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Homes for Sale in Jamaica Plain, MA

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Locals and people from all over the country – and the world – are lining up to purchase homes for sale in Jamaica Plain, a classic Boston neighborhood. Jamaica Plain’s popularity should come as no surprise; it is vibrant and aesthetically pleasing, while still maintaining a homey, comfortable energy. Being just a short commute from Boston’s bustling city-center, it has something for everyone.

About Boston’s Jamaica Plain Neighborhood

About Homes for Sale in Jamaica Plain, MA

Locals and people from all over the country – and the world – are lining up to purchase homes for sale in Jamaica Plain, a classic Boston neighborhood. Jamaica Plain’s popularity should come as no surprise; it is vibrant and aesthetically pleasing, while still maintaining a homey, comfortable energy. Being just a short commute from Boston’s bustling city-center, it has something for everyone.

Jamaica Plain is in historic Boston, but it has done an excellent job of bridging the gap between eras to become a very modern, cultured neighborhood. Homes for sale in Jamaica Plain continue to perfectly balance the old and new. Victorian-era beauties are around the corner from condominiums and apartment buildings. Real estate continues to flourish as Jamaica Plain continues to be a residential destination for everyone. Jamaica Plain remains a great place for buying a home, setting down roots, and enjoying life to the fullest.

Jamaica Plain’s History and Sprawling Landscape

Historians often debate the origin of Jamaica Plain’s name. There is a possibility that the name comes from the Caribbean Island of Jamaica. The love of rum is definitely a factor here. Jamaica Plain occupants used to call rum, “Jamaica”. However, there is a more likely speculation that Jamaica Plain really got its name from a chief of a Native American tribe that lived there. Jamaica Plain was originally part of the Town of Roxbury in the 1630s before it became an independent neighborhood in 1874. Originally, the main industry was farming. As commerce increased, real estate boomed, causing a rise in construction of homes for sale in Jamaica Plain It evolved into the residential dream it is today.

Many abolitionists settled in Jamaica Plain. In fact, some present-day residents think their homes were a stop on the Underground Railroad. However, that is probably unlikely when you consider where Jamaica Plain is on the route to Canada.

Jamaica Plain was also home to one of America’s first wartime hospitals, which treated Revolutionary War soldiers. Sprinkled throughout Jamaica Plain’s greenery and streets are war memorials. One of them is located at the Arnold Arboretum and honors Revolutionary War soldiers from Jamaica Plain.

Green Space

John Hancock and Sam Adams had summer homes in Jamaica Plain – a common occurrence for prominent politicians and city-dwellers. Jamaica Plain was a green escape for those who spent most of their time in downtown Boston, a fact that Frederick Law Olmstead understood well. Olmstead was a firm believer in the idea that city folk needed parks, open land, and plenty of trees to balance out the hustle and bustle of city life. In fact, Jamaica Plain is so green that people refer to it as the “Eden of America”. In the 1800s, Olmstead, who was also the mastermind behind Central Park in New York City, designed Boston’s Emerald Necklace, a series of parks that line the city. Jamaica Pond and Arnold Arboretum rein the Jamaica Plain neighborhood.

Another lovely green space is the Forest Hills Cemetery. It is a beautiful area of gardens and gravestones, a representation of the reciprocal relationship between death and nature. It is a beautiful landscape that allows for peaceful solitude. Buried there are William Lloyd Garrison, a famous abolitionist, the playwright, Eugene O’Neill, and the poets Anne Sexton and E.E. Cummings. Its fountain, waterfall, and ample green space make for a great spot for quiet reflection. If you sit in quiet contemplation long enough, the spirits of the departed literary geniuses might inspire you.

Notable People

Accomplished Women of Jamaica Plain

Jamaica Plain was home to numerous historical figures, many of them women. Emily Greene Balch, a Nobel Peace Prize winner and advocate in the Women’s International League for Peace and Freedom, was a resident. She was just the second American woman to receive the award. Susan Walker Fitzgerald, a woman heavily involved in the women’s suffrage movement on the national level, and the first woman elected to the Massachusetts State Legislature, lived in Jamaica Plain.

The first woman to graduate from the Massachusetts Institute of Technology (MIT), Ellen Swallow Richards, lived on Eliot Street. Unfortunately, her Mediterranean-inspired abode is not one of the homes for sale in Jamaica Plain. It is a National Historic Landmark and popular spot to visit. In any case, some awe-inspiring women once walked these streets and continue to do so today.

