The Legit Real Estate Podcast

🤖 Is AI changing real estate forever—or putting jobs at risk? Welcome to Episode 68 of the Legit Real Estate Podcast with Holly Regoli and TJ Regoli! This week, we're exploring how artificial intelligence is transforming the way real estate professionals work across Rhode Island, Massachusetts, and Connecticut. Holly shares real examples of using AI to research commercial properties, review p...

Why can a listing get views, saves, likes, and even open-house traffic — but still generate almost no calls or serious offers? In Episode 67, Holly and Tj get into the realities of today’s real estate market, including a listing that’s getting online attention but surprisingly little buyer action. They also talk about:🏗️ New construction vs. buying an existing homeWhat really goes into building a...

What happens when a Realtor sends the wrong text to the wrong person? 😳In Episode 66 of the Legit Real Estate Podcast, Holly Regoli and TJ Ciolfi share hilarious—and sometimes potentially costly—real estate texting mistakes, autocorrect disasters, and stories from behind the scenes of working with buyers and sellers. They also tackle a frustrating question every seller and agent eventually faces:...

Real estate never stops—even when the AC breaks, tenants need help, contractors are hard to find, and renovation costs keep climbing. In Episode 65 of the Legit Real Estate Podcast, Holly and TJ talk about the realities of landlord life, why reliable contractors are worth keeping, lessons from a real estate partnership that made almost no profit, and the surprising cost of owning property on Block...

Would you rather deal with a seller who refuses to leave during showings… or a buyer who brings the entire family along? In Episode 64 of the Legit Real Estate Podcast, we play Would You Rather: Real Estate Edition and get into some of the funniest, strangest, and most frustrating situations real estate professionals can face. From nightmare showings and unrealistic buyers to overpriced listings,...

In Episode 62 of the Legit Real Estate Podcast, Holly Regoli and TJ Ciolfi discuss what they're seeing in today's Rhode Island, Connecticut, and Massachusetts real estate market. Topics include: ✅ Why overpriced homes struggle to attract buyers ✅ Why price reductions don't always generate new interest ✅ Current open house traffic trends ✅ How Zillow estimates compare to professiona...

Buying or selling a home in Rhode Island, Connecticut, or Massachusetts? This episode is packed with real-life experiences every homeowner should hear. In Episode 61 of the Legit Real Estate Podcast, Holly Regoli and TJ Ciolfi share behind-the-scenes stories from real estate transactions, including:✅ Why homes must be completely empty before closing✅ Common seller mistakes that delay closings✅...

Thinking about buying or owning a home in Connecticut, Rhode Island, or Massachusetts? In Episode 60 of The Legit Real Estate Podcast, Holly Regoli and T.J. discuss hidden homeownership costs that many buyers overlook before closing. In this episode, you'll learn:How Homestead Exemptions can lower your property taxesWhy lenders calculate escrow differently than your actual future paymentCommon...

Thinking about buying or selling a home in Rhode Island, Connecticut, or Massachusetts? Episode 59 of The Legit Real Estate Podcast covers real-world experiences that every homeowner, buyer, seller, and real estate investor should hear. This week, TJ and Holly discuss the challenges of buying new construction homes, why builder delays can create major problems for buyers, and what really happens d...

Buying or selling a home in Rhode Island, Massachusetts, or Connecticut? In Episode 58 of The Legit Real Estate Podcast, TJ and Holly sit down with electrician Alan St. Pierre to discuss electrical inspections, breaker panels, double taps, knob-and-tube wiring, repair costs, and issues that could affect a real estate transaction. The conversation also explores a creative approach to selling homes:...

Welcome to another episode of The Legit Real Estate Podcast! Host TJ Chofi sits down with Holly Regoli to explore the world of real estate—from residential listings to exciting opportunities in commercial properties. Key Highlights from this episode:Transitioning from residential to commercial real estateWhat buyers and sellers should know in today’s market trendsStories of helping clients get the...

In Episode 33 of The Legit Real Estate Podcast, TJ and Holly Regoli kick things off in an unconventional way — with TJ joining the show while driving 80 mph to his next meeting! Between laughs and safety debates (seatbelts included!), the duo dives into stories from the road, lessons from the real estate trenches, and what it really takes to stay productive when life gets hectic. Listen the conver...

