EXCELLENCE IN GUANACASTE

Josh Roistacher
Real Estate Group

Josh helps buyers and investors find high-performing properties across Guanacaste's most desirable coastal markets — backed by a decade of hands-on real estate experience, two successful company exits, and the perspective of someone who actually moved here with his family.

BACKGROUND & MY STORY

The background that changes the advice you get

Most real estate agents sell property. Josh has built businesses from scratch, scaled teams across multiple countries, and sat on both sides of high-stakes transactions — as an operator, an investor, and now as the person who guides your deal.

Before real estate, Josh was employee number five at HONK Technologies — a roadside assistance and connected car logistics platform he helped build from the ground up. In 2026, HONK was acquired by Frontenac Capital, combined with CurbsideSOS, and brought in the founding team behind Grubhub to lead its next chapter.

HONK is one of two companies Josh has successfully exited. In 2023, he moved his family from California to Guanacaste. Not to vacation. To live.

Operator mindset

Built and scaled teams of 150+ across multiple countries. Clear process, no surprises, full support after closing.

Investor perspective

A decade of personal real estate investing, STR management, and renovation before representing a client.

Local by choice

Josh didn't relocate here for business. He relocated for life. His kids go to school here. He knows what the market feels like.

TRACK RECORD

Consistent results across Guanacaste's most competitive markets

From boutique hotels and 14-unit apartment buildings to new construction villas and Reserva Conchal residences — Josh has closed transactions across the full spectrum of Guanacaste's luxury and investment market. Every deal is handled with the same discipline: priced right, marketed well, and negotiated to protect your position.

View notable sales →
FOCUS AREAS

Markets served

  • Playa Grande
  • Playa Langosta
  • Tamarindo
  • Potrero
  • Playa Flamingo
  • Reserva Conchal
  • Playa Avellanas
  • Las Catalinas
  • Las Ventanas
  • Palm Beach Estates
AREAS OF EXPERTISE

Specializations

  • Luxury vacation homes
  • Short-term rentals
  • Beachfront residences
  • Multi-unit investments
  • Boutique hotels
  • New construction
SERVICES

Buyer & Seller Services

Buyer services

Strategic acquisition roadmap

Built around your financial targets, timeline, and lifestyle goals.

Off-market access

Through KRAIN's regional network and direct relationships with developers and sellers.

End-to-end support

From first tour to closing and beyond, including post-closing introductions to contractors and property managers.

Seller services

Data-informed pricing

Real market comparables to position your property for maximum competitive leverage.

High-production marketing

Photography, video, and targeted campaigns reaching buyers in North America and Europe.

Creative deal-making

Josh secured a House Hunters International feature for a property that sat unsold for 1+ year. Sold shortly after airing.

CLIENTS

What clients say

"From the initial 'get to know the area' tours to finding legal counsel, inspections, and closing support — Josh was a true partner all the way through. This was our first time buying property in a foreign country, but Josh always ensured we had the information we needed to make decisions."

— Ron Dalla, USA

"Josh was not just an agent, he was a support. He followed up at every level — even during the floods this fall, he wanted to make sure we were safe and told us which route to take. The most personalized service. Krain is lucky to have Josh on their team."

— Annie & Steve, Quebec, Canada

"I had gone through a couple of realtors who did very little to market my farm. Once I switched to KRAIN, we were under contract in months."

— Molly Niederberger, USA
MISSION

To help buyers, sellers, and investors make smart real estate decisions in Guanacaste — with clear information, honest guidance, and support that does not stop at closing.

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