Selling A Luxury Home In Wailea And Makena
February 19, 2026
February 19, 2026
Thinking about selling your Wailea or Makena luxury home or condo in 96753? In this resort corridor, small choices about preparation, pricing, and timing can shift your result by six figures. You want a smooth sale, strong offers, and a buyer who values the lifestyle your property delivers. This guide walks you through the steps that work in Wailea and Makena today, including how new rental rules, insurance, and seasonality affect your strategy. Let’s dive in.
Wailea and Makena sit in one of Maui’s highest-value corridors. Recent public snapshots show a gap between asking prices and closed prices, especially when you compare luxury single-family homes with the broader zip-level median. The takeaway for you is simple. Use a tight set of comps matched to your property type and micro-location, not a generic zip average.
Ultra-luxury Makena estates often trade far above the corridor median and can take longer to sell than mid-market resort condos. Expect a smaller, more selective buyer pool at the very top end and plan for longer days on market with more negotiation around terms. For resort-oriented condos, buyer demand is partly shaped by vacation-rental performance. According to the November 2025 Hawai‘i Vacation Rental Performance Report, Wailea/Kīhei occupancy was about 48.5 percent for that month, with averages that move through the seasons. These metrics help investors evaluate income potential and can influence what they are willing to pay. You can review the statewide data in the Hawai‘i Tourism Authority’s report.
New short-term rental rules are also changing the condo landscape. Maui County’s Bill 9, signed on December 15, 2025, begins phasing out certain apartment-zoned transient vacation rentals and sets paths for units to convert back to long-term use or pursue rezoning. Sellers should not assume STR rights. Confirm whether your parcel appears on the former Minatoya list, whether it sits in a hotel or resort zoning district, and how changes could affect your buyer pool. Read more about the policy change in this MauiNow summary.
Finally, be aware of Maui County’s property tax tiers and payment deadlines. Classifications for non-owner-occupied and transient-vacation categories carry higher rates, which can affect closing prorations. Check the County’s notices and calendars on the Maui County site as you plan your timeline.
Price your home using a narrow, relevant comp set. Focus on your specific community or building, view plane and access, and the most recent closed sales that mirror your property’s quality and renovations. A thoughtful range, supported by data, helps you attract real buyers without giving up leverage.
Because sale-to-list ratios have been below 100 percent in some recent snapshots, build room for negotiation while staying anchored to what appraisals can support. For high-end properties, prepare an appraisal packet. Include recent comps with notes, a upgrades list with contractor receipts, permits and final inspection documents for renovations, and a floor plan. If a buyer is financing, make sure their lender can underwrite the HOA or AOAO insurance details that are common in Wailea condo towers.
Luxury buyers expect transparency and clean disclosures. A pre-list home inspection plus targeted specialist reports help you find and fix issues on your schedule. Common items include roof, pool or spa systems, HVAC, electrical panel, and termite or WDO. Pre-inspections are a proven way to reduce renegotiation risk during escrow. For a national overview of why sellers do this, see the Washington Post’s discussion of pre-sale inspections. Plan two to six weeks for any corrective work, depending on scope.
Coastal homes need special attention. Salt air can accelerate corrosion on railings, lanai hardware, and pool equipment, so small deferred items can become big buyer talking points. For condos, request and review the AOAO reserve study and master policy summary early.
If your property uses a cesspool, Hawaii law requires conversion on a statewide timeline. The University of Hawai‘i and the Department of Health maintain a parcel-level priority map and grant information. Use the Hawai‘i Cesspool Prioritization Tool to check status and disclose what you learn. Conversion can be a significant cost, often in the mid–five figures, which is why buyers consider it in their underwriting. For added context on costs, Civil Beat provides a helpful overview of statewide cesspool issues and expenses in this article.
After the 2023 wildfires, the state moved to stabilize hurricane and condo coverage. Legislation reactivated the Hawai‘i Hurricane Relief Fund and expanded insurer-of-last-resort tools, which has helped with availability. As a seller, gather your AOAO master policy details and any recent notices about premiums, sublimits, or special assessments. These items can affect buyers’ financing and comfort level. Learn more about the state program changes in this insurance industry brief.
Pull together a clean disclosure packet so buyers can move quickly:
Buyers in Wailea and Makena are purchasing a feeling of indoor and outdoor flow. Focus on the lanai, pool deck, and privacy screens in the landscape, as much as the interiors. Professional staging for both indoor and outdoor spaces usually supports faster sales and stronger offers. Allow two to six weeks to book vendors, complete any refresh, and schedule media.
A full media suite is non-negotiable for this market. Include day and twilight photography, aerial drone imagery and a short aerial clip, a cinematic property film of 60 to 120 seconds that shows the lifestyle, a 3D walkthrough, and a dimensioned floor plan. For high-end listings, a dedicated single-property site with a downloadable brochure lets remote and international buyers study your home before booking a flight.
Syndication through the MLS and major portals is the baseline. Layer on invitation-only luxury networks where available, targeted digital campaigns to high-net-worth audiences, and direct outreach to top brokers who regularly bring qualified buyers to South Maui. Curated private showings and broker previews in the first week help create momentum while protecting your privacy.
Maui’s visitor pattern matters for second-home buyers. Winter and the spring shoulder often bring more qualified visitors, while quality buyers also arrive year-round. Use market data to plan your launch and align broker previews with natural travel windows. You can see the broader seasonality in the Hawai‘i Tourism Authority occupancy report.
Structure creates speed. A proven approach includes pre-list prep two to four weeks ahead, then a coordinated day-one release supported by broker previews, email to curated lists, and targeted digital ads. Track engagement and be ready to recalibrate at 30, 60, and 90 days. For a simple framework, review this listing launch guide.
Many Wailea and Makena owners live on the mainland or abroad. A single, full-service team can manage staging, vendor scheduling, AOAO communication, showings, and escrow coordination so you do not have to be here in person. Professional vacation rental and property managers in the area also provide 24/7 support, cleaning, and preventive maintenance during a listing campaign, which helps keep your home show-ready. You can see the range of operational support common in Wailea through this overview of local vacation-rental services.
Build a team with these roles at minimum:
For privacy and security, use a smart lock or secure lockbox, require proof of funds or a lender letter before showings, and host escorted tours only. Set a reporting cadence that fits your needs, such as a weekly showings summary and a monthly vendor spend recap.
When it is time to close, you can pre-authorize a local title company to help with signing. Confirm any tax withholding obligations for nonresident sellers and make sure the buyer’s loan program matches the HOA or AOAO insurance profile to avoid last-minute issues.
You deserve a partner who knows this corridor and manages every detail with care. Our family-led team is based at The Shops at Wailea and operates under the Hawai‘i Life umbrella, which gives your listing local credibility and global reach. We combine generational Maui knowledge with concierge project management, premium media, and a modern tech stack that keeps qualified buyers engaged. Whether you live here full time or sell from the mainland, we coordinate everything so you can move forward with confidence.
Ready to talk strategy for your Wailea or Makena property in 96753? Connect with MacArthur Team Maui to get a tailored plan, a precise price range, and a polished launch that brings your best buyers to the table.
Living in a tropical paradise like Maui comes with its own set of unique maintenance needs for homeowners.
The island’s natural beauty and diverse ecosystems make it a truly unique and enchanting destination.
The North Shore’s powerful waves and consistent swells make it an ideal destination for surfers.
Upcountry Maui has become a sought-after destination for homebuyers looking to escape the hustle.
Connect with a trusted Maui real estate team ready to guide you confidently, whether buying, selling, or exploring island opportunities tailored to your lifestyle.