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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

5108 Oak Hill Drive WINTER PARK, FL 32792
Photo of 5108 Oak Hill Drive, WINTER PARK, FL 32792 (MLS # O5765817)
2 beds 2 baths 1,020 sqft $199,000
2926 Montfichet Lane WINTER PARK, FL 32792
Photo of 2926 Montfichet Lane, WINTER PARK, FL 32792 (MLS # O5763555)
4 beds 2 baths 1,674 sqft $389,900
690 Osceola Avenue, Unit 209 WINTER PARK, FL 32789
Photo of 690 Osceola Avenue, Unit 209, WINTER PARK, FL 32789 (MLS # O5765521)
2 beds 2 baths 1,148 sqft $380,000
2010 W Fawsett Road WINTER PARK, FL 32789
Photo of 2010 W Fawsett Road, WINTER PARK, FL 32789 (MLS # O5764673)
5 beds 6 baths 6,786 sqft $3,150,000
1641 Via Tuscany WINTER PARK, FL 32789
Photo of 1641 Via Tuscany, WINTER PARK, FL 32789 (MLS # O5765753)
5 beds 5 baths 4,655 sqft $1,386,000
830 W Canton Avenue WINTER PARK, FL 32789
Photo of 830 W Canton Avenue, WINTER PARK, FL 32789 (MLS # O5765659)
3 beds 3 baths 1,965 sqft $685,000
345 Gilbert Road, Unit 4 WINTER PARK, FL 32792
Photo of 345 Gilbert Road, Unit 4, WINTER PARK, FL 32792 (MLS # O5760492)
3 beds 2 baths 1,692 sqft $329,000
367 Fitzhugh Road WINTER PARK, FL 32792
Photo of 367 Fitzhugh Road, WINTER PARK, FL 32792 (MLS # O5765627)
4 beds 2 baths 1,906 sqft $535,000
2529 Modac Trail WINTER PARK, FL 32789
Photo of 2529 Modac Trail, WINTER PARK, FL 32789 (MLS # O5765544)
4 beds 3 baths 3,043 sqft $515,000
910 Hedgewood Court WINTER PARK, FL 32792
Photo of 910 Hedgewood Court, WINTER PARK, FL 32792 (MLS # O5764821)
3 beds 3 baths 1,578 sqft $259,000
121 W Kings Way WINTER PARK, FL 32789
Photo of 121 W Kings Way, WINTER PARK, FL 32789 (MLS # O5765306)
5 beds 7 baths 5,504 sqft $2,375,000
3651 N Goldenrod Road, Unit 101 WINTER PARK, FL 32792
Photo of 3651 N Goldenrod Road, Unit 101, WINTER PARK, FL 32792 (MLS # O5765414)
2 beds 2 baths 940 sqft $99,000
1814 Walker Avenue WINTER PARK, FL 32789
Photo of 1814 Walker Avenue, WINTER PARK, FL 32789 (MLS # O5764851)
3 beds 3 baths 1,810 sqft $425,000
2892 Carew Avenue WINTER PARK, FL 32789
Photo of 2892 Carew Avenue, WINTER PARK, FL 32789 (MLS # O5765516)
4 beds 2 baths 1,708 sqft $289,900
301 Clay Street WINTER PARK, FL 32789
Photo of 301 Clay Street, WINTER PARK, FL 32789 (MLS # O5765386)
3 beds 3 baths 1,959 sqft $675,000

Sold Listings in Winter Park

2704 Parkland Drive WINTER PARK, FL 32789
Photo of 2704 Parkland Drive, WINTER PARK, FL 32789 (MLS # J902165)
4 beds 4 baths 3,296 sqft $904,000
1810 Mondrian Circle, Unit 25 WINTER PARK, FL 32789
Photo of 1810 Mondrian Circle, Unit 25, WINTER PARK, FL 32789 (MLS # O5484559)
3 beds 4 baths 2,276 sqft $522,405
2536 Brookshire Avenue WINTER PARK, FL 32792
Photo of 2536 Brookshire Avenue, WINTER PARK, FL 32792 (MLS # O5763922)
4 beds 4 baths 3,140 sqft $784,900
1628 Elizabeths Walk WINTER PARK, FL 32789
Photo of 1628 Elizabeths Walk, WINTER PARK, FL 32789 (MLS # O5570219)
4 beds 3 baths 3,699 sqft $835,000
200 Saint Andrews Boulevard, Unit 1606 WINTER PARK, FL 32792
Photo of 200 Saint Andrews Boulevard, Unit 1606, WINTER PARK, FL 32792 (MLS # J901684)
2 beds 2 baths 983 sqft $92,500
1880 Taylor Avenue WINTER PARK, FL 32789
Photo of 1880 Taylor Avenue, WINTER PARK, FL 32789 (MLS # O5757918)
4 beds 2 baths 1,652 sqft $490,000
700 Melrose Avenue, Unit K-33 WINTER PARK, FL 32789
Photo of 700 Melrose Avenue, Unit K-33, WINTER PARK, FL 32789 (MLS # O5756858)
2 beds 2 baths 1,074 sqft $220,000
7039 Citrus Point Court WINTER PARK, FL 32792
Photo of 7039 Citrus Point Court, WINTER PARK, FL 32792 (MLS # O5755118)
3 beds 2 baths 1,420 sqft $230,000
2401 Antilles Drive WINTER PARK, FL 32792
Photo of 2401 Antilles Drive, WINTER PARK, FL 32792 (MLS # O5757638)
3 beds 2 baths 1,719 sqft $199,000
1665 Spruce Avenue WINTER PARK, FL 32789
Photo of 1665 Spruce Avenue, WINTER PARK, FL 32789 (MLS # O5757272)
4 beds 5 baths 4,463 sqft $1,400,000
3051 Autumn Court WINTER PARK, FL 32792
Photo of 3051 Autumn Court, WINTER PARK, FL 32792 (MLS # O5756689)
3 beds 2 baths 1,266 sqft $175,000
6812 Bonavista Court WINTER PARK, FL 32792
Photo of 6812 Bonavista Court, WINTER PARK, FL 32792 (MLS # O5756168)
2 beds 2 baths 1,123 sqft $165,000
2936 Antique Oaks Circle, Unit 67 WINTER PARK, FL 32792
Photo of 2936 Antique Oaks Circle, Unit 67, WINTER PARK, FL 32792 (MLS # R4901355)
2 beds 2 baths 1,018 sqft $115,000
585 Carnation Drive WINTER PARK, FL 32792
Photo of 585 Carnation Drive, WINTER PARK, FL 32792 (MLS # O5756366)
3 beds 2 baths 1,377 sqft $240,000
3028 Dikewood Court WINTER PARK, FL 32792
Photo of 3028 Dikewood Court, WINTER PARK, FL 32792 (MLS # O5755937)
3 beds 2 baths 1,606 sqft $255,000

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