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Homes with a Pool in Winter Park, FL

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3 beds New construction With a pool

Homes with a Pool in Winter Park, FL

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24 of 118 Listings

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24 of 118 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Open house Wed, Oct 28 · 5:00 PM29Active
$410,000
3 bd · 2 ba · 1,318 sqft
1021 Princess Gate Blvd, Winter Park, FL
Joseph Doher · BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY
New41Active
$1,050,000
4 bd · 3 ba · 2,787 sqft
1735 Demetree Dr, Winter Park, FL
Melissa Johnson · EXP REALTY LLC
New56Active
$5,995,000
5 bd · 6 ba · 5,476 sqft
1200 Via Salerno, Winter Park, FL
Kelly Price · KELLY PRICE & COMPANY LLC

12Active
$419,900
4 bd · 2 ba · 1,427 sqft
603 Carnation Dr, Winter Park, FL
William Ward · A-WARD WINNING REALTY LLC
56Active
$4,500,000
5 bd · 6 ba · 4,754 sqft
1631 Hillcrest Ave, Winter Park, FL
Chris Quarles · CHRIS QUARLES PROPERTIES LLC
32Active
$699,900
3 bd · 2 ba · 1,666 sqft
1884 Jessica Ct, Winter Park, FL
Abby Nelson · RE/MAX 200 REALTY
Open house Sat, Oct 31 · 11:00 AM26Active
$509,999
3 bd · 2 ba · 1,460 sqft
808 Densmore Dr, Winter Park, FL
Karly Campbell · NOVA REAL ESTATE SERVICES INC
Open house Sat, Oct 31 · 11:00 AM98Active
$3,195,000
4 bd · 6 ba · 4,311 sqft
1825 Whitehall Dr, Winter Park, FL
Ahmad Hassan, PA · COMPASS FLORIDA LLC
Price Reduced33Active
$515,000
3 bd · 3 ba · 1,602 sqft
7641 Village Green Drive, Winter Park, FL
Jannett Jhasmin Marten · Compass Florida, LLC
76Active
$3,495,000
5 bd · 6 ba · 4,483 sqft
1600 Legion Dr, Winter Park, FL
Brian Teach · COLDWELL BANKER REALTY
16Active
$2,629,000
5 bd · 5 ba · 3,682 sqft
1681 Woodland Ave, Winter Park, FL
Christopher Christensen · ONE LUXURY INTERNATIONAL LLC
58Active
$1,349,000
4 bd · 4 ba · 2,575 sqft
1939 Woodcrest Dr, Winter Park, FL
Jose Martinez Rivera LLC · LA ROSA REALTY PREMIER LLC
30Active
$415,900
3 bd · 2 ba · 1,412 sqft
3409 Ferndell Dr, Winter Park, FL
Veronica Lewis · LPT REALTY, LLC
Price Reduced16Active
$314,000
3 bd · 2 ba · 1,229 sqft
1740 Puritan Ave, Winter Park, FL
Brenda Brooks · KELLER WILLIAMS REALTY SMART 1
44Active
$1,249,000
6 bd · 6 ba · 5,021 sqft
1445 Via Sangro Pl, Winter Park, FL
Kevin Asenjo · COLDWELL BANKER REALTY
70Active
$6,000,000
5 bd · 7 ba · 4,806 sqft
1011 McKean Cir, Winter Park, FL
Clay Wooten · UNITED REAL ESTATE PREFERRED
Open house Sat, Oct 31 · 2:00 PM47Active
$950,000
2 bd · 2 ba · 1,947 sqft
1411 Devon Rd, Winter Park, FL
Harif Hazera LLC · PREMIER SOTHEBY'S INTL. REALTY
Open house Sat, Oct 31 · 12:00 PM67Active
$3,390,000
5 bd · 7 ba · 4,520 sqft
1751 Glencoe Rd, Winter Park, FL
Christopher Christensen · ONE LUXURY INTERNATIONAL LLC
38Active
$1,399,900
4 bd · 4 ba · 2,984 sqft
1737 Indiana Ave, Winter Park, FL
Tori Nguyen · LOKATION
51Active
$519,900
4 bd · 3 ba · 1,842 sqft
731 Bongart Rd, Winter Park, FL
Steven Koleno · BEYCOME OF FLORIDA LLC
25Active
$255,000
2 bd · 2 ba · 1,026 sqft
1500 Gay Rd #26-C, Winter Park, FL
Lianna Dangelo · SOTERA LIVING
Open house Thu, Oct 29 · 5:30 PM46Active
$3,250,000
5 bd · 6 ba · 4,459 sqft
2823 Parkland Circle, Winter Park, FL
Sandra Cuba · PREMIER SOTHEBY'S INTL. REALTY
Price Reduced28Active
$469,900
4 bd · 3 ba · 2,088 sqft
2020 Leanne Ct, Winter Park, FL
Ileana Perez · HOUWZER INC
48Active
$649,000
3 bd · 2 ba · 1,573 sqft
518 Gilbert Rd, Winter Park, FL
Monika Kenney · PALMANO GROUP RE BROKERAGE LLC

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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: 2026-10-23 14:55:39 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.

About Homes with a Pool in Winter Park, FL

Homes with a Pool in Winter Park, FL: 118 active listings as of October 28, 2026, 22:32 UTC.

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Winter Park housing market

September 2026

Selling at 97.9% of asking price

Buyers here are paying below asking. MLS · 84 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 30, 2026

Median sale price: $566,750$404,625–$1,046,250 typical range
Price per sq. ft.: $342
Sales: 108
Paid in cash: 43.5%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $630,000
Homes for sale: 383
Median days on market: 18 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: 27.8%

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.

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

Explore Winter Park homes

By price

Homes Under $200K
Homes Under $300K

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.

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: 2026-10-23 14:55:39 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

Selling at 97.9% of asking price

Buyers here are paying below asking. MLS · 84 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 30, 2026

Median sale price: $566,750$404,625–$1,046,250 typical range
Price per sq. ft.: $342
Sales: 108
Paid in cash: 43.5%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $630,000
Homes for sale: 383
Median days on market: 18 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: 27.8%

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.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

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Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas