S
Steve City
Verified Google review · 5 stars
★★★★★
“I had my Winthrop condo listed with another agency for over three months and had very little traffic. I decided to work with Seth and it was the best decision we made. He had a lot of traffic the first weekend of his open houses and within a very short period of time we had an offer and essentially at asking price. I am a real estate developer and Seth’s team and operation are second to none in the industry! We are beyond pleased and grateful! Thank you, Seth.”
Short answer: The best streets in East Boston in 2026 are grouped into three neighborhoods – Jeffries Point for harbor views and walkability, Eagle Hill for Victorian homes and skyline views, and Orient Heights for space, views and the quietest feel in Eastie. Below are our favorite streets, why they’re important, and what you’ll have to pay to live on them.
Why East Boston, why now
East Boston (all the locals call it Eastie) has become one of the most sought-after neighborhoods in the city, and for good reason. You get a waterfront neighborhood, a Blue Line ride downtown that’s often faster than the ride from the Back Bay, some of the best views of the Boston skyline in the city, and prices that are still below the South End, Charlestown, and the Seaport. The demand is real: Monthly search volume for “houses for sale in East Boston” and “real estate in East Boston” is a combined 14,700 searches. Buyers pay attention.
Before we hit the road, a note on geography. Eastie isn’t a single neighborhood – it’s made up of a handful of different neighborhoods tied together by Bennington, Meridian and Saratoga Streets. The “best” street depends entirely on whether you want a new build on the waterfront, a Victorian three-decker with harbor views, or a quieter family home on a hill. We’ll go through each one.
Jeffries Point: Walkable waterfront promenade
Jeffries Point is located directly on the harbor across from the Seaport, through which the East Boston Greenway runs and Piers Park offers arguably the best view of the city’s skyline. It’s the most walkable area of Eastie and the one we recommend most to buyers from the South End or Back Bay who want to be near the water without paying Seaport prices.
Outstanding Streets in Jeffries Point
- Edge road. Runs along the harbor and is home to a mix of renovated brick warehouses, new condos and classic apartment buildings. The views are second to none and the location puts you just seconds from the Greenway and Piers Park.
- Webster St. Slightly inland but still within walking radius of the water. Strong mix of renovated triple deckers, quiet nights, and direct access to Maverick Square for the Blue Line.
- Cottage Street. Closer location, more residential and one of the blocks where we see the most sustained buyer interest. Characterful houses with a smaller footprint but great charm.
- Lewis Street. It is home to Lewis Street Mall and is close to KO Pies, the Long Wharf ferry and ICA Watershed.
Eagle Hill: Victorians, Revolutionary War Views and Streets
Eagle Hill is exactly what the name suggests – a hilltop neighborhood with some of the best water and skyline views in the city. The grid is fun: east-west streets are named after Revolutionary War battles (Saratoga, Lexington, Trenton) and north-south streets are named after generals (Marion, Brooks, Putnam). Victorian homes, brick three-decker homes, and numerous newly converted condos make this the most architecturally rich part of Eastie.
Outstanding streets on Eagle Hill
- Eutaw Street. A quieter residential area near the top of the hill with excellent views and a range of single family, triple and condominiums. Strong long term owners on this block.
- Putnam Street. Buyers keep coming back to the north-south axis. Victorian buildings, bay windows and a real neighborhood atmosphere.
- Trenton St. Passes through some of the hill’s most beautiful viewpoints, particularly at the eastern end. Mixture of updated and original triplanes.
- Brooks Street. A little more functioning, a little more authentic, with good prices compared to the surrounding grid.
- Lexington St. Commercial properties in the western part, residential areas in the east, with access to the shops and restaurants of Central Square.
Orient Heights: space, views and tranquility
Orient Heights is the northernmost part of East Boston, reaching an elevation of 152 feet above sea level at its highest point – meaning it offers breathtaking views of Revere, Chelsea, Winthrop and Belle Isle Marsh, the largest remaining salt marsh in Boston. If you’re looking for a single-family home with a driveway, yard, and Blue Line stop within Boston city limits, Orient Heights is usually the answer.
