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1633 W Winona Street, Chicago
$1,500,000
5 Beds ⋅ 4 Baths ⋅ 12789652 MLS ⋅ ACTIVE Status
Andersonville two-flat, reimagined as a single-family home. This one was taken down to the studs in a full 2023 rehab, so the big stuff is already done for you: new electrical, plumbing and gas lines, new windows, and a roof that is just over two years old with eight years of warranty left to transfer. What makes it special is what they saved. The original vintage woodwork was restored and vintage pieces were worked back into the design, so the home has the warmth of an older house with none of the old-house problems. Six bedrooms and three and a half baths give everybody room to spread out, with real options for a home office or guests. The primary suite has its own sitting area, a walk-in closet, and a bath with heated floors, separate vanities, and a large walk-in shower. The big front bedroom also has a sitting area, plus a private balcony looking out over the tree-lined street. Laundry is on the second floor, right where the bedrooms are, and Hunter Douglas cordless top-down, bottom-up shades are installed throughout. The main level is built for having people over. The open layout runs right into an eat-in kitchen centered on an oversized quartz island, with new countertops, a convection range, and a new dishwasher added in 2026. Up top there is a rooftop deck over the detached two-car garage, and out back a landscaped yard with a black porcelain tile patio that feels like a little escape. The lower level goes even further: a roomy recreation space plus a full kitchen added in 2026, so it works as a guest suite, an in-law setup, or the spot where everybody ends up on game day. Storage in both the garage and the basement. Steps from everything happening on Clark Street, and recently featured in Crain's "Before It Hits the Market."

1633 W Winona Street, Chicago

5053 W Potomac Avenue, Chicago
$399,900
5 Beds ⋅ 3 Baths ⋅ 12789056 MLS ⋅ ACTIVE Status
Classic jumbo red brick bungalow offering 5 bedrooms, 2.5 baths, and a full second-story addition, pairing distinctive architectural character with generous space across three levels. Intricate ceiling trim gives the living and dining rooms a memorable focal point, while first-floor hardwood floors, freshly sanded and stained in light walnut, complement the home's classic appeal. The living and dining areas offer space for everyday gatherings and entertaining. In the kitchen, new stainless steel appliances include a French-door refrigerator. Updated bathrooms feature modern black fixtures. With five bedrooms, the home offers flexibility to arrange sleeping and work spaces to suit your needs. A full, partially finished basement extends the usable space, with two additional rooms for storage or potential office use. A new rear staircase serves both back doors. Set on a 35-foot-wide lot, the property includes a detached 2.5-car garage with a party door, plus a parking pad, providing three total parking spaces in the backyard. Across the street, 18.7-acre La Follette Park adds a wide range of recreation options close to home. Enjoy an indoor pool, fitness center, tennis and basketball courts, an artificial-turf athletic field for football or soccer, playgrounds, and a water play area. From its detailed ceilings and refinished floors to its expanded layout and convenient parking, this bungalow brings together character, practical updates, and room to make the space your own.

