Jamaica Plain Homes for Sale: Your Guide to Boston's Urban Oasis with Marc Fiore

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Explore an exquisite selection of homes for sale in Jamaica Plain, Boston, MA, a vibrant neighborhood renowned for its unique blend of urban amenities and natural beauty. From historic Victorians overlooking Jamaica Pond to contemporary condos near Centre Street, this area offers diverse housing options. Discover the perfect property amidst tree-lined streets, independent boutiques, and thriving cultural scenes. Marc Fiore provides unparalleled insight into the Jamaica Plain real estate market, helping you navigate listings from Moss Hill to Hyde Square, ensuring a seamless journey to finding your dream home in this highly sought-after Boston locale.

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Overview of Jamaica Plain Homes for Sale

Searching for homes for sale in Jamaica Plain means entering a market rich with history, community, and diverse architectural styles. This distinctive Boston neighborhood, often simply called "JP," offers a residential experience unlike any other in the city. Prospective buyers will find a wide array of properties, from charming single-family residences to modern condominiums, all nestled within a dynamic urban landscape. The inventory of available homes reflects the area's evolving character, appealing to various tastes and budgets.

Discovering Jamaica Plain's Diverse Housing Market

The Jamaica Plain housing market is characterized by its remarkable variety. When considering homes for sale here, one will encounter everything from meticulously preserved turn-of-the-century houses to sleek new constructions. This diversity extends to price points and property types, making it an accessible yet aspirational community for many. Understanding the nuances of each micro-neighborhood is key to a successful search for your ideal home.

Popular Jamaica Plain Neighborhoods and Their Homes

Within Jamaica Plain, several distinct enclaves offer unique characteristics, influencing the types of homes for sale available. Each area boasts its own charm and appeal, drawing specific demographics and lifestyles.

Moss Hill: Elegance Amidst Nature

Moss Hill is celebrated for its stately homes, often featuring larger lots and mature landscaping. Buyers looking for spacious single-family homes for sale with a more suburban feel, yet still within city limits, frequently gravitate towards this serene, upscale section of Jamaica Plain. The properties here often include impressive architectural details and offer a sense of privacy and tranquility.

Pondside: Classic Charm Near the Emerald Necklace

As its name suggests, Pondside encompasses the areas immediately surrounding Jamaica Pond, a jewel of Frederick Law Olmsted's Emerald Necklace. Homes for sale in Pondside often consist of beautiful Victorians, colonials, and multi-family residences that enjoy close proximity to the pond for recreation. This location is highly desirable for those who value scenic views and easy access to walking, jogging, and boating activities.

Centre Street Corridor: Urban Vibrancy and Accessibility

The Centre Street Corridor serves as Jamaica Plain's commercial and cultural heart. The homes for sale along and near this vibrant thoroughfare typically include condominiums, townhouses, and smaller single-family properties. Residents here enjoy unparalleled access to boutique shops, diverse restaurants, and public transportation, embodying an energetic urban lifestyle.

Hyde Square: A Rich Cultural Tapestry

Hyde Square is known for its strong community feel and vibrant Latinx heritage. The homes for sale in this area often include traditional multi-family houses, offering excellent investment opportunities, alongside charming single-family options. Hyde Square provides a lively atmosphere with unique local businesses and cultural events, making it a dynamic place to live.

Architectural Styles and Property Types in Jamaica Plain

The architectural landscape of Jamaica Plain is as varied as its residents. Those exploring homes for sale will find a captivating blend of historical significance and modern innovation.

Historic Victorians and Brownstones

Many of Jamaica Plain's most iconic properties are its grand Victorian and Queen Anne-style houses, particularly prevalent in areas like Pondside and Moss Hill. These homes for sale often feature intricate woodworking, turrets, and distinctive facades, preserving the neighborhood's rich past. Additionally, classic brownstones contribute to the area's historic appeal.

Modern Condominiums and Lofts

For buyers seeking contemporary living, Jamaica Plain also offers an increasing number of modern condominiums and loft-style units. These homes for sale are often found in renovated historic buildings or new constructions, particularly in the Centre Street and Forest Hills areas, providing amenities desirable for today's urban dwellers.