Outstanding Streets in Orient Heights
- Barnes Ave. A street at the top of the hill with large lots for Eastie and some of the best views. Single-family homes trade here when they show up, and that doesn’t happen often.
- Boardman Street. Quiet, family oriented and just a short walk to the Orient Heights Blue Line.
- Faywood Ave. One of the most consistent apartment blocks in Orient Heights – well-maintained homes, long-term owners and easy access to the Blue Line and Constitution Beach.
- Saratoga Street (above). The main artery connecting Eagle Hill to Orient Heights. Where Saratoga climbs into Orient Heights offers great views and an easy drive in either direction.
What you can expect from the price
Prices vary greatly by street and property type, but here is a working framework as of Spring 2026:
- Jeffries Point Condo (1-2 Bedroom Renovated): generally $650,000 to $950,000 depending on views and outdoor space.
- Eagle Hill Apartment (1-2 bedroom triple converted Victorian): generally $525,000 to $825,000.
- Triple-decker apartment building (Eagle Hill or Jeffries Point): often in the $1.2 to $1.8 million range depending on condition.
- Single family home in Orient Heights: typically between $750,000 and $1.2 million, plus hill and view bonuses.
These numbers are moving. For the most current inventory and sold comparisons, view the live East Boston homes for sale page or contact us. We then make specific comparisons for the block you are currently viewing.
Getting Around (The Advantage of Quiet East Boston)
Buyers from Charlestown, the South End or the Back Bay are often surprised at how well-connected Eastie is. The Blue Line runs through Maverick, Airport, Wood Island and Orient Heights – all within a 10-minute drive to State Street. The MBTA ferry from Lewis Mall will take you to Long Wharf in about 8 minutes. The Sumner and Callahan Tunnels provide quick driving access to the Seaport or North End. And the airport is a 5-minute drive or one stop on the Blue Line, which, depending on how much you travel, can be the biggest quality of life improvement of any Boston neighborhood.
What our customers say
“Seth is incredibly knowledgeable, professional, honest, transparent and overall very easy to work with. At no point did we feel pressured into purchasing and Seth made the entire process an amazing experience! Thank you, Seth!”
— Michael Disabatino5 stars (read more reviews)
Frequently asked questions
What is the safest part of East Boston?
Most of Eastie is quiet residential areas and has become significantly busier over the last decade. Orient Heights and the upper parts of Eagle Hill tend to feel the quietest, while Jeffries Point offers a busier, more pedestrian-friendly atmosphere that feels more South End in terms of pace.
Is East Boston a good investment in 2026?
Compared to Boston’s surrounding neighborhoods, East Boston still offers the best value in the city due to its waterfront access, transportation, and proximity to the airport. The over 14,700 total monthly searches for East Boston real estate underscore continued buyer demand.
How do I choose between Jeffries Point, Eagle Hill and Orient Heights?
If walkability and water access are top priorities, Jeffries Point is for you. If you want Victorian character and skyline views, Eagle Hill is for you. If you want space, a driveway, and the most serene atmosphere, Orient Heights is for you.
Can I get a single family home in East Boston?
Yes, although they are more common in Orient Heights than the rest of Eastie. Most single-family home properties trade off-market or within the first week of listing. Therefore, it is important to work with a local agent who researches homes before listing.
Want to tour East Boston?
If any of these streets catch your eye, we would love to walk them with you. The reference team knows every block in Eastie – where the views are truly the best, where airport noise is a factor and where it isn’t, and which blocks are currently trending with buyers. Contact us and we will put together a tour.
For more information about Boston neighborhoods, check out our 2026 Boston Condo Buying Guide with prices for each neighborhood, as well as our live East Boston listings. Thinking about selling a property in Eastie? Our guide to the best time to sell a house in Boston in 2026 lays out the full spring strategy.
