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Chestnut Hill Painters — Heath St to the Reservoir

Brookline's share of Chestnut Hill is a neighborhood of detached houses on lots from a third of an acre to over two acres, many of them architect-designed between the 1880s and the 1920s.

About the neighborhood

The Lee family farm turned architects' showcase

Francis Lee gave Chestnut Hill its name and built its first country house in the 1850s on land his uncle Joseph Lee had farmed. Beacon Street reached Newton Centre in 1850–51 and rail service followed in 1852, but suburban house building in what is now the Chestnut Hill North district began in 1886–87 and, with limited exceptions, was done before 1929.

The Brookline Historical Commission's 1983 survey describes single-family houses on lots from a third of an acre to more than two acres. Queen Anne houses appear on Boylston Street, Alwyngton Road and Crafts Road; Medieval Revival on Norfolk Road and Heath Street; Colonial Revival, mostly early 1900s, on Crafts and Middlesex Roads. Shingle Style predominates, with examples on Circuit, Dunster and Devon Roads. The firm of Chapman and Frazer designed at least 29 of the 127 buildings surveyed, and Horace Frazer, a partner in that firm, built his own home at Heath and Boylston Streets.

The 1983 survey credited the area's intact appearance to a stable neighborhood, careful upkeep and few visible alterations. Current census figures point the same way: in Tract 4011, which includes addresses on Heath Street and on Spooner, Crafts and Circuit Roads, 64% of homes are detached houses, three-quarters are owner-occupied and close to 60% were built before 1940.

What makes Chestnut Hill projects distinct

Chestnut Hill North review

Town Meeting approved the Chestnut Hill North Local Historic District in 2005, covering 112 properties between Boylston Street and the Green Line, built mostly from 1880 to 1920. Inside it, most exterior modifications go through the Preservation Commission, and the application should be filed before the job is scheduled. Whether color alone is reviewed is a question for Preservation staff; get their answer in writing before ordering paint.

Shingle walls and their finish

Shingle Style houses carry large wall areas of wood shingle. Whether they get stain or paint depends on what is on them now: a coat of paint seals the wood, so stain will not penetrate until it is removed. The survey found clapboard and shingle the most common cladding and few houses with artificial siding, so most of the wall surface on these houses is wood.

Arts and Crafts stucco

Brick and stucco became popular for houses built here between 1910 and 1930, and the survey notes Arts and Crafts influence on Middlesex, Spooner and Reservoir Roads; the firm of Putnam and Cox alone designed at least seven homes, some of them stucco. Stucco needs cracks repaired and a breathable masonry coating, not the exterior latex used on the wood trim beside it.

Big lots, tall trees

Linda Olson Pehlke’s neighborhood history for the Brookline Historical Society says these houses were carefully sited on large lots that were heavily wooded. Where that cover remains, shade slows drying on north walls, so wash-down for mildew and checks of sills and lower shingle courses belong in the scope, and protecting plantings is part of setting ladders and staging.

Chestnut Hill at a glance

Chestnut Hill North Local Historic DistrictApproved by Town Meeting 2005; 112 properties, built mainly 1880–1920 (Linda Olson Pehlke, 'Chestnut Hill,' Brookline Historical Society)
Architect-designed housesChapman and Frazer: at least 29 of 127 buildings surveyed (1983) (MHC Area Form / NRHP nomination, Chestnut Hill Historic District, Brookline (#85003253))
Single-family detached (Census Tract 4011)63.8% of units; 73.8% owner-occupied (U.S. Census ACS 2020–2024 5-year, tables B25024/B25003)
Built before 1980 (Census Tract 4011)81.2% of units; 59.6% built 1939 or earlier; median year 1938 (U.S. Census ACS 2020–2024 5-year, tables B25034/B25035)

Chestnut Hill painting questions

Is every Chestnut Hill house in Brookline inside the local district?

Not necessarily. The local district is bounded by Boylston Street and the Green Line, and the 1983 survey behind the National Register listing left out a section north of Boylston that was developed in the late 1930s and 1940s on former Chestnut Hill Club land. Brookline Preservation staff can tell you which applies to your lot.

How long does Preservation Commission review take?

The Commission meets once a month, with a noon filing deadline roughly three weeks earlier. A Certificate of Appropriateness costs $2 per $1,000 of estimated work with a $50 minimum, and applying after work starts triples it, so file first.

Do I need lead-safe work on interior trim?

With about 81% of homes in Tract 4011 built before 1980, original woodwork and plaster may carry lead under newer coats. Disturbing more than 6 square feet per room triggers certified lead-safe practices; our lead-safe page explains the steps.

How can I budget for a house this size?

We give written estimates after a free on-site visit rather than published rates. The Brookline painting cost guide summarizes Massachusetts market figures to help you set a range.

Cost reference for Chestnut Hill projects

Pricing here tends toward the upper third of typical Massachusetts market data, based on the home and prep depth. See the Massachusetts cost reference and interior painting in Brookline.

These are not AJ Painting price quotes. Request a written estimate for your home's specific scope.

Schedule a Chestnut Hill walk-through

Licensed, insured and rated 5.0 on Google by 30 reviewers, AJ Painting visits for free and leaves a written estimate. Read about [exterior](/services/exterior-painting-brookline-ma/), [interior](/services/interior-painting-brookline-ma/) or [cabinet](/services/cabinet-painting-brookline-ma/) painting, or call (508) 258-4325 Mon–Sat, 7AM–6PM.

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