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Start here

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Before you start looking
The buying timeline

Afford it

Today's mortgage rates
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How much can I afford?
Get pre-approved

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Writing a winning offer
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Closing costs, itemized
Find a buyer's agent

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3 beds New construction With a pool

Homes with a Pool in Winter Garden, FL — Page 7

179 listings

Homes with a Pool in Winter Garden, FL

Homes with a Pool in Winter Garden, FL

24 of 179 Listings

Homes with a Pool in Winter Garden, FL

24 of 179 Listings

Price Reduced77

Your Winter Garden agent

VF

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

The Figueroa Team LLC. eXp Realty, LLC

Active

$2,700,000

7 bd · 7 ba · 6,400 sqft

15522 Shorebird Ln, Winter Garden, FL

Jun Jie Zhao · EAST PEARL REALTY

Price Reduced43Active

$969,000

3 bd · 3 ba · 2,346 sqft

14140 Country Estate Drive, Winter Garden, FL

Erin Rison · CHARLES RUTENBERG REALTY ORLANDO

Price Reduced43Active

$969,000

3 bd · 3 ba · 2,346 sqft

14140 Country Estate Dr, Winter Garden, FL

Erin Rison · CHARLES RUTENBERG REALTY ORLANDO

Price Reduced31Active

$799,900

5 bd · 3 ba · 3,954 sqft

13412 Fox Glove Street, Winter Garden, FL

Juli Onorata · CHARLES RUTENBERG REALTY ORLANDO

Price Reduced31Active

$799,900

5 bd · 3 ba · 3,954 sqft

13412 Fox Glove St, Winter Garden, FL

Juli Onorata · CHARLES RUTENBERG REALTY ORLANDO

Price Reduced63Active

$2,150,000

5 bd · 5 ba · 4,072 sqft

7701 Summerlake Pointe Boulevard, Winter Garden, FL

Vanessa Ferreira · WRA BUSINESS & REAL ESTATE

Price Reduced63Active

$2,150,000

5 bd · 5 ba · 4,072 sqft

7701 Summerlake Pointe Blvd, Winter Garden, FL

Vanessa Ferreira · WRA BUSINESS & REAL ESTATE

$1,150,000

4 bd · 3 ba · 2,986 sqft

16071 Barkly Ridge Court, Winter Garden, FL

Thiago De Ataide · WRA BUSINESS & REAL ESTATE

$1,150,000

4 bd · 3 ba · 2,986 sqft

16071 Barkly Ridge Ct, Winter Garden, FL

Thiago De Ataide · WRA BUSINESS & REAL ESTATE

Price Reduced68Active

$1,625,000

5 bd · 5 ba · 4,365 sqft

2450 Dahlgren Way, Winter Garden, FL

Keegan Siegfried · LPT REALTY, LLC

Price Reduced61Active

$1,499,990

5 bd · 5 ba · 4,365 sqft

2450 Dahlgren Way, Winter Garden, FL

Trinh Minh A Nguyen · LPT REALTY, LLC

Price Reduced40Active

$1,775,000

6 bd · 4 ba · 3,629 sqft

17224 Old Country Ln, Winter Garden, FL

Kerstin Crow · LOKATION

Price Reduced40Active

$1,775,000

6 bd · 4 ba · 3,629 sqft

17224 Old Country Lane, Winter Garden, FL

Kerstin Crow · LOKATION

Price Reduced21Active

$1,100,000

4 bd · 4 ba · 3,077 sqft

9312 Holliston Creek Pl, Winter Garden, FL

Karine Nascimento · K REALTY

Price Reduced21Active

$1,100,000

4 bd · 4 ba · 3,077 sqft

9312 Holliston Creek Place, Winter Garden, FL

Karine Nascimento · K REALTY

Price Reduced76Active

$1,085,000

5 bd · 5 ba · 3,886 sqft

15625 Sylvester Palm Dr, Winter Garden, FL

Deep Mehta, PA · EXP REALTY LLC

Price Reduced76Active

$1,085,000

5 bd · 5 ba · 3,886 sqft

15625 Sylvester Palm Drive, Winter Garden, FL

Deep Mehta, PA · EXP REALTY LLC

Price Reduced12Active

$625,000

4 bd · 2 ba · 1,924 sqft

17134 Lake Ingram Road, Winter Garden, FL

Cynthia Griffin · OPTIMA ONE REALTY, INC.

Price Reduced12Active

$625,000

4 bd · 2 ba · 1,924 sqft

17134 Lake Ingram Rd, Winter Garden, FL

Cynthia Griffin · OPTIMA ONE REALTY, INC.

Price Reduced79Active

$849,900

4 bd · 4 ba · 2,800 sqft

15672 Shorebird Ln, Winter Garden, FL

Helen Thompson · RE/MAX SELECT GROUP

Price Reduced79Active

$849,900

4 bd · 4 ba · 2,800 sqft

15672 Shorebird Lane, Winter Garden, FL

Helen Thompson · RE/MAX SELECT GROUP

Price Reduced31Active

$629,000

3 bd · 3 ba · 2,278 sqft

1608 Highbanks Circle, Winter Garden, FL

Rosa Aponte · EMPIRE NETWORK REALTY

Price Reduced32Active

$1,200,000

4 bd · 3 ba · 2,171 sqft

205 Surprise Dr, Winter Garden, FL

Alison Scorsone · RE/MAX PRIME PROPERTIES

Price Reduced32Active

$1,200,000

4 bd · 3 ba · 2,171 sqft

205 Surprise Drive, Winter Garden, FL

Alison Scorsone · RE/MAX PRIME PROPERTIES

1…6 7 8

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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 Winter Garden agent

VF

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

The Figueroa Team LLC. eXp Realty, LLC

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 Garden, FL community profile

Population: 50,261
Median income: $102,195
Housing units: 18,962
People per sq. mi.: 562.2
Area: 89.4 sq. mi.

Source: HJN community data

Winter Garden housing market

September 2026 · This period is still settling

Selling at 98.1% of asking price

Buyers here are paying below asking. MLS · 221 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 23, 2026

Median sale price: $632,500$500,125–$1,055,625 typical range
Price per sq. ft.: $259
Sales: 194
Paid in cash: 39.7%

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

Median list price: $565,000
Homes for sale: 795
Median days on market: 37 days

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

Year-over-year: 11.2%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

Median home size: 2,211 sq. ft.