Last updated: October 10, 2026 · By Clint Hansen, Broker (RB-21616) · The Hansen Ohana
| Wailea | Kihei | |
|---|---|---|
| Character | Master-planned resort community; landscaped, low-signage, coordinated design standards | Larger, more local, commercially mixed town |
| Housing mix | Mostly HOA-governed resort/golf-course condos, plus gated single-family subdivisions and estate homes | Condos dominate the coast in a wide range of ages and sizes; single-family more common upslope (e.g. Maui Meadows) |
| Typical buyer | Second-home owners, vacation-rental investors (where a building allows it), luxury primary residences | First-time Maui buyers, local families, vacation-rental investors, retirees |
| Beaches | Five named beaches (Keawakapu, Mokapu, Ulua, Wailea, Polo) linked by the Wailea Beach Path | Three Kamaole Beach Parks, Keawakapu at the south end, Sugar Beach to the north, Cove Park for beginner surfing |
| Dining & shopping | The Shops at Wailea and Wailea Town Center, plus resort-hotel dining | Local restaurants and everyday shopping centers spread along South Kihei Road |
| Vacation-rental picture | Building-by-building — some complexes permit it, some don't; verify per unit | Same building-by-building rule, across a much larger pool of condo complexes |
| Price level | Higher overall, reflecting resort amenities and HOA standards | Broader range with a generally easier entry point — see the live Truth Report for current figures |
| Walkability | Oceanfront coastal path of about 1.5 miles along the shoreline; access from a specific home or condo depends on its location and entrances | Many condos sit near the Kamaole parks; check the actual walking route from the specific property |
As of October 16, 2026, 28 Wailea/Makena homes closed over the trailing 12 months (October 17, 2025 to October 16, 2026), per Maui MLS data computed by MauiRealEstate.net.
As of October 16, 2026, the median sold price of a Wailea/Makena home over the trailing 12 months was $3,115,250 (n=28), per Maui MLS data computed by MauiRealEstate.net.
As of October 16, 2026, the median time from listing to closing for Wailea/Makena homes sold over the trailing 12 months was 114 days (n=28), per Maui MLS data computed by MauiRealEstate.net.
As of October 16, 2026, fewer than 8 Wailea/Makena homes closed in Q4 2026 to date (n=2), so no median is reported, per Maui MLS data computed by MauiRealEstate.net.
As of October 16, 2026, 27 Wailea/Makena homes were actively listed for sale (excluding Coming Soon), per Maui MLS data computed by MauiRealEstate.net.
As of October 16, 2026, 82 Wailea/Makena condos closed over the trailing 12 months (October 17, 2025 to October 16, 2026), per Maui MLS data computed by MauiRealEstate.net.
As of October 16, 2026, the median sold price of a Wailea/Makena condo over the trailing 12 months was $1,975,000 (n=82), per Maui MLS data computed by MauiRealEstate.net.
As of October 16, 2026, the median time from listing to closing for Wailea/Makena condos sold over the trailing 12 months was 121 days (n=82), per Maui MLS data computed by MauiRealEstate.net.
As of October 16, 2026, fewer than 8 Wailea/Makena condos closed in Q4 2026 to date (n=2), so no median is reported, per Maui MLS data computed by MauiRealEstate.net.
As of October 16, 2026, 77 Wailea/Makena condos were actively listed for sale (excluding Coming Soon), per Maui MLS data computed by MauiRealEstate.net.
| 12-mo closed | 12-mo median price | 12-mo median days to close | Q4 2026 to date closed | Q4 2026 to date median | Active now | |
|---|---|---|---|---|---|---|
| Homes | 28 | $3,115,250 | 114 | 2 | n<8 | 27 |
| Condos | 82 | $1,975,000 | 121 | 2 | n<8 | 77 |
Source: Maui MLS data via MauiRealEstate.net, computed from closed sales with a recorded sold price, as of October 16, 2026; medians are true medians.
Homes are single-family classes. Days to close runs from the listing date to the closing date. Medians are shown only when at least 8 sales support them. Wailea and Makena are one MLS area.
See the live Maui Truth Report for every district.
As of October 16, 2026, 115 Kihei homes closed over the trailing 12 months (October 17, 2025 to October 16, 2026), per Maui MLS data computed by MauiRealEstate.net.
As of October 16, 2026, the median sold price of a Kihei home over the trailing 12 months was $1,200,000 (n=115), per Maui MLS data computed by MauiRealEstate.net.
