Boston, MA Real Estate Search

Boston, MA 5 Bedroom Homes for Sale

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Newest Boston, MA 5 Bedroom Homes for Sale

36-38 St Gregory Street, Boston
$1,350,000
5 Beds ⋅ 3 Baths ⋅ 73594273 MLS
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.

6 Oakdale St, Boston
$1,495,000
5 Beds ⋅ 3 Baths ⋅ 73593293 MLS
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.

20 W Cottage St, Boston
$1,299,000
5 Beds ⋅ 5 Baths ⋅ 73592848 MLS
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..

1114 Saratoga St Unit 2, Boston
$4,500
5 Beds ⋅ 3 Baths ⋅ 73591120 MLS
5 Bed | 3 Bath | I1600 sqft | n unit Laundry | Walk to Orient HeightsAvailable now: a 5 bedroom, 3 bath home of approximately 1,600 square feet at 1114 Saratoga St in the Orient Heights neighborhood of East Boston. With room to spread out, this layout works well for a larger household, roommates, or anyone who wants space for a home office.Inside, the kitchen features stainless steel appliances, and in-unit laundry. Five bedrooms and three baths give everyone their own space. Outside, the back yard is ready for grilling, gardening, or relaxing. On-street parking is available.Location is a big part of the appeal. The Orient Heights Blue Line station is nearby for a quick ride to downtown Boston, and Logan Airport is close for frequent travelers. And Revere shopping, dining, and the Blue Line stops along the way are easy to reach.Enjoy the local flavor of Orient Heights. Saratoga Street and Bennington Street are home to neighborhood favorites such as Caffe dello Sport for espresso, pastries, and gelato, Milano's Delicatessen for pizza, wraps, and deli fare, Luna's Italian and Latin Cuisine, and Angela's Cafe for homemade Mexican food. Everyday errands are covered by neighborhood markets such as Orient Heights Food Market and The Corner Mini Market. For fresh air, Constitution Beach offers a swimming beach, playground, athletic fields, and picnic area, and Belle Isle Marsh Reservation has trails and an observation tower with views of the Boston skyline.

1114 Saratoga St Unit 2, Boston

Listing courtesy of Listing Agent: Jamie Thompson from Listing Office: Thompson Realty.

4 Wakullah Street, Boston
$3,900
5 Beds ⋅ 2 Baths ⋅ 73591011 MLS
Available Now | 5-Bedroom Townhome in Historic Roxbury | 12-Month Lease. Enjoy spacious living in this charming, fully renovated, approximately 135-year-old property located in Roxbury’s historic Honeysuckle Hill neighborhood. Situated on a quiet, small one-way street, this two-level home offers five bedrooms, two full bathrooms, a large living room, a full kitchen, and a dedicated laundry hookup area. Comfort features include forced hot-air heating and central air conditioning.Conveniently located near bus routes and within walking distance of two MBTA T stations, this home offers easy access to public transportation and everyday essentials. The property is approximately a three-minute walk from Malcolm X Park, which features public tennis courts, soccer fields, a softball field, basketball courts, a children’s playground with a splash pad, a public swimming pool, and youth soccer programming. The park is also benefiting from a planned $10 million investment in additional recreational amenities.A shopping center is just a short walk away. The home is also around the corner from the historic Little-Collins House, associated with Malcolm X, and the former home of Reverend Oliver W. Childers.**Lease Details:**- Availability: Now- Lease Term: 12 months- Security Deposit: $3,900- Required Move-In Payments: First month’s rent, Last month's Rent and security deposit. No smoking permitted- No pets allowed. Located in Suffolk County, Boston, MA 02119. Don’t miss this opportunity to enjoy a spacious home in a historic Roxbury neighborhood with convenient access to public transportation, parks, and shopping.

4 Wakullah Street, Boston

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

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.

298 Columbus Ave Unit 3-4, Boston
$4,448,000
5 Beds ⋅ 5 Baths ⋅ 73588786 MLS
RARE OPPORTUNITY to own BOTH #3 & #4, creating an Exceptional Multi-Level offering in the HEART of South End near Back Bay. "IF" Combined These Two Residences offer 5-6 BEDROOMS, 4 BATHROOMS, 3,500 SF Across Four Levels. Unit 3 is distinct layout that offer incredible flexibility to live, work and play in the heart of Boston. Designed and Curated by Meyvn Studio, Unit #3 is a Parlor & Second Level Duplex. The bright & airy kitchen features paneled Appliances, floor-to-ceiling cabinetry & Waterfall Island, opening to a PRIVATE DECK, Perfect for Morning Coffee. Upstairs, The Penthouse Offers a JAW-DROPPING staircase leads to the bedroom level. Unit #4 offers private elevator access directly to a 1,668 Square Foot Penthouse Duplex with 3 BEDROOMS & 1.5 BATHROOMS. The beautiful kitchen features New Stainless Steel Appliances, custom stone counters & a large island with breakfast bar, opening directly into a spacious living/dining area with grand windows, fireplace & a rear-facing sunroom filled with natural light. Three bedrooms are located on the primary level, including two generous bedrooms with excellent closet space & a versatile third room ideal as a bedroom, office or flex space. EVERY DETAIL has been considered, from Farrow & Ball paint, new Doors, Fixtures & EMTEK Hardware to Lutron Caséta smart switches with dimmers. New German-designed tilt-and-turn aluminum windows offer excellent soundproofing, complemented by custom Shade Store window treatments. Central A/C & In-Unit Washer/Dryer complete the home. TWO DISTINCT RESIDENCES. ONE EXTRAORDINARY OPPORTUNITY. Perfectly positioned just steps from The Prudential Center, 200 Clarendon Street, Newbury Street, Back Bay (T) Station & Equinox Gym.

