Winter Park Homes For Sale

Winter Park is a city of over 28,000 residents located north of Orlando. This is one of Florida’s finest cities and is famous for its beautiful green spaces, brick-lined streets, spectacular homes, historical museums, vibrant lakes, and fine shops along Park Avenue. The city has maintained its natural beauty throughout the years, making its residents very happy. When people move here, they rarely move away. Rollins College was founded in Winter Park in 1885. The city’s most prominent features include its lakes, tree canopy, bricked streets, shopping/restaurant district on Park Avenue. Central Park is a large, open park featuring large trees, friendly animals, and inviting sitting areas. The city is also famous for the Winter Park Sidewalk Art Festival. This event gets over 250,000 visitors each year to Central Park to enjoy some of the best art and music in the United States. This hub of creativity and class is a must to visit and an amazing place to live!

Open House 05/31 at 10AM
Please verify times due to COVID-19
$380,000
Single Family Home For Sale
Active
3
BED
2
TOTAL BATHS
1,853
SQFT
Address Withheld
Winter Park, FL 32792
 
New Listing - 18 hours online
$900,000
Single Family Home For Sale
Active
0.46
ACRES
ORANGE, FL
COUNTY
200 Oakwood Way
Winter Park, FL 32789
CHARMONT Subdivision
New Listing - 19 hours online
$1,500,000
Single Family Home For Sale
Active
5
BED
6
TOTAL BATHS
5,511
SQFT
1450 Bonnie Burn Circle
Winter Park, FL 32789
BANKS COLONIAL ESTATES Subdivision
New Listing - 21 hours online
$290,000
Townhouse For Sale
Active
3
BED
3
TOTAL BATHS
1,787
SQFT
7619 Aloma Pines Court
Winter Park, FL 32792
ALOMA TRAILS Subdivision
New Listing - 23 hours online
$120,000
Condo For Sale
Active
2
BED
2
TOTAL BATHS
756
SQFT
7241 Swallow Run #7241
Winter Park, FL 32792
WHISPERWOOD CONDO 04 Subdivision
New Listing - 23 hours online
$424,900
Single Family Home For Sale
Active
4
BED
2
TOTAL BATHS
2,358
SQFT
4272 Steed Terrace
Winter Park, FL 32792
KINGS COVE Subdivision
New Listing - 24 hours online
$1,099,000
Single Family Home For Sale
Active
4
BED
4
TOTAL BATHS
3,686
SQFT
495 Jo Al Ca Avenue
Winter Park, FL 32789
GALLOWAY PLACE REP Subdivision
New Listing - yesterday
$919,900
Townhouse For Sale
Active
3
BED
4
TOTAL BATHS
2,341
SQFT
1798 Mondrian Circle
Winter Park, FL 32789
LAKE KILLARNEY TOWNHOMES Subdivision
New Listing - yesterday
$153,000
Condo For Sale
Active
2
BED
2
TOTAL BATHS
1,026
SQFT
1500 Gay Road #9B
Winter Park, FL 32789
CHATEAUX DU LAC Subdivision
New Listing - yesterday
$329,900
Single Family Home For Sale
Active
4
BED
1
TOTAL BATHS
1,100
SQFT
1402 Bessmor Rd Road
Winter Park, FL 32789
WINTER PARK VILLAGE Subdivision
New Listing - yesterday
$245,000
Single Family Home For Sale
Active
3
BED
2
TOTAL BATHS
1,534
SQFT
1436 Auburn Green Loop
Winter Park, FL 32792
COUNTRY LANE Subdivision
New Listing - yesterday
$87,000
Condo For Sale
Active
1
BED
1
TOTAL BATHS
678
SQFT
122 Lewfield Circle #122
Winter Park, FL 32792
STRATFORD A WINTER PARK CONDO Subdivision
New Listing - yesterday
$269,900
Single Family Home For Sale
Active
3
BED
2
TOTAL BATHS
1,393
SQFT
5240 Poinsetta Avenue
Winter Park, FL 32792
WRENWOOD HEIGHTS UNIT 2 Subdivision
New Listing - yesterday
$112,000
Condo For Sale
Active
2
BED
3
TOTAL BATHS
1,230
SQFT
7288 Daniel Webster Drive #5
Winter Park, FL 32792
COLONIES PH 03 Subdivision
Open House 05/31 at 1PM
Please verify times due to COVID-19
$329,900
Single Family Home For Sale
Active
3
BED
2
TOTAL BATHS
1,564
SQFT
2808 Prince John Road
Winter Park, FL 32792
WINTER PARK PINES REP Subdivision
New Listing - yesterday
$778,984
Single Family Home For Sale
Active
5
BED
5
TOTAL BATHS
5,217
SQFT
1193 Wading Waters Circle
Winter Park, FL 32792
