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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

Save search Advertise Sign In

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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

Homes with a Pool in Winter Park, FL — Page 5

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

9Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

$2,300,000

5 bd · 5 ba · 3,865 sqft

938 Enclave Pl, Winter Park, FL

Laura Earl · CORCORAN PREMIER REALTY

$3,300,000

5 bd · 6 ba · 3,421 sqft

1627 Mizell Ave, Winter Park, FL

Bianca Khoury · PREMIER SOTHEBY'S INTL. REALTY

Price Reduced23Active

$388,000

3 bd · 2 ba · 1,122 sqft

1092 Eastbrook Blvd, Winter Park, FL

Eva Firios · JC FLORIDA REALTY LLC

$2,275,000

5 bd · 5 ba · 3,813 sqft

930 Enclave Pl, Winter Park, FL

Matthew Burks · CORCORAN PREMIER REALTY

$2,500,000

5 bd · 6 ba · 4,572 sqft

450 Lakewood Dr, Winter Park, FL

Vonda Fields · CHARLES RUTENBERG REALTY ORLANDO

$1,599,000

5 bd · 4 ba · 3,028 sqft

1864 Grinnell Ter, Winter Park, FL

Robyn Brehne-Glass · COLDWELL BANKER REALTY

Price Reduced85Active

$3,995,000

4 bd · 6 ba · 4,066 sqft

1441 Cardinal Ct, Winter Park, FL

Damian Bergler · CHARLES RUTENBERG REALTY ORLANDO

Price Reduced39Active

$1,299,000

4 bd · 4 ba · 2,459 sqft

102 Bell Pl, Winter Park, FL

Nick McKee · KELLER WILLIAMS WINTER PARK

Price Reduced36Active

$1,595,000

4 bd · 4 ba · 3,048 sqft

1570 Palmer Ave, Winter Park, FL

David Auerbach · PARK TOWN REAL ESTATE LLC

Price Reduced51Active

$2,495,000

4 bd · 4 ba · 3,553 sqft

541 W Canton Ave, Winter Park, FL

Bianca Khoury · PREMIER SOTHEBY'S INTL. REALTY

Price Reduced46Active

$1,750,000

4 bd · 4 ba · 3,249 sqft

1750 Carollee Lane, Winter Park, FL

Michelle Hochfelder · PREMIER SOTHEBY'S INTL. REALTY

$2,070,000

5 bd · 5 ba · 3,617 sqft

914 Enclave Pl, Winter Park, FL

Matthew Burks · CORCORAN PREMIER REALTY

Price Reduced42Active

$1,649,000

4 bd · 4 ba · 2,807 sqft

1903 N Park Ave, Winter Park, FL

Chris Creegan · CREEGAN GROUP

Price Reduced20Active

$419,000

4 bd · 2 ba · 1,376 sqft

501 Heritage Blvd, Winter Park, FL

Bernardo Carrasquel · EXP REALTY LLC

Price Reduced52Active

$3,275,000

4 bd · 6 ba · 4,683 sqft

1581 Forest Ave, Winter Park, FL

Julie Christensen · ONE LUXURY INTERNATIONAL LLC

Price Reduced47Active

$612,500

3 bd · 2 ba · 1,785 sqft

2708 Lion Heart Rd, Winter Park, FL

Navid Rokh · EQUITYPRO LLC

$6,900,000

6 bd · 7 ba · 6,396 sqft

1260 Alabama Dr, Winter Park, FL

Kelly Price · KELLY PRICE & COMPANY LLC

Price Reduced74Active

$829,500

4 bd · 2 ba · 3,950 sqft

1521 Heron Wood Pl, Winter Park, FL

Ronald Trotter · RE/MAX INNOVATION

$1,750,000

4 bd · 3 ba · 2,350 sqft

1840 Anzle Ave, Winter Park, FL

Oscar Rodriguez · B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE

$299,999

2 bd · 1 ba · 710 sqft

151 N Orlando Ave #118, Winter Park, FL

Adriana Montes · FLORIDA DREAMS REALTY GRP INC

Price Reduced37Active

$182,900

2 bd · 2 ba · 927 sqft

205 Lewfield Cir #205, Winter Park, FL

Eimi Moreno Carrera · LPT REALTY, LLC

Price Reduced34Active

$485,000

4 bd · 2 ba · 2,092 sqft

2217 Sussex Rd, Winter Park, FL

Justin Hilton · PREFERRED REAL ESTATE BROKERS

Price Reduced12Active

$3,600,000

5 bd · 5 ba · 3,719 sqft

207 E Kings Way, Winter Park, FL

Julie Christensen · ONE LUXURY INTERNATIONAL LLC

Price Reduced39Active

$3,075,000

5 bd · 6 ba · 3,863 sqft

1821 Englewood Rd, Winter Park, FL

Mick Night · PREMIER SOTHEBY'S INTL. REALTY

1…4 5 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 23, 2026

Median sale price: $602,500$441,750–$1,016,350 typical range
Price per sq. ft.: $358
Sales: 78
Paid in cash: 46.2%

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.