Zumper

500 N Pennsylvania Ave
500 N Pennsylvania Ave, Winter Park, FL 32789, USA

Condo for rent
Dog friendly
Monthly rent
$2,300
Beds2
Baths1
Sqft709
modified
Updated 2 Hours Ago

Property Overview

This summary uses Zumper’s proprietary data. “Things you’ll love” and “Great for” are based on our internal analyses of market trends and renter insights.

Things you’ll love

  • Images Available

Great for

  • Social life
  • Wellness

Units

500 N Pennsylvania Ave Winter Park, FL

New Listing

G

2 Beds

1 Bath

$2,300

Listed on 09/27/2026
Listed by 2/1-WINTER PARK CONDO NEAR PARK AVE
This updated Winter Park gem offers a bright, inviting layout in a highly sought‑after location just minutes from Park Avenue. Unit G features a comfortable living area with plenty of natural light, a well‑appointed kitchen, and a spacious bedroom designed for easy everyday living. The community has a clean, well‑kept feel, with convenient access to shopping, dining, Rollins College, and major roadways. If you’re looking for a charming, move‑in‑ready space in one of Central Florida’s most desirable neighborhoods, this unit delivers a great blend of comfort and convenience. One small dog up to 25 lbs allowed (pet fees apply). Contact Florida Rental Team to schedule your private showing.

New Listing

2 Beds, 1 Bath

2 Beds

1 Bath

$2,300

Listed on 09/26/2026
Listed by Sylvia Pletka
Days on market: 1
This updated Winter Park gem offers a bright, inviting layout in a highly sought-after location just minutes from Park Avenue. Unit G features a comfortable living area with plenty of natural light, a well-appointed kitchen, and a spacious bedroom designed for easy everyday living. The community has a clean, well-kept feel, with convenient access to shopping, dining, Rollins College, and major roadways. If you’re looking for a charming, move-in-ready space in one of Central Florida’s most desirable neighborhoods, this unit delivers a great blend of comfort and convenience. One small dog up to 25 lbs allowed (pet fees apply). Contact Florida Rental Team to schedule your private showing. Contact us to schedule a showing.

Occupied Units

Occupied

F

2 Beds

1 Bath

$1,950

Listed by Angela Fettig
Days on market: 1095
This 2 bed/1 bath condo is just 3 blocks from Park Ave shopping and dining and 2 blocks from Winter Park Village. It includes a stackable washer/dryer, stainless steel appliances and a walk in closet in the primary bedroom. It is also convenient to Winter Park golf course and Hannibal Square. Sorry no pets. Applications and information available at KWrentsOrlando com Rental Terms: Rent: $1,950, Application Fee: $75, Security Deposit: $1,950, Available Now Pet Policy: Cats not allowed, Dogs not allowed Contact us to schedule a showing.

Amenities for 500 N Pennsylvania Ave

Some units at this address have these amenities. View unit details for more information.

Building
  • Dogs Ok
Unit Amenities
  • Walk-In Closets
  • In-Unit Laundry

Policies at 500 N Pennsylvania Ave

Applicants

Applicants

One-time.

Contact Property

REQUIRED FEES

Security Deposit

One-time. Refundable.

Contact Property

Dog Policy

Allowed
Limit1

Cat Policy

Not allowed

Questions about this property’s policies and fees?

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About 500 N Pennsylvania Ave

HomeApartments in Winter Park 500 N Pennsylvania Ave #G, Winter Park, FL 32789, USA

Interested in leasing 500 N Pennsylvania Ave, Winter Park, FL 32789, USA? Currently, 500 N Pennsylvania Ave, Winter Park, FL 32789, USA is available to rent or lease. It is a 2-bedroom condo with 1 bathroom. Below, you can compare the rent price at 500 N Pennsylvania Ave, Winter Park, FL 32789, USA vs overall rent prices in Winter Park, FL. We have compiled nearby businesses and things to do close to 500 N Pennsylvania Ave, Winter Park, FL 32789, USA.