HAWK'S CREST Subdivision
New Listing - yesterday
$225,000
Single Family Home For Sale
Active
3
BED
2
TOTAL BATHS
1,432
SQFT
1056 Carnation Drive
Winter Park, FL 32792
EASTBROOK SUB Subdivision
New Listing - yesterday
$537,320
Single Family Home For Sale
Active
5
BED
4
TOTAL BATHS
3,532
SQFT
2123 Laurelwood Way
Winter Park, FL 32792
HAWK'S CREST Subdivision
New Listing - 3 days online
$79,900
Condo For Sale
Active
2
BED
2
TOTAL BATHS
1,085
SQFT
118 Scottsdale Square #118
Winter Park, FL 32792
WINTER PARK WOODS CONDO Subdivision
New Listing - 3 days online
$1,395,000
Single Family Home For Sale
Active
4
BED
6
TOTAL BATHS
4,240
SQFT
360 Cortland Avenue
Winter Park, FL 32789
OSCEOLA SUMMIT Subdivision
New Listing - 3 days online
$215,000
Condo For Sale
Active
2
BED
2
TOTAL BATHS
1,295
SQFT
2487 Tahoe Circle #2487
Winter Park, FL 32792
CEDARWOOD VILLAGE 1 Subdivision
New Listing - 3 days online
$95,000
Condo For Sale
Active
1
BED
1
TOTAL BATHS
776
SQFT
1000 S Semoran Boulevard #S
Winter Park, FL 32792
GOLFSIDE VILLAS CONDO Subdivision
New Listing - 3 days online
$159,000
Condo For Sale
Active
1
BED
1
TOTAL BATHS
772
SQFT
700 Melrose Avenue #K32
Winter Park, FL 32789
WINTER PARK GARDENS CONDO Subdivision
New Listing - 3 days online
$375,000
Single Family Home For Sale
Active
3
BED
2
TOTAL BATHS
1,590
SQFT
1719 Michigan Avenue
Winter Park, FL 32789
LAWNDALE Subdivision
New Listing - 3 days online
$989,000
Single Family Home For Sale
Active
4
BED
4
TOTAL BATHS
3,150
SQFT
1931 Laurel Road
Winter Park, FL 32789
CHARMONT Subdivision
New Listing - 4 days online
$2,385,000
Townhouse For Sale
Active
2
BED
5
TOTAL BATHS
3,244
SQFT
125 S Interlachen Avenue #5
Winter Park, FL 32789
SOUTH INTERLACHEN PLACE Subdivision
New Listing - 4 days online
$3,395,000
Townhouse For Sale
Active
3
BED
5
TOTAL BATHS
4,160
SQFT
125 S Interlachen Avenue #6
Winter Park, FL 32789
SOUTH INTERLACHEN PLACE Subdivision
New Listing - 4 days online
$1,325,000
Single Family Home For Sale
Active
5
BED
4
TOTAL BATHS
3,670
SQFT
1265 Via Lugano
Winter Park, FL 32789
THE VIA'S Subdivision
New Listing - 5 days online
$599,000
Single Family Home For Sale
Active
3
BED
3
TOTAL BATHS
2,493
SQFT
1386 Aloma Avenue
Winter Park, FL 32789
SYLVAN LAKE SHORES Subdivision
New Listing - 5 days online
$249,900
Single Family Home For Sale
Pending
3
BED
3
TOTAL BATHS
1,533
SQFT
3342 Hamlet Loop
Winter Park, FL 32792
VILLAS OF CASSELBERRY PH 4 Subdivision
New Listing - 7 days online
$500,000
Single Family Home For Sale
Active
3
BED
3
TOTAL BATHS
2,631
SQFT
2245 Fairglenn Way
Winter Park, FL 32792
QUAIL RUN Subdivision
New Listing - a week online
$249,900
Single Family Home For Sale
Pending
3
BED
2
TOTAL BATHS
1,148
SQFT
5123 Cypress Court
Winter Park, FL 32792
WRENWOOD HEIGHTS Subdivision
New Listing - a week online
$1,299,000
Single Family Home For Sale
Active
4
BED
5
TOTAL BATHS
3,213
SQFT
1700 Palmer Avenue
Winter Park, FL 32789
JENKINS ADD Subdivision
New Listing - a week online
$379,900
Single Family Home For Sale
Pending
3
BED
2
TOTAL BATHS
2,482
SQFT
237 Blossom Lane
Winter Park, FL 32789
SHORES LAKE KILLARNEY SEC 02 Subdivision
New Listing - a week online
$699,900
Single Family Home For Sale
Active
3
BED
3
TOTAL BATHS
1,914
SQFT
1610 Chestnut Avenue
Winter Park, FL 32789
LAKE KNOWLES TERRACE Subdivision
New Listing - a week online
$1,445,000
Single Family Home For Sale
Active
4
BED
3
TOTAL BATHS
3,350
SQFT
390 Waterfall Lane
Winter Park, FL 32789
FOUNTAINHEAD Subdivision
New Listing - a week online
$1,695,000
Single Family Home For Sale
Active
5
BED
5
TOTAL BATHS
5,048
SQFT
161 Alexander Place
Winter Park, FL 32789
ALEXANDER PLACE Subdivision
New Listing - a week online
$410,000
Single Family Home For Sale
Pending
4
BED
3
TOTAL BATHS
