Winter Park, FL Homes for Sale & Real Estate

Winter Park, Orlando
$999,000
$337
/ ft²
For Sale
3
Bed
2.5
Bath
2,965
ft²
$337
/ ft²
House, Updated 10 hours ago
$6,058 / mo
Expenses
No data
Cap Rate
Price dropped $51,000
Sicilian Shores, Winter Park, Orlando
$3,199,000
$454
/ ft²
For Sale
6
Bed
9
Bath
7,048
ft²
$454
/ ft²
House, Updated 10 hours ago
$33,779 / mo
Expenses
No data
Cap Rate
Listed 3 days ago
Winter Park, Orlando
$575,000
$293
/ ft²
For Sale
4
Bed
2.5
Bath
1,965
ft²
$293
/ ft²
House, Updated 1 day ago
$2,050 / mo
Expenses
No data
Cap Rate
Price dropped $14,999
Osceola Heights, Winter Park, Orlando
$493,000
$272
/ ft²
For Sale
3
Bed
2.5
Bath
1,810
ft²
$272
/ ft²
House, Updated 1 day ago
$3,903 / mo
Expenses
No data
Cap Rate
Price dropped $1,000
Winter Park Village, Winter Park, Orlando
$218,500
$190
/ ft²
For Sale
3
Bed
2
Bath
1,150
ft²
$190
/ ft²
House, Updated 1 day ago
$2,430 / mo
Expenses
No data
Cap Rate
Price dropped $11,500
Winter Park, Orlando
$435,000
$194
/ ft²
For Sale
4
Bed
2.5
Bath
2,247
ft²
$194
/ ft²
House, Updated 2 days ago
$4,619 / mo
Expenses
No data
Cap Rate
Listed 1 week ago
Winter Park, Orlando
$1,245,000
$227
/ ft²
For Sale
5
Bed
6
Bath
5,474
ft²
$227
/ ft²
House, Updated 5 days ago
$15,078 / mo
Expenses
No data
Cap Rate
Price dropped $50,000
Park Green, Winter Park, Orlando
$179,000
$145
/ ft²
For Sale
3
Bed
2
Bath
1,235
ft²
$145
/ ft²
Townhouse, Updated 3 days ago
$2,209 / mo
Expenses
No data
Cap Rate
Listed 6 days ago
Waterfall Cove at Winter Park, Winter Park, Orlando
$94,900
$108
/ ft²
For Sale
2
Bed
1
Bath
881
ft²
$108
/ ft²
Condo, Updated 3 days ago
$915 / mo
Expenses
No data
Cap Rate
Price dropped $5,000
Windsong Preserve Point, Windsong, Winter Park, Orlando
$4,500,000
$728
/ ft²
For Sale
4
Bed
4.5
Bath
6,179
ft²
$728
/ ft²
House, Updated 4 days ago
$48,607 / mo
Expenses
No data
Cap Rate
Listed 6 days ago
Conwill Estates, Winter Park, Orlando
$949,900
$288
/ ft²
For Sale
5
Bed
3
Bath
3,297
ft²
$288
/ ft²
House, Updated 4 days ago
$8,629 / mo
Expenses
No data
Cap Rate
Listed 6 days ago
Dixie Terrace, Winter Park, Orlando
$639,000
$506
/ ft²
For Sale
3
Bed
2
Bath
1,263
ft²
$506
/ ft²
House, Updated 5 days ago
$5,901 / mo
Expenses
No data
Cap Rate
Listed 1 week ago
Waterbridge, Winter Park, Orlando
$350,000
$212
/ ft²
For Sale
2
Bed
3
Bath
1,650
ft²
$212
/ ft²
Townhouse, Updated 4 days ago
$232 / mo
Expenses
3.83%
Cap Rate
Listed 2 weeks ago
Orwin Manor Westminster, Winter Park, Orlando
$835,000
$560
/ ft²
For Sale
4
Bed
3
Bath
1,491
ft²
$560
/ ft²
House, Updated 4 days ago
$3,392 / mo
Expenses
No data
Cap Rate
Listed 1 week ago
Virginia Heights, Winter Park, Orlando
$935,000
$301
/ ft²
For Sale
5
Bed
3.5
Bath
3,104
ft²
$301
/ ft²
House, Updated 1 week ago
$4,498 / mo
Expenses
No data
Cap Rate
Listed 5 weeks ago
Temple Estates, Winter Park, Orlando
$1,325,000
$409
/ ft²
For Sale
4
Bed
4.5
Bath
3,238
ft²
$409
/ ft²
House, Updated 1 week ago
$4,976 / mo
Expenses