Multi-Family Dwellings and Investment Opportunities

Jamaica Plain is an attractive location for investors or those seeking income-generating properties, with numerous multi-family homes for sale. Two-family and three-family houses are common, presenting opportunities for owner-occupancy with rental income or pure investment ventures in a consistently desirable market.

The Jamaica Plain Lifestyle and Community

Beyond the structures themselves, acquiring one of the homes for sale in Jamaica Plain means embracing a unique lifestyle characterized by community engagement and access to nature.

Green Spaces and Outdoor Recreation

Central to Jamaica Plain's appeal is its abundance of green spaces. Jamaica Pond, a central feature of the Emerald Necklace, offers extensive recreational opportunities. Arnold Arboretum and Franklin Park also provide vast expanses for walking, biking, and enjoying nature, enhancing the quality of life for residents.

Dining, Arts, and Local Businesses

The neighborhood boasts a thriving scene of independent restaurants, cafes, and boutiques, particularly along Centre Street. Art galleries, live music venues, and community events contribute to a vibrant cultural landscape. This rich tapestry of local businesses and cultural institutions makes living in Jamaica Plain a uniquely engaging experience.

Finding Your Ideal Home in Jamaica Plain with Marc Fiore

Navigating the diverse and competitive market of homes for sale in Jamaica Plain requires local expertise. Marc Fiore is dedicated to providing personalized service, guiding you through every step of the process. From understanding current market trends to identifying properties that perfectly match your criteria, trust Marc Fiore to help you find your dream home in this exceptional Boston neighborhood.

Newest Homes for Sale in Jamaica Plain, Boston, MA

$1,049,000

2 Beds ⋅ 2 Baths ⋅ 73576133 MLS ⋅ NEW Status

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 1,048 SF with 2 bedrooms, 2 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, and recessed lighting. The stunning kitchen showcases contemporary cabinetry, quartz countertops, a large center island, and stainless-steel appliances. The spacious primary suite features a luxurious full bath and custom-built closets. The additional bedroom is spacious and well positioned. Central air, in-unit laundry, a private outdoor deck, and one off-street parking space complete this exceptional offering. Open Houses will be Saturday, 09/12 & Sunday, 09/13 from 1:00 P.M. - 3:00 P.M.

305 Chestnut Ave Unit 3, Boston

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

$715,000

3 Beds ⋅ 1 Baths ⋅ 73575753 MLS ⋅ NEW Status

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.

$650,000

1 Beds ⋅ 1 Baths ⋅ 73575484 MLS ⋅ NEW Status

Welcome to VITA, one of Jamaica Plain’s premier luxury condominium communities! Built in 2019, this sophisticated 1-bedroom plus den residence offers 865 square feet of sleek modern design, upscale building amenities, and unbeatable urban convenience. Perfect for an investor or a patient buyer, this turn-key unit is currently tenant-occupied and rented through July 31, 2027.Step inside Unit 418 to discover a bright, open-concept layout illuminated by oversized windows that flood the space with brilliant natural light. The thoughtful floor plan maximizes every square foot, creating a seamless flow from the living area to a high-end contemporary kitchen. The bonus den provides the ultimate flexible space—ideal for a dedicated home office, a cozy media room, or a creative studio. The kitchen is equipped with premium stainless steel appliances, custom cabinetry, and sleek countertops, serving as both a functional workspace and a beautiful centerpiece for effortless dining and entertaining.As a resident of this highly desirable, professionally managed 82-unit boutique building, you will gain access to an impressive suite of top-tier amenities. Enjoy panoramic neighborhood views and entertain guests from the stunning common roof deck, complete with outdoor grilling stations and fire pits. The building also features a stylish resident lounge, partial concierge services, bicycle storage, and secure garage parking beneath the building. Your day-to-day routine couldn't be easier with exceptional ground-level retail spaces directly on-site, including a Planet Fitness just an elevator ride away.Perfectly situated at 3531 Washington Street, this property offers incredible proximity to the best of Boston. You are just moments from the MBTA Orange Line (Forest Hills and Green Street stations), making your commute into downtown Boston or the Longwood Medical Area a breeze. Enjoy the vibrant local lifestyle with Jamaica Plain’s renowned independent dining, local coffee shops, boutique shopping, and craft breweries right outside your door. For outdoor enthusiasts, the scenic paths of the Southwest Corridor Park, the Arnold Arboretum, and Jamaica Pond are all within easy reach.

