diff --git a/config/config.go b/config/config.go
index b36871c52..0222b000f 100644
--- a/config/config.go
+++ b/config/config.go
@@ -3,6 +3,7 @@
 package config
 
 import (
+	"net"
 	"os"
 
 	"github.com/mholt/caddy/middleware"
@@ -12,13 +13,16 @@ const (
 	defaultHost = "localhost"
 	defaultPort = "8080"
 	defaultRoot = "."
+
+	// The default configuration file to load if none is specified
+	DefaultConfigFile = "Caddyfile"
 )
 
 // config represents a server configuration. It
 // is populated by parsing a config file (via the
 // Load function).
 type Config struct {
-	// The hostname or IP to which to bind the server
+	// The hostname or IP on which to serve
 	Host string
 
 	// The port to listen on
@@ -51,7 +55,7 @@ type Config struct {
 
 // Address returns the host:port of c as a string.
 func (c Config) Address() string {
-	return c.Host + ":" + c.Port
+	return net.JoinHostPort(c.Host, c.Port)
 }
 
 // TLSConfig describes how TLS should be configured and used,
diff --git a/main.go b/main.go
index e5a953c21..8ecf316e8 100644
--- a/main.go
+++ b/main.go
@@ -2,7 +2,9 @@ package main
 
 import (
 	"flag"
+	"fmt"
 	"log"
+	"net"
 	"sync"
 
 	"github.com/mholt/caddy/config"
@@ -15,7 +17,7 @@ var (
 )
 
 func init() {
-	flag.StringVar(&conf, "conf", server.DefaultConfigFile, "the configuration file to use")
+	flag.StringVar(&conf, "conf", config.DefaultConfigFile, "the configuration file to use")
 	flag.BoolVar(&http2, "http2", true, "enable HTTP/2 support") // temporary flag until http2 merged into std lib
 }
 
@@ -24,17 +26,25 @@ func main() {
 
 	flag.Parse()
 
-	vhosts, err := config.Load(conf)
+	// Load config from file
+	allConfigs, err := config.Load(conf)
 	if err != nil {
 		if config.IsNotFound(err) {
-			vhosts = config.Default()
+			allConfigs = config.Default()
 		} else {
 			log.Fatal(err)
 		}
 	}
 
-	for _, conf := range vhosts {
-		s, err := server.New(conf)
+	// Group by address (virtual hosting)
+	addresses, err := arrangeBindings(allConfigs)
+	if err != nil {
+		log.Fatal(err)
+	}
+
+	// Start each server with its one or more configurations
+	for addr, configs := range addresses {
+		s, err := server.New(addr, configs, configs[0].TLS.Enabled)
 		if err != nil {
 			log.Fatal(err)
 		}
@@ -51,3 +61,41 @@ func main() {
 
 	wg.Wait()
 }
+
+// arrangeBindings groups configurations by their bind address. For example,
+// a server that should listen on localhost and another on 127.0.0.1 will
+// be grouped into the same address: 127.0.0.1. It will return an error
+// if the address lookup fails or if a TLS listener is configured on the
+// same address as a plaintext HTTP listener.
+func arrangeBindings(allConfigs []config.Config) (map[string][]config.Config, error) {
+	addresses := make(map[string][]config.Config)
+
+	// Group configs by bind address
+	for _, conf := range allConfigs {
+		addr, err := net.ResolveTCPAddr("tcp", conf.Address())
+		if err != nil {
+			return addresses, err
+		}
+		addresses[addr.String()] = append(addresses[addr.String()], conf)
+	}
+
+	// Don't allow HTTP and HTTPS to be served on the same address
+	for _, configs := range addresses {
+		isTLS := configs[0].TLS.Enabled
+		for _, config := range configs {
+			if config.TLS.Enabled != isTLS {
+				thisConfigProto, otherConfigProto := "HTTP", "HTTP"
+				if config.TLS.Enabled {
+					thisConfigProto = "HTTPS"
+				}
+				if configs[0].TLS.Enabled {
+					otherConfigProto = "HTTPS"
+				}
+				return addresses, fmt.Errorf("Configuration error: Cannot multiplex %s (%s) and %s (%s) on same address",
+					configs[0].Address(), otherConfigProto, config.Address(), thisConfigProto)
+			}
+		}
+	}
+
+	return addresses, nil
+}
diff --git a/server/server.go b/server/server.go
index d44bc56d8..cde3d1821 100644
--- a/server/server.go
+++ b/server/server.go
@@ -4,9 +4,10 @@
 package server
 