298 Columbus Ave Unit 3-4, Boston

Listing courtesy of Listing Agent: Collin Bray from Listing Office: Century 21 Cityside.

32 Perthshire Road Unit 32, Boston
$1,225,000
5 Beds ⋅ 3 Baths ⋅ 73586176 MLS
Set in one of Brighton’s sought-after neighborhoods, this beautifully renovated two-level home combines generous living space, abundant natural light, and a wonderful sense of privacy. Renovated just two years ago, the home features high ceilings, oversized windows, and an open, inviting layout designed for both everyday living and entertaining. The main level is anchored by a spacious open kitchen with a large center island—perfect for gathering with family and friends—with direct access to a private deck overlooking a tranquil wooded area. The kitchen flows seamlessly into the dining and living areas, creating a bright and welcoming space with an easy indoor-outdoor connection. Three bedrooms and a full bathroom complete this level. Upstairs, the expansive primary suite offers a true retreat, with a generously sized bedroom, an exceptionally large walk-in closet/dressing room, and a private en-suite bathroom. An additional bedroom and full bathroom provide flexibility for guests, family, or a home office. Additional features include in-unit laundry and one, cable ready, parking space. located near public transportation, highways, restaurants, universities, airport, this exceptional home offers the space and comfort of a larger residence with the convenience of a connected urban location.

32 Perthshire Road Unit 32, Boston

Listing courtesy of Listing Agent: Lynette Glover from Listing Office: Hammond Residential Real Estate.

31 Mount Vernon St, Boston
$1,299,000
5 Beds ⋅ 3 Baths ⋅ 73581851 MLS
Stunning Victorian two-family set on a lush, level quarter-acre-plus lot, a rare find for a Boston multi-family. Filled with character and thoughtful updates, this special property offers an adjustable floor plan, impressive bonus space, and an incredible outdoor setting. Unit one features two bedrooms, one bath, a lovely living room, open eat-in kitchen and an inviting sunroom overlooking the backyard. Unit two offers flexibility as either a 3-bedroom with a spacious living/media room or a 4-bedroom layout. The renovated kitchen features granite countertops, updated cabinetry, generous pantry storage, and bar seating at the peninsula, plus a modern full bath with a glass-tiled shower. A walk-up unfinished attic provides substantial storage and future expansion potential. The lower level offers even more usable space with laundry, a half bath, workshop, abundant storage, and two heated bonus areas currently used as a home gym and at-home bar. Outside is where the property truly shines! Established gardens and plantings surround a beautiful patio and level lawn, making it a private outdoor oasis for entertaining, gardening, and play. Interior improvements include kitchen and bath renovations, enclosed porch conversion to finished living space, boilers & water heaters; plus exterior improvements: both roofs (home + garage), full-house gutters with leaf guards and more! Extensive landscaping, hardscaping, fencing, irrigation, and underground rainwater management further enhance the grounds. Nearby favorites include: local library, coffee at Recreo, easy access to groceries and Trader Joe’s, Billing’s field, the YMCA and MBTA: Highland Station or West Roxbury Station (Needham Line Commuter Rail). This distinctive West Roxbury property offers tremendous flexibility: ideal for multi-generational living, a long-term investment, or an owner-occupant looking to offset expenses with rental income. Make this beautiful gem your own.

31 Mount Vernon St, Boston

Listing courtesy of Listing Agent: Katelyn E. Sullivan from Listing Office: Coldwell Banker Realty - Boston.

16 Common Street, Boston
$3,250,000
5 Beds ⋅ 4 Baths ⋅ 73578963 MLS
Extraordinary Location directly on the Training Field! Step into a piece of living history with this magnificent, single family masterpiece located in the heart of historic Charlestown. One garage parking space included! Originally constructed in 1800 as the legendary Old Salem Turnpike Hotel, this rare property seamlessly blends centuries of architectural heritage with the outstanding updates for sophisticated modern living. Boasting an impressive 3,578 square feet of meticulously maintained space, this grand 12-room estate offers an unparalleled lifestyle just across from the Training Field and minutes to downtown Boston. Boasting 4-5 Bedrooms and 4 full baths, plus a library, family room, and sunroom, it spreads comfortably across multiple stories. Expansive formal first floor living room, dining room, and gourmet kitchen! Enormous sun-filled yard is a gardener's paradise! Flexible floor plan for any lifestyle! This home retains its grand presence, timeless wood-siding exterior, and striking architectural character. Amazing intact wide-plank pine flooring throughout, plus multiple period fireplaces, one in almost every room! Perfect for New England winters. Situated on a generous 3,485 sq. ft. parcel, this home offers a rare blend of historic neighborhood charm and private outdoor space. Multi-zone heating and central air, plus premium updates throughout, ensure effortless comfort without sacrificing historic integrity. Located in one of Boston’s most coveted and historic enclaves, it offers top-tier convenience. Close to vibrant local dining, boutique shopping, and the historic Charlestown Navy Yard. Enjoy seamless access to the visual charm of gas-lit streets and quick transit to downtown Boston. This is a true once-in-a-generation legacy property. By appointment only.

16 Common Street, Boston

Listing courtesy of Listing Agent: Frank Celeste from Listing Office: Gibson Sotheby's International Realty.

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