James Michael Curley

James Michael Curley, one of Boston’s most famous mayors in the early 1900s, had a house along Jamaica Pond. Many Boston residents were shocked when Curly built the home since his salary was about four times lower than the cost of the house. City residents speculated that he got most of his money through corruption. Local gossips said that a cab driver used to drive around to all the old shops and businesses collecting money to drop at Curley’s house at day’s end. History remembers J. M. Curley not only for his questionable financial decisions. He also did some good things such as increasing community projects, such as libraries and pools. He even has an elementary school named after him- Curley K-8 School.

Breweries near Homes for Sale in Jamaica Plain

Jamaica Plain, since its beginnings, has believed in balance—a little bit of farm life, a little bit of beer. It appears not much has changed except, perhaps, the emphasis on farming. Currently, Jamaica Plain’s most popular tourist attractions are the breweries in their Brewery Complex. In the 1840s and 1850s there was an influx of beer makers moving to the States from overseas.

Jim Koch, the maker of Sam Adams beer, opened Jamaica Plain’s largest brewery in the 1980’s. Today, tourists and locals stop by to look around and try what Sam Adams is cooking up and developing. Their visitors may have some influence on what they actually stock in stores. Jamaica Plain’s famous bar, Doyle’s, is where Jim Koch first mentioned his desire to start Sam Adams beer. Doyle’s eventually sold the now-famous craft beer before it gained popularity. Besides that claim to fame, the likes of Ronald Reagan and Bill Clinton have had a pint of Guinness at Doyle’s. It is a stop along any beer-lover’s route.

Real Estate Values for Homes for Sale in Jamaica Plain

The current real estate market is booming in Jamaica Plain, even as the cold weather starts. In fact, most real estate agents suggest there is value in viewing a home for sale in Jamaica Plain during the colder months. You can get an idea of what the house and the neighborhood are like in the winter. The neighborhood has a wide-range of options for prospective homebuyers, with a market capable of selling over 200 homes in just 6 months.

Jamaica Plain’s rich history provides buyers with many antique, Victorian homes. Architectural styles brought about condominiums and looks that are more contemporary have a place in this neighborhood as well. Though the older homes might need some work, they offer some terrific real estate deals. They also provide attractive features that newer homes do not have. However, there are plenty of newly constructed homes that do not require renovation.

Buyers are constantly buying and developing residential and commercial properties; homes for sale in Jamaica Plain are going quickly. Realtors are erecting “for sale” signs just as fast as “Sold” signs, which is indicative of the growing interest in the community. Single-family, as well as multi-family homes are available. The median price of homes for sale in Jamaica Plain is $632,000. However, condominiums and homes can sell for upwards of $1 million. Last year, the lowest priced home sold for $555,000.There is something available for everyone in Jamaica Plain. There are also reasonably priced housing options such as the Julia Martin House and the Hyde Square Commons Condominium. These are both lovely, new developments in lively areas.

Transportation near Homes for Sale in Jamaica Plain

Trolleys once provided the residents of Jamaica Plain with transportation around the neighborhood. The city removed the streetcars in the 1980’s, which made more room for modern transportation. However, there are current discussions in Jamaica Plain about bringing the streetcars back. Jamaica Plain does utilize the trolley system occasionally for festival purposes. Everyone appreciates a little nostalgia, especially Jamaica Plain, so perhaps trolleys will be driving up and down Centre Street in the future.

Bikers are in abundance in Jamaica Plain, so the city is installing more bike lanes to accommodate the traffic. This is indicative of Jamaica Plain’s interest in environmental issues. There is ample access to the train and subway systems. When the need for escape and a change of scenery arises, or if you need to get to work, there are numerous railway stops to commute into downtown Boston. Orange Line stops, Jackson Square, Stony Brook, Green Street, Forest Hills, and Heath Street are all available for Jamaica Plain residents. If you drive, there are also plenty of parking options. Municipal parking lots are on Burroughs Street, Centre Street, and Hyde Square. Most street parking is free and plentiful, except some streets near the Orange Line where it is “resident permit only”. Residents can apply for resident permit parking free of charge

Schools and Education

If you are moving to Jamaica Plain with school-age children, there are both public and private options. Founded in 1676, The Eliot School of Fine and Applied Arts is Jamaica Plain’s oldest standing school. Since 1890, it has held crafting classes for both adults and children. You can learn woodcarving, knitting, or sculpting in this historic building. A plaque on the building attests to its educational legacy.

As for traditional public schools, elementary and middle schools such as Boston Teachers Union School and Joseph P Manning boast high test scores and good teacher-student ratios. Jamaica Plain’s public high schools are Community Academy, Greater Egleston High School, The English High School, and Margarita Muniz Academy. All of these schools have high ratings in terms of the Massachusetts average. When families with grade school-aged children purchase homes for sale in Jamaica Plain, Boston’s Public School system provides them with a list of school options in Tier I and Tier II performance categories. Test scores and other factors define the categories. If there are not enough Tier I and Tier II schools within 1 mile of the home, the city will provide the family with options.