5053 W Potomac Avenue, Chicago

2248 S Kolin Avenue, Chicago
$499,900
5 Beds ⋅ 3 Baths ⋅ 12789574 MLS ⋅ ACTIVE Status
Welcome to one of the largest residential 2-flat properties you'll find in the highly sought-after North Lawndale neighborhood! This property has been fully rehabbed, with the renovation completed in August 2026, offering buyers the opportunity to own a beautifully updated multi-unit property with modern finishes and extensive improvements. Situated on double city lot, this unique property offers an abundance of land and flexibility rarely found in a multi-unit setting. The property sits on one lot with an additional lot on the north side of the property, providing exceptional outdoor space and plenty of room for parking, recreation, expansion, or storage. Business owners with multiple vehicles, work trucks, equipment, or additional parking needs-this could be the ideal property for you! The expansive lot configuration provides valuable space that is difficult to find in the city. Inside, the property features two beautifully remodeled 2-bedroom units, each offering one full bath, a kitchen, and a modern open-concept layout. The second-floor unit is duplexed into the attic, creating additional living flexibility and making the space ideal for an in-law suite, extended family, guests, or other living arrangements. The attic includes its own kitchen and bathroom while sharing central heat with the second-floor unit. The first- and second-floor living spaces each feature their own individual furnace and central heating, providing separate heating systems for each unit. All living areas have been thoughtfully remodeled with modern finishes and an inviting open-concept design. Located in the rapidly developing North Lawndale community, this property offers convenient access to Chicago's Medical District, downtown Chicago, major highways, dining, entertainment, and nightlife. Approximately a 15-minute drive to the Medical District and 25 minutes to downtown, making this an excellent location for both residents and commuters. Whether you're an investor looking for a versatile multi-unit property, an owner-occupant seeking additional living space, or a business owner in need of substantial parking and land, this property offers possibilities that are hard to find. Three lots. Two remodeled units. Recently completed rehab. Exceptional flexibility and space. Don't miss this opportunity-schedule your showing today! This one won't last long!

2248 S Kolin Avenue, Chicago

1644 N Campbell Avenue, Chicago
$1,275,000
5 Beds ⋅ 4 Baths ⋅ 12758681 MLS ⋅ CONTINGENT Status
Set on a tree-lined street in West Bucktown, this true five-bedroom, 3.1-bath home offers nearly 4,000 square feet across three finished levels. Cathedral ceilings, skylights, graceful columns, and a Juliet balcony give the home distinctive architectural character. The main floor begins with a formal entry, a living room with a gas fireplace, and a dining room that comfortably seats 12. The kitchen is designed for both daily use and entertaining, with quartz countertops, a large island, breakfast nook, separate butler's pantry, built-in banquette, and dedicated coffee and wine station. The adjoining family room has a second gas fireplace and access to the rear deck and yard. A cherry blossom tree provides a beautiful view each spring. The primary suite spans nearly the full width of the second floor and includes a substantial walk-in closet and a marble bath with a separate shower and private commode. Two additional bedrooms share a hall bath with a dual vanity. The full lower level offers two more bedrooms, a full bath, and a sink and refrigerator, giving guests, an au pair, or extended family space of their own. A recreation room with unusually high ceilings, a mudroom, a laundry and utility room, and extensive storage complete the level. The detached 2.5-car garage includes an EV charger and a new door with built-in security. Above the garage, a new composite roof deck with a privacy fence provides a second outdoor living area. Recent improvements include refreshed landscaping, two furnaces and two zoned AC systems installed in 2024, a battery-backed sump pump, and whole-home water filtration and Hipa air purification system. This home truly balances quiet and privacy with being part of a genuinely vibrant, walkable neighborhood. It is equally suited to peaceful nights in, busy mornings, or friends gathered around the fire. Ideally located within a 5-minute walk to the 606 Trail, the Milwaukee/Damen/North intersection with tons of shopping, restaurants, and bars. Ample public transit options and close access to I-90 make it a commuter's dream. A rare, true 5-bedroom footprint with the scale, storage, and character to match; this is West Bucktown living at its very best.

1644 N Campbell Avenue, Chicago

3104 W Walton Street, Chicago
$649,900
5 Beds ⋅ 3 Baths ⋅ 12787076 MLS ⋅ PENDING Status
Wonderful Opportunity to own a newly improved multi- unit property in East Humboldt Park! This handsome 2.5 Story full masonry structure Just had an all new and full roof replacement. It now features a new interior drain tile system for protection from water seepage, along the perimeter, a new sump pump, ejector pump and overhead sewer system. The lower level received a fresh coat of paint, new baseboard trim, a few new interior doors, an updated laundry room and a bathroom update! The rear porch has been cleaned up and painted, and there is more! The first floor is a spacious 2 bedroom 1 bath with independent forced air heat, central AC, independent gas and electricity so it is independently metered. The unit is leased out until the end of May 2027 so a live in owner can has extra income for the mortgage The upstairs 2 bedroom 1 bath has a private entrance and a spacious living area, open concept kitchen to living room, tall ceilings, and so much to offer. This floor plan was redesigned to accommodate a live in owner and so it has a massive principal (15x 12) bedroom and a Huge (9x7) walk in closet, in unit laundry, french doors leading to a private rear deck! You will love where you live in this property, or find out just how effortless you can lease this building out as an arm chair investment. This is a must see property with a whole lot of value just added There is a great yard, each unit has its own rear deck, separately metered gas, and electric and more.

