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Business Details
28 Years
experience
Your Trusted Berkshire County Real Estate Partner
Founded in 1998, Steepleview Realty has established itself as a progressive leader in Berkshire County and Southern Vermont real estate. Our team of native professionals combines decades of local expertise with cutting-edge technology to deliver exceptional results for buyers and sellers. Recognized by the Massachusetts Association of Realtors, we leverage direct MLS integration and a fully computerized system to provide real-time market data.

Our brokers personally select agents renowned for closing complex transactions, including properties previously stalled with other firms. With offices across four states and specialized training programs through the Gateway School of Real Estate, we maintain a reputation for getting the job done where others cannot.
Services
Residential Sales Commercial Sales Investment Properties Land Sales Multi-Family Units Property Management VA Loan Assistance Real Estate Training
Details
  • Year established: 1998
Highlights and features
  • We have 38 years of combined leadership experience in Berkshire County real estate
  • Our team uses exclusive technology to access real-time MLS data nationwide
  • We specialize in closing difficult transactions previously stalled with other firms
  • Our brokers personally select top-performing agents for every client engagement
  • We offer in-house real estate education through our licensed Gateway School of Real Estate
What people say
Exceptional professionalism Market expertise unmatched Complex deals handled smoothly Dedicated support through process Perfect home matches achieved
Services
Residential Sales
Our specialized residential sales team helps first-time buyers and seasoned investors navigate the Berkshire County housing market. With deep local knowledge and advanced MLS access, we identify perfect matches for client needs while negotiating optimal terms. Our agents' average 25+ years of experience ensures smooth transactions through every market condition.
Commercial Sales
We facilitate commercial property transactions for investors and business owners across four states. Our brokers leverage extensive networks and market analysis tools to price properties accurately and attract qualified buyers. From initial evaluation to closing, our expert team manages complex deals with efficiency and transparency.
Investment Properties
Our investment specialists guide clients in building profitable real estate portfolios. With expertise in multi-family units and income-producing properties, we identify opportunities with strong ROI potential. We provide market analysis, financing guidance, and property management connections to maximize investment value.
Property Management
We offer comprehensive property management solutions for landlords seeking reliable tenant placement and maintenance oversight. Our services include rent collection, vendor coordination, and property inspections. Licensed brokers oversee operations to ensure regulatory compliance and tenant satisfaction while maximizing property value.
Real Estate Training
The Gateway School of Real Estate provides state-approved licensing courses and continuing education for aspiring agents. With locations in Massachusetts and Florida, our owner-instructor delivers hands-on training combining 38 years of industry experience. We prepare students for success through practical applications and real-world transaction scenarios.
People
Jennifer G. Segala
Broker-Owner
With 38 years in real estate, Jennifer founded Steepleview Realty in 1998 and established Gateway School of Real Estate. Holding licenses in four states, she combines academic marketing expertise with practical transaction experience to lead Berkshire County's top-performing agents.
Deb Trzcinski
Broker-Owner
A Berkshire native with 30 years of real estate experience, Deb specializes in residential and investment sales. Her background managing rental properties informs her practical approach to client solutions. Licensed in Massachusetts and Vermont, she became a partner in 2015 after decades of market expertise.
Pauline Green
Broker Associate
Certified Buyer's Representative with 25+ years serving Berkshire County. Specializing in first-time homebuyers and new construction, she's a multi-million dollar seller known for compassionate representation. Her real estate career spans three decades of successful client relationships.
Ruth Goyette
Broker Associate
Veteran real estate professional with 25+ years of experience supporting military families. As VA loan expert, she guides veterans through specialized financing programs. Combines educational background with community service to deliver personalized client solutions for local and national clients.
Christine Girard
Broker Associate
Licensed in three states with expertise in residential and multifamily sales. Former financial services professional offers mortgage market insights to first-time buyers and downsizers. Combines MCLA marketing degree with hands-on experience to create client-centric transaction strategies.
Questions
What areas does Steepleview Realty serve?
We operate across Berkshire County, Massachusetts, Southern Vermont, and have licensed agents available in New York and Florida markets.
Do you specialize in specific property types?
We handle residential, commercial, multi-family, land, and investment properties with specialized expertise in Berkshire County's unique market conditions.
Do you assist military veterans with home purchases?
Yes, our team includes specialists with VA loan expertise who provide dedicated support for veterans and active military members.
What training programs do you offer?
Gateway School of Real Estate provides state-approved licensing courses and continuing education through our Massachusetts and Florida locations.
How do you handle difficult real estate transactions?
Our brokers personally select experienced agents who've successfully closed properties previously stalled with other firms using targeted marketing strategies.
Where are your office locations?
We have offices in Adams and North Adams, Massachusetts, with licensed professionals serving multiple states across the Northeast region.