Apartments in Downtown Winter Park

31 - 60 of 62 Results
10
$3,200
Orlando, FL
3 BR | Dec. 15, 2025
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Air Conditioning
Dishwasher
Highland Lakes
21
$4,200
Maitland, FL
2 BR | Dec. 14, 2025
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Dog Friendly
Cat Friendly
Balcony/Deck/Patio
Storage
Dishwasher
60
$25,000
Maitland, FL
4 BR | Available Now
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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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Cat Friendly
In Unit Laundry
Balcony/Deck/Patio
Fitness Center
16
$1,345
Winter Park, FL
2 BR | Available Now
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Dog Friendly
Cat Friendly
43
$2,500
Winter Park, FL
3 BR | Available Now
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Cat Friendly
House
Hidden Pond
1
$2,500
929 Dupont Ave Winter Park, FL
3 BR | Available Now
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Cat Friendly
House
Hidden Pond
29
$2,275
Maitland, FL
3 BR | Available Now
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1
$1,795
918 Gloriosa Ave Winter Park, FL
3 BR | Available Now
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House
1
$2,200
313 Granada Dr Winter Park, FL
4 BR | Available Now
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Dog Friendly
Cat Friendly
House
70
$1,638 - 8,156
2680 North Orange Orlando, FL
Studio - 3 BR | Available Now
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Dog Friendly
Cat Friendly
Luxury
Air Conditioning
Covered Parking
40
$2,695
Maitland, FL
4 BR | Available Now
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House
Air Conditioning
Dishwasher
$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
$1,290
64 Taylor Ave Eatonville, FL
2 BR | Available Now
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House
1
$1,750
2045 S Lakemont Ave Winter Park, FL
2 BR | Available Now
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Dog Friendly
Cat Friendly
Disability Access
Dishwasher
5
$1,350
Orlando, FL
1 BR | Available Now
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Dog Friendly
Cat Friendly
House
Dishwasher
North Orange
23
$835
Eatonville, FL
1 BR | Ask for Availability
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24
$2,900
Orlando, FL
3 BR | Available Now
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North Orange
1
$1,100
41 E Winter Park St Orlando, FL
1 BR | Available Now
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Dog Friendly
Cat Friendly
North Orange
1
$1,595
Orlando, FL
2 BR | Available Now
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Cat Friendly
Storage
North Orange
1
$1,675
3119 Harrison Ave Orlando, FL
2 BR | Available Now
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Dog Friendly
Cat Friendly
House
1
$2,795
100 E Orlando St Orlando, FL
3 BR | Available Now
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Cat Friendly
House
Dishwasher
North Orange
1
$3,500
2011 Meeting Pl Orlando, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
Storage
Pool
40
$2,075 - 4,731
1884 Lakemont Ave Orlando, FL
Studio - 3 BR | Available Now
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Dog Friendly
Cat Friendly
Luxury
Air Conditioning
Surface Parking
1
$2,200
1931 Carrigan Ave Winter Park, FL
3 BR | Feb. 13, 2026
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Dog Friendly
Cat Friendly
House
Storage
Dishwasher
1
$3,240
226 W Spruce St Orlando, FL
4 BR | Dec. 6, 2025
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Dog Friendly
Cat Friendly
House
39
$3,240
Orlando, FL
4 BR | Dec. 6, 2025
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6
$1,095
Maitland, FL
2 BR | Dec. 20, 2025
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Air Conditioning
13
$1,695
Winter Park, FL
2 BR | Available Now
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Air Conditioning
Balcony/Deck/Patio
Dishwasher
1
$1,500
101 Lewfield Dr Winter Park, FL
2 BR | Available Now
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Dog Friendly
Cat Friendly
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31 - 60 of 62 Results
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Winter Park:
December Rent Report

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

Winter Park Rent Prices Decrease From November to December

Winter Park rent prices decreased over the last month. From November to December, 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 November to December, 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 $.

December 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.

December 2025 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 December 1 BR M/M % Change 2 BR December 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.