5 Bedroom Homes for Sale in Boston, MA

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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

$890,000

5 Beds ⋅ 2 Baths ⋅ 73595164 MLS ⋅ EXTENDED Status

***$10,000 BUYERS CREDIT AT CLOSING*** HUGE HUGE single family property two full bathroom. Three levels of living space. First floor have a nice kitchen, hardwood floor, Four bedrooms. Second floor have two bedrooms, full bathroom, with yard space. Next to Orient heights train station, 10 minites to Logan Airport.

239 Leyden St, Boston

Listing courtesy of Listing Agent: Jocelyn Auguste from Listing Office: Bohio Realty LLC.

$1,350,000

5 Beds ⋅ 3 Baths ⋅ 73594273 MLS ⋅ ACTIVE Status

This rare two-family in Dorchester’s Lower Mills sits just one block from the neighborhood’s vibrant business district, with cafes, restaurants, and daily conveniences steps away. Both units are vacant and move-in ready, making it perfect for owner occupancy. Unit 2, a three bedroom duplex on the upper floors with room to spread out, is ideal for an owner’s suite. Rich woodwork brings warmth throughout, and an open kitchen flows into an expanded living area and defined dining space, made for everyday living and easy entertaining. A dedicated home office on the main level and an additional full bath add flexibility. The primary suite claims its own private upper level: a walk-through closet with integrated laundry leads to a spa-like bath with skylights, dual vanities, a pebble stone shower, and separate water closet. Two more bedrooms offer space for guests, work, or hobbies, and two private porches extend your living space outdoors. Unit 1 is a two bedroom, one bath residence full of classic character. Formal living and dining rooms with a built-in china cabinet pair with an updated kitchen and bath. A walk-through pantry with built-ins adds charm and storage, and a bonus room works as a home office or den. An enclosed private porch serves as a mudroom, and new HVAC provides year-round comfort. Both units have their own laundry and basement storage. Outside, enjoy a shared yard and three parking spaces, including one garage space. Close to the Red Line, the Neponset River Trail, parks, and harbor access, this is a chance to own a two-family in one of Boston’s most sought-after neighborhoods.

36-38 St Gregory Street, Boston

Listing courtesy of Listing Agent: Mission Realty Advisors from Listing Office: Compass.

$749,974

5 Beds ⋅ 2 Baths ⋅ 73593618 MLS ⋅ ACTIVE Status

Space, transit, and neighborhood momentum in Orient Heights. This 5-bedroom semi-attached single-family home offers a flexible layout that works as bedrooms, office space, guest space, or separate living areas, giving you more options than the typical condo or smaller single-family home in the area. Enjoy patio/yard space, central AC, and 2 full bathrooms, all in well-maintained condition. Great location, close to the T Suffolk Downs station, and the large-scale Suffolk Downs redevelopment now underway. Positioned between Revere and East Boston, the home offers city access and long-term neighborhood upside. An excellent option for an owner-occupant seeking more room and transit convenience. Schedule your showing today and see the possibilities for yourself!

1203 Bennington St, Boston

Listing courtesy of Listing Agent: Mission Impossible Team from Listing Office: United Brokers.

$1,495,000

5 Beds ⋅ 3 Baths ⋅ 73593293 MLS ⋅ ACTIVE Status

The marble mantel is still there — arched opening, scrolled keystone, original cast-iron summer cover in place. So are two pierced plaster ceiling medallions, a walnut stair with a carved volute and a rosette newel cap, deep built-up casings under a century intact after more than a century, 4-panel doors on original hardware, and a bay-window parlor that already works. JP's best condo resales are conversions of pre-1910 buildings, not new construction. Plenty of details to preserve here! An 1865 Second Empire three-family on a 9,600 square foot lot in the 3F-5000 subdistrict. Straight-sided slate mansard, segmental dormers with bracketed hoods, deep cornice on paired scroll brackets, 2-story canted bay. A spindled entry porch, a bracketed side porch, and wall-mounted espaliers. Nothing is built on the east side and nothing is likely to be: a community garden runs that line, then Lawndale Terrace, then the Southwest Corridor park, with the Orange Line beyond. 63.61 feet of frontage, just over 150 feet deep, roughly 73 feet of open yard behind the house, a 17.7 foot driveway on the west side, pkg for 4.The lot clears district minimums on area and frontage with room to spare. Setbacks are not a constraint. Keeping the shell and adding to the rear is the path the comps and the approvals both favor. Real work ahead, but the reward here is worth the effort. Site visits by appointment.

6 Oakdale St, Boston

Listing courtesy of Listing Agent: The Boston Home Team from Listing Office: Gibson Sotheby's International Realty.

