5 Bedroom Homes for Sale in South End, Boston, MA

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Welcome to your dedicated resource for 5 bedroom homes for sale in South End, 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 South End, 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 South End, Boston, MA

$4,448,000

5 Beds ⋅ 5 Baths ⋅ 73588786 MLS ⋅ ACTIVE Status

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.

$5,825,000

5 Beds ⋅ 7 Baths ⋅ 73582794 MLS ⋅ ACTIVE Status

2016 New Construction/Gut Renovation of a 5-five story 2 unit brownstone offers a rare opportunity for multigenerational living, guest accommodations, owner occupied residence with income or au pair suite. Penthouse triplex with 3+ beds and ONLY 1 FLIGHT from the sidewalk features two living areas as well as rear and roof decks. Parlor duplex with 2 beds offers direct access to private patio and 2 full side-by-side parking spaces. Chef's kitchens with Thermodore appliances, gas fireplaces, central AC, open concept living, king-sized primary suites, walk-in closets, en-suite baths with step-in showers/double sinks, in unit laundry and oak hardwood floors. Follen Street is a peaceful dead end street on the Southwest Corridor that offers optimal proximity to private schools, dog parks, playgrounds, Pru Mall, Copley Square, Back Bay Trains and the conveniences of Boston's premier neighborhoods just moments from your door. Each of the 2 units in the building can be purchase separately and are listed for sale in MLS as #73588726 and #73588731.

18 Follen Street, Boston

Listing courtesy of Listing Agent: The Biega + Kilgore Team from Listing Office: Compass.

$6,795,000

5 Beds ⋅ 6 Baths ⋅ 73577426 MLS ⋅ ACTIVE Status

Located on a serene, tree-lined cul-de-sac and overlooking picturesque Sparrow Park with sweeping views of the Back Bay skyline, 68 W Rutland Square offers an elegant and expansive single-family residence boasting over 5,000 square feet of beautifully designed living space.Renovated from top to bottom, the home retains its original architectural details, such as soaring ceilings, decorative moldings, and grand bay windows, while offering every amenity for today’s discerning buyer. The layout includes a full-floor primary suite, 4 additional bedrooms, 3 full baths, and 3 half baths, providing generous space for both family living and entertaining. Enjoy THREE private outdoor spaces, a state-of-the-art home gym, a climate-controlled wine cellar, and a heated garage and driveway, something few South End brownstone homes can match. With Sparrow Park just outside your door, this is a rare opportunity to enjoy gracious city living with the indoor-outdoor lifestyle every Bostonian dreams of.

68 W Rutland Sq., Boston

Listing courtesy of Listing Agent: The Sarkis Team from Listing Office: Douglas Elliman Real Estate - The Sarkis Team.

$7,250,000

5 Beds ⋅ 6 Baths ⋅ 73575249 MLS ⋅ ACTIVE Status

Renovated Venetian Gothic beauty located on a much sought after South End Square – Rutland Square designed in the 19-Century around an English-style central garden park. This beautiful low stoop single family developed with a 4-story glass extension is comprised of 5 bedrooms (4 on the top two levels – a rare find), 4 bathrooms and 2 powder rooms, open concept kitchen flows naturally to the living/dining room, expansive family room, sitting room and separate library & office. Distinguishing features include 3 gas fireplaces, custom cabinetry & millwork, wired for home audio/surround sound, custom closets (tremendous amount of storage), designer/custom window treatments & rugs, 2 wet bars, high ceilings, 2 laundry locations, deck off the kitchen, roof deck, patio and direct access parking for 2 cars.

21 Rutland Square, Boston

Listing courtesy of Listing Agent: Sprogis Neale Doherty Team from Listing Office: Sprogis & Neale Real Estate.

$685,000

5 Beds ⋅ 2 Baths ⋅ 73513189 MLS ⋅ ACTIVE Status

Welcome to the South End, where every day feels like a vacation and the beach is just moments from your front door. Thoughtfully rebuilt and completely reimagined, this stunning coastal home offers the perfect balance of timeless style, modern functionality, and the laid-back lifestyle buyers dream about. Expanded with a full second level, the home features a bright, open-concept design that seamlessly blends spacious living, dining, and entertaining areas. A first-floor bedroom and full bath provide exceptional flexibility for guests, multi-generational living, or a private home office. Upstairs, escape to your luxurious primary suite, complemented by three additional generously sized bedrooms and a beautifully appointed full bath, creating plenty of room for family and friends. Whether you're starting your mornings with a walk on the beach, spending afternoons boating or soaking up the sun, or entertaining after a day on the water, this home offers the coastal lifestyle you've been waiting for. Beautifully renovated from top to bottom and completely move-in ready, this is more than a home—it's an opportunity to live where others vacation.

58 Willard Street, New Bedford

Listing courtesy of Listing Agent: Dawn Tramontano from Listing Office: Serhant.

$8,995,000

5 Beds ⋅ 7 Baths ⋅ 73485860 MLS ⋅ ACTIVE Status

Exquisite fully renovated 5+ bedroom townhouse! An ideal South End location on West Canton St between Warren Ave & Tremont St, this special home has been totally customized by the Lagasse Group and has been finished with the highest level of craftsmanship. A parlor level kitchen offers an oversized island, abundant storage, a beverage center, gas cooking and is open to a large dining space and a bow front living area with views east down Montgomery St. A double entry, half bath, private deck with floor to ceiling wall of glass, and tall ceilings complete the parlor level. A 2nd level primary suite is complete with 5 piece bath with ample storage, 2 walk in dressing rooms and a large bedroom. A 3rd floor is complete with 3 bedrooms, 2 full baths, auxiliary laundry & storage. Under the stoop entrance boats a large mudroom AND a walk in coat closet, the bedroom/home gym with en suite bath and a kids play room. Garden level media room with wine storage, private garden, laundry room.

158 W Canton St, Boston

Listing courtesy of Listing Agent: Michael Harper from Listing Office: Coldwell Banker Realty - Boston.

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5 Bedroom Homes for Sale in South End, Boston, MA

All 5 Bedroom Homes for Sale in South End, Boston, MA

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