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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

1004 Golfside Drive WINTER PARK, FL 32792
Photo of 1004 Golfside Drive, WINTER PARK, FL 32792 (MLS # U8068571)
4 beds 2 baths 2,476 sqft $500,000
1860 Summerland Avenue WINTER PARK, FL 32789
Photo of 1860 Summerland Avenue, WINTER PARK, FL 32789 (MLS # O5829160)
5 beds 6 baths 5,022 sqft $2,465,000
7548 Dockside Street WINTER PARK, FL 32792
Photo of 7548 Dockside Street, WINTER PARK, FL 32792 (MLS # O5827721)
3 beds 2 baths 1,434 sqft $228,800
3456 Astoria Court WINTER PARK, FL 32792
Photo of 3456 Astoria Court, WINTER PARK, FL 32792 (MLS # O5830803)
3 beds 2 baths 1,476 sqft $285,000
2257 Howard Drive WINTER PARK, FL 32789
Photo of 2257 Howard Drive, WINTER PARK, FL 32789 (MLS # O5831380)
3 beds 2 baths 1,762 sqft $359,900
150 Scottsdale Square WINTER PARK, FL 32792
Photo of 150 Scottsdale Square, WINTER PARK, FL 32792 (MLS # S5027564)
3 beds 2 baths 1,300 sqft $97,500
161 Scottsdale Square WINTER PARK, FL 32792
Photo of 161 Scottsdale Square, WINTER PARK, FL 32792 (MLS # S5027560)
1 bed 1 bath 756 sqft $75,000
3725 Bear Gully Road WINTER PARK, FL 32792
Photo of 3725 Bear Gully Road, WINTER PARK, FL 32792 (MLS # O5807429)
4 beds 3 baths 2,329 sqft $425,900
251 E Kings Way WINTER PARK, FL 32789
Photo of 251 E Kings Way, WINTER PARK, FL 32789 (MLS # O5831149)
2 beds 1 bath 1,232 sqft $475,000
2692 Galliano Circle WINTER PARK, FL 32792
Photo of 2692 Galliano Circle, WINTER PARK, FL 32792 (MLS # O5831028)
2 beds 3 baths 1,550 sqft $225,000
2920 Cove Trail WINTER PARK, FL 32789
Photo of 2920 Cove Trail, WINTER PARK, FL 32789 (MLS # O5830642)
4 beds 3 baths 2,813 sqft $650,000
2500 Lee Road, Unit 232 WINTER PARK, FL 32789
Photo of 2500 Lee Road, Unit 232, WINTER PARK, FL 32789 (MLS # O5830948)
1 bed 1 bath 645 sqft $132,000
5127 Lazy Oaks Drive WINTER PARK, FL 32792
Photo of 5127 Lazy Oaks Drive, WINTER PARK, FL 32792 (MLS # O5795954)
2 beds 3 baths 1,186 sqft $179,900
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 $95,000
1273 Michigan Avenue WINTER PARK, FL 32789
Photo of 1273 Michigan Avenue, WINTER PARK, FL 32789 (MLS # O5830783)
3 beds 3 baths 1,866 sqft $450,000

Sold Listings in Winter Park

1014 Wildmeadow Run WINTER PARK, FL 32792
Photo of 1014 Wildmeadow Run, WINTER PARK, FL 32792 (MLS # J909754)
4 beds 4 baths 2,138 sqft $436,045
2848 Bear Island Pointe WINTER PARK, FL 32792
Photo of 2848 Bear Island Pointe, WINTER PARK, FL 32792 (MLS # O5828985)
4 beds 4 baths 3,265 sqft $530,000
1781 Bryan Avenue WINTER PARK, FL 32789
Photo of 1781 Bryan Avenue, WINTER PARK, FL 32789 (MLS # O5815520)
3 beds 3 baths 2,172 sqft $525,000
2221 Shadowland Loop WINTER PARK, FL 32792
Photo of 2221 Shadowland Loop, WINTER PARK, FL 32792 (MLS # J909600)
3 beds 3 baths 2,312 sqft $330,300
151 N Orlando Avenue, Unit 125 WINTER PARK, FL 32789
Photo of 151 N Orlando Avenue, Unit 125, WINTER PARK, FL 32789 (MLS # O5828087)
2 beds 1 bath 710 sqft $155,000
1820 Pineview Circle WINTER PARK, FL 32792
Photo of 1820 Pineview Circle, WINTER PARK, FL 32792 (MLS # O5827479)
2 beds 2 baths 1,411 sqft $255,000
3303 Royal Street WINTER PARK, FL 32792
Photo of 3303 Royal Street, WINTER PARK, FL 32792 (MLS # O5825199)
2 beds 2 baths 1,050 sqft $140,000
1364 Tierra Circle WINTER PARK, FL 32792
Photo of 1364 Tierra Circle, WINTER PARK, FL 32792 (MLS # O5794030)
4 beds 2 baths 1,874 sqft $1,400
2205 Mapleton Court WINTER PARK, FL 32792
Photo of 2205 Mapleton Court, WINTER PARK, FL 32792 (MLS # O5823927)
3 beds 2 baths 1,569 sqft $279,000
1500 Gay Road, Unit 19 B WINTER PARK, FL 32789
Photo of 1500 Gay Road, Unit 19 B, WINTER PARK, FL 32789 (MLS # O5825244)
1 bed 1 bath 732 sqft $148,000
3209 Oak Lawn Place, Unit 213 WINTER PARK, FL 32792
Photo of 3209 Oak Lawn Place, Unit 213, WINTER PARK, FL 32792 (MLS # O5823560)
2 beds 3 baths 1,031 sqft $128,000
1585 Chestnut Avenue WINTER PARK, FL 32789
Photo of 1585 Chestnut Avenue, WINTER PARK, FL 32789 (MLS # O5824806)
4 beds 3 baths 2,420 sqft $572,000
MLS # O5817724 WINTER PARK, FL 32792
Photo of WINTER PARK, FL 32792 (MLS # O5817724)
2 beds 2 baths 1,067 sqft $127,400
1551 Norfolk Avenue WINTER PARK, FL 32789
Photo of 1551 Norfolk Avenue, WINTER PARK, FL 32789 (MLS # O5774655)
5 beds 3 baths 2,740 sqft $485,000
7330 Cedar Creek Court, Unit 58 WINTER PARK, FL 32792
Photo of 7330 Cedar Creek Court, Unit 58, WINTER PARK, FL 32792 (MLS # O5823224)
2 beds 3 baths 1,031 sqft $125,000

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