$2,195,000
4
5Bds
5Ba
4,213sqft
Single family home for sale
Fannie Hillman & Associates
$2,195,000
4
5Bds
5Ba
4,213sqft
Single family home for sale
Fannie Hillman & Associates
$775,000
20
5Bds
4Ba
2,840sqft
Single family home for sale
Charles Rutenberg Realty Ftl via Beaches Mls
Sotera Living
$2,195,000
8
4Bds
5Ba
2,850sqft
Single family home for sale
Kelly Price & Company Llc
$479,900
2
4Bds
3Ba
2,088sqft
Single family home for sale
Houwzer Inc
Corcoran Premier Realty
$900,000
5
4Bds
3Ba
2,807sqft
Single family home for sale
Keller Williams Advantage Realty
$329,900
4
3Bds
2Ba
1,216sqft
Single family home for sale
Berkshire Hathaway Homeservices Results Realty
$675,000
3
4Bds
2Ba
1,650sqft
Single family home for sale
Keller Williams Winter Park
$650,000
8
4Bds
3Ba
2,067sqft
Single family home for sale
Keller Williams Winter Park
Premier Sotheby'S Intl. Realty
1256 S Pennsylvania Ave
$950,000 - $950,000
3 Beds
$950k+
$1,498,000
9
3Bds
4Ba
2,467sqft
Single family home for sale
Fannie Hillman & Associates
$1,599,000
12
4Bds
4Ba
2,942sqft
Single family home for sale
Keller Williams Winter Park
$1,995,000
1
4Bds
4Ba
3,314sqft
Single family home for sale
Dream Finders Realty Group Corp
$780,000
5
5Bds
3Ba
2,194sqft
Single family home for sale
Serhant
Bhhs Florida Realty
Watson Realty Corp
$575,000
4
4Bds
2Ba
1,936sqft
Single family home for sale
Keller Williams Winter Park
$1,890,000
3
4Bds
4Ba
3,307sqft
Single family home for sale
Jw Gaston Llc
$660,000
10
3Bds
3Ba
1,690sqft
Townhouse for sale
Keller Williams Realty At The Parks
$675,000
5
4Bds
3Ba
2,366sqft
Single family home for sale
Re/Max Town & Country Realty
$2,190,000
18
4Bds
3Ba
3,463sqft
Single family home for sale
Denovo Realty
$3,075,000
4
5Bds
6Ba
3,863sqft
Single family home for sale
Premier Sotheby'S Intl. Realty
Central Florida Real Estate
$395,000
5
3Bds
2Ba
1,310sqft
Single family home for sale
Charles Rutenberg Realty Orlando
$485,000
7
4Bds
2Ba
2,092sqft
Single family home for sale
Preferred Real Estate Brokers
$599,000
6
4Bds
3Ba
2,102sqft
Single family home for sale
Lpt Realty, Llc
$700,000
7
4Bds
3Ba
2,016sqft
Sale Pending
Charles Rutenberg Realty Orlando
$1,875,000
4
4Bds
4Ba
3,440sqft
Single family home for sale
Premier Sotheby'S Intl. Realty
$1,550,000
7
6Bds
5Ba
5,239sqft
Mansion for sale
Re/Max Town & Country Realty
$440,000
17
4Bds
2Ba
2,189sqft
Single family home for sale
Lokation
$669,000
5
4Bds
2Ba
1,605sqft
Single family home for sale
Networth Realty Of Orlando, Llc
$999,000
5
4Bds
3Ba
2,803sqft
Single family home for sale
Fannie Hillman & Associates
$1,649,000
3Bds
3Ba
2,857sqft
Single family home for sale
Premier Sotheby'S Intl. Realty
$675,000
11
4Bds
2Ba
1,509sqft
Single family home for sale
Keller Williams Winter Park
Coldwell Banker Realty
$334,000
3
3Bds
2Ba
1,149sqft
Single family home for sale
Shorestone Property Group
$1,690,000
6
4Bds
4Ba
3,174sqft
Single family home for sale
Premier Sotheby'S Intl. Realty
$915,000
7
3Bds
4Ba
2,093sqft
Townhouse for sale
Iad Real Estate
$410,000
4
3Bds
2Ba
1,494sqft
Single family home for sale
Real Property Management And Realty
$1,049,900
9
5Bds
5Ba
3,652sqft
Single family home for sale
Re/Max 200 Realty
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Winter Park is a balanced market, giving buyers and sellers room to negotiate. With 4.3 months of supply and homes averaging 82 days on the market, you can make decisions without the pressure of a highly competitive market.
Balanced Market
82
191
In Sep 2026 · YoY
Current rate · YoY
30-Year Fixed
30-yr fixed rate 6.23% · Data as of Sep 2026 · Source: Houzeo Research.
View Full Winter Park Market Report76
Homes Available
$ 960,375
Median List Price
82 Days
Avg on Market
Do Real Estate on the Go!