Jamaica Plain Homes under $2 million

Welcome to Jamaica Plain, a vibrant neighborhood nestled in the heart of Boston, Massachusetts. Known for its lush green spaces, eclectic culture, and rich history, Jamaica Plain offers an inviting atmosphere that appeals to families, young professionals, and everyone in between. With its tree-lined streets and a strong sense of community, this charming area is a hidden gem that perfectly balances urban living with a suburban feel.

One of the standout features of Jamaica Plain is its beautiful parks, including the renowned Jamaica Pond and the expansive Franklin Park, both of which provide residents with ample opportunities for outdoor recreation. You can enjoy leisurely strolls, picnics, or even a refreshing paddle on the pond. The neighborhood also boasts a thriving arts scene, with local galleries, music venues, and community events that celebrate its diverse culture.

For those looking to make Jamaica Plain their home, the real estate market offers an array of options under $2 million. Here, you can find beautifully renovated Victorian homes, cozy condos, and charming single-family residences that cater to various tastes and lifestyles. With its convenient access to public transportation, residents can easily commute to downtown Boston while enjoying the tranquility of suburban life.

Whether you’re drawn to the rich history, the vibrant community, or the stunning homes, Jamaica Plain is a place where you can truly thrive. Discover your dream home in this enchanting neighborhood, and become part of a community that celebrates life in all its colorful forms!

Newest Jamaica Plain Homes under $2 million

$585,000

1 Beds ⋅ 1 Baths ⋅ 73587694 MLS ⋅ ['American Brewery Lofts'] BLDG.

Welcome to the American Brewery Lofts! This inviting 1-bedroom, 1-bath condominium offers comfortable living in a beautifully converted historic building. The open layout features high ceilings, in-unit laundry, central air conditioning, and a spacious kitchen. Enjoy peaceful views of the landscaped courtyard from the living space. The building offers elevator access, garage parking, fitness room, and professionally maintained common areas. Ideally located just moments from the Heath Street T, with easy access to Longwood Medical Area and Boston’s major hospitals, Brookline Village, Jamaica Plain, shops, restaurants, and parks. A wonderful opportunity to enjoy charm and character in a convenient, vibrant setting.

251 Heath St Unit 217, Boston

Listing courtesy of Listing Agent: Fran Hoy from Listing Office: Coldwell Banker Realty - Brookline.

$1,475,000

9 Beds ⋅ 3 Baths ⋅ 73587503 MLS

A turnkey 3-family home in a highly desirable Jamaica Plain location. This 3,144-square-foot, 5/5/5, 3-bedroom-unit property offers a versatile option for owner-occupants, investors, buyers pursuing a 1031 exchange, or developers seeking a reliable asset in a sought-after area—just minutes from City Feed, the Stony Brook T Stop, and the Southwest Corridor.

177 Chestnut Avenue, Boston

Listing courtesy of Listing Agent: Stephen Lussier from Listing Office: Arborview Realty Inc..

$799,000

3 Beds ⋅ 2 Baths ⋅ 73587167 MLS

Welcome to this beautifully designed, newly constructed top-floor condominium offering 3+ bedrooms and 2 full bathrooms. The bright, open-concept living space is centered around a stylish chef’s kitchen with gas stove, creating an ideal setting for both everyday living and entertaining. This unit has a welcoming dining room off the living area with large almost wall to wall windows. The spacious primary suite features a private ensuite bathroom, while the second generously sized bedroom offers double closets. A bright third bedroom with balcony provides additional flexibility, can easily serve as a home office, study, gym, or whatever best suits your lifestyle. Additional features include an in-unit stackable washer and dryer, central air conditioning, Wood style flooring throughout, and premium stainless steel appliances. The unit is lead-free and includes one off-street parking space. With modern finishes, abundant natural light, and a versatile layout, this home combines comfort, convenience, and contemporary living.

3247 Washington Unit 3, Boston

Listing courtesy of Listing Agent: Focus Team from Listing Office: Focus Real Estate.

$1,500,000

8 Beds ⋅ 6 Baths ⋅ 73587007 MLS

Fully tenanted, cash-flowing and just three blocks from the Stony Brook T, this three-family built in 2006 offers a standout investment in one of Jamaica Plain's best locations. Offering three spacious residences and four off-street parking spaces, 164 Boylston combines the benefits of newer construction with meaningful future upside to increase cash flow. The unit mix includes one 2-bedroom, 2-bath residence and two 3-bedroom, 2-bath residences. Each features a primary bath, granite countertops, stainless steel appliances, central air, in-unit laundry, and separately metered heat, hot water and electricity. The second and third floor residences each enjoy a private rear balcony, while the first-floor unit is wheelchair accessible. Additional amenities include three large private basement storage rooms, individual power-vented hot water tanks and a building-wide sprinkler system. Fully tenanted, the property currently generates $10,375 per month and $124,500 annually in gross rental income. Current rents are below market rent, providing an opportunity to increase income over time while the property is already producing positive cash flow at today's rents. Projected rents for the 2027/2028 rental cycle total $11,700 per month and $140,400 annually, representing approximately $15,900 in additional annual gross rental income as leases turn over. The location also offers convenient access to the Longwood Medical Area, one of Boston's major employment and education centers. Closer to home, residents enjoy easy access to the Orange Line, Southwest Corridor, Café Ula, Chilacates, Mike's Fitness, the Sam Adams Brewery, Jamaica Pond, Franklin Park and Jamaica Plain's extensive collection of restaurants, shops and neighborhood amenities. A compelling opportunity to acquire a turnkey, cash-flowing multifamily property with parking, modern systems, strong in-place income and meaningful long-term upside in one of Boston's most established rental markets.

