Homes With 2 Car Garage In Roslindale, MA

PONDSIDE Jamaiica Plain Single-Family Opportunity! More Photos coming! After more than 40 years in the same family, 52 Prince Street is ready for its next chapter. This charming 4-bedroom, 1.5-bath Colonial offers approximately 1,550 sq. ft. of living space, a generous 4,300+ sq. ft. lot, a standing detached garage, and additional parking - an exceptional combination in Boston. Recent improvements provide a great starting point for the next owner, including refinished wood flooring, freshly painted rooms, and a newer roof approximately two years old. The home retains its classic character with a traditional layout while offering plenty of opportunity to bring your own vision, style, and updates. Living room, dining room, kitchen and extra bedroom/office plus half bath complete the first floor. Second floor has 3 bedrooms and a bath and attic access. Ideally located Pondside, in the heart of Jamaica Plain, this home offers convenient access to neighborhood shops, restaurants, cafes, the Arboretum, and Jamaica Pond. Public transportation and nearby routes make commuting to Downtown Boston and the Longwood Medical Area convenient, putting many of Boston’s hospitals, universities, and cultural destinations within easy reach. Whether you are looking for a long-term family home, a well-located city property, or an opportunity to create something truly your own, 52 Prince Street offers a rare opportunity to put your touch on this Pondside gem.

52 Prince St, Boston

Listing courtesy of Listing Agent: Andrew Brilliant from Listing Office: Gibson Sotheby's International Realty.

$849,000

2 Beds ⋅ 2 Baths ⋅ 73573599 MLS

Score the best of both worlds in this rarely available, direct-access townhouse set on a private street in the epicenter of JP! Located literal steps to restaurants, cafes, shops and public transit, with the luxury of 2-car garage parking & tranquility of Parley Vale Preserve. Unit offers private front & garage entrances, hardwood floors, architecturally striking details, wood-burning fireplace, central air + significant updates. Kitchen boasts newer SS appliances, built-in pantry/coffee station, elegant breakfast nook & shared deck. On the 2nd floor, the guest bed has double closets and private balcony. Primary bedroom wows with dramatic vaulted ceilings, skylight + sprawling 375 sq ft loft, adorned w/ copious built-ins and a wet bar. This room is perfect for a home office, yoga/gym, media room or flex guest space. Laundry + room for storage and bikes are in the 2-car garage beneath the unit. Tight-knit HOA shares regular get-togethers, plus a lovely central patio, garden areas and 3 designated guest parking spaces on the street. Unbeatable location only .3 miles to the Pond, .6 miles to Green St T, 5 mins to Whole Foods + proximity to JP’s abundant treasures and green space.

11 Parley Ave Unit 11B, Boston

Listing courtesy of Listing Agent: Christian Iantosca Team from Listing Office: Arborview Realty Inc..

$2,249,999

5 Beds ⋅ 4 Baths ⋅ 73568180 MLS

Privately nestled on one of Jamaica Plain's most distinguished residential streets, 5 Moss Hill Road presents a rare opportunity to own a timeless brick Colonial in the highly sought-after Moss Hill neighborhood. Blending classic architecture with thoughtfully updated interiors, this exceptional residence offers over 3,100 square feet of refined living space designed for both elegant entertaining and everyday comfort.A welcoming foyer leads to gracious living and dining rooms filled with natural light, rich hardwood flooring, and architectural details that reflect the home's enduring character. At the heart of the residence is a beautifully renovated kitchen featuring quartz countertops, premium appliances, a generous center island, and seamless access to multiple outdoor living spaces. The covered porch, expansive deck, and professionally landscaped grounds create an effortless indoor-outdoor lifestyle ideal for gatherings or quiet relaxation.The upper levels offer five spacious bedrooms, including a serene primary suite complete with a private balcony and spa-inspired bath. Additional balconies, flexible guest accommodations, and a finished lower level provide versatile space for a recreation room, fitness studio, media room, or home office to meet today's evolving lifestyle needs.Perfectly positioned between Brookline and Jamaica Plain, Moss Hill is one of Boston's most coveted residential enclaves, celebrated for its tree-lined streets, estate-style homes, and exceptional access to the city's finest amenities. Enjoy close proximity to the Longwood Medical Area, Centre Street's acclaimed restaurants, cafés, and boutiques, the Arnold Arboretum, Jamaica Pond, and the Emerald Necklace park system, while remaining just minutes from Downtown Boston, Back Bay, Fenway, major universities, and convenient public transportation.Offering an exceptional balance of privacy, character, modern functionality, and an unparalleled location, 5 Moss Hill Road represents a rare opportunity to own a distinguished residence in one of Boston's most established and desirable neighborhoods.

5 Moss Hill Rd, Boston

Listing courtesy of Listing Agent: The Boston ONE Team from Listing Office: Serhant.

$1,895,000

4 Beds ⋅ 3 Baths ⋅ 73545634 MLS

Newly completed and ready to impress, this standout new construction home blends modern design with effortless style. The open main level is made for today’s living and entertaining, featuring a sleek chef’s kitchen with an oversized island, premium appliances, custom cabinetry, and a seamless flow into the spacious living area with a gas fireplace and crisp contemporary finishes. A stylish den with designer millwork adds valuable flexibility for a home office, media room, or lounge. Upstairs, the airy primary suite offers generous walk-in closets and a spa-like bath with elevated finishes. Three additional bedrooms share a chic hall bath with modern details. Enjoy outdoor living with a private patio, landscaped yard, and the convenience of a two-car garage. With multi-zone heating and cooling, oversized windows, fresh curated finishes, and low-maintenance new construction ease, this home delivers high-impact style in an ideal location near the Arnold Arboretum and the city

12 Allandale Street, Boston

Listing courtesy of Listing Agent: Rosemar Realty Group from Listing Office: Insight Realty Group, Inc..

