Kapalua Luxury Living

Pineapple Hill

With exquisite views, elegantly constructed homes, and everything needed to experience heaven on earth, the coveted homes of Pineapple Hill Estates are now for sale on the market. Designed to amplify Maui’s natural beauty and to ensure graceful and easy living, the houses on Pineapple Hill are the second phase of a secure gated community established in 1989.


With a strong and steadily increasing market value, the best time to invest in paradise is right now. Situated on the slopes of the West Maui mountains, Pineapple Hill has access to the raw beauty of some of Hawaii’s best hiking trails. From the mountains to the coast, experiences of pristine natural scenery are readily available. Enjoy the white sand and world-class surfing of the tropical beaches or the breathtaking views from the mountains – truly what is for sale at Pineapple Hill is not just a home but heaven on earth.

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Real Estate Statistics

Average Price $4.9M
Lowest Price $3.9M
Highest Price $5.2M
Total Listings 7
Avg. Days On Market 163
Avg. Price/SQFT $1.3K

Property Types (active listings)

Pineapple Hill Homes For Sale

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Listing Image for 232 Crestview Rd 1 of 46 Listing Image for 232 Crestview Rd 2 of 46 Listing Image for 232 Crestview Rd 3 of 46 Listing Image for 232 Crestview Rd 4 of 46 Listing Image for 232 Crestview Rd 5 of 46 Listing Image for 232 Crestview Rd 6 of 46 Listing Image for 232 Crestview Rd 7 of 46 Listing Image for 232 Crestview Rd 8 of 46 Listing Image for 232 Crestview Rd 9 of 46 Listing Image for 232 Crestview Rd 10 of 46 Listing Image for 232 Crestview Rd 11 of 46 Listing Image for 232 Crestview Rd 12 of 46 Listing Image for 232 Crestview Rd 13 of 46 Listing Image for 232 Crestview Rd 14 of 46 Listing Image for 232 Crestview Rd 15 of 46 Listing Image for 232 Crestview Rd 16 of 46 Listing Image for 232 Crestview Rd 17 of 46 Listing Image for 232 Crestview Rd 18 of 46 Listing Image for 232 Crestview Rd 19 of 46 Listing Image for 232 Crestview Rd 20 of 46 Listing Image for 232 Crestview Rd 21 of 46 Listing Image for 232 Crestview Rd 22 of 46 Listing Image for 232 Crestview Rd 23 of 46 Listing Image for 232 Crestview Rd 24 of 46 Listing Image for 232 Crestview Rd 25 of 46 Listing Image for 232 Crestview Rd 26 of 46 Listing Image for 232 Crestview Rd 27 of 46 Listing Image for 232 Crestview Rd 28 of 46 Listing Image for 232 Crestview Rd 29 of 46 Listing Image for 232 Crestview Rd 30 of 46 Listing Image for 232 Crestview Rd 31 of 46 Listing Image for 232 Crestview Rd 32 of 46 Listing Image for 232 Crestview Rd 33 of 46 Listing Image for 232 Crestview Rd 34 of 46 Listing Image for 232 Crestview Rd 35 of 46 Listing Image for 232 Crestview Rd 36 of 46 Listing Image for 232 Crestview Rd 37 of 46 Listing Image for 232 Crestview Rd 38 of 46 Listing Image for 232 Crestview Rd 39 of 46 Listing Image for 232 Crestview Rd 40 of 46 Listing Image for 232 Crestview Rd 41 of 46 Listing Image for 232 Crestview Rd 42 of 46 Listing Image for 232 Crestview Rd 43 of 46 Listing Image for 232 Crestview Rd 44 of 46 Listing Image for 232 Crestview Rd 45 of 46 Listing Image for 232 Crestview Rd 46 of 46

$5,200,000

Pineapple Hill

232 Crestview Rd, Kapalua

3 Beds 3 Baths 3,354 SqFt Residential MLS® # 408178

Days on Market: 123

Listing Image for 1008 Sunset Pl 1 of 50 Listing Image for 1008 Sunset Pl 2 of 50 Listing Image for 1008 Sunset Pl 3 of 50 Listing Image for 1008 Sunset Pl 4 of 50 Listing Image for 1008 Sunset Pl 5 of 50 Listing Image for 1008 Sunset Pl 6 of 50 Listing Image for 1008 Sunset Pl 7 of 50 Listing Image for 1008 Sunset Pl 8 of 50 Listing Image for 1008 Sunset Pl 9 of 50 Listing Image for 1008 Sunset Pl 10 of 50 Listing Image for 1008 Sunset Pl 11 of 50 Listing Image for 1008 Sunset Pl 12 of 50 Listing Image for 1008 Sunset Pl 13 of 50 Listing Image for 1008 Sunset Pl 14 of 50 Listing Image for 1008 Sunset Pl 15 of 50 Listing Image for 1008 Sunset Pl 16 of 50 Listing Image for 1008 Sunset Pl 17 of 50 Listing Image for 1008 Sunset Pl 18 of 50 Listing Image for 1008 Sunset Pl 19 of 50 Listing Image for 1008 Sunset Pl 20 of 50 Listing Image for 1008 Sunset Pl 21 of 50 Listing Image for 1008 Sunset Pl 22 of 50 Listing Image for 1008 Sunset Pl 23 of 50 Listing Image for 1008 Sunset Pl 24 of 50 Listing Image for 1008 Sunset Pl 25 of 50 Listing Image for 1008 Sunset Pl 26 of 50 Listing Image for 1008 Sunset Pl 27 of 50 Listing Image for 1008 Sunset Pl 28 of 50 Listing Image for 1008 Sunset Pl 29 of 50 Listing Image for 1008 Sunset Pl 30 of 50 Listing Image for 1008 Sunset Pl 31 of 50 Listing Image for 1008 Sunset Pl 32 of 50 Listing Image for 1008 Sunset Pl 33 of 50 Listing Image for 1008 Sunset Pl 34 of 50 Listing Image for 1008 Sunset Pl 35 of 50 Listing Image for 1008 Sunset Pl 36 of 50 Listing Image for 1008 Sunset Pl 37 of 50 Listing Image for 1008 Sunset Pl 38 of 50 Listing Image for 1008 Sunset Pl 39 of 50 Listing Image for 1008 Sunset Pl 40 of 50 Listing Image for 1008 Sunset Pl 41 of 50 Listing Image for 1008 Sunset Pl 42 of 50 Listing Image for 1008 Sunset Pl 43 of 50 Listing Image for 1008 Sunset Pl 44 of 50 Listing Image for 1008 Sunset Pl 45 of 50 Listing Image for 1008 Sunset Pl 46 of 50 Listing Image for 1008 Sunset Pl 47 of 50 Listing Image for 1008 Sunset Pl 48 of 50 Listing Image for 1008 Sunset Pl 49 of 50 Listing Image for 1008 Sunset Pl 50 of 50

