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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 4

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

Price Reduced21

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Active

$1,999,900

3 bd · 2 ba · 1,765 sqft

1133 Bella Lago CV, Winter Park, FL

Hang Kendall · LPT REALTY, LLC

Price Reduced13Active

$270,000

3 bd · 3 ba · 1,803 sqft

2487 Harbour Way, Winter Park, FL

Joel Garay · LOKATION

Price Reduced28Active

$1,495,000

3 bd · 3 ba · 1,944 sqft

462 W Lyman Ave, Winter Park, FL

Mick Night · PREMIER SOTHEBY'S INTL. REALTY

Price Reduced37Active

$250,000

3 bd · 2 ba · 1,311 sqft

2450 Grand Teton Cir #2450, Winter Park, FL

John Campese · CHARLES RUTENBERG REALTY ORLANDO

Price Reduced30Active

$439,900

3 bd · 1 ba · 1,508 sqft

2041 Jewell Ave, Winter Park, FL

Martha Coronel · IAD REAL ESTATE

Price Reduced30Active

$549,900

3 bd · 2 ba · 1,837 sqft

1003 Lake Bell Dr, Winter Park, FL

Bryan Douglas · KELLER WILLIAMS REALTY AT THE PARKS

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 Reduced41Active

$925,000

3 bd · 3 ba · 2,434 sqft

1138 S Pennsylvania Ave, Winter Park, FL

George Stringer · COLDWELL BANKER REALTY

Price Reduced26Active

$449,900

3 bd · 2 ba · 1,248 sqft

259 Orange Terrace Drive, Winter Park, FL

Jo Ann Lamar · PREMIER SOTHEBY'S INTL. REALTY

Price Reduced70Active

$2,695,000

3 bd · 4 ba · 3,286 sqft

660 W Morse Blvd, Winter Park, FL

Jennifer Sloan · COMPASS FLORIDA LLC

$1,399,000

3 bd · 3 ba · 2,585 sqft

512 W Swoope Ave, Winter Park, FL

Carmen Quintana · COLDWELL BANKER REALTY

Price Reduced39Active

$1,775,000

3 bd · 4 ba · 3,112 sqft

101 S New York Ave #311, Winter Park, FL

Tiffany Grindstaff · KELLY PRICE & COMPANY LLC

Price Reduced19Active

$379,000

3 bd · 2 ba · 1,285 sqft

1605 Puritan Ave, Winter Park, FL

Angelica Tomlinson LLC · CENTURY 21 CARIOTI

$849,000

3 bd · 3 ba · 1,904 sqft

437 N Capen Ave, Winter Park, FL

Brandon Geers · COMPASS FLORIDA LLC

Price Reduced20Active

$384,900

3 bd · 2 ba · 1,667 sqft

1840 Aster Dr, Winter Park, FL

Brendon Spalding · KONA REALTY SERVICES LLC

Price Reduced38Active

$810,000

3 bd · 4 ba · 2,030 sqft

1265 Arlington Pl, Winter Park, FL

Erika Beerbower · FANNIE HILLMAN & ASSOCIATES

Price Reduced15Active

$420,000

3 bd · 2 ba · 1,676 sqft

1535 Lawndale Cir, Winter Park, FL

Raul Pino · SOVEREIGN REAL ESTATE GROUP

Price Reduced29Active

$494,900

3 bd · 2 ba · 1,565 sqft

2715 Prince John Rd, Winter Park, FL

Donna Peebles · VIA PROPERTIES LLC

$3,150,000

3 bd · 5 ba · 3,244 sqft

125 S Interlachen Ave #2, Winter Park, FL

Erin Legler · CHARLES RUTENBERG REALTY ORLANDO

Price ReducedOpen house Tue, Oct 6 · 12:00 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 Reduced29Active

$2,625,000

3 bd · 4 ba · 3,048 sqft

413 W Morse Blvd, Winter Park, FL

AV Blalock · COLDWELL BANKER REALTY

Price Reduced57Active

$399,900

3 bd · 2 ba · 1,366 sqft

5503 Albert Dr, Winter Park, FL

Fernando Perez de Armas · AXEN REALTY, LLC

Price Reduced63Active

$649,900

3 bd · 2 ba · 1,370 sqft

840 W Canton Ave, Winter Park, FL

Ken Pozek · REAL BROKER, LLC

Price Reduced37Active

$535,000

3 bd · 4 ba · 1,937 sqft

1250 Formosa Ave, Winter Park, FL

Jeanine Louis, LLC · EXP REALTY LLC

1…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

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.