There are private schools in the area, such as Neighborhood Schools, Meridian Academy, and British International School of Boston. Charter Schools are also available, such as Match Community Day Charter Public School. While there are no colleges in the Jamaica Plain neighborhood, there is a college counseling facility called Bottom Line College Counseling. The advising center, located on Amory Street, aids prospective college students in the application process and helps them become college-ready.

Amenities in Homes for Sale in Jamaica Plain

It is hard to leave Jamaica Plain once you are there. Homes for sale in Jamaica Plain are nestled among neighborhood-friendly restaurants, bars, and shops. Centre and South Main Streets have much to offer in entertainment.

Jamaica Plain’s districts are Hyde/Jackson Square, Eglestone Square, and Centre/South. The latter is the most popular for food, drinks, shopping, and entertainment. It is a bustling place, brimming with talented and interesting people. As for entertainment, the Footlight Club is the oldest community theater in the United States. Established in 1877, it stages numerous plays and performances from Legally Blonde to Pippin. The Footlight Club prides itself on being run by volunteers from stagehands to actors. It remains a great way to get involved in the Jamaica Plain community, even as an audience member.


It is no surprise that homes for sale in Jamaica Plain are going quickly, especially with all the lively fun, food, and shopping options in the area. Some of the best restaurants in all of Boston are in Jamaica Plain. Ten Tables on Centre Street is one of Jamaica Plan’s best restaurants. Its farm-to-table menu and cozy ambiance makes this a favorite date nightspot. Brassica Kitchen + Café provides good coffee and house made pastries during the day and dinners with locally sourced ingredients at night. Residents voted Exodus Bagels the best bagel shop in Boston, which is evident from the line around the corner on the weekends. The neighborhood knows them for their unique sandwich options on delicious bagels.

The possible neighborhood favorite is City Feed & Supply, a store that has everything you need. You can get your weekly grocery trip done while munching on a fresh breakfast sandwich. It is your one-stop-shop for everything. For dessert, check out J.P. Licks, a Boston-wide ice cream favorite that originated in Jamaica Plain.


Shopping destinations are plentiful in Jamaica Plain, with some notable second-hand and thrift stores. Diversity, Boomerangs, and 40 South Street are all popular stops for sifting through old treasures.

Papercuts is a woman-owned and operated bookstore, with a quaint, brick exterior and a cozy, welcoming interior where they house their books and frequent events. You will find Edwina by Jill Hofstra and A Home in the Heart of a City by Kathleen Hirsch on the shelves. Edwina is a compilation of a grandmother’s diary entries, illustrating her childhood and life in Jamaica Plain. A Home in the Heart of a City is Hirsch’s depiction of her home and life in Jamaica Plain, while taking the reader for a journey with several local characters. If you are not looking for a strictly Jamaica Plain story, you can sift through literary classics and current bestsellers.For art lovers, there is Two Boats Gallery. It is a great place to view the works of local artists and buy art for your new Jamaica Plain home.


Jamaica Plain has many notable festivals as well, providing a great way to get together with your neighbors and folks in the community. Celebrating its rich history, Jamaica Plain hosts the yearly Jamaica Pond Lantern Festival. It is just around Halloween, so participants tend to dress up and arrive early to make their own lanterns. There is live music, hot cider, great food, and a beautiful parade of costume-clad people carrying lanterns around Jamaica Pond. Another annual festival earlier in the fall is Jamaica Plain Music Festival. It is a – Jamaica Plain filled day, with local bands, entertainment, and local food and drinks. There are also children’s entertainment options to keep the younger ones happy while adults enjoy the music, food, and drink.

The Atmosphere in Jamaica Plain

Jamaica Plain is a vibrant, exciting place to live. There is always something going on, from festivals to shopping to dining and lounging. What makes Jamaica Plain so great is its diversity, its willingness to learn and adapt while still holding on to history. People from all walks of life coexist and enjoy what Jamaica Plain has to offer. Being close to downtown and Boston’s academic institutions such as Harvard, Boston College and Boston University, many people find Jamaica Plain to be the perfect middle ground between suburban and city life.

Jamaica Plain has done an excellent job of marrying their history with modernity. You can stroll down streets with coffee shops and vintage stores, while catching sight of war memorials and landmarks. Old-style Victorian homes are nestled among modern condominiums. None of it looks forced or misplaced; there is an evident harmony, a respect for many periods.