$5,195,000

↓ $100,000

Pineapple Hill

1008 Sunset Pl, Kapalua

3 Beds 3.5 Baths 4,574 SqFt Residential MLS® # 408268

Days on Market: 111

Listing Image for 104 Woodrose Pl 1 of 42 Listing Image for 104 Woodrose Pl 2 of 42 Listing Image for 104 Woodrose Pl 3 of 42 Listing Image for 104 Woodrose Pl 4 of 42 Listing Image for 104 Woodrose Pl 5 of 42 Listing Image for 104 Woodrose Pl 6 of 42 Listing Image for 104 Woodrose Pl 7 of 42 Listing Image for 104 Woodrose Pl 8 of 42 Listing Image for 104 Woodrose Pl 9 of 42 Listing Image for 104 Woodrose Pl 10 of 42 Listing Image for 104 Woodrose Pl 11 of 42 Listing Image for 104 Woodrose Pl 12 of 42 Listing Image for 104 Woodrose Pl 13 of 42 Listing Image for 104 Woodrose Pl 14 of 42 Listing Image for 104 Woodrose Pl 15 of 42 Listing Image for 104 Woodrose Pl 16 of 42 Listing Image for 104 Woodrose Pl 17 of 42 Listing Image for 104 Woodrose Pl 18 of 42 Listing Image for 104 Woodrose Pl 19 of 42 Listing Image for 104 Woodrose Pl 20 of 42 Listing Image for 104 Woodrose Pl 21 of 42 Listing Image for 104 Woodrose Pl 22 of 42 Listing Image for 104 Woodrose Pl 23 of 42 Listing Image for 104 Woodrose Pl 24 of 42 Listing Image for 104 Woodrose Pl 25 of 42 Listing Image for 104 Woodrose Pl 26 of 42 Listing Image for 104 Woodrose Pl 27 of 42 Listing Image for 104 Woodrose Pl 28 of 42 Listing Image for 104 Woodrose Pl 29 of 42 Listing Image for 104 Woodrose Pl 30 of 42 Listing Image for 104 Woodrose Pl 31 of 42 Listing Image for 104 Woodrose Pl 32 of 42 Listing Image for 104 Woodrose Pl 33 of 42 Listing Image for 104 Woodrose Pl 34 of 42 Listing Image for 104 Woodrose Pl 35 of 42 Listing Image for 104 Woodrose Pl 36 of 42 Listing Image for 104 Woodrose Pl 37 of 42 Listing Image for 104 Woodrose Pl 38 of 42 Listing Image for 104 Woodrose Pl 39 of 42 Listing Image for 104 Woodrose Pl 40 of 42 Listing Image for 104 Woodrose Pl 41 of 42 Listing Image for 104 Woodrose Pl 42 of 42

