Refine Search
Sort by
1314 W Carmen Avenue, Chicago
$1,200,000
6 Beds ⋅ 2 Baths ⋅ 12737730 MLS ⋅ CONTINGENT Status
Andersonville- Most two-flats blend in, but this one breaks the mold! This classic Chicago brick 2-flat sits on an impressive 40 ft by 150 ft lot, allowing for over 3,400 sq ft of finished living space, a larger foot print than typical, a huge backyard that is a gardener's dream, and a beautiful custom bluestone patio. Both apartments are extra large with living rooms, family rooms and dining rooms as well. They both also feature private balconies. The first floor owner's unit has an internal staircase leading to the basement, providing easy access for potential duplex down conversion. The current owners have lovingly remodeled the space with attention to improvements while maintaining the original architectural details including untouched woodwork, some gas-light fixtures, speaking tubes & vintage ornate doorknobs. Most impactful is the creation of a kitchen that is straight out of a magazine and that you'd normally only see in a multi-million-dollar single family home! It boasts a custom oversized quartzite island with a cherry butcher block, a double-sized 48-inch Sub-Zero refrigerator, and a 48-inch Wolf double oven and stove top. High-end recessed lighting, in-ceiling speakers, and radiant floor heating enhance comfort during cooler months. The wall separating the kitchen and dining room was removed to create an open layout with a spacious dining room/great room area with the original built-in dining hutch still intact! The bathroom has been completely remodeled with new tile, custom quartz counters, a new triple-pane window, and a custom-built vanity. It features a walk-in shower with a bench, a custom shower door, premium fixtures, and radiant floor heating. Additional improvements include refinished walls in both apartments, new and refurbished lighting fixtures, and upgraded electrical service with two new panels (2025). The second floor has a different layout than the first with a fabulous family room adjacent to the kitchen, which has great storage and an original built-in butler's pantry. The full basement, with direct access to the first-floor apartment, offers ample storage space, a workshop area, and upgraded electrical systems, a new laundry room with beautiful tile walls, new cast-iron drains for the washer and dryer, a dog wash sink, new copper plumbing, and building-wide wired network and security cameras. Although there currently isn't parking behind the building, there are options for installing a garage, parking pad or doing a curb cut in front of the property. All this located in a spectacular Andersonville location just a couple of blocks from Clark Street with its wonderful shopping, restaurants, and bars, as well as the Red Line, and only a short distance to the lakefront and Lake Shore Drive as well. Top floor is rented for $3150 per month through the end of April 2028.

1314 W Carmen Avenue, Chicago

4725 N Kenmore Avenue, Chicago
$825,000
8 Beds ⋅ 3 Baths ⋅ 12754863 MLS ⋅ CONTINGENT Status
Rare opportunity to own a solid brick legal 3-unit building in Chicago's Uptown neighborhood on beautiful tree-lined Kenmore Avenue. Situated on an oversized lot, this Uptown multi-unit property offers outstanding potential for an investor, owner-occupant, or future single-family home conversion. Spacious units feature abundant natural light, generous room sizes, and separate living and dining spaces. Each unit has separate heating and cooling systems and individual utilities. The vacant top-floor unit features a bright 2-bedroom, 1-bath layout, dramatic stairwell accented by a skylight, and in-unit laundry. The first- and second-floor units each offer 3 bedrooms and 1 bath. The unfinished basement provides additional untapped potential with great ceiling height and two separate entrances. Detached 2-car garage. Prime Uptown Chicago location near the Wilson Red and Purple Line CTA station, multiple bus routes, lakefront parks and trails, restaurants, coffee shops, grocery stores, and the Uptown Entertainment District. An exceptional opportunity to own a brick 3-unit investment property in one of Chicago's most vibrant North Side neighborhoods.

4725 N Kenmore Avenue, Chicago

1223 W Gunnison Street, Chicago
$725,000
5 Beds ⋅ 2 Baths ⋅ 12701584 MLS ⋅ ACTIVE Status
Historic Uptown! This Chicago Classic brick two-unit offers comfortable living space for an owner-occupant or tenants! Less than 5 miles from Montrose Beach and close to restaurants and public transportation. The first-floor apartment features 2 bedrooms, 1 bathroom, and hardwood floors, while the second-floor apartment includes 3 bedrooms and 1 bathroom. Each unit includes a charming living room, a formal dining room with wood crown molding throughout, a vintage built-in hallway wood cupboard, and a back den that can be used as pleased, plus access to an unfinished basement with potential for additional storage or future improvements. The owner occupies the 1st floor unit as their primary residence and will remain until the sale closes. The 2nd floor unit is vacant. Property TUCKPOINTED 4/2022, WARRANTY ON ROOF UNTIL 5/2027, Sewer line excavated, PVC cleaned out 3/2026. Property is being sold as-is.