$1,299,000

5 Beds ⋅ 5 Baths ⋅ 73592848 MLS ⋅ ACTIVE Status

Historic brownstone in Dorchester featuring 4 bedrooms and 3.5 baths across three levels, PLUS a legal 1-bedroom, 1-bath garden-level apartment with a reliable long-term tenant paying $2,377/month (direct deposit). A tasteful blend of old-world charm and modern amenities, with all the comforts of a recently renovated home. Beautifully refinished hardwood floors, marble tile, custom built-ins, five 18th-century marble fireplaces, and custom stained-glass transoms and high-end design add character throughout. The open-concept living, dining, and kitchen areas make entertaining a breeze. The chef's kitchen features stainless steel appliances, quartz countertops, a gas range, wine fridge/bar, abundant storage, and an adjacent newly added first-floor half bath. The second floor offers two spacious bedrooms and a beautifully renovated bathroom with a tub and rain shower. The third-floor primary suite boasts three built-in dressers, two walk-in closets, and a luxurious private bath. The fourth bedroom includes a new washer and dryer and an updated full bath. Enjoy a huge, partially covered deck overlooking a private, low-maintenance fenced-in turf yard with landscaping and a new wood privacy fence. Extensive renovations in 2025 included updated systems, central air, a new boiler, updated electrical, tankless hot water heaters, and more! Just four blocks from the Upham's Corner T station. Free, no permit, street parking. Nothing left to do but move in!

20 W Cottage St, Boston

Listing courtesy of Listing Agent: Darin Thompson from Listing Office: Stuart St James, Inc..

$2,750,000

5 Beds ⋅ 7 Baths ⋅ 73591962 MLS ⋅ ACTIVE Status

This offering presents a rare opportunity to acquire a seven-unit residential building in Boston’s Beacon Hill neighborhood, consisting of two studios and five one-bedroom units with a clear value-add opportunity. Two units have been fully renovated with in-unit washer/dryers, while the remaining five units are in classic condition, so the renovated units show what the others can achieve. Heating is forced hot water; one boiler, shared between 98 & 100 Myrtle St. Meanwhile, the property generates in-place rental income. The building is a short walk from Massachusetts General Hospital, one of the region’s largest employers, and to both the Red Line (Charles/MGH) and Green Line (Government Center) MBTA stations, giving residents easy access to downtown, Cambridge, and the greater Boston area. A deep employer base nearby, including MGH, the State House, Government Center, and the Financial District, supports consistent rental demand for studio and one-bedroom units, and residents also have the shops, restaurants, and amenities of Charles Street and the West End close by. With in-place income, a proven value-add business plan and meaningful upside, this property is an attractive investment in one of Boston’s most desirable and supply-constrained submarkets.

100 Myrtle Street, Boston

Listing courtesy of Listing Agent: Kevin Benzinger from Listing Office: Boston Realty Advisors.

$3,425,000

5 Beds ⋅ 4 Baths ⋅ 73591563 MLS ⋅ ACTIVE Status

Welcome to this beautifully renovated townhouse offering sophisticated city living in Boston’s historic Bay Village. Thoughtfully designed across multiple levels, this exceptional residence features 5 bedrooms and 4 bathrooms. The spacious kitchen boasts premium Thermador appliances, elegant granite countertops, and a dedicated dining area with direct access to a private patio, perfect for al fresco dining and entertaining. The living area seamlessly incorporates a dedicated home office space, creating the perfect balance of comfort and functionality. The luxurious primary suite occupies its own private floor, offering a peaceful retreat with a beautifully appointed bathroom featuring a glass-enclosed shower and a freestanding soaking tub. Additional bedrooms provide flexibility for guests, family, or work-from-home needs. Multiple outdoor spaces, including a private patio, balcony, and roof deck, offer wonderful opportunities to relax and entertain. Ideally located in the heart of Bay Village, just moments from the South End, Back Bay, and Downtown Boston, the property also offers convenient access to a garage directly across the street, where parking may be rented for approximately $250 per month. This distinctive home combines historic Boston charm, modern luxury, and exceptional urban convenience.

20-21 Shawmut St, Boston

Listing courtesy of Listing Agent: Marina Papanova from Listing Office: New Neighbors, Inc..

$2,600,000

5 Beds ⋅ 3 Baths ⋅ 73591350 MLS ⋅ ACTIVE Status

Discover the investment and development potential of 260 Metropolitan Avenue in Roslindale. This well-maintained three-family property with high ceilings, large rooms and period detail offers nearly 4,000 square feet of living space on a substantial 14,544-square-foot lot, complete with a detached garage with loft space and city views. The generous lot size and existing multi-family configuration offer potential for additional residential units, condominium conversion, or other development possibilities, subject to zoning and municipal approvals. Roslindale’s popular restaurants, shops, and parks are nearby, with convenient public transportation providing easy access to downtown Boston. Whether you're an investor, developer, or owner-occupant, this property is worth exploring. Buyers are encouraged to conduct their own due diligence regarding zoning, permitted uses, development feasibility, and required approvals.

