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

Advanced Search Market Reports Home Value Connect

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.

< Search all Homes for Sale in Boston, MA

Search Jamaica Plain by Lifestyle

Search Jamaica Plain by Price

Search Jamaica Plain by Bedrooms

Search Jamaica Plain by Bathrooms

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

$899,900

3 Beds ⋅ 2 Baths ⋅ 73595523 MLS ⋅ NEW Status

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..

$729,000

2 Beds ⋅ 1 Baths ⋅ 73595516 MLS ⋅ NEW Status ⋅ ['9 & 11 Sedgwick Street Condominium'] BLDG.

Bright, beautifully updated, and wonderfully versatile, this second-floor condominium offers comfortable living in a fantastic Jamaica Plain location on the edge of the desirable Sumner Hill neighborhood. Sun-filled rooms, hardwood floors, and charming architectural details create a warm and inviting atmosphere. The flexible floor plan offers the option of one or two bedrooms, allowing space for a home office, guest room, or separate den. The renovated kitchen and stylish tiled bathroom complement thoughtful modern conveniences, including in-unit laundry, mini-split air conditioning, and gas-fired hot water heat. Enjoy your own private rear deck, additional basement storage, and the exceptional convenience of garage parking with an electric vehicle charger. Just moments from Jamaica Pond, the Arnold Arboretum, neighborhood coffee shops, restaurants, and public transportation, this home offers a wonderful combination of comfort, convenience, and the vibrant Jamaica Plain lifestyle.

11 Sedgwick Street Unit 9, Boston

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

$899,900

4 Beds ⋅ 2 Baths ⋅ 73595385 MLS ⋅ NEW Status

**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.

$1,450,000

3 Beds ⋅ 3 Baths ⋅ 73595103 MLS ⋅ NEW Status ⋅ ["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.

$1,275,000

3 Beds ⋅ 2 Baths ⋅ 73594282 MLS ⋅ ACTIVE Status

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.

$829,000

3 Beds ⋅ 2 Baths ⋅ 73594066 MLS ⋅ ACTIVE Status

Bright and beautifully renovated, this second-floor condo offers the perfect blend of comfort, style, and convenience. Filled with natural light, the home features a thoughtfully updated interior, a modern kitchen, efficient HVAC, and an inviting open layout that's ideal for both everyday living and entertaining. The spacious primary bedroom includes an en-suite bathroom and two closets, providing both comfort and ample storage. A dedicated laundry room with washer and dryer hookups adds everyday convenience. Step outside to your private back deck, perfect for relaxing with a morning coffee or dining outdoors. Additional private storage in the basement offers even more space for your belongings. Ideally located just minutes from the train, parks, restaurants, and shopping, this home combines neighborhood charm with easy access to everything you need.

29 Rosemary St Unit 2, Boston

Listing courtesy of Listing Agent: Jennifer Epstein from Listing Office: Coldwell Banker Realty - Wellesley.

$749,000

2 Beds ⋅ 1 Baths ⋅ 73593633 MLS ⋅ ACTIVE Status

Embrace loft-style living in the heart of Jamaica Plain in this historic 2 bed condo that was once an early 20th-century storefront. The unique interior offers a welcome break from cookie-cutter urban offerings, blending vintage character with modern updates. Dramatic 10-foot beadboard ceilings, custom built-in bookshelves, and gorgeous original wood flooring greet you inside. The expansive main living space is highlighted by huge, oversized windows that bring in spectacular sunlight, and the open floor plan provides an exceptional setting for entertaining. Beautifully renovated kitchen is complete with quartz countertops, pantry, stainless appliances & peninsula seating. There are two sizeable bedrooms with excellent closets, and a fully renovated bathroom offering modern fixtures and a clean, spa-like aesthetic. Notable features include private back patio, rare off-street parking, 2023 mini split heat + AC, tankless hot water, in-unit laundry, and basement storage. Desirable commuter location just a short walk to Green Street T (orange line) and Southwest Corridor Park and bike path for an easy ride downtown. The vibrancy of Centre Street is only a stone’s throw away, with restaurants, cafes, shops and easy access to the greenery of Jamaica Pond. Combining historical architecture, modern amenities, and an unbeatable central JP location, this property is a rare treat.

45 Green St Unit A, Boston

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

$1,395,000

6 Beds ⋅ 2 Baths ⋅ 73593621 MLS ⋅ ACTIVE Status

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.

$565,000

2 Beds ⋅ 1 Baths ⋅ 73593589 MLS ⋅ ACTIVE Status

Situated in the vibrant Arnold Arboretum and Centre Street neighborhood, this sun-drenched, elevated first-floor condo perfectly combines timeless charm with modern comfort. Natural light pours through classic bay windows, accentuating rich hardwood flooring and a fluid open layout that connects the living and dining areas to the kitchen. Ideal for both daily living and entertaining, the home features generous bedrooms, custom built-in bookshelves, and seamless access to a private back patio overlooking a fenced shared yard. Complete with exceptional proximity to public transit, popular dining, and neighborhood shops, this well-appointed residence offers an ideal blend of convenience and quiet retreat.

