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.
| Units | 2 |
| Living area | 3,705 sqft |
| Lot size | 5,000 sqft |
| Year built | 1900 |
| Price / sqft | $340 |
| County | Suffolk |
| MLS # | 73563679 |
| Days on market | 0 days |
| Listed on | August 14, 2026 |
| Annual property tax | $9,316 |
| Tax year | 2026 |
| Assessed value | $836,300 |
| Zoning | 2 Family |
| Total actual rent | $0/mo |
| Stories | 4 |
| Total rooms | 9 |
| Lot size | 0.11 acres |
| Garage spaces | 2 |
| Parking spaces | 7 |
| Parking | Paved Drive, Off Street, Tandem |
| Basement | Full, Finished |
| Foundation | Concrete Perimeter |
| Roof | Shingle |
| Construction | Frame, Stone |
| Flooring | Tile, Hardwood |
| Heating | Forced Air, Natural Gas |
| Cooling | Central Air |
| Sewer | Public Sewer |
| Water | Public |
| Utilities | for Gas Range, for Gas Oven, for Electric Dryer |
| Appliances | Range, Dishwasher, Disposal, Microwave, Refrigerator, Freezer, Washer, Dryer |
More about investing in Winthrop →
Listing courtesy of a MLS PIN member office. Listing data © MLS PIN.
Auto-generated from the listing data — richer AI answers coming with the live site.
It is a 2-unit multi-family property with 3,705 sqft of living area, built in 1900.
21 Hutchinson, Winthrop MA 02152 has been listed for 0 days (since August 14, 2026).
At a list price of $1,260,000 across 2 units, that works out to roughly $630,000 per unit.
Annual property taxes are $9,316 (2026), on an assessed value of $836,300.
At $1,260,000 for 3,705 sqft, that's about $340 per square foot.
2 garage spaces and 7 total parking spaces (paved drive, off street, tandem).
21 Hutchinson, Winthrop MA 02152 is in Winthrop, Suffolk County, MA 02152.

Justin Rollo is a Broker Associate with Signal Real Estate (MA Lic. #9534264) and a lifelong Massachusetts resident. Over 14 years and hundreds of transactions, he has worked investment properties — multi-families and house-hacking — across Greater Boston full-time. Away from real estate, Justin is a proud dad, youth coach and local school-committee member — and a former professional poker player who still loves golf and following local sports.