189 W Brookline St

An entire South End brownstone. One remarkable home. A truly distinctive opportunity in a market defined largely by condominium living, this offering presents the chance to own an entire classic bow-front brownstone on one of the South End's most beautiful & coveted tree-lined streets. Currently configured as two meticulously renovated residences, a penthouse triplex & garden duplex, the property has been transformed to near-new construction standards, bringing together timeless architecture, tailored interiors & exceptional flexibility under one roof. For those seeking the scale, privacy & permanence of a true townhome, the property offers the opportunity to combine both residences into one substantial single-family home, with conversion plans available for review. The existing configuration also provides immediate flexibility for multigenerational living, extended family, guests, an au pair or the ability to occupy one residence while generating income from the other. The approximately 2,518 SF penthouse triplex offers 3+ beds & 3.5 baths across three beautifully considered levels. Soaring ceilings, abundant natural light, custom millwork, gas fireplaces & refined finishes define the interiors, while a designer kitchen with custom cabinetry & high-end appliances anchors the main entertaining level. A private balcony extends from the kitchen, while an expansive private roof deck offers Boston skyline views, a built-in grill, integrated sound & fire pit. The approximately 1,802 SF garden duplex offers 2 beds & 2.5 baths across two generous levels, with beautifully proportioned living & dining spaces, a gas fireplace, custom cabinetry, integrated storage & curated finishes throughout. The living space opens directly to a substantial private patio for seamless indoor-outdoor living. Together, the residences provide approximately 4,320 SF of finished interior space, private outdoor living at both the garden & rooftop levels & 2 direct-access parking spaces. Moments from acclaimed dining, cafes, parks, SoWa, boutiques, galleries & premier private schools, this is a rare opportunity to move beyond the traditional condo & own an entire South End brownstone, ready to live beautifully today or become one extraordinary home for the future.