9 April
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Top Street to Live on in Boston’s South End | By Jeff Hamilton

In March of 2020, with Covid-19 taking hold and sales activity in the South End somewhat frozen, we decided to hold a competition to name the South End’s top street. We had always thought of ranking the streets in the South End but this finally seemed like the time to put the competition together for our Instagram audience. Just like the NCAA’s March Madness that we were all missing, we thought the competition for the best South End street would give our audience something to have fun with in an otherwise trying time. We were pleased to see that we collected almost 2,000 votes throughout the competition and thus feel that we have statistically significant results to consider in the aftermath.

At COG, we pride ourselves on our in-depth knowledge of Boston’s hyper-locales. Through its history, the South End has managed to maintain the charm that put its streets on the map in the first place. While its proximity to Back Bay and Downtown is a major plus, you’ll find some South Enders who rarely leave the coveted streets inside this neighborhood. Its residents love the supreme walkability, plethora of adorable playgrounds, and wide range of fabulous restaurants.  

We set up a 32 seed bracket for our Instagram followers to vote on. Polling real residents (and fellow agents) gave us deeper insights to their favorite South End Streets. For example, while the South End has plenty of streets and avenues, residents clearly favor it’s squares! While we knew some of the top seeds would perform well, there were some interesting underdog seeds that held their weight (and then some) throughout the challenge. 

Below you can see how the complete bracket for Battle of the South End Streets played out with additional commentary on individual matchups:


These are the streets we seeded. 


Union Park
The perennial power-house for South End streets came in as the top seed and cruised to the final four without much competition in its first two matchups. However, it surprisingly fell to underdog Concord Square in the semi final. The expansive, park setting in the middle of the street combined with the “center of the universe” location are a recipe for charm and convenience, alike! The Buttery, at the corner of Shawmut and Union Park has been a staple for this block since 2005 and certainly makes it easier to wake up in this neck of the woods with their fine coffee and pastries. Even in defeat, Union Park will return as a favorite South End street in future competitions!


Canton Street (Warren to Tremont)
The number two seed is the section of West Canton Street that is between Warren Avenue and Tremont Street. It is book-ended by Starbucks and Hayes Park, two attractive amenities for many! Many of the homes on this section of the street are single families. Very few of the buildings have been cut up into condos or apartments. Top pricing on this street rivals anywhere in the South End with home values pushing north of $5-6M.


Brookline Street (Warren to Tremont)

This third seed covers the section of the street from Warren Avenue to Tremont Street. Middling between parallel streets West Canton and Pembroke, this section has mass appeal. Along with the aforementioned streets, W. Brookline is a part of the Pilot Block sub-neighborhood. This family-friendly area offers no shortage of historic architecture on the brownstone lined streets such as this one. West Brookline street was uncontested in the first two rounds of the bracket before coming up short against Shawmut Avenue in a very tight contest. 


Hanson Street

The 4th seed, Hanson Street is located in the coveted Eight Streets sub-neighborhood. One thing that makes this street so special is it fronts Ringgold Park. That makes this street THE place to live if you have kids under 5 in the South End. From jungle gyms and swings to a basketball court and toys, the children that grow up on this South End street will have endless entertainment in their front yard. It’s not bad for the adults either… they can roll out of their living room to one of more than 20 bars and restaurants within a 5 minute walk.


Warren Avenue (Dartmouth to Pembroke)

This section of Warren Avenue (Seed 5) cuts through the Pilot Block, passes James Hayes Park and ends at picturesque Harriet Tubman Square. The award winning James Hayes Park is a welcoming oasis in the historic South End district of Boston. Featuring shade and flowering trees, benches for reading and relaxing, a toddlers’ play area, and changing displays of flowers throughout the seasons. The extra wide avenue (with two way traffic) is not a busy cut through street and gives this section a quiet appeal in the midst of the bustling city.


Montgomery Street

Montgomery Street is seed 6 in the best street in the South End Bracket. It is ideally located between the restaurants of Tremont Street and the nearby Back Bay Station and Copley Mall. This notable street backs up to the secret garden known as Montgomery Park. Montgomery Park is awesome. If ya don’t know, now you know! 


Ringgold Street

The 7th seed is Ringgold Street. Home to the famous Ringgold park, this street intersects Hanson and Waltham in the Eight Streets sub-neighborhood. This street is one of the smaller streets nominated in the top South End street Bracket but on warm days Ringgold Street is every young family’s backyard in the South End. And, on Halloween the neighborhood convenes in your front yard for a celebration that is rivaled only by Beacon Hill’s extravaganza. 


Appleton Street (Clarendon to Dartmouth)

The eighth seed in our bracket is the section of Appleton Street from Dartmouth Street to Clarendon Street in the Golden Triangle. The street won the first two rounds of the competition in a landslide until facing off against top seeded Union Park in the third round. This one way street is wide and offers tall brownstones, many of which have mesmerizing roof decks to take in the Back Bay skyline.


