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Connor Benn
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House Hacking Duplex in Hillsborough/Pinellas County

Connor Benn
Posted May 4 2023, 18:10

Looking to get into a duplex house hack to kickstart our investment journey!  We'd be going in with an owner occupied loan and so balancing affordability with quality of life is fairly important. What are some areas to look in/avoid?

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Nicole Masters
  • Realtor
  • Sacramento, CA
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Nicole Masters
  • Realtor
  • Sacramento, CA
Replied May 4 2023, 20:11

Hi Connor! I don't know the Florida market, so no specific area suggestions. But I do suggest always looking at the street view on maps when you see a property you think you're interested in. It will help you get familiar quickly with what you are okay with and not okay with!

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Ryan Thomson#1 House Hacking Contributor
  • Real Estate Agent
  • Colorado Springs, CO
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Ryan Thomson#1 House Hacking Contributor
  • Real Estate Agent
  • Colorado Springs, CO
Replied May 5 2023, 08:30

Great idea @Connor Benn ! I'd connect with a house hacking friendly realtor in your area. They can add tremendous value to helping you succeed with your strategy. 

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Laura Shinkle
  • Realtor
  • Charlotte, NC
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Laura Shinkle
  • Realtor
  • Charlotte, NC
Replied May 5 2023, 14:43

Again, not familiar with your area, however, some things to think about: 

1. What's your budget? Talk to a lender (or find a Realtor that can send you one) so you know what your budget is. That may determine location for you. 

2. Talk with a Realtor. If you're looking for something specific, like a multifamily property, then you may be limited to a certain area or price. Some areas don't have duplexes everywhere like they seem to do up north. Charlotte is one of those cities where we really don't have a good supply of them, so the ones that pop up are rare and/or in terrible condition. 

3. What would you be comfortable with if you can't find a duplex to help you achieve the same goal (ie lower your biggest expense which is your living expenses). 

Hope this helps!

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Connor Benn
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Connor Benn
Replied May 5 2023, 18:17
Quote from @Laura Shinkle:

Again, not familiar with your area, however, some things to think about: 

1. What's your budget? Talk to a lender (or find a Realtor that can send you one) so you know what your budget is. That may determine location for you. 

2. Talk with a Realtor. If you're looking for something specific, like a multifamily property, then you may be limited to a certain area or price. Some areas don't have duplexes everywhere like they seem to do up north. Charlotte is one of those cities where we really don't have a good supply of them, so the ones that pop up are rare and/or in terrible condition. 

3. What would you be comfortable with if you can't find a duplex to help you achieve the same goal (ie lower your biggest expense which is your living expenses). 

Hope this helps!


 Hi Laura, 

This is very helpful, I always make a point of going on street view on every potential property I analyze! 

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Laura Shinkle
  • Realtor
  • Charlotte, NC
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Laura Shinkle
  • Realtor
  • Charlotte, NC
Replied May 6 2023, 13:50

That's a good habit! I always try to start with questions, since everyone has different risk tolerance and different views on ROI and investing. Good luck!

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Edward Tindale
  • Lender
  • St. Petersburg, FL
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Edward Tindale
  • Lender
  • St. Petersburg, FL
Replied May 8 2023, 08:33

Hi @Connor Benn, I would recommend reaching out to @Josh Green. He's a knowledgable realtor in the Tampa Bay area!

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Dillon Cook
  • Realtor
  • Tampa, FL
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Dillon Cook
  • Realtor
  • Tampa, FL
Replied May 9 2023, 06:36

You will have some level of difficulty finding a suitable area searching for a duplex. Zoning for multifamily hasn't put them in the most desirable areas and they haven't built a significant amount of new ones in the last 20 years.  Probably better off looking in Pinellas, but I would get a search going and look at everything that comes in on a case by case basis and you'll come across a few pretty quickly.

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Raymond J. Rodrigues
  • Lender
  • Miami, FL
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Raymond J. Rodrigues
  • Lender
  • Miami, FL
Replied May 13 2023, 06:46

Hi @Connor Benn, based on where you’re looking to buy, reach out to @Josh Green. He’s an expert in the area and has helped quite a few of my clients successfully acquire real estate! 

Lender Louisiana (#1039511), Georgia (#1039511), and Florida (#1450514)

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Kristina Kuba
  • Tampa, FL
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Kristina Kuba
  • Tampa, FL
Replied Jun 18 2023, 13:03

@Connor Benn

I highly recommend looking in West Tampa 33607 and Ybor 33605 zip code. You will find lots of older duplexes and sometimes triplexes at a reasonable price compared to multi-family closer to downtown/ south Tampa. As the area develops, West Tampa/ Ybor rents are rapidly increasing.

