Winter Park, FL Homes for Sale & Real Estate

Winter Park, Orlando
$950,000
$366
/ ft²
For Sale
3
Bed
3
Bath
2,599
ft²
$366
/ ft²
Condo, Listed Feb 28th, 2021
$10,406 / mo
Expenses
No data
Cap Rate
Listed Feb 28th, 2021
Fontainbleau, Winter Park, Orlando
$990,000
$313
/ ft²
For Sale
4
Bed
3.5
Bath
3,158
ft²
$313
/ ft²
House, Listed Feb 28th, 2021
$6,178 / mo
Expenses
No data
Cap Rate
Listed Feb 28th, 2021
Lakeside Manor Apartments, Winter Park, Orlando
$131,500
$155
/ ft²
For Sale
2
Bed
1
Bath
851
ft²
$155
/ ft²
Condo, Listed Feb 28th, 2021
$1,781 / mo
Expenses
No data
Cap Rate
Listed Feb 28th, 2021
Shadow Hill, Winter Park, Orlando
$3,150,000
For Sale
Land, Updated 1 day ago
$36,819 / mo
Expenses
-13.79%
Cap Rate
Bedrooms: 0 to -1
Winter Park, Orlando
$850,000
$311
/ ft²
For Sale
3
Bed
3.5
Bath
2,734
ft²
$311
/ ft²
Condo, Listed Feb 26th, 2021
$10,772 / mo
Expenses
No data
Cap Rate
Listed Feb 26th, 2021
Sorenson Heights, Winter Park, Orlando
$829,000
$345
/ ft²
For Sale
4
Bed
3
Bath
2,403
ft²
$345
/ ft²
House, Listed Feb 26th, 2021
$6,655 / mo
Expenses
No data
Cap Rate
Listed Feb 26th, 2021
Villa Siena Condominiums, Winter Park, Orlando
$1,425,000
$508
/ ft²
For Sale
3
Bed
3.5
Bath
2,806
ft²
$508
/ ft²
Condo, Updated 4 days ago
$20,087 / mo
Expenses
-14.93%
Cap Rate
Price dropped $30,000
Lake Virgina Condominiums, Winter Park, Orlando
$379,000
$330
/ ft²
For Sale
2
Bed
2
Bath
1,148
ft²
$330
/ ft²
Condo, Listed Feb 24th, 2021
$4,146 / mo
Expenses
No data
Cap Rate
Listed Feb 24th, 2021
Sandlewood Creek, Winter Park, Orlando
$195,000
$178
/ ft²
For Sale
2
Bed
2.5
Bath
1,098
ft²
$178
/ ft²
Condo, Listed Feb 26th, 2021
$610 / mo
Expenses
No data
Cap Rate
Listed Feb 26th, 2021
Seville Park, Winter Park, Orlando
$475,000
$263
/ ft²
For Sale
2
Bed
2.5
Bath
1,808
ft²
$263
/ ft²
Townhouse, Updated 3 days ago
$2,867 / mo
Expenses
No data
Cap Rate
Amenities Updated
Casa Cielo Condominiums, Winter Park, Orlando
$389,000
$195
/ ft²
For Sale
3
Bed
2.5
Bath
2,000
ft²
$195
/ ft²
Townhouse, Listed Feb 25th, 2021
$4,494 / mo
Expenses
No data
Cap Rate
Listed Feb 25th, 2021
Conwill Estates, Winter Park, Orlando
$493,200
$260
/ ft²
For Sale
4
Bed
2
Bath
1,899
ft²
$260
/ ft²
House, Updated 3 days ago
$5,420 / mo
Expenses
No data
Cap Rate
Listed Feb 24th, 2021
Winter Park, Orlando
$1,595,000
$503
/ ft²
For Sale
3
Bed
3.5
Bath
3,174
ft²
$503
/ ft²
Condo, Updated 1 week ago
$16,368 / mo
Expenses
-10.62%
Cap Rate
Real Estate Tax: 16572 to 16293.34
Winter Park, Orlando
$1,575,000
$643
/ ft²
For Sale
2
Bed
3
Bath
2,450
ft²
$643
/ ft²
Condo, Updated 2 weeks ago
$21,109 / mo
Expenses
-14.69%
Cap Rate
Price dropped $15,000
Cherokee Park, Winter Park, Orlando
$700,000
$297
/ ft²
For Sale
3
Bed
2.5
Bath
2,358
ft²
$297
/ ft²
House, Updated 1 week ago
$7,675 / mo
Expenses
-8.98%
Cap Rate
Price dropped $25,000
Mead Garden Condominiums, Winter Park, Orlando
$199,900
$226
/ ft²
For Sale
2
Bed
2
Bath
884
ft²
$226
/ ft²
Condo, Updated 1 week ago
$1,774 / mo
Expenses
