Compare 19 local companies in Winter Park. Pick up to 3 and send one free quote request.
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Top rated
Highly Recommended · 100+ reviews
Most reviewed
443 Google reviews, 4.4★
Longest established
20+ years in business
Picked by our rules (rating adjusted for review count, number of reviews, years in business), not paid placement.
Tick Compare on up to 3 companies to see them side by side and request quotes from all of them at once.
1366 Gene St, Winter Park, FL 32789
HOST Management Group is a Winter Park company managing long-term rentals and short-term vacation homes across Tampa Bay, Central Florida and the Space Coast, with screening, rent collection, maintenance, leasing and marketing.
In their words: “From marketing and guest relations to maintenance coordination and financial reporting, we handle the details so you can enjoy the benefits of ownership with confidence.”
Review summary: Most reviewers mention beautiful homes, a responsive team and prompt fixes for any issues.
1177 Louisiana Ave Ste 106, Winter Park, FL 32789
Red Door Investment Grp is a Winter Park property management and sales office handling maintenance, leasing, marketing and evictions for single-family homes and multifamily properties.
In their words: “You will have full access to your owner portal, where you will be able to see your income, your disbursements and/or any maintenance payments that have been made.”
Review summary: Most reviewers mention comfortable apartments, respectful staff and quick maintenance.
656 Formosa Ave, Winter Park, FL 32789
Orlando Property Management - RentSmartUSA has an office in Winter Park and has managed single-family and multi-family rentals in the Orlando area since 2010, with tiered management plans, tenant placement and detailed inspections.
In their words: “We offer a full range of property management services tailored to you as a rental owner.”
Review summary: Most reviewers mention fast responses, helpful staff and an easy leasing process, though a few tenants reported slow repairs.
931 S Semoran Blvd Ste 214, Winter Park, FL 32792
Innovation Property Management is a Winter Park company, founded in 1972, managing residential, commercial and retail properties and community associations in Orlando and Orange, Osceola and Polk counties.
In their words: “At Innovation Property Management, we’re proud of our service to the property management and community association industries.”
Review summary: Most reviewers mention responsive, detail-oriented staff and a smooth rental process.
Real Property Management & Realty is a Real Property Management franchise office in Winter Park that has managed single-family homes across Greater Orlando and Central Florida since 1995, alongside leasing, tenant screening, evictions and real estate sales.
In their words: “We find quality residents who will take care of your property and pay on time.”
Review summary: Most reviewers mention tenant placement, an easy application process and a responsive team that answers questions quickly.
Belmont Management Group is a Winter Park company founded in 2009 that manages residential and multi-family properties in Orlando and Central Florida, with marketing, screening, rent collection, maintenance and accounting.
In their words: “At Belmont, we’re more than property managers—we’re investors too.”
Review summary: Most reviewers mention prompt, kind staff, easy lease extensions and a smooth rental process.
1155 Louisiana Ave Ste 207A, Winter Park, FL 32789
RE/MAX 200 Realty - Property Management Division is a Winter Park office handling residential leasing and management of single-family homes in Greater Orlando, including Orange and Seminole counties, Altamonte Springs and Longwood.
In their words: “RE/MAX 200 Realty Property Management Division serves all of your residential leasing and management needs in the Greater Central Florida area.”
Review summary: Most reviewers mention a professional, attentive team, good client care and quick tenant placement.
1011 Wymore Rd, Winter Park, FL 32789
Great American Land Management is a Fairview Shores company leasing residential and commercial properties to tenants in the Winter Park area.
2431 Aloma Ave STE 124, Winter Park, FL 32792
PMI Property Solutions is a Winter Park office of the Property Management Inc franchise, offering residential, commercial and association management in Orlando, Winter Park, Lake Mary, Casselberry and Sanford.
Review summary: Reviewers often describe an experienced, communicative team, mostly for home sales.
3001 Aloma Ave Ste 213, Winter Park, FL 32792
Real Property Management Vanguard is a Real Property Management franchise office in Winter Park that manages single-family homes in Winter Park and Orange County, with tenant screening, leasing, maintenance and evictions.
Review summary: Reviewers often describe a personable, attentive property manager who communicates well and places tenants quickly.
1950 Lee Rd #216, Winter Park, FL 32789
Professional Management is a Winter Park company that manages apartment communities, multi-family and commercial properties across Florida, with compliance, lease-up, asset stabilization and accounting services.
In their words: “Our approach is grounded in thoughtful planning, proactive management, and results-driven execution.”
MoreHouse Property Management, part of MoreHouse Realty established in 2001, is a Winter Park company offering residential property management, leasing and sales in Central Florida.
In their words: “At MoreHouse Realty we offer full property management and sales services for clients in the Central Florida area.”