164 Boylston Street, Boston

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

$574,900

2 Beds ⋅ 2 Baths ⋅ 73586480 MLS

Bright, open and spacious, this sun-filled 2+ bedroom condo combines generous living space with TWO CAR PARKING! The 1,066 sq. ft. first floor features two good-sized bedrooms, a full bath and an open kitchen, dining and living area. Freshly painted with hardwood floors throughout, the first floor is highlighted by an updated kitchen with granite countertops, an oversized peninsula, a wall oven and gas cooking. The lower level provides additional bonus space, a second full bath and a dedicated laundry room with storage. Other features include a large basement storage area, shared yard and new water heater (2026). Pet-friendly association with a low $200 monthly condo fee! Enjoy nearby Centre Street shops and cafés, Whole Foods, Tres Gatos, Mozart Park and the Southwest Corridor. Jackson Square’s Orange Line offers easy access to downtown Boston, with the Longwood Medical Area also within reach. Walk Score 88 and Bike Score 91. Don’t let this one get away.

22-24 Estrella St Unit 1, Boston

Listing courtesy of Listing Agent: The Mavroules Team from Listing Office: Good Deeds Realty Partners.

$1,199,000

6 Beds ⋅ 2 Baths ⋅ 73586352 MLS

Offered for the first time in more than 60 years, 15 Peter Parley Road presents a rare opportunity to own a well-maintained two-family residence in Jamaica Plain. Built in 1905, this family-owned property combines original architectural details with flexible living space and future possibilities.The home offers approximately 2,828 square feet of living space and includes a framed third-floor area that may provide expansion opportunities, subject to buyer verification and applicable approvals. The property features six bedrooms and two full bathrooms across two levels.Situated on a 6,355-square-foot lot, the property is conveniently located near Franklin Park, Green Street MBTA Station, shopping, dining, and neighborhood amenities. New decks overlook the private, level backyard, providing additional outdoor living space.Original character is evident throughout the home, including hardwood floors, built-in cabinetry in the living and dining rooms, walk-in pantries, solid wood interior doors with original hardware, and front and rear common stairways.Nearby recreational destinations include Franklin Park Zoo, William J. Devine Golf Course, Arnold Arboretum, and Jamaica Pond. The flexible floor plan, preserved period details, and expansion potential make this a unique opportunity in one of Boston's most vibrant neighborhoods.

15 Peter Parley Rd, Boston

Listing courtesy of Listing Agent: Andrew Lane from Listing Office: Bantry Way Brokerage.

$1,099,000

7 Beds ⋅ 2 Baths ⋅ 73585263 MLS

LOCATION,LOCATION,LOCATION !!! New exciting listing! Charming and rarely available two-family house in a prime and much-desired Monument location, directly across from Curtis Hall. The 1st floor unit, filled with natural light, includes 2 good sized bedrooms, formal living room and dining room with gorgeous original wood period moldings including stately beamed ceilings and lovely hardwood floors! Unit 2 has two generous floors of living space with formal living room and dining room with more gorgeous natural woodwork. The 3rd floor has 3 terrific rooms offering you many options for bedrooms, family rooms or home offices! 2 Car off-street tandem parking spaces! Younger gas heating systems. Replacement windows! Rear porches offer comfortable outdoor relaxation! Proudly offered and ready for you! Please see attached floor plan.

9 South St., Boston

Listing courtesy of Listing Agent: The stevedoug.com Team from Listing Office: LAER Realty Partners.

$600,000

2 Beds ⋅ 1 Baths ⋅ 73585057 MLS ⋅ ['99 St Rose St Condominium'] BLDG.

Experience urban convenience and green space side by side in this sunny Arborway sanctuary, located just blocks from the Arnold Arboretum. Converted in 2016, this inviting two-bedroom, one-bathroom condo balances classic character with modern efficiency.The functional layout features hardwood floors, distinct living and dining spaces, classic built-ins, and a traditional butler's pantry. The kitchen comes fully equipped with granite countertops, maple cabinetry, and stainless steel appliances. Everyday conveniences include dedicated laundry, a clean full bathroom, dedicated basement storage, and the rare bonus of a private garage parking space. Step outside to a deck, backyard and garden beds. Major upgrades provide long-term peace of mind, including fresh exterior paint, a roof that was replaced two years ago, with windows, high-efficiency tankless hot water and boiler systems installed during the 2016 building conversion. Sitting less than 1/4 mile from South St's shopping and bus stations, and under 1/2 mile to the Forest Hills T station, you'll also enjoy easy access to local parks, transit, and the vibrant boutiques and restaurants along Centre Street. Showings begin during Sunday's open house from 1-3!