$5,165,000

↓ $230,000

Pineapple Hill

104 Woodrose Pl, Kapalua

4 Beds 3.5 Baths 3,315 SqFt Residential MLS® # 407481

Days on Market: 183

Listing Image for 620 Silversword Dr 26 1 of 49 Listing Image for 620 Silversword Dr 26 2 of 49 Listing Image for 620 Silversword Dr 26 3 of 49 Listing Image for 620 Silversword Dr 26 4 of 49 Listing Image for 620 Silversword Dr 26 5 of 49 Listing Image for 620 Silversword Dr 26 6 of 49 Listing Image for 620 Silversword Dr 26 7 of 49 Listing Image for 620 Silversword Dr 26 8 of 49 Listing Image for 620 Silversword Dr 26 9 of 49 Listing Image for 620 Silversword Dr 26 10 of 49 Listing Image for 620 Silversword Dr 26 11 of 49 Listing Image for 620 Silversword Dr 26 12 of 49 Listing Image for 620 Silversword Dr 26 13 of 49 Listing Image for 620 Silversword Dr 26 14 of 49 Listing Image for 620 Silversword Dr 26 15 of 49 Listing Image for 620 Silversword Dr 26 16 of 49 Listing Image for 620 Silversword Dr 26 17 of 49 Listing Image for 620 Silversword Dr 26 18 of 49 Listing Image for 620 Silversword Dr 26 19 of 49 Listing Image for 620 Silversword Dr 26 20 of 49 Listing Image for 620 Silversword Dr 26 21 of 49 Listing Image for 620 Silversword Dr 26 22 of 49 Listing Image for 620 Silversword Dr 26 23 of 49 Listing Image for 620 Silversword Dr 26 24 of 49 Listing Image for 620 Silversword Dr 26 25 of 49 Listing Image for 620 Silversword Dr 26 26 of 49 Listing Image for 620 Silversword Dr 26 27 of 49 Listing Image for 620 Silversword Dr 26 28 of 49 Listing Image for 620 Silversword Dr 26 29 of 49 Listing Image for 620 Silversword Dr 26 30 of 49 Listing Image for 620 Silversword Dr 26 31 of 49 Listing Image for 620 Silversword Dr 26 32 of 49 Listing Image for 620 Silversword Dr 26 33 of 49 Listing Image for 620 Silversword Dr 26 34 of 49 Listing Image for 620 Silversword Dr 26 35 of 49 Listing Image for 620 Silversword Dr 26 36 of 49 Listing Image for 620 Silversword Dr 26 37 of 49 Listing Image for 620 Silversword Dr 26 38 of 49 Listing Image for 620 Silversword Dr 26 39 of 49 Listing Image for 620 Silversword Dr 26 40 of 49 Listing Image for 620 Silversword Dr 26 41 of 49 Listing Image for 620 Silversword Dr 26 42 of 49 Listing Image for 620 Silversword Dr 26 43 of 49 Listing Image for 620 Silversword Dr 26 44 of 49 Listing Image for 620 Silversword Dr 26 45 of 49 Listing Image for 620 Silversword Dr 26 46 of 49 Listing Image for 620 Silversword Dr 26 47 of 49 Listing Image for 620 Silversword Dr 26 48 of 49 Listing Image for 620 Silversword Dr 26 49 of 49

$4,975,000

Pineapple Hill

620 Silversword Dr 26, Kapalua

4 Beds 4.5 Baths 3,445 SqFt Residential MLS® # 409156

Days on Market: 20

Listing Image for 112 Pulelehua St 1 of 50 Listing Image for 112 Pulelehua St 2 of 50 Listing Image for 112 Pulelehua St 3 of 50 Listing Image for 112 Pulelehua St 4 of 50 Listing Image for 112 Pulelehua St 5 of 50 Listing Image for 112 Pulelehua St 6 of 50 Listing Image for 112 Pulelehua St 7 of 50 Listing Image for 112 Pulelehua St 8 of 50 Listing Image for 112 Pulelehua St 9 of 50 Listing Image for 112 Pulelehua St 10 of 50 Listing Image for 112 Pulelehua St 11 of 50 Listing Image for 112 Pulelehua St 12 of 50 Listing Image for 112 Pulelehua St 13 of 50 Listing Image for 112 Pulelehua St 14 of 50 Listing Image for 112 Pulelehua St 15 of 50 Listing Image for 112 Pulelehua St 16 of 50 Listing Image for 112 Pulelehua St 17 of 50 Listing Image for 112 Pulelehua St 18 of 50 Listing Image for 112 Pulelehua St 19 of 50 Listing Image for 112 Pulelehua St 20 of 50 Listing Image for 112 Pulelehua St 21 of 50 Listing Image for 112 Pulelehua St 22 of 50 Listing Image for 112 Pulelehua St 23 of 50 Listing Image for 112 Pulelehua St 24 of 50 Listing Image for 112 Pulelehua St 25 of 50 Listing Image for 112 Pulelehua St 26 of 50 Listing Image for 112 Pulelehua St 27 of 50 Listing Image for 112 Pulelehua St 28 of 50 Listing Image for 112 Pulelehua St 29 of 50 Listing Image for 112 Pulelehua St 30 of 50 Listing Image for 112 Pulelehua St 31 of 50 Listing Image for 112 Pulelehua St 32 of 50 Listing Image for 112 Pulelehua St 33 of 50 Listing Image for 112 Pulelehua St 34 of 50 Listing Image for 112 Pulelehua St 35 of 50 Listing Image for 112 Pulelehua St 36 of 50 Listing Image for 112 Pulelehua St 37 of 50 Listing Image for 112 Pulelehua St 38 of 50 Listing Image for 112 Pulelehua St 39 of 50 Listing Image for 112 Pulelehua St 40 of 50 Listing Image for 112 Pulelehua St 41 of 50 Listing Image for 112 Pulelehua St 42 of 50 Listing Image for 112 Pulelehua St 43 of 50 Listing Image for 112 Pulelehua St 44 of 50 Listing Image for 112 Pulelehua St 45 of 50 Listing Image for 112 Pulelehua St 46 of 50 Listing Image for 112 Pulelehua St 47 of 50 Listing Image for 112 Pulelehua St 48 of 50 Listing Image for 112 Pulelehua St 49 of 50 Listing Image for 112 Pulelehua St 50 of 50

