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Brookline homeowners are facing a meaningful increase in their 2026 property-tax bills, with the median single-family home expected to rise about 6%. In a town where the average bill already exceeds $20,000, even modest percentage changes translate into significant dollar amounts.

Massachusetts is introducing a new tax withholding requirement that will reshape how many high-end real estate closings are handled—especially in Brookline, where million-dollar sales and non-resident owners are the norm. Beginning November 1, 2025, any $1M+ sale involving an out-of-state or international seller will require a portion of the proceeds to be withheld at closing and sent directly to the Department of Revenue. It’s not a new tax, but it does change the timing dramatically, and in a market with a globally diverse ownership base, this rule will surface often. Understanding how the withholding works, who it applies to, and how it affects your net proceeds has become an essential part of preparing for a Brookline sale in 2025 and beyond.

A sweeping new home inspection law taking effect October 15, 2025, will dramatically reshape the home-buying process across Massachusetts. Enacted as part of the 2024 Affordable Homes Act, the regulation ensures that every buyer has the right to a professional home inspection before purchasing a residential property — and makes it illegal for sellers or agents to pressure buyers into waiving that right.

The change comes after years of record competition in the housing market, when “no-inspection” offers became common as buyers sought to gain an edge in bidding wars. State officials say the new rules are designed to restore fairness, transparency, and consumer protection in real estate transactions.

Brookline once again tops Niche’s 2025–2026 rankings as the #1 public school district in Greater Boston — and it’s easy to see why. As both a local agent and parent of four in the Brookline Public Schools, I see every day how exceptional teachers, diverse programs, and a supportive community make this an extraordinary place to raise a family.

That same excellence drives Brookline’s real estate market, where single-family homes now average $3.13M and condos $1.21M, with homes selling in just over a month. Strong schools continue to anchor home values, attract long-term residents, and define Brookline as one of Massachusetts’ most sought-after towns to live, learn, and grow.

In just over a decade Compass has evolved from a single Manhattan office into the nation’s No. 1 residential brokerage, expanding coast-to-coast through more than twenty strategic acquisitions—including Pacific Union, Alain Pinel, and @properties/Christie’s—that added thousands of top agents and tens of billions in annual sales volume. Backed by over $1.5 billion in venture funding and a 2021 IPO, the company blended a technology-first platform with an agent-centric culture to redefine how homes are bought and sold. That relentless growth now culminates in Compass’s planned $1.6 billion merger with Anywhere Real Estate, a move that will unite over 340,000 professionals and position Compass to shape the next era of residential real estate.

When U.S. News & World Report released its latest “Best Places to Live for Quality of Life” rankings, Brookline, Massachusetts, claimed the #1 spot in the entire country. For residents, this comes as welcome validation of what they experience daily: a town where excellent schools, cultural vitality, and walkable streets create a lifestyle that consistently outshines national peers. For homebuyers and sellers, the ranking adds another layer of urgency to an already competitive housing market.

Brookline’s affordable housing share has slipped below the state’s 10% threshold, giving developers new leverage under Chapter 40B. “We’re likely going to get three or four, maybe even six, new 40B applications this fall,” warned Planning Director Kara Brewton. Already, Oak Hill has revived its six-story plan at 429 Harvard Street, a 103-unit Chestnut Hill project is tied up in court, and City Realty has floated a massive Route 9 40B if commercial talks stall. With local control weakened, Brookline’s development battles are shifting from zoning boards to the state—and, in some cases, to the courts.

Brookline’s inclusion among the top 50 safest and wealthiest communities in the U.S. validates what residents already know — this is one of the most desirable places to live in the country.

A seismic shift is coming to the Massachusetts rental market. On August 1, 2025, a new law, championed by Governor Maura Healey, will fundamentally change how real estate brokers are paid. The long-standing practice of tenants paying the fee for the landlord’s agent will end. The new rule is simple: whoever hires the agent, pays the agent.

For a high-cost market like Brookline, where renters already face immense financial pressure, this change is monumental. This definitive guide deconstructs the new legislation, offering a strategic playbook for listing agents, tenant representatives, landlords, and renters. We’ll explore the critical compliance deadlines, the new “rules of the road” for representation, and the likely market impacts, from rising rents to the end of “co-broking” as we know it. This is your essential resource for navigating the new era of renting in Massachusetts.

Beginning September 2, 2025, Massachusetts landlords will be subject to new regulations requiring full transparency in rental pricing. Under the state’s expanded consumer protection rules, all advertised rents must clearly disclose the “Total Price” a tenant will pay—including all mandatory fees and charges—before collecting any personal information. While originally designed to curb hidden fees in hotel and ticketing industries, the rules explicitly apply to rental housing. Brookline landlords should review their advertising and lease practices now to ensure compliance and avoid potential penalties under Chapter 93A.