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Winter Park Real Estate Analysis

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Winter Park’s roots go back to the late 19th century, when it was established as a resort town catering to well-to-do northerners fleeing harsh New England winters. Charmed by the planned community’s natural beauty and architectural aesthetics, President Chester A. Arthur pronounced Winter Park to be “the prettiest place I have seen in Florida.”
Although a lot has changed in Winter Park since the 1880s, the visual charm of majestic, moss-draped oak trees, beautiful lakes, and classic Florida buildings still makes it one of Central Florida’s most desirable locations to live and work.
That sense of history is a point of pride for many Winter Park residents, but the city is far from being a museum piece (although there are several notable museums in town). A vibrant student community infuses Winter Park with a youthful energy that complements the classic views and high-end shopping; along with Full Sail University, Winter Park is also home to the private, liberal-arts-focused Rollins College, which was established as Florida’s first four-year college in 1885. Those two schools bring the city’s student population to nearly 10,000.
Due to Winter Park’s proximity to downtown Orlando (the two cities’ cores are separated by less than a 10-minute drive), residents of Winter Park are also ideally situated to take advantage of the offerings at the Orlando Museum of Art, the Orlando Shakespeare Theatre, the Orlando Ballet, the Orlando Philharmonic Orchestra, and many more cultural outlets.
To find homes in Winter Park, use our Real Estate Search with zip code 32789 and 32792.

Winter Park Real Estate Listings

Active Listings in Winter Park

1344 Indiana Avenue WINTER PARK, FL 32789
Photo of 1344 Indiana Avenue, WINTER PARK, FL 32789 (MLS # O5819166)
5 beds 4 baths 2,950 sqft $995,000
470 Killarney Bay Court, Unit 7 WINTER PARK, FL 32789
Photo of 470 Killarney Bay Court, Unit 7, WINTER PARK, FL 32789 (MLS # O5818772)
2 beds 2 baths 1,160 sqft $295,000
7100 Betty Street WINTER PARK, FL 32792
Photo of 7100 Betty Street, WINTER PARK, FL 32792 (MLS # O5818986)
6 beds 3 baths 2,690 sqft $340,000
1608 Barcelona Way WINTER PARK, FL 32789
Photo of 1608 Barcelona Way, WINTER PARK, FL 32789 (MLS # O5818957)
4 beds 4 baths 4,045 sqft $1,150,000
3119 Crown Jewel Court WINTER PARK, FL 32792
Photo of 3119 Crown Jewel Court, WINTER PARK, FL 32792 (MLS # O5818933)
3 beds 3 baths 1,442 sqft $233,900
712 W Comstock Avenue WINTER PARK, FL 32789
Photo of 712 W Comstock Avenue, WINTER PARK, FL 32789 (MLS # O5818923)
2 beds 1 bath 750 sqft $325,000
3326 Australian Circle WINTER PARK, FL 32792
Photo of 3326 Australian Circle, WINTER PARK, FL 32792 (MLS # O5818910)
3 beds 2 baths 1,705 sqft $235,000
311 E Morse Boulevard, Unit 6-20 WINTER PARK, FL 32789
Photo of 311 E Morse Boulevard, Unit 6-20, WINTER PARK, FL 32789 (MLS # O5818543)
1 bed 1 bath 1,137 sqft $425,000
622 Saint Dunstan Way, Unit 7 WINTER PARK, FL 32792
Photo of 622 Saint Dunstan Way, Unit 7, WINTER PARK, FL 32792 (MLS # O5818006)
4 beds 2 baths 1,774 sqft $325,000
601 Berwick Drive, Unit 2 WINTER PARK, FL 32792
Photo of 601 Berwick Drive, Unit 2, WINTER PARK, FL 32792 (MLS # O5818640)
5 beds 3 baths 2,384 sqft $555,000
1963 Japonica Road WINTER PARK, FL 32792
Photo of 1963 Japonica Road, WINTER PARK, FL 32792 (MLS # O5818618)
4 beds 2 baths 2,004 sqft $409,900
4865 N Orange Avenue WINTER PARK, FL 32792
Photo of 4865 N Orange Avenue, WINTER PARK, FL 32792 (MLS # O5818619)
3 beds 1 bath 1,526 sqft $245,000
2615 Oglesby Avenue WINTER PARK, FL 32789
Photo of 2615 Oglesby Avenue, WINTER PARK, FL 32789 (MLS # O5818509)
7 beds 8 baths 6,700 sqft $2,650,000
1241 Richmond Road WINTER PARK, FL 32789
Photo of 1241 Richmond Road, WINTER PARK, FL 32789 (MLS # O5817478)
3 beds 3 baths 2,546 sqft $674,900
1148 Howell Branch Road WINTER PARK, FL 32789
Photo of 1148 Howell Branch Road, WINTER PARK, FL 32789 (MLS # O5817076)
4 beds 2 baths 1,948 sqft $389,500

