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Apartments For Rent By Owner in Winter Park, FL

20 Rentals
.
  1. Building Photo - 1915 Taylor Ave
    3 BEDS, 2 BATHS
    $4,354
    Total Monthly Price Total Monthly Price New
    Base Rent$4,354
    Required Monthly FeesNone
    Total Monthly Price$4,354

    1915 Taylor Ave

    1915 Taylor Ave, Winter Park, FL 32792
    Apply
  2. Building Photo - 1913 South Blvd
    1 BED, 1 BATH
    $1,700
    Total Monthly Price Total Monthly Price New
    Base Rent$1,700
    Required Monthly FeesNone
    Total Monthly Price$1,700

    1913 South Blvd Unit B

    1913 South Blvd, Maitland, FL 32751
    (689) 225-6561
  4. Building Photo - 3217 Royal St
    3 BEDS, 2 BATHS
    $2,200
    Total Monthly Price Total Monthly Price New
    Base Rent$2,200
    Required Monthly FeesNone
    Total Monthly Price$2,200

    3217 Royal St

    3217 Royal St, Winter Park, FL 32792
    Apply
  5. 1 BED, 1 BATH
    $1,750
    Total Monthly Price Total Monthly Price New
    Base Rent$1,750
    Required Monthly FeesNone
    Total Monthly Price$1,750

    276 Cambridge Blvd

    276 Cambridge Blvd, Winter Park, FL 32789
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  6. 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
    Apply
  7. 1 BED, 1 BATH
    $2,300
    Total Monthly Price Total Monthly Price New
    Base Rent$2,300
    Required Monthly FeesNone
    Total Monthly Price$2,300

    151 N Orlando Ave Unit 262

    151 N Orlando Ave, Winter Park, FL 32789
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  8. 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
    Apply
  9. 3 BEDS, 2 BATHS
    $2,695
    Total Monthly Price Total Monthly Price New
    Base Rent$2,695
    Required Monthly FeesNone
    Total Monthly Price$2,695

    1509 Springtime Loop

    1509 Springtime Loop, Winter Park, FL 32792
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  10. 2 BEDS, 2 BATHS
    $1,545
    Total Monthly Price Total Monthly Price New
    Base Rent$1,545
    Required Monthly FeesNone
    Total Monthly Price$1,545

    1172 Calle Del Rey Unit A

    1172 Calle Del Rey, Casselberry, FL 32707
    Apply
  11. 3 BEDS, 2.5 BATHS
    $4,450
    Total Monthly Price Total Monthly Price New
    Base Rent$4,450
    Required Monthly FeesNone
    Total Monthly Price$4,450

    4062 Markham Pl

    4062 Markham Pl, Orlando, FL 32814
    Apply
  12. 3 BEDS, 2.5 BATHS
    $2,500
    Total Monthly Price Total Monthly Price New
    Base Rent$2,500
    Required Monthly FeesNone
    Total Monthly Price$2,500

    900A Timor Ave

    900A Timor Ave, Orlando, FL 32804
    Apply
  13. Rent Special
    Rent Special
    2 BEDS, 1 BATH
    $1,700
    Total Monthly Price Total Monthly Price New
    Base Rent$1,700
    Required Monthly FeesNone
    Total Monthly Price$1,700

    1010 Timor Ave

    1010 Timor Ave, Orlando, FL 32804
    Apply
  14. 3 BEDS, 2.5 BATHS
    $2,450
    Total Monthly Price Total Monthly Price New
    Base Rent$2,450
    Required Monthly FeesNone
    Total Monthly Price$2,450

    1840 Bachman Way

    1840 Bachman Way, Winter Park, FL 32792
  15. 2 BEDS, 1.5 BATHS
    $1,700
    Total Monthly Price Total Monthly Price New
    Base Rent$1,700
    Required Monthly FeesNone
    Total Monthly Price$1,700

    7404 Woodburn Ct

    7404 Woodburn Ct, Winter Park, FL 32792
  16. 1 BED, 1 BATH
    $1,550+
    3 BEDS, 1 BATH
    $1,950+
    Total Monthly Price Total Monthly Price New
    Base Rent$1,550 - $1,950
    Required Monthly FeesNone
    Total Monthly Price$1,550 - $1,950

    200 Saint Andrews Blvd

    200 Saint Andrews Blvd, Winter Park, FL 32792
  17. 3 BEDS, 2 BATHS
    $2,250
    Total Monthly Price Total Monthly Price New
    Base Rent$2,250
    Required Monthly FeesNone
    Total Monthly Price$2,250

    2038 Ponderosa Ave

    2038 Ponderosa Ave, Winter Park, FL 32792
  18. 3 BEDS, 1 BATH
    $1,995
    Total Monthly Price Total Monthly Price New
    Base Rent$1,995
    Required Monthly FeesNone
    Total Monthly Price$1,995

    2603 musselwhite avenue Unit 2603

    2603 musselwhite avenue, Orlando, FL 32804
  19. 3 BEDS, 2 BATHS
    $3,200
    Total Monthly Price Total Monthly Price New
    Base Rent$3,200
    Required Monthly FeesNone
    Total Monthly Price$3,200

    1594 Common Way Rd Unit #101

    1594 Common Way Rd, Orlando, FL 32814

Winter Park at a Glance

Average Rent

$1,474
(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)
  • Neighborhoods Average Sq Ft Average Rent
  • Lake Howell 727 Sq Ft $1,536/mo
  • Fairview 741 Sq Ft $1,796/mo

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

Specialty Housing

Choose by Amenities

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 $1,474.

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 $1,375.

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 $1,474.

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 $1,744.

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 $2,152.

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 $1,849.

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