Florida

Homes for Sale in Winter Park

“163 active listings in Winter Park, Florida · Median list price $575,000”

163 listings

Avg $969,766

97 days avg

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Market Overview

Winter Park Real Estate at a Glance

Current market statistics for Winter Park, FL

163

Active Listings

$970K

Avg Price

$575K

Median Price

2,128

Avg Sqft

Avg Days

Price Range

From

$107,000

$6,900,000

Listing selection

Homes to Explore

Active listings from the winter park collection

$1.6M

1257 WADING WATERS Circle

Winter Park, FL

$860K

120 LONGBRANCH Road

Winter Park, FL

$475K

2008 Houndslake Drive

Winter Park, FL

$189K

2918 ANTIQUE OAKS Circle

$2.5M

450 LAKEWOOD Drive

More listings

Homes for Sale in Winter Park

Every active listing in Winter Park, browsable page by page.

Condo

$359K

1306 S PENNSYLVANIA Avenue

Winter Park, FL

2 bd1 ba830

Single Family

$440K

1818 DOVER Road

Winter Park, FL

3 bd2 ba1,873

Single Family

$1.1M

1517 HARMON Avenue

Winter Park, FL

4 bd4 ba2,135

Condo

$249K

2463 GRAND TETON Circle

Winter Park, FL

3 bd3 ba1,720

Single Family

$750K

1421 CHESTNUT Avenue

Winter Park, FL

3 bd1 ba1,325

Land

$750K

1421 CHESTNUT Avenue

Winter Park, FL

0 bd0 ba

Single Family

$675K

2215 WOODCREST Drive

Winter Park, FL

4 bd2 ba1,688

Single Family

$5.5M

1166 PALMER Avenue

Winter Park, FL

5 bd7 ba5,181

Condo

$389K

720 KILLARNEY BAY Court

Winter Park, FL

2 bd2 ba1,140

Single Family

$427K

1386 CLEMATIS Lane

Winter Park, FL

4 bd3 ba1,714

Condo

$150K

7453 DANIEL WEBSTER Drive

Winter Park, FL

2 bd2 ba1,063

Single Family

$2.2M

1271 PALMER Avenue

Winter Park, FL

4 bd5 ba2,850

Single Family

$2.2M

1803 Barker Drive

Winter Park, FL

4 bd3 ba3,463

Single Family

$300K

3484 SEAGRAPE Drive

Winter Park, FL

4 bd2 ba1,227

Land

$450K

786 W CANTON Avenue

Winter Park, FL

0 bd0 ba

Single Family

$300K

5080 SEMINOLE Avenue

Winter Park, FL

3 bd2 ba1,078

Townhouse

$1.3M

504 W SWOOPE Avenue

Winter Park, FL

3 bd3 ba2,563

Single Family

$450K

2301 CONIFER Avenue

Winter Park, FL

4 bd2 ba2,189

Condo

$235K

2383 SUN VALLEY Circle

Winter Park, FL

2 bd2 ba1,295

Land

$960K

447 N PHELPS Avenue

Winter Park, FL

0 bd0 ba

Single Family

$4.3M

250 W READING Way

Winter Park, FL

5 bd5 ba4,853

Single Family

$960K

447 N PHELPS Avenue

Winter Park, FL

2 bd1 ba1,290

Townhouse

$295K

2302 BARBADOS Drive

Winter Park, FL

2 bd2 ba1,544

Single Family

$1.6M

1257 WADING WATERS Circle

Winter Park, FL

6 bd5 ba5,239

Commercial

$1.4M

436 N WYMORE Road

Winter Park, FL

0 bd0 ba3,021

Condo

$165K

3651 N GOLDENROD Road

Winter Park, FL

2 bd2 ba840

Condo

$2.4M

200 S INTERLACHEN Avenue

Winter Park, FL

3 bd4 ba3,110

Land

$825K

1431 PALM Avenue

Winter Park, FL

0 bd0 ba

Townhouse

$425K

2349 SHADOWLAND Loop

Winter Park, FL

3 bd3 ba1,755

Condo

$130K

2500 LEE Road

Winter Park, FL

1 bd1 ba645

Single Family

$740K

4039 COOL WATER Court

Winter Park, FL

4 bd2 ba2,267

Condo

$135K

3020 ANTIQUE OAKS Circle

Winter Park, FL

2 bd2 ba1,018

Commercial

$1M

7839 UNIVERSITY GARDEN Drive

Winter Park, FL

0 bd0 ba

Condo

$269K

5108 LAZY OAKS Drive

Winter Park, FL

2 bd2 ba1,008

Single Family

$850K

2345 BROOKSHIRE Avenue

Winter Park, FL

3 bd3 ba2,488

Single Family

$495K

3020 NICHOLSON Drive

Winter Park, FL

4 bd2 ba1,756

Single Family

$975K

471 HOLT Avenue

Winter Park, FL

4 bd3 ba2,528

Single Family

$1.6M

2430 CHANTILLY Avenue

Winter Park, FL

4 bd4 ba2,916

Multi-Family

$275K

3302 ROYAL Street

Winter Park, FL

3 bd2 ba1,197

Condo

$350K

500 N PENNSYLVANIA Avenue

Winter Park, FL

2 bd1 ba709

Single Family

$699K

2260 COLDSTREAM Drive

Winter Park, FL

4 bd2 ba1,509

Single Family

$1.8M

1550 PALM Avenue

Winter Park, FL

4 bd4 ba2,706

Single Family

$450K

2181 LINDEN Road

Winter Park, FL

5 bd3 ba1,442

Single Family

$3.6M

276 DETMAR Drive

Winter Park, FL

4 bd5 ba4,202

Single Family

