The Boston Home Team

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34 Olmstead Street, Jamaica Plain: 2 Family


2053 sqft total sqft | 6 beds (3 ea) | 2 full baths (1 ea) | 3068 sqft lot | 2 garage bays

List price: $899,000

You’re not seeing double! Built in the spring of 1927 by JA Ross of the well-established Ross Family Carpentry, on prestigious Olmstead Street, this architecturally unique, side-by-side two-family home is ready for someone to take it to the next level.

Each unit has 4 nearly identical levels, the middle two of which comprise the living area. On the main level: living room, dining room, kitchen with a back hall (future half bath?), and a screened and covered porch off the living room. The second floor has three bedrooms and a full bath. They each have an attic (accessible by scuttle or pulldown) with a surprising amount of head space beneath the tall gables). There is also a private basement and adjacent garage bay for each unit.

Both sides have their own yard space, too. Accessed from the halls behind each kitchen or through a gate just a few steps up the “Golden Staircase” there’s a patio-sized space, naturally secluded by the more than a century old cobblestone retaining wall for the abutting neighbors on Park Lane.

The structure itself, is comprised of two nearly identical halves turned a few degrees and put back together. Perhaps this was by design to give unit 1 (on the left) its front door on the Golden Staircase, a public foot path that is the extension of Park Lane, the cul-de-sac atop the stairs? Unit 2’s front door faces Olmstead, which gets great exposure to the sun! The structure itself was built on the sunset-facing side of the street which, in Parkside JP, can be magical. (There’s something about sunsets in that neighborhood that this listing team believes are magical).

And of course, there’s the neighborhood, Parkside in Jamaica Plain, which spans from contour of Franklin Park sloping down to busy and rapidly developing Washington Street. Once home to a small fraternity of mental health hospitals, Parkside JP—with the introduction of Franklin Park and Olmsted’s Emerald Necklace—became a haven for the super wealthy to build their Victorian homes parkside.

There are many types of buyers for whom this home could be a perfect find. There’s a great opportunity to renovate and convert into mini-townhomes? Or possibly a renovate and hold for income makes more sense to some. As it is, 34 Olmstead won’t be for everyone, but it has loads of potential!

Parkside JP, w/ its magical sunsets & equidistant proximity to green space, rapidly developing Washington St. & public transit (Green Street T stop is just a 1/2 mile away) is a can’t-go-wrong-location. With its historical charm, A+ location, 34 Olmstead represents a smart investment for the savvy buyer. It has everything else, just needs your vision!


  • A+ Parkside Location

  • Unique Side-by-Side Layout

  • Great Sun Exposure

  • Secluded Yard/Elevated off the Street

  • Updated Systems

  • Garage Parking!

  • Attic space for vaulted ceilings or easy AC placement.

  • Excellent Bones


Open House Times

Showings begin June 8th

Thursday, June 8th 2pm -4pm

Saturday, June 10th 11am- 1pm

Sunday, June 11th 12pm-2pm

appointments available Monday, June 12th


Useful Downloads

About the Home:

FAQ & Disclosures | Floor Plan | Original Building Permit Application (1927)

Mortgage Rate Sheet | MLS Page | Lead Paint Disclosure

Additional Downloads:

Offer Submission Instructions | TRID (truth in lending disclosure)


Location, location, location

See this map in the original post

Boston Home Team Favorites*

Brassica Kitchen - The best restaurant in JP? It’s up there. Their fried chicken sandwich is sinful.

Midway Cafe - This place is legendary. One of Boston’s oldest and most consistently rocking music clubs, the Midway offers an array of musical bookings for all tastes, in an unpretentious space where all feel welcomed.

Brendan Behan Pub - This is where the locals gather, in front, inside, and out back. A JP institution since the late 80s. Grab a late night bite from Food Wall across the street, and bring it over why don’t you?

Turtle Swamp Brewing - All of JP’s 19th century storied breweries are long gone, except for the celebrated Sam Adams, and then in 2017, Turtle Swamp opened on Washington Street and has since established itself as popular draw for JP residents with its events, family-friendly patio space and growlers to go. We give their JP Porter a thumbs up!

Third Cliff Bakery - A reputable, mobile bakery now in its first brick and mortar location. People literally come for miles to line up for its fare, including a wildly creative croissant menu.

Blue Nile - Lovely Ethiopian classics in a warm and friendly environment.

Seed - A locally owned and operated dispensary and social justice museum in the space once occupied by the erstwhile JP Bowl and old Milky Way Lounge & Lanes.

For Pizza we can’t pick just one: Same Old Place, Nemo’s, Il Panino, Ideal? There are too many to list!

Events and Organizations to Explore:

Franklin Park Coalition, Spontaneous Celebrations and W.U.T.E, JP NDC, JP Local First

* Editor’s note: There are so many more tasty spots in JP and if we listed them all, we’d be here all day. Once you buy this listing from the Boston Home Team, you’ll have all the time in the world to explore this rich and diverse food scene!


Meet the listing agents: The Boston Home Team

The Boston Home Team