3104 W Walton Street, Chicago

1935 N Dayton Street, Chicago
$2,150,000
5 Beds ⋅ 6 Baths ⋅ 12749943 MLS ⋅ PENDING Status
Endless possibilities await with this beautiful brick 2-flat located on the highly coveted 1900 block of Dayton St. Currently configured as an owner's duplex with a spacious, light-filled 3 bedroom + office layout, along with a generous 3 bedroom duplex-down rental apartment, this home offers flexible living and investment potential. Spanning approximately 5,500 square feet across four levels, the property also features fantastic outdoor spaces including multiple decks, a patio, and a roof deck above the extra-wide 2-car garage. This owner's duplex is bright and inviting, offering north, east, and west exposure through an abundance of windows and skylights. The main living level boasts a huge open concept layout with hardwood floors, a bay window seat with views over Dayton, custom bookcases, a gracious dining area, full bathroom, a big kitchen with loads of storage, an office, and a deck off the kitchen with a catwalk leading to the garage rooftop deck overlooking the backyard. The kitchen is complete with wood cabinetry, stainless steel appliances including Subzero, granite countertops, a breakfast bar, and a pantry. The top floor includes three bedrooms, with two ensuite bathrooms, skylights over the stairway, a big laundry closet with a side-by-side washer and dryer, and plenty of storage. The primary suite is a standout with a fireplace, a beautiful lead glass window as a focal point, a walk-in closet, built-in wall closets, skylights, and a bathroom featuring a claw foot soaking tub, steam shower, and a double vanity with white shaker cabinets and quartz vanity top with under-mount sinks. The duplex rental unit is also spacious and filled with natural light. The main living level features a living room with a fireplace and a bay window seat overlooking Dayton St, a big, en-suite bedroom with a walk-in closet and bath with a double vanity, a powder room, and an open-concept kitchen with space for a family or dining room, and a lofted area for an office or den. There is direct access from the kitchen through French doors to the deck and brick-paved patio. The kitchen features wood cabinetry, stainless steel appliances, granite counters, and room for a large dining table. The lower level includes a family room, ensuite bedroom, laundry, an additional office/den/storage room, and extra storage accessed just outside the back door. There is an extra-wide 2+ car garage.

1935 N Dayton Street, Chicago

5012 N Tripp Avenue, Chicago
$555,000
5 Beds ⋅ 4 Baths ⋅ 12787344 MLS ⋅ ACTIVE Status
Prime Chicago Location. Spectacular 5BR, 3.1BA Brick English style home nestled on a quiet tree-lined street in North Mayfair. Offering three levels of living space with baths on all levels. This home has been lovingly cared for by just one family for the last 80 yrs. This residence offers generously sized bedrooms with 2 bedrooms on the main level and 2 upstairs-along with three full bathrooms. The first-floor features include a living room with wood floors, classic dining room, nice size kitchen with plenty of cabinet space and room for a table. 2 main floor bedrooms plus an additional tandem room perfect for home office or 5th bedroom plus a full bath complete the 1st floor. The recently partially dormered second level features 2 more bedrooms and 2 full baths, including a generous primary suite with ensuite bathroom with ample closets. Modern bathroom fixtures with wall hung toilets offers a sleek design and easy to clean floors. New dedicated GFA Carrier furnace and central air on 2nd floor. Stairwell from 1st to 2nd floor has a separate rear entry. The full basement partially finished with half bath, rec room and laundry room with 2 washer/dryers and utility sink. Ample storage. Outside, enjoy a private fenced backyard and a detached two-car brick garage with an extended covered patio area ideal for relaxing or entertaining. Located just steps from Gompers Park with its pool, playgrounds, sports courts, and scenic trails connecting to LaBagh Woods and Forest Glen Woods. Close to Palmer Elementary, shopping, dining, public transit, and I90/94 expressways. One of Chicago's most desirable neighborhoods. Seller is a licensed real estate broker in IL

