Oyster Bay Homes for Sale in Naples, Florida: Waterfront Living Guide

^{Waterfront Living, Boating Access, and Coastal Elegance Near Downtown Naples}

Oyster Bay, Naples, Florida

Discover Oyster Bay, one of Naples, Florida’s desirable waterfront communities offering a relaxed coastal lifestyle with convenient access to boating, beaches, dining, and downtown attractions. Oyster Bay homes for sale feature a variety of residences, including waterfront properties, canal-front homes, and custom residences designed for comfortable Southwest Florida living.

Known for its scenic waterways, private docks, tropical landscaping, and peaceful residential atmosphere, Oyster Bay is ideal for buyers seeking a Naples home with both waterfront charm and everyday convenience. Residents enjoy easy access to Naples Bay, Gulf Coast beaches, shopping destinations, restaurants, golf courses, and recreational activities.

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)

Oyster Bay 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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Oyster Bay Homes for Sale in Naples, Florida: Buyer's Guide

Explore Oyster Bay homes for sale in Naples, Florida. Learn about home styles, amenities, pricing factors, and tips for buying in this desirable waterfront community.

Oyster Bay Homes for Sale in Naples, Florida

If you're searching for Oyster Bay homes for sale in Naples, Florida, you'll find a waterfront community that combines coastal living with convenient access to downtown Naples. Known for its boating opportunities, scenic canals, and proximity to the Gulf of Mexico, Oyster Bay attracts buyers seeking a relaxed Southwest Florida lifestyle.

Whether you're looking for a primary residence, vacation home, or investment property, Oyster Bay offers a variety of housing options within minutes of Naples' beaches, shopping, and dining.

Why Buyers Choose Oyster Bay

Oyster Bay is one of Naples' established waterfront neighborhoods, offering residents direct or near-direct boating access to Naples Bay and the Gulf of Mexico. Many homes feature private docks, canal views, or easy access to marinas, making the community especially appealing to boating enthusiasts.

Additional reasons buyers choose Oyster Bay include:

• Established residential streets

• Mature tropical landscaping

• Convenient location near downtown Naples

• Access to boating and fishing

• Short drive to Gulf beaches

• Variety of home styles and price points

The combination of waterfront living and city convenience makes Oyster Bay attractive to retirees, seasonal residents, professionals, and second-home buyers alike.

Types of Homes Available

One of the advantages of Oyster Bay is the diversity of available properties. Depending on current market inventory, buyers may find:

• Waterfront single-family homes

• Canal-front residences with private docks

• Renovated ranch-style homes

• Contemporary custom homes

• Condominiums

• Villas and attached residences

• Investment and seasonal properties

Many homes feature:

• Open floor plans

• Outdoor entertaining spaces

• Swimming pools

• Boat lifts

• Modern kitchens

• Covered lanais

• Spacious garages

Inventory changes throughout the year, giving buyers opportunities across a range of property sizes and architectural styles.

Home Prices and Market Trends

Home prices in Oyster Bay vary based on several factors, including:

• Waterfront location

• Canal frontage

• Boat dock availability

• Home size

• Lot dimensions

• Renovations and upgrades

• Water access

• Overall market conditions

Properties with direct Gulf access and private docks generally command higher prices than inland homes.

Because Naples remains a desirable destination for both full-time and seasonal residents, the local real estate market can experience changing inventory levels throughout the year. Working with a knowledgeable local real estate professional can help buyers identify opportunities quickly.

Waterfront Lifestyle

Living in Oyster Bay means embracing the Southwest Florida boating lifestyle.

Many homeowners enjoy:

• Morning boat rides

• Sunset cruises

• Deep-sea fishing

• Paddleboarding

• Kayaking

• Waterfront dining by boat

• Dolphin and bird watching

For boating enthusiasts, having convenient water access can be one of the community's biggest advantages.

Beyond boating, residents appreciate the peaceful canals, waterfront scenery, and tropical atmosphere that define Oyster Bay.

Amenities and Recreation

Although Oyster Bay is primarily a residential community, residents enjoy convenient access to many recreational opportunities throughout Naples.

Popular activities include:

• Public beaches

• Golf courses

• Tennis and pickleball facilities

• Parks and nature preserves

• Walking and biking paths

• Art galleries

• Farmers markets

• Community events

• Waterfront restaurants

Naples is well known for its outdoor lifestyle, making it easy to enjoy Florida's warm weather throughout much of the year.

Shopping and Dining Nearby

Oyster Bay's location places residents close to many shopping and dining destinations.

Nearby conveniences often include:

• Grocery stores

• Boutique shopping

• Local cafés

• Seafood restaurants

• Fine dining

• Coffee shops

• Medical offices

• Banks

• Fitness centers

Downtown Naples offers a mix of upscale shopping, entertainment, and waterfront dining that appeals to both residents and visitors.

Schools and Healthcare

Families considering Oyster Bay benefit from access to educational opportunities and healthcare services throughout Naples.

Nearby resources include:

• Public schools

• Private schools

• Early learning centers

• Colleges and continuing education

• Medical specialists

• Urgent care facilities

• Hospitals

• Wellness centers

The area also offers numerous community resources that support year-round residents and seasonal homeowners alike.

Buying a Home in Oyster Bay

Before purchasing a home in Oyster Bay, consider several important factors:

Waterfront Access

Not every property offers the same boating access. Buyers should understand canal depth, bridge clearance, dock features, and navigation routes if boating is a priority.

Home Inspections

An inspection can help evaluate:

• Roof condition

• HVAC systems

• Plumbing

• Electrical systems

• Foundation

• Seawalls

• Docks

• Boat lifts

Insurance Considerations

Insurance costs may vary depending on:

• Flood zone designation

• Wind mitigation features

• Property age

• Construction type

• Waterfront location

Reviewing insurance options early in the buying process can help you estimate ongoing ownership costs.

Financing

Buyers should obtain mortgage pre-approval before beginning their home search. Being financially prepared can strengthen your offer in a competitive market.

Work with a Local Expert

An experienced Naples real estate professional can provide valuable insight into neighborhood trends, comparable sales, waterfront considerations, and available listings.

Frequently Asked Questions

Are Oyster Bay homes waterfront?

Many homes in Oyster Bay offer canal frontage or waterfront locations, though not every property has direct water access. Available features vary by home.

Is Oyster Bay a good place for boat owners?

Yes. Oyster Bay is known for its boating lifestyle, and many properties include private docks or convenient access to nearby marinas.

How close is Oyster Bay to downtown Naples?

Oyster Bay is located just minutes from downtown Naples, providing convenient access to shopping, dining, entertainment, and Gulf Coast beaches.

What types of homes are available?

Buyers may find single-family homes, waterfront residences, condominiums, villas, and renovated properties, depending on current market availability.

Is Oyster Bay suitable for seasonal residents?

Yes. Many buyers choose Oyster Bay as a seasonal retreat because of its waterfront lifestyle, warm climate, and proximity to local attractions.

What should buyers consider before purchasing?

Evaluate waterfront access, property condition, insurance requirements, financing, and local market trends before making an offer.

Conclusion

Oyster Bay offers an appealing blend of waterfront living, boating access, and proximity to everything Naples has to offer. From canal-front homes with private docks to comfortable residences close to beaches and downtown attractions, the neighborhood provides options for a variety of lifestyles and budgets.

If you're exploring Oyster Bay homes for sale in Naples, Florida, taking the time to understand the community, current market conditions, and waterfront features can help you make a well-informed decision and find a property that meets your long-term goals.