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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 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!

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 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

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.

73598910 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.

$9,450,000

NEWER CONSTRUCTION MIXED-USE BUILDING FOR SALE IN JAMAICA PLAIN - Fully stabilized mixed-use building for sale featuring 23 residential apartments and 1 retailunit. High end condo finishes including modern cabinets & vanities, stone countertops, all new stainless steel appliances & fixtures, in-unit washer/dryers, and ample natural light. The apartments include five studios, eleven 1-bedroom units, three 2-bedroom units, and four artist live/work lofts. There are 6 off-street parking spots on the premises leased privately to tenants. The building also includes a bike room, package room, gym amenity, elevator, and loading area for moving. Please reach out to the listing broker for the current pro-forma, floor plans, and to schedule a tour.

73598802 MLS

NEWER CONSTRUCTION MIXED-USE BUILDING FOR SALE IN JAMAICA PLAIN - Fully stabilized mixed-use building for sale featuring 23 residential apartments and 1 retailunit. High end condo finishes including modern cabinets & vanities, stone countertops, all new stainless steel appliances & fixtures, in-unit washer/dryers, and ample natural light. The apartments include five studios, eleven 1-bedroom units, three 2-bedroom units, and four artist live/work lofts. There are 6 off-street parking spots on the premises leased privately to tenants. The building also includes a bike room, package room, gym amenity, elevator, and loading area for moving. Please reach out to the listing broker for the current pro-forma, floor plans, and to schedule a tour.

197 Green, Boston

Listing courtesy of Listing Agent: Sean Rose from Listing Office: City Realty Group.

$9,450,000

NEWER CONSTRUCTION MIXED-USE BUILDING FOR SALE IN JAMAICA PLAIN - Fully stabilized mixed-use building for sale featuring 23 residential apartments and 1 retailunit. High end condo finishes including modern cabinets & vanities, stone countertops, all new stainless steel appliances & fixtures, in-unit washer/dryers, and ample natural light. The apartments include five studios, eleven 1-bedroom units, three 2-bedroom units, and four artist live/work lofts. There are 6 off-street parking spots on the premises leased privately to tenants. The building also includes a bike room, package room, gym amenity, elevator, and loading area for moving. Please reach out to the listing broker for the current pro-forma, floor plans, and to schedule a tour.

41 Beds ⋅ 24 Baths ⋅ 73598795 MLS

NEWER CONSTRUCTION MIXED-USE BUILDING FOR SALE IN JAMAICA PLAIN - Fully stabilized mixed-use building for sale featuring 23 residential apartments and 1 retailunit. High end condo finishes including modern cabinets & vanities, stone countertops, all new stainless steel appliances & fixtures, in-unit washer/dryers, and ample natural light. The apartments include five studios, eleven 1-bedroom units, three 2-bedroom units, and four artist live/work lofts. There are 6 off-street parking spots on the premises leased privately to tenants. The building also includes a bike room, package room, gym amenity, elevator, and loading area for moving. Please reach out to the listing broker for the current pro-forma, floor plans, and to schedule a tour.

197 Green, Boston

Listing courtesy of Listing Agent: Sean Rose from Listing Office: City Realty Group.

$849,000

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!

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

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.

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

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.

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

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.

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

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.

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.

$359,000

A cozy pied-a-terre surrounded by plenty of quaint Jamaica Plain just outside the door. Ideally situated between Centre St (only a stone’s throw away) and the Jamaica Pond, its location is one of JP’s best. You can see Café Siete and The Joint right across the street from your front door. Beyond Proof (formerly 10 Tables) is just around the corner. Whether you desire a delicious coffee and pastry or a full breakfast, lunch, or dinner, these top JP destinations are yours to enjoy. You’ll also see the Jamaica Pond at the other end of the street; one of the more popular parks in the area and designed by famed Frederick Law Olmstead.The unique and flexible apartment incorporates a large gumwood trimmed room to be used as you please. It works as living area, art gallery, or bedroom. Through the freshly painted classic kitchen is another space for sleeping, art studio, or den. An excellent value for your cozy home in Jamaica Plain.

1 Beds ⋅ 1 Baths ⋅ 73597535 MLS

A cozy pied-a-terre surrounded by plenty of quaint Jamaica Plain just outside the door. Ideally situated between Centre St (only a stone’s throw away) and the Jamaica Pond, its location is one of JP’s best. You can see Café Siete and The Joint right across the street from your front door. Beyond Proof (formerly 10 Tables) is just around the corner. Whether you desire a delicious coffee and pastry or a full breakfast, lunch, or dinner, these top JP destinations are yours to enjoy. You’ll also see the Jamaica Pond at the other end of the street; one of the more popular parks in the area and designed by famed Frederick Law Olmstead.The unique and flexible apartment incorporates a large gumwood trimmed room to be used as you please. It works as living area, art gallery, or bedroom. Through the freshly painted classic kitchen is another space for sleeping, art studio, or den. An excellent value for your cozy home in Jamaica Plain.

14 Pond St Unit 2, Boston

Listing courtesy of Listing Agent: John Maxfield from Listing Office: Maxfield & Company Real Estate.

$899,999

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.

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

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.

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.

$948,000

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.

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.

$749,000

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.

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.

$1,200,000

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.

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.

