Jamaica Plain Homes for Sale

Welcome to Jamaica Plain, a vibrant neighborhood nestled in the heart of Boston, Massachusetts. Known for its rich history, diverse culture, and stunning natural beauty, Jamaica Plain offers an unparalleled living experience that appeals to families, young professionals, and everyone in between. With its tree-lined streets, historic brownstones, and charming single-family homes, this area is a perfect blend of urban convenience and suburban tranquility.

Jamaica Plain is home to a dynamic community that celebrates its diversity through a variety of local events, farmers' markets, and cultural festivals. The neighborhood boasts an array of parks, including the expansive Jamaica Pond and the picturesque Arnold Arboretum, providing residents with ample opportunities for outdoor activities and relaxation. The area is also known for its eclectic mix of shops, cafes, and restaurants, ensuring that there's always something new to discover.

For those considering a move to Jamaica Plain, the real estate market is as inviting as the community itself. Homes for sale in this charming neighborhood range from beautifully restored Victorian houses to modern condos, catering to a variety of tastes and budgets. Whether you’re searching for a cozy starter home or a spacious property for your growing family, Jamaica Plain has something to offer everyone.

With its convenient access to public transportation, top-notch schools, and a strong sense of community, Jamaica Plain is more than just a place to live—it's a place to thrive. Explore the homes for sale in this vibrant neighborhood and discover why so many people are proud to call Jamaica Plain their home.

Newest Jamaica Plain Homes for Sale

$1,950,000

6 Beds ⋅ 3 Baths ⋅ 73599053 MLS

Every now and again, a grand residence from an earlier era comes to market, seeking a new steward to carry its history forward. This impressive Queen Anne Victorian home on historic Sumner Hill yearns for restoration. Twelve gracious rooms offer artisan-crafted woodwork & period details throughout. A dramatic entry foyer features ornate wood-framed arches, a fireplace with an elaborate mantel and lift-top bench, tall wainscoting, stained glass, and a sweeping staircase. Beyond, double parlors showcase pocket doors, bay windows, a petite plant solarium, fireplaces in each room, and inlaid oak floors. Off the kitchen, the formal dining room boasts a built-in sideboard, another fireplace, and direct access to the rear deck. Sleeping quarters above comprise six bedrooms with wood flooring, some highlighted by bay windows and fireplaces, along with two full baths, and a generously sized primary bedroom with charming covered porch and balcony. Additional features include original decorative windows, abundant built-ins, a unique linen room with a wall of cabinetry and a cedar closet on an upper floor, and remnants of the original scullery on the lower level. The grounds hold the promise of a lovely yard and gardens. The western side of the house fronts on a private way, creating off-street parking among an intimate enclave of neighboring homes. Sumner Hill is listed on the National Register of Historic Places. Once part of a vast tract of land known as the Greenough Estate, the property was subdivided in the late 1800’s. A cluster of architecturally significant homes was built throughout the hill at that time, many owned by prominent figures who helped shape Boston’s economic and social landscape. Today, Sumner Hill remains highly sought-after for its beautifully restored residences and proximity to Jamaica Plain’s cultural and natural treasures, along with its many notable restaurants and shops. Come make this your dream home!

21 Greenough Avenue, Boston

Listing courtesy of Listing Agent: Janet Deegan from Listing Office: Coldwell Banker Realty - Boston.

$1,450,000

3 Beds ⋅ 2 Baths ⋅ 73598629 MLS

Welcome to spectacular Jamaica Plain! Offering approximately 2,700 square feet of thoughtfully designed living space, this exceptional home combines timeless character, beautifully updated interiors, and an enviable setting. A 2006 renovation transformed the home, creating a stunning gourmet kitchen featuring slate flooring, custom Crown Point cabinetry, a butcher block island, Wolf stove, and even a pizza oven—perfect for both everyday living and entertaining. The renovation also included a wonderful family room addition just off the kitchen, creating a warm and inviting gathering space. Additional finished space in the basement provides flexibility for a home office, playroom, gym, or media room. Outside, an amazing corner lot offers an incredible backyard and a rare sense of privacy, creating a peaceful retreat in the heart of vibrant Jamaica Plain. A truly special opportunity to enjoy generous living space, exceptional amenities, and a remarkable outdoor setting in one of Boston's most desirable neighborhoods.

58 Union Ave, Boston

Listing courtesy of Listing Agent: Matthew Bagnell from Listing Office: Coldwell Banker Realty - Milton.