3531 Washington Unit 418, Boston

Listing courtesy of Listing Agent: Jessica & Sam Group from Listing Office: JW Real Estate Services, LLC.

$899,000

3 Beds ⋅ 3 Baths ⋅ 73575428 MLS ⋅ NEW Status

Townhouse living in the heart of JP. Expansive and thoughtfully arranged over three levels, this updated home offers the space, privacy and flexibility of a single-family while retaining the ease of condo living. The main living level features an open layout with hardwood floors, gas fireplace, granite and stainless kitchen, convenient powder room, and direct access to a private rear patio — an inviting setup for everyday living and entertaining. The lower level offers tremendous flexibility, with a generous bedroom, newly renovated full bath and excellent separation from the main living areas — ideal for guests, a home office, playroom or media room. Upstairs, the sun-filled primary bedroom offers abundant space and a generous walk-in closet, complemented by a spacious bath with modern double vanity and deep soaking tub. A separate laundry room sits just off the landing, along with access to a private Juliet balcony overlooking the backyard. Central AC and forced-air heat, abundant closet space, private storage shed and deeded driveway parking complete an exceptionally practical home. Enjoy easy access to the 39 bus, Orange Line at Stony Brook and Jackson Square, Longwood Medical Area, Jamaica Pond and the Emerald Necklace — with Whole Foods and neighborhood favorites including Tres Gatos, Brendan Behan, Viva Mi Arepa and City Feed all nearby. A wonderfully livable JP home offering space to spread out, modern comforts and the neighborhood right outside your door. First showings at Open House Saturday - 09-12 from 10:30am - 12noon

75 Forbes St Unit 75, Boston

Listing courtesy of Listing Agent: Andrew Maxfield from Listing Office: In REM Real Estate Inc..

$629,900

2 Beds ⋅ 2 Baths ⋅ 73575012 MLS ⋅ NEW Status

Nestled in one of Jamaica Plain’s most coveted locations, just two blocks from the Arnold Arboretum and vibrant Centre Street, this sun-filled two bedroom and two full bathroom condominium blends modern comfort with timeless charm. An inviting open living space features hardwood floors, a soaring vaulted ceiling with a skylight, and a cozy gas fireplace. The well-appointed kitchen offers granite countertops, stainless steel appliances and cherry cabinetry and an island with seating. The spacious primary suite is a peaceful retreat that is awash in natural light and is complete with a walk-in closet and en-suite bath. A generous second bedroom with ample closet space offers flexibility as a guest room, home office, or creative space. Step outside to a private deck with tranquil treetop views—ideal for morning coffee or entertaining. Additional features include central AC, private basement storage and two off-street parking spaces. This is a pet-friendly association. Ideally located near Jamaica Pond, Centre Street’s shops and restaurants, and the Orange Line. Convenient to both the Faulkner Hospital and the Longwood Medical area. This exceptional condo offers the perfect combination of location, style, and convenience.

35 Ballard St Unit 3, Boston

Listing courtesy of Listing Agent: Bell | Whitman Group from Listing Office: Compass.

$1,690,000

4 Beds ⋅ 3 Baths ⋅ 73574821 MLS ⋅ NEW Status

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.