Sold Listings in Winter Park

340 Cherokee Lane WINTER PARK, FL 32789
Photo of 340 Cherokee Lane, WINTER PARK, FL 32789 (MLS # J908347)
3 beds 4 baths 3,324 sqft $1,500,000
937 S Pennsylvania Avenue WINTER PARK, FL 32789
Photo of 937 S Pennsylvania Avenue, WINTER PARK, FL 32789 (MLS # O5817572)
4 beds 2 baths 1,488 sqft $399,000
1020 Minnesota Avenue, Unit 7 WINTER PARK, FL 32789
Photo of 1020 Minnesota Avenue, Unit 7, WINTER PARK, FL 32789 (MLS # O5785265)
3 beds 4 baths 2,000 sqft $2,200
MLS # O5805683 WINTER PARK, FL 32792
Photo of WINTER PARK, FL 32792 (MLS # O5805683)
5 beds 2 baths 2,707 sqft $654,000
MLS # O5798297 WINTER PARK, FL 32792
Photo of WINTER PARK, FL 32792 (MLS # O5798297)
2 beds 2 baths 1,120 sqft $155,000
1546 Minnesota Avenue WINTER PARK, FL 32789
Photo of 1546 Minnesota Avenue, WINTER PARK, FL 32789 (MLS # O5812314)
3 beds 2 baths 1,125 sqft $275,000
625 Blairshire Circle, Unit NO WINTER PARK, FL 32792
Photo of 625 Blairshire Circle, Unit NO, WINTER PARK, FL 32792 (MLS # O5811891)
4 beds 3 baths 1,835 sqft $270,000
640 N Park Avenue, Unit 37 WINTER PARK, FL 32789
Photo of 640 N Park Avenue, Unit 37, WINTER PARK, FL 32789 (MLS # O5807058)
2 beds 2 baths 858 sqft $1,850
MLS # O5784711 WINTER PARK, FL 32792
Photo of WINTER PARK, FL 32792 (MLS # O5784711)
3 beds 2 baths 1,398 sqft $260,000
131 Scottsdale Square, Unit 131 WINTER PARK, FL 32792
Photo of 131 Scottsdale Square, Unit 131, WINTER PARK, FL 32792 (MLS # O5810198)
2 beds 2 baths 1,020 sqft $83,000
2700 Wright Avenue WINTER PARK, FL 32789
Photo of 2700 Wright Avenue, WINTER PARK, FL 32789 (MLS # J907522)
3 beds 2 baths 1,608 sqft $550,000
446 Melrose Avenue WINTER PARK, FL 32789
Photo of 446 Melrose Avenue, WINTER PARK, FL 32789 (MLS # O5807102)
3 beds 2 baths 2,640 sqft $749,000
2207 Mallard Circle WINTER PARK, FL 32789
Photo of 2207 Mallard Circle, WINTER PARK, FL 32789 (MLS # O5800886)
4 beds 3 baths 2,137 sqft $539,000
2645 Abbey Road WINTER PARK, FL 32792
Photo of 2645 Abbey Road, WINTER PARK, FL 32792 (MLS # O5779104)
3 beds 3 baths 1,685 sqft $320,000
721 W Swoope Avenue WINTER PARK, FL 32789
Photo of 721 W Swoope Avenue, WINTER PARK, FL 32789 (MLS # O5804412)
2 beds 1 bath 962 sqft $265,000

Winter Park School Data

Winter Park School Districts

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Winter Park Schools

Killarney Elementary School
K-5, public
Lakemont Elementary School
K-5, public
Brookshire Elementary School
PK-5, public
Aloma Elementary School
PK-5, public
Winter Park High School
9-12, public
Eastbrook Elementary School
PK-5, public
http://www.eastbrook.scps.k12.fl.us/
Lake Howell High School
9-12, public
http://www.lakehowell.scps.k12.fl.us/
St. Margaret Mary Catholic School
PK-8, private
http://www.smmknight.org/
Trinity Preparatory School
6-12, private
http://www.trinityprep.org
Covenant Christian School
PK-8, private
http://www.covenantchristian.net
St. John Lutheran School
PK-5, private
The Geneva School
PK-12, private
http://www.genevaschool.org
The Parke House Academy
PK-6, private
Winter Park 9th Grade Center
9, public
Christian Education at Woodruff Academy
PK-12, private
http://ce-wa.org/
Threshold Childhood Development Center
1-12, private
http://www.threshold-center.org/index.html
Circle Christian School
PK-12, private
https://circlechristianschool.org/
Alpha Christian Academy
PK-8, private
http://www.alphachristianacademy.com
International Community School
PK-12, private
http://icsfla.org
Winter Park Tech
n/a, public
Conductive Education Center Of
n/a, private
Full Circle Community School
K-5, private
School for Young Performers FL
n/a, private
The Community School
PK-8, private
Orlando Tech ACE
n/a, public