5012 N Tripp Avenue, Chicago

10145 S Lafayette Avenue, Chicago
$465,000
5 Beds ⋅ 4 Baths ⋅ 12786804 MLS ⋅ ACTIVE Status
Welcome to this spacious, completely rehabbed 6 bedroom, 4 bathroom home in Chicago's Roseland neighborhood! With updates throughout and plenty of room to spread out, this home has a lot to offer. The main level features a large 22 x 18 living room with a decorative fireplace, a separate dining room, and a brand-new kitchen with a large pantry closet. A new stove and dishwasher are coming soon. The first floor also includes a primary bedroom with its own private bathroom, plus a second full bathroom for added convenience. The home offers one bedroom on the main level, four bedrooms on the second floor, and an additional bedroom in the basement. The bedrooms are generously sized, with walk-in closets, and five feature new carpeting, while the remaining bedroom has luxury vinyl flooring. New luxury vinyl flooring has also been installed throughout the main level and basement. In total, the home features four bathrooms: two on the first floor, one on the second floor, and one in the basement. The second floor also includes a convenient laundry area with washer and dryer hookups. The lower level is especially spacious, offering an additional bedroom, a huge open area measuring approximately 57 x 22 feet, a full bathroom, and plenty of storage space. Outside, you'll find a fenced yard, a detached 2-car garage, a driveway for additional parking, and a parking pad in the rear. With six bedrooms, four bathrooms, a new kitchen, fresh finishes, and plenty of parking, this beautifully rehabbed home offers exceptional space and versatility. Whether you're looking for room to accommodate a large household or simply want extra space to suit your needs, this property has plenty to offer. Schedule your showing today and come see all this home has to offer!

10145 S Lafayette Avenue, Chicago

4941 S Kimbark Avenue, Chicago
$1,595,000
5 Beds ⋅ 4 Baths ⋅ 12786855 MLS ⋅ ACTIVE Status
Beautifully updated and move-in ready, this exceptional 3-story brick home on a coveted Kenwood block offers over 4,700 square feet of living space, 5+ bedrooms, 3 1/2 baths, and a fully finished and thoughtfully designed basement. A spacious, covered front porch welcomes you home, offering multiple seating areas and a ceiling fan for comfortable outdoor enjoyment even on the warmest days. Inside, the inviting entry hall opens seamlessly into the gracious living room, featuring a beautiful gas fireplace and built ins. The elegant separate dining room, with its handsome built-in cabinetry, is perfectly positioned between the living room and kitchen, connecting to the kitchen through an open butler's pantry. The spacious eat in kitchen is outfitted with a 2025 premium appliance package, including a Sub-Zero refrigerator, Viking cooktop, Wolf double oven and microwave, and Bosch dishwasher. Just off the kitchen, a large newly refinished deck overlooks the beautiful professionally landscaped yard and leads down to a full-size sport court -- an incredible amenity for recreation and entertaining. A conveniently tucked-away powder room is located beneath the staircase on the main floor. Up the grand staircase, the 2nd floor features a beautifully renovated custom office (with a discreetly integrated full-size washer and dryer), 2 generously sized bedrooms, a cozy family room, and a newly updated full bath. The 3rd floor offers a private primary suite with a newly renovated spa-like bath including radiant heated floors and a large walk in closet. Also on this level are another large bedroom, a fully renovated hall bath, and a versatile 2nd office or 5th bedroom. The fully finished lower level provides an expansive recreation room with endless possibilities-as a family room, play area, craft space, home gym, or whatever best suits your needs. A separate laundry area with sink, large walk-in pantry, second refrigerator and abundant additional storage add to the functionality of this level, which also offers convenient walk-out access to the backyard. Newer mechanicals include heat pump and space pack and 2 water heaters. The flat roof lining was replaced around 2017. This exceptional home combines beautiful original character with thoughtful updates, generous living space, and an impressive array of indoor and outdoor amenities. Truly move-in ready, it offers everything you have been looking for in a beautiful Kenwood home. Easy access to Lake Michigan, downtown transportation, and the University of Chicago campus.