$4,900,000

↓ $200,000

Pineapple Hill

112 Pulelehua St, Kapalua

3 Beds 2.5 Baths 4,504 SqFt Residential MLS® # 407964

Days on Market: 140

Listing Image for 116 Pulelehua St 1 1 of 39 Listing Image for 116 Pulelehua St 1 2 of 39 Listing Image for 116 Pulelehua St 1 3 of 39 Listing Image for 116 Pulelehua St 1 4 of 39 Listing Image for 116 Pulelehua St 1 5 of 39 Listing Image for 116 Pulelehua St 1 6 of 39 Listing Image for 116 Pulelehua St 1 7 of 39 Listing Image for 116 Pulelehua St 1 8 of 39 Listing Image for 116 Pulelehua St 1 9 of 39 Listing Image for 116 Pulelehua St 1 10 of 39 Listing Image for 116 Pulelehua St 1 11 of 39 Listing Image for 116 Pulelehua St 1 12 of 39 Listing Image for 116 Pulelehua St 1 13 of 39 Listing Image for 116 Pulelehua St 1 14 of 39 Listing Image for 116 Pulelehua St 1 15 of 39 Listing Image for 116 Pulelehua St 1 16 of 39 Listing Image for 116 Pulelehua St 1 17 of 39 Listing Image for 116 Pulelehua St 1 18 of 39 Listing Image for 116 Pulelehua St 1 19 of 39 Listing Image for 116 Pulelehua St 1 20 of 39 Listing Image for 116 Pulelehua St 1 21 of 39 Listing Image for 116 Pulelehua St 1 22 of 39 Listing Image for 116 Pulelehua St 1 23 of 39 Listing Image for 116 Pulelehua St 1 24 of 39 Listing Image for 116 Pulelehua St 1 25 of 39 Listing Image for 116 Pulelehua St 1 26 of 39 Listing Image for 116 Pulelehua St 1 27 of 39 Listing Image for 116 Pulelehua St 1 28 of 39 Listing Image for 116 Pulelehua St 1 29 of 39 Listing Image for 116 Pulelehua St 1 30 of 39 Listing Image for 116 Pulelehua St 1 31 of 39 Listing Image for 116 Pulelehua St 1 32 of 39 Listing Image for 116 Pulelehua St 1 33 of 39 Listing Image for 116 Pulelehua St 1 34 of 39 Listing Image for 116 Pulelehua St 1 35 of 39 Listing Image for 116 Pulelehua St 1 36 of 39 Listing Image for 116 Pulelehua St 1 37 of 39 Listing Image for 116 Pulelehua St 1 38 of 39 Listing Image for 116 Pulelehua St 1 39 of 39

$4,650,000

↓ $300,000

Pineapple Hill Estates

116 Pulelehua St 1, Kapalua

4 Beds 4.5 Baths 4,081 SqFt Residential MLS® # 406659

Days on Market: 267

Listing Image for 212 Crestview Rd 1 of 50 Listing Image for 212 Crestview Rd 2 of 50 Listing Image for 212 Crestview Rd 3 of 50 Listing Image for 212 Crestview Rd 4 of 50 Listing Image for 212 Crestview Rd 5 of 50 Listing Image for 212 Crestview Rd 6 of 50 Listing Image for 212 Crestview Rd 7 of 50 Listing Image for 212 Crestview Rd 8 of 50 Listing Image for 212 Crestview Rd 9 of 50 Listing Image for 212 Crestview Rd 10 of 50 Listing Image for 212 Crestview Rd 11 of 50 Listing Image for 212 Crestview Rd 12 of 50 Listing Image for 212 Crestview Rd 13 of 50 Listing Image for 212 Crestview Rd 14 of 50 Listing Image for 212 Crestview Rd 15 of 50 Listing Image for 212 Crestview Rd 16 of 50 Listing Image for 212 Crestview Rd 17 of 50 Listing Image for 212 Crestview Rd 18 of 50 Listing Image for 212 Crestview Rd 19 of 50 Listing Image for 212 Crestview Rd 20 of 50 Listing Image for 212 Crestview Rd 21 of 50 Listing Image for 212 Crestview Rd 22 of 50 Listing Image for 212 Crestview Rd 23 of 50 Listing Image for 212 Crestview Rd 24 of 50 Listing Image for 212 Crestview Rd 25 of 50 Listing Image for 212 Crestview Rd 26 of 50 Listing Image for 212 Crestview Rd 27 of 50 Listing Image for 212 Crestview Rd 28 of 50 Listing Image for 212 Crestview Rd 29 of 50 Listing Image for 212 Crestview Rd 30 of 50 Listing Image for 212 Crestview Rd 31 of 50 Listing Image for 212 Crestview Rd 32 of 50 Listing Image for 212 Crestview Rd 33 of 50 Listing Image for 212 Crestview Rd 34 of 50 Listing Image for 212 Crestview Rd 35 of 50 Listing Image for 212 Crestview Rd 36 of 50 Listing Image for 212 Crestview Rd 37 of 50 Listing Image for 212 Crestview Rd 38 of 50 Listing Image for 212 Crestview Rd 39 of 50 Listing Image for 212 Crestview Rd 40 of 50 Listing Image for 212 Crestview Rd 41 of 50 Listing Image for 212 Crestview Rd 42 of 50 Listing Image for 212 Crestview Rd 43 of 50 Listing Image for 212 Crestview Rd 44 of 50 Listing Image for 212 Crestview Rd 45 of 50 Listing Image for 212 Crestview Rd 46 of 50 Listing Image for 212 Crestview Rd 47 of 50 Listing Image for 212 Crestview Rd 48 of 50 Listing Image for 212 Crestview Rd 49 of 50 Listing Image for 212 Crestview Rd 50 of 50

