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Property Managers in Windermere, FL

Compare top property management companies in Windermere, FL. Review services and vetting status, then reach out or request a free quote.

IRM Investments
Maggie Senior
Orlando, FL [ Serves Miami, Orlando, Sanford, Clermont +5 more ]
Verified & Vetted Long-term Residential
We specialize in Orlando homes, townhomes, condos and commercial properties. Call us with all your Central Florida rentals and property management needs.
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R.Russell Properties, Inc.
Mark C. Pagdin REALTOR, NARPM
Altamonte Springs, FL [ Serves Tampa, Orlando, Deltona, Kissimmee +14 more ]
Multi-Agent Team
Who is Russell Properties, Inc.? R. Russell Properties, Inc. is "Central Florida's Choice. With the same owner, in the same location, it's been a central Florida choice for twenty six years. Who are we? We are a family-oriented, full service-based real estate company that specializes in property management, sales and investments. Robert C. Russell is the principal owner and broker and has been in the real estate industry in Florida since 1978. As experienced Realtors, Rob Russell and the members of his staff are qualified to provide the professional real estate services needed to manage, lease, buy, or sell your real estate investment. Our clients enjoy a wide range of services and benefit from our many years of experience in marketing, negotiating, financing and contracts. We are committed to providing prompt, personal service. Our goal is to treat each investment property, each owner and tenant simply with the individual care and attention they deserve. We have extensive knowledge of the Florida and Central Florida area and offer our clients the finest in professional, reliable service. Russell Properties has grown into an industry leader by providing our clients with the highest caliber of service, strong attention to detail , state of the art management techniques and highly competitive pricing. Our staff of 10 professionals have served and assisted thousands of satisfied owners, tenants and clients, some whom have been with us for over 20 years. Please check us out at: www.russellproperties.com
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Allegiant Management Group
Maria Napolitano
Kissimmee, FL [ Serves Orlando, Kissimmee, Apopka, Sanford +9 more ]
Long-term Residential
Advanced Management Specialists provides superiorproperty management servicesthroughout theCentral Florida area. We are the leader in helping owners reach their investment property goals, as well as providing renters with the best possible choice in housing. We are ready and dedicated to take care of all your property management, rental, and sales needs. Our staff consists of qualified, highly trained professionals committed to excellence in customer service. From our front office staff, to our maintenance crew, as well as our dedicated property supervisors, accountants, and management personnel, we will handle any and all property management concerns with your peace of mind as our primary goal. Stop in and see why we are the premier property management company in Central Florida. Our office is conveniently located in the heart of Kissimmee close to major highways which gives usthe ability to easilyaccess to any part of Central Florida.
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Realty10
Joseph Haddad
Windermere, FL
Long-term Residential
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Rental market in Windermere: rising rents

In Windermere, Census median gross rent rose about 46.1% over the last five years, rents on a clear upward path. The same data shows three-bedroom rents about 36% above the U.S. average, a population of 1,471,937, up 9.1% over five years, and renters in 43.2% of homes. The typical home is valued near $390,100, and the median household earns about $79,719 a year, with renters spending a median 34.8% of income on rent.

Market at a glance

Rents & affordability

+40% 2-bed vs U.S. rent
+36% 3-bed vs U.S. rent
+41% 4-bed vs U.S. rent
+46.1% Rent trend, 5-yr
34.8% Rent-to-income

People & households

43.2% Renter-occupied
1,471,937 Population
+9.1% Population, 5-yr
$79,719 Median household income

Housing stock

10.1% Vacancy rate
$390,100 Median home value
1994 Median year built
61.7% Single-family homes

Jobs

4.6% Unemployment rate
Rent vs the U.S. average, by bedroom size
U.S. average 2-bed +40% 3-bed +36% 4-bed +41%
Who rents vs owns
Renters 43.2% Owners 56.8%

Professional property management in Windermere typically covers pricing, listings, tenant screening, rent collection, and repairs. About 61.7% of local housing is single-family, a common focus for rental owners. With vacancy near 10.1%, rent positioning and days on market can shape your return. Area unemployment is 4.6% as of July 2026. Browse the managers here and request pricing.

Pricing shown is long-term residential, not short-term or vacation. Non-residential and commercial rents follow the same local direction as a rule, so the residential deviations above give you a fair read.

Frequently asked questions

Are rents rising in Windermere?

In the past five years, Census median gross rent rose close to 46.1%.

How do rents in Windermere compare to the national average?

Measured against the U.S. average: two-bedroom +40%, three-bedroom +36%, four-bedroom +41%. Each figure compares a bedroom size to the typical U.S. rent, not a rent we set.

Is Windermere a good market for rental property?

Tenants have options here, so pricing and low turnover matter. Renters make up 43.2% of households and vacancy sits near 10.1%. Three-bedroom rents run about 36% above the national average, and rents rose about 46.1% over five years.

How strong is rental demand in Windermere?

Renters make up 43.2% of the housing, and the population of 1,471,937 grew 9.1% over five years. Vacancy runs near 10.1%.

Rent shown as a deviation from the typical U.S. rent, a national average weighted by renter population, from HERO and HUD reference data. Demographics, population, and rent trend from the U.S. Census Bureau ACS 2020-2024 5-year estimates at the county level, with the five-year trend measured against the 2015-2019 estimates. Unemployment from the U.S. Bureau of Labor Statistics (July 2026).