$550,000

65 Brookside Unit 6. More photos coming November 4 or 5. Offers a rare opportunity to own a below-market rate live/work artist studio in Jamiaca Plain. Renovated kitchen, updated electrical, plumbing, windows, new roof, and up to date heating and AC will allow you to move right in and start the next chapter of your creative life. One deeded parking space is included. 65 Brookside Ave U:6 is a 1,182-square-foot three floor townhouse located in a Jamaica Plain artist neighborhood. Originally constructed in 1899, this property remains in great condition, blending historic charm with the benefits of a thoughtfully maintained residence. Enter on the first floor of this three story home to see this unique opportunity to own a live/work space at an "affordable" price. Your neighbors will be some of the most creative working artists in all genres. The layout includes two bedrooms, a kitchen dining area and a seperarate work/live space on the first floor. There is one full bathroom and one half bathroom, ensuring both privacy and functionality for residents and guests alike. Beyond the interior, the residence features a private deeded patio/parking space. Located seconds from the orange line and the tree lined southwest corridor park and bike path--so you can travel all over the city and beyond with ease. The nearby historic Haffenreffer Brewery complex has been repurposed with offices, gym, cafes, restaurants, Sam Adams tap house, and a pottery studio. Around the corner is a children's playground, Minton Street community garden and nearby dog park. Franklin park is another great option for your daily routine. Artist certification is required.Your agent or the selling agent can help guide you through that process. Income and asset restrictions are in place in order to keep this home affordable

2 Beds ⋅ 2 Baths ⋅ 73595996 MLS

65 Brookside Unit 6. More photos coming November 4 or 5. Offers a rare opportunity to own a below-market rate live/work artist studio in Jamiaca Plain. Renovated kitchen, updated electrical, plumbing, windows, new roof, and up to date heating and AC will allow you to move right in and start the next chapter of your creative life. One deeded parking space is included. 65 Brookside Ave U:6 is a 1,182-square-foot three floor townhouse located in a Jamaica Plain artist neighborhood. Originally constructed in 1899, this property remains in great condition, blending historic charm with the benefits of a thoughtfully maintained residence. Enter on the first floor of this three story home to see this unique opportunity to own a live/work space at an "affordable" price. Your neighbors will be some of the most creative working artists in all genres. The layout includes two bedrooms, a kitchen dining area and a seperarate work/live space on the first floor. There is one full bathroom and one half bathroom, ensuring both privacy and functionality for residents and guests alike. Beyond the interior, the residence features a private deeded patio/parking space. Located seconds from the orange line and the tree lined southwest corridor park and bike path--so you can travel all over the city and beyond with ease. The nearby historic Haffenreffer Brewery complex has been repurposed with offices, gym, cafes, restaurants, Sam Adams tap house, and a pottery studio. Around the corner is a children's playground, Minton Street community garden and nearby dog park. Franklin park is another great option for your daily routine. Artist certification is required.Your agent or the selling agent can help guide you through that process. Income and asset restrictions are in place in order to keep this home affordable

65 Brookside Ave Unit 6, Boston

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

$485,000

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.

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.

$749,900

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.

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.

$899,900

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!

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..

$729,000

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.

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.

$899,900

**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!

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.

$1,275,000

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.

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.

$829,000

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.

3 Beds ⋅ 2 Baths ⋅ 73594066 MLS

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

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.

2 Beds ⋅ 1 Baths ⋅ 73593633 MLS

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

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.

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.

$565,000

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.

2 Beds ⋅ 1 Baths ⋅ 73593589 MLS

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

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.

3 Beds ⋅ 1 Baths ⋅ 73593331 MLS

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

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!

2 Beds ⋅ 2 Baths ⋅ 73593291 MLS ⋅ ['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

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.

5 Beds ⋅ 3 Baths ⋅ 73593293 MLS

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.

$1,100,000

Ideally situated in the heart of Jamaica Plain’s coveted Hyde Square neighborhood, overlooking the leafy canopy of Sheridan Street, this luxurious 2 bed, 2.5 bath duplex offers 1,409 square feet 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 tray 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 walk-in pantry offering exceptional storage. The living spaces flow effortlessly onto an oversized private deck, creating an ideal setting for al fresco dining, summer gatherings, or simply relaxing outdoors. Intentionally designed for both entertaining and everyday living, the home features two bedrooms privately situated on the upper level, providing a peaceful separation from the main living areas. The primary suite enjoys captivating city views, offering a beautiful retreat above the neighborhood. 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, and the Orange Line, this home delivers an exceptional combination of luxury, lifestyle, and convenience in one of Jamaica Plain’s most desirable neighborhoods.

2 Beds ⋅ 3 Baths ⋅ 73593197 MLS

Ideally situated in the heart of Jamaica Plain’s coveted Hyde Square neighborhood, overlooking the leafy canopy of Sheridan Street, this luxurious 2 bed, 2.5 bath duplex offers 1,409 square feet 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 tray 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 walk-in pantry offering exceptional storage. The living spaces flow effortlessly onto an oversized private deck, creating an ideal setting for al fresco dining, summer gatherings, or simply relaxing outdoors. Intentionally designed for both entertaining and everyday living, the home features two bedrooms privately situated on the upper level, providing a peaceful separation from the main living areas. The primary suite enjoys captivating city views, offering a beautiful retreat above the neighborhood. 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, and the Orange Line, this home delivers an exceptional combination of luxury, lifestyle, and convenience in one of Jamaica Plain’s most desirable neighborhoods.

79 Sheridan St Unit 2, Boston

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

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