Apartments in Downtown Winter Park

1 - 30 of 30 Results
23
$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
$1,895
2529 Pine Pl Winter Park, FL
3 BR | Available Now
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Cat Friendly
House
Dishwasher
Pool
1
$2,500
301 S Capen Ave Winter Park, FL
3 BR | Available Now
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House
Downtown Winter Park
11
$1,950
Winter Park, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
Air Conditioning
Dishwasher
14
$1,995
Winter Park, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
Air Conditioning
1
$2,250
851 Carver St Winter Park, FL
3 BR | Jul. 10, 2026
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1
$3,200
438 Lakeview Ave Winter Park, FL
2 BR | Available Now
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Dog Friendly
Cat Friendly
House
36
$1,821 - 6,196
1305 Morgan Stanley Ave Winter Park, FL
Studio - 3 BR | Available Now
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Luxury
Air Conditioning
Covered Parking
In Unit Laundry
Balcony/Deck/Patio
1
$3,995
Winter Park, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
36
$4,950
Winter Park, FL
4 BR | Available Now
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1
$2,500
521 Ohio St Winter Park, FL
3 BR | Available Now
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Dishwasher
1
$1,550
1140 Lake Maitland Ter #e2 Maitland, FL
1 BR | Available Now
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Pool
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
14
$1,595
Winter Park, FL
2 BR | Available Now
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Dog Friendly
Cat Friendly
House
1
$1,399
2500 Lee Rd Unit 145 Winter Park, FL
1 BR | Available Now
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Disability Access
16
$1,399
Winter Park, FL
1 BR | Available Now
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1
$2,395
5117 Lake Howell Rd Winter Park, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
House
Dishwasher
70
$1,627 - 8,337
2680 North Orange Orlando, FL
Studio - 3 BR | Available Now
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Luxury
Air Conditioning
Covered Parking
In Unit Laundry
Balcony/Deck/Patio
$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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North Orange
16
$1,699 - 1,899
2001 Glenridge Way Winter Park, FL
1 - 2 BR | Available Now
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Dog Friendly
Cat Friendly
Air Conditioning
Surface Parking
Storage
12
$2,950
Winter Park, FL
3 BR | Jul. 1, 2026
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Dog Friendly
Cat Friendly
Balcony/Deck/Patio
Storage
Dishwasher
31
$1,977 - 3,389
190 Independence Ln Maitland, FL
1 - 2 BR | Available Now
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Luxury
Air Conditioning
Covered Parking
Fitness Center
Dishwasher
1
$9,500
4230 Lower Park Rd Orlando, FL
5 BR | Available Now
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Cat Friendly
House
1
$1,895
1 E King St Orlando, FL
3 BR | Available Now
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Dog Friendly
Cat Friendly
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North Orange
1
$1,595
Orlando, FL
2 BR | Available Now
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Cat Friendly
Storage
North Orange
54
$2,268 - 7,960
1884 Lakemont Ave Orlando, FL
Studio - 3 BR | Available Now
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Dog Friendly
Cat Friendly
Luxury
Air Conditioning
Surface Parking
1
$4,150
1816 Prospect Ave Orlando, FL
3 BR | Aug. 25, 2026
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Dog Friendly
Cat Friendly
House
Dishwasher
Pool
15
$621
Maitland, FL
1 BR | Ask for Availability
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1 - 30 of 30 Results
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  3. Winter Park
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Winter Park:
June Rent Report

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

Winter Park Rent Prices Decrease From May to June

Winter Park rent prices decreased over the last month. From May to June, 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 May to June, 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 $.

June 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.

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