Maitland
Maitland is Winter Park's quieter older sibling, the one who took the corporate job and the lake house. Office parks ring Maitland Boulevard, oak canopies shade the side streets, and the Maitland Art Center still pretends it's 1937. Lake Lily on a Sunday is the closest thing to a town square. The dating math is unforgiving: median age skews married-with-mortgage, and the singles here mostly commute downtown for anything resembling a scene. Bring a date here for brunch at Antonio's or a slow walk around the lake. Don't bring them expecting nightlife, or even a third bar.
Maitland by the numbers
Maitland runs male-heavy, about 58% men to 42% women.
Median individual income in Maitland is about $49,800.
Florida registers voters by party, and Orange County has stayed Democratic, about 39% Democratic to 28% Republican, with a large 30% no-party bloc.
The median renter in Maitland pays about $2,000 a month.
About 4,700 Maitland residents ages 22 to 50 are single.
Local date spots
- MaitlandActivity
Layton Gaming
LGBTQ+ friendlyWheelchair access - MaitlandDining
ANTONIO'S Maitland
- MaitlandDining
Francesco's Ristorante & Pizzeria
- MaitlandDining
Luke's Kitchen and Bar
- MaitlandDining
Jazz Tastings
- MaitlandDrinks
Selva Rosa Cocina & Bar
- MaitlandDrinks
Copper Rocket
- MaitlandActivity
Aiguille Rock Climbing Center
Wheelchair access - MaitlandActivity
Lake Fairview Park
Wheelchair access - MaitlandDrinks
Eden Bar
- MaitlandDrinks
Good Times Bar & Grill
- MaitlandDrinks
Permanent Vacation
- MaitlandActivity
The Haven Tabletop Games
LGBTQ+ friendlyWheelchair access - MaitlandActivity
Brewlando Maitland
- MaitlandDrinks
Elevate Kava Bar & Lounge
- MaitlandDrinks
Packwoods