No data
Cap Rate
Listed 4 weeks ago
Eastgate, Winter Park, Orlando
$169,900
$186
/ ft²
For Sale
Stu
0
Bath
912
ft²
$186
/ ft²
Commercial, Updated 1 week ago
$8,549 / mo
Expenses
No data
Cap Rate
Listed 1 week ago
Kenilworth Shores, Winter Park, Orlando
$349,000
$206
/ ft²
For Sale
3
Bed
2.5
Bath
1,698
ft²
$206
/ ft²
House, Updated 1 week ago
$4,641 / mo
Expenses
No data
Cap Rate
Price dropped $10,000
Killarney Estates, Winter Park, Orlando
$299,000
$306
/ ft²
For Sale
2
Bed
1
Bath
976
ft²
$306
/ ft²
House, Updated 1 week ago
$1,731 / mo
Expenses
No data
Cap Rate
Price increased $1,000
Charmont, Winter Park, Orlando
$825,000
For Sale
Stu
0
Bath
Land, Updated 1 week ago
$8,657 / mo
Expenses
No data
Cap Rate
Price dropped $24,000
Albert Lee Ridge, Winter Park, Orlando
$549,900
$209
/ ft²
For Sale
Stu
0
Bath
2,636
ft²
$209
/ ft²
Commercial, Updated 1 week ago
$4,195 / mo
Expenses
No data
Cap Rate
Amenities Updated
Winter Park Old Town, Winter Park, Orlando
$6,500,000
For Sale
Stu
0
Bath
Land, Updated 2 weeks ago
$40,420 / mo
Expenses
0%
Cap Rate
Price dropped $400,000
Winter Park, Orlando
$100,000
For Sale
Stu
0
Bath
Land, Updated 2 weeks ago
$652 / mo
Expenses
No data
Cap Rate
Price dropped $15,000
Kenilworth Shores, Winter Park, Orlando
$475,500
$311
/ ft²
For Sale
3
Bed
2
Bath
1,528
ft²
$311
/ ft²
House, Updated 1 week ago
$1,232 / mo
Expenses
No data
Cap Rate
Amenities Updated
Conwill Estates, Winter Park, Orlando
$340,000
$283
/ ft²
For Sale
3
Bed
2
Bath
1,202
ft²
$283
/ ft²
House, Updated 1 week ago
$4,271 / mo
Expenses
No data
Cap Rate
Listed 2 weeks ago
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United States   ›   Florida   ›   Winter Park   ›   Winter Park
Largest Recent Price Drops
1814 HAMMERLIN AVENUE -$20,000 (-7.2%)
551 FINCHLEY ROAD -$10,000 (-5.9%)
506 RUFFEL STREET -$9,000 (-5.7%)
2710 Middlesex Road -$40,100 (-5.3%)
1695 LEE ROAD - #E203 -$5,000 (-5.0%)
Winter Park currently has 101 residential homes for sale on the market. The median list price is $579,990 or $283 / ft². These listings range from $350,000 in the lower quartile to $1,130,000 in the upper quartile. The average home currently for sale in Winter Park is around 35 years old and 2,140 ft². There are currently 5 studio, 0 one-bedroom, 19 two-bedroom, 30 three-bedroom, and 47 four+ bedroom listings for sale.
A more detailed breakdown of sizes and prices is below:
Median
Bedrooms Price Price / ft²
Studio $358,900 $293
2 BR $260,000 $212
3 BR $472,450 $262
4+ BR $1,050,000 $309

Out of the 101 listings that are currently on the market, there are 14 condos, 76 houses, 6 townhouses, and 1 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
Casselberry-Altamonte Springs Homes for Sale
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Maintenance
HOA dues, common charges, etc.
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Property Taxes
Tax Year: 2018
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