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Start here

Homes for sale by state
Home buying tips
Before you start looking
The buying timeline

Afford it

Today's mortgage rates
Mortgage calculator
How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
Inspections & appraisals
Closing costs, itemized
Find a buyer's agent

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What's my home worth?
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Get an instant cash offer
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What's worth fixing first
Find a seller's agent

3 beds New construction With a pool

3 Bedroom Homes in Winter Park, FL — Page 3

116 listings

3 Bedroom Homes in Winter Park, FL

3 Bedroom Homes in Winter Park, FL

24 of 116 Listings

3 Bedroom Homes in Winter Park, FL

24 of 116 Listings

21Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

$660,000

3 bd · 3 ba · 1,690 sqft

1256 Melissa Ct, Winter Park, FL

Wesley Morales · KELLER WILLIAMS REALTY AT THE PARKS

Price Reduced28Active

$599,000

3 bd · 2 ba · 1,232 sqft

1871 Bryan Ave, Winter Park, FL

Nick McKee · KELLER WILLIAMS WINTER PARK

Price Reduced25Active

$425,000

3 bd · 2 ba · 1,162 sqft

7384 Grand Ave, Winter Park, FL

Joseph Sipp · KELLER WILLIAMS WINTER PARK

Price Reduced19Active

$410,000

3 bd · 2 ba · 1,494 sqft

1955 Eland Ave, Winter Park, FL

Shelby Kirsch · REAL PROPERTY MANAGEMENT AND REALTY

Price Reduced29Active

$479,000

3 bd · 2 ba · 1,498 sqft

1652 Berkshire Ave, Winter Park, FL

Brian Teach · COLDWELL BANKER REALTY

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 Reduced75Active

$1,949,500

3 bd · 4 ba · 2,422 sqft

1420 Aloma Ave, Winter Park, FL

Alejandra Silva · METROPOLITAN R.E SOLUTIONS INC

$599,000

3 bd · 2 ba · 2,031 sqft

4026 Tenita Dr, Winter Park, FL

Ruby Davis · RUBY DAVIS, BROKER

Price Reduced27Active

$379,999

3 bd · 3 ba · 1,907 sqft

2017 Canny CV, Winter Park, FL

Janice Goulder · KELLER WILLIAMS WINTER PARK

$495,000

3 bd · 2 ba · 1,380 sqft

5316 Halyard Ct, Winter Park, FL

Neil Chetram · LA ROSA REALTY CW PROPERTIES L

Price Reduced11Active

$214,900

3 bd · 3 ba · 1,151 sqft

7413 Belle River Ct #3, Winter Park, FL

Ivan Tobon · OUTLET REALTY

Price ReducedOpen house Sun, Oct 4 · 12:00 PM48Active

$915,000

3 bd · 4 ba · 2,093 sqft

1927 S Lakemont Ave, Winter Park, FL

Abby Green · IAD REAL ESTATE

$510,000

3 bd · 3 ba · 1,669 sqft

1061 Aragon Ave #1061, Winter Park, FL

Lois Ann Cox, PA · WATSON REALTY CORP

$3,895,000

3 bd · 5 ba · 3,878 sqft

125 S Interlachen Ave #1, Winter Park, FL

Skip Kirst · COLLADO REAL ESTATE

Price Reduced36Active

$669,900

3 bd · 2 ba · 1,800 sqft

433 Gilbert Rd, Winter Park, FL

Amy Turner · KELLER WILLIAMS WINTER PARK

Price ReducedOpen house Sun, Oct 4 · 1:00 PM35Active

$430,000

3 bd · 2 ba · 1,645 sqft

3740 Hawthorne Ln, Winter Park, FL

John Crea · FLORIDA REALTY INVESTMENTS

$425,000

3 bd · 2 ba · 1,238 sqft

1886 Clematis Ln, Winter Park, FL

Steven Greening · EXP REALTY LLC

Price Reduced15Active

$410,000

3 bd · 2 ba · 1,483 sqft

5409 Albert Dr, Winter Park, FL

Raul Pino · SOVEREIGN REAL ESTATE GROUP

Price Reduced27Active

$334,000

3 bd · 2 ba · 1,149 sqft

3562 Bougainvillea Dr, Winter Park, FL

Tania Crandall · SHORESTONE PROPERTY GROUP

Price Reduced54Active

$464,000

3 bd · 2 ba · 1,737 sqft

2703 Tierra Cir, Winter Park, FL

Tony Ubaldini · EXP REALTY LLC

Price Reduced55Active

$389,000

3 bd · 3 ba · 1,907 sqft

2033 Canny CV, Winter Park, FL

Monica Puche · LPT REALTY, LLC

Price Reduced25Active

$395,000

3 bd · 2 ba · 1,201 sqft

2568 Lotafun Ave, Winter Park, FL

Randall Wolber, Jr · SIMPLE FEE LISTINGS LLC

$1,275,000

3 bd · 3 ba · 1,329 sqft

240 Killarney Dr, Winter Park, FL

Shandy Ortiz · PREMIER SOTHEBYS INT'L REALTY

$335,000

3 bd · 3 ba · 1,790 sqft

2526 Passamonte Dr #10F, Winter Park, FL

Kathi Thomas · LEGACY CORNERSTONE INC

1 2 3 4 5

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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.

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Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

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.