Brookline and Jamaica Plain meet along the Muddy River, where Olmsted Park on the Brookline side runs into the Jamaicaway and Jamaica Pond on the Boston side. From Brookline Village to Hyde Square is a short trip, and both places grew up as nineteenth-century streetcar suburbs with plenty of Victorian housing. The line on the map still decides a lot, because one side is a town and the other is part of a city. Our Brookline guide and Jamaica Plain guide go deeper on each.
A town and a city neighborhood
Brookline governs itself through a Select Board and Town Meeting. Jamaica Plain is one of Boston’s neighborhoods, governed by the mayor and City Council, and it has been since West Roxbury was annexed in 1874.
See the Brookline Assessor’s Office and our Boston residential exemption page for how each exemption works, and property tax rates in Greater Boston for the full table. The Public Schools of Brookline serve the town and Boston Public Schools serve JP; state profiles for both are at profiles.doe.mass.edu.
The housing on each side
Brookline
North of Route 9, the market leans toward condominiums. Brick apartment buildings from around the turn of the twentieth century line Beacon Street and the blocks near Coolidge Corner and Washington Square, and many Victorian two- and three-families on the side streets have been split into units. Corey Hill, Fisher Hill and Pill Hill hold larger single-families, and Chestnut Hill and South Brookline have more twentieth-century houses on bigger lots.
Jamaica Plain
JP’s stock dates mostly from the 1870s through the 1920s. The flatter land near the Southwest Corridor is lined with triple-deckers and two-families, a large share of them converted to condos. Around Sumner Hill, Pondside and Moss Hill the lots open up and the houses become Victorian, Queen Anne and Colonial Revival single-families. Newer condo buildings have gone up around Jackson Square and along Washington Street toward Forest Hills.
What that means for a purchase
In practice, a Brookline search often turns on condo association documents in a larger brick building, while a JP search more often weighs a triple-decker unit against a two-family with rental income. Our multi-family guide and mortgage options by property type cover how those purchases differ.
Historic review
Brookline
Brookline has eight local historic districts created under state law (Chapter 40C): Chestnut Hill North, Cottage Farm, Crowninshield, Graffam-McKay, Harvard Avenue, Lawrence, Pill Hill and Wild-Sargent.
Jamaica Plain
No part of JP is a Boston Landmarks Commission district. Sumner Hill (listed 1987) and the area around Monument Square (listed 1990) are on the National Register of Historic Places, which recognizes them but does not by itself add design review for private owners.
Getting around
Brookline
Brookline has two Green Line branches. The C branch runs in the median of Beacon Street, and the D branch stops at Longwood, Brookline Village, Brookline Hills, Beaconsfield and Reservoir. Both continue through Kenmore to downtown. The MBTA has been reworking C branch stops for accessibility, so check the current station list on mbta.com. There is no commuter rail station in town.
- Longwood
- Brookline Village
- Brookline Hills
- Beaconsfield
- Reservoir
Jamaica Plain
JP runs along the Orange Line’s Southwest Corridor, with Jackson Square, Stony Brook, Green Street and Forest Hills. Forest Hills is also a busway and a Needham Line commuter rail stop, with limited stops by some Franklin/Foxboro and Providence/Stoughton trains, and the Green Line E branch ends at Heath Street on the Mission Hill edge.
- Jackson Square
- Stony Brook
- Green Street
- Forest Hills
The Green Line guide and Orange Line guide go stop by stop.
Parking
Parking is where the two differ most day to day.
In either place, confirm whether a listing includes a deeded space, a driveway or nothing at all.
Shops, parks and landmarks
Brookline
Brookline’s errands center on Coolidge Corner at Beacon and Harvard Streets, home to the Coolidge Corner Theatre; Brookline Village along Washington Street and Route 9; and Washington Square farther out on Beacon. Larz Anderson Park and the Brookline Reservoir provide open space toward the south. Two National Park Service sites are in town: the John F. Kennedy birthplace on Beals Street, and Fairsted, Frederick Law Olmsted’s home and office, on Warren Street.
Jamaica Plain
In JP, Centre Street carries most of the storefronts from Hyde Square through JP Center to the Monument, with South Street continuing toward Forest Hills. Jamaica Pond, the Arnold Arboretum’s main gate on the Arborway, Forest Hills Cemetery, Franklin Park and the Southwest Corridor Park make up much of the neighborhood’s edges.
Shared ground
The two share the Emerald Necklace. The Riverway and Olmsted Park follow the town line, so a walk from Brookline Village to Jamaica Pond stays in parkland most of the way.
Compare specific homes with us
Two homes a mile apart across this line can carry different tax bills, parking rules and review requirements, and values move street by street on both sides. For recent sales near a particular address, get in touch or start a search.