Buy and hold investments - Winter Park, Florida

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Buy and hold investments - Winter Park, Florida

Eric Boutwell
Denver, CO · Member since 2019 · 4 posts · 3 votes

Hi, my wife and I are looking to buy long term rental properties around Winter Park, FL. Looking around it seems like there are a lot of SFH rentals and a lot for sale as well. Any feedback on this market? Thanks

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Kevin Gidusko
Member since 2019 · 30 posts · 17 votes
6y

@Eric Boutwell, can speak to what I've seen when living near Winter Park, hanging out there for the last 20 years, and now have my step-daughter going to college there: Winter Park is pricey, and has been one of the staid, old money places to be for a long time. About 15 years ago there was more disparity between the uber wealthy and some lower income areas. Gentrification started marching through those neighborhoods and it is about complete by this point. My step-daughter lived on campus the first year, but we now have her in an apartment in Baldwin Park, just to the south. That area is nice and not as pricey (used to be a Naval training base, completely redeveloped about 15 years ago). Winter Park, if you can afford it, is a really lovely place to be with many amenities; a good mix of college student focused shops and some fancy shmancy big name stores. Depending on the price point you're looking for, consider areas to the north that are developing as alternatives to Winter Park: Altamonte Springs, Casselberry, Lake Mary, and especially check out Sanford which is about to go through some good growth-already actually happening. Hope this info helps a little. Give a shout if I can be of any assistance!

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  • Kevin Gidusko
    Member since 2019 · 30 posts · 17 votes
    6y

    @Eric Boutwell, can speak to what I've seen when living near Winter Park, hanging out there for the last 20 years, and now have my step-daughter going to college there: Winter Park is pricey, and has been one of the staid, old money places to be for a long time. About 15 years ago there was more disparity between the uber wealthy and some lower income areas. Gentrification started marching through those neighborhoods and it is about complete by this point. My step-daughter lived on campus the first year, but we now have her in an apartment in Baldwin Park, just to the south. That area is nice and not as pricey (used to be a Naval training base, completely redeveloped about 15 years ago). Winter Park, if you can afford it, is a really lovely place to be with many amenities; a good mix of college student focused shops and some fancy shmancy big name stores. Depending on the price point you're looking for, consider areas to the north that are developing as alternatives to Winter Park: Altamonte Springs, Casselberry, Lake Mary, and especially check out Sanford which is about to go through some good growth-already actually happening. Hope this info helps a little. Give a shout if I can be of any assistance!

    5Reply
  • Michael Stonk
    Member since 2020 · 3 posts · 3 votes
    6y

    Winter Park is really nice. Not sure it's the part of town I'd be going if I was looking for cash flow because it's already heavily developed and super pricey. Altamonte Springs and Maitland are nearby but still have some pockets that are in earlier stages of growth.

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  • Eric Boutwell
    OP
    Denver, CO · Member since 2019 · 4 posts · 3 votes
    6y

    Thanks for the insight, @Kevin Gidusko and @Michael Stonk. You guys hit on what we have been seeing in when we evaluate properties. Rent levels in the area just don't support the housing prices and expenses to have good cashflow. We'll definitly look at these other areas. Thanks again.

    1Reply
  • Kevin Gidusko
    Member since 2019 · 30 posts · 17 votes
    6y

    @Eric Boutwell, probably right-great place if you already had property there as appreciation has been steady with the Metropolitan Orlando market. If you are interested in any of the other places mentioned please let me know. I lived and worked in Central Florida for about two decades, now live in North Florida. Good luck!

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  • Tyler GibsonBusiness Member
    Real Estate Agent · Orlando, FL · Member since 2017 · 1k+ posts · 2k+ votes
    6y

    @Eric Boutwell The other folks in this thread have given you most of the information you need to know about winter park. I would add that if you are looking for a stable long term appreciation purchase then you can't go wrong with winter park. That being said the market in Orlando is very hot right now. Definitely a sellers market. You can still find deals from time to time but they go fast as soon as they go on the market. I am a rental property investor and Realtor here in Orlando so if you ever have any questions about the different areas feel free to reach out. 

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  • Josh Calcanis
    Rental Property Investor · Orlando, FL · Member since 2015 · 131 posts · 62 votes
    6y

    @Eric Boutwell Just to add to some of the areas listed by @Kevin Gidusko I'd throw the Mills50/colonial town north into the mix. I've invested in the UCF area, Thornton Park, and the Mills50 area so far. I found a great deal in the Mills50 area in 2017 and have lived here since then. There are always multis in the area up for sale and with the consistent development in this area you can find a good deal with some upside in a few years if you're planning on house hacking.

    2Reply
  • Kevin Gidusko
    Member since 2019 · 30 posts · 17 votes
    6y

    @Josh Calcanis, excellent additions there. Love the Mills area and Thornton Park is solid. If you haven't been to Bull and Bush definitely check it out-great little pub in an area that used to be run down and is now too sheik for me, but it's still kicking last I saw.

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  • Josh Calcanis
    Rental Property Investor · Orlando, FL · Member since 2015 · 131 posts · 62 votes
    6y

    Thanks @Kevin Gidusko - I haven't been there yet, but I'll add it to the list. I frequent The Guesthouse since I can walk there haha.

    0Reply
  • Eric Boutwell
    OP
    Denver, CO · Member since 2019 · 4 posts · 3 votes
    6y

    Thanks,@Josh Calcanis. I'll look into Thornton Partk and Mills as places to consider as well. I really appreciate all the insight guys. Thanks guys!

    1Reply
  • David PierceBusiness Member
    Property Manager · Deland, FL · Member since 2019 · 74 posts · 28 votes
    6y

    Yep agree with the rest of the gang. I live in Winter Park. Parts of Winter Park are also not part of "The Winter Park" - it is a bigger area then most people think. But the name makes it pricey on the sales side - a lot more than adding income on the rental side.

    PMI Central Florida4.468 Reviews
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