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Property Managers in Winter Park, FL

13 investor-friendly Property Managers found in Winter Park, FL as of January 10, 2026

  • business profile image

    Dwell

    Short-term rental: less than 30 days

    4.7 stars
    39 Reviews
    21 forum posts

    Short-term rental: less than 30 days

    Without any commitments, we'll provide you with a vacation rental assessment upfront that might save you money. So that you know we have skin in the game, we provide a two month guarantee. If after two months you're unsatisfied, we'll refund our commission. As Vacation Rental Consultants, we create custom built agreements for each individual owner depending on their needs. Often we support existing owners who: - Are frustrated with not earning enough money from their property -... view more
  • business profile image

    Berger Realty & Investments, Inc

    Long-term rental: 12+ months

    5.0 stars
    14 Reviews
    1 forum post

    Long-term rental: 12+ months

    With nearly a decade of experience, we partner with owners and investors to optimize property value and minimize the complexities of day-to-day management. We handle the mess, so you stress less. We manage each property as a strategic asset, providing honest insights on enhancements to boost ROI and a hands-on approach to drive your investment’s success. Transparency and integrity are the cornerstones of my service. We believe in building long-lasting partnerships, offering responsive comm... view more
  • business profile image

    HomeRiver Group

    Long-term rental: 12+ months

    5.0 stars
    162 Reviews

    Long-term rental: 12+ months

    To help real estate investors like you succeed, we charge owners ZERO management fees for 12 months with a 2-year contract. HomeRiver Group’s mission is to be the premier national residential property management company in the United States, offering acquisition, renovation, leasing, management, maintenance and brokerage. We are intently focused on serving both owners and tenants, and are dedicated to a culture of integrity, superlative performance and respect. view more
Showing 11 - 13 of 13 Winter Park Property Managers