1223 W Gunnison Street, Chicago

1427 W Winona Street, Chicago
$1,226,000
8 Beds ⋅ 3 Baths ⋅ 12602618 MLS ⋅ CLOSED Status
Turnkey, classic Andersonville greystone offering three legal units on a wide lot. All units feature open-concept kitchens and granite baths. Bright and sunny throughout with high ceilings, hardwood floors, and gas-forced air heat. Extensive capital improvements include 2022 renovation of garden unit (new flooring, appliances, paint, etc.) New windows in 1st and 2nd floor units, refreshed common areas and 2nd floor main living spaces. The property also offers a landscaped, private fenced yard. Located on a quiet, tree-lined street just steps from Andersonville's dining and shopping district, Foster Beach, the Red Line, and Metra. Great opportunity for an investor or live-in owner in a prime location.

1427 W Winona Street, Chicago

4631 N Kenmore Avenue, Chicago
$1,430,000
11 Beds ⋅ 8 Baths ⋅ 12497672 MLS ⋅ CLOSED Status
Welcome to 4631 N. Kenmore St. an exceptional urban Oasis located within the highly desirable Uptown/Andersonville neighborhoods of Chicago. This legally classified 4 flat features spacious two-and-three - bedroom configurations each equipped with two full baths. The building classic vintage Greystone exterior, had its roof replaced in 2014, a thoughtful renovation of 1st, 2nd & 3rd floors down to the studs with a comprehensive remodeling 2015-2016. Upgrades included windows, flooring, steel porch, Tuck-pointing and coping along with the three car parking pad to enhance functionality for the residence. Garden Apt. was entirely redone in 2021. Inside each unit boasts modern kitchens features including custom 42-inch white designer cabinets, granite countertops and a breakfast bar that accommodates 4 or more making it ideal for entertaining. The kitchens are outfitted with stainless steel appliances including a dishwasher and garbage disposal, promoting both style and convenience. Each apartment also includes individually controlled central heating and air conditioning systems, oak floors, in-unit laundry facilities, and large private rear decks. Nestled along a tranquil tree lined street, the property is within proximity to a diverse selection of restaurants, cafes, parks, and public transportation options including the Wilson Red and Purple lines. Residents will also enjoy nearby attractions such as Wrigley Field, Gallagher Way, Target, Montrose beach and all the vibrant offerings of Uptown, Andersonville, Ravenswood and Lincoln square. With long-term tenants already established, this property presents an excellent opportunity for savvy investors looking to expand their portfolio in a thriving market.

4631 N Kenmore Avenue, Chicago

4870 N Magnolia Avenue, Chicago
$763,800
6 Beds ⋅ 3 Baths ⋅ 12422656 MLS ⋅ CLOSED Status
WALK THRU VIDEO ON VIRTUAL TOUR BUTTON. Legal 2 unit (not a 3 unit - BEDROOMS CAN HOLD TWIN BEDS) with 3 bedrooms top floor and a 3bed/2bth/2 kitchen duplex down (basement can be it's own unit. The basement height is 6 ft 5 at it's highest point - you take the back interior stairs to get to basement) 25 x 180 oversized lot! Rental comps around 2500 and 3500 for a total of 6k a month. 2025 renovations include nearly everything from structural, including new roof, windows, plumbing, and HVAC, to cosmetic, including drywall, insulation, floor finishes, lighting, cabinetry, appliances, and a fully finished lower level. Both units are move-in ready, ensuring a smooth transition for new tenants. The property also comes with a detached 2-car garage, storage shed, and fenced-in yard. Great uptown loaction on small 2 block run of Magnolia - close to the train, lake and shopping districts. Great rent potential and an area that is appreciating very fast. Whether you're seeking a turnkey investment or a property to live in while generating rental income, this 2-unit building presents a fantastic opportunity. - Gas Forced heat, central AC, new kitchens, Washer and Dryer on EVERY floor. HUGE backyard.