$1,225,000

3 Beds ⋅ 2 Baths ⋅ 73574666 MLS ⋅ NEW Status

A bright and breezy condo built in 2021, in the heart of Jamaica Plain’s Southwest Corridor: a transit dream, by T or by bike, with two private balconies, a shared roof deck and common lounge, and a backyard dog run. Three bedrooms are all generously sized, including contemporary closets, and a grand living/dining/kitchen space has plenty of room to be all three. Step inside and this one surprises you: custom millwork gives the living room a warmth and character that most newer builds skip entirely, so it lives more like a classic JP home than a new-construction box. Huge windows flood the open layout with light all day long, with sunset views over the Southwest Corridor. The primary suite's walk-in closet alone will win over anyone downsizing from a house. This is a boutique building done right: just 9 residential units, an elevator, and neighbors who genuinely look out for each other—the kind of building with a group text. Systems are all just five years old and recently serviced, newer build means no lead paint, and laundry (washer/dryer included) is right in the unit. One deeded garage parking space (heated!), with easy street and nearby lot parking as backup, plus bike storage in the garage and dedicated basement storage as well. The location is hard to beat: steps to the Green St Orange Line stop and the Southwest Corridor bike path, a quick trip to Jamaica Pond, the Arnold Arboretum, and the Emerald Necklace, and just around the corner from Flaherty Park's dog park and Johnson Playground's splash pad. Centre St's restaurants and shops are minutes away, along with a full calendar of only-in-JP neighborhood events, from Thursdays on the Lawn to the Lantern Parade at the Pond. Ready for you to move right in!

120 Brookside Ave Unit 302, Boston

Listing courtesy of Listing Agent: Kate Ziegler from Listing Office: New Englander Real Estate, LLC.

$485,000

1 Beds ⋅ 1 Baths ⋅ 73574467 MLS ⋅ NEW Status

Welcome to 50 Jamaicaway, Unit 7—a well-maintained and move-in ready one-bedroom condominium offering 620 square feet of comfortable living space in Jamaica Plain. The thoughtfully laid-out floor plan includes a generous entry which includes a spacious coat closet. The generously sized living area will exceed your expectations. The new owner will also enjoy high ceilings and ample storage throughout the unit. The updated kitchen features a new range and refrigerator along with enough space for a small counter height dining table. Fresh interior paint and recently refinished hardwood floors give the home a clean, move-in-ready feel. Additional storage is available in the deeded enclosed basement storage unit. Conveniently located near multiple public transportation options, this inviting condo is an excellent opportunity for a first-time buyer, down-sizer, or investor. ***Photos are virtually staged.

50 Jamaicaway Unit 7, Boston

Listing courtesy of Listing Agent: Mark Ott from Listing Office: Coldwell Banker Realty - Newton.

$699,000

3 Beds ⋅ 1 Baths ⋅ 73574390 MLS ⋅ NEW Status

Bright and sunny 3rd-floor condo perched on a hill among prestigious Arborway homes, offering stunning views of the Arnold Arboretum. Watch the seasons change from your front deck or through the living room windows. An open floor plan and living/dining room wrapped in windows fill the home with abundant natural light from every direction, creating a wonderful space for entertaining. Beautiful period details include high ceilings, built-in china hutch, and wood floors, all meticulously maintained. The spacious, modern eat-in kitchen features a pantry and direct access to a private rear deck overlooking a lush common yard—perfect for al fresco dining and relaxing. An updated bathroom separates two generously sized bedrooms, while a versatile third bedroom with its own private deck is currently used as a home office. Additional features include a newer roof, freshly painted interior, in-unit laundry, and private basement storage. Ideally located just steps from the gates of the Arnold Arboretum, JP Center shops and restaurants, Jamaica Pond, and a 10-minute walk to Forest Hills MBTA Station, offering easy access to downtown Boston. Ample on-street parking for you and your guests. Great association with a hefty reserve.

250 Arborway Unit 3, Boston

Listing courtesy of Listing Agent: Love Live Team from Listing Office: Insight Realty Group, Inc.

