Highlights
- A growing number of Santa Teresa property owners are purchasing second and even third properties in the area instead of exiting the market.
- Repeat buyers behave differently than first-time buyers: they focus on strategic expansion, land scarcity, lifestyle optimization, and long-term positioning.
- Many owners now better understand which micro-locations, property types, and infrastructure features matter most after living in or operating their first property.
- Slower market conditions in 2026 are creating opportunities for experienced buyers to negotiate more strategically.
- Some owners are diversifying into land, income-producing villas, neighboring lots, or future family compounds.
- Existing owners often have stronger conviction in Santa Teresa because they’ve experienced the lifestyle and market evolution firsthand.
- The second purchase is usually less emotional and more intentional than the first.
- Long-term owners increasingly view Santa Teresa not just as a vacation destination, but as part of a broader lifestyle and wealth strategy.
- About The Author
A Different Type of Buyer Is Driving the Santa Teresa Market Right Now
For years, Santa Teresa's real estate market was fueled by people discovering the area for the first time. They came for the surf, the tropical lifestyle, the wellness culture, the luxury homes, the incredible jungle and ocean scenery, and the freedom that remote work made possible. That wave of international buyers helped shape the market into what it is today.
But something interesting is happening in 2026.
Many of the buyers actively looking at properties right now are not first time buyers. They already own property here.
And instead of selling, they're buying again.
As a broker, I pay close attention to patterns like this because repeat buyers are one of the strongest indicators of confidence in a market. These are people who already know Santa Teresa. They understand the roads, the seasons, the realities of infrastructure, the rental market, property management challenges, and what day to day life here actually looks like.
They're no longer buying based on a dream. They're buying based on experience.
The difference between a first purchase and a second purchase is significant. The first property is often driven by emotion and discovery. The second is usually much more strategic. The focus shifts from finding a vacation home to optimizing a lifestyle, building a portfolio, creating flexibility for the future, or securing something they now recognize as increasingly scarce.
One thing I hear often from owners is, ''If I knew then what I know now, I would have bought differently.''
That realization frequently leads to another purchase.
There are several reasons why existing owners are expanding their footprint in Santa Teresa.
First, they understand the market better. After owning property here, people learn which areas hold value over time, where guests prefer to stay, how accessibility impacts daily life, where privacy becomes important, and what actually works for long term ownership. Once those lessons are learned, identifying opportunities becomes much easier.
Another major factor is land scarcity. Experienced owners understand that certain types of properties are becoming harder to find. Walkable lots, premium ocean views, usable topography, neighboring parcels, and private land are all finite resources. Buyers who originally focused on finished homes are now increasingly looking at land because they understand its long term value.
Lifestyle changes also play a role. The first property often reflects an aspiration. The second reflects reality. Buyers who initially wanted to be in the center of everything may now be looking for more privacy, larger lots, quieter surroundings, or a property that better suits family life and long term living. As people spend more time in Santa Teresa, their priorities naturally evolve.
For many owners, their first investment simply worked. Their property appreciated, generated rental income, improved their quality of life, and strengthened their connection to the area. Positive experiences tend to create confidence, and confidence often leads to expansion. I'm also seeing more buyers think strategically about building a portfolio rather than owning a single dream property. Some are adding income producing villas, while others are purchasing land for future development, ocean view lots, guest houses, or properties that serve different purposes. This reflects a level of sophistication that wasn't as common several years ago.
Interestingly, slower market cycles often create some of the best buying opportunities for experienced owners. Unlike first time buyers, they are typically less emotional and more patient. They know how to evaluate value, negotiate effectively, and wait for the right opportunity. During quieter periods, buyers often have more time for due diligence, more inventory to choose from, and occasionally better negotiating leverage.
Another important shift is that existing owners view risk differently. They already know what rainy season feels like. They understand maintenance costs, property management, rental demand, and everyday life in Costa Rica. Because of that familiarity, the uncertainty that can hold back first time buyers is greatly reduced.