$415K

2126 ALBERT LEE Parkway

Winter Park, FL

3 bd2 ba1,187

Multi-Family

$660K

1016 ARAGON Avenue

Winter Park, FL

4 bd4 ba1,840

Multi-Family

$660K

1016 ARAGON Avenue

Winter Park, FL

4 bd4 ba1,840

Single Family

$689K

900 CARVER Street

Winter Park, FL

3 bd3 ba1,794

Single Family

$475K

2824 PRINCE JOHN Road

Winter Park, FL

2 bd2 ba1,438

Single Family

$340K

1941 OGLESBY Avenue

Winter Park, FL

2 bd1 ba780

Showing 1–50 of 163 · Page 1 of 4

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Local market guide

Winter Park Housing Market

Browse 163 active listings in Winter Park, Florida. The median list price for this active inventory is $575,000. Compare the price and property details reported in each listing.

Median list price $575,000 · Range $107,000–$6,900,000 · 163 active listings

Buyer questions

Frequently Asked Questions

How many active listings are available in Winter Park, Florida?

The current inventory contains 163 active listings in Winter Park, FL.

What is the average list price in Winter Park, Florida?

The average list price among current active listings in Winter Park, FL is $969,766. Current list prices range from $107,000 to $6,900,000.

What is the median list price in Winter Park?

The median list price among current active listings in Winter Park, FL is $575,000.

What is the average days on market for active listings in Winter Park?

Current active listings in Winter Park, FL report an average of 97 days on market.

Shape your search

Browse Winter Park by home feature

Homes with Solar Features Homes with EV Chargers Homes with Pools Waterfront Homes Homes with Views Homes with Recorded Price Reductions Listings Added to PropertySimple in the Past 7 Days Homes Built Since 2024

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Waterfront ListingsListings Marked Waterfront Listings in Mountain StatesSix-State Collection Multi-Family & Commercial ListingsListings by Property Type Listings with 3+ BedroomsThree or More Bedrooms Listings Priced at $1.5M+Listings by Asking Price Listings Built Since 2015Listings by Year Built

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Homes for Sale in Winter Park

Winter Park Real Estate at a Glance

Price Range

Homes to Explore

More from Winter Park

1257 WADING WATERS Circle

120 LONGBRANCH Road

2008 Houndslake Drive

2918 ANTIQUE OAKS Circle

450 LAKEWOOD Drive

1090 WILDMEADOW Run

2301 CONIFER Avenue

2487 HARBOUR Way

Homes for Sale in Winter Park

1306 S PENNSYLVANIA Avenue

1818 DOVER Road

1517 HARMON Avenue

2463 GRAND TETON Circle

1421 CHESTNUT Avenue

1421 CHESTNUT Avenue

2215 WOODCREST Drive

1166 PALMER Avenue

720 KILLARNEY BAY Court

1386 CLEMATIS Lane

7453 DANIEL WEBSTER Drive

1271 PALMER Avenue

1803 Barker Drive

3484 SEAGRAPE Drive

786 W CANTON Avenue

5080 SEMINOLE Avenue

504 W SWOOPE Avenue

2301 CONIFER Avenue

2383 SUN VALLEY Circle

447 N PHELPS Avenue

250 W READING Way

447 N PHELPS Avenue

2302 BARBADOS Drive

1257 WADING WATERS Circle

436 N WYMORE Road

3651 N GOLDENROD Road

200 S INTERLACHEN Avenue

1431 PALM Avenue

2349 SHADOWLAND Loop

2500 LEE Road

4039 COOL WATER Court

3020 ANTIQUE OAKS Circle

7839 UNIVERSITY GARDEN Drive

5108 LAZY OAKS Drive

2345 BROOKSHIRE Avenue

3020 NICHOLSON Drive

471 HOLT Avenue

2430 CHANTILLY Avenue

3302 ROYAL Street

500 N PENNSYLVANIA Avenue

2260 COLDSTREAM Drive

1550 PALM Avenue

2181 LINDEN Road

276 DETMAR Drive

2126 ALBERT LEE Parkway

1016 ARAGON Avenue

1016 ARAGON Avenue

900 CARVER Street

2824 PRINCE JOHN Road

1941 OGLESBY Avenue

Winter Park Housing Market

Frequently Asked Questions

How many active listings are available in Winter Park, Florida?

What is the average list price in Winter Park, Florida?

What is the median list price in Winter Park?

What is the average days on market for active listings in Winter Park?

Browse Winter Park by home feature

Explore by listing details

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