WINTER GARDEN
Winter Garden is a charming and vibrant city known for its rich history and small-town atmosphere. Its historic downtown area, with brick-lined streets and preserved architecture, exudes a nostalgic charm.
MARKET SNAPSHOT FOR WINTER GARDEN
(MAY 11, 2026 - JUN 10, 2026)
MARKET SNAPSHOT FOR WINTER GARDEN
559 Properties for Sale In Winter Garden
- Newest Listings
- Default
- Baths (Most)
- Beds (Most)
- Square Feet (Biggest)
- Price-High To Low
- Price-Low To High
- 1/40 40
New$499,999
3 Beds2 Baths1,692 SqFt17035 HARBOR OAK Pkwy, Winter Garden, FL 34787
Single Family Home
Listed by Heidi Pfeffer-Morgan DALTON WADE INC
- 3D
New$929,000
5 Beds5 Baths4,495 SqFt3362 HANGING TIDE ST, Winter Garden, FL 34787
Single Family Home
Listed by Drew Belani COMPASS FLORIDA LLC
- 1/39 39
New$425,000
3 Beds2 Baths1,616 SqFt420 E CYPRESS ST, Winter Garden, FL 34787
Single Family Home
Listed by Trevor Zwick KELLER WILLIAMS ELITE PARTNERS III REALTY
- 3D
New$1,200,000
4 Beds3 Baths3,512 SqFt440 TIERRA VERDE LN, Winter Garden, FL 34787
Single Family Home
Listed by Jerry Osser CHARLES RUTENBERG REALTY ORLANDO
- 1/51 51
New$950,000
5 Beds3 Baths3,777 SqFt6100 CYPRESS HILL RD, Winter Garden, FL 34787
Single Family Home
Listed by Crystal Taylor DALTON WADE INC
- 1/74 74
New$1,300,000
4 Beds4 Baths3,424 SqFt9189 BUSACO PARK WAY, Winter Garden, FL 34787
Single Family Home
Listed by Sulamit Sanchez COLDWELL BANKER REALTY
- 1/34 34
Active$648,000
4 Beds4 Baths2,568 SqFt13843 LANYARD WAY, Winter Garden, FL 34787
Single Family Home
Listed by Jiu Wei AAA GLOBAL VENTURES PA
- 1/55 55
Active$525,000
3 Beds3 Baths2,152 SqFt2241 WHITE FEATHER LOOP, Winter Garden, FL 34787
Single Family Home
Listed by Brynn Allen CORCORAN PREMIER REALTY
- 1/47 47
Active$500,000
4 Beds2 Baths1,972 SqFt231 DOE RUN DR, Winter Garden, FL 34787
Single Family Home
Listed by Rick Coles THE C SMITH REAL ESTATE GROUP LLC
- 1/44 44
Active$700,000
5 Beds4 Baths3,532 SqFt5973 CYPRESS HILL RD, Winter Garden, FL 34787
Single Family Home
Listed by Michael Ellingson NEARBY REALTY
- 1/26 26
Active$438,890
3 Beds3 Baths1,683 SqFt6238 SUNNY TIME AVENUE, Winter Garden, FL 34787
Townhouse
Listed by Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC
- 1/65 65
Active$600,000
5 Beds3 Baths2,940 SqFt181 ZACHARY WADE ST, Winter Garden, FL 34787
Single Family Home
Listed by Ashley Boyd BHHS FLORIDA REALTY
- 1/33 33
Active$379,900
3 Beds3 Baths1,620 SqFt2120 GOPHER TORTOISE TER, Winter Garden, FL 34787
Townhouse
Listed by Andy Neal THE AGENCY FL
- 1/24 24
Active$424,490
3 Beds3 Baths1,553 SqFt6246 SUNNY TIME AVENUE, Winter Garden, FL 34787
Townhouse
Listed by Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC
- 1/34 34
Active$649,990
4 Beds3 Baths2,136 SqFt11036 ROBERT FROST DR, Winter Garden, FL 34787
Single Family Home
Listed by Rodrigo Khoury Francisco WRA BUSINESS & REAL ESTATE
- 1/87 87
Active$1,100,000
5 Beds4 Baths3,894 SqFt13181 TOOLCROSS WAY, Winter Garden, FL 34787
Single Family Home
Listed by Roberta do Nascimento Ferreira Voto FLORIDA CONNEXION PROPERTIES
- 1/37 37
Active$1,000,000
4 Beds4 Baths3,828 SqFt13822 JOMATT LOOP, Winter Garden, FL 34787
Single Family Home
Listed by Jenna Palmero COLDWELL BANKER REALTY
- 1/57 57
Open Wed 2PM-4PM$885,000
5 Beds4 Baths3,687 SqFt13978 LANYARD WAY, Winter Garden, FL 34787
Single Family Home
Listed by Selby Turnbull EXP REALTY LLC
- 1/68 68
Active$730,000
5 Beds4 Baths2,896 SqFt15591 GENTLE RAIN DR, Winter Garden, FL 34787
Single Family Home
Listed by Carolina Fortes Ribeiro EMPIRE NETWORK REALTY
- 1/38 38
Active$668,000
4 Beds5 Baths2,930 SqFt16277 HONEY HARVEST ST, Winter Garden, FL 34787
Single Family Home
Listed by Jennifer Olmeda WRA BUSINESS & REAL ESTATE
- 1/35 35
Open Sat 11AM-2PM$599,000
3 Beds3 Baths2,435 SqFt279 DOE RUN DR, Winter Garden, FL 34787
Single Family Home
Listed by Jerry Cionci FLORIDA EXECUTIVE REALTY 2
- 1/28 28
Active$546,490
3 Beds3 Baths1,913 SqFt6279 SUNNY TIME AVENUE, Winter Garden, FL 34787
Single Family Home
Listed by Adrienne Escott PULTE REALTY OF NORTH FLORIDA LLC
- 1/57 57
Active$639,000
4 Beds3 Baths2,274 SqFt8266 PURPLE SANDPIPER AVE, Winter Garden, FL 34787
Single Family Home
Listed by Thomas Nickley, Jr KELLER WILLIAMS REALTY AT THE PARKS
- 1/23 23
Active$530,000
3 Beds3 Baths2,078 SqFt10301 AUSTRINA OAK LOOP, Winter Garden, FL 34787
Single Family Home
Listed by Rick Gradin OKKLA REALTY
