Jamaica Plain Homes under $2 million

Welcome to Jamaica Plain, a vibrant and eclectic neighborhood nestled in the heart of Boston, Massachusetts. Known for its rich history, diverse community, and lush green spaces, Jamaica Plain offers a unique blend of urban convenience and suburban charm. With its tree-lined streets and historic brownstones, this area is perfect for those seeking a lively atmosphere paired with a strong sense of community.

Jamaica Plain is renowned for its cultural diversity, making it a melting pot of traditions, cuisines, and lifestyles. Residents enjoy an array of local restaurants, cafes, and shops, while the nearby Arnold Arboretum and Jamaica Pond provide ample opportunities for outdoor activities, from leisurely strolls to picnics and kayaking. The neighborhood also boasts a robust arts scene, with galleries and events that celebrate local talent and creativity.

For those considering a home in this dynamic area, Jamaica Plain offers a range of properties under $2 million, making it an attractive option for families, young professionals, and investors alike. From charming Victorian homes to modern condos, there is something to suit every taste and lifestyle. With easy access to public transportation, residents can enjoy a quick commute to downtown Boston, while still relishing the peaceful ambiance of their neighborhood.

Whether you're looking to immerse yourself in the local culture or simply enjoy the beautiful surroundings, Jamaica Plain is a fantastic place to call home. Explore the possibilities of living in this vibrant community and discover your dream home today!

Newest Jamaica Plain Homes under $2 million

$1,395,000

3 Beds ⋅ 2 Baths ⋅ 73600183 MLS

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 4D, Boston

Listing courtesy of Listing Agent: Adams & Co. Team from Listing Office: Real Broker MA, LLC.

$699,900

2 Beds ⋅ 3 Baths ⋅ 73599577 MLS ⋅ ['Wise Chestnut Condominium'] BLDG.

There is a lot to like about this Jamaica Plain home, starting with the extensive renovations and thoughtful improvements made over the past few years. Renovated in 2023, the property has since been further upgraded with a beautifully finished primary bathroom, walk-in closet, and laundry room. Many of the original builder-grade finishes have also been replaced with more attractive, higher-quality selections. Hardwood floors throughout the upper level add warmth and character, while the generously sized kitchen offers plenty of room for everyday living and entertaining. The location is another real advantage, with Jackson Square T station, the Southwest Corridor, and a great selection of neighborhood restaurants and shops all within easy walking distance. And for anyone familiar with the challenges of parking in Boston, the two tandem spaces in a gated driveway are a particularly welcome feature. Comfortable, well-maintained, and genuinely move-in ready, this is a home where much of the hard work has already been done.

5 Wise St Unit 1, Boston

Listing courtesy of Listing Agent: Harry Silverstein from Listing Office: Keller Williams Realty Boston Northwest.

$885,000

3 Beds ⋅ 2 Baths ⋅ 73599294 MLS ⋅ ['Two Boylston Condominium'] BLDG.

Rare opportunity to own a gorgeous 3 bed/2 bath condo with elevator, 1 garage parking, and private storage! Sun-filled south facing open floor plan with direct access to private front balcony and spacious back deck. Thoughtfully designed modern kitchen with bar seating, vented out microwave, induction stove, and soapstone counter tops. Lovely primary bedroom with walk in closet and ensuite bath with glass enclosed shower. 2 additional good sized bedrooms and a full bathroom with tiled tub shower. Enjoy coffee on the front balcony and hosting in the large back deck. Complete with central air, in unit laundry, ample custom closet space, garage parking and private storage. Professionally managed building with elevator and butterfly intercom system. Conveniently located near Centre St, Jamaica Pond, Stonybrook T station, Whole Foods, local shops and restaurants, and Arnold Arboretum. Easy access to Longwood Medical and Downtown Boston.

2 Boylston St Unit 4, Boston

Listing courtesy of Listing Agent: Victoria Tran Slomiak from Listing Office: Lineage Realty Group.

$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.