260 Metropolitan Ave, Boston

Listing courtesy of Listing Agent: Eric Klein from Listing Office: Engel & Volkers Newton.

$699,900

5 Beds ⋅ 2 Baths ⋅ 73590878 MLS ⋅ ACTIVE Status

Discover the possibilities at 218 West Selden Street! This spacious 5-bedroom Colonial offers approximately 2,320 square feet of living space across three levels, combining classic charm with tremendous potential. The first floor features a welcoming foyer, generously sized living room, formal dining room with beautiful bay windows, spacious eat-in kitchen, utility room, and enclosed front porch. The second floor offers three bedrooms and a full bathroom, while the third floor provides two additional bedrooms, offering flexibility for a variety of living arrangements. Situated on an approximately 4,755-square-foot lot, the property also features a rear patio area with space for outdoor entertaining, gardening, or relaxation. With its generous room sizes, traditional layout, and original character, this home presents an excellent opportunity for buyers looking to update, renovate, and make it their own. Conveniently located in Mattapan near neighborhood amenities and transportation options. Bring your vision and unlock the potential of this classic Colonial!

218 West Selden Street, Boston

Listing courtesy of Listing Agent: Lindsey & Associates Realty Team from Listing Office: Keller Williams Realty Boston-Metro | Back Bay.

$7,990,000

5 Beds ⋅ 6 Baths ⋅ 73589980 MLS ⋅ ACTIVE Status

Located on coveted Chestnut Street in Beacon Hill, this south-facing residence underwent an extensive renovation by Holland following its purchase in 2018, blending French-inspired elegance with modern luxury. The chef’s kitchen offers a Lacanche range and expansive wood island, opening to a private patio with a gas fireplace and grill. Versailles parquet and chevron flooring, eight fireplaces, and exceptional craftsmanship distinguish the interiors. A grand living room with three stately windows connects to a living room and library/office. A private spa features an infinity pool and hammam with steam room. An elevator serves all five floors, including a luxurious primary suite with a marble bath and sitting room. The top-floor family room features original exposed beams and skylights. A remarkable home pairing historic character with beautifully appointed spaces for everyday living and entertaining. 11 Chestnut Street is steps away from the Boston Common, Public Garden, State House, Charles River Esplanade, Back Bay, and the fine boutiques and restaurants of Charles Street.

11 Chestnut Street, Boston

Listing courtesy of Listing Agent: Tracy Campion from Listing Office: Campion & Company Fine Homes Real Estate.

$1,499,000

5 Beds ⋅ 3 Baths ⋅ 73589871 MLS ⋅ ACTIVE Status

Rarely available multifamily opportunity in the heart of Charlestown! This 3 unit building is perfect for investors, developers, or end users looking to create something truly special. Unit 1 features 1 bed/1 bath, central A/C, and renovations completed in 2020. Units 2 and 3 each offer 2 beds/1 bath, presenting excellent potential for cosmetic updates and customization. Additional highlights include an enclosed patio, an updated roof deck, separately metered utilities for each unit and updated systems. Just minutes to all that Charlestown has to offer, a flexible layout and tremendous potential, this is a unique opportunity to reimagine or hold a MF property in one of Boston’s most sought-after neighborhoods.

25 Allston St, Boston

Listing courtesy of Listing Agent: The Goodrich Team from Listing Office: Compass.

$6,250,000

5 Beds ⋅ 6 Baths ⋅ 73589849 MLS ⋅ ACTIVE Status

A truly one-of-a-kind Beacon Hill residence, 70 Myrtle Street preserves the historic charm and curb appeal of its original exterior while offering the rare advantages of a 2019 new build within. Reconstructed from the ground up—including a newly excavated, deepened lower level—this exceptional home blends timeless architectural details with sophisticated modern design, systems, and amenities. Ash floors, reclaimed American White Oak used for built ins, hot water loop ensures hot water is immediately available in all bathrooms - no waiting to come up from basement, restored original elements, floating stairs, gas and wood-burning fireplaces, radiant heat bathroom and kitchen floors, smart-home controls, whole-house audio, zoned HVAC, and premium fixtures create an exceptional living experience. The Bulthaup kitchen features Gaggenau, Miele, and Sub-Zero appliances. Spa-like baths, a private primary-suite balcony, wine cellar, sauna, gym, and custom storage complete the interiors. Rare private outdoor space includes a landscaped, lighted patio with powered doors, Kalamazoo outdoor kitchen, gas and water service, and a permanently plumbed natural-gas fire table—an extraordinary Beacon Hill retreat. Live the life you were always meant to live, on the peak of Beacon Hill.

70 Myrtle St, Boston

Listing courtesy of Listing Agent: Bill Patterson from Listing Office: Craft Realty.

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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.

5 Bedroom Homes for Sale in Boston, MA

All 5 Bedroom Homes for Sale in Boston, MA

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