The Jander Group is a Winter Park company established in 1990 to manage homes for owners and investors in Greater Orlando, also offering community association management, consulting and sales, with an office serving Memphis.
In their words: “We excel by offering professional, tested and proven management strategies.”
1801 Lee Rd #305, Winter Park, FL 32789
Bric Property Management is a Winter Park company, part of Bric Realty, offering residential property management, available rentals and real estate sales in the Orlando area.
2431 Aloma Ave STE 124, Winter Park, FL 32792
AGG Realty and Management has an office in Winter Park and provides full-service residential property management in Central Florida, with each owner working directly with one assigned property manager and a capped portfolio size.
3001 Aloma Ave, Winter Park, FL 32792
Keystone Estates is a Winter Park residential property management company serving Seminole, Orange, Osceola, Lake and Volusia counties, specializing in single-family homes and small multifamily properties up to quadplex.
1095 W Morse Blvd #100, Winter Park, FL 32789
Range Real Estate is a Winter Park company offering rental management and leasing for residential and commercial property owners in the Winter Park area.
941 W Morse Blvd Ste 100, Winter Park, FL 32789
Reign Premier Management Services has an office in Winter Park and offers residential and commercial property management, including tenant placement, rent collection and property maintenance.
401 W Fairbanks Ave Ste 200, Winter Park, FL 32789
The Cavalieri Property Management is a Winter Park company providing full-service residential and rental property management in Orlando and Central Florida.
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Pins show office addresses; numbers match the Best match order. Companies that don't publish an address are listed as "Serves the Winter Park area" and get no pin.
Get the latest rental and real estate data on the Winter Park market. We update these charts with the latest data on the 22nd of each month.
Rents in Winter Park are $81 below the Orange County typical.
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed. Data through September 2026.
Rent rose in 7 of the last 12 months: +$49 in all since Oct 2025.
Green: rent went up that month. Grey: it went down.
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed. Data through September 2026.
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed. Data through September 2026.
Winter Park's typical asking rent is $81 (4.2%) below the county. The gap is shrinking compared with a year ago.
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed. Data through September 2026.
Winter Park is number 9 of 10 cities in the county by typical asking rent.
Cities with at least 13 months of Zillow data. Left out (too few months): Gotha, Oakland. Linked cities have their own page.
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed, 1-year change. Data through September 2026.
Rents here usually rise most in March, May and June, so those are good months to list your rental.
Average change from the month before, 11 years of data.
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed. Data through September 2026.
Past growth, not a forecast. Rents can go down as well as up. Your own rent depends on the home, its condition and the lease.
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed. Data through September 2026.
| City | Typical rent | 1 year | Managers |
|---|---|---|---|
| Winter Park | $1,852 | +2.7% | 19 |
| Maitland | $1,960 | +4.1% | 3 |
| Casselberry | $1,825 | +1.8% | 4 |
| Altamonte Springs | $1,588 | −0.2% | 12 |
| Longwood | $1,933 | +2.2% | 4 |
| Winter Springs | $2,007 | +2.2% | 3 |
| Oviedo | $2,158 | +1.2% | 6 |
Source: Zillow Observed Rent Index (ZORI), typical asking rent, data through September 2026. Managers listed: our directory, October 2026.
Source: U.S. Census Bureau, American Community Survey 5-year estimates, 2020-2024.
Source: U.S. Department of Housing and Urban Development, Fair Market Rents for fiscal year 2027, Orlando-Kissimmee-Sanford, FL MSA. Used to set Housing Choice Voucher (Section 8) limits.
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Compare the 19 property management companies in Winter Park, Orange County. Tick up to 3 to see them side by side, then request free quotes from all of them in one step. Highly rated managers based nearby, in Orlando and Casselberry, are listed below the local companies.
Zillow's typical asking rent in Winter Park is $1,852 (September 2026); +2.7% over the past year and +18.8% over five years. About 33.8% of homes in Winter Park are rented, and the rental vacancy rate is 8.2% (Census, 2020-2024).
We list 19 property management companies in Winter Park, FL.
Zillow's typical asking rent in Winter Park was $1,852 a month in September 2026, +2.7% on a year earlier.
Over the 11 years Zillow has tracked, asking rents here have risen most in March, May and June. Listing in those months can help, but every property is different.
Fees depend on the company, the property and the services you need, and few companies publish them. Ask for a written quote that lists the monthly fee, leasing fee and any other charges. You can request quotes from up to 3 managers at once on this page.
The default order, Best match, uses each company's Google rating adjusted for how many reviews it has, so a 4.8 rating from 100 reviews ranks above a 5.0 from 2. Companies with no Google reviews yet are listed after every rated company. No company can pay for its position.
Yes. Requesting quotes is free for property owners and there is no obligation to hire anyone.