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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

701 Pansy Avenue WINTER PARK, FL 32789
Photo of 701 Pansy Avenue, WINTER PARK, FL 32789 (MLS # O5838147)
3 beds 4 baths 3,192 sqft $1,190,000
5352 Mellow Palm Way WINTER PARK, FL 32792
Photo of 5352 Mellow Palm Way, WINTER PARK, FL 32792 (MLS # O5837673)
5 beds 3 baths 2,572 sqft $429,900
999 Greentree Drive WINTER PARK, FL 32789
Photo of 999 Greentree Drive, WINTER PARK, FL 32789 (MLS # O5837938)
4 beds 3 baths 2,697 sqft $875,000
1817 Pineview Circle WINTER PARK, FL 32792
Photo of 1817 Pineview Circle, WINTER PARK, FL 32792 (MLS # O5837907)
3 beds 2 baths 1,564 sqft $265,000
917 Gloriosa Avenue WINTER PARK, FL 32789
Photo of 917 Gloriosa Avenue, WINTER PARK, FL 32789 (MLS # O5837900)
3 beds 2 baths 1,175 sqft $259,900
2348 Sun Valley Circle, Unit 2348 WINTER PARK, FL 32792
Photo of 2348 Sun Valley Circle, Unit 2348, WINTER PARK, FL 32792 (MLS # R4902440)
2 beds 3 baths 1,173 sqft $175,000
2450 Grand Teton Circle, Unit 2450 WINTER PARK, FL 32792
Photo of 2450 Grand Teton Circle, Unit 2450, WINTER PARK, FL 32792 (MLS # O5837384)
3 beds 2 baths 1,311 sqft $190,000
4052 Gilder Rose Place WINTER PARK, FL 32792
Photo of 4052 Gilder Rose Place, WINTER PARK, FL 32792 (MLS # O5837446)
4 beds 5 baths 4,015 sqft $809,500
3155 Crown Jewel Court WINTER PARK, FL 32792
Photo of 3155 Crown Jewel Court, WINTER PARK, FL 32792 (MLS # O5837848)
3 beds 3 baths 1,442 sqft $246,400
611 Baffie Ave WINTER PARK, FL 32789
Photo of 611 Baffie Ave, WINTER PARK, FL 32789 (MLS # G5023969)
3 beds 2 baths 1,475 sqft $279,000
531 S Ranger Boulevard, Unit 6 WINTER PARK, FL 32792
Photo of 531 S Ranger Boulevard, Unit 6, WINTER PARK, FL 32792 (MLS # O5837644)
4 beds 2 baths 1,740 sqft $380,000
1752 Meadowgold Lane WINTER PARK, FL 32792
Photo of 1752 Meadowgold Lane, WINTER PARK, FL 32792 (MLS # O5837788)
3 beds 3 baths 1,928 sqft $285,900
782 Mcintyre Avenue WINTER PARK, FL 32789
Photo of 782 Mcintyre Avenue, WINTER PARK, FL 32789 (MLS # O5835363)
3 beds 3 baths 1,901 sqft $450,000
1278 S Pennsylvania Avenue, Unit 13 WINTER PARK, FL 32789
Photo of 1278 S Pennsylvania Avenue, Unit 13, WINTER PARK, FL 32789 (MLS # O5837762)
3 beds 3 baths 1,957 sqft $689,000
608 Montego Bay Court, Unit 608 WINTER PARK, FL 32792
Photo of 608 Montego Bay Court, Unit 608, WINTER PARK, FL 32792 (MLS # O5837767)
2 beds 2 baths 1,120 sqft $148,888

Sold Listings in Winter Park

1752 Meadowgold Lane WINTER PARK, FL 32792
Photo of 1752 Meadowgold Lane, WINTER PARK, FL 32792 (MLS # J911064)
3 beds 4 baths 1,928 sqft $275,000
3232 Young Street WINTER PARK, FL 32792
Photo of 3232 Young Street, WINTER PARK, FL 32792 (MLS # S5025961)
3 beds 2 baths 2,290 sqft $330,000
2924 Antique Oaks Cir Unit 45 Circle Winter Park, FL 32792
Photo of 2924 Antique Oaks Cir Unit 45 Circle, Winter Park, FL 32792 (MLS # OM555929)
2 beds 2 baths 1,105 sqft $112,000
1247 Vardant Glade Place WINTER PARK, FL 32792
Photo of 1247 Vardant Glade Place, WINTER PARK, FL 32792 (MLS # J910950)
3 beds 2 baths 1,650 sqft $365,000
1248 Wading Water Circle WINTER PARK, FL 32792
Photo of 1248 Wading Water Circle, WINTER PARK, FL 32792 (MLS # J910825)
4 beds 3 baths 2,702 sqft $540,428
2234 Marsh Sedge Lane WINTER PARK, FL 32792
Photo of 2234 Marsh Sedge Lane, WINTER PARK, FL 32792 (MLS # J910813)
4 beds 3 baths 2,185 sqft $444,634
2040 Wood Thrush Lane WINTER PARK, FL 32792
Photo of 2040 Wood Thrush Lane, WINTER PARK, FL 32792 (MLS # J910417)
4 beds 3 baths 3,050 sqft $571,796
1656 Bomi Circle WINTER PARK, FL 32792
Photo of 1656 Bomi Circle, WINTER PARK, FL 32792 (MLS # O5822052)
4 beds 2 baths 1,840 sqft $287,500
851 Miles Avenue, Unit 2 WINTER PARK, FL 32789
Photo of 851 Miles Avenue, Unit 2, WINTER PARK, FL 32789 (MLS # O5832244)
2 beds 1 bath 808 sqft $93,000
200 Saint Andrews Boulevard, Unit 308 WINTER PARK, FL 32792
Photo of 200 Saint Andrews Boulevard, Unit 308, WINTER PARK, FL 32792 (MLS # J910162)
1 bed 1 bath 793 sqft $145,000
1376 Place Vendome WINTER PARK, FL 32789
Photo of 1376 Place Vendome, WINTER PARK, FL 32789 (MLS # O5831691)
5 beds 7 baths 4,398 sqft $1,742,539
5030 N Woodcrest Drive WINTER PARK, FL 32792
Photo of 5030 N Woodcrest Drive, WINTER PARK, FL 32792 (MLS # O5831542)
4 beds 2 baths 1,506 sqft $263,000
161 Scottsdale Square WINTER PARK, FL 32792
Photo of 161 Scottsdale Square, WINTER PARK, FL 32792 (MLS # S5027560)
1 bed 1 bath 756 sqft $73,000
7308 Swallow Run, Unit 7308 WINTER PARK, FL 32792
Photo of 7308 Swallow Run, Unit 7308, WINTER PARK, FL 32792 (MLS # O5830805)
2 beds 2 baths 784 sqft $97,000
1250 S Denning Drive, Unit 130 WINTER PARK, FL 32789
Photo of 1250 S Denning Drive, Unit 130, WINTER PARK, FL 32789 (MLS # O5829231)
2 beds 2 baths 913 sqft $135,000

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