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Chestnut Hill Real Estate Market & Neighborhood Guide

The short answer

Chestnut Hill is one Brookline market area, not one interchangeable housing market.

This guide recorded 54 MLS-reported residential closed sales across the 12 complete months shown below: 13 condominiums and 41 single-family homes. Compare property types separately, then verify address-specific building, transit, municipal, and school information before relying on it.

Market interpretation

What changed in the Chestnut Hill market?

Across the 12 complete months ending August 2026, closed sales were down 23.9% year over year. Average sale price was down 4.9% year over year and average price per square foot was up 1.0% year over year.

The latest monthly interpretation is held until its stored Market Report row matches the transaction warehouse.

Compare like with like

Condominiums and houses are separate comparison sets

Property type, building, condition, parking, outdoor space, and association health can materially change the relevant evidence.

MLS-reported closed sales, Sep 2025 – Aug 2026
MeasureCondominiumSingle-family
Closed sales1341
Median sale price$1.28M$2.395M
Average price / sq. ft.$608$745
Median days on market29.020.0
Sold over asking38.5%39.0%

Small segment samples are context, not a standalone pricing model.

Neighborhood due diligence

The market evidence sits inside an address-specific decision.

Chestnut Hill is a useful market-area label, but it does not replace verification for a particular home or building.

01

Housing

The observed sample includes 13 condominium and 41 single-family closings. Building condition, association records, parking, outdoor space, and property condition can materially change the relevant comparison set.

02

Location & access

Confirm the exact route, current transit service, parking rules, and daily travel needs for the address you are considering. A neighborhood name is not a substitute for address-level review.

03

Schools

Neighborhood labels do not determine enrollment. Confirm the exact address and current assignment rules directly with Public Schools of Brookline.

Decision notes

What the evidence changes for buyers and sellers

For sellers

Build the comparison set before the price

Start with comparable sales by property type, size, condition, parking, outdoor space, and building characteristics.

Request a property-specific valuation

For buyers

Separate the home from the building risk

Compare property types separately and verify building, municipal, transit, and school details for the exact address.

Ask a Brookline real-estate question

Understand the evidence

Chestnut Hill market FAQs

What period do the Chestnut Hill market statistics cover?

The current page summarizes Sep 2025 – Aug 2026, with verified data through August 31, 2026. The reporting window advances only after the completed monthly data passes the Market Intelligence validation checks.

How is the Chestnut Hill market area defined?

The page uses the neighborhood classification stored with the MLS-reported residential records in the Bushari Market Intelligence warehouse. It is a market-context area, not a legal, postal, or school-assignment boundary.

Do these neighborhood statistics establish the value of a specific home?

No. The figures describe the included market cohort. A property-specific analysis must also account for property type, size, condition, parking, outdoor space, building characteristics, and current competition.

How should school assignment be checked for a Chestnut Hill address?

Verify the exact address directly with Public Schools of Brookline. Neighborhood names and real-estate market classifications do not determine enrollment.

Property-specific analysis

Apply the Chestnut Hill evidence to one property.

Market Data Methodology

Market statistics on this page are based on MLS-reported residential sales in the Chestnut Hill area for the period Sep 2025 – Aug 2026, including single-family homes and condominiums unless otherwise noted. Data are included only through August 31, 2026; the latest potentially incomplete month is excluded. Private, off-market, and non-MLS transactions may not be included. Neighborhood and school-zone boundaries are approximate and should be used for market context only — not for legal or school-assignment verification. School assignment and buffer-zone status should be verified directly with Public Schools of Brookline.

Year-over-year comparison: Sep 2025 – Aug 2026 (54 closed sales) compared with Sep 2024 – Aug 2025 (71 closed sales). Sale-to-list change is shown in percentage points.

Small-sample disclosure: November 2025 (4 closed sales); January 2026 (4 closed sales); February 2026 (1 closed sale); March 2026 (1 closed sale); July 2026 (4 closed sales); August 2026 (2 closed sales). Monthly averages and medians are calculated from all valid observed transactions. Months with fewer than 5 closings are descriptive only and are excluded from directional conclusions and stable peer comparisons.

Inventory timing: Months of supply as of March 31, 2026. Its YoY comparison uses March 31, 2025. No separate active-inventory count is displayed.

Freshness: Warehouse data last changed September 14, 2026. Equal Housing Opportunity.