Costa Rica’s Most Exclusive Estates: Private Client Showcase

Costa Rica’s Most Exclusive Estates: Private Client Showcase

  • Daveed Hollander
  • 04/13/26

Over the past two decades, I’ve had the opportunity to work closely with private clients, investors, and developers acquiring some of the most compelling real estate assets across Costa Rica. What I’ve learned is that the term “luxury” is often used too broadly – and in many cases, inaccurately.

In Costa Rica’s luxury market, a true estate is something entirely different.

It’s defined by scale, positioning, privacy, and long-term optionality. It’s not just about architecture or finishes, but about how the land sits within its environment, how it can evolve, and how it aligns with a client’s broader vision, whether that’s lifestyle, investment, or legacy.

Why Exclusive Estates Matter in Today’s Market

Costa Rica has evolved into one of the most compelling lifestyle and investment markets globally, particularly for high-net-worth and ultra-high-net-worth buyers seeking a combination of stability, natural beauty, and value over the duration of ownership.

But what makes this market unique is not just demand, but constraint.

Strict environmental protections, limited coastal

 inventory, and increasingly defined zoning frameworks mean that truly exceptional properties are becoming scarce. As a result, the gap between standard luxury listings and genuinely irreplaceable estates has widened significantly.

For private clients, this creates a very specific type of opportunity. The focus shifts from simply acquiring property to identifying assets that hold long-term positioning – properties that combine lifestyle appeal with scarcity, development potential, and resilience as the market continues to mature.

 

Costa Rica Real Estate as a Wealth Preservation Strategy

For many private clients, the real appeal of an exclusive estate is durability. At this level, buyers are often less focused on chasing aggressive appreciation and more focused on holding assets that can preserve value, remain personally meaningful, and continue to perform across changing market cycles.

That is part of what makes estate-level acquisitions in Costa Rica so compelling. When a property offers privacy, land scale, personal use, and future flexibility all within a stable long-term hold, it begins to function as more than luxury real estate. It becomes a form of anchored capital – one that supports lifestyle today while still protecting strategic optionality for the future.

For private clients thinking in decades rather than seasons, that creates a very different investment profile.

How Private Clients Evaluate Estate-Level Opportunities

When I work with private clients evaluating opportunities in Costa Rica, the conversation rarely starts with the property itself. It starts with positioning. We look at:

  • How the land is situated: views, topography, access 

  • The level of privacy and control 

  • Infrastructure and viability over time

  • Development potential, even if not immediately utilized 

  • And how the asset fits within a broader portfolio or lifestyle plan 

 

For many of the families and investors I advise, privacy is only one part of the equation. Control matters just as much: control over the land, the setting, the surrounding experience, and, in some cases, the ability to preserve that asset across generations. That’s where estate-level opportunities begin to separate themselves from standard luxury inventory.

Optionality is another defining factor. The strongest estates are rarely one-dimensional. They may serve as a primary residence today, support rental or retreat use tomorrow, expand into a family compound, or simply remain a held, land-banked asset held for future generations. That is not incidental; it is part of what gives a true estate its long-term value.

Costa Rica also plays a very specific role for many private clients from a portfolio perspective. These acquisitions are often not just about buying a beautiful home, but about adding geographic diversification, real asset exposure, and lifestyle alignment within a stable jurisdiction. When that’s paired with privacy, scarcity, and control, the estate becomes a strategic allocation.

In many cases, the most valuable opportunities are not the most obvious ones. They’re the properties where multiple paths exist: personal use, income generation, future development, or long-term hold. This, combined with privacy, control, and strategic optionality, is what defines a true estate-level asset.

 

Four Estate Properties That Illustrate the Luxury Difference

To highlight the irreplaceable luxury available in Costa Rica today, I’d like to share a selection of properties that, in my experience, represent that distinction. Each reflects a different type of opportunity – from legacy-driven estates to development platforms – and more importantly, how I evaluate them through a private client lens.

Château Montage: A Legacy-Driven Architectural Estate

Escaleras (Dominical) | 4 Bedrooms | 7 Bathrooms | 4.07 Acres | $6,149,000

Located in Escaleras above Dominical, Château Montage is a rare example of what I would consider a true legacy property.

Set across more than four acres with expansive ocean and mountain views, this estate is not defined by its scale alone, but by how intentionally it integrates with the surrounding landscape. The architecture is designed to coexist with the environment, allowing the jungle, light, and natural elements to shape the experience of the home.

From a private client perspective, this is the type of asset that transcends typical valuation metrics. It’s not just about replacement cost or rental performance, but about ownership of something that is both architecturally and geographically irreplaceable.

>> View Property <<

Villa Cosara: Estate Living with Embedded Development Potential

Uvita | 16.44 Acres | $5,800,000

Villa Cosara represents a different type of opportunity – one that combines a fully realized estate with meaningful expansion potential.