 import (
-	"errors"
+	"crypto/tls"
 	"fmt"
 	"log"
+	"net"
 	"net/http"
 	"os"
 	"os/signal"
@@ -14,73 +15,55 @@ import (
 
 	"github.com/bradfitz/http2"
 	"github.com/mholt/caddy/config"
-	"github.com/mholt/caddy/middleware"
 )
 
-// The default configuration file to load if none is specified
-const DefaultConfigFile = "Caddyfile"
-
-// servers maintains a registry of running servers, keyed by address.
-var servers = make(map[string]*Server)
-
 // Server represents an instance of a server, which serves
 // static content at a particular address (host and port).
 type Server struct {
-	HTTP2      bool // temporary while http2 is not in std lib (TODO: remove flag when part of std lib)
-	config     config.Config
-	fileServer middleware.Handler
-	stack      middleware.Handler
+	HTTP2   bool // temporary while http2 is not in std lib (TODO: remove flag when part of std lib)
+	address string
+	tls     bool
+	vhosts  map[string]virtualHost
 }
 
-// New creates a new Server and registers it with the list
-// of servers created. Each server must have a unique host:port
-// combination. This function does not start serving.
-func New(conf config.Config) (*Server, error) {
-	addr := conf.Address()
-
-	// Unique address check
-	if _, exists := servers[addr]; exists {
-		return nil, errors.New("Address " + addr + " is already in use")
+// New creates a new Server which will bind to addr and serve
+// the sites/hosts configured in configs. This function does
+// not start serving.
+func New(addr string, configs []config.Config, tls bool) (*Server, error) {
+	s := &Server{
+		address: addr,
+		tls:     tls,
+		vhosts:  make(map[string]virtualHost),
 	}
 
-	// Use all CPUs (if needed) by default
-	if conf.MaxCPU == 0 {
-		conf.MaxCPU = runtime.NumCPU()
+	for _, conf := range configs {
+		if _, exists := s.vhosts[conf.Host]; exists {
+			return nil, fmt.Errorf("Cannot serve %s - host already defined for address %s", conf.Address(), s.address)
+		}
+
+		// Use all CPUs (if needed) by default
+		if conf.MaxCPU == 0 {
+			conf.MaxCPU = runtime.NumCPU()
+		}
+
+		vh := virtualHost{config: conf}
+
+		// Build middleware stack
+		err := vh.buildStack()
+		if err != nil {
+			return nil, err
+		}
+
+		s.vhosts[conf.Host] = vh
 	}
 
-	// Initialize
-	s := new(Server)
-	s.config = conf
-
-	// Register the server
-	servers[addr] = s
-
 	return s, nil
 }
 
 // Serve starts the server. It blocks until the server quits.
 func (s *Server) Serve() error {
-	// Execute startup functions
-	for _, start := range s.config.Startup {
-		err := start()
-		if err != nil {
-			return err
-		}
-	}
-
-	// Build middleware stack
-	err := s.buildStack()
-	if err != nil {
-		return err
-	}
-
-	// Use highest procs value across all configurations
-	if s.config.MaxCPU > 0 && s.config.MaxCPU > runtime.GOMAXPROCS(0) {
-		runtime.GOMAXPROCS(s.config.MaxCPU)
-	}
-
 	server := &http.Server{
-		Addr:    s.config.Address(),
+		Addr:    s.address,
 		Handler: s,
 	}
 