$749,900

3 Beds ⋅ 1 Baths ⋅ 73595629 MLS

Renovated single-family townhouse near the Arnold Arboretum, Jamaica Pond, and the shops and restaurants of Centre Street. The main level features a sun-filled living room and a spacious eat-in kitchen with granite countertops, stainless-steel appliances and an abundance of cabinet space. Upstairs are three bedrooms with hardwood floors and ample closet space, plus a full bath. The finished lower-level bonus space is currently used as a home gym. Enjoy private outdoor space with newer pavers, grilling area, and room to garden. Additional features include central A/C, two deeded parking spaces, and a roof installed in 2025. Solar panels are rented. Also listed under MLS #73600325.

22 Goldsmith St., Boston

Listing courtesy of Listing Agent: Patricia Reilly from Listing Office: RE/MAX Real Estate Center.

$899,900

4 Beds ⋅ 3 Baths ⋅ 73595385 MLS

**Prime Jamaica Plain Location with Incredible Potential!** Opportunity awaits at 244 Jamaicaway! Situated on a desirable corner lot in one of Boston’s most sought-after neighborhoods, this spacious single-family home offers over 2,700 square feet of living space and endless possibilities for investors, renovators, or buyers looking to create their dream home. Featuring a finished basement, an expansive third-floor bonus room, and multiple flexible spaces ready for your vision. The property also offers off-street parking, a yard, and outdoor space—a rare combination in the city. Enjoy a prime location near Jamaica Pond, the Emerald Necklace, Longwood Medical Area, local shops, restaurants, and public transportation. With its generous footprint, flexible layout, and exceptional location, this property presents an exciting opportunity to renovate, reimagine, and unlock its full potential. Bring your vision and make it your own!

244 Jamaicaway, Boston

Listing courtesy of Listing Agent: Brian Gagnon from Listing Office: Coldwell Banker Realty - Boston.

$1,395,000

6 Beds ⋅ 2 Baths ⋅ 73593621 MLS

Offered for the first time in more than 50 years, 9 Newbern Street is a substantial Sumner Hill home, rich with history, original architectural detail and extraordinary potential. Lovingly held by the same family since 1971—and the place where 11 children were raised—the home now awaits its next chapter. Set up on the hillside with a welcoming covered front porch, a gracious center staircase, coved plaster ceilings in the living and dining rooms and six bedrooms spanning the second and third floors provide the bones for a truly special restoration. The home offers a rare opportunity to thoughtfully reimagine a large, character-filled central Jamaica Plain residence.

9 Newbern Street, Boston

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

$2,100,000

3 Beds ⋅ 3 Baths ⋅ 73591002 MLS

Come home to an exceptional Pondside custom-crafted Condominium by renowned local artisan Maple Hurst Builders. A private entrance opens to a gracious foyer and a residence that offers the comfort and ease of a single-family home. High ceilings, glistening wood floors, abundant windows, and an elegant flow of living and entertaining spaces create an inviting sense of light and scale. The main living level features a handsome library, living room with fireplace, chef’s eat-in kitchen, formal dining room, study, and a powder room. Architectural details abound, from graceful columns and crown moldings to built-in bookcases and custom cabinetry throughout. The upper level is devoted to restful quarters, including a generous primary suite with fireplace, well-appointed 4-piece bath & a deep walk-in closet, an additional bedroom, a second full bath, and glass doors opening onto an elevated private deck. The top floor offers two expansive, versatile rooms & kitchenette with the possibility of a getaway bedroom suite, home office, exercise studio, or whatever your creative pursuits. Outside, established gardens and mature trees create a serene setting, with a charming trellised brick walkway leading to the garage parking and additional off-street spaces. All this in a coveted Jamaica Plain location, just one block from the neighborhood’s vibrant mix of restaurants, shops, cultural destinations, and the natural beauty of Jamaica Pond along Olmsted’s Emerald Necklace. A distinctive home in an extraordinary setting—look no further.

55 Burroughs Street Unit 55C, Boston

Listing courtesy of Listing Agent: Janet Deegan from Listing Office: Coldwell Banker Realty - Boston.

$1,395,000

4 Beds ⋅ 5 Baths ⋅ 73583887 MLS

DISCOVER A TRULY EXCEPTIONAL OPPORTUNITY IN PRIME MOSS HILL. This elegant, sun-drenched spilt entry colonial boasts a thoughtfully designed, versatile floor plan spanning four expansive levels of living space. On the main level, an inviting fireplace-warmed living room leads to a cozy den w/skylights, a newer full bathroom w/walk in shower, and a luminous, spacious kitchen equipped with skylights and generous counter space. The adjoining dining area features its own cozy fireplace and a captivating wall of windows, seamlessly transitioning to a deck—ideal for basking in morning light or hosting evening gatherings. The second floor offers 3 spacious bedrooms, including a flexible ensuite with a private bath, alongside a stylishly updated full hall bath. The top level serves as a serene, sunlit primary suite complete with skylights and an updated bath. The lower level extends the living space with an multi-purpose family room, and direct outdoor access to the private backyard. This special home is conveniently situated near Jamaica Pond, vibrant JP Centre, and the Longwood Medical Area. A rare gem ready for its next owner!

