2,010 properties for sale in Gladstone, Chicago city Cook County Illinois

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Welcome to this beautifully renovated and thoughtfully expanded bungalow, perfectly situated on a quiet, tree-lined street in the highly desirable Norwood Park/Jefferson Park neighborhood near Edgebrook Woods. Designed for today's lifestyle, this home offers 3 bedrooms plus a dedicated office, 2.5 bathrooms, an inviting open-concept main level, and a finished walk-out basement. Completely renovated in 2020, this sun-filled home features spacious living and dining areas that flow seamlessly into the kitchen, complete with stainless steel appliances, abundant cabinetry, generous prep space, and an adjacent mudroom. The main level also includes a bedroom and a dedicated office nook with a stylish wine bar, adding both function and character while creating the perfect setting for everyday living and effortless entertaining. Upstairs, you'll find two generously sized bedrooms, each with charming reading nooks, along with a spa-inspired bathroom featuring a double vanity and ample storage. T

Rare opportunity to own a beautifully maintained two-flat in the heart of Gladstone Park! Owned by the same family for over 60 years, this pride-of-ownership property combines classic Chicago charm with numerous updates and strong income potential. Property being sold as-as. Both units have been thoughtfully refreshed, making this a truly turnkey opportunity for investors and owner-occupants alike. Major improvements include newer windows, roof, siding, gutters, downspouts, furnace, central air, updated kitchens, and recent interior paint. The second-floor unit was extensively updated in 2022 with new flooring, cabinetry, carpeting, and fresh paint, while the first-floor unit was repainted in 2025. The property features two well maintained units with tenants already in place, providing immediate rental income from day one. Both leases are currently month-to-month, offering future owners flexibility while benefiting from an established income stream. The first-floor unit has use of a fi

Fantastic investment opportunity in the desirable Jefferson Park neighborhood-a well-maintained and updated 2-flat that offers both turnkey investment potential and the option for owner-occupancy. Each unit features 2 bedrooms and 1 bathroom, complemented by beautiful hardwood floors, central HVAC, and a bonus back porch. The main floor unit boasts modern upgrades, including stainless steel appliances, maple cabinetry, and new light fixtures. Both units have separate utilities, ensuring convenience and privacy. The unfinished lower level provides dedicated laundry spaces, mechanical systems, and open storage for each unit. Additionally, there is a detached 2.5 garage currently leased to a neighbor, adding extra income potential. Situated on a quiet, tree-lined street, this property is within walking distance to the Gladstone Park Metra station, offers quick highway access, and is close to schools, parks, restaurants, and shopping. Current tenant leases expire in December 2026 and June

Welcome to this beautifully renovated and thoughtfully expanded bungalow, perfectly situated on a quiet, tree-lined street in the highly desirable Norwood Park/Jefferson Park neighborhood near Edgebrook Woods. Designed for today's lifestyle, this home offers 3 bedrooms plus a dedicated office, 2.5 bathrooms, an inviting open-concept main level, and a finished walk-out basement. Completely renovated in 2020, this sun-filled home features spacious living and dining areas that flow seamlessly into the kitchen, complete with stainless steel appliances, abundant cabinetry, generous prep space, and an adjacent mudroom. The main level also includes a bedroom and a dedicated office nook with a stylish wine bar, adding both function and character while creating the perfect setting for everyday living and effortless entertaining. Upstairs, you'll find two generously sized bedrooms, each with charming reading nooks, along with a spa-inspired bathroom featuring a double vanity and ample storage. T

Nice jefferson park 2 flat with finished basement! 2 oversize units with central air, three separate furnaces and hot water tanks, copper plumbing. Both units have formal dining room, den and sliding door to the deck! Newer widows, newer 1st floor ac unit, two furnaces and water tanks are newer too. 2 car garage and additional parking spot. Coin laundry. Great res block! The property is in a great shape but seller wants to sell it as is

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank