Jamaica Plain Real Estate

Jamaica Plain Real Estate

Welcome to Jamaica Plain, a vibrant and eclectic neighborhood nestled in the heart of Boston, Massachusetts. Known for its rich history, diverse culture, and stunning natural beauty, Jamaica Plain offers a unique blend of urban living and suburban charm.

One of the standout features of Jamaica Plain is its commitment to green spaces. The neighborhood is home to the renowned Arnold Arboretum, a 281-acre park that is part of the Emerald Necklace park system. Here, you can wander through beautiful gardens, discover a variety of plant species, and enjoy peaceful walks amidst nature. The nearby Jamaica Pond is another local gem, perfect for kayaking, jogging, or simply relaxing by the water's edge.

Jamaica Plain is also celebrated for its vibrant arts scene and community spirit. The area boasts an array of local boutiques, art galleries, and independent coffee shops, creating a lively atmosphere that invites creativity and connection. Residents and visitors alike can enjoy the neighborhood's diverse culinary offerings, ranging from farm-to-table restaurants to international cuisine that reflects the multicultural fabric of the community.

With a strong sense of community and a commitment to sustainability, Jamaica Plain is not just a place to live; it's a place to thrive. Its close-knit neighborhoods and active community organizations foster a welcoming environment, making it an ideal choice for families, young professionals, and retirees alike.

Whether you’re exploring the local parks, savoring a meal at a cozy café, or participating in community events, Jamaica Plain is a neighborhood that truly feels like home. Come discover the charm and character that make this Boston gem so special!

Newest Listings in Jamaica Plain

301 Chestnut Ave Unit 1, Boston
$899,999
2 Beds ⋅ 2 Baths ⋅ 73596668 MLS
Welcome home to this charming first-floor condo, blending classic character with modern convenience! Featuring 2 bedrooms, 1.5 baths, beautiful hardwood floors, high ceilings, and some original woodwork, this inviting home offers timeless appeal and a spacious, open floor plan ideal for everyday living and entertaining. The gourmet chef’s kitchen is the heart of the home, featuring a large pantry and a seamless flow into the dining and living room, creating a welcoming, connected space for gatherings and everyday living. Generously sized closets, in-unit laundry, and an exclusive basement storage area provide added convenience, while off-street parking for one car is a valuable bonus. Enjoy added peace of mind with a new furnace and water heater, both installed in 2026. Ideally located just one block from Centre Street’s vibrant shops, restaurants, and neighborhood favorites, with easy access to the T, this home offers the perfect combination of charm, comfort, and location. Enjoy all the conveniences of city living in a home full of charm and character! Note: The back porch and stairs are in the process of being replaced. No extra assessment was needed.

301 Chestnut Ave Unit 1, Boston

Listing courtesy of Listing Agent: David Foley from Listing Office: Realty Consultants of Cape Cod.
3 Round Hill St Unit 1, Boston
$899,000
4 Beds ⋅ 4 Baths ⋅ 73596640 MLS
Fantastic home in the heart this vibrant Jamaica Plain neighborhood! This spacious home offers the charm and character of classic Jamaica Plain with the style, flexibility, and updates today's buyers are looking for! The main level features an inviting open-concept living, dining, and kitchen area, plus an enclosed heated sunroom/laundry room, practical mudroom, and half bath. The eat-in kitchen offers a comfortable space for everyday living and entertaining. The second level offers two bedrooms, including a spacious primary suite with a generous walk-in closet/dressing room and full bath! The third level provides versatile additional living space that can be used as sleeping quarters, a family room, office, or play space. A finished lower level adds even more flexibility with an additional room ideal for a home office, guest space, or overflow living. Additional highlights include 3.5 bathrooms, solar panels, 2-car covered parking, and a charming private patio area. With multiple levels and flexible spaces, this home offers endless possibilities for growing, working, hosting, and living. Ideally located just minutes from the Southwest Corridor Park, Longwood Medical Area, Orange and Green Line T stops, Whole Foods, Stop & Shop, and many shops and restaurants. Come explore the possibilities and discover what makes this one-of-a-kind JP home such a special opportunity! Some photos digitally enhanced.