-0.35%
Cap Rate
Price dropped $10,000
Dixie Terrace, Winter Park, Orlando
$1,219,000
$368
/ ft²
For Sale
4
Bed
3.5
Bath
3,317
ft²
$368
/ ft²
House, Updated 1 week ago
$4,010 / mo
Expenses
-1.88%
Cap Rate
Price dropped $31,000
Osceola Court, Winter Park, Orlando
$932,000
$309
/ ft²
For Sale
4
Bed
3.5
Bath
3,019
ft²
$309
/ ft²
House, Updated 3 weeks ago
No data
Expenses
No data
Cap Rate
Listed Jan 21st, 2021
Green Oaks, Winter Park, Orlando
$1,249,000
$548
/ ft²
For Sale
3
Bed
4
Bath
2,281
ft²
$548
/ ft²
House, Updated 1 week ago
$9,473 / mo
Expenses
-7.06%
Cap Rate
Price dropped $46,000
Flora Park, Winter Park, Orlando
$1,399,000
$387
/ ft²
For Sale
4
Bed
4.5
Bath
3,616
ft²
$387
/ ft²
House, Updated 1 week ago
$5,615 / mo
Expenses
-3.01%
Cap Rate
Price dropped $90,000
Maitland Shores, Winter Park, Orlando
$1,700,000
$511
/ ft²
For Sale
4
Bed
3.5
Bath
3,326
ft²
$511
/ ft²
House, Updated 1 week ago
$8,014 / mo
Expenses
No data
Cap Rate
Real Estate Tax: 7956 to 8013.61
Winter Park, Orlando
$469,900
$252
/ ft²
For Sale
3
Bed
2.5
Bath
1,866
ft²
$252
/ ft²
Townhouse, Updated 1 week ago
$4,783 / mo
Expenses
3.43%
Cap Rate
Real Estate Tax: 913.68 to 4714.49
Winter Park, Orlando
$469,900
$252
/ ft²
For Sale
3
Bed
2.5
Bath
1,866
ft²
$252
/ ft²
Townhouse, Updated 1 week ago
$4,789 / mo
Expenses
3.43%
Cap Rate
Real Estate Tax: 913.68 to 4720.4
Winter Park, Orlando
$1,299,000
$366
/ ft²
For Sale
4
Bed
4.5
Bath
3,549
ft²
$366
/ ft²
House, Listed Feb 8th, 2021
$14,108 / mo
Expenses
No data
Cap Rate
Listed Feb 8th, 2021
Sylvan Heights, Winter Park, Orlando
$309,500
$235
/ ft²
For Sale
2
Bed
2
Bath
1,319
ft²
$235
/ ft²
House, Listed Feb 11th, 2021
$1,786 / mo
Expenses
No data
Cap Rate
Listed Feb 11th, 2021
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United States   ›   Florida   ›   Winter Park   ›   Winter Park
Largest Recent Price Drops
1891 OGLESBY AVENUE -$15,000 (-3.8%)
2 E PAR STREET -$10,900 (-2.5%)
1122 NOTTINGHAM STREET -$9,600 (-2.4%)
2015 IVANHOE ROAD -$10,500 (-2.3%)
315 E NEW ENGLAND AVENUE - #15 -$30,000 (-2.1%)
1120 CHICHESTER STREET -$5,000 (-1.2%)
Winter Park currently has 43 residential homes for sale on the market. The median list price is $475,000 or $272 / ft². These listings range from $341,490 in the lower quartile to $1,172,000 in the upper quartile. The average home currently for sale in Winter Park is around 16 years old and 2,000 ft². There are currently 0 studio, 0 one-bedroom, 12 two-bedroom, 17 three-bedroom, and 14 four+ bedroom listings for sale.
A more detailed breakdown of sizes and prices is below:
Median
Bedrooms Price Price / ft²
2 BR $312,245 $196
3 BR $395,000 $252
4+ BR $1,172,000 $367

Out of the 43 listings that are currently on the market, there are 9 condos, 19 houses, 15 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
Casselberry-Altamonte Springs Homes for Sale
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Tax Year: 2018
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