Roslindale, Boston, MA 5 Bedroom Homes for Sale

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Newest Roslindale, Boston, MA 5 Bedroom Homes for Sale

$1,199,000

5 Beds ⋅ 4 Baths ⋅ 73589161 MLS

Updated 4 family on a large corner lot with contemporary finishes including carrera quartz counters, stainless steel appliances and classic ceramic subway tile accents. There are beautiful original hardwood floors throughout the property and each unit has an enclosed porch with ceramic tile floors off of the kitchen. There is a parking area with enough space for at least 4 cars and a large private storage room in the basement along with laundry facilities and a common yard. Three out of the four units are currently leased through 8/31/27. Gross income of over $113,000 and all of the units have separate utilities. Conveniently located just 1 mi from Roslindale Village and 1.5 miles from Forest Hills, this gem is not to be missed.

836 Canterbury St, Boston

Listing courtesy of Listing Agent: Adam Umina from Listing Office: Metro Realty Corp..

$1,499,000

5 Beds ⋅ 3 Baths ⋅ 73577856 MLS

For the discerning buyer, this architecturally exquisite home was custom-built in the 1880s and has been custom renovated to preserve and celebrate its late Aesthetic and early Craftsman heritage. From soaring coffered ceilings and intricate paneling to custom fireplaces, original built-ins, stained glass and exquisite spandrel fretwork, every room reveals craftsmanship rarely found in today’s homes. The stunning kitchen exemplifies modern functionality, offering abundant custom cabinetry, quartz countertops, an oversized island and an externally vented induction cooktop. French doors open directly to the mahogany deck, creating an effortless connection to the outdoors—perfect for morning coffee, al fresco dining or relaxing at the end of the day. The dining room is a true showpiece, wrapped in intricate spandrel fretwork and anchored by original built-ins and a custom fireplace. The oversized living room is equally impressive, with coffered ceilings, custom fireplace, stained glass and a distinctive round nook that invites chess, checkers or intimate conversation. Custom paneling frames the regal staircase to the 2nd floor, where 4 bedrooms await. The newly crafted primary suite features multiple closets, a dedicated dressing room and ensuite bath. The 2nd and 3rd bedrooms offer their own charm, while the 4th bedroom provides flexibility as a home office, nursery or guest room. For the adventurous, climb the steep stairs to the top floor and discover a huge lounge and bonus 5th bedroom with vaulted ceilings and skylights—an ideal retreat for getting away from it all. Double sized lot offers a large, lush front lawn, rear patio and mahogany deck that create a private, inviting outdoor setting. A dual-access driveway enters from Brown Ave and exits onto Ada St, while the custom shed provides easy storage or flex space. The large unfinished basement also offers loads of clean storage space. Infrastructure and major systems have been comprehensively updated, including electrical, plumbing, windows, kitchen, baths, roof, exterior, decks, and landscaping—allowing the next owner to enjoy the beauty and craftsmanship of a historic home with the confidence of modern updates. More than a residence, this is a remarkable piece of architectural history—thoughtfully preserved, beautifully renewed, and truly distinctive.

41- Brown Ave, Boston

Listing courtesy of Listing Agent: Michaela Hellman from Listing Office: Redfin Corp..

$1,249,000

5 Beds ⋅ 5 Baths ⋅ 73576595 MLS

Generational living, investment opportunity, and the best of Roslindale Village — all in one property.Find the space, flexibility, and location that make life easy at 33 Cohasset Street, just a half-block from Roslindale Village. The property currently consists of two individual condominiums, offering an ideal setup for extended family, owner-occupants, investors, or anyone looking for a little more room to spread out. Unit 1 is a thoughtfully laid-out 2-bedroom, 2-bathroom condo, currently rented through August 2027 at $3,100/month. Unit 2, the owner-occupied residence, spans two levels and offers 3 bedrooms, a dedicated office, 3 full bathrooms, and an expansive yard and patio — a surprising amount of outdoor space this close to the Village. Gut-renovated in 2014, both units offer functional layouts and plenty of space to live, work, host, and make your own. Four parking spaces, a large and easily accessible basement with ample storage, and the Commuter Rail just two blocks away make everyday life remarkably convenient, whether you're driving, biking, walking, or commuting into Boston. And then there's the neighborhood. Roslindale Village is practically at your doorstep, with restaurants, coffee shops, bars, and local shopping just down the street. Venture a few blocks farther and you'll find parks, farmers markets, and even more of what makes Roslindale such a great place to call home. 33 Cohasset is currently deeded as 2 separate condos, but can be changed to a 2-family before closing.

