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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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Get an instant cash offer
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3 beds New construction With a pool

Homes with a Pool in Winter Park, FL — Page 2

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

Open house Sun, Oct 4 · 12:00 PM33

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Active

$380,000

3 bd · 2 ba · 1,277 sqft

4870 Seminole Ave, Winter Park, FL

Tamara Mazo Ferro · COLDWELL BANKER REALTY

$1,579,000

4 bd · 4 ba · 2,718 sqft

2417 Chantilly Ave, Winter Park, FL

Amanda Wood · RE/MAX EXCLUSIVE COLLECTION

Open house Sun, Oct 4 · 12:00 PM61Active

$2,195,000

4 bd · 5 ba · 2,850 sqft

1271 Palmer Ave, Winter Park, FL

JR Keelin · KELLY PRICE & COMPANY LLC

Price Reduced28Active

$440,000

4 bd · 2 ba · 2,189 sqft

2301 Conifer Ave, Winter Park, FL

Gregory Buckley · LOKATION

$4,400,000

4 bd · 6 ba · 3,720 sqft

702 Via Bella, Winter Park, FL

Mick Night · PREMIER SOTHEBY'S INTL. REALTY

$4,325,000

5 bd · 5 ba · 4,853 sqft

250 W Reading Way, Winter Park, FL

Brian Mitnik · RE/MAX 200 REALTY

$5,195,900

5 bd · 7 ba · 5,122 sqft

825 Palmer Ave, Winter Park, FL

Laura Earl · CORCORAN PREMIER REALTY

$2,725,000

5 bd · 5 ba · 3,784 sqft

1773 Walnut Ave, Winter Park, FL

Christopher Christensen · ONE LUXURY INTERNATIONAL LLC

Price Reduced89Active

$1,550,000

6 bd · 5 ba · 5,239 sqft

1257 Wading Waters Cir, Winter Park, FL

Rob Breese, III · RE/MAX TOWN & COUNTRY REALTY

$3,395,000

5 bd · 6 ba · 4,015 sqft

160 W Rockwood Way, Winter Park, FL

Alison Mosley · PREMIER SOTHEBY'S INTL. REALTY

Price Reduced69Active

$775,000

5 bd · 4 ba · 2,840 sqft

1164 Dodd Road, Winter Park, FL

Michael John Rothenburg · Charles Rutenberg Realty FTL

$495,000

4 bd · 2 ba · 1,756 sqft

3020 Nicholson Dr, Winter Park, FL

Kristin Duncan · CHARLES RUTENBERG REALTY ORLANDO

$5,999,990

4 bd · 5 ba · 3,880 sqft

2661 Via Tuscany, Winter Park, FL

Nohora Gomez · COLDWELL BANKER REALTY

Price ReducedOpen house Sun, Oct 4 · 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.

$739,777

4 bd · 2 ba · 2,267 sqft

4039 Cool Water Ct, Winter Park, FL

Karen Arbutine · RE/MAX CENTRAL REALTY

Price Reduced40Active

$529,000

4 bd · 2 ba · 1,845 sqft

2211 King Richards Ct, Winter Park, FL

Nicole Howell · FANNIE HILLMAN & ASSOCIATES

$1,598,000

4 bd · 4 ba · 2,916 sqft

2430 Chantilly Ave, Winter Park, FL

Kelly Price · KELLY PRICE & COMPANY LLC

$3,265,000

5 bd · 6 ba · 4,949 sqft

1761 Legion Dr, Winter Park, FL

Harry Pool, III · COLDWELL BANKER REALTY

$1,950,000

3 bd · 4 ba · 2,703 sqft

751 Pansy Ave, Winter Park, FL

Julie Christensen · ONE LUXURY INTERNATIONAL LLC

$245,000

2 bd · 2 ba · 913 sqft

1250 S Denning Dr #Unit 233, Winter Park, FL

Samuel Kingsford · STOCKWORTH REALTY GROUP

$3,600,000

4 bd · 5 ba · 4,202 sqft

276 Detmar Dr, Winter Park, FL

Melanie Johnston · CALL IT CLOSED INTL REALTY

$1,829,000

4 bd · 4 ba · 2,706 sqft

1550 Palm Ave, Winter Park, FL

Brian Mitnik · RE/MAX 200 REALTY

$1,350,000

6 bd · 6 ba · 5,021 sqft

1445 Via Sangro Pl, Winter Park, FL

Suzanne Seenandan · PREFERRED RE BROKERS III

1 2 3…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

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: 2026-10-03 20:36:50 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.