,000
5 Beds ⋅ 5 Baths ⋅ 73590132 MLS
Overlooking John Harvard Mall in Charlestown’s historic gaslight district, this handsome, 5+BR/4.5BA, bow front brick townhome, offers 4,000sf of living space and two covered parking spaces. Built circa 1875, the home was rebuilt from the brick façade inward in 2009/10, with all-new framing and major systems, then thoughtfully reimagined in 2024/25 for modern family living. The main level is open and filled with light, with living, dining, and kitchen spaces flowing together beneath crown molding and custom millwork. A gas fireplace with porcelain surround anchors the living area, and a multi-zone sound system carries music throughout. The chef’s kitchen centers on a large marble-topped island and is equipped with a new Thermador six-burner range with grill and double ovens, plus a Sub-Zero refrigerator. Oversized windows and skylights brighten the space, and a French door opens to a private side porch for outdoor dining and grilling. A powder room services this level. The entire second floor is reserved for the primary suite, w/dual walk-in closets and a spa-style bath featuring a freestanding soaking tub, double vanity, and oversized walk-in shower. The third-floor features two generous bedrooms w/dual custom closets; a dedicated home office, full bath, and laundry center. The fourth-floor adds a custom built-in library or study and guest suite. Above it all, the roof deck offers 360-degree views of Boston Harbor and the city skyline. The lower provides versatile living space: a media room w/wet bar and EuroCave wine refrigerator, a gym or au pair suite, an oversized mudroom w/heated floor, abundant storage, and second washer/dryer. A 2-car covered driveway is just off the mudroom. Historic character, modern systems, and a coveted location make this a turnkey Charlestown home.

42 Harvard Street, Boston

Listing courtesy of Listing Agent: Nancy Roth from Listing Office: Gibson Sotheby's International Realty.
16 Chestnut Street, Boston
$2,850,000
4 Beds ⋅ 4 Baths ⋅ 73512592 MLS
Perfectly positioned between the Training Field and the Charlestown Navy Yard, this newly renovated single-family brownstone offers four levels of luxury living in one of the neighborhood’s most coveted locations. The home features 4 bedrooms plus a large finished lower level with dedicated storage—ideal for a media room, gym, or playroom. A stunning chef’s kitchen with marble surfaces and Thermador appliances opens to a private patio with a gas grill hookup, perfect for indoor-outdoor entertaining.The primary suite is a true retreat, complete with a steam shower, gas stove, and a dedicated sitting area that opens to a private balcony with breathtaking city views. A second-level south-facing roof deck with a gas fire-pit hookup provides exceptional outdoor living. Beautiful exposed brick, refined finishes, and thoughtful craftsmanship are showcased throughout. This home combines new construction, period detail, historic surroundings, and unmatched Charlestown Walkability.

16 Chestnut Street, Boston

Listing courtesy of Listing Agent: Zachary Endicott from Listing Office: RE/MAX Encore.
Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

board logoCopyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

How much is your home worth?

Get instant property value now!