As of October 16, 2026, the median time from listing to closing for Kihei homes sold over the trailing 12 months was 108 days (n=115), per Maui MLS data computed by MauiRealEstate.net.
As of October 16, 2026, fewer than 8 Kihei homes closed in Q4 2026 to date (n=3), so no median is reported, per Maui MLS data computed by MauiRealEstate.net.
As of October 16, 2026, 64 Kihei homes were actively listed for sale (excluding Coming Soon), per Maui MLS data computed by MauiRealEstate.net.
As of October 16, 2026, 290 Kihei condos closed over the trailing 12 months (October 17, 2025 to October 16, 2026), per Maui MLS data computed by MauiRealEstate.net.
As of October 16, 2026, the median sold price of a Kihei condo over the trailing 12 months was $590,000 (n=290), per Maui MLS data computed by MauiRealEstate.net.
As of October 16, 2026, the median time from listing to closing for Kihei condos sold over the trailing 12 months was 118 days (n=290), per Maui MLS data computed by MauiRealEstate.net.
As of October 16, 2026, 17 Kihei condos have closed in Q4 2026 to date (since October 1, 2026), at a median sold price of $489,000, per Maui MLS data computed by MauiRealEstate.net.
As of October 16, 2026, 233 Kihei condos were actively listed for sale (excluding Coming Soon), per Maui MLS data computed by MauiRealEstate.net.
| 12-mo closed | 12-mo median price | 12-mo median days to close | Q4 2026 to date closed | Q4 2026 to date median | Active now | |
|---|---|---|---|---|---|---|
| Homes | 115 | $1,200,000 | 108 | 3 | n<8 | 64 |
| Condos | 290 | $590,000 | 118 | 17 | $489,000 | 233 |
Source: Maui MLS data via MauiRealEstate.net, computed from closed sales with a recorded sold price, as of October 16, 2026; medians are true medians.
Homes are single-family classes. Days to close runs from the listing date to the closing date. Medians are shown only when at least 8 sales support them. Kihei excludes Maui Meadows, which is its own district.
See the live Maui Truth Report for every district.
Matched to the kind of buyer, not the area name. Fit here is general; the specific building, its governing documents and the walking route from the property decide each case. For current numbers, see the live Truth Report.
| Buyer | Wailea fit | Kihei fit | What decides it |
|---|---|---|---|
| Second-home buyer | Strong: resort polish, coordinated design standards, HOA-managed upkeep | Good: wide range of condo styles and sizes, more everyday shops and local restaurants | How much you want resort-style standards and managed upkeep versus a more local, varied setting |
| Full-time relocating family | Possible: gated single-family subdivisions exist, though much of the housing is HOA-governed condos | Strong: larger, more local town; single-family homes more common upslope, as in Maui Meadows | Single-family versus condo, and daily errands versus resort setting |
| First Maui purchase on a budget | Narrower: Wailea sits at the higher price level, reflecting resort amenities and HOA standards | Strong: broader range with a generally easier entry point; south Kihei is closest to Wailea in feel | How much of the budget goes to amenities and HOA standards versus space and flexibility |
| Vacation-rental investor | Depends on the building: some complexes permit rentals, some do not | Depends on the building: same rule across a much larger pool of condo complexes | Rental permissions are decided building by building, so verify per unit before location. No income figures are given here |
| Luxury / estate buyer | Strong: gated single-family subdivisions, estate homes, resort amenities and golf | Limited on the coast; Maui Meadows offers larger single-family lots with ocean views | Resort-community standards versus space and privacy upslope |
| Retiree downsizing | Good: low-maintenance, HOA-managed resort condos and a landscaped setting | Good: wide range of condo sizes and ages; many sit near the Kamaole parks | Walkability varies by property, so check the actual route to the beach and shops |
| Remote worker | Fits a quiet, uniform, landscaped setting | Fits a buyer who wants shops, restaurants and everyday services close by | Daily rhythm, and whether you want a resort setting or a town |
The honest middle ground for several of these buyers is south Kihei or Maui Meadows. Whatever the persona, compare the governing documents and ownership costs of each property on your shortlist.