$849,000

3 Beds ⋅ 2 Baths ⋅ 73598658 MLS

At the corner of Chestnut Avenue and Spring Park Avenue, this three-level townhome is a commuter's dream with a dedicated parking space and the Orange Line two blocks away. Wood floors run through the main level, where the living room flows into the dining area and double sliders open onto a private deck for grilling, open-air meals, or a slow hour with a book. Wind your way up the sundrenched stairwell tower to the primary suite that feels like its own retreat with a walk-in closet and ensuite full bath. The spaces has plenty of room for a King bed and is rounded out by a Juliet balcony letting in fresh air and natural light. Two additional bedrooms and a second full bath give flexibility for guests, a home office, or creative work, while a second deck extends the outdoor living space. Full-size laundry in the unit and central air offer modern conveniences that can be hard to find in JP but the real draw here is the location. Stony Brook station, the Southwest Corridor, and the restaurants and shops of Centre Street are all nearby, making this the perfect spot for work or play!

196 Chestnut Ave Unit J, Boston

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

$750,000

2 Beds ⋅ 1 Baths ⋅ 73598643 MLS

On a tree-filled hilltop near Arnold Arboretum, this condo with two bedrooms plus den includes parking, garden space, and so much storage. As you enter, a bright, roomy foyer with two closets welcomes you. In classic form, the living room with a bank of south-facing windows leads into a formal dining room adorned with wainscotting and three windows facing sunset. From there, the remarkably spacious kitchen includes a pass-through pantry with two counters and glass-front cabinetry. The kitchen’s induction stove, extensive granite counters and cherry cabinetry, including floor-to-ceiling and drawer storage, will accommodate all the cooking projects you can whip up. From the kitchen, head out via the exclusive deck to pick herbs from your raised garden bed. Also from the kitchen, float downstairs to a 120 sq ft room with exposed vintage wood ceilings that can serve as a den, office/studio or guest space. This level also hosts a 200 sq ft exclusive storage room where you can stash everything you need out of sight. Back on the main level, the hallway to the bedrooms and bathroom includes both laundry and linen closets for everyday ease. The primary bedroom offers two closets, including a walk-in. In addition to the high-efficiency heat pump for forced-air cooling and heating, a boiler with Nest thermostats provides back-up comfort. Enjoy recessed lighting throughout. This unit’s parking space includes an EV charger. In Jamaica Plain’s Arborway area, find daily serenity in the arboretum. Blocks to Centre/South Street shops, with Happy Market, Jadu cafe, Vee Vee restaurant, Monumental Market, Papercuts Bookshop, and the public lawn at Loring Greenough House. Just half a mile to Forest Hills T.

107 Saint Rose Street Unit 1, Boston

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

$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.

$615,000

3 Beds ⋅ 1 Baths ⋅ 73598211 MLS ⋅ ['120 Day Street Condominium'] BLDG.

Ideally located in the heart of Jamaica Plain’s vibrant Centre Street, this well-appointed 3 bedroom condo offers the perfect blend of comfort, convenience, and flexibility. The thoughtful floor plan includes a versatile third bedroom that can easily serve as a home office, guest room, or bonus space. The updated kitchen features ample cabinet space and a built-in corner bench, creating the perfect spot for a cozy dining nook. Step outside to your *Brand New* private rear deck, ideal for morning coffee, outdoor dining, or relaxing at the end of the day. Enjoy easy access to the shops, restaurants, and cafes of Centre Street, along with nearby Orange and Green Line transit options for a seamless commute. A fantastic opportunity to enjoy all that Jamaica Plain has to offer.

120 Day St Unit 2, Boston

Listing courtesy of Listing Agent: ME Collective Group from Listing Office: Compass.

$485,972

2 Beds ⋅ 1 Baths ⋅ 73598135 MLS ⋅ ['Creighton Commons Condominium'] BLDG.

Mayor's Office Of Housing Income Restricted Resale Condo In Jamaica Plain. This affordable unit features stainless steel appliances, in-unit laundry, energy efficient heating system, garage parking (# 13), and has an abundance of natural light thanks to its southern orientation. Its location is within short distance from amenities such as Whole Foods Market, restaurants and cafes of Centre Street, and the Jamaica Pond. Bus Routes: 35, 36, 39, 41. T Station: Jackson Square (Orange Line), Heath Street (Green Line-E). To qualify the buyer's annual household income must be less than or equal to 80% of Area Median Income - $96,000 for 1, $109,700 for 2, and $123,400 for a 3 person household. Interested buyers must meet the AMI requirements and other criteria of eligibility. Buyers must be approved by the Mayor's Office of Housing.

21 Creighton St Unit 13, Boston

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

$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.

$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.

$919,000

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.

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Jamaica Plain Homes under $2 million

Newest Jamaica Plain Homes under $2 million

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