Homes for sale in Jamaica Plain have natural vistas and access to incredible parks and greenery. There are hundreds of sprawling acres on which to relax, lounge, and curl up on a blanket with a book from Papercuts or a picnic from City Feed & Supply. Residents can spend a day doing a myriad of activities. Jamaica Plain’s Branch of the Boston Public Library has much to offer adults and children. Fantastic shows are waiting for you at the Footlight Club. When that coffee craving calls, you can stop at Espresso Yourself or Caffè Nero on Centre Street. You can experience Arnold Arboretum for “Fall into Health” or “Fruits from the Sands”. Jamaica Plain, even with all of its history and tourist destinations, does not feel like a travel destination. If you buy one of the homes for sale in Jamaica Plain, you will instantly feel at home.

Parks near Homes for Sale in Jamaica Plain

When you buy one of the homes for sale in Jamaica Plain, you are acquiring access to some of the best and the most interesting parks in Boston.

Mozart Park

The most remarkable installation in Mozart Park is a sculpture called “Reach” created by Douglas Kornfeld. The sculpture consists of five stainless steel tubes symbolizing an outstretched hand. The hand is a tribute to immigrants starting life anew in the United States.

There are movies and snacks for children in the warm months. The park also has play areas and a basketball court.

Jamaica Pond

Jamaica Pond is part of the Emerald Necklace, a series of Boston area parks designed by Frederick Law Olmstead; The Muddy River that drains into the Charles River has its source here. The pond covers approximately 68 acres and is 53 feet deep at its deepest point. Those statistics make it the largest fresh water area in Boston. A 1.5-mile walking path circles the pond making this a very popular green space destination point. Residents love to row, walk, fish, and sail on this beautiful body of water.

This pond was, at one time, a reservoir for the cities of Boston and West Roxbury. In 1874, this pond provided employment for 350 men. The Jamaica Plain Ice Company harvested ice from the pond and sold it throughout the greater Boston area.

If you are interested in sailing, the Jamaica Pond Boat House is the place to go. Courageous Sailing is an organization that offers sailing lessons on Jamaica Pond and they work in cooperation with the Boston Department of Parks and Recreation. Rowboats and kayaks are for rent so no matter what kind of small craft you like, you can enjoy it on Jamaica Pond.

Interesting and Unique Stores near Homes for Sale in Jamaica Plain


This Jamaica Plain store is unusual in that it sells mainly hats. If fact, it has the largest selection of hats in New England; they stock approximately 12,000 hats! Many of the hats are custom made and are selected by the Salmagundi staff. The staff works hard to find the perfect hat for the patron’s occasion, lifestyle, and face. They sell hats and accessories for men and women and they will customize hats to suit their customers. They also carry dresses, ties, jewelry, gloves, handbags, and belts, Salmagundi is a family store; it is owned and run by a married couple, Andria Rapagnola and Jessen Fitzpatrick.


This is a small, but extremely well stocked kitchen supply store at 671 Centre Street. They also carry many whimsical items and designs that make perfect gifts.

Deep Thoughts

Deep Thoughts is a record store that seems to be lost in a time warp. It is a place to find all of the music you have loved for years but were unable to find elsewhere. The store is located at 138-B South Street and has vinyl records, stereo equipment, comics, books, cassettes, movies, and CD’s. They have new, used, and traded merchandise for you to explore. Many of the items were limited edition or rare. The décor is nostalgic and eclectic; you will definitely be entertained. This is the perfect place for a music lover.


This socially responsible store is located at 668 Centre Street. They are completely independent and uniquely different from other children’s clothing stores. The clothes are made of organic fiber and bought with the health of the planet in mind. They are very particular with whom they do business. The only companies that are suppliers are companies that use eco-friendly materials, manufacture in a sustainable manner, and treat workers well. Toys sold in this shop encourage imagination and have the safety of the child in mind. China makes none of the toys here. The staff in this shop practice what they preach. They strive for zero waste and use recycled labels, recycled packaging, recycled pens, and recycled stationery. When you buy a gift from this store, you are saying that you care.

Boing! Toy Shop

Boing! Toy Shop is located at 667 Centre Street. The owner, Kim Mitchell, loves the community of Jamaica Plain. She was very happy when the opportunity arose to purchase the toy store. The toy business was not her first career. She has a degree in finance and an MBA. She worked for Deutsche Bank but felt the disconnect one often feels in a large corporation. In a community-oriented environment, she enjoys constant interaction with customers and constant feedback. This store has a huge selection of fun and educational toys. The children in your life will thank you for shopping here.

Living in Jamaica Plain

Jamaica Plain, simply put, feels like home. Its local favorite spots, tree-lined streets, easy transportation systems, and friendly feel, contribute to its livability. The constant festivals, events, and happenings will keep you on your toes. The numerous green spaces are always there when you want to relax. Living in Jamaica Plain is like settling down without settling for less.

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