Apartments in Downtown Winter Park

1 - 30 of 48 Results
13
$840
Winter Park, FL
1 BR | Ask for Availability
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18
$882
Winter Park, FL
1 BR | Ask for Availability
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24
$9,500
Winter Park, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
Balcony/Deck/Patio
Storage
Dishwasher
15
$1,010 - 1,680
311 N Knowles Ave Winter Park, FL
Studio - 2 BR | Available Now
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Dog Friendly
Cat Friendly
Section 8
Air Conditioning
Covered Parking
20
$3,600
Winter Park, FL
2 BR | Available Now
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42
$3,149 - 3,295
Winter Park, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
1
$3,149
1807 N Park Ave Winter Park, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
24
$3,950
Winter Park, FL
3 BR | Available Now
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1
$6,995
1350 Lyndale Blvd Winter Park, FL
4 BR | Available Now
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House
36
$1,564 - 4,621
1305 Morgan Stanley Ave Winter Park, FL
Studio - 2 BR | Available Now
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Dog Friendly
Cat Friendly
Luxury
Air Conditioning
Covered Parking
33
$1,250
Winter Park, FL
3 BR | Available Now
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Balcony/Deck/Patio
Dishwasher
Orwin Manor
18
$2,395
Winter Park, FL
3 BR | Available Now
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Hidden Pond
1
$2,250
1148 Park Grn Winter Park, FL
3 BR | Available Now
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House
Storage
Dishwasher
Hidden Pond
36
$4,950
Winter Park, FL
4 BR | Available Now
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11
$3,800
Winter Park, FL
4 BR | Available Now
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14
$2,400
Winter Park, FL
2 BR | Available Now
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Dog Friendly
Cat Friendly
House
Balcony/Deck/Patio
Storage
1
$2,999
1777 Indiana Ave Unit B Winter Park, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
29
$15,550
Winter Park, FL
8+ BR | Available Now
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House
Balcony/Deck/Patio
Storage
Dishwasher
34
$4,000
Orlando, FL
2 BR | Available Now
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Highland Lakes
19
$5,500
Winter Park, FL
3 BR | Available Now
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House
Storage
Dishwasher
60
$20,000
Maitland, FL
4 BR | Available Now
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Dog Friendly
House
Air Conditioning
Balcony/Deck/Patio
Dishwasher
11
$1,844 - 4,038
921 South Orlando Avenue Maitland, FL
1 - 3 BR | Available Now
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Dog Friendly
Cat Friendly
In Unit Laundry
Balcony/Deck/Patio
Fitness Center
16
$1,270
Winter Park, FL
2 BR | Available Now
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Dog Friendly
Cat Friendly
29
$2,275
Maitland, FL
3 BR | Available Now
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11
$1,200
Maitland, FL
1 BR | Available Now
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1
$1,925
942 Gloriosa Ave Winter Park, FL
2 BR | Apr. 27, 2026
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Dog Friendly
Cat Friendly
House
Balcony/Deck/Patio
Storage
70
$1,679 - 9,816
2680 North Orange Orlando, FL
Studio - 3 BR | Available Now
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Dog Friendly
Cat Friendly
Luxury
Air Conditioning
Covered Parking
1
$2,000
12 E. Preston Orlando, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
$1,020 - 1,635
2000 Village Ln Winter Park, FL
1 - 3 BR | Available Now
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Dog Friendly
Cat Friendly
Air Conditioning
Covered Parking
Balcony/Deck/Patio
1
$1,425
121 E Evans St Orlando, FL
2 BR | Available Now
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House
North Orange
1 - 30 of 48 Results
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Winter Park:
February Rent Report

Welcome to the February 2026 Winter Park Apartment Report. In this assessment of the local rental market, Rentable data scientists and rental experts break down the February 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
Mar. 2025
Apr. 2025
May. 2025
Jun. 2025
Jul. 2025
Aug. 2025
Sep. 2025
Oct. 2025
Nov. 2025
Dec. 2025
Jan. 2026
Feb. 2026
1 BR       2 BR

Winter Park Rent Prices Decrease From January to February

Winter Park rent prices decreased over the last month. From January to February, 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 January to February, 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 $.

February 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.

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