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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

Homes with a Pool in Winter Park, FL — Page 3

122 listings

Homes with a Pool in Winter Park, FL

Homes with a Pool in Winter Park, FL

24 of 122 Listings

Homes with a Pool in Winter Park, FL

24 of 122 Listings

31Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

$660,000

4 bd · 4 ba · 1,840 sqft

1016 Aragon Ave, Winter Park, FL

Pam Stewart · PALMANO GROUP RE BROKERAGE LLC

Price ReducedOpen house Sun, Oct 4 · 11:00 AM38Active

$575,000

4 bd · 2 ba · 1,936 sqft

7525 Lodge Pole Trl, Winter Park, FL

Amy Turner · KELLER WILLIAMS WINTER PARK

$860,000

5 bd · 4 ba · 3,284 sqft

120 Longbranch Rd, Winter Park, FL

Karen Albright · OPENDOOR BROKERAGE LLC

Price Reduced37Active

$525,000

4 bd · 2 ba · 2,126 sqft

2641 Carvell Ct, Winter Park, FL

Christina Perez · CHAMBERLAIN REALTY LLC

$520,000

4 bd · 2 ba · 1,774 sqft

1905 Bonanza Ct, Winter Park, FL

Bailey Briscoe · ORCHARD BROKERAGE, LLC

$2,700,000

5 bd · 5 ba · 3,588 sqft

648 Worthington Dr, Winter Park, FL

Christopher Christensen · ONE LUXURY INTERNATIONAL LLC

$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

$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

$1,699,000

4 bd · 4 ba · 2,530 sqft

2308 Mulbry Dr, Winter Park, FL

Brandon Geers · COMPASS FLORIDA LLC

$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

$1,725,000

4 bd · 4 ba · 3,727 sqft

1840 Bryan Ave, Winter Park, FL

Jennifer Draper · REAL BROKER, 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 Reduced92Active

$985,000

4 bd · 3 ba · 2,868 sqft

2667 Cochise Trl, Winter Park, FL

Beverley Kistler · COLDWELL BANKER REALTY

$1,749,000

4 bd · 4 ba · 2,715 sqft

2525 Lafayette Ave, Winter Park, FL

Matt Tomaszewski · CORCORAN PREMIER REALTY

$2,299,000

5 bd · 5 ba · 2,868 sqft

1840 Laurel Rd, Winter Park, FL

Matt Tomaszewski · CORCORAN PREMIER REALTY

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

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

$1,800,000

5 bd · 5 ba · 4,029 sqft

281 Brewer Ave, Winter Park, FL

John Henthorn · HENTHORN REAL ESTATE

1 2 3 4…6

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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.