99 Saint Rose St Unit 1, Boston

Listing courtesy of Listing Agent: Victoria Keith from Listing Office: Board and Park.

$914,900

3 Beds ⋅ 2 Baths ⋅ 73584819 MLS

Don't miss this beautifully maintained 3 Bed / 2 Full Bath condominium in the heart of Jamaica Plain! This sun-filled home features an inviting open-concept layout with hardwood floors, high ceilings, recessed lighting, and a gas fireplace. The spacious kitchen offers granite countertops, stainless steel appliances, new refrigerator and dishwasher, gas cooking, and a breakfast bar ideal for entertaining. The generously sized primary suite features a recently renovated private en-suite bath, while two additional bedrooms provide excellent flexibility for guests, a home office, or additional living space. Additional highlights include brand-new central air conditioning, new in-unit laundry, abundant private storage, two private decks, and off-street parking. Set within a well-managed association, this home offers an exceptional combination of comfort, convenience, and location. Enjoy easy access to Jamaica Plain's vibrant shops, restaurants, and parks, as well as the Southwest Corridor, Franklin Park, and multiple T-stations. A wonderful opportunity to enjoy everything Jamaica Plain has to offer!

16A Meehan Unit 2, Boston

Listing courtesy of Listing Agent: Christopher Buono from Listing Office: All Things Real Estate, Inc..

$1,275,000

3 Beds ⋅ 3 Baths ⋅ 73584707 MLS

One of six sophisticated new condominium residences in the heart of Jamaica Plain, where timeless architectural character meets refined modern living. This unit offers approximately 1,335 SF with 3 bedrooms, 2.5 baths, and an inviting open-concept design. Exceptional craftsmanship and quality are evident throughout, highlighted by premium Drutex tilt-and-turn windows that bring abundant natural light, European-inspired design, and exceptional functionality to the home. The light-filled living and dining areas feature engineered hardwood flooring, soundproofing, and recessed lighting. The stunning kitchen showcases contemporary cabinetry with quartz countertops and stainless-steel appliances. The spacious primary suite features a luxurious full bath with heated floors and custom-built closets, with two additional bedrooms offering flexibility for guests or home office use. Central air, whisper quiet condenser units, in-unit laundry, and one off-street parking space complete this exceptional offering.

305 Chestnut Ave Unit 4, Boston

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

$975,000

2 Beds ⋅ 3 Baths ⋅ 73584449 MLS

Urban Living with Income Potential! Steps from the Orange Line. This versatile home works beautifully as a single-family retreat or a two-family income property. Located just a quarter mile from Green Street Station on the Orange Line, commuting couldn't be easier.The property features 2 bedrooms, 3 bathrooms, a finished basement with with full bathroom and washer & dryer. A beautifully maintained outdoor yard with fire pit— perfect for relaxing or entertaining. Set on a premium block just steps from Jamaica Plain's iconic Painted Lady Victorian homes. You are also minutes from JP's best amenities: basketball and tennis courts, baseball fields, gyms, multiple playgrounds, a community center, the public library, the SW Corridor Bike Path, the Arboretum, Jamaica Pond, and Centre Street's shops and restaurants. If owner occupied, property tax will be $4350 less.

40-40A Newbern, Boston

Listing courtesy of Listing Agent: Andrei Ganea from Listing Office: David W. Elliott.

$1,249,000

7 Beds ⋅ 3 Baths ⋅ 73584438 MLS

A rare multi-family opportunity in one of Jamaica Plain’s most desirable neighborhoods, where properties of this caliber seldom become available. Ideal for investors, developers, or owner-occupants alike, this family-owned home has been treasured for decades and is now ready for its next chapter. Built at the turn of the century, the property offers the character, scale, and solid construction of an earlier era, with a total of seven bedrooms and three full baths. The location is exceptional, just moments from Green Street Station on the MBTA Orange Line, two doors away from the recently revitalized Flaherty Park, and perfectly positioned between the Centre Street and Washington Street business corridors. Beyond its existing layout, the property offers compelling upside through the thoughtful reimagining of underutilized space, with the possibility of exploring an ADU or third-unit expansion, subject to applicable zoning and approvals. Enjoy convenient access to Jamaica Pond, the Arnold Arboretum, Sam Adams Brewery, downtown Boston, neighborhood restaurants, boutique shops, and public transportation. A truly special offering that combines location, flexibility, character, and long-term potential in the heart of Jamaica Plain.

6-8 Marmion St, Boston

Listing courtesy of Listing Agent: Stonehurst RE Group from Listing Office: Keller Williams Realty Evolution.

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