Should I sell or should I hold?

[Paul Ricci Jr]

Hey everyone, I had a question about when / is there a good time to cash out on a rental property to then leverage that into a better situation or multiple new builds. 

I purchased and lived in my first duplex about 5 years ago. I paid $166,000 for it and collected rent while I lived for in the other side. The market is hot right now (North East FL, just north of Daytona Beach) and me and my family just build a new home. I'm confident I could get $350,000 (for the sake of discussion lets roll with that). The units are in great shape, newer AC units (3 and 4 yrs old) and a new roof (1 year old) built in 2004.

The house is now paid off and renting for $1,400 (each side) which is great. Lots of people are moving into this area and there is a new house being built on every street, new apartments and many old folks homes.

My question is, wouldn't it make sense to sell now, make $184,000 profit free from capital gains and reinvest in something bigger? I would be able to build 2 new duplexes with that $184,000 in this area plus have my initial $166,000.

Any thoughts would be appreciated! I'm 27 and enjoy real-estate so I'm looking for ways to move up and leverage my equity to acquire another multifamily. I own a duplex zoned lot as well so the new build would be ready to go (275K for a 3/2 duplex in this area) + land. 

Or would a HELOC make more sense to fund a new build?

I appreciate your thoughts in advance!