4870 N Magnolia Avenue, Chicago

1323 W Foster Avenue, Chicago
$1,230,000
5 Beds ⋅ 3 Baths ⋅ 12291540 MLS ⋅ CLOSED Status
Classic 3-unit graystone with valued, long-time tenants paying rents waaaaaay below market. *** Gut rehab in 2012 and meticulously maintained since. Rehab included new tearoff roof, deck and fence replacement, tuckpointing, all new electric and plumbing, full window replacement, new HVAC systems and full renovation of the 3 units. *** Each home has high ceilings, hardwood floors, GFA heat, central air, in-home laundry, family/sitting room and large rear deck. Units 2 & 3 also have an den/office area. *** All units have open kitchens with wood cabinetry, S/S appliances including dishwasher and stainless countertops. Baths finished with pedestal sink, tub/shower combo with subway tile, and Penny Round tile floor. *** These bright, beautiful homes overlook the stately residences of the Lakewood Balmoral Historic District. Ideally located just steps to Red Line/bus stops; Andersonville shopping, restaurants; and lakefront beaches, parks and trails. *** Top floor lease ends 4/30, so will be ready for owner-occupant; renewal of current tenants' lease; or re-lease during prime spring rental season. *** Rents INCLUDE parking + large, individual storage rooms in heated, dry, unfinished basement.

1323 W Foster Avenue, Chicago

1218 W Winona Street, Chicago
$1,007,500
4 Beds ⋅ 2 Baths ⋅ 12157223 MLS ⋅ CLOSED Status
Incredible opportunity to own a meticulously maintained Greystone rich with history and vintage charm. Situated on an extra wide double lot on one of the most desirable tree-lined streets in Uptown. Enter from your very own private side drive this special property has the most magnificent vintage detail, wood work, stained glass and period appropriate (Steuben) light fixtures. Double parlor living room, separate dining room with original built-in hutch and four generous bedrooms and two full baths. High-end eat-in chefs kitchen with stone counters, classic subway backsplash, stainless steel appliances and wood island breakfast bar. Tastefully updated bathrooms with timeless finishes - first floor features include seamless glass shower w/steam unit . Full height basement with loads of natural light offers endless possibility to expand your living space and create the home of your dreams. Separate laundry with by side washer/dryer, abundant storage and a half bath. Professionally landscaped yard, patio plus 1.5 car garage in carriage house complete with blacksmith forging station, water, and electric. Bring your ideas and convert the upstairs to a work from home office, gym or yoga studio. Additional improvements include new mini split air conditioning added to first and second floor, updated electrical and plumbing. Steps to all the best dining, shopping, entertainment and lakefront in Uptown/Andersonville neighborhood.

1218 W Winona Street, Chicago

1446 W Argyle Street, Chicago
$807,000
5 Beds ⋅ 3 Baths ⋅ 12118952 MLS ⋅ CLOSED Status
UNLOCK THE POTENTIAL - GREYSTONE & BRICK MULTI UNIT IN ANDERSONVILLE ON AN OVERSIZED LOT. One 3-bedroom /1-bath apartment, One 2 bedroom /1 bath apartment and 1bedroom /1 bath basement unit OR a blank canvas primed for conversion into your dream single-family home. Much of the original vintage detailing is intact; woodwork, moldings, and more! Detached two car garage with second floor studio. Curb cut for entrance from Argyle. Imagine the possibilities with spacious rooms, abundant natural light, and a layout tailored to your lifestyle. Whether you're looking for a renovation project, investment opportunity or a blank canvas to unleash your creativity, this property has it all. Seize this opportunity to create your ideal home.

1446 W Argyle Street, Chicago

4843 N Kenmore Avenue, Chicago
$650,000
7 Beds ⋅ 3 Baths ⋅ 12064823 MLS ⋅ CLOSED Status
Come view this spacious and sunny 2 Unit Greystone located in Uptown. This building has been well maintained by a long term live-in owner and boasts beautiful apartments on a quiet one way street. The gated entry and front yard offer plenty of curb appeal, ready for your green thumb! Hardwood floors and oversized windows throughout add to this home's charm. The 2nd floor boasts 4 bedrooms and 1.5 bathrooms, plus a washer and dryer. The 1st floor has 3 bedrooms and 1 full bath, plus a stunning brick fireplace. The prime location puts you in reach of Argyle Street, Andersonville, LUC, and Edgewater making for an easy walk for shopping, entertainment, and nightlife(such as the famous Green Mill). Multiple transportation options make for great marketability for these apartments. You won't want to miss this perfect investment opportunity!

