Keewaydin Island Homes for Sale in Naples, Florida | Complete Buyer's Guide

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Keewaydin Island, Naples, Florida

Keewaydin Island is one of Naples, Florida's most exclusive waterfront communities, offering a rare opportunity to own a luxury home surrounded by pristine beaches, natural beauty, and the sparkling waters of the Gulf of Mexico. Accessible only by private boat or water taxi, this secluded barrier island provides an unmatched level of privacy and tranquility while remaining just minutes from downtown Naples and Marco Island.

Homes on Keewaydin Island range from elegant beachfront estates to bayfront residences with private docks and panoramic water views. Residents enjoy a relaxed coastal lifestyle centered around boating, fishing, kayaking, shelling, and wildlife watching, making it an ideal destination for those seeking a peaceful retreat without sacrificing access to world-class dining, shopping, golf, and entertainment.

Real Estate Statistics

Average Price	$555K
Lowest Price	$1.9K
Highest Price	$5.2M
Total Listings	152
Avg. Days On Market	182
Avg. Price/SQFT	$358

Property Types (active listings)

Keewaydin Island Homes for Sale in Naples, FL

• All Listings
• Under $100,000
• $100,000 - $200,000
• $200,000 - $300,000
• $300,000 - $400,000
• $400,000 - $500,000
• $500,000 - $600,000
• $600,000 - $700,000
• $700,000 - $800,000
• $800,000 - $900,000
• $900,000 - $1,000,000
• Over $1,000,000

