Serving Windermere, FL & the Butler Chain of Lakes
Windermere Property Management
The Listing Real Estate Management is a full-service Windermere property management company. We lease, manage, and maintain single-family homes, townhomes, condos, and multifamily rentals across the Town of Windermere and the neighborhoods that share its 34786 ZIP code. Hospitality is built into everything we do, so owners get a local team that picks up the phone and residents who are happy to renew. Whether your rental is near the Butler Chain of Lakes, close to Dr. Phillips, or anywhere between Windermere, Winter Garden, and Orlando, our Windermere property managers are ready to protect your investment. Start with a free, in-depth rental analysis to see what your home should rent for.
How Much Can I Get for Rent?The Best Windermere Property Management Company
We offer full-service property management in Windermere, FL with a personal, proactive approach to residential management. Every owner gets a dedicated, licensed property manager who knows the home, the neighborhood, and the people living there.
Most homes with a Windermere address actually sit outside the small town limits, in neighborhoods around the Butler Chain of Lakes and along the roads toward Dr. Phillips and Winter Garden. Our team has managed Central Florida rentals for more than 15 years. On average, the homes we market lease in under 30 days, and we charge just two fees for full-service management. You'll notice the difference in the first month.
Talk to a Windermere property manager: 407-792-5900What Do We Do as Your Windermere Property Managers?
Owning a rental property in Windermere, Florida can be an excellent investment. Renters here want lake views, quiet tree-lined neighborhoods, and quick access to Dr. Phillips, the theme parks, and downtown Orlando. But the wrong property management company can turn a good Windermere rental into an expensive headache. Here's how we protect our owners.
Property Management 1: Marketing & Leasing
01. Professional photos, video tours, and drone photography for every home we manage.
02. Maximum exposure: your Windermere rental is listed on 250+ rental websites.
03. Showings 7 days a week. On average, our homes lease in under 30 days.
Property Management 2: Tenant Screening
01. A thorough screening process that finds responsible, qualified residents for long-term rental success.
02. Every applicant is checked for credit history, debt-to-income ratio, nationwide evictions, criminal background, income and employment, and two years of rental history.
03. We'd rather wait a few extra days for the right tenant than rush in the fast one.
Property Management 3: Rent Collection
01. Rent collection that's simple and efficient for owners and residents.
02. Residents pay rent online through their resident portal, 24/7/365.
03. You get paid faster. Owner draws go straight to your bank account by direct deposit.
Property Management 4: Maintenance & Repairs
01. Fast, quality maintenance that protects your Windermere rental property.
02. A 24/7 emergency maintenance line, so your home is covered around the clock.
03. Licensed, bonded, and insured local vendors, billed at cost with no upcharge or added maintenance fees.
Property Management 5: Rental Property Accounting
01. Your property manager tracks your Windermere rental's financials every month.
02. Detailed monthly owner statements prepared by a professional bookkeeper.
03. Statements show income, expenses, liabilities, and equity, and you get a year-end 1099 at tax time.
Property Management 6: Rental Management Guarantees
01. Our 12-Month Tenant Guarantee: if a tenant we screened, approved, and managed moves out before their one-year lease ends, we'll find a new tenant free of charge.
02. Our satisfaction guarantee: if you're not happy with our service for any reason, cancel anytime with 30 days' written notice. We won't hold you hostage.
What Types of Rental Properties Do We Manage in Windermere and Central Florida?
Our Windermere property management company specializes in residential rentals throughout Windermere, southwest Orange County, and Greater Orlando.
Single-Family Home Property Management in Windermere
We call Central Florida home, and as a boutique property management company, we take pride in knowing every single-family home we manage. Windermere-area rental homes range from older lakefront houses along the Butler Chain to newer neighborhoods off Winter Garden Vineland Road and SR 429. Whatever you own, we'll keep it maintained and earning for as long as we manage it.
Townhome & Condo Property Management in Windermere, Florida
Our rental property managers are experts in townhome and condominium management, including the HOA and association rules that come with most Windermere-area communities, many of them gated. Owning a Windermere investment property should be a pleasant and profitable experience, and we handle the details that keep it that way.
Apartment & Multifamily Property Management in Windermere
We offer full-service apartment and multifamily property management in Windermere and throughout Central Florida. Duplexes, small apartment buildings, and larger communities all need an experienced team for leasing, maintenance, and financial reporting. That's where our years of multifamily experience pay off for you and your rental property.
What Central Florida Rental Owners Say About The Listing
I left a larger property management company and thankfully found The Listing Orlando. Jobe with The Listing Real Estate Management is phenomenal. They are responsive and extremely quick to address items with my rental property. The Listing is creative in getting rental properties rented, even in out of season times. I am most thankful for their follow through; They don’t need to be asked to complete something or to follow up with a tenant or vendor. I recommend The Listing constantly to anyone looking for property management.