4941 S Kimbark Avenue, Chicago

1962 W Wilson Avenue, Chicago
$1,950,000
5 Beds ⋅ 5 Baths ⋅ 12767615 MLS ⋅ ACTIVE Status
Thoughtfully reimagined in Lincoln Square, this 5-bedroom, 4.5-bath residence spans approximately 4,000 square feet across four finished levels. Fully renovated by an experienced luxury development team known for quality construction, the home has the finish and function of new construction while retaining select original character. Nearly 10' ceilings, white oak floors, substantial millwork, custom built-ins, solid-core doors, designer lighting, and a beautifully restored original 1900 fireplace carry throughout. The kitchen is anchored by an oversized 5' x 8' island, with natural-tone cabinetry, quartz surfaces, marble tile, Thermador/Wolf appliances, and built-in breakfast seating. Adjoining living and dining spaces open directly to a deck and private, low-maintenance backyard. Two primary suites offer a rare degree of flexibility: one on the second level with a spa-inspired bath and oversized shower, and a private top-floor suite with space for a sitting area, office, or gym. The finished lower level includes a recreation room with custom built-ins, wet bar and wine cooler, fifth bedroom, full bath, second laundry area, and storage. Dual high-efficiency HVAC, spray-foam insulation, 200-amp service, integrated security and media wiring, and a detached two-car garage prepped for EV charging complete the home. Directly across from Lycee Francais and moments from the Damen Brown Line, with neighborhood cafes, restaurants, parks, the farmers market, and the best of Lincoln Square all close by.

1962 W Wilson Avenue, Chicago

3921 N Greenview Avenue Unit #1, Chicago
$1,450,000
5 Beds ⋅ 3 Baths ⋅ 12786614 MLS ⋅ ACTIVE Status
Nestled on a one-way street in the Southport Corridor, this 5-bedroom, 3-bathroom duplex down offers the space and functionality of a single-family home on an oversized 27' x 183' lot. The main level features separate living and dining areas anchored by a fireplace, flowing into a stunning remodeled chef's kitchen with white quartz countertops, Wolf oven, Sub-Zero refrigerator, and updated lighting. Three bedrooms are located on this level, including the primary suite with a walk-in closet, private rear balcony, and remodeled bath featuring marble tile, heated floors, dual vanity, soaking tub, and separate steam shower. All three bathrooms have been remodeled or updated. The lower level includes 10-foot ceilings, radiant heated floors, a family room with a second fireplace, wet bar, and built-in office area, along with two additional oversized bedrooms and a full bath. A laundry room with side-by-side washer and dryer, utility sink, and storage, plus a mudroom with direct access to the garage, provide everyday convenience. Outdoor spaces include a professionally landscaped private backyard with irrigation and a private garage rooftop deck with Ipe decking, pergola, and electric service. Additional features include all-brick masonry, custom millwork, two furnaces, garage parking plus exterior tandem parking, and an extra-large private storage unit in the basement. Located within the Blaine Elementary School boundaries and steps to Southport's restaurants, shops, parks, and neighborhood amenities, this home offers flexible living space in West Lakeview. A rare opportunity to enjoy the space of a single-family home with the convenience of condo living in the heart of the Southport Corridor.