33 Cohasset St, Boston

Listing courtesy of Listing Agent: Michael Sokolowski from Listing Office: ENRG Global Realty, LLC.

$5,500

5 Beds ⋅ 4 Baths ⋅ 73555136 MLS

Group showing by appointment only on Sun., 10/11 from 9:45a to 10:30a--WELCOME HOME!! Minutes from Roslindale Village--Beautiful, spacious, 5 BR, 3.5 bath, three-story single-family with third floor master suite and finished basement. Features hardwood floors, chef's kitchen with stainless steel appliances, and recessed lighting. Spacious living room and formal dining room. In-unit laundry, beautifully tiled bathrooms with jacuzzi tub. Large rooms with ample closet space, outdoor space, with two car garage and off-street parking. Convenient location with many area amenities. Minutes from Forest Hills T stop and Roslindale Village Commuter Rail. Bus routes 30, 34, 34E, 40, and 50. Utilities are not included. Move-in costs include first + last month's rent, and security deposit, background + credit check fee. NO SMOKING. PETS CONSIDERED. REFERENCES REQUIRED. Some photos have been virtually staged to illustrate potential furniture placement; the property will be delivered vacant and unfurnished

339 Poplar St., Boston

Listing courtesy of Listing Agent: Yvette Blinker from Listing Office: MIG.

$710,000

5 Beds ⋅ 3 Baths ⋅ 73524706 MLS

Neighborhood charm with city convenience! Recently renovated and thoughtfully updated, this spacious single-family home offers the perfect blend of functionality & convenience across three levels of living. Featuring 5 beds and 2.5 baths, the home boasts a flexible floor plan ideal for growing families, multigenerational living, or investment potential. The bright, open living area flows seamlessly into the updated kitchen complete with stainless steel appliances, granite countertops, & ample cabinetry designed for both everyday living and easy entertaining. Additional highlights include first-floor laundry, full basement with bulkhead access, private backyard perfect for outdoor gatherings & off-street parking for up to 3 vehicles. Located near Roslindale Village’s popular restaurants, shops, parks, & public transportation, including easy access to the Forest Hills MBTA station and downtown Boston. Property is currently leased & will be delivered with tenant in place through 2/28/27.

737 American Legion Hwy, Boston

Listing courtesy of Listing Agent: Maher Realty Group from Listing Office: eXp Realty LLC.

$899,000

5 Beds ⋅ 2 Baths ⋅ 73498213 MLS

New Price! Bring your contractors and ideas!!! Perfect for condo conversion each with a garage bay. Sitting high and pretty with seasonal city views. Light and bright, 9' ceilings, spacious rooms, diamond in the rough! Perfect for condo conversion or multi-generational living situation. Original kitchens and baths. Mellow hardwood floors in most rooms, loaded with original charm. Solar panels are owned and service the 2nd floor. 1st floor is now vacant 10/3/2026. 2 car garage on Cornell St. Pull down stairs to the attic with good height. Excellent ceiling height in basement great for storage or further expansion. Moments to commuter rail and shops! Fabulous parkway location close to all that Roslindale and West Roxbury has to offer. All photos with no furniture are of 2nd floor.1st floor does not have solar panels. Roof 2010, solar panels 2014, gas water heaters 2018, gas heating systems approx 20 yrs young.

73 Westbourne St, Boston

Listing courtesy of Listing Agent: Maureen Hayes Rossi from Listing Office: Vogt Realty Group, LLC.

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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.

Roslindale, Boston, MA 5 Bedroom Homes for Sale

Newest Roslindale, Boston, MA 5 Bedroom Homes for Sale

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