$1,149,000

2 Beds ⋅ 3 Baths ⋅ 73537902 MLS ⋅ ['Cabot Estate'] BLDG.

Enjoy spectacular sunset views from this stunning penthouse in Cabot Estate's gated community. Bright and spacious, this 2-bedroom, 2.5-bath home spans three levels and includes a versatile loft ideal for a home office/library, and additional storage. The main level features an open living/dining area with floor-to-ceiling windows, wood floors, wood-burning fireplace, and French doors leading to a private balcony. The updated kitchen offers a breakfast bar, stainless steel appliances, and custom cabinetry. A spiral staircase leads to the lower level with a primary bedroom featuring an en suite bath and walk-in closet, a second bedroom with built-ins, a full guest bath, and a second balcony. Additional highlights include in-unit laundry, two tandem garage spaces with storage lockers, and a separate walk-in storage closet. Amenities include tennis courts, a pool, fitness center, library, and clubroom. Conveniently located across from Jamaica Pond and near Longwood, shops, restaurants.

241 Perkins Unit C603, Boston

Listing courtesy of Listing Agent: Beverly Berman from Listing Office: Gibson Sotheby's International Realty.

$2,195,000

4 Beds ⋅ 4 Baths ⋅ 73524195 MLS

Welcome to this newly constructed 4 bed 3.5 bath architectural masterpiece, where sophisticated design meets unparalleled craftsmanship. Located in Jamaica Plain, one of the city’s most sought after communities, offering the perfect blend of city convenience and suburban comfort. The expansive open concept main floor features oversized windows, rich hardwood floors that flow seamlessly throughout. A chef’s culinary kitchen serves as the heart of the home, boasting custom cabinetry and a striking waterfall island. Outside, a landscaped, fenced yard with a custom patio stands ready for entertaining. Modern high energy efficiency design, two-car garage. This premier location is close to top-rated schools, offers an effortless downtown commute, provides quick access to nearby major medical hubs, and sits just steps from the scenic trails of the historic Arnold Arboretum.

2 Brownson Terrace, Boston

Listing courtesy of Listing Agent: Rosemar Realty Group from Listing Office: Insight Realty Group, Inc..

$1,575,000

4 Beds ⋅ 4 Baths ⋅ 73522135 MLS

Secluded on a calm, closed-end JP street, 1 Lennoco Rd is a striking architectural gem blending historic exterior charm with a massive 2021 renovation & addition. This home instantly captures your attention with its steep front gables, artisan Craftsman timber accents, and breathtaking, sweeping cat-slide roofline framing a whimsical garden archway. Abutting an urban wild and cemetery, this private oasis features nearly new systems: Hardie siding, roof, windows, brand new deck, spray-foam, and 4-zone Heat Pump HVAC. Main level boasts open formal living/dining, massive kitchen, cozy family room with sliders out to side deck abutting Urban Wild wilderness. Rare layout puts all 4 bedrooms on the 2nd floor, including a primary suite with 4-piece bath, double vanity, and 2 walk-in closets. Lower level offers direct entry from a 2-car garage with EV charger, mudroom, 3rd full bath, and a flexible room ideal for a home office, gym, or guests. Unmatched tranquility just minutes from Forest Hills T, Arnold Arboretum, Franklin Park. Recently installed new deck.

1 Lennoco Rd, Boston

Listing courtesy of Listing Agent: Christian Iantosca Team from Listing Office: Arborview Realty Inc..

$2,595,000

8 Beds ⋅ 3 Baths ⋅ 73520401 MLS

Rare mixed-use investment opportunity in the heart of Jamaica Plain’s vibrant South Street corridor. This three-unit condominium building features a well-established bakery/café operating since 2004 with a licensed 20x20 patio, alongside two spacious four-bedroom residential units with covered porches. Property offers flexible use and strong income potential, with projected rents of $15,000–$18,000/month with business in place. Commercial space includes walk-in freezer and high-ceiling basement with expansion potential. Additional highlights include updated 400-amp electrical, FHA gas heat, two-car garage, and option to deliver with or without business. Business can be relocated and residential units can be delivered vacant. Plans for four units plus rear townhouse to transfer. Prime location near the Monument, Arboretum, and local shops. Ideal for investors, end users, or redevelopment.

55 South St, Boston

Listing courtesy of Listing Agent: Riley Walters from Listing Office: eXp Realty LLC - Corporate Office.

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Homes With 2 Car Garage In Roslindale, MA

Explore homes with 2 car garages in Roslindale, MA, offering the perfect combination of space, convenience, and suburban comfort. Whether you're seeking extra room for vehicles, storage, or a home workshop, these properties provide functional layouts without sacrificing style. Many feature updated kitchens, private yards, and easy access to Roslindale Village and commuter rail options.

Roslindale continues to attract buyers with its mix of classic New England charm and urban accessibility. From quiet cul-de-sacs to vibrant streets near shops and cafes, homes with attached or detached 2-car garages give buyers added flexibility and long-term value.

At MA New Listings | Coldwell Banker, we specialize in helping clients find Roslindale homes with 2 car garages that meet their unique needs. Whether you’re upsizing, relocating, or investing, our local expertise ensures a smooth home search and buying experience. Contact us today to explore available listings and make your move in Roslindale.

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Call Jason Niles, REALTOR® – Coldwell Banker Realty, or Abby Niles, REALTOR® – Coldwell Banker Realty, to start your real estate journey today!