Rutland Square

Seed 9: W. Rutland Square. Sneakier and less known than most, West Rutland Square may have deserved better in this competition of the best South End street. This is the only South End street that ends in a culdesac. It is also one of the few streets in the competition from which you could throw a stone into the Back Bay.  Facing large and impressive Titus Sparrow Park gives the street an amenity and an entertainment platform on summer nights when concerts take place in the park., In one of the larger early round upsets, Rutland Square fell to Lawrence Street in the first round.


Rutland Square

This extension of W. Rutland Square is Seed 10: Rutland Square. This section of street lasted longer in the bracket than its counterpart. Taking out Dwight St., Warren Ave., and making it to the round three before falling to W. Canton Street. Rutland Square features a concentration of single family residences that look over the English style square in the middle of the two way street.


Shawmut Avenue (Union Park to Dwight)
The section of Shawmut Ave between Union Park and Dwight Street is our 11th seed: a double wide, one way street. It has plenty of room for the legal/illegal(?) double parking that is so common around Boston. Since the street doesn’t offer alley parking for residents, the double wide nature is convenient. This is also a retail corridor with many boutique shops and restaurants. Formaggio, Coppa and Flock to name a few. It has very easy access to restaurant row as well as to the deeper section of the South End including SoWa and the newer amenities of the Ink Block (Whole Foods!). We did not expect the 11th seed to make the finals but it was quite a run and people clearly appreciate what this street offers in terms of location and amenities.


Milford Street

Seed 12, Milford Street is the quiet, brownstone-lined street connecting the retail corridors on Tremont and Shawmut Avenues. This juxtaposition of lifestyles creates the best of both worlds living experience that the Eight Streets is known for. Real estate on Milford Street is some of the South End’s most sought after – and for good reason. As is the case for most of 8 Streets, there is no private parking offered on Milford Street.


Pembroke Street

Seed 13 was overtaken early in the battle by the Southwest Corridor section of W. Canton Street. This street has great positioning in the Pilot Block but does have a cut through nature that makes it slightly less desirable than its neighboring streets of West Brookline and West Canton.


Chandler Street (Clarendon to Dartmouth)

Chandler Street landed seed number 14 in this year’s best South End streets competition.  This street sector is a one way double wide with parking on each side between Clarendon and Dartmouth. While this street was anticipated to make it further in the competition, it was up against one of the top runners Shawmut Ave, ending it’s battle in round 1. 


Waltham Street (Tremont to Shawmut)

The 15th seed, Waltham Street is known to be locals’ go to for Halloween. Walk down Waltham Street on Halloween night, and you’ll see plenty of spooky set-ups and trick-or-treating while the street is closed to cars. Waltham Street is more than just Halloween, though. It is one of the most central streets within the South End connecting Tremont all the way to Harrison Street.


Bond Street
Bond Street landed seed 16 in the South End top Streets Bracket. One of the shortest and least populated streets in the competition, Bond does not lack for charm! Many of the homes on this street are single families and you don’t have to worry much about traffic on this cute corner.


West Newton Street (Tremont to Columbus)

Seed 17, W. Newton, is one of the common through ways between South End and Back Bay. Lined with quintessential brownstones with large front staircases, this little strip of West Newton is commonly travelled by vehicles and people on their travels to Back Bay. This street falls within our Pilot Block neighborhood for data tracking purposes and has a very convenient locale with access to Tremont and Columbus services and food. 


Braddock Park

Seed 18, Braddock Park was overtaken early in the battle by Waltham Street. Braddock Park is a “finger” like street that saddles up to the Southwest Corridor. Limited traffic drives down this street and the houses look down upon a beautiful, English style square, just like many of the other favored streets in the South End.


Holyoke Street 

Seed 19 is home to some major 2019 South End real estate sales. Although its larger sub-neighborhood, Southwest Corridor Annex, ranked 5th in 2019 for South End sub-neighborhoods in both sales volume and price per square foot, thanks to Holyoke Street it was home to the property that sold with the highest sales price and the property that sold with the highest price per square foot in the entire South End that year. 


Canton Street (Southwest Corridor)

This section of W. Canton Street that was picked as the 20th seed was looking like an underdog champion through the first few rounds. This section falls closer to the Southwest Corridor on the north side of Columbus Avenue. On this street residents enjoy all the perks of city life – with the added bonus of easy access to one of Boston’s largest parks. The Southwest Corridor Park is a haven for naturists, families, and dog lovers—and close at hand are some of Boston’s tastiest eateries, plus some of the best nightlife the city has to offer just across the “border” in the Back Bay.


