Apartments in Downtown Winter Park

31 - 43 of 43 Results
1
$1,695
190 W Ventris Ave Maitland, FL
2 BR | Available Now
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Dog Friendly
Cat Friendly
House
Dishwasher
1
$1,425
121 E Evans St Orlando, FL
2 BR | Available Now
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House
North Orange
16
$1,799 - 1,999
2001 Glenridge Way Winter Park, FL
1 - 2 BR | Available Now
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Dog Friendly
Cat Friendly
Air Conditioning
Surface Parking
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31
$1,717 - 3,335
190 Independence Ln Maitland, FL
1 - 2 BR | Available Now
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Luxury
Air Conditioning
Covered Parking
Fitness Center
Dishwasher
1
$1,595
Orlando, FL
2 BR | Available Now
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Cat Friendly
Storage
North Orange
54
$2,081 - 4,551
1884 Lakemont Ave Orlando, FL
Studio - 3 BR | Available Now
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Dog Friendly
Cat Friendly
Luxury
Air Conditioning
Surface Parking
19
$2,200
Winter Park, FL
3 BR | Available Now
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1
$2,150
1931 Carrigan Ave Winter Park, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
Storage
Dishwasher
8
$1,235
Maitland, FL
1 BR | Available Now
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Air Conditioning
26
$1,800
Winter Park, FL
2 BR | Available Now
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Dog Friendly
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Dishwasher
15
$792
Maitland, FL
1 BR | Ask for Availability
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12
$1,300
Winter Park, FL
1 BR | Available Now
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Dog Friendly
Cat Friendly
Balcony/Deck/Patio
Storage
Dishwasher
49
$2,250
Winter Park, FL
3 BR | Available Now
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Air Conditioning
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Winter Park:
April Rent Report

Welcome to the April 2026 Winter Park Apartment Report. In this assessment of the local rental market, Rentable data scientists and rental experts break down the April 2026 key findings and figures for the Winter Park rental landscape.

Our experts analyze the pricing trends — one-bedroom, two-bedroom, year-over-year and month-over-month — in Winter Park and surrounding areas and provide comparisons to the entire metro area, nearby cities and some of the most desirable and expensive cities in the United States. Take a look at the last 12 months of Winter Park average rent prices in the chart below.

Monthly Rent Report

$1,800
$1,350
$900
$450
$0
May. 2025
Jun. 2025
Jul. 2025
Aug. 2025
Sep. 2025
Oct. 2025
Nov. 2025
Dec. 2025
Jan. 2026
Feb. 2026
Mar. 2026
Apr. 2026
1 BR       2 BR

Winter Park Rent Prices Decrease From March to April

Winter Park rent prices decreased over the last month. From March to April, the city experienced a 0% decrease for the price of a one-bedroom apartment. The rent price for a Winter Park one-bedroom apartments currently stands at $.

When we take a look at the two-bedroom comparison from March to April, Winter Park experienced a 0% decrease for the price of a two-bedroom apartment. The rent price for a Winter Park two-bedroom apartments currently stands at $.

April Prices: Winter Park vs. Surrounding Areas

Rent Prices in Winter Park and Surrounding Areas

Rent prices have decreased in Winter Park over the last month. But how have the surrounding areas fared when it comes to the recent volatility in apartment prices? Rent prices in 0 of the Winter Park suburbs increased last month. On the other hand, 0 local areas experienced a decrease in the price of a one-bedroom apartment.

More key findings include:

  • Rents did not increase in any of the Winter Park suburbs

  • Rents did not decrease in any of the Winter Park suburbs.

April 2026 Pricing Trends: Winter Park vs. National Comparisons

Winter Park Rent Prices More Affordable Than Major Cities

Rent growth in Winter Park over the past year has been declining. When compared to major cities nearby, along with some of the most expensive cities in the country, Winter Park average rent prices appear to be relatively affordable for local residents.

The price for a Winter Park one-bedroom apartment remains vastly more affordable than four of the largest cities in the United States — New York City, Washington, D.C. San Francisco and Los Angeles. And pricing compares quite similarly to nearby Midwest cities.

For more information about Winter Park and surrounding area rent prices, take a look at the complete data set below.

Data set for Winter Park and suburbs

1 BR April 1 BR M/M % Change 2 BR April 2 BR M/M % Change

Methodology

Each month, using over 1 million Rentable listings across the United States, we calculate the median 1-bedroom and 2-bedroom rent prices by city, state, and nation, and track the month-over-month percent change. To avoid small sample sizes, we restrict the analysis for our reports to cities meeting minimum population and property count thresholds.