Medford Square Painters — Old center, hillside subdivisions
The streets around the five-way intersection mix early-1800s house lots, a local historic district, hillside subdivisions filled before 1930, and apartment houses built from about 1925 on.
A town center that grew up the hill
In the Historical Commission's survey, the Medford Square neighborhood runs from the Mystic River north to the Middlesex Fells, between Winthrop Street and I-93. Its homes come in layers. Ashland and Oakland streets were platted with small lots early in the 1800s, and by the 1875 map they held end and cross-wing houses in Greek and Gothic modes plus at least one hipped-roof Italianate. By 1898 Queen Anne houses had joined them, and duplexes went up on the west side of Ashland. The survey calls this pocket the only 19th-century subdivision in the neighborhood.
Uphill, Governors Avenue, Bradlee Road, Woodland Avenue and the Prospect Park streets filled with large houses before 1930. The survey singles out boxy two-story hipped-roof houses: Colonials with wood siding, ornate cornices and porches, and Craftsman versions finished in stucco. Farther north, the Traincroft and Lawrence Estates subdivisions of the 1920s are mostly Colonial, Tudor and Dutch Colonial, and the survey calls brick a defining material across that whole tract (see our Lawrence Estates page).
The center is also where some of Medford's earliest apartment houses appeared. The survey counts a Mediterranean-style three-story building at 148 High Street, from about 1925, among the first in the city. Around 1930 a group of four-story blocks went up behind High Street between Governors Avenue and Forest Street. Later, more apartment buildings followed, and old commercial buildings and the Lawrence Armory were converted to housing. In Census Tract 3391.01, which includes addresses on Oakland Street, Hillside Avenue, Bradlee Road and Traincroft Street, 51.0% of housing units are in buildings of 50 or more units.
What makes Medford Square projects distinct
Hillside Avenue is a local historic district
The city lists two local historic districts, Hillside Avenue and Marm Simonds. Its Historic District Commission reviews exterior alterations and repairs visible from public ways. The 1975 National Register nomination describes twenty houses on Hillside and Grandview avenues, mostly built after 1889 and designed by architects in Queen Anne, Shingle, Colonial Revival and Tudor Revival styles. On these two streets, check with the commission before exterior work starts.
Wood, stucco and brick on one hill
Within a few blocks you can find clapboard Colonials with heavy cornices, stuccoed Craftsman houses, shingled Prospect Park homes and brick-veneer Tudors. Each needs different prep and coatings. Painted wood needs scraping and priming at failed spots. Stucco needs cracks patched and a breathable masonry finish. Unpainted brick is usually best left alone, so the work there is limited to trim, windows and doors.
Vinyl over Victorian trim
The survey reports that many houses in the neighborhood now carry synthetic siding and replacement windows. The 1975 Register nomination already recorded aluminum siding on two houses in the Hillside Avenue district and white vinyl on a third. On a re-sided house, the paintable surfaces are often limited to porches, cornices, doors and any surviving wood trim. On an older house, those pieces may also carry the earliest layers of paint.
Apartment blocks and condo buildings
The survey records interwar apartment blocks here, and later conversions of commercial buildings and the Lawrence Armory into multiple dwellings. If your unit in one of them is a condo, the association generally controls the common hallways, stairwells and exterior, while you decide on the walls, ceilings and trim inside, subject to the condo documents. Condo painting covers how that split works.
Medford Square at a glance
| Units in buildings of 50+ units (Census Tract 3391.01) | 51.0% of 1,882 units; single-family detached 20.1% (U.S. Census ACS 2020–2024 5-year, table B25024) |
| Median year built (Census Tract 3391.01) | 1964; 31.2% of units built 1939 or earlier, 73.5% before 1980 (U.S. Census ACS 2020–2024 5-year, tables B25034 and B25035) |
| Hillside Avenue Historic District | 20 houses on about 7 acres; National Register 1975 (National Register nomination form, Massachusetts Historical Commission (1975)) |
| Local historic districts in Medford | Two: Hillside Avenue and Marm Simonds (City of Medford, Historic District Commission notice (July 2024)) |
Medford Square painting questions
Is my house on Hillside or Grandview Avenue subject to review?
Exterior alterations and repairs visible from a public way go before the Historic District Commission. The city's published notice doesn't say whether a repaint in new colors counts, so ask the commission directly before ordering paint.
Can a stuccoed Craftsman be painted like clapboard?
Not with the same approach. Stucco needs cracks repaired first and a masonry coating chosen for stucco, not a product picked for wood siding. If the stucco has never been painted, consider whether it needs to be.
Are the 1800s houses on Oakland and Ashland streets likely to have lead paint?
Assume so until a test says otherwise. They were built long before 1978, the cutoff EPA uses for its lead-safe work rules, and old trim paint can survive under later coats. Scraping and sanding there should follow the lead-safe rules for Massachusetts.
How much will it cost to paint a house near the Square?
We don't publish price lists. The number depends on the siding material, how much ornate trim there is, and whether the house sits on a slope that needs staging. You can compare Massachusetts market figures in the exterior painting cost guide, then get a free written estimate.
Cost reference for Medford Square projects
Expect Medford work here to land in the mid range of typical Massachusetts contractor market pricing, depending on scope. See the Massachusetts cost reference and interior painting in Medford.
These are not AJ Painting price quotes. Request a written estimate for your home's specific scope.
More Medford neighborhoods
Planning work on a house or unit near Medford Square?
Licensed and insured, with a free on-site visit. See [exterior painting in Medford](/services/exterior-painting-medford-ma/) and [interior painting in Medford](/services/interior-painting-medford-ma/), or call (508) 258-4325.
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