Oyster Bay Real Estate

About Oyster Bay

Oyster Bay is a Southwest Florida community in Naples where the NABOR MLS currently shows 5 active listings, asking $1,499,000 to $7,995,000, averaging 67 days on market, with 2 closed sales recorded here in the last 90 days. Waterfront Realty Group, Inc. has worked this market as an independent, Realtor-owned brokerage since 1986, and pairs every customer with a Sales Associate who knows these streets, waterways, and price trends firsthand.

Figures reflect the active Oyster Bay inventory shown on this page, drawn live from the Naples Area Board of REALTORS® (NABOR) MLS. Closed-sale counts cover the trailing 90 days.

$7,995,000

1085 SANDPIPER ST

5 bd · 5.5 ba · 4,400 sf

Listing courtesy of John R Wood Properties

Source: NABOR MLS

$3,899,000

1510 Chesapeake AVE

3 bd · 3.5 ba · 3,062 sf

Listing courtesy of Compass Florida LLC

Source: NABOR MLS

$3,095,000

1420 Jewel Box AVE

3 bd · 3 ba · 2,585 sf

Listing courtesy of Premiere Plus Realty Company

Source: NABOR MLS

$2,700,000

1630 Chesapeake AVE

4 bd · 3 ba · 2,150 sf

Listing courtesy of Compass Florida LLC

Source: NABOR MLS

$1,499,000

1390 Chesapeake AVE 1390

3 bd · 2 ba · 1,795 sf

Listing courtesy of Coldwell Banker Realty

Source: NABOR MLS

Listing data provided via the Naples Area Board of REALTORS® (NABOR) MLS. Information deemed reliable but not guaranteed. Equal Housing Opportunity. © 2026 Waterfront Realty Group, Inc. License CQ257718. All rights reserved.