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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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Selling Options

What's my home worth?
Compare selling options
Get an instant cash offer
Buy before you sell

Resources

How selling works
When should I sell?
Home selling tips
Pricing your home
What's worth fixing first
Find a seller's agent

3 beds New construction With a pool

3 Bedroom Homes in Winter Park, FL

21 listings

3 Bedroom Homes in Winter Park, FL

3 Bedroom Homes in Winter Park, FL

21 Listings

3 Bedroom Homes in Winter Park, FL

21 Listings

21Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

$399,900

3 bd · 2 ba · 1,247 sqft

5405 Justine Way, Winter Park, FL

Yanira Suarez · LPT REALTY, LLC

Open house Sat, Oct 3 · 1:00 PM28Active

$769,900

3 bd · 3 ba · 2,145 sqft

1003 Golfside Dr, Winter Park, FL

Lina Paeres · QP HOMES REALTY LLC

Open house Sat, Oct 3 · 11:00 AM54Active

$659,000

3 bd · 2 ba · 2,265 sqft

5303 Pine Lily Cir, Winter Park, FL

Jonathan Casique · PM ELITE REALTY LLC

Open house Sat, Oct 3 · 11:00 AM33Active

$380,000

3 bd · 2 ba · 1,277 sqft

4870 Seminole Ave, Winter Park, FL

Tamara Mazo Ferro · COLDWELL BANKER REALTY

Price ReducedOpen house Sat, Oct 3 · 12:00 AM38Active

$659,900

3 bd · 2 ba · 1,420 sqft

274 N Ranger Blvd, Winter Park, FL

Shannon Lee · EXPLORE FLORIDA REALTY SERVICES LLC

Price Reduced54Active

$1,095,000

3 bd · 3 ba · 1,873 sqft

1922 Hammerlin Ave, Winter Park, FL

Felicia Donatelli · PALM PROPERTIES OF CF, INC.

$1,950,000

3 bd · 4 ba · 2,703 sqft

751 Pansy Ave, Winter Park, FL

Julie Christensen · ONE LUXURY INTERNATIONAL LLC

$599,000

3 bd · 2 ba · 2,031 sqft

4026 Tenita Dr, Winter Park, FL

Ruby Davis · RUBY DAVIS, BROKER

$495,000

3 bd · 2 ba · 1,380 sqft

5316 Halyard Ct, Winter Park, FL

Neil Chetram · LA ROSA REALTY CW PROPERTIES L

Price Reduced36Active

$669,900

3 bd · 2 ba · 1,800 sqft

433 Gilbert Rd, Winter Park, FL

Amy Turner · KELLER WILLIAMS WINTER PARK

Price Reduced35Active

$430,000

3 bd · 2 ba · 1,645 sqft

3740 Hawthorne Ln, Winter Park, FL

John Crea · FLORIDA REALTY INVESTMENTS

Price Reduced15Active

$410,000

3 bd · 2 ba · 1,483 sqft

5409 Albert Dr, Winter Park, FL

Raul Pino · SOVEREIGN REAL ESTATE GROUP

Price ReducedOpen house Sun, Oct 4 · 11:00 AM54Active

$464,000

3 bd · 2 ba · 1,737 sqft

2703 Tierra Cir, Winter Park, FL

Tony Ubaldini · EXP REALTY LLC

Price Reduced34Active

$539,000

3 bd · 3 ba · 1,602 sqft

7641 Village Green Drive, Winter Park, FL

Jannett Jhasmin Marten · Compass Florida, LLC

Price Reduced15Active

$420,000

3 bd · 2 ba · 1,676 sqft

1535 Lawndale Cir, Winter Park, FL

Raul Pino · SOVEREIGN REAL ESTATE GROUP

Price ReducedOpen house Sat, Oct 3 · 1:00 PM37Active

$1,499,000

3 bd · 5 ba · 2,756 sqft

641 Northwood Circle, Winter Park, FL

Sandra Cuba · PREMIER SOTHEBY'S INTL. REALTY

Price ReducedOpen house Sat, Oct 3 · 1:00 PM42Active

$836,000

3 bd · 3 ba · 2,017 sqft

338 Blue Heron Dr, Winter Park, FL

Samuel Kingsford · STOCKWORTH REALTY GROUP

Price Reduced23Active

$388,000

3 bd · 2 ba · 1,122 sqft

1092 Eastbrook Blvd, Winter Park, FL

Eva Firios · JC FLORIDA REALTY LLC

Price Reduced47Active

$612,500

3 bd · 2 ba · 1,785 sqft

2708 Lion Heart Rd, Winter Park, FL

Navid Rokh · EQUITYPRO LLC

Price Reduced38Active

$619,500

3 bd · 3 ba · 1,539 sqft

2758 Banchory Rd, Winter Park, FL

Erwin Vargas · MR VARGAS PROPERTY MANAGEMENT LLC

$460,000

3 bd · 2 ba · 1,263 sqft

5331 Oak Ct, Winter Park, FL

Nataliya Voroshylo Hylton · CHARLES RUTENBERG REALTY ORLANDO

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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

BeachesMLS: All listings featuring the BMLS logo are provided by Beaches MLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Information is provided exclusively for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Listing information ©2026 Beaches Multiple Listing Service®. All Rights Reserved. Data Last Updated: 2026-09-26 15:38:47 UTC
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.