Lake County · ~30 min west of Orlando
Clermont — the Gem of the Hills
Main lake systemClermont Chain of Lakes
Known forHills, citrus & training grounds
Trails & Outdoors
- South Lake Trail — 13 paved miles hugging Lake Minneola, part of Clermont's official "Trail Town" network.
- At Killarney Station, South Lake Trail connects directly into the West Orange Trail — together with the Hancock Trail, that's over 40 connected miles running from Clermont through Winter Garden and Apopka.
- Lake Louisa State Park — 20+ miles of hiking and horseback trails, plus paved biking routes.
- Citrus Tower — a 1956 observation tower with sweeping hilltop views of the lake country.
Lakes & Water
- Clermont Chain of Lakes — 8,000+ connected acres anchored by Lake Minneola.
- Waterfront Park — swimming, fishing piers and boat ramps; home of the Great Florida Triathlon.
- Lake Louisa's three lakes — kayaking, canoeing and paddleboarding in one park.
Shopping & Dining
- Historic Downtown Clermont — walkable boutiques, breweries just two blocks apart, and a Sunday farmers market with 50+ vendors.
- Montrose Street Market — a food hall anchoring the downtown dining scene.
- Lakeridge Winery & Vineyards — Florida's largest premium winery, with free daily tastings.
Fun Facts
- "Choice of Champions" — Olympic and pro triathletes train year-round at the National Training Center.
- Clermont is named after a town in France, the birthplace of its founder.
- Unlike most of flat Florida, Clermont's rolling terrain makes it a favorite for challenging bike training.
Schools
Public
Private
- Imagine Schools at South Lake (K-8 charter)
- Lake Pointe Academy (PK-8 charter)
- Aurelia M. Cole Academy (PK-8)
Orange County · ~20 min west of Orlando
Winter Garden — the historic Trail Town
Main lakeLake Apopka
Founded1908
Winter Garden sits in Orange County, not Lake County — but it shares the same interconnected chain-of-lakes geography as its neighbors to the west, anchored here by Lake Apopka.
Trails & Outdoors
Lakes & Water
- Lake Apopka — Florida's 4th-largest lake at roughly 30,000 acres.
- Newton Park — lakefront sunsets, a boat ramp and fishing pier.
- Lake Apopka Wildlife Drive — an 11-mile self-guided route through wetlands with up to 360 bird species, otters and alligators.
Shopping & Dining
- Historic Plant Street — brick-lined downtown with the Garden Theatre and SoBo Art Gallery.
- Plant Street Market — a bustling artisan food hall.
- Winter Garden Farmers Market — held every Saturday and ranked among the best in the country.
Fun Facts
- The Downtown Interactive Fountain next to the farmers market pavilion is a favorite splash spot for kids.
- The old Tavares & Gulf depot is now the Central Florida Railroad Museum, a nod to the town's citrus-and-railroad roots.
- Friday nights bring free live concerts at the Centennial Plaza Gazebo.
Schools
Public
Private
- Foundation Academy — three campuses, PreK-12, Christian
Orange County · ~25 min from Orlando
Windermere — life on the Butler Chain
Main lake systemButler Chain of Lakes
Town Hall built1924
Windermere is also in Orange County — but its Butler Chain of Lakes is every bit the lake-country draw, just spring-fed and closer to the parks than its Lake County neighbors.
Trails & Outdoors
- Kayak and paddleboard rentals on the Butler Chain through local outfitters like Epic Paddle Adventures.
- Scenic shoreline drives past the chain's landmark homes.
- R.D. Keene Park — the only public boat ramp access to the chain.
Lakes & Water
- Butler Chain of Lakes — 13 interconnected, spring-fed lakes covering nearly 5,000 acres, linked by 32 canals.
- Known for crystal-clear water, bass fishing, wakeboarding, waterskiing and pontoon cruising.
- One of the cleanest, most sought-after lake systems in Central Florida.
Shopping & Dining
- Main Street — brick streets past the 1924 Town Hall, with shops like Pistil Home & Garden and Tim's Wine Market.
- Friday Farmers Market at Town Square Park.
- Windermere Brewing Company plus a growing lineup of new Main Street restaurants.
Fun Facts
- Several Butler Chain lakefront homes have belonged to pro athletes, including Shaquille O'Neal and Tiger Woods.
- The chain's water is spring-fed and famously clear, even by Florida lake standards.
- Windermere's Main Street Town Hall has stood since 1924.
Schools
Public
Private
- Windermere Preparatory School — PK-12 international day & boarding school
Lake County · ~10 min from Clermont
Montverde — Clermont's quiet hilltop neighbor
Main lakeLake Apopka shoreline
PopulationUnder 2,000
Trails & Outdoors
- The West Orange Trail passes directly through town, connecting Montverde to Winter Garden and Clermont on two wheels.
- Green Mountain Scenic Byway — a hilly, tree-lined drive (and ride) with some of the best views in Lake County.
- Kirk Park — tennis and basketball courts, a playground and a community stage tucked into the center of town.
Lakes & Water
- Sits directly on the shore of Lake Apopka, with quiet boating and sunset fishing spots along the way.
- Rolling hills right down to the water — a rare combination for Central Florida.
Shopping & Dining
- A true small-town main street feel, anchored by local spots like Mr. Willie's BBQ.
- Bella Collina — a gated golf and lakefront community with clubhouse dining and event space.
- Just a short drive to Lakeridge Winery in Clermont or Plant Street in Winter Garden for a bigger night out.
Fun Facts
- Home to Montverde Academy, founded in 1912 — its basketball program is nationally ranked and has sent players on to the NBA.
- Montverde sits just 10 minutes from downtown Clermont, making it one of the easiest "hidden gem" add-ons for buyers already looking there.
- One of the smallest, hilliest towns in the entire chain — quiet, rural, and still 30 minutes from Disney.
Schools
Public
- Montverde has no public campus inside town limits — families typically zone into nearby Clermont & Minneola schools
- Grassy Lake Elementary & Imagine Schools at South Lake
- East Ridge Middle & Lake Minneola High School
Private
- Montverde Academy — PK3-12, day & boarding, founded 1912
Lake County · ~35-40 min northwest of Orlando
Mount Dora — the New England of the South
Main lakeLake Dora, Harris Chain
Elevation184 ft
Trails & Outdoors
- Hiking, biking, canoeing and kayaking around the lake and nearby parks.
- Grantham Park — home to the Mount Dora Lighthouse, one of only a few freshwater lighthouses in the U.S.
- Horseback riding and wildlife viewing in the surrounding hills.
Lakes & Water
- Lake Dora — nearly 5,000 acres, part of the Harris Chain, connecting all the way to the St. Johns River.
- Pontoon tours, lake cruises and bass fishing off the marina.
- Home to the state's oldest sailboat regatta, held near the Mount Dora Yacht Club.
Shopping & Dining
- A walkable historic downtown of boutiques, antique shops and art galleries.
- Renninger's — a massive antique center and flea market on the edge of town.
- The 1883 Lakeside Inn — Florida's oldest continuously operating hotel, with lakeside dining and rocking-chair porches.
Fun Facts
- Known as "Festival City," Mount Dora hosts 30+ festivals a year, including an Arts Festival that draws nearly 200,000 visitors.
- President Calvin Coolidge vacationed at the Lakeside Inn for over a month in 1930.
- In 1981, downtown was painted pink for the movie Honky Tonk Freeway — featuring a waterskiing elephant named Bubbles.
Schools
Public
Private
- Mount Dora Christian Academy — PK2-12, founded 1945