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$1,800,000
4 Beds ⋅ 3 Baths ⋅ 73526128 MLS
It’s rare to find a turnkey two-family that hits every mark, but this Charlestown gem on a quiet, sought-after street does exactly that. Whether you’re looking for a high-performing investment or a home with built-in rental income, this property delivers. Unit 1 is a modern one-bedroom retreat with a private deck. Upstairs, Unit 2 is a stunning duplex that masterfully balances contemporary updates with historic character. The main level flows seamlessly between the kitchen, dining, and living areas, while the top floor houses three sun-filled bedrooms and a stylishly renovated bath.The real "wow" factor? The private roof deck. It offers breathtaking, 360-degree unobstructed views of the city skyline—a true sanctuary in the heart of the neighborhood. With a proven track record for short-term rentals and a flexible layout, this is a standout opportunity in one of Boston’s most iconic locations.

19 Walker St, Boston

Listing courtesy of Listing Agent: Aranson Maguire Group from Listing Office: Compass.
$2,625,000
5 Beds ⋅ 5 Baths ⋅ 73519421 MLS
There are levels to real estate construction... and this is the top! Welcome home to a no-expense-spared ground-up single family with an idyllic floorplan and designer finishes throughout. Open & inviting living with framed gas fireplace, 9' ceilings, and incredible natural light. Designer kitchen features oversized quartzite island, professional grade appliances, custom cabinetry, built-in bar, and direct access to formal dining. Oversized primary suite, with private balcony, is out of magazine! Featuring space for a kingsize, gigantic walk-in closet, and designer bath with frameless glass shower+double vanity+soaking tub. Generous guest beds with dedicated custom baths. Finished lower-level creates the perfect space for an au pair suite, media room/gym/home office. Enjoy the seasons on your fully enclosed stone patio and breathtaking roofdeck with panoramic views from Boston Harbor, across the Skyline, and over the Monument! A special home that truly "has it all". Free rental parking on Prospect Street!

14 Prospect St, Boston

Listing courtesy of Listing Agent: Adam Geragosian from Listing Office: William Raveis R.E. & Home Services.
$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.
$1,095,000
4 Beds ⋅ 2 Baths ⋅ 73497271 MLS
Tucked away off the street along a private walkway, this updated single-family home offers a rare sense of privacy in the heart of Charlestown. Thoughtfully renovated, this four-bedroom, two full bath home features a bright, sun-filled interior with quartz countertops, brand new stainless steel appliances, fresh paint, and new carpeting throughout. A flexible floor plan includes a first-floor bedroom—ideal for guests, home office, or den—nearby full bath with laundry. Generously sized bedrooms and an airy layout provide comfortable, versatile living. Step outside to a private patio, perfect for relaxing or outdoor dining. Additional highlights include a large, clean basement for storage or workshop use. A unique opportunity to own a single-family home offering both privacy and convenience near Charlestown amenities, transportation, and Boston. This wonderful residence lives and feels much larger than its square footage! Don't miss this truly outstanding opportunity!

18R Polk Street, Boston

Listing courtesy of Listing Agent: Frank Celeste from Listing Office: Gibson Sotheby's International Realty.
$4,490,000
5 Beds ⋅ 4 Baths ⋅ 73497043 MLS
Presenting the opportunity to acquire a premier Charlestown mixed-use asset located at 89 Green Street and 194-198 Bunker Hill Street. This offering delivers a rare combination of stable, fully occupied tenancy with approvals for additional development in one of Greater Boston’s most desirable and supply-constrained neighborhoods. 89 Green Street is comprised of three residential units. 194 Bunker Hill Street consist of 2 residential units and the Bunker Hill laundromat. In addition, 198 Bunker Hill, currently a dated, single-story vacant building, is fully approved for a new, four-unit development consisting of 2-bed/bath apartments or for-sale condominiums. Floor plans and Matterports available upon request.

89 Green St, Boston

Listing courtesy of Listing Agent: Nicholas Herz from Listing Office: Boston Realty Advisors.
$700,000
2 Beds ⋅ 2 Baths ⋅ 73496353 MLS
City of Boston Affordable resale unit now available. Incredible opportunity to secure a stylish two bedroom with two bathrooms, in an elevator building. Enjoy the manicured surroundings in the Charlestown Navy Yard, while capturing Boston Harbor water views. Easy floor through living featuring hardwood floors throughout, dedicated dining space and a modern kitchen, complete with granite counter tops and stainless steel appliances. Both the master bathroom and the guest bathroom have been tastefully updated. This condominium is just a few blocks from the 93 MBTA Bus Route, the MBTA Ferry to downtown and the airport, The Freedom Trail, the USS Constitution and the shops and restaurants of Charlestown. Enjoy easy access to RT 93, Whole Foods, the Orange Line T station and downtown Boston from this wonderful city pad. MUST MEET BPDA INCOME GUIDELINES.

65 Chelsea Street Unit 305, Boston

Listing courtesy of Listing Agent: Brian Caluori from Listing Office: Gibson Sotheby's International Realty.
$840,000
2 Beds ⋅ 2 Baths ⋅ 73495408 MLS
Distinctive single-family set behind a private gateway along a secluded pathway, featuring a beautifully landscaped courtyard garden with mature perennials and over 1,000 bulbs and a cute garden shed—recognized as a Boston Garden Contest finalist. A compelling alternative to condo living, blending modern updates with old world charm.The kitchen redesigned to maximize space and functionality, offering a central island, exposed wood beams, granite countertops, and stainless steel appliances. A reimagined full bath and laundry area complete this level.Upstairs, the sun-filled living room showcases original wide pumpkin pine floors and a wood-burning fireplace, along with an updated full bathroom. The top floor is devoted to two cathedral-ceiling bedrooms, including a light-filled primary with skylight and additional hallway storage complete this level. A rare blend of timeless charm, excellent walkability to downtown, the waterfront, and local dining.

4 Mead Street Ct, Boston

Listing courtesy of Listing Agent: Lisa Godwin from Listing Office: Gibson Sotheby's International Realty.
$840,000
2 Beds ⋅ 2 Baths ⋅ 73494772 MLS
Distinctive single-family set behind a private gateway along a secluded pathway, featuring a beautifully landscaped courtyard garden with mature perennials and over 1,000 bulbs and a cute garden shed—recognized as a Boston Garden Contest finalist. A compelling alternative to condo living, blending modern updates with old world charm.The kitchen redesigned to maximize space and functionality, offering a central island, exposed wood beams, granite countertops, and stainless steel appliances. A reimagined full bath and laundry area complete this level.Upstairs, the sun-filled living room showcases original wide pumpkin pine floors and a wood-burning fireplace, along with an updated full bathroom. The top floor is devoted to two cathedral-ceiling bedrooms, including a light-filled primary with skylight and additional hallway storage complete this level. A rare blend of timeless charm, excellent walkability to downtown, the waterfront, and local dining.

4 Mead Street Ct, Boston

Listing courtesy of Listing Agent: Lisa Godwin from Listing Office: Gibson Sotheby's International Realty.

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