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$200,000,000

1980 S Ocean Boulevard, Palm Beach

0 Beds 0 Baths 0 SqFt Land / Boat Docks MLS® # R11060793

$100,000,000

204 E Jaffa N,

0 Beds 0 Baths 0 SqFt Commercial MLS® # B26068894

$88,400,000

7 Ocean Lane, Palm Beach

5 Beds 8 Baths 9,410 SqFt Residential MLS® # R11139593

$70,000,000

1355 S Flagler Drive #south Tower Duplex Ph, West Palm Beach

7 Beds 10 Baths 13,904 SqFt Residential MLS® # R11155081

$69,500,000

10203 Collins Avenue #2801, Bal Harbour

6 Beds 8 Baths 8,993 SqFt Residential MLS® # A11931658

$63,500,000

1260 N Lake Way, Palm Beach

6 Beds 8 Baths 7,034 SqFt Residential MLS® # R11133286

$59,000,000

111 Via Del Lago, Palm Beach

9 Beds 12 Baths 12,000 SqFt Residential MLS® # B26077347

$53,900,000

215 Bears Club Drive, Jupiter

6 Beds 12 Baths 15,075 SqFt Residential MLS® # R11168397

$48,000,000

1426 N Ocean Boulevard, Palm Beach

7 Beds 8 Baths 6,747 SqFt Residential MLS® # B26047163

$45,000,000

508 S Beach Road, Jupiter Island

5 Beds 8 Baths 8,551 SqFt Residential MLS® # B26031447

$42,000,000

3501 N Ocean Boulevard, Gulf Stream

5 Beds 8 Baths 5,970 SqFt Residential MLS® # B26019900

$39,500,000

1355 S Flagler Drive #ph 2601, West Palm Beach

4 Beds 6 Baths 8,066 SqFt Residential MLS® # R11128922

New

$38,900,000

13920 Stirling Road, Southwest Ranches

8 Beds 13 Baths 23,442 SqFt Residential MLS® # B26085352

$37,999,998

555 Ocean Boulevard, Golden Beach

8 Beds 11 Baths 9,618 SqFt Residential MLS® # F10539470

$34,000,000

211 Bears Club Drive, Jupiter

5 Beds 8 Baths 10,796 SqFt Residential MLS® # B26080875

$32,000,000

301 Plantation Road, Palm Beach

7 Beds 11 Baths 7,063 SqFt Residential MLS® # B26080140

$30,000,000

209 Commodore Drive, Jupiter

9 Beds 14 Baths 24,320 SqFt Residential MLS® # R11104398

$28,450,000

1355 S Flagler Drive #2203, West Palm Beach

4 Beds 6 Baths 5,743 SqFt Residential MLS® # R11163511

$27,900,000

146 Bears Club Drive, Jupiter

6 Beds 10 Baths 10,401 SqFt Residential MLS® # B26080403

$26,000,000

68 Isla Bahia Drive, Fort Lauderdale

6 Beds 10 Baths 8,327 SqFt Residential MLS® # B26074998

$24,995,000

82719 Old Highway, Islamorada

7 Beds 11 Baths 10,182 SqFt Residential MLS® # A12091663

$24,950,000

2330 Seven Oaks Lane, Palm Beach Gardens

7 Beds 13 Baths 17,440 SqFt Residential MLS® # B26076318

$24,950,000

6001 Le Lac Road, Boca Raton

0 Beds 0 Baths 0 SqFt Land / Boat Docks MLS® # B26070391

$24,950,000

6001 Le Lac Road, Boca Raton

7 Beds 9 Baths 10,914 SqFt Residential MLS® # B26041740

$24,950,000

1100 S Flagler Drive #804, West Palm Beach

4 Beds 6 Baths 4,906 SqFt Residential MLS® # B26033963

$24,900,000

14880 Palmwood Road, Palm Beach Gardens

7 Beds 11 Baths 10,398 SqFt Residential MLS® # B26040641

$24,500,000

Playa Caletas, Canton De Garabito, Puntarenas,

0 Beds 0 Baths 0 SqFt Land / Boat Docks MLS® # B26043539

$23,500,000

5 Grove Isle Drive #phs01, Coconut Grove

4 Beds 6 Baths 7,027 SqFt Residential MLS® # A11989341

$23,500,000

1355 S Flagler Drive #800, West Palm Beach

4 Beds 6 Baths 5,355 SqFt Residential MLS® # B26005870

$23,495,000

5 Via Flagler, Palm Beach

4 Beds 6 Baths 6,437 SqFt Residential MLS® # B26074191

New Open House

$23,000,000

13 Via Vizcaya, Palm Beach

3 Beds 6 Baths 5,913 SqFt Residential

Open House

Thu, Oct 8th, 2026 @ 2pm - 4pm

MLS® # B26085543

$23,000,000

3405 Olde Hampton Drive, Wellington

13 Beds 7 Baths 5,318 SqFt Residential MLS® # R11163167

$23,000,000

369 Eagle Drive, Jupiter

7 Beds 9 Baths 9,692 SqFt Residential MLS® # R11153115

New

$22,900,000

97 Nurmi Drive, Fort Lauderdale

6 Beds 9 Baths 8,600 SqFt Residential MLS® # B26085009

$22,875,000

1355 S Flagler Drive #2301, West Palm Beach

3 Beds 5 Baths 4,613 SqFt Residential MLS® # B26056288

$21,850,000

13614 Rhone Circle, Palm Beach Gardens

6 Beds 10 Baths 10,359 SqFt Residential MLS® # R11135823

$21,500,000

232 Bears Club Drive, Jupiter

5 Beds 8 Baths 8,677 SqFt Residential MLS® # B26022087

$20,000,000

17667 Se Federal Highway, Tequesta

8 Beds 13 Baths 16,134 SqFt Residential MLS® # B26073493

$19,999,999

1015 S Southlake Drive, Hollywood

7 Beds 9 Baths 7,355 SqFt Residential MLS® # A12045486

New

$19,950,000

3723a S Ocean Boulevard, Highland Beach

0 Beds 0 Baths 0 SqFt Land / Boat Docks MLS® # B26085026

New

$19,950,000

3723 S Ocean Boulevard, Highland Beach

6 Beds 10 Baths 8,154 SqFt Residential MLS® # B26085036

New

$19,950,000

409 N Atlantic Drive, Lantana

6 Beds 7 Baths 4,976 SqFt Residential MLS® # B26085270

$19,950,000

2927 Rhone Drive, Palm Beach Gardens

6 Beds 10 Baths 8,417 SqFt Residential MLS® # B26019572

New

$18,950,000

12317 Banyan Road, North Palm Beach

6 Beds 8 Baths 6,313 SqFt Residential MLS® # B26084452

$18,950,000

13771 Le Bateau Isle, Palm Beach Gardens

5 Beds 8 Baths 8,505 SqFt Residential MLS® # B26076191

$18,900,000

13101 Monet Lane, Palm Beach Gardens

7 Beds 9 Baths 12,163 SqFt Residential MLS® # B26075022

$18,850,000

1355 S Flagler Drive #1900, West Palm Beach

3 Beds 5 Baths 4,862 SqFt Residential MLS® # R11062658

$18,595,000

2787 Calais Drive, Palm Beach Gardens

5 Beds 8 Baths 9,272 SqFt Residential MLS® # R11135826

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Keewaydin Island Homes for Sale in Naples, Florida: Complete Buyer’s Guide

Discover Keewaydin Island homes for sale in Naples, Florida. Learn about prices, waterfront living, access, amenities, buying tips, and local real estate insights.

Keewaydin Island Homes for Sale in Naples, Florida Guide

Keewaydin Island is one of Southwest Florida's most exclusive waterfront destinations. Located between Naples and Marco Island, this barrier island offers privacy, natural beauty, and luxury coastal living unlike almost anywhere else in the region.

For buyers seeking a secluded beachfront home with Gulf of Mexico views, boating access, and a peaceful environment, Keewaydin Island presents a rare opportunity. Because the island is accessible only by boat, it attracts homeowners who value privacy and an outdoor lifestyle above traditional neighborhood conveniences.

Why Buyers Choose Keewaydin Island

Keewaydin Island appeals to buyers looking for:

• Direct Gulf-front properties

• Private waterfront estates

• Large lots with exceptional privacy

• World-class boating and fishing

• Unspoiled beaches

• Limited residential development

• A peaceful escape from busy city life

Unlike many luxury communities in Naples, Keewaydin Island remains largely undeveloped, helping preserve its natural environment and exclusive character. More than 80% of the island remains undeveloped, making it one of the area's most distinctive coastal locations.

About Keewaydin Island

Keewaydin Island stretches for approximately eight miles along the Gulf Coast of Southwest Florida. It sits just south of Naples and north of Marco Island.