2,176
SQFT
1433 Nottingham Drive
Winter Park, FL 32792
WINTER WOODS UNIT 03 Subdivision
New Listing - a week online
$238,900
Single Family Home For Sale
Pending
3
BED
3
TOTAL BATHS
1,397
SQFT
3416 Hamlet Loop
Winter Park, FL 32792
VILLAS OF CASSELBERRY PH 3 Subdivision
New Listing - a week online
$277,500
Single Family Home For Sale
Pending
3
BED
2
TOTAL BATHS
1,434
SQFT
7548 Dockside Street
Winter Park, FL 32792
WOODCREST UNIT 5 Subdivision
New Listing - a week online
$1,290,000
Single Family Home For Sale
Active
4
BED
4
TOTAL BATHS
3,450
SQFT
1398 Grove Terrace
Winter Park, FL 32789
SYLVAN LAKE SHORES Subdivision
New Listing - a week online
$1,070,000
Single Family Home For Sale
Active
4
BED
4
TOTAL BATHS
3,351
SQFT
211 Cortland Avenue
Winter Park, FL 32789
CORTLAND PARK Subdivision
New Listing - a week online
$65,000
Condo For Sale
Active
1
BED
1
TOTAL BATHS
785
SQFT
125 Scottsdale Square #125
Winter Park, FL 32792
WINTER PARK WOODS CONDO Subdivision
Open House 05/31 at 1PM
Please verify times due to COVID-19
$359,900
Single Family Home For Sale
Active
3
BED
2
TOTAL BATHS
1,847
SQFT
1813 Alice Avenue
Winter Park, FL 32792
LAKEMONT HEIGHTS Subdivision
New Listing - a week online
$675,000
Single Family Home For Sale
Active
4
BED
3
TOTAL BATHS
2,627
SQFT
1400 Canterbury Road
Winter Park, FL 32789
ORWIN MANOR WESTMINSTER SEC Subdivision
New Listing - a week online
$165,000
Condo For Sale
Pending
2
BED
1
TOTAL BATHS
780
SQFT
151 N Orlando Avenue #203
Winter Park, FL 32789
LAKE KILLARNEY CONDO Subdivision
New Listing - a week online
$390,000
Single Family Home For Sale
Active
4
BED
2
TOTAL BATHS
2,358
SQFT
4284 Steed Terrace
Winter Park, FL 32792
KINGS COVE Subdivision
New Listing - a week online
$625,000
Single Family Home For Sale
Active
4
BED
4
TOTAL BATHS
3,013
SQFT
770 Greens Avenue
Winter Park, FL 32789
DUBSDREAD HEIGHTS Subdivision
New Listing - a week online
$385,000
Single Family Home For Sale
Pending
4
BED
3
TOTAL BATHS
1,639
SQFT
1802 Palmer Avenue
Winter Park, FL 32792
LAKEMONT HEIGHTS Subdivision
New Listing - a week online
$419,000
Condo For Sale
Pending
2
BED
1
TOTAL BATHS
901
SQFT
100 S Interlachen Avenue #107F
Winter Park, FL 32789
CLOISTERS CONDO Subdivision
New Listing - a week online
$381,900
Condo For Sale
Active
2
BED
2
TOTAL BATHS
1,340
SQFT
250 Carolina Avenue #201
Winter Park, FL 32789
PARK WEST CONDO Subdivision
New Listing - a week online
$104,900
Condo For Sale
Active
2
BED
1
TOTAL BATHS
881
SQFT
1695 Lee Road #D212
Winter Park, FL 32789
WATERFALL COVE Subdivision
New Listing - a week online
$1,099,000
Single Family Home For Sale
Active
4
BED
4
TOTAL BATHS
4,045
SQFT
1608 Barcelona Way
Winter Park, FL 32789
SEVILLA Subdivision
New Listing - a week online
$315,000
Single Family Home For Sale
Active
3
BED
1
TOTAL BATHS
1,025
SQFT
2353 Mulbry Drive
Winter Park, FL 32789
LAKE FOREST PARK Subdivision
New Listing - a week online
$699,900
Single Family Home For Sale
Active
3
BED
3
TOTAL BATHS
1,939
SQFT
1427 Indiana Avenue
Winter Park, FL 32789
HENKEL ADDITION Subdivision
New Listing - a week online
$944,000
Single Family Home For Sale
Pending
5
BED
5
TOTAL BATHS
4,364
SQFT
2501 Modac Trail
Winter Park, FL 32789
DOMMERICH HILLS FOURTH ADD Subdivision
New Listing - 2 weeks online
$129,900
Condo For Sale
Pending
2
BED
3
TOTAL BATHS
1,031
SQFT
3263 Oak Lake Place #132
Winter Park, FL 32792
HIDDEN OAKS CONDO PH 08 Subdivision
New Listing - 2 weeks online
$250,000
Single Family Home For Sale
Pending
3
BED
2
TOTAL BATHS
1,456
SQFT
765 Carnation Drive
Winter Park, FL 32792
EASTBROOK SUB Subdivision
New Listing - 2 weeks online
$324,900
Single Family Home For Sale
Pending
3
BED
1
TOTAL BATHS
1,170
SQFT
1816 Alice Avenue
Winter Park, FL 32792
LAKEMONT HEIGHTS Subdivision