4843 N Kenmore Avenue, Chicago

1312 W Winnemac Avenue, Chicago
$1,200,000
12 Beds ⋅ 4 Baths ⋅ 12048862 MLS ⋅ CLOSED Status
Terrific Investment Opportunity in Uptown Neighborhood! This 4-unit building presents a profitable investment opportunity with all units fully occupied. Constructed of brick and on an extra wide lot, the building boasts spacious units with central A/C and efficient gas forced air heating for tenant comfort. The garden unit has been fully renovated (2022), showcasing modern amenities and style. Stainless steel appliances are featured in all units, enhancing their appeal. Each floor offers ample storage space, ensuring convenience for tenants. Additionally, there are shared laundry facilities in the basement. Four tandem exterior spaces are available, making parking hassle-free for residents. Situated in a prime location on the cusp of Andersonville and Uptown neighborhoods. Just minutes away from restaurants, shopping, and public transportation, making it highly desirable for tenants and a promising investment opportunity for savvy investors. All lease dates ending between March-May 2025.

1312 W Winnemac Avenue, Chicago

1221 W Gunnison Street, Chicago
$795,000
4 Beds ⋅ 2 Baths ⋅ 12038371 MLS ⋅ CLOSED Status
Come see this beautiful, all-brick, Chicago 2-flat beauty. This property offers a fantastic opportunity for investors or owner occupants. Live in the whole building as current owners do, rent one unit and live in the other, or rent both. Completely renovated with new plumbing, new electrical, new roof, new bathrooms and kitchens, refinished original wood floors and moldings, and all new appliances. Washer and Dryer is common in the basement. All the historic charm with clean and modern convenience. Each unit has 2 bedrooms and 1 bathroom. Large newly fenced-in back yard and a 2-car garage. The vibrant Uptown-Andersonville area has so much to offer, from endless dining options, coffee shops, playgrounds, to multiple grocery stores. One block away from the red line and about 7 blocks away from the lake. Selling due to job relocation. Licensed broker co-owned.

1221 W Gunnison Street, Chicago

4716 N Winthrop Avenue, Chicago
$650,000
7 Beds ⋅ 4 Baths ⋅ 11927122 MLS ⋅ CLOSED Status
Location, Location, Location!!! Nestled in the Heart of Uptown Chicago! This classic red brick 3-Flat building is on an Oversized Chicago lot 33 x 142 feet, presents a Unique Opportunity for both Renovation Enthusiasts and Crafty Investors! RT-4 Zoning, whether you envision it as a Restored Religious Congregation, lovely 3 story Single Family, or an incredible rehabbed incoming generating opportunity, this uptown Gem is a Blank Canvas ready for its Next Chapter! Property is being sold "As Is". 1st and 2nd floor units features living rooms and kitchens. Hosting 2 bedrooms and 1 full bathroom in the first floor and 5 bedrooms and 1 full bathroom on the second floor. 3rd floor is very spacious open floor loft with a balcony and an additional bonus room. Full finished basement have 2 half baths, plenty storage spaces with washer and dryer. The adjacent parking lot to the building provides about 16 exterior parking spaces. Just steps away from red line public transit, just blocks away from Lake Michigan and Lake shore Drive. Walking distance to the schools, grocery stores, restaurants, and nightlife entertainment (Aragon Ballroom, the Riviera Theater and more.) This is walker's paradise. Bring your creative ideas to this Blank Canvas, full of so many potentials and enjoy all the goodness this neighborhood has to offer. PLEASE NOTE THAT THIS BUILDING HAS TO SELL WITH THE PARKING LOT LAND NEXT TO IT total of 66 x 142. (4718 N Winthrop Ave with a different price $550,000).

4716 N Winthrop Avenue, Chicago

1219 W Winnemac Avenue, Chicago
$400,000
5 Beds ⋅ 2 Baths ⋅ 11791004 MLS ⋅ CLOSED Status
Calling all investors, landlords and renovation ready owners to this classic red brick 2 flat for an incredible rehab and wealth generating opportunity in Uptown while only blocks from Andersonville. This property needs a full rehab giving a great opportunity to keep the existing configuration or convert the full unfinished basement into a garden apartment, coin operated laundry or rentable storage space. It is perfect for those looking for an owner occupied building with an Airbnb operation. The garden unit would be a perfect set up while you live in one unit and rent the other. There is also the option to easily duplex the 1st floor and basement (accessible stairs are off the dining room). Furthermore, this has the potential to be your spacious single family sanctuary. Property is being sold "As Is". Each unit features hardwood flooring, a spacious living room, separate dining room, a kitchen, hosting 3 bedrooms and 1 bathroom on the second floor and 2 bedrooms and one bathroom on the first floor. Just blocks away from Lake Michigan, located minutes away from the Cubs Stadium and Andersonville with over 85 shops, cafes and restaurants. This is a walkers paradise. Bring your creative ideas to this blank canvas and enjoy all the goodness this neighborhood has to offer.

1219 W Winnemac Avenue, Chicago



The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.

How much is your home worth?

Get instant property value now!