$3,900,000

Pineapple Hill

212 Crestview Rd, Kapalua

3 Beds 3.5 Baths 3,674 SqFt Residential MLS® # 406358

Days on Market: 300

Recent Sales in Pineapple Hill

Sold
Closed: 07/31/2024
Listing Image for 229 Crestview Rd 1 of 40 Listing Image for 229 Crestview Rd 2 of 40 Listing Image for 229 Crestview Rd 3 of 40 Listing Image for 229 Crestview Rd 4 of 40 Listing Image for 229 Crestview Rd 5 of 40 Listing Image for 229 Crestview Rd 6 of 40 Listing Image for 229 Crestview Rd 7 of 40 Listing Image for 229 Crestview Rd 8 of 40 Listing Image for 229 Crestview Rd 9 of 40 Listing Image for 229 Crestview Rd 10 of 40 Listing Image for 229 Crestview Rd 11 of 40 Listing Image for 229 Crestview Rd 12 of 40 Listing Image for 229 Crestview Rd 13 of 40 Listing Image for 229 Crestview Rd 14 of 40 Listing Image for 229 Crestview Rd 15 of 40 Listing Image for 229 Crestview Rd 16 of 40 Listing Image for 229 Crestview Rd 17 of 40 Listing Image for 229 Crestview Rd 18 of 40 Listing Image for 229 Crestview Rd 19 of 40 Listing Image for 229 Crestview Rd 20 of 40 Listing Image for 229 Crestview Rd 21 of 40 Listing Image for 229 Crestview Rd 22 of 40 Listing Image for 229 Crestview Rd 23 of 40 Listing Image for 229 Crestview Rd 24 of 40 Listing Image for 229 Crestview Rd 25 of 40 Listing Image for 229 Crestview Rd 26 of 40 Listing Image for 229 Crestview Rd 27 of 40 Listing Image for 229 Crestview Rd 28 of 40 Listing Image for 229 Crestview Rd 29 of 40 Listing Image for 229 Crestview Rd 30 of 40 Listing Image for 229 Crestview Rd 31 of 40 Listing Image for 229 Crestview Rd 32 of 40 Listing Image for 229 Crestview Rd 33 of 40 Listing Image for 229 Crestview Rd 34 of 40 Listing Image for 229 Crestview Rd 35 of 40 Listing Image for 229 Crestview Rd 36 of 40 Listing Image for 229 Crestview Rd 37 of 40 Listing Image for 229 Crestview Rd 38 of 40 Listing Image for 229 Crestview Rd 39 of 40 Listing Image for 229 Crestview Rd 40 of 40

$6,875,000

Pineapple Hill Estates

229 Crestview Rd, Kapalua

4 Beds 4 Baths 4,598 SqFt Residential MLS® # 400764 Date Sold: July 31, 2024
Sold
Closed: 09/15/2023
Listing Image for 330 Cook Pine Dr 1 of 50 Listing Image for 330 Cook Pine Dr 2 of 50 Listing Image for 330 Cook Pine Dr 3 of 50 Listing Image for 330 Cook Pine Dr 4 of 50 Listing Image for 330 Cook Pine Dr 5 of 50 Listing Image for 330 Cook Pine Dr 6 of 50 Listing Image for 330 Cook Pine Dr 7 of 50 Listing Image for 330 Cook Pine Dr 8 of 50 Listing Image for 330 Cook Pine Dr 9 of 50 Listing Image for 330 Cook Pine Dr 10 of 50 Listing Image for 330 Cook Pine Dr 11 of 50 Listing Image for 330 Cook Pine Dr 12 of 50 Listing Image for 330 Cook Pine Dr 13 of 50 Listing Image for 330 Cook Pine Dr 14 of 50 Listing Image for 330 Cook Pine Dr 15 of 50 Listing Image for 330 Cook Pine Dr 16 of 50 Listing Image for 330 Cook Pine Dr 17 of 50 Listing Image for 330 Cook Pine Dr 18 of 50 Listing Image for 330 Cook Pine Dr 19 of 50 Listing Image for 330 Cook Pine Dr 20 of 50 Listing Image for 330 Cook Pine Dr 21 of 50 Listing Image for 330 Cook Pine Dr 22 of 50 Listing Image for 330 Cook Pine Dr 23 of 50 Listing Image for 330 Cook Pine Dr 24 of 50 Listing Image for 330 Cook Pine Dr 25 of 50 Listing Image for 330 Cook Pine Dr 26 of 50 Listing Image for 330 Cook Pine Dr 27 of 50 Listing Image for 330 Cook Pine Dr 28 of 50 Listing Image for 330 Cook Pine Dr 29 of 50 Listing Image for 330 Cook Pine Dr 30 of 50 Listing Image for 330 Cook Pine Dr 31 of 50 Listing Image for 330 Cook Pine Dr 32 of 50 Listing Image for 330 Cook Pine Dr 33 of 50 Listing Image for 330 Cook Pine Dr 34 of 50 Listing Image for 330 Cook Pine Dr 35 of 50 Listing Image for 330 Cook Pine Dr 36 of 50 Listing Image for 330 Cook Pine Dr 37 of 50 Listing Image for 330 Cook Pine Dr 38 of 50 Listing Image for 330 Cook Pine Dr 39 of 50 Listing Image for 330 Cook Pine Dr 40 of 50 Listing Image for 330 Cook Pine Dr 41 of 50 Listing Image for 330 Cook Pine Dr 42 of 50 Listing Image for 330 Cook Pine Dr 43 of 50 Listing Image for 330 Cook Pine Dr 44 of 50 Listing Image for 330 Cook Pine Dr 45 of 50 Listing Image for 330 Cook Pine Dr 46 of 50 Listing Image for 330 Cook Pine Dr 47 of 50 Listing Image for 330 Cook Pine Dr 48 of 50 Listing Image for 330 Cook Pine Dr 49 of 50 Listing Image for 330 Cook Pine Dr 50 of 50

