Winter Park FL Homes & Real Estate

Included below are homes for sale and real estate in Winter Park, FL.

If you would like more information on any of these Winter Park real estate listings, just click on a property to access the full details. From there, you can request more information or schedule a tour. And we'd be happy to provide you with disclosures, past sales history, dates and prices of properties which have recently sold nearby, and more, so just let us know how we can help!

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Winter Park December 1, 2021
80
Listed
72
Avg. DOM
$385.69
Avg. $ / Sq.Ft.
$785,000
Med. List Price
80 Properties
Page 1 of 7
$1,450,000
Subdivision: Roundelay
5
Beds
4
Baths
4,720
Sq.Ft.
1910
Year Built
2
Days on Site
O5988710
MLS
The historic Harris Grove House was built in approximately 1910 as the main home for the orange grove with views of Lake Sylvan and is one of Winter Park's finest gems. This home features extensive...
$775,000
Subdivision: Cherokee Park
5
Beds
4
Baths
2,592
Sq.Ft.
1990
Year Built
2
Days on Site
O5987236
MLS
Don't miss this amazing opportunity to own a duplex in the heart of Winter Park. Located just a short stroll from Rollins College, Azalea Park and Park Avenue shopping and restaurants. There are two...
$1,300,000
Subdivision: Hamilton Place
4
Beds
4F11/2
Baths
2,732
Sq.Ft.
2009
Year Built
3
Days on Site
O5988265
MLS
Custom Mediterranean home steps from Park Avenue, Winter Park Village and Winter Park Country Club Golf Course. This home was Built in 2009 and renovated with modern inspired interior decor in 2015....
$399,000
Subdivision: Citrus Point
3
Beds
2
Baths
1,495
Sq.Ft.
1985
Year Built
6
Days on Site
O5988129
MLS
Lovely 3 bedroom, 2 bathroom home with a 2-car garage . You'll enjoy this freshly painted, fenced home with its massive backyard while relaxing on the inviting enclosed porch in a quiet neighborhood....
$749,900
Subdivision: Kenilworth Shores Sec 05
4
Beds
3
Baths
2,125
Sq.Ft.
1963
Year Built
8
Days on Site
O5987737
MLS
WINTER PARK CUSTOM HOME COMPLETELY RENOVATED! A rare opportunity! This home has so many wonderful features and shows like new, from the moment you walk in the door you will be impressed! The interior...
$2,100,000
Subdivision: Kenilworth Shores Sec 01
5
Beds
5F11/2
Baths
4,214
Sq.Ft.
2022
Year Built
8
Days on Site
O5987208
MLS
Pre-Construction. To be built. Here is the perfect opportunity to purchase your very own private sanctuary in the heart of Winter Park. This exquisite transitional modern home by Parade of Homes...
$375,000
Subdivision: Arrowhead Cove
3
Beds
2
Baths
2,251
Sq.Ft.
1972
Year Built
8
Days on Site
S5059033
MLS
Cheerful and Updated Pool Home in Winter Park! Beautifully nestled on an oversized 10,257sqft lot in the highly sought-after community of Arrowhead Cove, this 3BR/2BA, 2,251sqft residence stuns with...
$1,695,000
Subdivision: Morseland Sub
3
Beds
2F11/2
Baths
2,774
Sq.Ft.
1984
Year Built
8
Days on Site
O5986766
MLS
BETTER THAN NEW, FULLY RENOVATED HOME IN THE SOUGHT-AFTER WINTER PARK WALKING DISTANCE TO PARK AVENUE! This exquisitely updated 3-bedroom, 2/1-bathroom provincial masterpiece sits on an oversized...
$368,900
Subdivision: Bel Aire Pines
4
Beds
2
Baths
1,615
Sq.Ft.
1983
Year Built
10
Days on Site
O5987559
MLS
Come and see this charming 4 bedroom, 2 bathroom home in Winter Park! As you enter, the open-concept living room glows with warm natural light, inviting you to sit and relax. The spacious dine-in...
$1,695,000
Subdivision: Winter Park Heights
4
Beds
4
Baths
3,075
Sq.Ft.
2008
Year Built
10
Days on Site
O5987577
MLS
Award Winning LEED Certified Gold MODERN home in the heart of Winter Park. Built in 2008 by E2 Homes. As you enter you will enjoy the view of open floor plan surrounded by large windows and Sliding...
$799,000
Subdivision: Dubsdread Heights
4
Beds
3F11/2
Baths
3,040
Sq.Ft.
2010
Year Built
12
Days on Site
O5987307
MLS
Builder's own, custom home located in the heart of it all! Stunning 4 bedroom, 3.5 bath offering 3,040 sq.ft. of custom-built living. Well thought out floor plan with downstairs master, living,...
$459,900
Subdivision: Garden Acres
3
Beds
2F11/2
Baths
1,389
Sq.Ft.
1946
Year Built
13
Days on Site
O5987121
MLS
Cozy, expertly updated, situated on a quiet and quaint street steps away from the infamous Park Avenue and North Orange Avenue shopping and design districts, a beautiful and affordable home in...