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3 beds New construction With a pool

5 Bedroom Homes in Winter Garden, FL

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24 of 125 Listings

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24 of 125 Listings

Price ReducedOpen house Sat, Oct 31 · 11:00 AM46

5 Bedroom Homes in Winter Garden, FL — Page 5

125 listings

5 Bedroom Homes in Winter Garden, FL

Hide Map

24 of 125 Listings

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5 Bedroom Homes in Winter Garden, FL

24 of 125 Listings

Your Winter Garden agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

Price ReducedOpen house Sat, Oct 31 · 11:00 AM46

Your Winter Garden agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

Active

$835,000

5 bd · 4 ba · 3,538 sqft

13856 Glynshel Dr, Winter Garden, FL

Mary Dees · CHOICEPOINTE REALTY, INC.

Price ReducedOpen house Sat, Oct 31 · 12:00 AM45Active

$798,777

5 bd · 5 ba · 3,657 sqft

15652 Gentle Rain Dr, Winter Garden, FL

Susana Wight · REAL BROKER, LLC

Price Reduced44Active

$689,900

5 bd · 4 ba · 3,532 sqft

5973 Cypress Hill Rd, Winter Garden, FL

Michael Ellingson · NEARBY REALTY

Your Winter Garden agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

Price Reduced68Active

$649,900

5 bd · 4 ba · 2,896 sqft

15591 Gentle Rain Dr, Winter Garden, FL

Carolina Fortes Ribeiro · EMPIRE NETWORK REALTY

Price Reduced58Active

$879,900

5 bd · 4 ba · 3,687 sqft

13978 Lanyard Way, Winter Garden, FL

Selby Turnbull · EXP REALTY LLC

Price Reduced65Active

$879,000

5 bd · 4 ba · 4,293 sqft

3286 Mainsail Ct, Winter Garden, FL

Cora Johnson · WYNNMORE REALTY LLC

25Active

$825,000

5 bd · 4 ba · 3,812 sqft

13613 Larsen Ln, Winter Garden, FL

Theresa Choo Sau, PA · CENTURY 21 CARIOTI

96Active

$1,600,000

5 bd · 5 ba · 4,442 sqft

325 Crystal Wood Dr, Winter Garden, FL

Daniel Pavel · WRA BUSINESS & REAL ESTATE

Price Reduced77Active

$1,999,000

5 bd · 5 ba · 4,661 sqft

9110 Morgana Ct, Winter Garden, FL

Alie Gattis · MAINFRAME REAL ESTATE

Open house Mon, Oct 26 · 10:00 AM53Active

$781,000

5 bd · 4 ba · 2,670 sqft

17422 Honeybell Tangelo Ct, Winter Garden, FL

Abigail Belchick · OLYMPUS EXECUTIVE REALTY INC

Price Reduced14Active

$899,900

5 bd · 4 ba · 4,305 sqft

10103 Austrina Oak Loop, Winter Garden, FL

Wendy Wu · AMERICA REAL ESTATE COMPANY LL

78Active

$1,675,000

5 bd · 4 ba · 4,473 sqft

279 Zachary Wade St, Winter Garden, FL

Andrew Philippone · INDEPENDENCE REALTY GROUP LLC

77Active

$3,799,000

5 bd · 6 ba · 5,450 sqft

13542 Sunset Lakes Cir, Winter Garden, FL

Julie Bettosini, PA · STOCKWORTH REALTY GROUP

69Active

$1,575,900

5 bd · 6 ba · 4,977 sqft

17372 Glossy Pomelo Way, Winter Garden, FL

Francisco Tatagiba Junior · WRA BUSINESS & REAL ESTATE

Price Reduced42Active

$943,000

5 bd · 5 ba · 3,461 sqft

5150 Citrus Leaf Blvd, Winter Garden, FL

Natalia Romanelli Mourao · MS LAND & BUILDING LLC

Price Reduced47Active

$1,000,000

5 bd · 4 ba · 3,998 sqft

3208 Sailing Pier Ave, Winter Garden, FL

Karan Wienker · COLDWELL BANKER REALTY

Price Reduced45Active

$820,000

5 bd · 3 ba · 3,570 sqft

12513 Scarlett Sage Ct, Winter Garden, FL

Noah Araujo · KARDOSH REALTY

Price Reduced47Active

$1,065,000

5 bd · 5 ba · 3,816 sqft

15161 Canoe Pl, Winter Garden, FL

Maqueli Gewehr · WRA BUSINESS & REAL ESTATE

Price Reduced70Active

$819,000

5 bd · 5 ba · 3,640 sqft

15518 Honey Mandarin Way, Winter Garden, FL

Alexandre Zapparoli LLC · WRA BUSINESS & REAL ESTATE

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

$2,100,000

5 bd · 5 ba · 4,072 sqft

7701 Summerlake Pointe Blvd, Winter Garden, FL

Vanessa Ferreira · WRA BUSINESS & REAL ESTATE

Price Reduced27Active

$1,220,000

5 bd · 4 ba · 3,097 sqft

243 Zachary Wade St, Winter Garden, FL

Heather Spirazza · REGENCY REAL ESTATE LLC

Price Reduced61Active

$1,499,990

5 bd · 5 ba · 4,365 sqft

2450 Dahlgren Way, Winter Garden, FL

Trinh Minh Anh Nguyen · LPT REALTY, LLC

Price Reduced31Active

$735,000

5 bd · 4 ba · 2,878 sqft

14345 Wabasso Loop, Winter Garden, FL

Hilary Hall · COMPASS FLORIDA LLC

1…4 5 6

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 housing market

September 2026

Selling at 98.3% of asking price

Buyers here are paying below asking. MLS · 216 sales · as of Sep 30, 2026

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

Median sale price: $635,000$488,300–$925,000 typical range
Price per sq. ft.: $256
Sales: 265
Paid in cash: 36.2%

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

Median list price: $565,000

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

Explore Winter Garden homes

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Homes Under $200K
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By bedrooms

2 Bedroom Homes
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By feature

New Construction Homes
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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.

Your Winter Garden agent

Veronica Figueroa

The Figueroa Team LLC. eXp Realty, LLC

Call Veronica

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

Selling at 98.3% of asking price

Buyers here are paying below asking. MLS · 216 sales · as of Sep 30, 2026

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

Median sale price: $635,000$488,300–$925,000 typical range
Price per sq. ft.: $256
Sales: 265
Paid in cash: 36.2%

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

35 days

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

Year-over-year: 11.8%

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

Median home size: 2,211 sq. ft.