Apartments in Downtown Winter Park

1 - 30 of 47 Results
1
$2,195
5117 Lake Howell Rd Winter Park, FL
3 BR | Available Now
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Dishwasher
1
$2,500
130 N Center St Winter Park, FL
1 BR | Sep. 10, 2026
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Air Conditioning
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Downtown Winter Park
23
$9,500
Winter Park, FL
3 BR | Available Now
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Balcony/Deck/Patio
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15
$1,010 - 1,680
311 N Knowles Ave Winter Park, FL
Studio - 2 BR | Available Now
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Section 8
Air Conditioning
Covered Parking
1
$2,300
301 S Capen Ave Winter Park, FL
3 BR | Available Now
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Downtown Winter Park
11
$1,795
Winter Park, FL
3 BR | Available Now
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Dishwasher
14
$1,795
Winter Park, FL
3 BR | Available Now
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Air Conditioning
1
$2,095
937 Aragon Ave Winter Park, FL
2 BR | Available Now
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Disability Access
24
$2,095
Winter Park, FL
2 BR | Available Now
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1
$2,350
700 Melrose Ave Unit A-5 Winter Park, FL
2 BR | Available Now
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36
$1,804 - 4,495
1305 Morgan Stanley Ave Winter Park, FL
Studio - 2 BR | Available Now
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Luxury
Air Conditioning
Covered Parking
In Unit Laundry
Balcony/Deck/Patio
1
54
$6,350
Winter Park, FL
4 BR | Available Now
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1
$3,795
Winter Park, FL
3 BR | Available Now
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36
$4,950
Winter Park, FL
4 BR | Available Now
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1
$1,450
1695 Lee Rd Winter Park, FL
2 BR | Available Now
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Pool
Hidden Pond
1
$1,775
Maitland, FL
1 BR | Sep. 1, 2026
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5
$1,395
Winter Park, FL
1 BR | Available Now
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1
$1,995
Winter Park, FL
2 BR | Available Now
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Dishwasher
1
$2,500
521 Ohio St Winter Park, FL
3 BR | Available Now
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Dishwasher
17
$2,395
Winter Park, FL
3 BR | Available Now
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Hidden Pond
1
$2,150
727 Halifax Ave Winter Park, FL
3 BR | Available Now
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1
$2,300
2107 Brookview Dr Winter Park, FL
3 BR | Sep. 10, 2026
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1
$8,295
2234 Howard Dr Winter Park, FL
4 BR | Available Now
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11
$1,844 - 4,038
921 South Orlando Avenue Maitland, FL
1 - 3 BR | Available Now
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In Unit Laundry
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Fitness Center
16
$1,545
Orlando, FL
2 BR | Ask for Availability
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1
$1,250
2500 Lee Rd Unit 145 Winter Park, FL
1 BR | Available Now
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Disability Access
16
$1,250
Winter Park, FL
1 BR | Available Now
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9
$3,500
Orlando, FL
2 BR | Available Now
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70
$1,638 - 7,991
2680 North Orange Orlando, FL
Studio - 3 BR | Available Now
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1 - 30 of 47 Results
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  3. Winter Park
  4. Downtown Winter Park

Winter Park:
August Rent Report

Welcome to the August 2026 Winter Park Apartment Report. In this assessment of the local rental market, Rentable data scientists and rental experts break down the August 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

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Sep. 2025
Oct. 2025
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Dec. 2025
Jan. 2026
Feb. 2026
Mar. 2026
Apr. 2026
May. 2026
Jun. 2026
Jul. 2026
Aug. 2026
1 BR       2 BR

Winter Park Rent Prices Decrease From July to August

Winter Park rent prices decreased over the last month. From July to August, 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 July to August, 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 $.

August 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.

August 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 August 1 BR M/M % Change 2 BR August 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.