Winter Park, FL Homes for Sale

Windsong Lakeside, Winter Park, Orlando
$1,375,000
$308
/ ft²
For Sale
4
Bed
4
Bath
4,461
ft²
$308
/ ft²
House, Updated 17 hours ago
$17,088 / mo
Expenses
0%
Cap Rate
Price dropped $19,999
Winter Park, Orlando
$414,000
$272
/ ft²
For Sale
3
Bed
2
Bath
1,524
ft²
$272
/ ft²
House, Updated 17 hours ago
$4,699 / mo
Expenses
No data
Cap Rate
Price dropped $5,000
Winflor Court, Winter Park, Orlando
$639,900
$337
/ ft²
For Sale
3
Bed
2
Bath
1,899
ft²
$337
/ ft²
House, Updated 17 hours ago
$9,072 / mo
Expenses
No data
Cap Rate
Listed 6 days ago
Fairbanks Park, Winter Park, Orlando
$1,200,000
$382
/ ft²
For Sale
4
Bed
3.5
Bath
3,142
ft²
$382
/ ft²
House, Updated 17 hours ago
$2,591 / mo
Expenses
No data
Cap Rate
Listed 1 week ago
Lake Knowles Terrace, Winter Park, Orlando
$405,000
$375
/ ft²
For Sale
2
Bed
1
Bath
1,080
ft²
$375
/ ft²
House, Updated 17 hours ago
$4,691 / mo
Expenses
No data
Cap Rate
Price dropped $10,000
Forest Hills, Winter Park, Orlando
$379,000
$289
/ ft²
For Sale
2
Bed
1
Bath
1,312
ft²
$289
/ ft²
House, Updated 17 hours ago
$3,829 / mo
Expenses
No data
Cap Rate
Price dropped $20,000
Forest Hills, Winter Park, Orlando
$379,000
For Sale
Stu
0
Bath
Land, Updated 17 hours ago
$3,829 / mo
Expenses
No data
Cap Rate
Price dropped $20,000
Boiley Green, Winter Park, Orlando
$1,575,000
$350
/ ft²
For Sale
4
Bed
4.5
Bath
4,506
ft²
$350
/ ft²
House, Updated 17 hours ago
$10,695 / mo
Expenses
No data
Cap Rate
Listed 2 days ago
Winter Park, Orlando
$650,000
For Sale
Stu
0
Bath
Land, Updated 17 hours ago
$3,687 / mo
Expenses
0%
Cap Rate
Contact Name: Charles Orden to Charlie Orden
Winter Park, Orlando
$499,000
For Sale
Stu
0
Bath
Land, Updated 17 hours ago
$3,687 / mo
Expenses
0%
Cap Rate
Price dropped $51,000
Winter Park, Orlando
$550,000
For Sale
Stu
0
Bath
Land, Updated 17 hours ago
$3,687 / mo
Expenses
0%
Cap Rate
Contact Name: Charles Orden to Charlie Orden
Quarters at Winter Park, Winter Park, Orlando
$439,000
$206
/ ft²
For Sale
3
Bed
2.5
Bath
2,136
ft²
$206
/ ft²
Townhouse, Updated 1 day ago
$2,400 / mo
Expenses
0%
Cap Rate
Price dropped $10,000
Conwill Estates, Winter Park, Orlando
$899,000
$230
/ ft²
For Sale
5
Bed
5
Bath
3,904
ft²
$230
/ ft²
House, Updated 1 day ago
$12,928 / mo
Expenses
0%
Cap Rate
Price dropped $50,000
Dixie Terrace, Winter Park, Orlando
$1,120,000
$322
/ ft²
For Sale
4
Bed
5
Bath
3,478
ft²
$322
/ ft²
House, Updated 1 day ago
$831 / mo
Expenses
1.14%
Cap Rate
Listed 3 days ago
Charmont, Winter Park, Orlando
$749,900
$278
/ ft²
For Sale
3
Bed
3
Bath
2,700
ft²
$278
/ ft²
House, Updated 3 days ago
$4,465 / mo
Expenses
No data
Cap Rate
Amenities Updated
Windsong Lakeside, Winter Park, Orlando
$1,550,000
$324
/ ft²
For Sale
5
Bed
6.5
Bath
4,790
ft²
$324
/ ft²
House, Updated 4 days ago
$19,921 / mo
Expenses
No data
Cap Rate
Listed 6 days ago
Virginia Heights, Winter Park, Orange County
$625,000
$263
/ ft²
For Sale
4
Bed
3
Bath
2,376
ft²
$263
/ ft²
House, Updated 3 days ago
$5,730 / mo
Expenses
0%
Cap Rate
Price dropped $24,500
Lake Knowles Terrace, Winter Park, Orlando
$1,107,750
$312
/ ft²
For Sale
4
Bed
4.5
Bath
3,555
ft²
$312
/ ft²
House, Updated 4 days ago
$8,343 / mo
Expenses
No data
Cap Rate
Listed 6 days ago
Winter Park, Orlando
$624,900
$312
/ ft²
For Sale
3
Bed
4
Bath
2,001
ft²
$312
/ ft²
House, Updated 5 days ago
$2,030 / mo
Expenses
0%
Cap Rate
Price dropped $5,000
Winter Park, Orlando
$599,900
$300
/ ft²
For Sale
3
Bed
4
Bath
2,001
ft²
$300
/ ft²
House, Updated 5 days ago
$2,030 / mo
Expenses
0%
Cap Rate
Price dropped $25,000
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Largest Recent Price Drops
1276 PRESERVE POINT DRIVE -$88,800 (-6.6%)
1421 SUNSET DRIVE -$29,005 (-5.5%)
1725 SPRUCE AVENUE -$50,000 (-5.3%)
200 SAINT ANDREWS BOULEVARD - #3411 -$6,000 (-5.2%)
300 W LAKE SUE AVENUE -$20,000 (-5.0%)
Largest Recent Price Drops
-$88,800 (-6.6%)
4 Bed / 4.5 Bath
2019-02-09
-$29,005 (-5.5%)
3 Bed / 3.5 Bath
-$50,000 (-5.3%)
5 Bed / 5 Bath
-$6,000 (-5.2%)
1 Bed / 1 Bath
-$20,000 (-5.0%)
2 Bed / 1 Bath
-$20,000 (-5.0%)
Stu / 0 Bath
2019-02-14
-$26,900 (-4.9%)
3 Bed / 2 Bath
-$30,000 (-4.1%)
4 Bed / 3 Bath
-$25,000 (-4.0%)
3 Bed / 4 Bath
-$24,500 (-3.8%)
4 Bed / 3 Bath
-$30,000 (-3.1%)
5 Bed / 5 Bath
-$15,000 (-3.0%)
3 Bed / 2.5 Bath
-$20,000 (-2.9%)
4 Bed / 3 Bath
-$10,900 (-2.7%)
Stu / 0 Bath
2019-01-26
-$15,000 (-2.6%)
3 Bed / 3 Bath
2019-02-17
-$10,000 (-2.6%)
4 Bed / 2 Bath
-$19,000 (-2.4%)
3 Bed / 3 Bath
-$10,000 (-2.4%)
2 Bed / 1 Bath
-$24,000 (-2.1%)
4 Bed / 3.5 Bath
-$50,000 (-1.9%)
6 Bed / 6.5 Bath
-$10,100 (-1.8%)
3 Bed / 3 Bath
-$15,000 (-1.8%)
3 Bed / 2 Bath
-$4,900 (-1.7%)
2 Bed / 1.5 Bath
-$6,000 (-1.7%)
2 Bed / 1 Bath
-$19,999 (-1.4%)
4 Bed / 4 Bath
-$9,100 (-1.4%)
4 Bed / 3 Bath
-$5,000 (-1.2%)
3 Bed / 2 Bath
-$5,000 (-1.2%)
3 Bed / 2 Bath
-$5,000 (-1.2%)
3 Bed / 2 Bath
-$5,000 (-0.8%)
3 Bed / 4 Bath
-$5,000 (-0.8%)
3 Bed / 4 Bath
-$5,000 (-0.4%)
4 Bed / 4 Bath
-$10 (-0.0%)
5 Bed / 8 Bath
Winter Park currently has 141 residential homes for sale on the market. The median list price is $743,900 or $297 / ft². These listings range from $399,900 in the lower quartile to $1,295,000 in the upper quartile. The average home currently for sale in Winter Park is around 47 years old and 2,293 ft². There are currently 15 studio, 2 one-bedroom, 20 two-bedroom, 37 three-bedroom, and 67 four+ bedroom listings for sale.
A more detailed breakdown of sizes and prices is below:
Median
Bedrooms Price Price / ft²
Studio $550,000 $0
1 BR $101,000 $124
2 BR $280,000 $272
3 BR $499,995 $275
4+ BR $1,200,000 $324

