Serving Winter Garden, FL & West Orange County
The Listing Real Estate Management is a full-service Winter Garden property management company. We lease, manage, and maintain single-family homes, townhomes, condos, and multifamily rentals across Winter Garden and the rest of West Orange County. 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 a few blocks from Plant Street, in one of the newer neighborhoods off SR 429, or anywhere between Winter Garden, Windermere, and Orlando, our Winter Garden 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?We offer full-service property management in Winter Garden, 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.
Winter Garden has more than tripled in population since 2000, and we've watched its rental market grow right along with it. 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 Winter Garden property manager: 407-792-5900Owning a rental property in Winter Garden, Florida can be an excellent investment. Renters here want to be close to downtown and the West Orange Trail, with SR 429 and Florida's Turnpike a few minutes away. But the wrong property management company can turn a good Winter Garden rental into an expensive headache. Here's how we protect our owners.
01. Professional photos, video tours, and drone photography for every home we manage.
02. Maximum exposure: your Winter Garden rental is listed on 250+ rental websites.
03. Showings 7 days a week. On average, our homes lease in under 30 days.
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.
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.
01. Fast, quality maintenance that protects your Winter Garden 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.
01. Your property manager tracks your Winter Garden 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.
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.
Our Winter Garden property management company specializes in residential rentals throughout Winter Garden, West Orange County, and Greater Orlando.
We call Central Florida home, and as a boutique property management company, we take pride in knowing every single-family home we manage. Winter Garden's rental homes range from older houses near the historic downtown to newer construction in the neighborhoods off SR 429. Whatever you own, we'll keep it maintained and earning for as long as we manage it.
Our rental property managers are experts in townhome and condominium management, including the HOA and association rules that come with many newer Winter Garden communities. Owning a Winter Garden investment property should be a pleasant and profitable experience, and we handle the details that keep it that way.
We offer full-service apartment and multifamily property management in Winter Garden 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.
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
We're proud to be a trusted source for Winter Garden property management services. With more than 15 years of property management experience behind us, you can feel at ease knowing every part of your Winter Garden 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.
Winter Garden, Florida sits on the south shore of Lake Apopka in west Orange County, about 14 miles west of downtown Orlando. The city grew up around citrus and the railroad, and its motto, "Where Good Things Grow," still fits. Historic downtown centers on Plant Street, where the Garden Theatre, the Plant Street Market food hall, and the West Orange Trail all sit within a few blocks. The Winter Garden Farmers Market runs downtown every Saturday morning, and American Farmland Trust has recognized it as one of the best farmers markets in the country. SR 50, SR 429, and Florida's Turnpike put the rest of Orlando and the theme parks within an easy drive.
Winter Garden's rental market is strong. The population grew from about 14,000 in 2000 to nearly 47,000 at the 2020 Census. Renters include young families, commuters, and professionals who want small-town living close to Orlando. Well-kept homes that are priced right don't sit long here.
Allow The Listing Real Estate Management to be your boutique Winter Garden property management service provider. We strive to provide the best property management services to the owners and residents of Winter Garden, and our goal is to manage every part of your Winter Garden rental property effectively and efficiently.
We also manage rentals in nearby Clermont, Windermere, and Dr. Phillips.
Straight answers to the questions Winter Garden rental owners ask us most.
The Listing charges two fees for full-service property management in Winter Garden: 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.
A full-service Winter Garden 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.
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.
It depends on size, location, condition, and the community. As of October 2026, Rentometer's data put the average three-bedroom rental in Winter Garden around $2,600 a month and four-plus-bedroom homes around $3,400. For a number specific to your property, request a free rental analysis.
We manage rental properties throughout Winter Garden (ZIP code 34787) and the rest of West Orange County, along with Windermere, 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.
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.
For a lot of investors, yes. Winter Garden's population more than tripled between 2000 and 2020, it's about 14 miles from downtown Orlando, and the walkable downtown and quick access to SR 429 keep renter demand steady. Like any market, your results depend on buying the right home at the right price and managing it well.
Tell us about your Winter Garden rental and a local property manager will reach out. Prefer to talk now? Call 407-792-5900.
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