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Apartments For Rent By Owner in Winter Park, FL

17 Rentals
.
  1. Building Photo - 5312 Poinsetta Ave
    1 BED, 1 BATH
    $1,000
    Total Monthly Price Total Monthly Price New
    Base Rent$1,000
    Required Monthly FeesNone
    Total Monthly Price$1,000

    5312 Poinsetta Ave Unit 2

    5312 Poinsetta Ave, Winter Park, FL 32792
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  3. Rent Special
    Rent Special
    2 BEDS, 2 BATHS
    $2,100
    Total Monthly Price Total Monthly Price New
    Base Rent$2,100
    Required Monthly FeesNone
    Total Monthly Price$2,100

    955 Aragon Ave Unit Apt A

    955 Aragon Ave, Winter Park, FL 32789
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  4. STUDIO, 1 BATH
    $1,245+
    1 BED, 1 BATH
    $1,245+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,245
    Required Monthly FeesNone
    Total Monthly Price$1,245

    2037 Linden Rd Unit 2037lindenrdA

    2037 Linden Rd, Winter Park, FL 32792
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  5. 2 BEDS, 2.5 BATHS
    $1,850
    Total Monthly Price Total Monthly Price New
    Base Rent$1,850
    Required Monthly FeesNone
    Total Monthly Price$1,850

    2924 Antique Oaks Cir Unit 48

    2924 Antique Oaks Cir, Winter Park, FL 32792
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  6. 2 BEDS, 2 BATHS
    $1,900
    Total Monthly Price Total Monthly Price New
    Base Rent$1,900
    Required Monthly FeesNone
    Total Monthly Price$1,900

    622 St Johns Ct

    622 St Johns Ct, Winter Park, FL 32792
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  7. 1 BED, 1 BATH
    $2,450
    Total Monthly Price Total Monthly Price New
    Base Rent$2,450
    Required Monthly FeesNone
    Total Monthly Price$2,450

    151 N Orlando Ave Unit 262

    151 N Orlando Ave, Winter Park, FL 32789
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  8. 2 BEDS, 2 BATHS
    $2,000
    Total Monthly Price Total Monthly Price New
    Base Rent$2,000
    Required Monthly FeesNone
    Total Monthly Price$2,000

    1250 S Denning Dr Unit 127

    1250 S Denning Dr, Winter Park, FL 32789
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  10. 2 BEDS, 2 BATHS
    $2,275
    Total Monthly Price Total Monthly Price New
    Base Rent$2,275
    Required Monthly FeesNone
    Total Monthly Price$2,275

    2912 Plaza Terrace Dr

    2912 Plaza Terrace Dr, Orlando, FL 32803
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  11. 3 BEDS, 2 BATHS
    $2,000
    Total Monthly Price Total Monthly Price New
    Base Rent$2,000
    Required Monthly FeesNone
    Total Monthly Price$2,000

    2810 Sandwell Dr

    2810 Sandwell Dr, Winter Park, FL 32792
  12. 3 BEDS, 2 BATHS
    $2,400
    Total Monthly Price Total Monthly Price New
    Base Rent$2,400
    Required Monthly FeesNone
    Total Monthly Price$2,400

    530 Byron Rd

    530 Byron Rd, Winter Park, FL 32792
  13. 2 BEDS, 2.5 BATHS
    $1,650
    Total Monthly Price Total Monthly Price New
    Base Rent$1,650
    Required Monthly FeesNone
    Total Monthly Price$1,650

    3373 Cedar Springs Pl

    3373 Cedar Springs Pl, Winter Park, FL 32792
  14. 2 BEDS, 2 BATHS
    $1,950
    Total Monthly Price Total Monthly Price New
    Base Rent$1,950
    Required Monthly FeesNone
    Total Monthly Price$1,950

    1920 Woodcrest Dr Unit 13

    1920 Woodcrest Dr, Winter Park, FL 32792
  15. 2 BEDS, 1 BATH
    $1,500
    Total Monthly Price Total Monthly Price New
    Base Rent$1,500
    Required Monthly FeesNone
    Total Monthly Price$1,500

    2407 Branch Way Unit 105

    2407 Branch Way, Maitland, FL 32751
  16. Discounts
    Discounts
    1 BED, 1 BATH
    $1,300
    Total Monthly Price Total Monthly Price New
    Base Rent$1,300
    Required Monthly FeesNone
    Total Monthly Price$1,300

    468 Banyon Tree Cir Unit 202

    468 Banyon Tree Cir, Maitland, FL 32751

Winter Park at a Glance

Average Rent

$1,479
(All bedrooms and property types)
Learn more about
Average Rent in Winter Park
7

School Rating

out of 10 Rating
Learn more about
Schools in Winter Park

Winter Park, FL Apartments for Rent

Winter Park was founded as a resort community by northern business magnates in the late 19th century and has maintained its reputation as one of Central Florida's most desirable places to live. Those searching for apartments for rent in Winter Park will discover tree-lined brick streets, a chain of interconnected lakes, and the cultural centerpiece of Park Avenue, which features boutique shops, art galleries, and dining options. The city is also home to Rollins College and the Charles Hosmer Morse Museum of American Art, which houses the world's most comprehensive collection of Tiffany glass.

Renting in Winter Park provides convenient access to both local attractions and the broader Orlando metropolitan area. The city's apartment communities range from lakefront properties to garden-style residences near downtown, with options spanning studios to multi-bedroom layouts. Major highways including Interstate 4 are easily accessible for commuters heading to Orlando's business districts, theme parks, and employment centers. The 47.6-acre Mead Botanical Garden and the city's scenic canal system offer outdoor recreation, while Park Avenue's walkable downtown creates opportunities for shopping and entertainment without leaving the city limits.

Renting in Winter Park

Average Rental Rates and Apartment Sizes

Top Budget-Friendly Neighborhoods in Winter Park

(For 1 bedroom apartments)

Average Rent in Nearby Cities

(For 1 bedroom apartments)

Education

GreatSchools Rating
Winter Park High

Public High School

Public
Grades 9-12
3,369 Students
GreatSchools Rating
Winter Park High School

Public High School

Public
Grades 9-12
3,304 Students
GreatSchools Rating
Lake Howell High School

Public High School

Public
Grades 9-12
2,239 Students

Data provided by GreatSchools.org 2025 © 2025. All rights reserved.

Apartments for Rent Near Winter Park

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Winter Park Apartments for Rent in Your Budget

Frequently asked questions about renting in Winter Park, FL

What are the average rent costs in Winter Park, FL?

The average rent in Winter Park, FL is $1,479.

What are the average rent costs of a studio apartment in Winter Park, FL?

The average rent for a studio apartment in Winter Park, FL is $1,423.

What are the average rent costs of a one bedroom apartment in Winter Park, FL?

The average rent for a 1 bedroom apartment in Winter Park, FL is $1,479.

What are the average rent costs of a two bedroom apartment in Winter Park, FL?

The average rent for a 2 bedroom apartment in Winter Park, FL is $1,780.

What are the average rent costs of a three bedroom apartment in Winter Park, FL?

The average rent for a 3 bedroom apartment in Winter Park, FL is $1,992.

What are the average rent costs of a four bedroom apartment in Winter Park, FL?

The average rent for a 4 bedroom apartment in Winter Park, FL is $1,940.

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