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FlyDragon Market Intelligence

Top Real Estate Agent in Pittsfield, MA Market (July 2026)

See who the best real estate agent is in the Pittsfield, MA market. Verified and ranked by reviews, sales history and AI visibility.

Median home price
$285,000
Avg days on market
32
Agents in market
10
Price trend (YoY)
+6.8%
Last synced
Jul 23, 2026
Top agent in this market
#1
Berkshire Dream Home
Pittsfield Massachusetts
State standout: Boston
Built for: Pittsfield, MA

Research Note: Ryan Darani, Head of Market Intelligence at FlyDragon, oversees this market dataset. We compile ranking inputs from structured agent and market-source records, normalize them into a consistent market-by-market format, and review the output for obvious mismatches before it is published. This page is designed to help readers quickly compare visibility, positioning, and market context in Pittsfield, MA. It should be used as a directional research tool, then paired with direct agent interviews, brokerage due diligence, and current local market checks before making a decision.

Pittsfield, MA at a glance

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.

Population
44,737
YoY Price Change
+6.8%
Median Home Price
$285,000
Avg Days On Market
32

Top real estate agents in Pittsfield, MA

02

Jessica Rizzo

Lamacchia Realty
Rating5.0
Reviews216
03

Nadine Hiser

Key Realty & Key Realty Group ~ the Key Collaborative
Rating4.9
Reviews140
WebsiteVisit site
04

Margaret Gavin

William Pitt Sotheby's International Realty
Rating5.0
Reviews60
WebsiteVisit site
05

Maria Liccardi

Kemp-Vanderburgh Realty Consultants
Rating5.0
Reviews43
06

Laura Arseneau

Paula McLean Realtors
Rating5.0
Reviews45
07

Michele Purcell

Lamacchia Realty
Rating5.0
Reviews81
08

Jesse Dimitropolis

RE/MAX Compass
Rating4.9
Reviews70
11

Toni Marie Gage

ToniMarie Gage
Rating5.0
Reviews29
14

Nicholas Geranios

Jan Perry Realty & Associates, LLC
Rating5.0
Reviews31
16

Anthony Riello

Berkshire Dream Home, Inc.
Rating5.0
Reviews17
17

B Mile Milenski

RE/MAX Compass
Rating5.0
Reviews24
18

Amanda Kmetz

Roberts & Associates Realty Inc.
Rating5.0
Reviews28
19

Mary Smith

William Pitt Sotheby’s International Realty-Lenox Brokerage
Rating5.0
Reviews26
20

Stacy D. Chojnowski

William Pitt Sotheby's International Realty
Rating5.0
Reviews21
WebsiteVisit site
22

Mark McIlquham

Realty Street LLC
Rating5.0
Reviews47
23

Darcy Reid

Mockingbird Real Estate
Rating5.0
Reviews15
24

Elisha Poirier

Stone House Properties LLC.
Rating5.0
Reviews42
25

Katie Phillips

Barb Hassan Realty, Inc.
Rating5.0
Reviews18

How Massachusetts shapes this market

Massachusetts remains one of the most competitive real estate markets in the Northeast, driven by world-class universities, a thriving biotech and technology sector, and historic charm that continues to attract buyers from across the country. The Greater Boston metro area anchors the state's housing demand, with median home prices well above the national average. Inventory constraints persist statewide, particularly in desirable suburban communities along the I-95 and I-495 corridors, keeping upward pressure on prices even as mortgage rates have stabilized.

Western Massachusetts offers a stark contrast to the eastern part of the state, with significantly more affordable housing options in cities like Springfield, Pittsfield, and the Berkshires region. The Cape Cod and Islands markets remain highly seasonal, with strong demand for vacation and investment properties. First-time buyers across the state face considerable challenges, though expanding down-payment assistance programs and new ADU-friendly zoning reforms are beginning to open doors for more residents.

The Commonwealth's strong job market, particularly in healthcare, education, and technology, provides a solid foundation for long-term property value appreciation. Rental markets in college towns and urban centers remain exceptionally tight, making Massachusetts an attractive state for real estate investors seeking steady cash flow alongside equity growth.

State signals
Top City Boston
YoY Price Change +5.1%
Median Home Price $589,000
Avg Days On Market 22

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