The Dating Gazette
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Maitland

suburban office · 32751

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.

4,731
singles 22–50
58%
male
$49,781
median income
$1,995
median rent
The data

Maitland by the numbers

On the ground

Local date spots

Layton Gaming · MaitlandANTONIO'S Maitland · MaitlandFrancesco's Ristorante & Pizzeria · MaitlandLuke's Kitchen and Bar · MaitlandJazz Tastings · MaitlandSelva Rosa Cocina & Bar · MaitlandCopper Rocket · MaitlandAiguille Rock Climbing Center · MaitlandLake Fairview Park · MaitlandEden Bar · MaitlandGood Times Bar & Grill · MaitlandPermanent Vacation · MaitlandThe Haven Tabletop Games · MaitlandBrewlando Maitland · MaitlandElevate Kava Bar & Lounge · MaitlandPackwoods · MaitlandMaitland
16 spots · tap a point, label, or class to filter
Class
Budget
Vibe

16 spots across Maitland

  • Maitland
    Activity

    Layton Gaming

    Board game club4.9 · 2,618
    LGBTQ+ friendlyWheelchair access
  • Maitland
    Dining

    ANTONIO'S Maitland

    Italian restaurant$$$$4.5 · 2,102
  • Maitland
    Dining

    Francesco's Ristorante & Pizzeria

    Southern Italian restaurant$$$$4.6 · 2,100
  • Maitland
    Dining

    Luke's Kitchen and Bar

    New American restaurant$$$$4.4 · 2,060
  • Maitland
    Dining

    Jazz Tastings

    Restaurant$$$$4.6 · 1,284
  • Maitland
    Drinks

    Selva Rosa Cocina & Bar

    Bar$$$$4.8 · 1,281
  • Maitland
    Drinks

    Copper Rocket

    Sports bar$$$$4.3 · 847
  • Maitland
    Activity

    Aiguille Rock Climbing Center

    Rock climbing gym4.6 · 744
    Wheelchair access
  • Maitland
    Activity

    Lake Fairview Park

    Park4.3 · 561
    Wheelchair access
  • Maitland
    Drinks

    Eden Bar

    Bar$$$$4.7 · 539
  • Maitland
    Drinks

    Good Times Bar & Grill

    Bar$$$$4.4 · 411
  • Maitland
    Drinks

    Permanent Vacation

    Cocktail bar$$$$4.6 · 262
  • Maitland
    Activity

    The Haven Tabletop Games

    Board game club4.7 · 232
    LGBTQ+ friendlyWheelchair access
  • Maitland
    Activity

    Brewlando Maitland

    Brewery$$$$4.6 · 138
  • Maitland
    Drinks

    Elevate Kava Bar & Lounge

    Tea house$$$$4.7 · 103
  • Maitland
    Drinks

    Packwoods

    Cocktail bar$$$$4.6 · 83
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