Address details

Units3
Units available2
City
Zip code32789

500 N Pennsylvania Ave #G is great for:

Social life

  • Areas nearby are accessible by walking
  • 231 restaurants within 1 mile of this property
  • The area has transit options
  • 367 mixed-use spaces nearby

Wellness

  • Ample windows and natural lighting
  • 25 sports facilities (like tennis courts) nearby
  • There are 13 grocery stores within 1 mile
  • 54 gyms or yoga centers nearby

Property highlights

We compared every listing in the surrounding area to determine which amenities are most common. If a building lacks an amenity that most others in the area have, it is a con. If a building has an amenity most others in the area do not, it is a pro. Similarly, price, schools, and size are calculated relative to the size, price, and distance to schools of the other properties nearby.

How 500 N Pennsylvania Ave, Winter Park, FL 32789, USA compares to other nearby properties.

Positives

Images Available
There are at least 10 photos of this address

Considerations

Greater distance from grade schools
The nearest elementary school is farther than 2 miles away
Greater distance from high schools
The nearest high school is farther than 2 miles away
Greater distance from middle schools
The nearest middle school is farther than 2 miles away
Grow a garden indoors
A balcony, backyard, or shared outdoor space isn't available
No in-unit dishwasher
Dishwashers aren't available

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Rent trends in Winter Park

If you decide to upgrade your space, you can expect 2-bedrooms at 500 N Pennsylvania Ave #G to be 35% more than the average for similarly sized apartments in Winter Park.

Median rents as of Apr 4 2026.
Winter Park
A table of studio rental data trends in Winter Park
MonthMedian Rent
October 2024$1,050
November 2024$1,126
March 2025$1,519
April 2025$1,519
May 2025$1,200
June 2025$1,200
July 2025$1,290
August 2025$1,378
September 2025$1,299
October 2025$1,241
November 2025$1,235
December 2025$1,229
January 2026$1,224
February 2026$1,224
March 2026$1,224
April 2026$1,224

Affordability calculator

Can I afford to live at 500 N Pennsylvania Ave?

Bedrooms

2 bedrooms

Rent-to-income ratio

30%

Slide to adjust the percentage of your monthly income you are willing to spend on rent.
The general rule of thumb is to spend around 30% or less of your income on rent.
Recommended income

$92,000/yr

With your selected rent-to-income ratio, you'd ideally want to make $92,000 annually to afford this 2-bedrooms median monthly rent price of $2,300.
For more information on rent affordability, visit our rent calculator.

Rent history

The increase or decrease in monthly rent compared to the previous listing price.
Check out the past listing prices for monthly rent at 500 N Pennsylvania Ave, Winter Park, FL.
1 year ago$1,9502 bed1 bath
2 years ago$1,9502 bed1 bath
6 years ago$1,4002 bed1 bath
9 years ago$1,3002 bed1 bath

Schools near 500 N Pennsylvania Ave #G

Lakemont Elementary School

901 n lakemont ave

winter park, FL, 32792

PK, K-5Public
B+

Audubon Park School

1500 falcon dr

orlando, FL, 32803

PK, K-8Public
A-

OCVS Virtual Instruction Program

1600 silver star rd

orlando, FL, 32804

K-12Public

OCVS Virtual Franchise

1600 silver star rd

orlando, FL, 32804

K-12Public
A-

Orange County Virtual School

1600 silver star rd

orlando, FL, 32804

K-12Public
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Getting around Winter Park near 500 N Pennsylvania Ave

Walking

7/10
Grab your reusable bags–many shops and stores are within walking distance.

Driving

9/10
Commuting is easy with multiple accessible routes and plenty of parking.

Cycling

5/10
More spots are within biking distance and some roads are cyclist-friendly.

Transit

5/10
Frequent public transit options are within walking distance.

Points of interest for 500 N Pennsylvania Ave, Winter Park

Groceries

8/10
At least one grocery store within a few minutes' walk

Shopping

7/10
Variety of shops within walking distance

Cafes

5/10
Some cafés within walking distance

Restaurants

6/10
Variety of restaurants within walking distance

Primary schools

8/10
At least one elementary school within a 20-minute walk

High schools

3/10
No high schools within a 30-minute walk

Parks

5/10
Moderate amount of park space nearby

Nightlife

4/10
Few or no bars within walking distance

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