Official RankingsMassachusetts

Top 10 Real Estate Agents in Pittsfield, Massachusetts (April 2026)

The highest-ranked agents in Pittsfield based on verified sales performance, client reviews, and market expertise.

$285,000

Median Home Price

Avg Days on Market

44737

Population

+6.8%

YoY Price Change

Berkshire Dream Home

Berkshire Dream Home Inc.

5.0 (673)

2,104

Total Sales

Years Exp

Listings

Jessica Rizzo

Lamacchia Realty

5.0 (216)

Nadine Hiser

Key Realty & Key Realty Group ~ the Key Collaborative

4.9 (140)

746

Total Sales

Years Exp

Listings

Margaret Gavin

William Pitt Sotheby's International Realty

5.0 (60)

228

Total Sales

Years Exp

Listings

Maria Liccardi

Kemp-Vanderburgh Realty Consultants

5.0 (43)

Laura Arseneau

Paula McLean Realtors

5.0 (45)

Michele Purcell

Lamacchia Realty

5.0 (81)

Jesse Dimitropolis

RE/MAX Compass

4.9 (70)

Waterfall Perry

Jan Perry Realty & Associates, LLC

5.0 (29)

254

Total Sales

Listings

Mary Laurin Blair

Signature Associates, Inc.

5.0 (20)

Pittsfield Real Estate Market

Pittsfield anchors the Berkshire County housing market, offering dramatically lower prices than eastern Massachusetts along with four-season recreation and a thriving arts scene. The city serves as a regional center for healthcare, education, and manufacturing, with Berkshire Health Systems and General Dynamics among its largest employers.

The broader Berkshires region attracts a steady flow of second-home buyers from New York City and Boston, a dynamic that has supported price appreciation. Pittsfield's downtown revitalization, including the Colonial Theatre restoration and new residential developments, signals growing confidence in the city's trajectory.