Wailea is a master-planned resort community, which means its roads, landscaping, golf courses, resorts, and condo complexes were built under a coordinated plan rather than growing up piecemeal — the result is a more uniform, heavily landscaped feel than older Maui towns, with low signage and consistent building setbacks. Its coastline includes five public beaches (Keawakapu, Mokapu, Ulua, Wailea, and Polo), and an oceanfront coastal path of about 1.5 miles runs along the shoreline past resort hotels including the Grand Wailea, the Four Seasons, the Fairmont Kea Lani, and the Andaz Maui — though access from an individual home or condo depends on its location and entrances, so check the actual walking route during your property visit. Wailea's golf is a separate comparison from the coastal path: the operator lists the Gold/Emerald clubhouse and the Blue facility at separate locations, so if golf is part of your routine, check the route from the property to the clubhouse you expect to use. Housing is mostly HOA-governed condominiums plus a smaller share of gated single-family subdivisions and estate homes. Buying here means buying into resort polish and consistent community standards, generally at a higher price level.
Kihei is South Maui's larger, more local town, running along South Kihei Road between North Kihei/Ma'alaea and the Wailea border. Its defining feature is a long condominium corridor built up over decades across a wide range of building styles, sizes, ages, and price points, with single-family homes more common upslope in areas like Maui Meadows. The three Kamaole Beach Parks anchor the central coastline, with Keawakapu at the south end, Sugar Beach to the north, and Cove Park for beginner surfing and paddleboarding. Kihei has more everyday shopping centers and local restaurants than Wailea's resort-centered dining, and it suits a wider range of buyers — from first-time Maui purchasers to local families, vacation-rental investors, and retirees — because its rules and price points vary so much within the town itself.
Wailea and Kihei aren't opposite ends of the island — they're neighbors, and the border between them is genuinely blurry. Keawakapu Beach sits right at that border and is claimed by both areas' guides for good reason: it's shared. South Kihei, the section closest to Wailea, trades some of North Kihei's distance and quiet for a setting that reads closer to Wailea's, while still keeping Kihei's broader price range. Whichever area you lean toward, compare the governing documents and ownership costs for the specific properties on your shortlist — an area's name does not tell you which restrictions, fees or amenities apply to a particular home or condominium. Upslope from the coast, Maui Meadows is a residential subdivision of larger single-family lots with ocean views, sitting between the two areas geographically as much as it does in character — more space and privacy than a Wailea or Kihei condo, at the cost of a longer walk (or drive) to the water. If you like the idea of Wailea's setting but not its price level or HOA restrictions, south Kihei and Maui Meadows are exactly where the two areas' honest middle ground lives.
The questions the Hansen Ohana asks buyers weighing Wailea against Kihei are rarely about the areas themselves — they're about the buyer. Is this a primary residence, a second home, or a vacation-rental investment? Rental permissions vary building by building in both Wailea and Kihei, so that answer narrows the search before location does. How much of the budget do you want going toward resort amenities and HOA-managed design standards versus toward square footage and flexibility? Do you want to spend your time on a golf course and at resort restaurants, or browsing a wider mix of local shops and restaurants? And how much does walking to the beach matter, compared with the extra space a single-family lot in Wailea's upland edges or in Maui Meadows can offer? None of these questions have a universally right answer — they just point toward Wailea, Kihei, or the middle ground between them.
Picture an ordinary Tuesday. Where would you have breakfast, walk, shop or meet friends? Which trips would you want to make on foot? Which amenities would you actually use? Bring those answers to the property comparison, along with your plans for how often you will be here.
For a full walkthrough of each area on its own, see the Wailea neighborhood guide and the Kihei neighborhood guide. If you're ready to talk to someone local about either market, see Best Real Estate Agent in Wailea (2026 Guide) and Best Real Estate Agent in Kihei (2026 Guide). For current, un-stale pricing and market data across South Maui, see the quarterly Maui Truth Report, and for the full library of Maui area and buyer guides, see the Maui Guides hub. To compare the two markets directly, see two-bedroom condos in Wailea at or under $1,500,000 and two-bedroom condos in Kihei at or under $1,500,000.
The Hansen Ohana's office sits inside Wailea Town Center, at the entrance to Wailea just minutes from the
Kihei line — so weighing Wailea against Kihei is a conversation the team has with buyers every week. Broker
Clint Hansen (RB-21616), Maui-born with 26 years
in real estate, and Principal Broker Bob
Hansen (RB-17532), with 40+ years, lead a family team with 100+ combined years and 1,000+ transactions
across Maui — including both of these markets.
161 Wailea Ike Place, A-106, Wailea, Maui, HI 96753
Office: (808) 743-1214 · clinthansen@mauirealestate.net