130 Moss Hill Rd, Boston

Listing courtesy of Listing Agent: Bunny Cecchetto from Listing Office: Focus Real Estate.

$1,195,000

4 Beds ⋅ 3 Baths ⋅ 73581241 MLS

Across from the wooded lawn of the Eliot Art School, this Jamaica Plain single-family offers a view that changes with every season. Inlaid floors, original windows, and a front door with sidelights carry the home’s history forward. Bay windows brighten the living room, a formal dining room invites hosting, and a back family room awaits insulation to become a year-round space. Upstairs are two bedrooms, two full baths, a flex space, and two finished attic rooms for a studio, office, or guests. A separate entrance leads to a bedroom, bath, flex space, and kitchenette, offering options for extended family or independent living. The roof, windows, and exterior stairs need work, giving a buyer the chance to invest in a home whose character and location can’t be replicated. The home is close to Centre Street's shops and restaurants, Jamaica Pond, the Arnold Arboretum and everything JP has to offer. Homes like this, in this location, don't come around often!

38 Holbrook St, Boston

Listing courtesy of Listing Agent: The Muncey Group from Listing Office: Compass.

$1,849,000

4 Beds ⋅ 4 Baths ⋅ 73577476 MLS

Welcome home to this beautifully crafted, newer-construction home in the heart of Jamaica Plain’s coveted Sumner Hill Historic District — designed with distinctive eave brackets, high ceilings, and rich hardwood floors to respectfully echo the Italianate and Victorian character of its historic neighbors. This 4-bedroom, 3.5-bath home pairs period-inspired detail with a fully modern interior. The open floor plan flows effortlessly from a fireplaced living room into a well-appointed kitchen featuring Corian countertops and a handy office nook, perfect for remote work. Step directly from the kitchen onto the deck overlooking a lush perennial garden — a private retreat fully fenced for kids and pets. A first-floor laundry room and updated half bath add everyday ease. Upstairs are three bedrooms and two baths, including a generous primary suite with en-suite bath and walk-in closet. The finished ground floor includes a fourth bedroom and full bath — ideal as an au pair suite, home office, gym, or private guest space. Additional highlights include solar panels, abundant storage, and a rare 2.5-car garage. All this just a block from the Green Street Orange Line station and moments from JP’s eclectic shops, restaurants, parks, and green space — an exceptional combination of historic charm, neighborhood living, and easy access to downtown Boston.

75 Seaverns Ave, Boston

Listing courtesy of Listing Agent: Christman Johnsson Group from Listing Office: Hammond Residential Real Estate.

$670,000

3 Beds ⋅ 1 Baths ⋅ 73575753 MLS

Welcome to 19 Eastland Rd in Jamaica Plain! Located in a highly desirable neighborhood, this well-maintained home offers a great opportunity in one of Boston’s most vibrant and sought-after areas. Enjoy the many amenities Jamaica Plain has to offer, including great restaurants, shops, parks, green space, and convenient access to public transportation. The home itself is in great overall condition, while the kitchen has been fully gutted and is ready for a complete renovation, giving the next owner the opportunity to create a brand-new kitchen tailored to their taste and needs. With a solid foundation and an exceptional location, this home is a fantastic opportunity to bring your vision to life and make it your own.

19 Eastland Rd, Boston

Listing courtesy of Listing Agent: Jennifer Rossman from Listing Office: Carpe Diem Realty LLC.

$1,690,000

4 Beds ⋅ 3 Baths ⋅ 73574821 MLS

Beautifully updated brick and slate Dutch Grambel on Moss Hill that has all – classic period detail inside and out, modern systems, new baths and kitchen, large level back yard, PLUS private parking for 4 directly behind the home. The whole package! Imaging entertaining in a newly renovated eat-in kitchen w/ stainless appliances, sleek silestone counters, shaker cabinetry & herringbone tile backsplash…creating memories in a welcoming window-filled formal dining room…relaxing in a spacious and sunny fireplaced living room. Main level also offers a stylish ½ bath, and bedroom that could be used for office, guest, or play-space. Upstairs are a spacious primary suite w/updated bath, 2 large family bedrooms and a stylish new main bath. All bedrooms have walk-in closets! Can’t beat the lot – large mature trees, bucolic setting with stone patio, gardens, tree canopy in back. Central AC, 2022 boiler, copper gutters, great basement storage & the list goes on! Easy access to Longwood Medical, JP Center & Pond, Arnold Arboretum, shops, MBTA & Goddard Corridor private schools.

292 Pond, Boston

Listing courtesy of Listing Agent: The Gillach Group from Listing Office: William Raveis R. E. & Home Services.

$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.

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Jamaica Plain Homes for Sale

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