$6,450,000

Pineapple Hill

330 Cook Pine Dr, Kapalua

4 Beds 4.5 Baths 4,723 SqFt Residential MLS® # 398466 Date Sold: September 15, 2023
Sold
Closed: 05/20/2025
Listing Image for 222 Crestview Rd 1 of 49 Listing Image for 222 Crestview Rd 2 of 49 Listing Image for 222 Crestview Rd 3 of 49 Listing Image for 222 Crestview Rd 4 of 49 Listing Image for 222 Crestview Rd 5 of 49 Listing Image for 222 Crestview Rd 6 of 49 Listing Image for 222 Crestview Rd 7 of 49 Listing Image for 222 Crestview Rd 8 of 49 Listing Image for 222 Crestview Rd 9 of 49 Listing Image for 222 Crestview Rd 10 of 49 Listing Image for 222 Crestview Rd 11 of 49 Listing Image for 222 Crestview Rd 12 of 49 Listing Image for 222 Crestview Rd 13 of 49 Listing Image for 222 Crestview Rd 14 of 49 Listing Image for 222 Crestview Rd 15 of 49 Listing Image for 222 Crestview Rd 16 of 49 Listing Image for 222 Crestview Rd 17 of 49 Listing Image for 222 Crestview Rd 18 of 49 Listing Image for 222 Crestview Rd 19 of 49 Listing Image for 222 Crestview Rd 20 of 49 Listing Image for 222 Crestview Rd 21 of 49 Listing Image for 222 Crestview Rd 22 of 49 Listing Image for 222 Crestview Rd 23 of 49 Listing Image for 222 Crestview Rd 24 of 49 Listing Image for 222 Crestview Rd 25 of 49 Listing Image for 222 Crestview Rd 26 of 49 Listing Image for 222 Crestview Rd 27 of 49 Listing Image for 222 Crestview Rd 28 of 49 Listing Image for 222 Crestview Rd 29 of 49 Listing Image for 222 Crestview Rd 30 of 49 Listing Image for 222 Crestview Rd 31 of 49 Listing Image for 222 Crestview Rd 32 of 49 Listing Image for 222 Crestview Rd 33 of 49 Listing Image for 222 Crestview Rd 34 of 49 Listing Image for 222 Crestview Rd 35 of 49 Listing Image for 222 Crestview Rd 36 of 49 Listing Image for 222 Crestview Rd 37 of 49 Listing Image for 222 Crestview Rd 38 of 49 Listing Image for 222 Crestview Rd 39 of 49 Listing Image for 222 Crestview Rd 40 of 49 Listing Image for 222 Crestview Rd 41 of 49 Listing Image for 222 Crestview Rd 42 of 49 Listing Image for 222 Crestview Rd 43 of 49 Listing Image for 222 Crestview Rd 44 of 49 Listing Image for 222 Crestview Rd 45 of 49 Listing Image for 222 Crestview Rd 46 of 49 Listing Image for 222 Crestview Rd 47 of 49 Listing Image for 222 Crestview Rd 48 of 49 Listing Image for 222 Crestview Rd 49 of 49

$6,205,000

Pineapple Hill Estates

222 Crestview Rd, Kapalua

4 Beds 4.5 Baths 4,265 SqFt Residential MLS® # 405657 Date Sold: May 20, 2025
Sold
Closed: 07/28/2023
Listing Image for 310 Cook Pine Dr 1 of 50 Listing Image for 310 Cook Pine Dr 2 of 50 Listing Image for 310 Cook Pine Dr 3 of 50 Listing Image for 310 Cook Pine Dr 4 of 50 Listing Image for 310 Cook Pine Dr 5 of 50 Listing Image for 310 Cook Pine Dr 6 of 50 Listing Image for 310 Cook Pine Dr 7 of 50 Listing Image for 310 Cook Pine Dr 8 of 50 Listing Image for 310 Cook Pine Dr 9 of 50 Listing Image for 310 Cook Pine Dr 10 of 50 Listing Image for 310 Cook Pine Dr 11 of 50 Listing Image for 310 Cook Pine Dr 12 of 50 Listing Image for 310 Cook Pine Dr 13 of 50 Listing Image for 310 Cook Pine Dr 14 of 50 Listing Image for 310 Cook Pine Dr 15 of 50 Listing Image for 310 Cook Pine Dr 16 of 50 Listing Image for 310 Cook Pine Dr 17 of 50 Listing Image for 310 Cook Pine Dr 18 of 50 Listing Image for 310 Cook Pine Dr 19 of 50 Listing Image for 310 Cook Pine Dr 20 of 50 Listing Image for 310 Cook Pine Dr 21 of 50 Listing Image for 310 Cook Pine Dr 22 of 50 Listing Image for 310 Cook Pine Dr 23 of 50 Listing Image for 310 Cook Pine Dr 24 of 50 Listing Image for 310 Cook Pine Dr 25 of 50 Listing Image for 310 Cook Pine Dr 26 of 50 Listing Image for 310 Cook Pine Dr 27 of 50 Listing Image for 310 Cook Pine Dr 28 of 50 Listing Image for 310 Cook Pine Dr 29 of 50 Listing Image for 310 Cook Pine Dr 30 of 50 Listing Image for 310 Cook Pine Dr 31 of 50 Listing Image for 310 Cook Pine Dr 32 of 50 Listing Image for 310 Cook Pine Dr 33 of 50 Listing Image for 310 Cook Pine Dr 34 of 50 Listing Image for 310 Cook Pine Dr 35 of 50 Listing Image for 310 Cook Pine Dr 36 of 50 Listing Image for 310 Cook Pine Dr 37 of 50 Listing Image for 310 Cook Pine Dr 38 of 50 Listing Image for 310 Cook Pine Dr 39 of 50 Listing Image for 310 Cook Pine Dr 40 of 50 Listing Image for 310 Cook Pine Dr 41 of 50 Listing Image for 310 Cook Pine Dr 42 of 50 Listing Image for 310 Cook Pine Dr 43 of 50 Listing Image for 310 Cook Pine Dr 44 of 50 Listing Image for 310 Cook Pine Dr 45 of 50 Listing Image for 310 Cook Pine Dr 46 of 50 Listing Image for 310 Cook Pine Dr 47 of 50 Listing Image for 310 Cook Pine Dr 48 of 50 Listing Image for 310 Cook Pine Dr 49 of 50 Listing Image for 310 Cook Pine Dr 50 of 50

