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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

2406 Timberline Drive WINTER PARK, FL 32792
Photo of 2406 Timberline Drive, WINTER PARK, FL 32792 (MLS # O5779256)
2 beds 2 baths 1,316 sqft $174,900
368 Sylvan Drive WINTER PARK, FL 32789
Photo of 368 Sylvan Drive, WINTER PARK, FL 32789 (MLS # O5779697)
3 beds 2 baths 1,612 sqft $474,900
2381 Roxbury Road WINTER PARK, FL 32789
Photo of 2381 Roxbury Road, WINTER PARK, FL 32789 (MLS # O5779567)
3 beds 2 baths 1,959 sqft $350,000
445 Garfield Avenue WINTER PARK, FL 32789
Photo of 445 Garfield Avenue, WINTER PARK, FL 32789 (MLS # O5778739)
3 beds 2 baths 1,447 sqft $375,000
1420 Place Picardy WINTER PARK, FL 32789
Photo of 1420 Place Picardy, WINTER PARK, FL 32789 (MLS # O5779720)
4 beds 5 baths 4,658 sqft $1,795,000
2664 Barbados Drive WINTER PARK, FL 32792
Photo of 2664 Barbados Drive, WINTER PARK, FL 32792 (MLS # O5779440)
3 beds 2 baths 1,284 sqft $177,500
1330 Lyndale Boulevard WINTER PARK, FL 32789
Photo of 1330 Lyndale Boulevard, WINTER PARK, FL 32789 (MLS # O5779700)
2 beds 2 baths 1,422 sqft $440,000
616 Ellendale Drive WINTER PARK, FL 32792
Photo of 616 Ellendale Drive, WINTER PARK, FL 32792 (MLS # G5014926)
3 beds 2 baths 1,405 sqft $200,000
7767 Country Place, Unit I-5 WINTER PARK, FL 32792
Photo of 7767 Country Place, Unit I-5, WINTER PARK, FL 32792 (MLS # O5779614)
2 beds 2 baths 1,068 sqft $140,000
1458 Hyde Park Drive WINTER PARK, FL 32792
Photo of 1458 Hyde Park Drive, WINTER PARK, FL 32792 (MLS # O5767238)
3 beds 2 baths 1,673 sqft $269,000
2001 Loch Berry Road WINTER PARK, FL 32792
Photo of 2001 Loch Berry Road, WINTER PARK, FL 32792 (MLS # O5779188)
3 beds 2 baths 1,638 sqft $420,000
1600 Alabama Dr, Unit 202 WINTER PARK, FL 32789
Photo of 1600 Alabama Dr, Unit 202, WINTER PARK, FL 32789 (MLS # G5014978)
2 beds 2 baths 1,999 sqft $990,000
730 Via Lombardy WINTER PARK, FL 32789
Photo of 730 Via Lombardy, WINTER PARK, FL 32789 (MLS # O5779426)
3 beds 3 baths 2,666 sqft $1,200,000
2572 Passamonte Drive, Unit 903 WINTER PARK, FL 32792
Photo of 2572 Passamonte Drive, Unit 903, WINTER PARK, FL 32792 (MLS # O5779353)
3 beds 3 baths 1,554 sqft $225,000
1211 Verdant Glade WINTER PARK, FL 32792
Photo of 1211 Verdant Glade, WINTER PARK, FL 32792 (MLS # O5779319)
4 beds 4 baths 2,138 sqft $448,100

Sold Listings in Winter Park

7164 Swallow Run, Unit #2 WINTER PARK, FL 32792
Photo of 7164 Swallow Run, Unit #2, WINTER PARK, FL 32792 (MLS # O5779111)
3 beds 3 baths 1,565 sqft $210,000
7421 Daniel Webster Drive, Unit A WINTER PARK, FL 32792
Photo of 7421 Daniel Webster Drive, Unit A, WINTER PARK, FL 32792 (MLS # O5767966)
1 bed 1 bath 809 sqft $69,000
221 Lewfield Circle, Unit 221 WINTER PARK, FL 32792
Photo of 221 Lewfield Circle, Unit 221, WINTER PARK, FL 32792 (MLS # J903332)
2 beds 2 baths 953 sqft $120,000
MLS # O5771105 WINTER PARK, FL 32789
Photo of WINTER PARK, FL 32789 (MLS # O5771105)
3 beds 3 baths 1,655 sqft $325,000
1761 Pinetree Road WINTER PARK, FL 32789
Photo of 1761 Pinetree Road, WINTER PARK, FL 32789 (MLS # O5774365)
5 beds 6 baths 4,792 sqft $3,300,000
1146 Washington Avenue, Unit 19 WINTER PARK, FL 32789
Photo of 1146 Washington Avenue, Unit 19, WINTER PARK, FL 32789 (MLS # O5759058)
3 beds 3 baths 2,083 sqft $2,200
614 Selkirk Drive WINTER PARK, FL 32792
Photo of 614 Selkirk Drive, WINTER PARK, FL 32792 (MLS # O5773343)
3 beds 2 baths 1,792 sqft $351,000
730 Pinetree Road WINTER PARK, FL 32789
Photo of 730 Pinetree Road, WINTER PARK, FL 32789 (MLS # O5773168)
4 beds 4 baths 3,724 sqft $1,170,000
100 S Virginia Avenue, Unit 202 WINTER PARK, FL 32789
Photo of 100 S Virginia Avenue, Unit 202, WINTER PARK, FL 32789 (MLS # O5773124)
3 beds 3 baths 2,983 sqft $849,000
1832 Whitehall Drive WINTER PARK, FL 32789
Photo of 1832 Whitehall Drive, WINTER PARK, FL 32789 (MLS # O5772685)
4 beds 3 baths 3,050 sqft $599,000
3630 Mango Court WINTER PARK, FL 32792
Photo of 3630 Mango Court, WINTER PARK, FL 32792 (MLS # O5762104)
3 beds 2 baths 1,356 sqft $235,000
731 Via Lombardy WINTER PARK, FL 32789
Photo of 731 Via Lombardy, WINTER PARK, FL 32789 (MLS # O5771112)
5 beds 4 baths 3,707 sqft $1,146,000
1913 Houndslake Drive WINTER PARK, FL 32792
Photo of 1913 Houndslake Drive, WINTER PARK, FL 32792 (MLS # O5754093)
3 beds 3 baths 1,880 sqft $209,548
3078 Riverbrook Drive WINTER PARK, FL 32792
Photo of 3078 Riverbrook Drive, WINTER PARK, FL 32792 (MLS # O5769483)
3 beds 2 baths 1,482 sqft $214,500
866 Via Lugano WINTER PARK, FL 32789
Photo of 866 Via Lugano, WINTER PARK, FL 32789 (MLS # O5750241)
6 beds 10 baths 10,613 sqft $7,250,000

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