Old Town Homes under $500,000

Spacious Top-Floor Corner Unit with High Ceilings & Rooftop Access Extra-wide 2 bed, 2 bath penthouse in an elevator building (approx. 1,300 sq ft). Bright, open layout with hardwood floors, gas fireplace, and private balcony. Rare direct rooftop deck access just one flight up-600+ sq ft shared space with skyline views, fire table, seating, and grill. Attached heated garage included! Kitchen:

Lillian Baldwin Real Broker, LLC

Bright and beautifully renovated 2-bedroom, 2-bath corner unit in a prime Gold Coast/Old Town location, offering sweeping lake and city views from nearly every room. This high-floor home features a large private balcony, perfect for soaking in sunrises or entertaining against a stunning skyline backdrop. A full renovation in 2014 brought modern style to the entire space, including wide-plank

Grigory Pekarsky Vesta Preferred LLC

One of the largest two-bedroom floor plans in the building, this impeccably updated residence offers sophisticated urban living in the heart of Old Town with new paint and new carpet in the bedrooms. The kitchen is beautifully appointed with quartz countertops, a sleek backsplash, an under mounted stainless steel sink, and stainless steel appliances, all framed by elegant 42-inch maple cabinetry.

Rachel Vecchio Baird & Warner

This beautifully renovated 2-bedroom, 1-bath condo offers a rare opportunity to live in the highly sought-after Gold Coast, with breathtaking east-facing views of Lake Michigan and the downtown skyline. Recently gutted and thoughtfully rehabbed, this home features wide-plank natural wood floors, top-of-the-line finishes, and an expansive private balcony perfect for enjoying the incredible views.

Danielle Dowell Berkshire Hathaway HomeServices Chicago

Spacious 2bed/2bath with in-unit washer/dryer and a balcony! This northwest corner unit in the sought after James House building in Sandburg Terrace is move in ready. The spacious main living room has park and lake views and a west facing balcony, perfect for those incredible sunsets. Updated kitchen with stainless steel appliances and granite countertops. Split bedroom floorplan. Master bedroom

Kimberly Saydak Baird & Warner

Presenting this rarely available spectacular newly gut rehabbed two bedroom unit with balcony on the much sought after east facing side of James House with lake views. Be the first to live in this beautiful unit, among the many new features are the in-unit washer & dryer. The entire unit was gut-renovated and finished to the highest standards. The large kitchen has contemporary gloss white

Eamonn Stafford @properties Christie's International Real Estate

Stunning newly gut rehabbed two bedroom unit at James House, with large balcony on a high floor with panoramic views of the city and skyline. Be the first to live in this unit, among the many new features is the in-unit washer & dryer. The entire unit was renovated and finished to the highest standards. The beautiful open kitchen has contemporary gloss white cabinets with black accent hardware

Eamonn Stafford @properties Christie's International Real Estate

Absolutely stunning renovation from experienced condo renovation team BW Designs. Experience a completely updated layout and all new luxe finishes throughout this perfect floorplan PLUS an IN-UNIT Washer/ Dryer. Split bedrooms, transformed bath, and an open kitchen and spacious living room. Beautiful bespoke details including black and gold knurled door hardware, high end quartz selections, all

Shayne Wulbert @properties Christie's International Real Estate

Penthouse Vibes, Prime Location, Showroom Style - Welcome to the James House! Perched high on the 40th floor of the iconic James House in Sandburg Village, this fully renovated 2-bedroom, 1-bath condo isn't just a home-it's a statement. With designer finishes, jaw-dropping sunset and skyline views, and every imaginable upgrade already done for you, this home delivers the rare combination of

Mark Miles Spot Real Estate

A very impressive brand new corner balcony, two bedroom unit with stunning finishes throughout - Be the first to live in this gut renovated unit ideally located between Old Town & Gold Coast. This unit has wrap around windows with south and west exposures that provide abundant natural light with serene courtyard & skyline views (windows are upgraded double-pane) Enjoy the view with a lake breeze

Eamonn Stafford @properties Christie's International Real Estate

Presenting this stunning brand new penthouse unit in Bryant House with spectacular views- Be the first to live in this gut renovated two bedroom, one bathroom unit, ideally located between Old Town & Gold Coast. Wraparound windows facing South to the Chicago skyline and west with panoramic views over the city, provide abundant natural light for a bright and open space. The unit has been

Eamonn Stafford @properties Christie's International Real Estate

Stunning High-Floor Condo in a Prime Lincoln Park Location Experience breathtaking views and modern upgrades in this beautifully updated 1-bedroom + office area condo, perfectly situated in a popular dog-friendly building at Clark & Armitage. Enjoy an oversized recessed balcony, ideal for grilling, unwinding, and taking in both Lake Michigan sunrises and stunning western sunsets. The

Maureen Burns @properties Christie's International Real Estate

Huge price change--only asking a little over $300/FT! WALL COULD EASILY BE PUT BACK UP ON "FAMILY ROOM" TO BRING 3RD BEDROOM BACK)**VERY RARE OPPORTUNITY--THIS WAS ORIGINALLY A 2 BEDROOM CONDO & A STUDIO CONDO (CURRENTLY 2 SEPARATE TAX IDS/PINS)-- COMBINED INTO A MASSIVE 2 BEDROOM + OFFICE NOOK, 2 BATHROOM, NORTH/WEST CORNER HOME WITH 2 LARGE BALCONIES (1 BIG BALCONY OFF LIVING/DINING & 1 BIG

Kerri Hallden @properties Christie's International Real Estate

Step into luxury in this beautiful Gutt-renovated west-facing 2-bedroom, 1 bathroom residence situated at the highly desirable James House. As you enter, youll be greeted by elegant white oak wood floors that flow seamlessly throughout the living areas. The kitchen boasts high-end appliances and custom European flat panel cabinetry. Fully enclosed In-unit laundry added for your convenience.

Ryan Cherney Circle One Realty

This Southwest corner condo in Old Town offers breathtaking city views and an effortless layout. Floor-to-ceiling windows flood the space with natural light, highlighting gleaming hardwood floors. Enjoy a gas fireplace, in-unit washer/dryer, and a private balcony. The kitchen features shaker-style cabinets, stainless steel appliances, a breakfast bar, and elegant marble countertops. The primary

Nick Nastos Fulton Grace Realty