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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

281 Scottsdale Square, Unit 281 WINTER PARK, FL 32792
Photo of 281 Scottsdale Square, Unit 281, WINTER PARK, FL 32792 (MLS # O5855666)
1 bed 1 bath 756 sqft $66,900
1751 Goodrich Avenue WINTER PARK, FL 32789
Photo of 1751 Goodrich Avenue, WINTER PARK, FL 32789 (MLS # O5855551)
4 beds 4 baths 2,170 sqft $859,900
200 Saint Andrews Blvd, Unit 1803 WINTER PARK, FL 32792
Photo of 200 Saint Andrews Blvd, Unit 1803, WINTER PARK, FL 32792 (MLS # O5855207)
2 beds 2 baths 1,219 sqft $172,900
2216 Fairglenn Way WINTER PARK, FL 32792
Photo of 2216 Fairglenn Way, WINTER PARK, FL 32792 (MLS # O5855139)
4 beds 2 baths 2,052 sqft $379,900
2251 Coventry Drive WINTER PARK, FL 32792
Photo of 2251 Coventry Drive, WINTER PARK, FL 32792 (MLS # O5855169)
5 beds 3 baths 1,864 sqft $349,000
340 Alberta Drive WINTER PARK, FL 32789
Photo of 340 Alberta Drive, WINTER PARK, FL 32789 (MLS # O5849402)
4 beds 4 baths 3,226 sqft $899,000
1816 Maywood Road WINTER PARK, FL 32792
Photo of 1816 Maywood Road, WINTER PARK, FL 32792 (MLS # O5855286)
3 beds 2 baths 1,464 sqft $295,000
2685 Bongart Road WINTER PARK, FL 32792
Photo of 2685 Bongart Road, WINTER PARK, FL 32792 (MLS # S5032190)
3 beds 2 baths 1,198 sqft $314,995
2779 Prince John Road, Unit 1 WINTER PARK, FL 32792
Photo of 2779 Prince John Road, Unit 1, WINTER PARK, FL 32792 (MLS # O5855399)
3 beds 2 baths 1,579 sqft $384,900
1919 Stonehurst Road WINTER PARK, FL 32789
Photo of 1919 Stonehurst Road, WINTER PARK, FL 32789 (MLS # O5854976)
5 beds 5 baths 5,605 sqft $2,000,000
251 Glenridge Way WINTER PARK, FL 32789
Photo of 251 Glenridge Way, WINTER PARK, FL 32789 (MLS # O5855171)
3 beds 3 baths 1,314 sqft $425,000
436 Darcey Drive WINTER PARK, FL 32792
Photo of 436 Darcey Drive, WINTER PARK, FL 32792 (MLS # O5854670)
3 beds 2 baths 1,592 sqft $389,000
1210 Oaks Blvd WINTER PARK, FL 32789
Photo of 1210 Oaks Blvd, WINTER PARK, FL 32789 (MLS # O5855100)
3 beds 4 baths 2,680 sqft $1,225,000
530 N Lakemont Avenue WINTER PARK, FL 32792
Photo of 530 N Lakemont Avenue, WINTER PARK, FL 32792 (MLS # O5855190)
3 beds 2 baths 1,572 sqft $368,000
2443 Forfarshire Drive WINTER PARK, FL 32792
Photo of 2443 Forfarshire Drive, WINTER PARK, FL 32792 (MLS # O5855223)
3 beds 2 baths 1,593 sqft $399,000

Sold Listings in Winter Park

625 Blairshire Circle, Unit 3 WINTER PARK, FL 32792
4 beds 4 baths 1,835 sqft $498,000
3644 Bougainvillea Court WINTER PARK, FL 32792
Photo of 3644 Bougainvillea Court, WINTER PARK, FL 32792 (MLS # J912847)
3 beds 2 baths 1,161 sqft $125,000
2233 Brookshire Avenue WINTER PARK, FL 32792
Photo of 2233 Brookshire Avenue, WINTER PARK, FL 32792 (MLS # O5847802)
3 beds 2 baths 1,069 sqft $302,821
4308 Enright Court WINTER PARK, FL 32792
Photo of 4308 Enright Court, WINTER PARK, FL 32792 (MLS # S5030030)
4 beds 2 baths 2,265 sqft $335,000
2301 Mulbry Drive WINTER PARK, FL 32789
Photo of 2301 Mulbry Drive, WINTER PARK, FL 32789 (MLS # T3179517)
4 beds 5 baths 3,150 sqft $900,000
151 N Orlando Avenue, Unit 101 WINTER PARK, FL 32789
Photo of 151 N Orlando Avenue, Unit 101, WINTER PARK, FL 32789 (MLS # J912760)
2 beds 1 bath 804 sqft $107,500
1276 S Pennsylvania Avenue, Unit 12 WINTER PARK, FL 32789
Photo of 1276 S Pennsylvania Avenue, Unit 12, WINTER PARK, FL 32789 (MLS # O5785228)
3 beds 3 baths 1,957 sqft $670,000
603 Warrenton Road WINTER PARK, FL 32792
Photo of 603 Warrenton Road, WINTER PARK, FL 32792 (MLS # J912682)
2 beds 2 baths 1,233 sqft $188,500
1905 Sycamore Drive WINTER PARK, FL 32789
Photo of 1905 Sycamore Drive, WINTER PARK, FL 32789 (MLS # J912521)
3 beds 1 bath 1,506 sqft $314,000
2325 Eastbrook Boulevard WINTER PARK, FL 32792
Photo of 2325 Eastbrook Boulevard, WINTER PARK, FL 32792 (MLS # O5850558)
3 beds 2 baths 1,273 sqft $250,000
4317 Enright Court WINTER PARK, FL 32792
Photo of 4317 Enright Court, WINTER PARK, FL 32792 (MLS # G5019344)
4 beds 2 baths 1,838 sqft $254,900
7331 Cook Lane WINTER PARK, FL 32792
Photo of 7331 Cook Lane, WINTER PARK, FL 32792 (MLS # O5849682)
4 beds 2 baths 1,380 sqft $273,200
MLS # O5840474 WINTER PARK, FL 32792
Photo of WINTER PARK, FL 32792 (MLS # O5840474)
4 beds 3 baths 2,340 sqft $304,000
1709 Pine Avenue WINTER PARK, FL 32789
Photo of 1709 Pine Avenue, WINTER PARK, FL 32789 (MLS # O5848561)
2 beds 2 baths 1,377 sqft $425,000
2211 Marsh Sedge Lane WINTER PARK, FL 32792
Photo of 2211 Marsh Sedge Lane, WINTER PARK, FL 32792 (MLS # J912260)
5 beds 4 baths 3,532 sqft $485,670

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