Winter Park Real Estate

Some of the best housing options in Seminole County are in the Winter Park Real Estate market, with a variety of single family homes for sale priced between $206,000 and as high as $2,849,000 one to five bedroom homes that range in size from 884 to 7,874 square feet. Options for Condos in Winter Park range from $152,000 for an apartment with one bedroom and one bathroom to three bedrooms and two bathroom luxury condominiums that sell for up to $310,000. Suppose a Townhome for sale in Winter Park is what you are looking for, a two-bedroom, one bathroom 990 square foot villa or a three-bed, three-bath home as large as 2,811 sq ft ranging in price from $250,000 to $469,000.

We have detailed information regarding 53 communities in Winter Park, including 27 non-gated communities of single family homes, fourteen condo buildings, and nine gated communities including some new construction opportunities and open houses. Winter Park real estate activity on the MLS indicates 480 properties are currently on the market (as of October 11th, 2025). Whether relocating to Winter Park from another state or upsizing or downsizing, whichever of the many homes for sale in Winter Park and the entire Central Florida region you choose, our professional Realtors in Winter Park Florida can guide you through the home-buying process.

Winter Park Homes For Sale

$12.5 Million

MLS#AX-11776219

570 Manor Rd, Maitland
Winter Park, FL 32751

6

10

6

10,172 SqFt

Water Front

177 Days

$8.95 Million

Windsong

1120 Preserve Point Dr
Winter Park, FL 32789

7

11

4

13,377 SqFt

Pool

Water Front

1.63 Acres

5 Days

$8.5 Million

Windsong

1112 Preserve Point Dr
Winter Park, FL 32789

5

6

3

9,159 SqFt

Pool

Water Front

1.94 Acres

136 Days

Reduced

$6,600,000

$10,999,999

MLS#MFRO6260493

2661 Via Tuscany
Winter Park, FL 32789

4

5

2

5,231 SqFt

Pool

0.36 Acres

319 Days

New Construction

$6.5 Million

MLS#MFRO6331715

887 Georgia Ave
Winter Park, FL 32789

6

6

2

6,758 SqFt

Pool

1.07 Acres

72 Days

Under Contract

$5,999,000

MLS#MFRO6342506

1240 Harding Street
Winter Park, FL 32789

5

6

2

8,220 SqFt

Pool

0.55 Acres

32 Days

$5.95 Million

MLS#MFRO6332790

1181 Via Capri
Winter Park, FL 32789

5

6

3

5,617 SqFt

Pool

0.3 Acres

67 Days

New Construction

Reduced

$5,895,000

$6,950,000

MLS#MFRO6285791

1400 Alabama Dr
Winter Park, FL 32789

5

9

4

10,175 SqFt

Pool

Water Front

0.7 Acres

225 Days

$5,549,000

MLS#MFRO6318156

698 N New York Ave
Winter Park, FL 32789

5

6

2

6,382 SqFt

Pool

0.16 Acres

71 Days

New Construction

Reduced

$5,495,000

$6,180,000

MLS#AX-11824988

2211 Azalea Pl
Winter Park, FL 32789

5

7

5

9,111 SqFt

Water Front

0.686 Acres

107 Days

Reduced

$5,495,000

$6,180,000

MLS#MFRO6319674

2211 Azalea Pl
Winter Park, FL 32789

5

7

5

9,166 SqFt

Pool

Water Front

0.69 Acres

110 Days

Reduced

$5,450,000

$5,800,000

MLS#MFRO6321906

1221 Richmond Rd
Winter Park, FL 32789

5

6

2

6,524 SqFt

Pool

0.34 Acres

92 Days

480 Active Listings in Winter Park, FL

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Living in Winter Park affords you easy access to nearby golf courses, fine dining, entertainment venues and various other amenities and conveniences in the city of Winter Park. The I-4 or Florida's Turnpike provide an easy transition to nearby cities such as Casselberry, Maitland, Winter Springs, Altamonte Springs, Sanford, Longwood, Lake Mary, Deland, Apopka, Labelle, and Oviedo.

Boating and watersports are integral to the Central Florida lifestyle, offering year-round access to an abundance of lakes, vibrant marine life, and a culture centered around outdoor leisure and recreation. Winter Park real estate prices are directly correlated to it's proximity to these amenities.

Additionally, four local airports are easily accessible - Orlando Executive (ORL), Orlando International (MCO), Orlando Sanford International (SFB), and Kissimmee Gateway (ISM) in Orlando.

The data relating to homes for sale or lease or other real estate for sale or for rent on the ZFC website comes in part from a cooperative data exchange program of the MLS in which this Broker participates. The real estate displayed may not be all of the homes in the database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Homes for sale that are listed by Brokers other than this Broker are marked with either the listing Broker's name or the MLS name or a logo provided by the MLS and the details page about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. ZFC, the Florida Association of Realtors and its cooperating Multiple Listing Services do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law including the fair housing act prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing. All properties featuring the Miami Realtors logo are provided by the Miami Association of Realtors. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.