A cheap driveway quote sounded like a great deal—until the work was done. In Episode 57, T.J. and Holly discuss contractor expectations, home warranties, plumbing leaks, AC repairs, pool maintenance, affordable housing challenges, and unusual homeownership arrangements where buyers own the house but not the land. If you've ever dealt with unexpected repair costs or questionable workmanship, th...

This week on The Legit Real Estate Podcast, TJ is dealing with every landlord's worst nightmare—a hidden water leak that turned into a major repair project. From damaged walls and aging plumbing to contractor coordination and unexpected expenses, we break down what really happens when property ownership goes sideways. We also discuss real estate lead programs, the importance of reading the fin...

On this episode of the Legit Real Estate Podcast, Holly is joined by Jennifer Dandridge and Erica Fluevog for a hilarious game of TWO TRUTHS & A LIE — Real Estate Edition! From bat houses in Florida and golf cart neighborhoods in Arizona to spite houses, coffin corners, billion-dollar mansions, and bizarre real estate laws… things get weird FAST.Plus:Crazy property storiesHistoric home factsWe...

In Episode 54 of the Legit Real Estate Podcast, Holly and TJ share some of the wildest real estate stories yet — including aggressive French bulldogs during a showing, nightmare listing situations, bizarre seller behavior, and even a dead sheep left on a property. From chaotic walkthroughs to awkward client experiences, this episode dives into the unpredictable side of real estate that agents deal...

In Episode 53 of the Legit Real Estate Podcast, Holly and TJ dive into one of the most stressful real estate closings yet — complete with solar panel complications, moving disasters, storage unit chaos, sewer ejector pump repairs, and buyers requesting petty inspection fixes. They also talk about:Home inspection negotiations gone wrongWhy some buyers ask for ridiculous repairsSolar panel headaches...

In Episode 52 of the Legit Real Estate Podcast, Holly Regoli and TJ dive into the chaos of balancing family life, youth sports, scouting, and the nonstop grind of real estate. This episode covers:The reality of cold real estate leadsWhy buyer agency agreements make agents nervousAI bots and Facebook lead generationScam calls targeting homeowners and familiesParenting moments, teenage driving, and...

This episode is chaos in the best way. We’re talking:A $25,000 deposit sent to the WRONG brokerageAn appraiser missing an entire bathroom (yes… seriously)Why multiple offers don’t always mean appraised valueReal-life realtor struggles from the car, parking lots, and everywhere in betweenAnd a wild story about a husband secretly charging his wife rent on a property HE owns 😳Plus:Should agents brin...

This week on the Legit Real Estate Podcast, things get REAL.A deal is on the line… and an appraisal comes in $20,000 LOW—but that’s just the beginning. From questionable valuation methods to a shocking discovery about who actually showed up at the property, this episode dives into one of the wildest real estate situations we’ve seen. We break down:Why appraisals don’t always reflect realityThe tru...

In Episode 49, Holly sits down with Erica and Jen to break down the real challenges different generations face in today’s housing market—from student debt and rising rates to multi-generational living and fear of buying. They dive into:Why Gen X feels stuckWhy Millennials and Gen Z struggle to enter the marketThe truth about interest rates, equity, and timingWhy your first home isn’t your dream ho...

Episode 47 kicks off with TJ and Holly catching up before diving into a real issue: how solar contracts can complicate a home sale. They break down a current situation, why buyers avoid taking on solar debt, and why sellers should consult their realtor before adding major liens. The episode then shifts into a fun round of Two Truths and a Lie: Real Estate Edition, covering surprising facts like Se...

Episode 48 of the Legit Real Estate Podcast brings a different kind of real estate conversation. Holly is joined by a special guest, her mother, Gladys Arnold, while TJ is away. This episode flips the script from crazy tenant stories to crazy landlord stories. Gladys opens up about the realities of renting through some incredibly difficult situations. She talks about repairing apartments herself,...

Winter hit hard—and this episode is full of real-life homeowner + landlord chaos. TJ and Holly talk snow-covered solar panels, heating costs (electric vs oil vs wood), and why winter bills can be brutal. Then it gets REAL: a sewage backup in an older multifamily, emergency plumbing fees, cast-iron pipe problems, and the messy reality of cleanup. They also get into what tenants (and kids) should NE...

A Rhode Island blizzard shuts everything down — and TJ & Holly break down what that really does to real estate: closings postponed, inspections delayed, open houses canceled, and everyone scrambling to dig out. Then it turns into storytime: the chaos of snow removal as a landlord, propane deliveries during a shutdown, and a final walkthrough situation where buyers reportedly tossed out items t...