At the top of Winthrop’s Highlands, where the town quietly saves its best views, 144 Quincy Avenue serves up a briny mix of elevation, design, and proximity to the Atlantic.

From this hilltop setting, the Boston skyline stretches across the horizon, delivering dramatic sunset views that feel cinematic. Winthrop has always attracted buyers who want a coastal lifestyle without giving up access to the city. From this address, ocean walks, beach days, and downtown Boston all fit easily into the same day.

Recently rebuilt with a distinctly modern sensibility, the home features wide white oak floors, intentional lines, and warm, pared-back finishes give the interiors a calm confidence. The main living level is designed around how people actually live now: an open flow anchored by a professional-grade kitchen with an oversized island, beverage bar, and walk-in pantry. Expansive windows pull the skyline into the space, while a sleek gas fireplace adds focus without competing with the view. A deck just off the living area turns both nightcaps and morning coffee into a daily ritual.

Flexibility is one of the home’s strongest assets. There is so much packed into the property’s whopping 3,900 square feet. A fully independent lower-level suite—complete with its own kitchen, entrance, and laundry—creates options for extended family, guests, or rental income without sacrificing privacy. Upstairs, the primary suite feels like a retreat, with a spa-inspired bath and quiet moments of skyline views, while additional bedrooms offer space for family or work-from-home needs.

A tiered backyard offers tons of room for outdoor living and entertaining, and your guests can park in one of your three dedicated spaces.

Open house hours are Saturday, January 10, from 11 a.m. to noon.

The sale of the home, on the market for $1,699,900, is represented by Leighann Eruzione with Lantern Residential, 617-799-4810.

Hot Property Fri Jan 9 2026 – 144 Quincy Avenue, Winthrop, MA 02152
Hot Property Fri Jan 9 2026 – 144 Quincy Avenue, Winthrop, MA 02152
Hot Property Fri Jan 9 2026 – 144 Quincy Avenue, Winthrop, MA 02152