The Area

Looking for a place that feels like home and keeps life easy? Welcome to 2238 W. Winona-a classic Chicago 2-flat where everything you need is just steps away. Here, everyday errands are a breeze, transit options are around the corner, and parks, schools, and local eats are all within reach. Whether you’re grabbing fresh groceries, hopping on the train, or meeting friends at a neighborhood festival, this is city living designed for your routine-not the other way around. Enjoy a walkable, vibrant community with room to grow, all while being minutes from the heart of the city. Discover a home that fits your lifestyle, your commute, and your weekends-no car required, no compromises needed

Essentials Within Reach

Everyday errands are effortless here:

  • Tony’s Fresh Market and HarvestTime Foods for affordable, diverse groceries

  • Gene’s Sausage Shop, a local landmark for specialty meats, European imports & its rooftop beer garden

  • Walgreens and CVS (open til midnight), both within walking distance

  • Mariano’s just a short drive or bike ride away for gourmet groceries and a wine bar

You’re never far from a fresh loaf of bread, a late-night pharmacy run, or your favorite cheese.

Easy Transit Options

Whether commuting to the Loop or heading out for the evening, your ride is close and convenient:

  • 3-minute walk to Foster & Oakley to catch the Foster bus (92) straight to the Red Line

  • 6-minute walk to Western Ave. for the Western bus (49)

  • 15-minute walk to the Western Brown Line station for a direct ride downtown

  • Biking? You’re just blocks from bike lanes on Damen, Lawrence, Winnemac and Berwyn, plus close to the North Branch Trail

  • Car-optional living at its finest.

Strong, Walkable Schools

Chappell Elementary School (just a few minutes’ walk): offers before- and aftercare, a huge help for working families

More on Chappell:

Chappell Elementary, located in Ravenswood, is a world language magnet cluster school where all students study Spanish - native speakers through a Heritage Language program and non-native students in grades 6–8 completing a first-year high school Spanish course. The school offers strong arts programming with opportunities in music, visual arts, musicals, and learning multiple instruments. Unique to Chappell are hands-on environmental education initiatives like gardening and beekeeping, supported by the Friends of Chappell School. Academically, it ranks in the top 50% statewide with particular strength in science and has earned Thrive Awards in 2021 and 2024 for its impact on student learning. Additionally, Chappell provides diverse extracurricular options, including sports, chess, garden, and computer clubs, fostering well-rounded student development. The school also offers convenient before-care starting at 7:00 AM and after-care programs, providing flexible support for working families.

Amundsen High School (just a few minutes’ walk):

  • Offers IB Diploma Programme, AP, Dual Credit, and Dyson Design & Innovation

  • 34 varsity sports + a wide range of clubs and electives

  • Ranked #6 of 62 Standout High Schools in Illinois by Niche

Parks & Playgrounds

End of the block? A green oasis.

  • Winnemac Park (22.38 acres): native prairie garden, playground, walking trails, softball & soccer fields

  • Vogle Playlot Park: a shaded, intimate playground perfect for little ones

Whether it’s a sunset stroll or Saturday soccer, there’s green space just steps from your door.

Destination Dining, Just Steps Away

Your neighborhood is a culinary hotspot:

  • Michelin-starred Atelier – bold, seasonal tasting menus

  • Gene’s Rooftop – bratwurst, beer, and skyline views

  • Garcia’s Restaurant – a local favorite for margaritas and mole

  • Willow Cafe & Bistro – the cozy new chapter of the beloved Café Selmarie

  • Plus walkable favorites like The Warbler, Bistro Campagne, and Lost Larson (2025 James Beard semi-finalist for Outstanding Bakery)

Lincoln Square is a rare mix of neighborhood warmth and culinary buzz.

Culture & Community

Lincoln Square is a hub for the arts:

  • Old Town School of Folk Music hosts live concerts, classes & jam sessions

  • The Davis Theater, a restored 1918 gem, screens everything from blockbusters to indie hits

  • Annual festivals like Apple Fest, Square Roots, and Maifest bring live music, craft beer, and neighbors together

This isn’t just a neighborhood—it’s a community with rhythm.

Architectural Charm

Your street is lined with classic Chicago brick homes, mostly owner-occupied and lovingly maintained.

  • Tree-lined Winona offers peaceful charm, yet you're only minutes from lively Lincoln Square.

  • The block has a strong sense of neighborly pride - residents know each other, shovel each other’s sidewalks, and host summer block parties and Oakley at the corner is one of the best trick or treating blocks.

A quiet block with a big heart.

Health & Wellness Nearby

Stay active and healthy with:

  • Swedish Hospital (part of Endeavor), less than 10 minutes away and includes the Galter Life Center gym.

  • Local clinics, dentists, pediatricians, and optometrists within a 5 minute drive.

  • Welles Park fitness center and pool, Pilates, and multiple yoga studios within walking distance

Wellness here is woven right into your routine.

Boutiques, Books, & Local Finds

Spend a lazy weekend browsing:

  • Merz Apothecary, an old-world pharmacy turned wellness boutique

  • Timeless Toys for award-winning kids’ gifts

  • The Book Cellar, an indie bookstore with wine & author events

  • Countless mom-and-pop shops offering everything from handmade soaps to vinyl records

Support local while finding something truly one-of-a-kind.

The Feel of a Village, Minutes from the City

2238 W. Winona sits in a unique sweet spot:

  • Peaceful, walkable, family-friendly

  • Surrounded by globally recognized restaurants, parks, and transit

  • All within 30 minutes of the Loop

It’s where city living meets neighborhood ease - quiet, connected, and full of character.