If you own a vacation or investment property along the South Strand, the window from late fall through early spring offers an opportunity that many owners underestimate.
While summer feels busy and active, this quieter season is often when the most strategic resort property transactions take place. Buyers are focused, homes are easier to show, and purchases can be timed perfectly for the upcoming rental season.
This time of year isn’t slow — it’s smart.
Easier Access Creates Better Opportunities
One of the biggest advantages of selling a resort property during the off-season is simple: access.
Without weekly renters, tight turnovers, and packed summer schedules, buyers can tour homes more easily and spend real time evaluating the property. They’re able to walk through thoughtfully, ask the right questions, and consider how the home works both as a personal retreat and an investment.
That level of access leads to more confident — and more serious — buyers.
Buyers Are Planning Ahead, Not Waiting
Resort buyers who purchase during this season aren’t behind the curve — they’re ahead of it.
Buying now allows time to:
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Understand ownership and operating costs
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Review insurance and HOA considerations
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Evaluate rental performance and income potential
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Make updates or improvements before peak season
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Be fully positioned for the upcoming vacation months
For many buyers, purchasing during this window is part of a long-term plan, not an impulse decision.
Real-World Examples From This Season
573 S Dunes Drive | Charlestowne Grant, Litchfield by the Sea
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This premier property sale was part of a 1031 exchange, requiring precise timing and careful coordination. We represented both the buyer and the seller, which allowed for clear communication, efficient decision-making, and a smooth closing within a tight timeframe. The result was a successful exchange for the seller and a confident purchase for the buyer.
316 Cypress Avenue | Garden City | NEW THE THE MARKET | $1,150,000
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Now new to the market, this Garden City property is a great example of why this time of year is so effective for resort sales. Without rental interruptions, buyers can easily tour the home, review details, and evaluate the investment opportunity with clarity — all while positioning themselves for the upcoming vacation season.
This is exactly when motivated resort buyers are paying attention.
Properties introduced during this window benefit from access, focus, and timing — three things that are often harder to achieve during peak rental months.
Resort Properties Aren’t Marketed Like Primary Homes
Selling a resort or investment property requires a different approach.
Buyers aren’t just looking at floor plans and finishes — they want clarity on the full picture:
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What does it cost to own?
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What does insurance look like?
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How does the property perform as a rental?
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What does a realistic return on investment look like?
Answering these questions upfront builds confidence and keeps the focus where it belongs — on the opportunity, not the unknowns.
A Simple Way Buyers Think About ROI
When buyers evaluate a resort property, they’re rarely looking for guarantees. Instead, they want clear, realistic expectations.
Most start with three foundational questions:
What will it cost to own?
This includes insurance, HOA dues, property taxes, utilities, and routine maintenance. Understanding true ownership costs allows buyers to plan responsibly.
What could it realistically earn?
Rental income varies by location, season, and property type. Buyers want comparisons to similar properties and honest insight — not best-case scenarios.
How does lifestyle factor in?
Many buyers value the ability to enjoy the property themselves during quieter months while allowing it to generate income during peak vacation season. For many, that lifestyle flexibility is part of the return.
ROI isn’t just about numbers on a spreadsheet — it’s about how the property fits into a broader financial and lifestyle plan.
A Great Example of Balance: 30 Spartina Court | $615,000
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This updated Heron Marsh property in Litchfield by the Sea is a great example of how resort properties can truly work double duty.
The owners enjoy the home during the off-season, taking advantage of the relaxed pace and quieter surroundings. During the traditional vacation months, the property transitions into a rental, benefiting from strong demand and its desirable location.
Used personally when it makes sense. Rented when demand is strongest.
That flexibility is exactly what many of today’s resort buyers are looking for.
Thinking About Selling?
If you’re considering selling your resort property in 2025 or beyond, now is the time to start the conversation — even if your plans are still forming.
The right preparation, pricing, and strategy — paired with the right season — can make a meaningful difference in timing and outcome.
If you’d like to talk through your options or better understand what buyers are looking for right now, we’re always happy to help.
Mariah Johnson & Hampton Roberts
Local. Proven. Resort Property Specialists.