3 Round Hill St Unit 1, Boston

Listing courtesy of Listing Agent: Olivia Brown from Listing Office: Keller Williams Realty.
251 Heath St Unit 511, Boston
$948,000
2 Beds ⋅ 2 Baths ⋅ 73596450 MLS ⋅ ['American Brewery Lofts'] BLDG.
Historic character meets modern loft living at the American Brewery Lofts! This penthouse corner condo features soaring ceilings, exposed brick, bamboo flooring, oversized windows, and two skylights that welcome abundant natural light. The open kitchen offers stainless steel appliances, granite countertops, and a generous breakfast bar overlooking the living and dining areas. Two bedrooms, two full baths, and an upper-level loft complement the distinctive layout. Central air, garage parking, and additional storage add everyday convenience. This professionally managed elevator building offers a fitness room and landscaped courtyard with shared grills. Ideally located near the Jamaica Plain–Mission Hill border, with convenient access to the Heath Street Green Line, Longwood Medical Area, Brookline Village, shops, and restaurants. Nearby Jefferson Playground, Nira Rock Urban Wild, Olmsted Park, and Jamaica Pond offer inviting spaces for outdoor recreation.

251 Heath St Unit 511, Boston

Listing courtesy of Listing Agent: Loftus & Glynn Team from Listing Office: William Raveis R.E. & Home Services.
51 Saint Rose St. Unit 1, Boston
$749,000
2 Beds ⋅ 2 Baths ⋅ 73596288 MLS
A stylish, light-filled JP condo with bonus space to work and unwind! Completely renovated in 2018 and thoughtfully improved since, this well cared for 2 bedroom, 2 bath home greets you with a custom, craftsman-built entryway. The sleek kitchen features white cabinetry, quartzite waterfall counters and Jenn-Air appliances, with island seating that opens to the dining and living areas. Wood floors, central air and in-unit laundry round out the main level. A separately accessed, 440 square foot deeded lower-level bonus area has been finished as a den and office with additional dedicated storage, adding valuable flexibility beyond the main living space. A private covered rear porch and 1 deeded off-street parking space complete the offering. Near the Arnold Arboretum, neighborhood shops and restaurants, and Forest Hills Orange Line access.

51 Saint Rose St. Unit 1, Boston

Listing courtesy of Listing Agent: Ryan Drowne from Listing Office: Coldwell Banker Realty - Boston.
79 Sheridan St Unit 1, Boston
$1,200,000
2 Beds ⋅ 3 Baths ⋅ 73596026 MLS
Ideally situated in the heart of Jamaica Plain’s coveted Hyde Square neighborhood, this luxurious, thoughtfully designed 2-bedroom, 2.5-bath duplex offers 1,498 sq. ft. of beautifully appointed living space with the scale and comfort of a single-family home. Perfect for entertaining, the spectacular open-concept main level seamlessly connects the living room, dining room, and chef-inspired kitchen, all enhanced by elegant high ceilings and oversized windows that flood the home with natural light. An expansive kitchen island serves as the centerpiece for gathering, complemented by a generous pantry offering exceptional storage. The living spaces flow effortlessly onto a private deck and outdoor stone patio, creating an ideal setting for al fresco dining, summer gatherings, or simply relaxing outdoors. Thoughtfully designed for both entertaining and everyday living, the home features two generously sized bedrooms, including an expansive primary suite with an oversized closet and en-suite bathroom with double vanity. Completely gut-renovated to the studs, this exceptional residence features new siding, windows, plumbing, electrical, HVAC, and spray foam insulation, combining sophisticated design with modern efficiency and lasting peace of mind. A 12-month builder's warranty provides additional confidence in the quality of the renovation. One deeded off-street parking space is included, with a second available for purchase. Pet-friendly and ideally located moments from Jamaica Pond, Centre Street’s vibrant restaurants and shops, Whole Foods, the Orange Line and so much more, this home delivers an exceptional combination of luxury, lifestyle, and convenience in one of Jamaica Plain’s most desirable and convenient neighborhoods.

79 Sheridan St Unit 1, Boston

Listing courtesy of Listing Agent: Mission Realty Advisors from Listing Office: Compass.
195 South St Unit 5, Boston
$485,000
2 Beds ⋅ 1 Baths ⋅ 73595985 MLS
Sunny spacious two bed one bath with open kitchen living room, high ceilings, tons of windows, great kitchen with lots of counter space, good closet space, shared balcony, laundry and large private storage in the basement, one deeded off street parking spot. Fantastic location close to shops restaurants and the Forest Hills T stop.

195 South St Unit 5, Boston

Listing courtesy of Listing Agent: Kristen Day from Listing Office: RE/MAX Realty Plus.
22 Goldsmith St., Boston
$749,900
3 Beds ⋅ 1 Baths ⋅ 73595629 MLS
Renovated attached single-family home 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.

