Apartments in Downtown Winter Park

1 - 30 of 62 Results
1
$3,225
1835 Edwin Blvd Winter Park, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
1
$1,600
130 N Center St Winter Park, FL
1 BR | Available Now
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Dog Friendly
Cat Friendly
Air Conditioning
Dishwasher
Downtown Winter Park
17
$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
58
$4,850
Winter Park, FL
2 BR | Available Now
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Downtown Winter Park
1
$3,700
640 Park Ave #3 Winter Park, FL
2 BR | Available Now
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House
Storage
Pool
Downtown Winter Park
9
$2,100
Winter Park, FL
2 BR | Available Now
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Downtown Winter Park
37
$3,400
Winter Park, FL
2 BR | Available Now
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1
$2,450
939 Aragon Ave Winter Park, FL
2 BR | Available Now
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Cat Friendly
House
Disability Access
Dishwasher
1
$2,040
1308 S Pennsylvania Ave Winter Park, FL
1 BR | Available Now
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Cat Friendly
Dishwasher
1
$1,995
931 Cypress Ave Winter Park, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
56
$3,295
Winter Park, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
1
$3,295
1807 N Park Ave Winter Park, FL
3 BR | Available Now
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Cat Friendly
House
1
$3,995
1166 Palmer Ave Winter Park, FL
3 BR | Available Now
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Cat Friendly
House
Storage
15
$2,795
Winter Park, FL
3 BR | Available Now
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House
36
$1,733 - 7,648
1305 Morgan Stanley Ave Winter Park, FL
Studio - 3 BR | Available Now
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Dog Friendly
Cat Friendly
Luxury
Air Conditioning
Covered Parking
6
$1,299
Winter Park, FL
2 BR | Available Now
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1
$2,595
447 N Phelps Ave Winter Park, FL
3 BR | Available Now
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Cat Friendly
House
Dishwasher
1
$5,250
1610 Lyndale Blvd Maitland, FL
4 BR | Available Now
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Dishwasher
18
$2,395
Winter Park, FL
3 BR | Available Now
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Hidden Pond
1
$2,395
1148 Park Grn Winter Park, FL
3 BR | Available Now
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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
$3,000
Winter Park, FL
3 BR | Available Now
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36
$3,400
Winter Park, FL
3 BR | Dec. 13, 2025
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Dog Friendly
House
Balcony/Deck/Patio
Storage
Dishwasher
29
$16,550
Winter Park, FL
8+ BR | Available Now
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House
Balcony/Deck/Patio
Storage
Dishwasher
19
$3,000
Winter Park, FL
3 BR | Available Now
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Dog Friendly
House
Hidden Pond
2
$1,200
Maitland, FL
1 BR | Available Now
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Dog Friendly
House
Air Conditioning
Hidden Pond
15
$3,295
Winter Park, FL
3 BR | Available Now
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Cat Friendly
House
34
$4,000
Orlando, FL
2 BR | Available Now
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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.