@@ -89,28 +72,91 @@ func (s *Server) Serve() error {
 		http2.ConfigureServer(server, nil)
 	}
 
-	// Execute shutdown commands on exit
-	go func() {
-		interrupt := make(chan os.Signal, 1)
-		signal.Notify(interrupt, os.Interrupt, os.Kill) // TODO: syscall.SIGQUIT? (Ctrl+\, Unix-only)
-		<-interrupt
-		for _, shutdownFunc := range s.config.Shutdown {
-			err := shutdownFunc()
+	for _, vh := range s.vhosts {
+		// Execute startup functions
+		for _, start := range vh.config.Startup {
+			err := start()
 			if err != nil {
-				log.Fatal(err)
+				return err
 			}
 		}
-		os.Exit(0)
-	}()
 
-	if s.config.TLS.Enabled {
-		return server.ListenAndServeTLS(s.config.TLS.Certificate, s.config.TLS.Key)
+		// Use highest procs value across all configurations
+		if vh.config.MaxCPU > 0 && vh.config.MaxCPU > runtime.GOMAXPROCS(0) {
+			runtime.GOMAXPROCS(vh.config.MaxCPU)
+		}
+
+		if len(vh.config.Shutdown) > 0 {
+			// Execute shutdown commands on exit
+			go func() {
+				interrupt := make(chan os.Signal, 1)
+				signal.Notify(interrupt, os.Interrupt, os.Kill) // TODO: syscall.SIGQUIT? (Ctrl+\, Unix-only)
+				<-interrupt
+				for _, shutdownFunc := range vh.config.Shutdown {
+					err := shutdownFunc()
+					if err != nil {
+						log.Fatal(err)
+					}
+				}
+				os.Exit(0)
+			}()
+		}
+	}
+
+	if s.tls {
+		var tlsConfigs []config.TLSConfig
+		for _, vh := range s.vhosts {
+			tlsConfigs = append(tlsConfigs, vh.config.TLS)
+		}
+		return ListenAndServeTLSWithSNI(server, tlsConfigs)
 	} else {
 		return server.ListenAndServe()
 	}
 }
 
-// ServeHTTP is the entry point for every request to s.
+// ListenAndServeTLSWithSNI serves TLS with Server Name Indication (SNI) support, which allows
+// multiple sites (different hostnames) to be served from the same address. This method is
+// adapted directly from the std lib's net/http ListenAndServeTLS function, which was
+// written by the Go Authors. It has been modified to support multiple certificate/key pairs.
+func ListenAndServeTLSWithSNI(srv *http.Server, tlsConfigs []config.TLSConfig) error {
+	addr := srv.Addr
+	if addr == "" {
+		addr = ":https"
+	}
+
+	config := new(tls.Config)
+	if srv.TLSConfig != nil {
+		*config = *srv.TLSConfig
+	}
+	if config.NextProtos == nil {
+		config.NextProtos = []string{"http/1.1"}
+	}
+
+	// Here we diverge from the stdlib a bit by loading multiple certs/key pairs
+	// then we map the server names to their certs
+	var err error
+	config.Certificates = make([]tls.Certificate, len(tlsConfigs))
+	for i, tlsConfig := range tlsConfigs {
+		config.Certificates[i], err = tls.LoadX509KeyPair(tlsConfig.Certificate, tlsConfig.Key)
+		if err != nil {
+			return err
+		}
+	}
+	config.BuildNameToCertificate()
+
+	conn, err := net.Listen("tcp", addr)
+	if err != nil {
+		return err
+	}
+
+	tlsListener := tls.NewListener(conn, config)
+	return srv.Serve(tlsListener)
+}
+
+// ServeHTTP is the entry point for every request to the address that s
+// is bound to. It acts as a multiplexer for the requests hostname as
+// defined in the Host header so that the correct virtualhost
+// (configuration and middleware stack) will handle the request.
 func (s *Server) ServeHTTP(w http.ResponseWriter, r *http.Request) {
 	defer func() {
 		// In case the user doesn't enable error middleware, we still
@@ -121,35 +167,21 @@ func (s *Server) ServeHTTP(w http.ResponseWriter, r *http.Request) {
 		}
 	}()
 