What we're seeing is part of a larger trend that extends beyond Santa Teresa. People are increasingly thinking about lifestyle assets differently. Instead of asking, ''Where do I want to vacation?'' they're asking, "Where do I want long term roots, flexibility, and lifestyle value?" Santa Teresa continues to fit into that conversation for many buyers.
Some of the most common second purchases I'm seeing today include neighboring lots for additional privacy or future expansion, land banking opportunities, upgraded homes with better views or infrastructure, income producing villas, and larger properties designed for multi generational family use.
Family planning is becoming a bigger factor as well. Buyers who originally purchased for themselves are now thinking about children, aging parents, future retreats, and creating gathering spaces for multiple generations. That often leads them to seek larger parcels, multiple structures, or neighboring properties.
The emotional difference between a first property and a second property is also worth noting. The first purchase is often exciting and aspirational. The second tends to feel more intentional. Buyers become less focused on status and more focused on quality of life, flexibility, long term usability, and legacy.
Many repeat buyers are also prioritizing land over finished homes. They now have a much better understanding of construction quality, design preferences, and future needs. More importantly, they understand scarcity. They recognize that while homes can be built, certain pieces of land can never be recreated.
The buyers who know Santa Teresa best tend to focus on a few key factors. Micro location matters more than ever. Ease of access remains critical. Long term livability becomes a priority. Flexibility is important, whether the property serves as a rental, personal retreat, future family compound, or resale asset. And above all, scarcity matters. Buyers are asking themselves whether a property can realistically be replaced in the future.
To me, one of the most important takeaways from this trend is that confidence remains strong among the people who know Santa Teresa best. These buyers understand both the opportunities and the challenges of owning property here, yet many are choosing to expand their presence rather than reduce it.
Of course, buying a second property is not the right move for everyone. It may not make sense for buyers who are financially stretched, dislike the responsibilities of ownership, remain uncertain about their long term plans, or are simply looking for short term speculation.
However, if your first property exceeded expectations, you have developed a deep understanding of the market, your family's needs have evolved, or you find yourself wishing you had purchased more land years ago, it may be worth exploring what opportunities exist today.
From my perspective, this is one of the healthiest signals a market can produce. Not because it guarantees future appreciation, but because it reflects conviction, experience, and thoughtful ownership decisions.
The market is evolving beyond first time dream buyers. Increasingly, it is being shaped by people who already know Santa Teresa well and have decided they want a larger role in its future.
The first purchase creates discovery.
The second purchase often reflects clarity.
And right now, many experienced owners are acting on that clarity.
If you're considering expanding your presence in Santa Teresa, whether through land, an additional home, an income producing property, or a long term family investment, having local guidance can help you evaluate opportunities strategically and identify options that align with your long term goals.
Because a second property is rarely an impulse purchase.
It's usually the result of knowing exactly what matters most.
About The Author
Hi, I'm Jen Harter. For over 12 years, I've been helping people discover the Santa Teresa area and the Nicoya Peninsula—the beaches, the mountains, the quiet corners, and the hidden gems that make this part of Costa Rica feel like home.
Whether you're thinking about relocating, investing, or just daydreaming about life in paradise, I'm here to answer your questions and share what I've learned from living and working here. With offices across the country, I can also connect you with the right people if your curiosity takes you beyond Santa Teresa. There really is so much to explore.
I'm not here to push a sale. I want to give you honest insight, local perspective, and the space to figure out if Costa Rica really feels like the right fit for your next chapter. For many, the decision takes time—and that's perfectly okay. That's exactly why I do what I do.
If you want to chat, you can email me directly at jen@2crsantateresa.com. I personally respond to every message, whether you're ready to buy soon or just exploring ideas for the future. Sometimes, the best decisions start with a simple conversation—and in Costa Rica, that conversation could be the beginning of something amazing.
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