Apartments and Houses for Rent in Winter Park, FL

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24 of 100 Listings

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Apartments and Houses for Rent in Winter Park, FL

24 of 100 Listings

23Active
$2,300/mo
2 bd · 1 ba · 709 sqft
500 N Pennsylvania Ave #G, Winter Park, FL
Sylvia Young · FLORIDA RENTAL TEAM
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 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
26Active
$2,800/mo
3 bd · 3 ba · 2,378 sqft
2305 Shadowland Loop, Winter Park, FL
Laura Lerma · 2 GOOD REALTY
30Active
$2,500/mo
2 bd · 1 ba · 924 sqft
800 W Canton Ave, Winter Park, FL
Kelly Price · KELLY PRICE & COMPANY LLC
20Active
$2,300/mo
4 bd · 3 ba · 1,611 sqft
7487 Canford Ct #5, Winter Park, FL
Jiny Lee · THE FLORIDA LOUNGE REALTY LLC
11Active
$3,995/mo
3 bd · 4 ba · 1,760 sqft
737 Minnesota Ave, Winter Park, FL
Marilyn Kuczynski · FLORIDA HOMES SALES & MANAGEMENT LLC
18Active
$1,600/mo
2 bd · 2 ba · 1,063 sqft
7453 Daniel Webster Dr #a5, Winter Park, FL
Laila Dkhissi · LA ROSA REALTY PREMIER LLC
1Active
$2,800/mo
5 bd · 4 ba · 1,442 sqft
2181 Linden Rd, Winter Park, FL
Paula Chavez · KELLER WILLIAMS ADVANTAGE III
50Active
$12,000/mo
4 bd · 4 ba · 3,553 sqft
541 W Canton Ave, Winter Park, FL
Bianca Khoury · PREMIER SOTHEBY'S INTL. REALTY
45Active
$7,500/mo
4 bd · 4 ba · 3,249 sqft
1750 Carollee Lane, Winter Park, FL
Michelle Hochfelder · PREMIER SOTHEBY'S INTL. REALTY
37Active
$5,500/mo
4 bd · 3 ba · 3,050 sqft
2056 Wood Thrush Ln, Winter Park, FL
Kimberley Gernert LLC · BALDWIN PARK REALTY LLC
13Active
$1,600/mo
2 bd · 2 ba · 1,020 sqft
163 Scottsdale Sq #163, Winter Park, FL
Simone Pinto de Almeida Santos · NOVA REAL ESTATE SERVICES INC
33Active
$2,000/mo
3 bd · 3 ba · 1,565 sqft
7101 Swallow Run, Winter Park, FL
Jackie O'Leary · FANNIE HILLMAN & ASSOCIATES
21Active
$1,550/mo
2 bd · 2 ba · 1,018 sqft
2918 Antique Oaks Cir #30, Winter Park, FL
Kyle Petteway · EXIT REAL ESTATE RESULTS
39Active
$4,140/mo
4 bd · 4 ba · 3,094 sqft
2352 Kestrel Perch Pl, Winter Park, FL
Angela Fettig · KELLER WILLIAMS REALTY AT THE PARKS
17Active
$2,000/mo
2 bd · 2 ba · 1,040 sqft
155 Stefanik Rd, Winter Park, FL
Paul Jimenez · URBANISTA BROKERS
20Active
$3,500/mo
3 bd · 3 ba · 1,715 sqft
1667 Mizell Ave, Winter Park, FL
Justin LaManna · HOMEVEST REALTY
16Active
$2,400/mo
3 bd · 2 ba · 1,570 sqft
2809 W Fairbanks Ave, Winter Park, FL
Anne Coburn · H. & H. REALTY, INC.
18Active
$2,100/mo
3 bd · 2 ba · 1,174 sqft
3217 Royal St, Winter Park, FL
Stephen Murphy · DALTON WADE INC
18Active
$2,200/mo
3 bd · 2 ba · 1,467 sqft
Address withheld · Winter Park, FL
Kirsten Cantello · TRUSTHOME PROPERTIES INC
33Active
$2,500/mo
3 bd · 2 ba · 1,277 sqft
4870 Seminole Ave, Winter Park, FL
Tamara Mazo Ferro · COLDWELL BANKER REALTY

Listing data & MLS disclosures

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

Explore Winter Park rentals

Listing data & MLS disclosures

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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Listing data & MLS disclosures

Winter Park, FL community profile

Explore Winter Park rentals

Listing data & MLS disclosures

Winter Park, FL community profile