-	status, _ := s.stack.ServeHTTP(w, r)
+	host, _, err := net.SplitHostPort(r.Host)
+	if err != nil {
+		host = r.Host // oh well
+	}
 
-	// Fallback error response in case error handling wasn't chained in
-	if status >= 400 {
-		w.WriteHeader(status)
-		fmt.Fprintf(w, "%d %s", status, http.StatusText(status))
-	}
-}
-
-// buildStack builds the server's middleware stack based
-// on its config. This method should be called last before
-// ListenAndServe begins.
-func (s *Server) buildStack() error {
-	s.fileServer = FileServer(http.Dir(s.config.Root), []string{s.config.ConfigFile})
-
-	// TODO: We only compile middleware for the "/" scope.
-	// Partial support for multiple location contexts already
-	// exists at the parser and config levels, but until full
-	// support is implemented, this is all we do right here.
-	s.compile(s.config.Middleware["/"])
-
-	return nil
-}
-
-// compile is an elegant alternative to nesting middleware function
-// calls like handler1(handler2(handler3(finalHandler))).
-func (s *Server) compile(layers []middleware.Middleware) {
-	s.stack = s.fileServer // core app layer
-	for i := len(layers) - 1; i >= 0; i-- {
-		s.stack = layers[i](s.stack)
+	if vh, ok := s.vhosts[host]; ok {
+		status, _ := vh.stack.ServeHTTP(w, r)
+
+		// Fallback error response in case error handling wasn't chained in
+		if status >= 400 {
+			w.WriteHeader(status)
+			fmt.Fprintf(w, "%d %s", status, http.StatusText(status))
+		}
+	} else {
+		w.WriteHeader(http.StatusNotFound)
+		fmt.Fprintf(w, "No such host at %s", s.address)
 	}
 }
diff --git a/server/virtualhost.go b/server/virtualhost.go
new file mode 100644
index 000000000..57c5651cb
--- /dev/null
+++ b/server/virtualhost.go
@@ -0,0 +1,42 @@
+package server
+
+import (
+	"net/http"
+
+	"github.com/mholt/caddy/config"
+	"github.com/mholt/caddy/middleware"
+)
+
+// virtualHost represents a virtual host/server. While a Server
+// is what actually binds to the address, a user may want to serve
+// multiple sites on a single address, and what is what a
+// virtualHost allows us to do.
+type virtualHost struct {
+	config     config.Config
+	fileServer middleware.Handler
+	stack      middleware.Handler
+}
+
+// buildStack builds the server's middleware stack based
+// on its config. This method should be called last before
+// ListenAndServe begins.
+func (vh *virtualHost) buildStack() error {
+	vh.fileServer = FileServer(http.Dir(vh.config.Root), []string{vh.config.ConfigFile})
+
+	// TODO: We only compile middleware for the "/" scope.
+	// Partial support for multiple location contexts already
+	// exists at the parser and config levels, but until full
+	// support is implemented, this is all we do right here.
+	vh.compile(vh.config.Middleware["/"])
+
+	return nil
+}
+
+// compile is an elegant alternative to nesting middleware function
+// calls like handler1(handler2(handler3(finalHandler))).
+func (vh *virtualHost) compile(layers []middleware.Middleware) {
+	vh.stack = vh.fileServer // core app layer
+	for i := len(layers) - 1; i >= 0; i-- {
+		vh.stack = layers[i](vh.stack)
+	}
+}