One of its defining characteristics is that there are no bridges connecting the island to the mainland. Residents and visitors reach their homes by:

• Private boat

• Water taxi

• Personal watercraft

This unique accessibility creates a quiet atmosphere that is difficult to find elsewhere in Naples.

Types of Homes for Sale

Most Keewaydin Island real estate consists of:

Luxury Beachfront Homes

These properties offer:

• Gulf views

• Private beach access

• Expansive outdoor living spaces

• Elevated construction

• Premium finishes

Bayfront Homes

Many buyers prefer bayfront residences because they provide:

• Protected boat docks

• Quick Gulf access

• Waterfront entertaining areas

• Scenic sunrise views

Vacant Waterfront Lots

Occasionally, buyers can purchase land and build a custom coastal home designed around their lifestyle.

Inventory is typically very limited because there are relatively few residences on the island. Recent listings have generally included only one or two active homes at a time, with luxury pricing reflecting the island's exclusivity. 

Current Market Overview

Keewaydin Island is considered a luxury real estate market.

Recent listings have generally ranged from roughly $3 million to nearly $4 million, though prices vary based on location, waterfront frontage, acreage, home size, condition, and private dock access. Inventory is typically very limited due to the small number of homes available.

Market values are influenced by:

• Waterfront location

• Beach frontage

• Lot size

• Boat access

• Home updates

• Hurricane resilience features

Because inventory is low, desirable homes may attract significant buyer interest.

Lifestyle and Amenities

Living on Keewaydin Island focuses on nature rather than commercial amenities.

Residents enjoy:

• Shell collecting

• Paddleboarding

• Fishing

• Kayaking

• Wildlife watching

• Sunset walks

• Boating

Many homeowners appreciate the peaceful setting where traffic noise is replaced by waves and native wildlife.

Waterfront Living

For boating enthusiasts, Keewaydin Island is difficult to match.

Benefits include:

• Deep-water access

• Gulf boating

• Nearby backwater fishing

• Easy access to Naples Bay

• Access to Marco Island waterways

Many homes include:

• Private docks

• Boat lifts

• Outdoor kitchens

• Large covered lanais

• Waterfront entertainment areas

Accessibility

Although the island is private and secluded, it remains close to Naples.

Nearby destinations include:

• Downtown Naples

• Fifth Avenue South

• Third Street South

• Naples Municipal Airport

• Southwest Florida International Airport

Because homes are boat-access only, buyers should consider transportation logistics before purchasing.

Investment Potential

Luxury waterfront property has historically remained desirable because waterfront land is limited.

Keewaydin Island offers several factors that may support long-term demand:

• Limited development

• Scarce inventory

• Unique location

• Premium waterfront views

• Exclusive lifestyle

As with any real estate purchase, future appreciation depends on market conditions, insurance costs, local regulations, and broader economic factors.

Buying Tips

Before purchasing a home on Keewaydin Island, consider:

1. Boat Access

Determine whether you'll keep:

• Your own boat

• A dock on the island

• Mainland marina access

2. Insurance

Request detailed quotes for:

• Flood insurance

• Wind coverage

• Homeowners insurance

3. Property Inspections

Hire professionals experienced with:

• Coastal construction

• Elevated foundations

• Seawalls

• Dock systems

4. Local Regulations

Understand:

• Building requirements

• Environmental regulations

• Coastal permitting

• Dock maintenance responsibilities

5. Work With a Local Luxury Realtor

An experienced Naples waterfront real estate professional can help identify off-market opportunities and navigate the specialized buying process.

Nearby Attractions

Although Keewaydin Island feels remote, residents remain close to many Naples attractions.

Popular nearby destinations include:

• Downtown Naples shopping

• Fine dining

• Championship golf courses

• Naples Botanical Garden

• Art galleries

• Marinas

• Nature preserves

This combination of privacy and convenience is a major reason buyers are drawn to the island.

Frequently Asked Questions

Are homes on Keewaydin Island accessible by car?

No. The island is accessible only by boat or water taxi.

Are there many homes available?

No. Inventory is usually very limited because the island contains relatively few residential properties. 

Is Keewaydin Island a good place for boating?

Yes. It is one of Southwest Florida's premier boating destinations, offering convenient access to both the Gulf of Mexico and surrounding waterways.

Can you build a custom home?

In some cases, vacant waterfront lots become available. Buyers must comply with local building and environmental regulations.

Are the homes luxury properties?

Most residences are considered luxury waterfront homes featuring premium locations and large lots.

Is Keewaydin Island suitable as a second home?

Many owners use their properties as seasonal residences or vacation homes due to the island's private setting and coastal lifestyle.

Conclusion

Keewaydin Island offers one of the most distinctive luxury real estate opportunities in Naples, Florida. With its boat-only access, pristine beaches, limited development, and waterfront homes, it appeals to buyers seeking privacy, natural beauty, and an exceptional coastal lifestyle.

Because available properties are scarce, buyers interested in Keewaydin Island homes for sale should monitor new listings closely and work with a knowledgeable local real estate professional familiar with this unique market.