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3 beds New construction With a pool

351 listings

Homes for Sale in Winter Park, FL

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24 of 351 Listings

Map

24 of 351 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

86Active

$739,000

2 bd · 2 ba · 1,311 sqft

250 Carolina Ave #205, Winter Park, FL

Troy Hensley · BHHS FLORIDA REALTY

26Active

$520,000

4 bd · 2 ba · 1,774 sqft

1905 Bonanza Ct, Winter Park, FL

Bailey Briscoe · ORCHARD BROKERAGE, LLC

5Active

$2,700,000

5 bd · 5 ba · 3,588 sqft

648 Worthington Dr, Winter Park, FL

Christopher Christensen · ONE LUXURY INTERNATIONAL LLC

Price Reduced28Active

$599,000

3 bd · 2 ba · 1,232 sqft

1871 Bryan Ave, Winter Park, FL

Nick McKee · KELLER WILLIAMS WINTER PARK

41Active

$770,000

4 bd · 3 ba · 2,192 sqft

2286 Marsh Sedge Ln, Winter Park, FL

Brandon Geers · COMPASS FLORIDA LLC

Price Reduced25Active

$425,000

3 bd · 2 ba · 1,162 sqft

7384 Grand Ave, Winter Park, FL

Joseph Sipp · KELLER WILLIAMS WINTER PARK

Price ReducedOpen house Sun, Oct 4 · 10:00 AM38Active

$825,000

2 bd · 2 ba · 1,540 sqft

1431 Palm Ave, Winter Park, FL

Kelsey Payton · ALL REAL ESTATE & INVESTMENTS

Price Reduced19Active

$410,000

3 bd · 2 ba · 1,494 sqft

1955 Eland Ave, Winter Park, FL

Shelby Kirsch · REAL PROPERTY MANAGEMENT AND REALTY

16Active

$575,000

4 bd · 3 ba · 1,745 sqft

2627 Ambergate Rd, Winter Park, FL

Steven Thetford · KELLER WILLIAMS WINTER PARK

Price Reduced72Active

$3,750,000

4 bd · 3 ba · 3,377 sqft

2622 Lake Howell Ln, Winter Park, FL

Brian Hyser · THE AGENCY FL

Price Reduced29Active

$479,000

3 bd · 2 ba · 1,498 sqft

1652 Berkshire Ave, Winter Park, FL

Brian Teach · COLDWELL BANKER REALTY

11Active

$3,890,000

6 bd · 5 ba · 4,677 sqft

620 Virginia Dr, Winter Park, FL

Julie Christensen · ONE LUXURY INTERNATIONAL LLC

Price Reduced41Active

$1,699,000

4 bd · 4 ba · 3,307 sqft

2343 Versailles Ave, Winter Park, FL

MaryStuart Day · FANNIE HILLMAN & ASSOCIATES

Price Reduced18Active

$395,000

3 bd · 2 ba · 1,310 sqft

5588 Garden Grove Cir, Winter Park, FL

Victor Nguyen · CHARLES RUTENBERG REALTY ORLANDO

Price Reduced24Active

$247,000

2 bd · 2 ba · 1,316 sqft

2477 Tahoe Cir #2477, Winter Park, FL

Kyle Clark · RE/MAX TOWN & COUNTRY REALTY

12Active

$1,699,000

4 bd · 4 ba · 2,530 sqft

2308 Mulbry Dr, Winter Park, FL

Brandon Geers · COMPASS FLORIDA LLC

35Active

$1,625,000

5 bd · 5 ba · 3,133 sqft

2407 Lafayette Ave, Winter Park, FL

Lisa Fleming · FANNIE HILLMAN & ASSOCIATES

Price Reduced11Active

$4,350,000

5 bd · 6 ba · 4,827 sqft

857 Brock St, Winter Park, FL

Julie Christensen · ONE LUXURY INTERNATIONAL LLC

Price Reduced75Active

$1,949,500

3 bd · 4 ba · 2,422 sqft

1420 Aloma Ave, Winter Park, FL

Alejandra Silva · METROPOLITAN R.E SOLUTIONS INC

34Active

$575,000

2 bd · 3 ba · 1,851 sqft

1071 Aragon Ave, Winter Park, FL

Greg Vazzana · FANNIE HILLMAN & ASSOCIATES

53Active

$1,725,000

4 bd · 4 ba · 3,727 sqft

1840 Bryan Ave, Winter Park, FL

Jennifer Draper · REAL BROKER, LLC

1Active

$180,000

1 bd · 1 ba · 638 sqft

1695 Lee Rd #D107, Winter Park, FL

Hoover Yap · PRIMESTATE REALTY, INC.

Price Reduced37Active

$665,000

4 bd · 3 ba · 1,770 sqft

1122 Wildmeadow Run, Winter Park, FL

Ken Pozek · REAL BROKER, LLC

Price Reduced37Active

$279,900

2 bd · 3 ba · 1,236 sqft

5210 Lazy Oaks Dr, Winter Park, FL

Karen Sweat · IHOME REALTY FL LLC

1…6 7 8…15

Listing data & MLS disclosures

Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Winter Park housing market

September 2026 · This period is still settling

Selling at 97.9% of asking price

Buyers here are paying below asking. MLS · 73 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 16, 2026

Median sale price: $632,500$389,375–$1,088,750 typical range
Price per sq. ft.: $379
Sales: 60
Paid in cash: 50.0%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $630,000

Winter Park, FL community profile

Population: 31,855
Median income: $98,252
Housing units: 15,404
People per sq. mi.: 1,409.5
Area: 22.6 sq. mi.

Source: HJN community data

Explore Winter Park homes

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Homes Under $200K
Homes Under $300K
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Homes Under $1M
Homes Under $1.25M
Homes Under $1.5M
Homes Under $1.75M
Homes Under $2M
Homes Under $2.25M
Homes Under $2.5M

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Homes Over $3M

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New Construction Homes
Homes with a Pool
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Nearby areas

ZIP codes

34747 (2,170)
34787 (1,390)
34746 (1,138)
33897 (841)
34771 (693)
32757 (595)
32771 (551)
34714 (551)

Cities

Orlando (3,872)
ORLANDO (3,805)
Kissimmee (2,015)
KISSIMMEE (1,990)
Winter Garden (694)
WINTER GARDEN (648)
Davenport (614)
DAVENPORT (613)

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Listing data & MLS disclosures

Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Winter Park, FL community profile

Population: 31,855
Median income: $98,252
Housing units: 15,404
People per sq. mi.: 1,409.5
Area: 22.6 sq. mi.

Source: HJN community data

Winter Park housing market

September 2026 · This period is still settling

Selling at 97.9% of asking price

Buyers here are paying below asking. MLS · 73 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 16, 2026

Median sale price: $632,500$389,375–$1,088,750 typical range
Price per sq. ft.: $379
Sales: 60
Paid in cash: 50.0%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $630,000

Homes for sale

383

Median days on market

17 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: 40.9%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

Median home size: 1,731 sq. ft.

Winter Park, FL Homes for Sale — Page 7 | Realty.com

Nearby areas

ZIP codes

34747 (2,170)
34787 (1,390)
34746 (1,138)
33897 (841)
34771 (693)
32757 (595)
32771 (551)
34714 (551)

Cities

Orlando (3,872)
ORLANDO (3,805)
Kissimmee (2,015)
KISSIMMEE (1,990)
Winter Garden (694)
WINTER GARDEN (648)
Davenport (614)
DAVENPORT (613)