Plus you will see substantial appreciation after the riverwalk expansion is complete. The 5-mile expansion will allow the Riverwalk to connect more neighborhoods, including West Tampa, Tampa Heights, Bayshore Boulevard, Hyde Park, Riverside Heights, North Franklin Street, and Bowman Heights.



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Joseph Stern
  • Investor
  • Tampa, FL
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Joseph Stern
  • Investor
  • Tampa, FL
Replied Jun 18 2023, 15:56

@Connor Benn Hey Connor, I specialize working with people that want to house hack, I house hack myself. In tampa I would stay west of 275, the east side can be rough in most parts. West tampa, Seminole

Heights, south tampa, and tampa heights would be your best bet. In st Pete I would stay between

1st Ave N and 46th Ave N, jungle terrace is a solid area as well. Largo, Seminole, Clearwater all present opportunity as well. Reach out if you have any questions or need advice!

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Mena Soliman
  • Orange County, CA
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Mena Soliman
  • Orange County, CA
Replied Jun 18 2023, 22:39
Quote from @Joseph Stern:

@Connor Benn Hey Connor, I specialize working with people that want to house hack, I house hack myself. In tampa I would stay west of 275, the east side can be rough in most parts. West tampa, Seminole

Heights, south tampa, and tampa heights would be your best bet. In st Pete I would stay between

1st Ave N and 46th Ave N, jungle terrace is a solid area as well. Largo, Seminole, Clearwater all present opportunity as well. Reach out if you have any questions or need advice!


do these spot cash flow? and how does it look like from a cashflow perspective? if it doesn't cashflow, do you see a market for turning the other unit to a STR/MTR?

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Joseph Stern
  • Investor
  • Tampa, FL
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Joseph Stern
  • Investor
  • Tampa, FL
Replied Jun 19 2023, 07:37
Quote from @Mena Soliman:
Quote from @Joseph Stern:

@Connor Benn Hey Connor, I specialize working with people that want to house hack, I house hack myself. In tampa I would stay west of 275, the east side can be rough in most parts. West tampa, Seminole

Heights, south tampa, and tampa heights would be your best bet. In st Pete I would stay between

1st Ave N and 46th Ave N, jungle terrace is a solid area as well. Largo, Seminole, Clearwater all present opportunity as well. Reach out if you have any questions or need advice!


do these spot cash flow? and how does it look like from a cashflow perspective? if it doesn't cashflow, do you see a market for turning the other unit to a STR/MTR?


Absolutely there are still plenty of opportunities in these areas that cash flow, just a matter of being creative. It can range from $200 a door to $1000+ a door. I would be lying if I said it's as easy as it was a few years ago but still tons of properties that are in the green. St. Pete legally allows you to rent ADU's and Tampa has parts of the city that allow you to Airbnb your ADU, as a whole the Tampa area is relaxed on STR laws. I personally STR/MTR some of my secondary units on airbnb and furnished finder and they are constantly booked. The area still poses amazing opportunity for cash flow, value add, and appreciation.

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Ryan Thomson#1 House Hacking Contributor
  • Real Estate Agent
  • Colorado Springs, CO
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Ryan Thomson#1 House Hacking Contributor
  • Real Estate Agent
  • Colorado Springs, CO
Replied Jun 19 2023, 11:31

@Connor Benn

If the plan is to house hack then here are the priorities in my mind when picking a location:

1.Can you afford to live there?

2. Do you want to live there?

3. In Colorado Springs, I like to find a house that will allow me to rent out bedrooms or create a separate unit.

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Adrian Castillo
  • Real Estate Consultant
  • Brandon, FL
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Adrian Castillo
  • Real Estate Consultant
  • Brandon, FL
Replied Jun 21 2023, 10:32
Quote from @Mena Soliman:
Quote from @Joseph Stern:

@Connor Benn Hey Connor, I specialize working with people that want to house hack, I house hack myself. In tampa I would stay west of 275, the east side can be rough in most parts. West tampa, Seminole

Heights, south tampa, and tampa heights would be your best bet. In st Pete I would stay between

1st Ave N and 46th Ave N, jungle terrace is a solid area as well. Largo, Seminole, Clearwater all present opportunity as well. Reach out if you have any questions or need advice!


do these spot cash flow? and how does it look like from a cashflow perspective? if it doesn't cashflow, do you see a market for turning the other unit to a STR/MTR?


 I will say, do your homework some locations have city and county limits that prohibit SRTs and MTRs. Send me a DM to further discuss strategies.