24 Lochstead Ave
Classic Form, Modern Ease
American Foursquare + Carriage House in the heart of Jamaica Plain
3,200 sqft. | 5 bedrooms | 3 full baths | 1 half bath | 2-3 Car Drive | 7500 sqft Lot | Finished Carriage House
Asking: $2,950,000
Overlooked detail: Lead lined stained glass transoms over front facing sash windows.
In the heart of Jamaica Plain — between Jamaica Pond and Centre Street— this 1906 American Foursquare carries real presence. Morning light ignites the stairwell through stained lead glass; original mantels, built-ins, and woodwork give the house its authentic voice. Decades of thoughtful upgrades follow that cue: nothing flashy, everything considered.
As we were doing our research on this incredible home, we spoke at length with the contractor who’s worked on almost every aspect of this home over the past 25 years. A local legend himself, Mr. Douglass told us that he’s never had a homeowner client who has done more for their home. It’s obvious from the moment you step onto the property.
Arrival begins on a broad, covered farmer’s porch — 29 feet of mahogany and ipe — that sets an easy, neighborly tone. Inside, front rooms read classic and comfortable: a sitting room with working fireplace to the left; a dining room with an ornamental mantel and a lead-glass china built-in to the right; a powder room tucked under the main stair. Rooms are well-scaled, ceilings airy, and the flow just works.
Dreamy and maple accented custom kitchen.
At the center, the kitchen understands daily life: an island for prep and conversation, clean-lined cabinetry, and smart storage. The double-skylit breakfast nook is the jewel —maple accents and seven slender windows wrapping the space like a terrarium. A glass door opens to the brand-new mahogany and ipe deck.
Out back, the landscape is a sequence of deliberate spaces. A red-brick herringbone patio, encircled by a sconce-lit quarry-stone border, anchors intimate dinners. A slightly elevated sandstone paver terrace lives between the main house and the carriage house — wide, flexible, and easy to furnish. At the carriage house door, a cobblestone apron adds texture and a subtle sense of arrival. Layered plantings frame it all, with lighting and irrigation keeping evenings luminous and upkeep simple. A sunken basketball area keeps play out of the main circulation, and the long, gated drive provides easy parking for two to three cars plus a charging station.
Wait until you see inside.
At the garden’s edge, the detached carriage house adds independence without distance. Its first level is open and social with a full kitchen, half bath, and a rustic wood ceiling; upstairs, a loft-like suite with great light and a full bath offers true flexibility. It is ideal for guests, creative work, or multigenerational needs—adaptable by design.
The second floor returns to classic Foursquare order: a center hall connecting four comfortable bedrooms and generous linen storage, with laundry close at hand. The hall bath is finished as a proper retreat, complete with a steam shower and radiant floors. Above, the top-floor suite gathers the home’s quiet luxuries: new wide-plank maple floors, three deep closets, built-ins, and a gabled reading nook. The bath pairs a soaking tub in the rear gable with a separate tiled shower—calm, bright, and restorative.
Nothing says “good morning” the way the sunlight cascades down through the stairwell.
The finished lower level expands how you live: a bright rumpus/exercise room, a full bath, storage and mechanicals, plus a bonus flex space for guests or growing family—perfect for overflow, projects, or focus time. Everywhere you look, care and thoughtful consideration shows up in the choices: the rebuilt rear deck (2025), the enduring slate roof with copper work, refreshed lighting, and floors that tell the story—oak through most of the house, red fir in the dining room, and new maple above. It all adds up to a prominent JP residence, a masterpiece—restored with intention, styled with warmth, and ready for what comes next.
The Boston Home Team is proud to collaborate on this listing with our esteemed colleagues, Jon Ufland and Margie Kern (a.k.a. the Margie and Jon Team).
Main house (~3,200 sf): gracious front rooms; powder room under the stair; island kitchen and a double-skylit breakfast nook wrapped by 7 narrow windows; glass door to a brand-new mahogany/ipe deck (2025).
Private spaces: classic second-floor center hall with 4 bedrooms; hall bath with steam shower + radiant floors; top-floor suite with new wide-plank maple, 3 closets, built-ins, soaking tub + separate shower, gabled reading nook.
Carriage house (detached, ~1,000 sf): main level with full kitchen, half bath, and rustic wood ceiling; upper level is a spacious, light-filled suite with full bath. Marketed as bonus space.
Outdoor living: fully fenced; red-brick herringbone patio with sconce-lit quarry-stone border; slightly elevated sandstone paver terrace between the house and carriage house; cobblestone apron at the carriage house door; sunken basketball area; irrigation + landscape lighting.
Porch/parking/systems: covered 29'×7' farmer’s porch in mahogany/ipe; driveway pkg for 2–3 + charging station; slate roof with copper work; high-efficiency boiler (2020); AC on 2nd/3rd floors; radiant in kitchen + 2nd-floor bath.
Lower level: bright rumpus/exercise room, full bath, storage/mechanicals, and a bonus sleeping space with egress (not a legal bedroom).
Open House Times
Thursday, September 18 11:30am - 1 pm
Remaining Open House Times TBD
Location, location, location
A Little About Jamaica Plain
For starters, locals call it JP. Once a vacation getaway for Boston’s elite merchants in centuries past, Jamaica Plain’s rolling hills are now home to a diverse and exciting fabric of community activism, an array of tasty restaurants and other small businesses, and many wonderful green spaces in and around the area. Surrounded by Olmsted’s Emerald Necklace, JP is one of the greenest neighborhoods in Boston.
Boston Home Team Favorites*
Life Alive - Organic and undeniably tasty bowls, wraps, soups, and smoothies, Life Alive is a personal team favorite.
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?
Tres Gatos - Now a staple on the block, Tres Gatos is a Spanish themed bistro style restaurant with a record/book store in the back. The folks who own and manage this spot are some of our favorite people, and they maintain Tres Gatos as a community-oriented establishment with frequent benefits in support of meaningful local causes.
The Galway House - If you’re a food snob, it’s best to stay away from the Galway. But if you like no-frills food that is consistently excellent with whipfast service at incredibly reasonable prices, then the Galway is the place for you. Also, their onion rings and steak entrees are in the conversation for the Best in Boston (easily).
Tonino - Classic Italian. If there was a prize for JP’s best all around menu, it would have to go to Tonino. Make a reservation now, because getting in to Tonino isn’t easy!
Chilacates - Authentic Mexican street food. Deeelish.
City Feed & Supply - Two locations in JP. The original “Little” City Feed is just a couple blocks from 24 Lochstead. Locally owned, locally sourced (when/where possible) foods and groceries. They have a yummy sandwich menu (farmer’s lunch, anyone?) and one helluva breakfast sandwich.
Blue Nile - Lovely Ethiopian classics in a warm and friendly environment.
For Pizza we can’t pick just one: Same Old Place, Mario’s, 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!
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