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Test-Driving Homes with Sleepovers: A New Trend Reaches Connecticut

September 2, 2025 | Luxury Housing Trends | Presented by ReadySetLoan™️


Luxury buyers are rethinking how they shop for real estate. Across the country—and now making its way into Connecticut’s luxury housing market—a new trend is taking hold: overnight stays in homes before purchase.

From Greenwich to Westport, buyers are asking for a more immersive experience, requesting the chance to “live in” a property before signing a contract. Whether it’s a $5 million waterfront estate or a countryside retreat, the idea is the same: test-driving a home overnight gives clarity no staged showing can match.


Why This Matters in Connecticut

  • Buyers: In high-end markets like Fairfield County and the Shoreline, a sleepover can reveal critical details—traffic noise, natural light, neighborhood vibe—that influence a decision.

  • Sellers: For those marketing luxury properties, offering this experience can demonstrate confidence and help a serious buyer commit.


Neil’s Take 🎤

"Luxury buyers in Connecticut are discerning. A home isn’t just an investment—it’s a lifestyle decision. Allowing a buyer to spend the night in a property offers an emotional connection that no brochure can deliver. Pair that with a smart financing plan, and confidence follows.”— Neil Caron, Area Sales Manager, CMG Mortgage


🐷 RSL Piggy Points

  • Luxury buyers want more: CT’s affluent buyers seek experiences, not just listings.

  • Seller strategy: A test-drive approach could shorten days on market for high-value homes.

  • Confidence drives contracts: Emotional clarity leads to smoother closings.

  • Mortgage readiness matters: The right financing ensures buyers can act quickly when the fit is right.


RSL Perspective

At ReadySetLoan™️, we see Connecticut’s luxury market as a balance of numbers and nuance. While the “sleepover trend” might be most visible at the $5 million level and up, the takeaway applies at all price points: informed buyers make confident decisions. And confident decisions are where great mortgages begin.


🏁 Final Lap

The luxury sleepover trend is a glimpse into the future of Connecticut real estate. Buyers want to know exactly what they’re getting—and sellers who adapt may hold the advantage. At ReadySetLoan™️, our role is to bring you that same clarity on the mortgage side—so when the perfect property appears, you can rest easy knowing you’re ready.





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