$6,150,000

Pineapple Hill

310 Cook Pine Dr, Kapalua

3 Beds 3.5 Baths 3,748 SqFt Residential MLS® # 398983 Date Sold: July 28, 2023
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Sold
Closed: 03/07/2025
Listing Image for 306 Cook Pine Dr 73 1 of 46 Listing Image for 306 Cook Pine Dr 73 2 of 46 Listing Image for 306 Cook Pine Dr 73 3 of 46 Listing Image for 306 Cook Pine Dr 73 4 of 46 Listing Image for 306 Cook Pine Dr 73 5 of 46 Listing Image for 306 Cook Pine Dr 73 6 of 46 Listing Image for 306 Cook Pine Dr 73 7 of 46 Listing Image for 306 Cook Pine Dr 73 8 of 46 Listing Image for 306 Cook Pine Dr 73 9 of 46 Listing Image for 306 Cook Pine Dr 73 10 of 46 Listing Image for 306 Cook Pine Dr 73 11 of 46 Listing Image for 306 Cook Pine Dr 73 12 of 46 Listing Image for 306 Cook Pine Dr 73 13 of 46 Listing Image for 306 Cook Pine Dr 73 14 of 46 Listing Image for 306 Cook Pine Dr 73 15 of 46 Listing Image for 306 Cook Pine Dr 73 16 of 46 Listing Image for 306 Cook Pine Dr 73 17 of 46 Listing Image for 306 Cook Pine Dr 73 18 of 46 Listing Image for 306 Cook Pine Dr 73 19 of 46 Listing Image for 306 Cook Pine Dr 73 20 of 46 Listing Image for 306 Cook Pine Dr 73 21 of 46 Listing Image for 306 Cook Pine Dr 73 22 of 46 Listing Image for 306 Cook Pine Dr 73 23 of 46 Listing Image for 306 Cook Pine Dr 73 24 of 46 Listing Image for 306 Cook Pine Dr 73 25 of 46 Listing Image for 306 Cook Pine Dr 73 26 of 46 Listing Image for 306 Cook Pine Dr 73 27 of 46 Listing Image for 306 Cook Pine Dr 73 28 of 46 Listing Image for 306 Cook Pine Dr 73 29 of 46 Listing Image for 306 Cook Pine Dr 73 30 of 46 Listing Image for 306 Cook Pine Dr 73 31 of 46 Listing Image for 306 Cook Pine Dr 73 32 of 46 Listing Image for 306 Cook Pine Dr 73 33 of 46 Listing Image for 306 Cook Pine Dr 73 34 of 46 Listing Image for 306 Cook Pine Dr 73 35 of 46 Listing Image for 306 Cook Pine Dr 73 36 of 46 Listing Image for 306 Cook Pine Dr 73 37 of 46 Listing Image for 306 Cook Pine Dr 73 38 of 46 Listing Image for 306 Cook Pine Dr 73 39 of 46 Listing Image for 306 Cook Pine Dr 73 40 of 46 Listing Image for 306 Cook Pine Dr 73 41 of 46 Listing Image for 306 Cook Pine Dr 73 42 of 46 Listing Image for 306 Cook Pine Dr 73 43 of 46 Listing Image for 306 Cook Pine Dr 73 44 of 46 Listing Image for 306 Cook Pine Dr 73 45 of 46 Listing Image for 306 Cook Pine Dr 73 46 of 46

$5,750,000

Pineapple Hill at Kapalua

306 Cook Pine Dr 73, Kapalua

4 Beds 4.5 Baths 4,150 SqFt Residential MLS® # 401098 Date Sold: March 7, 2025
Sold
Closed: 06/10/2024
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$5,513,000

Pineapple Hill

110 Woodrose Pl Lot 94, Kapalua

3 Beds 3.5 Baths 3,038 SqFt Residential MLS® # 401002 Date Sold: June 10, 2024
Sold
Closed: 06/14/2024
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$4,750,000

Pineapple Hill

238 Crestview Rd, Kapalua

4 Beds 4.5 Baths 4,121 SqFt Residential MLS® # 400594 Date Sold: June 14, 2024
Sold
Closed: 06/27/2023
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$4,400,000

Pineapple Hill

708 Fairway Dr, Kapalua

3 Beds 3.5 Baths 3,238 SqFt Residential MLS® # 398877 Date Sold: June 27, 2023
Sold
Closed: 05/12/2023
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$4,300,000

Pineapple Hill Estates

116 Pulelehua St 1, Kapalua

4 Beds 4.5 Baths 4,081 SqFt Residential MLS® # 396881 Date Sold: May 12, 2023
Sold
Closed: 09/06/2023
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$4,000,000

