Once a bustling suburb on the city’s northern border, Lake View was annexed by Chicago in 1889. It is now the second-largest Chicago community area, with an estimated population of 102,827 people spread across dense neighborhoods such as Wrigleyville, Northalsted, and the Southport Corridor. That’s a far cry from its beginnings as a farming settlement, when immigrants from Germany and Sweden grew celery, a vegetable that could be harvested as late as January in the area’s black and boggy sandy soil. I always like to think that every old building has a story to tell, and one of our properties for sale is a rare surviving 19th-century cottage, likely a witness to that particular era of Lake View’s fascinating history. We also have a corner townhouse and a variety of condos for sale, including a duplex-down and a top-floor unit on the market for the first time in 30 years. While the number of homes sold in the area is down compared to the same time last year, median sale price per square foot rose 11.2% and overall home prices are up 3.3%, according to Redfin’s housing market trends. 

3744 N. Bosworth Avenue, $1,550,000

Photography by Baird & Warner Image Services

This 3,800-square-foot, five-bedroom single-family residence is an easy walk to the popular Music Box Theatre and everything else along the Southport Corridor. The historic property, originally built in 1888, survives intact, which makes it truly remarkable considering the rampant teardowns that take place across the city, but especially in this neighborhood. How can you not love its restored wood-clapboard facade and millwork front porch, along with the lovely professionally landscaped backyard? The home is spread over three levels, which includes a grade-level basement with a family room, wet bar, and flexible spaces. 

1020 W Roscoe Street No. 1W, $739,000

Photography by Elizabeth Harper/Lady E Photography, LLC

This four-bedroom, three-bathroom duplex-down, with $540 monthly HOAs, is located in a side-by-side six-flat building in the heart of Lake View. The interior space has the feel of a single-family home. The main level features a combination living/dining/kitchen area with south-facing windows and 10-foot ceilings. Three bedrooms are on the same level, with a hallway next to the primary bedroom suite leading directly to a semi-private patio. An open staircase in the living room descends to the lower level, which includes a family room, a fourth bedroom or potential office, and bonus space.

2868 N. Orchard Street, $1,199,900

Photography by Realvision

Located just steps away from Clark Street, this 2,100-square-foot corner townhouse boasts extensive upgrades and lots of threes: three bedrooms, three full bathrooms, and three exposures. But what really makes the property distinctive, besides no monthly HOA assessments, is the number of exceptional outdoor spaces. In addition to the ground-level walled paver patio, there are two separate rooftop terraces directly accessible from the penthouse-level lofted family room. They’re equipped with a built-in television, a retractable privacy screen, a gas line, and a new irrigation system. The open floor plan, featuring a spacious kitchen, is perfect for indoor entertaining, but you can easily take the party outside.

1245 W. George Street No. 201, $750,000

Photography by FENX Studio

This three-bedroom, two-bathroom condo is on George Court, located right off Lincoln Avenue and is within walking distance of the Wellington and Diversey Brown Line stops. The 1,400-square-foot unit has a slightly angled layout upon entry, but I love its charm and coziness, especially those exposed brick walls. Although it last sold almost nine years ago, the property comes with a newer HVAC system, air conditioning condenser, and water heater. I also think the $350 monthly HOAs are a bargain, considering the building’s expansive rooftop deck with amazing skyline views.

434 W Aldine Ave, Unit 3A, $329,900

Photography by Gary Metzler, care of Realvision

In East Lake View (or is it Lake View East?), a top-floor condo with $406 monthly HOAs came onto the market last week for the first time in over 30 years. Can you imagine how much this neighborhood has changed since 1995? Well, we all know the housing prices have certainly changed, as it looks like the property last sold for $154,500. The 950-square-foot, one-bedroom, one-bathroom condo, with its south-facing windows, is like living in a treehouse. The unit also includes roof rights and two deeded parking spaces, a rare find in this part of town. While it may be on the smaller side, don’t forget that the lakefront trail and Belmont Harbor are right outside your door.