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200 listings

Apartments and Houses for Rent in Winter Park, FL

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24 of 200 Listings

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24 of 200 Listings

8Active

$1,750/mo

2 bd · 1 ba · 1,100 sqft

300 N Knowles Ave 214, Winter Park, FL

Robert Bush · Property Professionals, Inc.

8Active

$1,585/mo

2 bd · 3 ba · 1,031 sqft

7444 Woodburn Ct #29, Winter Park, FL

Abranette Lopez · LPT REALTY, LLC

10Active

$3,995/mo

3 bd · 4 ba · 1,810 sqft

735 Minnesota Ave, Winter Park, FL

Marilyn Kuczynski · FLORIDA HOMES SALES & MANAGEMENT LLC

18Active

$1,600/mo

2 bd · 2 ba · 756 sqft

7262 Swallow Run #7262, Winter Park, FL

Karla Pacheco · LUMINA PROPERTY MANAGEMENT LLC

30Active

$1,900/mo

3 bd · 2 ba · 1,230 sqft

1954 Spring St, Winter Park, FL

Irina Paul, LLC · FUTURE HOME REALTY INC

30Active

$2,200/mo

1 bd · 2 ba · 915 sqft

690 Osceola Ave #407, Winter Park, FL

Delaney Heidenescher · CREEGAN GROUP

54Active

$6,495/mo

5 bd · 2 ba · 2,750 sqft

Address withheld · Winter Park, FL

Monica Vega Stiskin, LLC · PREFERRED REAL ESTATE BROKERS

10Active

$3,995/mo

3 bd · 4 ba · 1,810 sqft

737 Minnesota Ave, Winter Park, FL

Marilyn Kuczynski · FLORIDA HOMES SALES & MANAGEMENT LLC

15Active

$1,895/mo

2 bd · 3 ba · 960 sqft

307 Sandlewood Trl, Winter Park, FL

Matthew Kirsch · REAL PROPERTY MANAGEMENT AND REALTY

5Active

$1,330/mo

0 bd · 1 ba · 475 sqft

300 N Knowles Ave 205, Winter Park, FL

Robert Bush · Property Professionals, Inc.

17Active

$1,999/mo

3 bd · 2 ba · 1,096 sqft

1603 Winter Green Blvd, Winter Park, FL

Nancy Guadagnino · SPECIALIZED PROPERTY MANAGEMENT

12Active

$1,525/mo

2 bd · 2 ba · 1,018 sqft

2941 Antique Oaks Cir #80, Winter Park, FL

Summer Hornburg · BELMONT REALTY

47Active

$8,500/mo

4 bd · 4 ba · 3,184 sqft

440 Clarendon Avenue, Winter Park, FL

Meg Dolan · FANNIE HILLMAN & ASSOCIATES

18Active

$2,200/mo

3 bd · 2 ba · 1,266 sqft

Address withheld · Winter Park, FL

Kirsten Cantello · TRUSTHOME PROPERTIES INC

24Active

$1,900/mo

2 bd · 2 ba · 1,173 sqft

2503 Tahoe Cir #2503, Winter Park, FL

Carissa Lawhun · FLORIDA REALTY INVESTMENTS

45Active

$2,149/mo

2 bd · 3 ba · 1,250 sqft

2300 Barbados Drive, Winter Park, FL

Cristian Cen Chen · SIMPSON REALTY LLC

18Active

$2,200/mo

3 bd · 2 ba · 1,266 sqft

Address withheld · Winter Park, FL

Kirsten Cantello · TRUSTHOME PROPERTIES INC

24Active

$1,900/mo

2 bd · 2 ba · 1,173 sqft

2503 Tahoe Circle 2503, Winter Park, FL

Carissa Lawhun · FLORIDA REALTY INVESTMENTS

45Active

$2,149/mo

2 bd · 3 ba · 1,250 sqft

2300 Barbados Dr, Winter Park, FL

Cristian Cen Chen · SIMPSON REALTY LLC

47Active

$8,500/mo

4 bd · 4 ba · 3,184 sqft

440 Clarendon Ave, Winter Park, FL

Meg Dolan · FANNIE HILLMAN & ASSOCIATES

30Active

$2,500/mo

2 bd · 1 ba · 924 sqft

800 W Canton Avenue, Winter Park, FL

Kelly Price · KELLY PRICE & COMPANY LLC

26Active

$2,800/mo

3 bd · 3 ba · 2,378 sqft

2305 Shadowland Loop, Winter Park, FL

Laura Lerma · 2 GOOD REALTY

20Active

$2,300/mo

4 bd · 3 ba · 1,611 sqft

7487 Canford Court 5, Winter Park, FL

Jiny Lee · THE FLORIDA LOUNGE REALTY LLC

26Active

$2,800/mo

3 bd · 3 ba · 2,378 sqft

2305 Shadowland Loop, Winter Park, FL

Laura Lerma · 2 GOOD REALTY

1 2…9

Listing data & MLS disclosures

MIAMI REALTORS MLS: The multiple listing information is provided by MIAMI Association of Realtors® from a copyrighted compilation of listings. The compilation of listings and each individual listingare ©2026 MIAMI Association of Realtors®. All Rights Reserved.
The information provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Last Updated: 2026-10-06 04:01:36 UTC
Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Winter Park, FL community profile

Population: 31,855
Median income: $98,252
Housing units: 15,404
People per sq. mi.: 1,409.5
Area: 22.6 sq. mi.

Source: HJN community data

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Listing data & MLS disclosures

MIAMI REALTORS MLS: The multiple listing information is provided by MIAMI Association of Realtors® from a copyrighted compilation of listings. The compilation of listings and each individual listingare ©2026 MIAMI Association of Realtors®. All Rights Reserved.
The information provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All properties are subject to prior sale or withdrawal. All information provided is deemed reliable but is not guaranteed accurate, and should be independently verified. Last Updated: 2026-10-06 04:01:36 UTC
Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Winter Park, FL community profile

Population: 31,855
Median income: $98,252
Housing units: 15,404
People per sq. mi.: 1,409.5
Area: 22.6 sq. mi.

Source: HJN community data

Apartments and Houses for Rent in Winter Park, FL | Realty.com