85 Jamaica St Unit 1, Boston

Listing courtesy of Listing Agent: Elynn Chen from Listing Office: Redfin Corp..

$680,000

3 Beds ⋅ 1 Baths ⋅ 73593331 MLS ⋅ ACTIVE Status

Welcome to this inviting 3 bedroom condo in the heart of Jamaica Plain, where thoughtful spaces, outdoor living, and an unbeatable location come together. A welcoming foyer sets the tone as you enter, opening into a comfortable living and dining area filled with natural light. Toward the rear of the home, the spacious eat-in kitchen offers plenty of room for everyday living, along with the convenience of in-unit laundry. Step outside to your private deck, a peaceful spot for morning coffee or unwinding at the end of the day. The home offers two well-sized bedrooms plus a versatile bonus room that can easily serve as a third bedroom, home office, or additional living space. Enjoy the rare convenience of a driveway parking space, a beautifully landscaped garden, and additional private storage in the basement. Ideally situated just moments from the Forest Hills and Green Street T stops, Centre St, and the Southwest Corridor, this home makes commuting and exploring the neighborhood effortless.

44 Boynton St Unit B, Boston

Listing courtesy of Listing Agent: Emma Kaloupek from Listing Office: Columbus and Over Group, LLC.

$949,000

2 Beds ⋅ 2 Baths ⋅ 73593291 MLS ⋅ ACTIVE Status ⋅ ['Cabot Estates'] BLDG.

Welcome to luxurious resort-style living at Cabot Estate! Situated on over 23 acres of pristine, lushly landscaped grounds, Unit H402 is a sun-drenched, turnkey condominium offering an exceptional blend of modern elegance, tranquil surroundings, and unmatched location convenience. As you step inside, you are greeted by an inviting open-concept layout defined by soaring high ceilings, skylights, fresh neutral tones, and expansive windows flooding the home with natural light. The sprawling living area serves as the warm heart of the home, centered around a cozy fireplace—ideal for relaxing on cool evenings or entertaining guests. Step through glass sliding doors out onto your large private balcony, an ideal spot for morning coffee, outdoor dining, or simply taking in the serene, tree-lined views.The chef-inspired kitchen features rich cabinetry, quality countertops, stainless steel appliances, and a seamless flow into the dedicated dining space. The bedroom wing is up just a few stairs from the main living area. The generous primary suite acts as a peaceful retreat, featuring ample closet space and a full en-suite bath. The spacious second bedroom is perfect for guests, a den, or a dedicated home office. Additional features include 2026 installed high efficiency heat and ac pump, in-unit laundry, and a spacious garage.Set within a secure 24-hour gated, pet-friendly community, residents enjoy top-tier lifestyle amenities including scenic walking and jogging trails throughout the expansive private grounds, a sparkling outdoor pool, tennis courts, a fitness center, and a historic stone clubhouse.Unbeatably located, this home offers fast, effortless access to the Longwood Medical Area, historic Brookline Village, Jamaica Pond, and Downtown Boston. Whether commuting for work or enjoying local boutique shopping and fine dining, everything you need is just minutes away. Schedule your private showing today and be home in time for the holidays! Furniture and furnishings available for separate purchase; details upon request!

241 Perkins St Unit H-402, Boston

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

$1,495,000

5 Beds ⋅ 3 Baths ⋅ 73593293 MLS ⋅ ACTIVE Status

The marble mantel is still there — arched opening, scrolled keystone, original cast-iron summer cover in place. So are two pierced plaster ceiling medallions, a walnut stair with a carved volute and a rosette newel cap, deep built-up casings under a century intact after more than a century, 4-panel doors on original hardware, and a bay-window parlor that already works. JP's best condo resales are conversions of pre-1910 buildings, not new construction. Plenty of details to preserve here! An 1865 Second Empire three-family on a 9,600 square foot lot in the 3F-5000 subdistrict. Straight-sided slate mansard, segmental dormers with bracketed hoods, deep cornice on paired scroll brackets, 2-story canted bay. A spindled entry porch, a bracketed side porch, and wall-mounted espaliers. Nothing is built on the east side and nothing is likely to be: a community garden runs that line, then Lawndale Terrace, then the Southwest Corridor park, with the Orange Line beyond. 63.61 feet of frontage, just over 150 feet deep, roughly 73 feet of open yard behind the house, a 17.7 foot driveway on the west side, pkg for 4.The lot clears district minimums on area and frontage with room to spare. Setbacks are not a constraint. Keeping the shell and adding to the rear is the path the comps and the approvals both favor. Real work ahead, but the reward here is worth the effort. Site visits by appointment.

6 Oakdale St, Boston

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

Start Your Search

Prev
1
2
3
...
10
of 10
Next

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.