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5 Bedroom Homes for Sale in Boston, MA

Welcome to your dedicated resource for 5 bedroom homes for sale in Boston, MA. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Boston, MA agent, Marc Fiore specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the 5 bedroom properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All 5 Bedroom Homes for Sale in Boston, MA

$799,000
5 Beds 2 Baths 73560630 MLS ACTIVE Status
Welcome to 54 Richfield Street, a spacious 5 bedroom Colonial offering generous living space, flexibility, and exciting possibilities for the next homeowner. This longtime home offers approximately 2,300 square feet of living space, generously sized rooms, and the character of a classic New England home. Additional features include a front porch, rear deck, second floor balcony, off street parking, and a finished basement with two additional rooms. It’s a great extension of the home for buyers who need more room to live, work, entertain, or simply spread out.The current asking price reflects the home's present condition and anticipated updating, giving the next owner an opportunity to personalize the property and make it their own. The home also features a newer boiler and a roof that is less than 10 years old. Professional architectural plans are included with the sale, offering additional inspiration for buyers interested in exploring the possibilities for the property. Photos include a combination of current photographs of the home and virtually staged images of select rooms. The virtually staged images are provided to help buyers visualize the potential use, layout, and design of the spaces. Virtual furnishings and décor are not included with the property. Conveniently located near neighborhood amenities, transportation, and major routes. Bring your vision and discover the possibilities this spacious Dorchester home has to offer.

54 Richfield St, Boston

Listing courtesy of Listing Agent: Awilda Lalande from Listing Office: Keller Williams Realty.

$6,399,000
5 Beds 6 Baths 73557536 MLS ACTIVE Status
Welcome to 54 Pinckney Street! Tucked away on one of Beacon Hill’s most coveted blocks just steps from Louisburg Square, 54 Pinckney Street is a masterclass in refined city living. This meticulously renovated townhouse offers five sun-drenched levels of living space, steeped in a rich literary heritage as the former residence of Nathaniel Hawthorne. Every floor has been reimagined with an uncompromising eye for detail, creating a layout that flows effortlessly from one level to the next.At the heart of the home, the state-of-the-art kitchen is a chef’s dream, featuring sleek granite countertops and a premium appliance suite by Wolf, Sub-Zero, and Bosch. It opens directly onto a lush, private garden patio—a rare outdoor sanctuary that was recently featured on the prestigious Beacon Hill Hidden Garden Tour. This professionally planted oasis offers a level of horticultural beauty and privacy that is truly exceptional for the city.The second level serves as the home's centerpiece, boasting a grand formal living room with soaring ceilings and a handsome study/media room complete with a custom wet bar.The primary suite is a true retreat, with a large walk in closet and a breathtaking, spa-like bathroom anchored by a deep resin soaking tub and a glass enclosed shower room. The top floor contains 3 additional bedrooms and two full marble bathrooms featuring Water Works fixtures. Throughout the residence, five stately fireplaces, bespoke millwork, and rich hardwood floors add layers of warmth and character. Practicality is woven into the design with two laundry areas, all-new systems, and a versatile lower-level au pair suite. This private guest space includes a wine cellar, a new kitchen and its own separate entrance, providing independence and convenience for long-term visitors.A modern fire suppression sprinkler system and a security system is also in place.This is a masterful recreation of Old-World Boston, reimagined for a contemporary lifestyle with the highest caliber of craftsmanship and a storied past. Some photos are from a prior listing.

54 Pinckney St, Boston

Listing courtesy of Listing Agent: Cort LaBonte Coldren Coopersmith Group from Listing Office: Compass.

$899,000
5 Beds 2 Baths 73556941 MLS ACTIVE Status
Perched high atop Bigelow Hill on a quiet cul-de-sac on a relatively level lot near Oak Square, this classic Brighton two-family offers sweeping skyline views, exceptional flexibility, and outstanding potential for both owner-occupants and investors. Whether you're looking to offset your mortgage with rental income, create a multigenerational living arrangement, renovate to build equity, or expand your investment portfolio, this property presents a rare opportunity in a highly desirable location. The first-floor unit offers five rooms with a flexible 2 or 3 bedroom layout, while the second-floor unit offers six rooms with a flexible 2 or 3 bedroom layout. Both units feature hardwood floors, abundant natural light, and separate all-electric utilities. The versatile floor plans allow the third bedroom to easily function as a formal dining room, home office, or den to suit a variety of lifestyles. The first-floor unit is ready for renovation, providing the opportunity to update and customize the space to your own vision, while the second-floor unit offers immediate owner-occupancy or rental income potential. The lower level presents excellent expansion possibilities, including potential for an Accessory Dwelling Unit (ADU), additional living space, guest suite, home office, or recreation area, subject to buyer verification and all applicable City of Boston approvals. Outside, the property features a two-car driveway plus a rear right-of-way along the right side of the property that may provide opportunities for additional parking or improved access. Buyers are encouraged to review the recorded Right-of-Way document available in the MLS Documents section. Enjoy the convenience of nearby Oak Square's restaurants, cafés, shopping, parks, public transportation, and easy access to downtown Boston, Cambridge, Storrow Drive, the Massachusetts Turnpike, and Routes 95 and 128. Qualified owner-occupants may also be eligible for the City of Boston Residential Exemption. For Fiscal Year 2026, the exemption reduced eligible homeowners' real estate tax bills by $4,353.74. Buyers should verify eligibility and apply directly with the City of Boston Assessing Department.Properties offering this combination of location, flexibility, panoramic views, expansion potential, and value-add opportunity are increasingly difficult to find.

9-11 Hardwick Ter, Boston

Listing courtesy of Listing Agent: Jim & Mike Savas Team from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

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