Positioned within the Hermosa Retreat above Uvita, the property includes two existing residences, but more importantly, over 16 acres of land with multiple homesites and development flexibility. This creates a hybrid scenario: immediate lifestyle use paired with long-term upside. That combination is particularly attractive because it offers both present-day enjoyment and a clearer path to future expansion, without forcing the investor into a purely speculative development play from day one.

For many of the investors I work with, the real appeal lies in owning assets that preserve value, offer multiple use options, and create a lasting sense of control within a market defined by scarcity. You’re acquiring both a finished property and a platform – something that can evolve, whether through additional residences, a family compound, or a more structured development approach.

>> View Property <<

Villas Alturas: A Hospitality and Development Platform at Scale

Dominical | 12 Bedrooms | 12 Bathrooms | 86.22 Acres | $6,250,000

Opportunities at this scale are increasingly rare in Costa Rica in 2026.

Villas Alturas is a fully positioned development platform with over 86 acres of land, existing hospitality infrastructure, and a layout that supports phased expansion. The property offers multiple entry points depending on strategy. From a development standpoint, this is exactly the type of asset I spend a significant amount of time advising on. It allows for:

  • Immediate income through the existing hotel 

  • Brand positioning and operational presence 

  • Phased development of additional units or residences 

  • And long-term capital structuring with multiple exit strategies 

What makes a property like this truly compelling is not just its scale, but its relative execution advantage. Existing infrastructure and operational presence reduce some of the friction that often comes with large-scale development in Costa Rica, where entitlement timelines, environmental approvals, and infrastructure planning can otherwise slow momentum significantly.

For the right investor or group, this becomes less about acquisition and more about execution.

>> View Property <<

Escaleras Compound: Lifestyle, Income, and Strategic Flexibility

Dominical | 7 Bedrooms | 7 Bathrooms | 2.22 Acres | $3,700,000

This seven-bedroom compound in Escaleras represents one of the most balanced opportunities in the current market.

It combines a primary residence with a separate guest home, allowing for multiple use cases, from full-time living to a high-end rental or retreat-style programming. Its design, setting, and natural environment create a strong lifestyle experience, while the structure of the property supports income generation.

What makes this one particularly relevant in today’s market is its flexibility, including the seller’s openness to cryptocurrency transactions. As the market continues to evolve, I’m seeing more interest in alternative transaction structures, and properties like this sit at the intersection of lifestyle, investment, and innovation.

>> View Property <<

 

My Perspective After Two Decades in Costa Rica’s Luxury Market

Over the past two decades, I’ve had the opportunity to work across nearly every layer of Costa Rica’s real estate market, from representing individual luxury estates to advising on large-scale development land, boutique hospitality projects, and long-term investment strategies for private clients.

Through that work, and through my role as President & CEO of both Coldwell Banker Costa Rica and Vesta Group, I’ve been able to see how this market evolves – where capital flows, how regions develop, and which assets ultimately hold their value.

I’ve also been fortunate to operate within a global network at the highest level of the industry, ranking in the top 1% of Coldwell Banker agents worldwide and recognized among the Top 20 Luxury Brokers in Central America. 

My perspective has also been shaped through ongoing media coverage and market commentary, including features in The Wall Street Journal, La Nación, and Coldwell Banker Global Luxury® publications. 

That exposure allows me to evaluate opportunities not just within Costa Rica, but in the context of what global buyers are comparing them to. It also gives me something equally important: perspective on where the most meaningful opportunities are actually found. At this level of the market, many of the best estate acquisitions are not simply the ones that appear publicly, but the ones accessed through trusted relationships, local intelligence, and long-standing networks. For private clients, that access can be just as valuable as the asset itself.

Experience has taught me that not all high-end properties are created equal. The real difference lies in positioning — how the asset fits into a long-term strategy, how it evolves, and how it aligns with both lifestyle and investment objectives. That’s why my role has increasingly become less about brokerage and more about advisory. Because at this level, real estate is never just about the property, but about the decisions behind it.

Common Questions My Private Clients Ask

What defines a true estate in Costa Rica?

Scale, privacy, positioning, and long-term optionality. The best estates combine lifestyle value with scarcity and future flexibility.

Can estates also generate income?

Yes. Many high-end properties are structured to support rental income, hospitality use, or phased development.

How important is development potential?

Extremely. Even if not utilized immediately, development optionality is one of the key drivers of value. 

 

Final Takeaways

Costa Rica continues to attract global buyers looking for alignment, lifestyle, and positioning. But within that market, true estate-level opportunities remain limited. For my private clients, the focus should always be on:

  • Scarcity and positioning
  • Flexibility and optionality
  • Long-term value over short-term appeal
  • And access to the right opportunities, often beyond what is publicly visible

Because ultimately, the most successful acquisitions are not defined by what they are today, but by what they could become. If you're evaluating private client real estate investments, development opportunities, or relocation planning in Costa Rica, I invite you to schedule a private consultation directly with me.

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