Courtney R.
Rental Property Owner
Award-Winning Windermere Property Management
We're proud to be a trusted source for Windermere property management services. With more than 15 years of property management experience behind us, you can feel at ease knowing every part of your Windermere rental property is protected. The Listing Real Estate Management is a licensed Florida real estate brokerage (CQ1056007), and our team belongs to the National Association of Residential Property Managers (NARPM), the Institute of Real Estate Management (IREM), the Orlando Regional REALTOR® Association, and the National Association of REALTORS®.
As a leading property management company in Orlando and Central Florida, we were named Silver, Best Property Management Company in the Orlando Sentinel's Central Florida Favorites (2025 and 2026), voted #3 Best Property Management Company in Orlando by Rentce, listed among the Best Professional Property Management Companies in Orlando by Roofstock, and named a Top Property Management Company in Orlando by Expertise.
About Windermere, Florida
Windermere, Florida is a small Orange County town about 15 miles west of downtown Orlando. Incorporated in 1925, it sits on a strip of land between Lake Down and Lake Butler in the Butler Chain of Lakes, and its motto is "Among the Lakes." Dirt side streets, roundabouts, and a heavy tree canopy give the town a quiet, rural feel, even though Dr. Phillips, Winter Garden, and the theme parks are a short drive away. Nearby communities include Isleworth and Keene's Pointe.
The Town of Windermere had just over 3,000 residents at the 2020 Census, but the 34786 ZIP code covers a much larger area of neighborhoods with Windermere addresses. Renters include families who want space and lake access, professionals relocating to Orlando, and people who work in Dr. Phillips and the tourism corridor. Well-kept homes that are priced right don't sit long here.
Allow The Listing Real Estate Management to be your boutique Windermere property management service provider. We strive to provide the best property management services to the owners and residents of Windermere, and our goal is to manage every part of your Windermere rental property effectively and efficiently.
We also manage rentals in nearby Winter Garden, Dr. Phillips, and Clermont.
Windermere Property Management FAQs
Straight answers to the questions Windermere rental owners ask us most.
How much does property management cost in Windermere, FL?
The Listing charges two fees for full-service property management in Windermere: a leasing fee of 75% of one month's rent when we place a tenant, and a monthly management fee of 8–10%. There are no setup fees and no renewal fees. Owners with multiple properties or units can ask about our TL Investor Rate. See full pricing.
What does a Windermere property manager do?
A full-service Windermere property manager handles the day-to-day work of owning a rental home. At The Listing, that includes pricing and marketing your property, showings, tenant screening, lease preparation and signing, move-in inspections, rent collection, maintenance and 24/7 emergency repairs, lease enforcement, routine inspections, monthly owner statements, and a year-end 1099.
How long does it take to rent a house in Windermere?
On average, the homes we manage lease in under 30 days. We list every rental on 250+ websites with professional photos and a virtual tour, and we show homes 7 days a week. Price, condition, and time of year all affect how fast a home rents, which is why every owner starts with a free rental analysis.
How much rent can I get for my Windermere home?
It depends on size, location, condition, and the community. Windermere rents range widely, from townhomes to lakefront estates, and there isn't enough public listing data for a reliable average. For context, Rentometer's October 2026 data put Orlando's citywide average three-bedroom rent around $2,600, and larger Windermere homes typically rent above that. For a number specific to your property, request a free rental analysis.
What areas around Windermere do you serve?
We manage rental properties throughout the Town of Windermere and the 34786 ZIP code, along with Winter Garden, Dr. Phillips, Clermont, Orlando, and the rest of Central Florida. Our office is at 300 S Orange Ave #1000 in downtown Orlando, and office visits are by appointment.
Can I cancel my property management agreement?
Yes. If you're not happy with our service for any reason, you can cancel with 30 days' written notice. We also back our placements with a 12-Month Tenant Guarantee: if a tenant we screened, approved, and managed moves out before the end of their one-year lease, we'll find a new tenant free of charge.
Is Windermere a good place to own a rental property?
For a lot of investors, yes. Windermere-area homes attract long-term renters who want space and lake access, there's very little room for new homes inside the town itself, and Dr. Phillips and the theme parks are close by. Like any market, your results depend on buying the right home at the right price and managing it well.
Ready to Have Your Windermere Rental Property Managed by The Listing?
Tell us about your Windermere rental and a local property manager will reach out. Prefer to talk now? Call 407-792-5900.
"*" indicates required fields