CT Real Estate Edge Podcast

When you're buying or selling a home in towns like Trumbull, Monroe, Fairfield, or Shelton, local knowledge makes all the difference. In this episode of the CT Real Estate Edge Podcast, Rob Weinberg sits down with Kimberly Levinson, a licensed Realtor since 2005 and lifelong resident of the Trumbull and Monroe area, to talk about what it really takes to navigate the Greater Bridgeport real estate market.
Kimberly has spent nearly two decades building a reputation around relationships, not transactions. She's been named REALTOR of the Year by the Greater Bridgeport Board of REALTORS, recognized as a Five Star Agent for four consecutive years, and has taught continuing education courses to fellow agents since 2013. She serves buyers and sellers across Monroe, Trumbull, Easton, Huntington, Stratford, Shelton, Milford, Fairfield, and Newtown, with expertise spanning residential resales, condos, new construction, and land sales.
Rob and Kimberly talk about what's actually happening in the greater Fairfield market right now, how she approaches every client like they're her only client, and what buyers and sellers in this part of Connecticut should know before making their next move. If you're navigating real estate in this corner of the state, this episode is worth your time.
Connect with Kimberly Levinson: kimberlybraunlevinson.com

Connecticut or New York — which state is the right move for your next home?
In this episode of the CT Real Estate Edge Podcast, Rob Weinberg sits down with Carly Heneghan, a licensed realtor in both Connecticut and New York, to break down everything buyers need to know before choosing between these two neighboring real estate markets.
Whether you're priced out of New York, relocating from the city, or simply weighing your options across state lines, this conversation gives you the honest, on-the-ground perspective that only a realtor who actively works both markets can provide. Carly brings clarity to many of the most common questions buyers are asking right now.

Fairfield County real estate moves fast, and the people who understand it best are the ones who have lived it from every angle. In this episode of the CT Real Estate Edge Podcast, Rob Weinberg sits down with Barb Hazelton, Branch Manager for Coldwell Banker's offices in Fairfield County, where she leads almost 250 agents across two of the most active markets in Connecticut. With 14 years of her own production experience behind her and a career that began well outside of real estate, Barb brings a grounded, no-nonsense perspective on what is actually happening in the market right now.
Rob and Barb cover what buyers and sellers need to know to compete in Fairfield County today, how the role of a great agent has evolved, and what strong brokerage leadership looks like in a market this demanding. Barb also draws on her deep community roots and her service on the Darien Zoning Board of Appeals to paint a picture of a real estate professional who is as invested in people as she is in production.
If you are buying, selling, or building a real estate career in Fairfield County, this conversation belongs in your playlist.

Selling a home in Greenwich, Connecticut is not like selling anywhere else. The buyers are sophisticated, the stakes are high, and the margin for error is zero. In this episode of the CT Real Estate Edge Podcast, Rob Weinberg sits down with Jennifer Leahy, one of the most accomplished luxury real estate agents in the country, to talk about what it actually takes to move high-end properties in Fairfield County and beyond.
Jennifer leads the Jennifer Leahy Team at Compass, consistently ranked the number one team in Connecticut by Real Trends. With over $1.25 billion in career sales and a client list that spans some of the most discerning buyers and sellers in the tri-state area, Jennifer offers a perspective on the luxury market that is rare, candid, and deeply practical. 
This conversation goes beyond the price tags. Jennifer and Rob dig into the psychology of the ultra-luxury transaction, the marketing strategies that actually move eight and nine-figure properties, and why selling at the top of the market demands a completely different playbook.
If you are thinking about buying or selling at the upper end of the Connecticut market, this is the episode that will change how you think about the process.
Connect with Jennifer on Instagram : @jenniferleahyhomes

