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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
Buy before you sell

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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 2

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

13Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

$365,000

3 bd · 2 ba · 1,185 sqft

2136 Linden Rd, Winter Park, FL

Patty Hru · PAM REAL ESTATE

$380,000

3 bd · 1 ba · 1,143 sqft

2626 Ambergate Rd, Winter Park, FL

Brett Winters · OLDE TOWN BROKERS INC

$2,350,000

3 bd · 4 ba · 3,110 sqft

200 S Interlachen Ave #350, Winter Park, FL

Rhonda Chesmore · KELLY PRICE & COMPANY LLC

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 Reduced34Active

$629,000

3 bd · 2 ba · 1,783 sqft

508 Brechin Dr, Winter Park, FL

Mary Lowen · MTL REALTY LLC

$299,990

3 bd · 2 ba · 1,467 sqft

2275 Island Run, Winter Park, FL

Yukey Hoo · U KEY REALTY

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.

$425,000

3 bd · 3 ba · 1,755 sqft

2349 Shadowland Loop, Winter Park, FL

Lindsey Hudson · REAL BROKER, LLC

Price Reduced58Active

$1,295,000

3 bd · 4 ba · 2,191 sqft

720 Pansy Ave, Winter Park, FL

Nick McKee · KELLER WILLIAMS WINTER PARK

$365,000

3 bd · 3 ba · 1,861 sqft

7506 Cranes Creek Ct #30, Winter Park, FL

Sylvia Marchese · TRANSCONTINENTAL REALTY GROUP,

Open house Sun, Oct 4 · 2:00 PM31Active

$725,000

3 bd · 2 ba · 1,563 sqft

1850 Bryan Ave, Winter Park, FL

Jennifer King · CORCORAN PREMIER REALTY

$309,900

3 bd · 3 ba · 1,545 sqft

7530 Cranes Creek Ct, Winter Park, FL

Edward Hru · ROO REALTY LLC

Price Reduced49Active

$999,500

3 bd · 2 ba · 1,487 sqft

1220 Howell Branch Rd, Winter Park, FL

Fook Snipper · PARK PLACE REAL ESTATE

Price Reduced17Active

$269,900

3 bd · 2 ba · 1,197 sqft

3302 Royal St, Winter Park, FL

Robert Arnold, Jr · SAND DOLLAR REALTY GROUP INC

$1,600,000

3 bd · 3 ba · 2,733 sqft

2207 Kindel Ave, Winter Park, FL

Sandra Velasquez · THE SIMON SIMAAN GROUP

$1,950,000

3 bd · 4 ba · 2,703 sqft

751 Pansy Ave, Winter Park, FL

Julie Christensen · ONE LUXURY INTERNATIONAL LLC

Price Reduced21Active

$1,449,000

3 bd · 3 ba · 2,080 sqft

150 E Reading Way, Winter Park, FL

Wendy Williams Crumit · FANNIE HILLMAN & ASSOCIATES

Price Reduced27Active

$620,000

3 bd · 1 ba · 1,243 sqft

1416 Border Dr, Winter Park, FL

Audra Wilks · PREMIER SOTHEBY'S INTL. REALTY

Price ReducedOpen house Sun, Oct 4 · 12:00 PM31Active

$664,000

3 bd · 3 ba · 1,794 sqft

900 Carver St, Winter Park, FL

Farhad Haniff · EXP REALTY LLC

Price Reduced28Active

$349,000

3 bd · 3 ba · 1,872 sqft

7605 Aloma Pines Ct, Winter Park, FL

Simon Colak · USCO CAPITAL GROUP

Open house Sun, Oct 4 · 2:00 PM35Active

$899,000

3 bd · 3 ba · 2,022 sqft

1621 Chestnut Ave, Winter Park, FL

Kelly Price · KELLY PRICE & COMPANY LLC

$799,000

3 bd · 3 ba · 1,957 sqft

1278 S Pennsylvania Ave #13, Winter Park, FL

Nancy Merriam · PREMIER SOTHEBY'S INTL. REALTY

Price Reduced26Active

$399,995

3 bd · 3 ba · 1,782 sqft

2857 Clever Ln, Winter Park, FL

Justin Dalrymple, LLC · MAINFRAME REAL ESTATE

Price Reduced37Active

$495,000

3 bd · 2 ba · 2,047 sqft

1660 Gladiolas Dr, Winter Park, FL

Stephen Hachey · FLAT FEE MLS REALTY

1 2 3…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.