Appleton Street (Clarendon to Berkeley)

Seed 21, Appleton Street from Clarendon to Berkeley Street was taken out by champion Concord Sq in the second round after annihilating Milford Street in the first round. This section of Appleton was seeded below its sister section that connects Dartmouth to Clarendon due to a slightly darker, grittier feel when compared to the adjacent block. The proximity to busier Berkeley Street influences this feel.


Chandler Street  (Clarendon to Berkeley)

Chandler Street from Clarendon to Berkeley landed as the 22nd seed in the South End top Streets Bracket. This street is home to two small dead end streets sectoring off of Chandler St., St Charles Street and St Cazenove St. It features premier access to the Back Bay.


Dwight Street 

Seed 23, Dwight Street is another classic, brownstone-lined street in the Eight Streets sub-section of the South End. It is the only street in the 8 Streets Neighborhood that offers alley parking behind one side of its brownstones.


Lawrence Street

This quiet one way street was seed number 24. The street is mostly lined by single family homes and was victorious in the first round before falling to Appleton Street shortly after. There are no commercial operations on Lawrence Street and if you blink, you might miss it.


Upton Street

Seed 25, Upton Street is an entirely residential street (it’s only 675 feet in total length) that connects the more heavily pedestrian stretches of Tremont and Shawmut Avenue where retail options await neighborhood strollers. It was an especially interesting case in 2019 as there were 8 properties listed for sale on this street alone. Both sides of Upton Street offer alley parking, which is rare in this area of the South End.


Warren Avenue (Dartmouth to Berkeley)

The 26th seed, this section of Warren Ave is not as highly sought after as its sister section on the other side of Dartmouth. Instead of cutting through the Pilot Block, this section is in the Golden Triangle. Even still, this is a tremendous location with great access to both Back Bay and restaurant row. Although seeded lower, this pick survived two rounds of the bracket demonstrating the strength the crowd sees in it


Gray Street

Seed 27, Gray street is another single lane, one way street in the Golden Triangle. With commercial hubs on either end (South End Buttery Annex, Irving Glick Florist shop and Revolution Hotel), this street is less common to vehicle traffic allowing it to grab a spot in the bracket. The tree lined quiet residential feel, filled with brownstone townhouses didn’t quite grab the attention of our voters, allowing Gray st. to fall to Montgomery St in round one. 


Concord Square

Admittedly, we never would have guessed that Concord Sq, the 28th seed, had a shot at the crown this year… but, the people have spoken and they clearly like their “squares.” Lots of supportive neighbors and friends came to bat for this year’s crowd favorite. With premier access to the Back Bay’s Prudential Center and parking alleys on either side of the street, Concord Square can be a very practical place to live. It’s also very close to parks and conveniences like Titus Sparrow and the South End Library branch plus great restaurants like SRV, Petit Robert and more. Congrats to Concord Square for a well earned victory… but let’s see if it can defend in next year’s competition before we go too far out on a limb!


Newton Street (Titus Sparrow Park)

Seed 29, W. Newton Street backs up to the green oasis located in the South End known as Titus Sparrow Park. A lively and historic Boston neighborhood. The park has many features and free community programs sponsored by Friends of Titus Sparrow Park, an all-volunteer non-profit organization. This street actually transitions from the South End to the Back Bay as you make your way past Titus Sparrow Park. Its hinterland status, while a nice to have on paper, may not be as desirable based on its traffic count.


Bradford Street

Another South End hidden gem is Bradford Street, tucked between Waltham Street, Peters Park and Shawmut Ave. Peter’s Park is one of the largest parks in the neighborhood featuring a tennis court, a baseball field, basketball and the South End’s largest dog park. The dog park at Peter’s Park is known for being the first city-sanctioned dog park in Boston. The park is maintained by the Friends of Peter’s Park and kept in near pristine condition. 


Tremont Street (Dwight to Dartmouth)

This area of Tremont Streetthat was designated as the 31st seed is known for its restaurants and sometimes referred to as Restaurant Row. A vibrant, commercial hub teeming with boutiques, distinctive restaurants, and cultural gems large and small, it attracts visitors from all over the city and beyond on a weekly basis.


Columbus Avenue (Clarendon to Dartmouth)

Well, being “Columbus & Over,” we had to get it in there! Columbus Avenue is the dividing line between the Back Bay and the South End. This specific section that makes up seed 32, falls within the Golden Triangle. This is the perfect place to live if you are looking for easy accessibility to the Back Bay and Financial District not to mention the bounty of restaurants and bars that can be found within the South End. Columbus Avenue is a great place to spend an evening – or a lifetime. 


Want to go deeper on the  best streets in the South End? Columbus & Over Group is your hyper-local expert – We love this stuff. Whether its ranking the streets of the South End or trying the newest restaurant or understanding neighborhood culture, we’re here for you. Let us know if we can help you find a way in or if we can introduce your home to its next lucky resident!