What does it take to build a real estate career spanning 40 years, over 500 transactions, and more than a billion dollars in sales? In this episode of the CT Real Estate Edge Podcast, host Rob Weinberg sits down with Russell Pruner, one of Greenwich, Connecticut's most respected and decorated real estate brokers.
Russell has been navigating the Greenwich market since 1985, and in this conversation he pulls back the curtain on what it really takes to buy, sell, and succeed in one of the most competitive luxury real estate markets in the country. Whether you're a first-time buyer eyeing Cos Cob or Riverside, a homeowner thinking about downsizing, or a seller looking to position a luxury property in back-country Greenwich for maximum return, this episode is packed with insight you won't find anywhere else.
Russell is a six-time President of the Greenwich Association of REALTORS, Greenwich REALTOR of the Year, a Certified Residential Specialist (CRS), Senior Real Estate Specialist (SRES), and a current member of the Greenwich Streets Team at Compass. His approach is simple: every decision grounded in data, every client treated with honesty and care.
If you're buying or selling in Greenwich, CT, this is the episode to listen to before you make your next move.
Connect with Russell Pruner: greenwichstreets.com

What if there was a real estate strategy generating $40K to $75K per deal — in about four months — that most investors have completely ignored?
In this episode of the CT Real Estate Edge Podcast, Rob Weinberg sits down with Chris Gavre, a real estate investor who built a portfolio of nearly 150 rental units by age 25 before pivoting to one of the most underrated plays in today's market: land-home packages.
Chris breaks down exactly how his land-home investing model works, why affordable housing demand is fueling its growth, and how he scaled to 50 deals per year with the right systems in place.
Whether you're a seasoned investor looking for a better ROI strategy or someone just getting started in real estate, this conversation will open your eyes to an opportunity hiding in plain sight.

In this episode of Connecticut Real Estate Edge, Rob Weinberg breaks down the biggest mistakes homebuyers make when choosing a realtor or mortgage lender and how these decisions can impact your finances far beyond the closing table.
Many buyers focus on interest rates and home prices, but overlook the importance of working with the right professionals. Rob explains why choosing based on convenience, chasing the lowest rate, and failing to ask the right questions can lead to costly outcomes.
Whether you’re a first-time homebuyer or planning your next real estate move, this episode will help you make smarter decisions and avoid costly pitfalls.

In this episode, Rob breaks down why building the right real estate wealth team is one of the most overlooked keys to long-term financial success. While many people think wealth in real estate is just about finding the perfect property, Rob explains why the people around you often matter even more than the deal itself.
Drawing from his experience helping thousands of homeowners and investors navigate the mortgage and home buying process, Rob walks through the key professionals that make up a team including real estate agents, lenders, attorneys, inspectors, and financial advisors. He also explains the different phases of the wealth team, incorporating future growth and deeper discussions with syndicators, developers, and real estate entrepreneurs.
Whether you’re buying your first home, building an investment portfolio, or simply trying to make smarter financial decisions around real estate, this episode will help you understand how the right team can protect you from costly mistakes and open doors to bigger opportunities.

In this episode, Rob sits down with billionaire real estate developer and investor Ari Rastegar, CEO of Rastegar Property Company, to unpack how failure, discipline, and resilience became the foundation of his real estate empire.
Ari shares his journey from investing during law school to developing projects across 38 cities and 13 states, and why some of his toughest setbacks became his greatest teachers. They dive into what it really takes to scale in today’s market, how to build durable wealth beyond short-term wins, and why transparency and discipline are the ultimate unfair advantages in real estate.
Whether you’re an investor, entrepreneur, or real estate professional, this episode delivers powerful mindset shifts and real-world strategies for building lasting success through adversity.
Connect with Ari: www.RastegarCapital.com or www.RastegarInvest.com 

In this episode of Connecticut Real Estate Edge, Rob Weinberg sits down with legendary real estate investor and educator Rod Khleif, host of the Lifetime Cash Flow Through Real Estate podcast and mentor to thousands of investors worldwide.
Rod shares the powerful story of losing over $50 million during the 2008 crash and how that experience reshaped his mindset, investing strategy, and approach to building lasting wealth. Together, Rob and Rod break down why today’s market represents one of the largest wealth transfer opportunities in real estate, how multifamily investing outperforms single-family long term, and the due diligence mistakes that can wipe out even experienced investors.
Whether you’re a new investor, seasoned real estate professional, or someone looking to create long-term cash flow through smart property investing, this conversation delivers real-world frameworks and hard-earned lessons you can apply immediately.
Connect with Rod: https://rodkhleif.com/ and https://rodslinks.com