22 Goldsmith St., Boston

Listing courtesy of Listing Agent: Patricia Reilly from Listing Office: RE/MAX Real Estate Center.
16 Meehan Unit 2A, Boston
$899,900
3 Beds ⋅ 2 Baths ⋅ 73595523 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!

16 Meehan Unit 2A, Boston

Listing courtesy of Listing Agent: Christopher Buono from Listing Office: All Things Real Estate, Inc..
11 Sedgwick Street Unit 9, Boston
$729,000
2 Beds ⋅ 1 Baths ⋅ 73595516 MLS ⋅ ['9 & 11 Sedgwick Street Condominium'] BLDG.
Bright, beautifully updated, and wonderfully versatile, this second-floor condominium offers comfortable living in the desirable Sumner Hill neighborhood on a one-way residential street just off Centre Street in Jamaica Plain. Sun-filled rooms, hardwood floors, and charming architectural details create a warm and inviting atmosphere. The two-bedroom layout includes a separate living room, while the second bedroom—currently styled as a lounge—offers flexibility for a home office or guest room. The kitchen and stylish tiled bathroom, both renovated in 2023, complement thoughtful modern conveniences, including in-unit laundry, three mini-splits providing heating and cooling, and gas radiator heat. Enjoy your own rear deck, additional basement storage, and the exceptional convenience of a deeded, exclusive-use detached garage with an electric vehicle charger. Across from the library and Curtis Hall community center, with neighborhood coffee shops, restaurants, and recreation courts nearby, this home puts the best of JP within easy reach—including Jamaica Pond, the Arnold Arboretum, and public transportation.

11 Sedgwick Street Unit 9, Boston

Listing courtesy of Listing Agent: Focus Team from Listing Office: Focus Real Estate.
244 Jamaicaway, Boston
$899,900
4 Beds ⋅ 2 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.
One Gartland Street Unit 4C, Boston
$1,450,000
3 Beds ⋅ 3 Baths ⋅ 73595103 MLS ⋅ ["At Doyle's"] BLDG.
Where history meets modern design. One Gartland introduces sixteen thoughtfully crafted condominium residences that honor the legacy of Doyle’s while ushering in a new chapter for Jamaica Plain’s Stonybrook neighborhood. Light-filled interiors, floor-to-ceiling windows, and private balconies create a seamless connection between home and city life. Each residence features open kitchen, living, and dining spaces designed for both everyday living and entertaining, with room for full dining tables, generous seating, and expansive kitchen islands. Custom hardwood cabinetry, paneled appliances, and Taj Mahal quartz counters deliver timeless craftsmanship and understated luxury. Oak floors, solid-core doors, spa-inspired baths, and superior soundproofing complete each home. Residents enjoy elevator access from the garage plus ground-floor retail and a rooftop bar and terrace overlooking the neighborhood. Moments from Franklin Park, the Southwest Corridor, and JP favs like Third Cliff Bakery.

One Gartland Street Unit 4C, Boston

Listing courtesy of Listing Agent: Adams & Co. Team from Listing Office: Real Broker MA, LLC.
60 Carolina Avenue Unit 3, Boston
$1,275,000
3 Beds ⋅ 2 Baths ⋅ 73594282 MLS
60 Carolina Avenue, Unit 3, is the perfect blend of historic character and modern space in an exceptional Jamaica Plain location. The entire home is flooded with natural light, highlighting the rich walnut hardwoods and an open floor plan that feels both airy and sophisticated. The kitchen is a chef’s dream, anchored by a quartz center island and outfitted with sleek European cabinetry, a wine cooler, and high-end Fisher & Paykel gas appliances. The primary suite serves as a true retreat, featuring a walk-through dressing room and a spa-like bathroom with a double vanity, full glass shower, and the comfort of radiant heated floors. Throughout the home, custom closets ensure everything has its place, while floor-to-ceiling windows and a sunny front porch bridge the gap between indoors and out. For those who love to entertain, the sliding glass doors lead to a large, private back deck with stairs leading to a professionally landscaped fenced in yard. Modern conveniences are integrated everywhere, including a built in Sonos ceiling speaker system (living room and primary bed/bath), Nest thermostat, video doorbell, efficient LED lighting, in-unit washer/dryer and central AC. Complete with two-car parking and a private basement storage room, this home balances high-end style with everyday functionality. Enjoy all that JP has to offer including restaurants, bookstores, local shops, cafés, parks and a well connected public transportation system.

60 Carolina Avenue Unit 3, Boston

Listing courtesy of Listing Agent: Maureen Johnson from Listing Office: Coldwell Banker Realty - Weston.
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