Luxury & Vacation Homes on the Garden Isle
Jennifer has been representing buyers and sellers of luxury estates, resort properties, and second homes in Princeville, Hanalei, Kilauea, and Poipu since 1999.
A trusted name in Kauai real estate for more than 25 years
Jennifer Easterly is a top-producing Broker Associate with Aloha Sotheby's International Realty and one of Kauai's most accomplished real estate professionals. Licensed in Hawaiʻi since 1999, she has represented hundreds of buyers and sellers, consistently ranking among the top-performing agents in the Sotheby's International Realty network, with recognition in Hawaiʻi Business Magazine's Top 100 Realtors and RealTrends Verified rankings.
Born into a family of real estate professionals, Jennifer moved from Phoenix to Kauai in the late 1990s to teach at Kilauea Elementary School on the North Shore. Drawn to the island's natural beauty and strong sense of community, she made Kauai her permanent home. More than twenty-five years later, her deep local knowledge gives clients an insider's view of the island's neighborhoods and market.
Today, Jennifer specializes in luxury homes, resort properties, ocean-view residences, and vacation and second-home properties across Kauai. Her experience managing custom home projects and renovations gives clients a rare lifestyle-and-ownership perspective on every property.
As a leading Realtor with Aloha Sotheby's International Realty, Jennifer's listings benefit from the global reach of the Sotheby's International Realty network and syndication across Mansion Global, Financial Times, Nikkei, Juwai, and The Wall Street Journal network.
Focused expertise, exceptional results
Luxury Homes & Estates
Distinctive oceanfront and ocean-view residences, resort properties, and legacy estates across Kauai's North and South Shores, marketed globally through the Sotheby's International Realty network.
Vacation & Second-Home Properties
Guiding out-of-state and international buyers through the full process of acquiring a second home or vacation rental property, including 1031 exchanges, renovations, and long-distance transactions.
Kauai’s North & South Shores
Jennifer lives in Princeville and represents buyers and sellers throughout Kauai’s most sought-after communities.
Jennifer's home community. Gated estates, golf-course living, and dramatic North Shore ocean views.
Legacy beachfront homes and laid-back luxury along one of Hawaiʻi’s most iconic bays.
Agricultural estates, ocean-view acreage, and quiet North Shore lifestyle properties.
Kauai's sunny South Shore. Resort condos, vacation rentals, and oceanfront second homes.
What clients say
Jennifer is an excellent real estate professional. She helped our family purchase 3 properties in Princeville. We were doing everything long distance and under a tight timeline with a real estate 1031 Exchange deadline. Additionally we took on some renovations on the properties. Jennifer was very helpful with the contractors and supplies. Her knowledge and years of experience were extremely helpful. We could not have done it without her. I highly recommend Jennifer Easterly for the acquisition or sale of your real estate in Kauai. She is one of the good ones!
Jennifer Easterly is by far the most engaging, intelligent, professional, and dedicated realtor with whom I have ever worked. She is highly respected in the greater Kauai community, both as a professional, and as a dedicated community volunteer. She has a deep and abiding respect for Hawaiian history and culture. I endorse Jennifer’s technical skills as well as applaud her stature as a reliable, honest realtor who fully understands the finer details of effectively doing business in Kauai.
I have worked with Jenn on the sale of my personal home and also most recently the purchase of a lot in Kalaheo. Both experiences have been such a smooth and positive experience. Jenn possesses the knowledge necessary for navigating the Kauai real estate market. I can promise with Jenn you will not just have a great real estate agent but also make a lifelong friend!
More reviews here
Kauai market insight
Quarterly notes on the North Shore market, island living, and buying or selling on Kauai. New posts coming soon.
Questions buyers and sellers ask
Jennifer Easterly is a top-producing Broker Associate with Aloha Sotheby's International Realty based in Princeville. Licensed in Hawaiʻi since 1999, she is consistently ranked among the top-performing agents in the Sotheby's International Realty network, with recognition in Hawaiʻi Business Magazine's Top 100 Realtors and RealTrends Verified rankings.
Jennifer Easterly specializes in vacation and second-home properties across Kauai's North Shore, including Hanalei and Kilauea, and has extensive experience with 1031 exchanges, renovations, and long-distance transactions for out-of-state buyers.
Jennifer Easterly of Aloha Sotheby's International Realty specializes in luxury homes, resort properties, and oceanfront estates in Poipu and throughout Kauai's South Shore.