Looking for a good agent in the VA Beach area

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Looking for a good agent in the VA Beach area

Phil Engel
Engineer · Frederick, MD · Member since 2017 · 4 posts · 0 votes

We're looking for a good agent who can help find a great short term vacation rental between $400k-$800k within the oceanfront area. We're specifically looking for single family with two garages that's at most 20 years old, within a half a mile-ish of the beach. I'd love to connect and get to know you and the area more. I moved from Bellingham, WA on the west coast and this beach is a great contender against what I've seen! 

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  • Brooklyn Humphrey
    Santa Rosa Beach, FL · Member since 2026 · 5 posts · 2 votes
    1mo

    Hi Phil, I live in 30A Florida but I do have a great agent I could refer you to. I will send you a direct message.

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    • Phil Engel
      OP
      Engineer · Frederick, MD · Member since 2017 · 4 posts · 0 votes
      1mo
      Quote from @Brooklyn Humphrey:

      Hi Phil, I live in 30A Florida but I do have a great agent I could refer you to. I will send you a direct message.


       Hi Brooklyn, that would me much appreciated, thank you! 

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    • Brooklyn Humphrey
      Santa Rosa Beach, FL · Member since 2026 · 5 posts · 2 votes
      1mo
      Quote from @Phil Engel:
      Quote from @Brooklyn Humphrey:

      Hi Phil, I live in 30A Florida but I do have a great agent I could refer you to. I will send you a direct message.


       Hi Brooklyn, that would me much appreciated, thank you! 


      No problem! Actually, if you want to send me a text at 850.687.0445, I can connect you with her as I don't have direct message abilities on here.
      https://www.30acoastalestates.com/

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  • Michael Eskenasy
    Investor · Pacific Northwest · Member since 2026 · 538 posts · 309 votes
    1mo

    Before you pick the agent, I’d make sure they’re actually underwriting short-term rentals, not just selling beach houses.

    Your buy box is tight enough that I’d want someone who can screen every candidate for STR eligibility, realistic seasonal revenue, flood/insurance exposure, parking and occupancy constraints, and the actual all-in operating number—not just send you MLS listings near the water.

    I’d also have them pressure-test the constraints separately. $400k–$800k, single-family, ≤20 years old, two garages, and roughly a half-mile from the beach may produce a very different inventory depending on which requirement is truly non-negotiable.

    If you want, send me the exact buy box and return target. I can help you tighten the criteria and pressure-test potential properties so you’re comparing them as investments rather than just beach houses.

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  • Diana KhanPro Member
    Attorney · 10451 Mill Run Cir #755 Owings Mills, MD 21117 · Member since 2024 · 577 posts · 198 votes
    1mo
    Quote from @Phil Engel:

    We're looking for a good agent who can help find a great short term vacation rental between $400k-$800k within the oceanfront area. We're specifically looking for single family with two garages that's at most 20 years old, within a half a mile-ish of the beach. I'd love to connect and get to know you and the area more. I moved from Bellingham, WA on the west coast and this beach is a great contender against what I've seen! 

    @Phil Engel, one thing I would add from the legal side is to make sure the short-term rental use is confirmed before you get too far into the deal. I've seen buyers find a property they really like, only to learn later that the way they planned to use it was limited by local rules, an HOA, insurance requirements, or other restrictions.

    For a property like this, I would want enough time in the contract to verify the STR rules, permits, HOA documents if there are any, insurance, and anything else that could affect the rental use. If the whole investment depends on short-term rental income, I would treat that due diligence almost like another contingency. The agent can help point you in the right direction, but I would still independently confirm the legal side before relying on projected STR income.

    [email protected]240-266-0291
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    • Phil Engel
      OP
      Engineer · Frederick, MD · Member since 2017 · 4 posts · 0 votes
      1mo
      Quote from @Diana Khan:
      Quote from @Phil Engel:

      We're looking for a good agent who can help find a great short term vacation rental between $400k-$800k within the oceanfront area. We're specifically looking for single family with two garages that's at most 20 years old, within a half a mile-ish of the beach. I'd love to connect and get to know you and the area more. I moved from Bellingham, WA on the west coast and this beach is a great contender against what I've seen! 

      @Phil Engel, one thing I would add from the legal side is to make sure the short-term rental use is confirmed before you get too far into the deal. I've seen buyers find a property they really like, only to learn later that the way they planned to use it was limited by local rules, an HOA, insurance requirements, or other restrictions.

      For a property like this, I would want enough time in the contract to verify the STR rules, permits, HOA documents if there are any, insurance, and anything else that could affect the rental use. If the whole investment depends on short-term rental income, I would treat that due diligence almost like another contingency. The agent can help point you in the right direction, but I would still independently confirm the legal side before relying on projected STR income.


      Hello Diana,

      Thank you for the heads up! That's really helpful. Do you have a go-to checklist or screening that you review for STRs during the prospect phase? Keeping account of local rules, permits, insurance, and HOA documents are crucial items, I was wondering if there might be any more I'll need to consider in addition to those.

      Do you think that a 60-day window is enough time in the contract for this type of screening? Would we expect to pay any extra, or any expected 'consequences' for extending the contract to give enough time for those things? 

      Then last, I have experience in long-term rental but new to the STR market. Can the four-square method still be a strong starting point to analyze the financials for the property?

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  • Andrew SteffensBusiness Member
    Tampa, FL · Member since 2022 · 3k+ posts · 3k+ votes
    1mo

    Just a tip if you had not found one yet, is to join local host Facebook groups Im sure you will meet some directly and/or get referrals.  Good luck!

    [email protected]813-563-0877
    Vacation Rentals of Florida53 Reviews
    WebsiteView Page
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  • Gregory AcsPro Member
    Lender · MD · Member since 2025 · 226 posts · 87 votes
    1mo

    Sounds like you’ve got a well-defined buy box, which is a great start. As you narrow down properties, I’d also make sure you understand the financing options for short-term rentals and run conservative occupancy and expense assumptions before making an offer. A property that still works with cautious numbers usually makes for a much better long-term investment.

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