Pineapple Hill Phase II

105 Pulelehua St, Kapalua

3 Beds 3.5 Baths 3,851 SqFt Residential MLS® # 397856 Date Sold: September 6, 2023
Sold
Closed: 12/15/2025
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$3,850,000

Pineapple Hill

406 Monarch Pl, Kapalua

3 Beds 3 Baths 2,794 SqFt Residential MLS® # 406739 Date Sold: December 15, 2025
Sold
Closed: 08/29/2025
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$3,600,000

Pineapple Hill

214 Crestview Rd, Kapalua

2 Beds 3.5 Baths 2,310 SqFt Residential MLS® # 406502 Date Sold: August 29, 2025
Sold
Closed: 07/20/2023
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$3,550,000

Pineapple Hill

518 Pacific Dr 60, Kapalua

4 Beds 4 Baths 3,357 SqFt Residential MLS® # 398665 Date Sold: July 20, 2023

Be Amazed By Kapalua and Pineapple Hill

No matter the time of day, the views afforded to Pineapple Hill Estates are absolutely dazzling. In the morning, you can bask in the glow of the sunrise while gazing out onto Lanai and Molokai. During the afternoon, you can enjoy the fact that Pineapple Hill is overlooking the world-famous Kapalua Bay Golf Course, one of the best golf courses on Maui, for expansive, unobstructed views. And, saving the best for last, the evening sky is lit up by gorgeous sunsets like fiery paintings each and every day. You will not be able to put a price tag on the fantastic vistas at Pineapple Hill.

As members of the Kapalua Resort, all homeowners are benefitted from the fantastic amenities provided. Perfect for leisure and exercise, the Olympic-sized swimming pool is available for use.

Residents are blessed with the privilege of discounted rates for the two renowned golf courses as well as the excellent tennis courts of which there are ten – both, of course, perfect for practicing your swing. Additionally, not only are you given access to the fabulous features of the pavilion and community, but you are also within walking distance of world-class dining and boutique shopping.

Pineapple Hill Neighborhood Map

Pinneapple Hill Kapalua Map

Construction and History of Pineapple Hill Estates

In the early 1990s, Pineapple Hill Kapalua was recognized as a tropical paradise characterized by raw beauty due to its elevated location. The development of luxury homes began, with an original plan of 99 exclusive homesites for residential use. As of 2001, the 31 residential homesites of Pineapple Hill Estates were annexed into Pineapple Hill in order to enhance the privileges of the community.

Initially, for the development, homesites were a quarter of an acre, with each homeowner given six modern and architecturally crafted floorplans to choose from. Subsequently, however, investors could customize their floorplan if two or more lots were purchased together.

Boasting plots of half an acre, plots at Pineapple Hill Estates grant the freedom to customize floorplans for new homes although only top rows of sites are permitted to have a second story. This has made Pineapple Hill Estates an even more attractive investment in an already striking location.

The Kapalua Real Estate Market | Reflecting Value Money Can't Buy

With its beaches, mountains, and the elegant lifestyle it offers, there is understandably strong value in the luxury neighborhoods of West Maui. While, understandably, recent world events have caused changing market trends. Considering the value retention of property on the land-scarce island of Maui, property in Kapalua has always been a good buy.

Kapalua, which is the greater area surrounding Pineapple Hill, is a wonderful part of the island of Maui with a median house price sitting slightly over $6 million, whereas Pineapple Hill Estates reflect the increased value its location offers at a median house price of $6 million.

Neighboring Napili has a lesser median of just over $1,800,000 but lacks the bountiful advantages Pineapple Hill offers. With its location, quality, and luxurious homes and views, properties for sale in Pineapple Hill boast priceless and as such are expected to maintain strong market value.

The Intersection of Heaven and Earth | Estates in Pineapple Hill

Undeniably, homes at Pineapple Hill and Pineapple Hill Estates are architecturally crafted to bring the absolute best of stylish living to homeowners. Since the location is heaven on earth, the homes bring that same philosophy in design. As mentioned above, homes built in Pineapple Hill Estates have exquisite features, and homes built on the top row often enjoy the privilege of a second story to truly capture the magnificent views.

Pineapple Hill is a residential area and as such the houses are generous and spacious. Most of the homes are held as a fee simple title and are ideal for purchase as a home away from home or for idealized Hawaii living. 

Pineapple Hill Homes for Sale | Beauty in Home and Nature 

West Maui gives its residents an idyllic lifestyle with its pure and unadulterated beaches with world-class surfing, gorgeous ocean vistas, and tropical natural settings but the homes in Pineapple Hill truly offer the best of the best.  Homes here are placed in a dreamlike location where you can experience boutique shopping and exquisite dining one day and then swim in clear blue waters followed by a round of golf at the Bay Course.

Imagine waking up by enjoying a leisurely swim in the resort’s remarkable pool and then being astounded by the natural beauty during a rigorous morning hike. Afterward, you can relax in the afternoon through some games of tennis, or, if you prefer, enjoy the golf courses. At the end of the day, the best of world cuisine is available to you as you bask in a glorious sunset.

Without a doubt, there is so much on offer to you in buying a home on Pineapple Hill you will not want to pass on any opportunity to invest here. For any inquiries please do not hesitate to contact Evan Harlow and view our fabulous properties in Pineapple Hill for sale for yourself.

Get In Touch With Evan!

Evan Harlow Maui

Evan Harlow ranks among the best real estate agents on Maui annually and is in the top 1% of Coldwell Banker agents worldwide in production. Evan has the expertise, experience, and work ethic to help you achieve your real estate buying and selling goals. We promise exceptional service and support from the beginning of the process through closing and beyond. See what Evan's clients are saying on Google.

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