Out of the 141 listings that are currently on the market, there are 20 condos, 100 houses, 6 townhouses, and 0 multifamilies. Our real-time inventory refreshes every hour, so that you see the best new inventory available on the market.

This search area is located within Orange County, Florida. Orange County, Florida has 1,256,055 residents in 444,852 households. The median age of this county is 34.5 with a majority of inhabitants unmarried. At least 54.27% of those living in this county currently own their homes. Roughly 28.60% of population here speak a language other than English at home.

The median income in this county is $49,391, with an employment rate of 61.9%. It tends to take those living in Orange County, Florida an average of 27.1 minutes to get to work, with a majority commuting by car. Out of the total population of those 25 and older, 10.61% have a master’s or above, 21.32% have a bachelor’s, and 25.74% have a high school degree.

More broadly, Orange County, Florida is a part of the Orlando, FL Urban Area. The Orlando, FL Urban Area has around 1,639,556 residents, or 580,594 households with a median age of 35.7. Residents in this urban area have a median income of $51,507 and a home ownership rate of 57.57%.

Searching on Zillow Winter Park, Trulia, or Realtor.com? RealtyHop has the most comprehensive mortgage and property record data to help you make the best buying decision.

Nearby Counties & Divisions
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Maintenance
HOA dues, common charges, etc.
month
year
Property Taxes
Tax Year: 2018
month
year