
21 Hutchinson Winthrop — Photo 1 of 38
$1,260,000
Winthrop, MA 02152 — Winthrop Highlands
Beds
4
Baths
5
SqFt
3,705
Style
2 Family - 2 Units Up/Down
Built
1900
Completely renovated from its core with quality craftsmanship throughout, this exceptional two-family home blends modern luxury with the relaxed coastal lifestyle that makes Winthrop so special. Thoughtfully designed for comfortable everyday living, each residence spans two levels and offers its own distinctive layout, allowing for privacy and versatility whether you’re looking for a multi-generational home, an investment opportunity, or a place to live while generating additional income. Both units feature bright, open living spaces and beautifully finished white kitchens with upgraded cabinetry, modern appliances, quartz countertops and backsplash, and timeless finishes. Every bedroom offers the privacy of ensuite bathrooms and walk-in closets, with an additional half bath in each unit for visiting guests. High ceilings, hardwood flooring, in-unit laundry, central air with Ecobee smart thermostats add to the comfort and convenience of each home. Dedicated garage parking for each unit, along with electric vehicle charging stations—add an incredibly rare feature that adds both convenience and modern functionality. Located within walking distance of some of Winthrop’s favorite neighborhood spots for coffee, lunch, and dinner, this home also provides easy access to transportation and major routes into Boston and beyond. And when it’s time to slow down, Winthrop Beach is just moments away, offering the perfect backdrop for a morning walk along the shoreline, a relaxing beach day, or simply taking in the ocean breeze. Modern finishes, versatile living, exceptional parking, and a coveted coastal setting come together in this truly special two-family home. Whether you’re looking to live, invest, or create a home for multiple generations, this is an opportunity to enjoy the best of Winthrop while having the flexibility a two-family property provides.
* Analysis is based on 23 actively listed and recently sold comparable properties strictly within Winthrop, MA.
Range • Dishwasher • Disposal • Microwave • Refrigerator • Freezer • Washer • Dryer
Public Transportation • Shopping • Tennis Court(s) • Park • Walk/Jog Trails • Golf
Aug 14, 2026
MLS® 73563679
Aug 11, 2026
MLS® 73534743
Jun 11, 2026
MLS® 73534743
18,759
U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)
$116K
U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)
43.1%
U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)
2,527 housing units permitted in the last 12 months (+37% vs the prior 12 months) — 2,269 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jun '26)
Listing Agent: Atiyeh Cassidy
Listing Office: Blue Sky Realty
MLS® Number: 73563679
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