$5,200,000

16 Beds ⋅ 11 Baths ⋅ 73574354 MLS ⋅ NEW Status

A premier mixed-use investment opportunity at the corner of Centre Street and Sheridan Street in the heart of Jamaica Plain’s Hyde Square, 374 Centre Street offers 9,153 square feet of rentable area, strong income, and compelling long-term upside in one of Boston’s established rental markets. The fully renovated property consists of two street-level commercial spaces, one office, and four expansive 4-bedroom, 2-bath residential apartments. All residential units have been gut renovated and are fully leased through September 1, 2027, while all three commercial spaces are currently leased. Total gross monthly rental income is $33,000, supporting an attractive 6.6% cap rate and providing immediate cash flow with additional opportunity for future income growth. The prominent corner location offers excellent visibility and exposure for commercial tenants while placing residents in the heart of Hyde Square. The property offers convenient access to the Longwood Medical Area and the numerous universities, hospitals, and institutions throughout the surrounding area. Multiple public transportation options connect the property to destinations across Boston, including the Route 39 bus along Centre Street, the Orange Line at Jackson Square, and Green Line service near Heath St. Jamaica Pond, Whole Foods Market, the Arnold Arboretum, and Franklin Park are all nearby, while Centre Street’s restaurants, shops, and neighborhood amenities create an exceptionally walkable setting for residents and businesses alike. 374 Centre Street may be acquired independently or together with neighboring 370 Centre Street, a separately offered mixed-use property consisting of two commercial spaces and four fully renovated residential apartments. Combined, the properties comprise five commercial spaces and eight residential apartments, creating a rare opportunity to acquire significant scale in a single location along one of Jamaica Plain’s most prominent commercial corridors. With strong existing income, renovated residential units, a high-visibility corner location, future upside, and the flexibility to acquire individually or as a package, 374 Centre Street offers a compelling combination of cash flow, scale, and long-term value. Pro forma and additional information available upon request.

374-374A Centre St, Boston

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

$795,000

2 Beds ⋅ 1 Baths ⋅ 73574197 MLS ⋅ NEW Status ⋅ ['Pondside Condominium'] BLDG.

Near Jamaica Pond, an elegant brownstone two-bedroom plus den replete with period details, including a woodburning fireplace. This expansive condo offers versatile spaces and updates that honor its historic character. Boasting oversize windows that let in south-facing light and tree views, the dining and living rooms adjoin by pocket doors. The generous living room features bowed windows, a quarter-sawn oak mantel, and picture rails. The bright adjacent kitchen offers dining space, ample counters, cabinet and drawer storage, and laundry in the pantry. The den with custom built-in bookcases can serve as an alternate bedroom. Crossing the foyer, enter a hall with two bedrooms separated by a refinished bathroom that features subway tiling, refined shower fixtures, and a transom window. In this thoughtfully managed association, the condo fee includes heat, hot water and maintenance. Enjoy a graceful shared courtyard and private ground-level storage. Blocks to the pond, Centre Street shops and restaurants, Green Street T, 39 Bus, and bike paths to Longwood Medical and Back Bay.

17 Lakeville Road Unit 4, Boston

Listing courtesy of Listing Agent: Good Boston Living Team from Listing Office: Gibson Sotheby's International Realty.

$5,000,000

16 Beds ⋅ 9 Baths ⋅ 73574148 MLS ⋅ NEW Status

A premier mixed-use investment opportunity in the heart of Jamaica Plain’s Hyde Square, 370 Centre Street offers 9,768 square feet of rentable area, strong in-place income, and compelling long-term upside in one of Boston’s most established rental markets. The fully renovated property consists of two street-level commercial spaces and four expansive 4-bedroom, 2-bath residential apartments. All residential units have been gut renovated to modern standards and are fully leased through September 1, 2027. Total gross monthly rental income is $31,300, supporting an attractive 6.5% cap rate and providing immediate cash flow with additional opportunity for future income growth. The location is a key driver of long-term demand. Positioned directly on Centre Street in vibrant Hyde Square, the property offers convenient access to the Longwood Medical Area and the numerous universities, hospitals, and institutions throughout the surrounding area. Multiple public transportation options connect the property to employment and education centers across Boston, including the Route 39 bus along Centre Street, the Orange Line at Jackson Square, and Green Line service near Longwood. Jamaica Pond, Whole Foods Market, the Arnold Arboretum, and Franklin Park are all nearby, while Centre Street’s restaurants, shops, and neighborhood amenities create an exceptionally walkable setting for residents and businesses alike. 370 Centre Street may be acquired independently or together with neighboring 374 Centre Street, a separate seven-unit mixed-use property. Combined, the properties comprise five commercial spaces and eight fully renovated residential apartments, creating a rare opportunity to acquire meaningful scale in a single location along one of Jamaica Plain’s most prominent commercial corridors. With strong existing income, renovated residential units, future upside, exceptional connectivity, and the flexibility to acquire individually or as a package, 370 Centre Street offers a compelling combination of cash flow, scale, and long-term value. Pro forma and additional information available upon request.

370-372 Centre St, Boston

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

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