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

Selling Options

What's my home worth?
Compare selling options
Get an instant cash offer
Buy before you sell

Resources

How selling works
When should I sell?
Home selling tips
Pricing your home
What's worth fixing first
Find a seller's agent

Save search Advertise Sign In

Saved homes Saved searches Your tours Your inquiries Recently viewed Account settings

Registered offenders on the map

Show registered offenders

Registered offenders on the map

Show registered offenders

Safety & registry resources

Review official public-safety information for any area from these government sources:

U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
FBI: state sex-offender registry directory

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

Saved homes Saved searches Your tours Your inquiries Recently viewed Account settings

Rentals
Commercial

Registered offenders on the map

Show registered offenders

Selling Options

What's my home worth?
Compare selling options
Get an instant cash offer
Buy before you sell

Resources

How selling works
When should I sell?
Home selling tips
Pricing your home
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 4

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

10Active

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

$1,600,000

4 bd · 4 ba · 2,568 sqft

250 Killarney, Winter Park, FL

Nancy Rossman · FLORIDA PROPERTY SPECIALIST

Price Reduced38Active

$368,000

4 bd · 2 ba · 1,240 sqft

885 Carnation Dr, Winter Park, FL

Tashania Brown · RADIUS REALTY GROUP LLC

$2,549,000

5 bd · 5 ba · 3,479 sqft

1823 Sunset Dr, Winter Park, FL

Christopher Christensen · ONE LUXURY INTERNATIONAL LLC

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 Reduced57Active

$1,525,000

4 bd · 4 ba · 3,723 sqft

341 E Reading Way, Winter Park, FL

Wendy Williams Crumit · FANNIE HILLMAN & ASSOCIATES

$5,600,000

5 bd · 6 ba · 5,152 sqft

2228 Azalea Pl, Winter Park, FL

Quentin Green, II · COMPASS FLORIDA LLC

$199,900

1 bd · 1 ba · 582 sqft

151 North Orlando Avenue #142, Winter Park, FL

Chris Creegan · CREEGAN GROUP

Price Reduced31Active

$1,262,500

4 bd · 4 ba · 3,024 sqft

2015 Summerfield Rd, Winter Park, FL

Courtney Lindsay · UNITED REAL ESTATE PREFERRED

Price Reduced70Active

$2,995,000

5 bd · 7 ba · 4,168 sqft

1836 Whitehall Dr, Winter Park, FL

Bianca Khoury · PREMIER SOTHEBY'S INTL. REALTY

Price Reduced15Active

$420,000

3 bd · 2 ba · 1,676 sqft

1535 Lawndale Cir, Winter Park, FL

Raul Pino · SOVEREIGN REAL ESTATE GROUP

Price Reduced44Active

$2,050,000

5 bd · 5 ba · 2,889 sqft

240 N Phelps Ave, Winter Park, FL

Nick McKee · KELLER WILLIAMS WINTER PARK

Price Reduced67Active

$4,700,000

4 bd · 7 ba · 5,550 sqft

231 Chelton Cir, Winter Park, FL

Joseph Doher · BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

Price Reduced38Active

$1,369,000

5 bd · 4 ba · 2,446 sqft

1473 Berkshire Ave, Winter Park, FL

Gilson Rodrigues · KARDOSH REALTY

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

$3,500,000

4 bd · 4 ba · 4,036 sqft

2240 Venetian Way, Winter Park, FL

Johnny Hurlburt · COLDWELL BANKER REALTY

$500,000

4 bd · 3 ba · 2,031 sqft

2054 Eastbrook Blvd, Winter Park, FL

Melissa Stalzer · LPT REALTY, LLC

$695,000

4 bd · 3 ba · 2,312 sqft

715 S Ranger Blvd, Winter Park, FL

Chuck Tolfa · DAHLIA REALTY GROUP

Price Reduced42Active

$836,000

3 bd · 3 ba · 2,017 sqft

338 Blue Heron Dr, Winter Park, FL

Samuel Kingsford · STOCKWORTH REALTY GROUP

$6,000,000

5 bd · 8 ba · 7,397 sqft

1571 Woodland Ave, Winter Park, FL

Vonda Fields · CHARLES RUTENBERG REALTY ORLANDO

$2,375,000

5 bd · 5 ba · 3,989 sqft

946 Enclave Pl, Winter Park, FL

Matthew Burks · CORCORAN PREMIER REALTY

Price Reduced49Active

$1,049,900

5 bd · 5 ba · 3,652 sqft

1448 Lake Florence Way, Winter Park, FL

Abby Nelson · RE/MAX 200 REALTY

Price Reduced44Active

$999,000

4 bd · 5 ba · 2,638 sqft

616 Brechin Dr, Winter Park, FL

Alison Mosley · PREMIER SOTHEBY'S INTL. REALTY

$989,500

1 bd · 2 ba · 1,109 sqft

269 E Canton Ave #269, Winter Park, FL

Cathy Sawruk Williams · COLDWELL BANKER REALTY

$2,475,000

5 bd · 5 ba · 4,150 sqft

926 Enclave Pl, Winter Park, FL

Laura Earl · CORCORAN PREMIER REALTY

1…3 4 5 6

Explore Winter Park homes

By price

Homes Under $200K
Homes Under $300K
Homes Under $400K
Homes Under $500K
Homes Under $600K
Homes Under $700K
Homes Under $800K
Homes Under $900K
Homes Under $1M
Homes Under $1.25M
Homes Under $1.5M
Homes Under $1.75M
Homes Under $2M
Homes Under $2.25M
Homes Under $2.5M
Homes Over $3M
Luxury Homes

By bedrooms

2 Bedroom Homes
3 Bedroom Homes
4 Bedroom Homes
5 Bedroom Homes

By type

Single-Family Homes
Townhomes
Condos

By feature

New Construction Homes
Homes with a Pool
Waterfront Homes
Open Houses

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.

© 2026 Realty.com. All rights reserved.PrivacyTermsCalifornia Privacy RightsAccessibilityLicensing

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.