Welcome to 78 Oak Street, a home meticulously cared for and loved by the same family for generations. Inside, the main residence has an architectural richness that simply can’t be recreated in new construction. Exposed wood beams, warm natural materials, a gas fireplace and rooms with their own distinct character give the home a sense of history and permanence. The generous first floor allows plenty of space for cooking, gathering, working, relaxing and hosting, while three bedrooms are tucked upstairs. The indoor heated pool and hot tub make this property even more remarkable, offering a private place to swim, entertain, and unwind throughout the year. At the back of the home, a three-season room opens to a patio with a built-in grill and outdoor gas fireplace. Legally a two-family, the property lives more like a main residence with completely separate accommodations for extended family, guests or rental income. The private 1-2 bedroom apartment has its own entrance and basement, with no shared walls with the main house. An attached barn with loft sits between the two residences, providing substantial storage as well as exciting potential for future finishing or development. The expansive lot offers a broad, level yard around the house before rising up the hillside to elevated views. A two-car garage adds everyday practicality. All of this is set in Greenwood, one of Wakefield’s most convenient and coveted neighborhoods, .5 miles to the commuter rail, shops, restaurants and major routes. Rich in character and exceptionally versatile, 78 Oak Street is a home that could never be mistaken for anything ordinary!
| Units | 2 |
| Living area | 4,104 sqft |
| Lot size | 51,401 sqft |
| Year built | 1885 |
| Price / sqft | $292 |
| County | Middlesex |
| MLS # | 73577460 |
| Days on market | 0 days |
| Listed on | September 15, 2026 |
| Annual property tax | $11,243 |
| Tax year | 2025 |
| Assessed value | $990,600 |
| Zoning | SR |
| Gross income (actual) | $14,400/yr |
| Net operating income (actual) | $14,400/yr |
| Total actual rent | $1,200/mo |
| Stories | 3 |
| Total rooms | 13 |
| Lot size | 1.18 acres |
| Garage spaces | 2 |
| Parking spaces | 8 |
| Parking | Off Street |
| Basement | Full, Garage Access, Unfinished |
| Foundation | Concrete Perimeter, Block, Stone |
| Flooring | Tile, Hardwood, Wood |
| Heating | Oil, Natural Gas |
| Cooling | Central Air |
| Sewer | Public Sewer |
| Water | Public |
| Appliances | Oven, Dishwasher, Microwave, Range, Refrigerator, Washer, Dryer |
More about investing in Wakefield →
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 4,104 sqft of living area, built in 1885.
78 Oak St, Wakefield MA 01880 has been listed for 0 days (since September 15, 2026).
At a list price of $1,199,000 across 2 units, that works out to roughly $599,500 per unit.
Annual property taxes are $11,243 (2025), on an assessed value of $990,600.
At $1,199,000 for 4,104 sqft, that's about $292 per square foot.
2 garage spaces and 8 total parking spaces (off street).
78 Oak St, Wakefield MA 01880 is in Wakefield, Middlesex County, MA 01880.

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.