3921 N Greenview Avenue Unit #1, Chicago

812 S Miller Street Unit #G, Chicago
$495,000
5 Beds ⋅ 2 Baths ⋅ 12785547 MLS ⋅ ACTIVE Status
**MOTIVATED SELLER - EXCEPTIONAL INVESTMENT OPPORTUNITY IN LITTLE ITALY NEAR UIC!** An outstanding opportunity for investors seeking strong rental income and long-term appreciation potential in one of Chicago's convenient rental markets. This spacious approximately 2,500-square-foot ground-level residence features **5 bedrooms, 2 full bathrooms, and current rental income of $4,250 per month, offering an attractive income-producing asset with potential for future rent growth. Ideally situated in the heart of Little Italy, just steps from the University of Illinois Chicago (UIC) and the vibrant Taylor Street corridor, this property benefits from convenient access to the university, medical campuses, restaurants, cafes, shopping, and public transportation. Its location also provides easy access to the West Loop, downtown Chicago, the Loop, and major expressways-an appealing combination for students, medical professionals, university employees, and other urban renters. Inside, the generously sized layout offers five bedrooms, updated flooring, kitchen appliances replaced in 2021 and 2026, and a gas fireplace. One exterior parking space is included-a valuable convenience in this sought-after city location-with additional street parking available nearby. The combination of substantial living space, multiple bedrooms, established rental income, and convenient access to major employment and education centers makes this an attractive addition to an investment portfolio. The property may also appeal to owner-occupants looking for a spacious city residence with income-producing potential.

812 S Miller Street Unit #G, Chicago

3318 W Flournoy Street, Chicago
$325,000
5 Beds ⋅ 2 Baths ⋅ 12776067 MLS ⋅ PRICE CHANGE Status
**Great Investment Opportunity Just Minutes from Downtown Chicago!** Discover the potential of this spacious **Brick Greystone two-unit property**, ideal for investors and owner-occupants looking to build equity or expand their real estate portfolio! This beautiful Chicago Greystone offers generous living spaces and extra-large bedrooms on both levels. The **second-floor unit features 3 bedrooms and 1 bathroom**, while the **first-floor unit offers 2 bedrooms and 1 bathroom with a duplex layout connecting to the unfinished basement**. Bring your vision and creativity to the basement, offering exciting possibilities for future improvements and customization, subject to applicable building codes and approvals. **Both units are currently vacant**, giving the next owner the flexibility to move right in, establish rental income, or make improvements to maximize the property's potential. The spacious, open backyard offers additional possibilities for a newly constructed garage, concrete parking slab, or outdoor entertainment space. Conveniently located with access to downtown Chicago, major expressways, shopping, dining, and public transportation. Whether you're a seasoned investor looking to expand your portfolio or an owner-occupant interested in house hacking, this **Chicago Greystone** offers space, character, flexibility, and outstanding value-add potential. **Bring your ideas, explore the possibilities, and make this investment your own!**

3318 W Flournoy Street, Chicago

5438 W Melrose Street, Chicago
$559,900
5 Beds ⋅ 3 Baths ⋅ 12784810 MLS ⋅ PRICE CHANGE Status
Incredible opportunity for Home owners or investors to own a spacious bungalow in the heart of the highly desirable Portage Park neighborhood! This property will paid off on it's own with collected rent. This oversized home features 3 levels of living space and offers exceptional flexibility for extended families, related living, or investment potential. The property includes 8 total bedrooms, 3 full bathrooms, and 3 kitchens, with each level offering its own separate living area. The main floor kitchen features granite countertops, stainless steel appliances, and 42" tall cabinets, offering both style and functionality. A main floor office is currently being used as an additional bedroom, providing even more flexible living arrangements. The basement primary bedroom features two walk-in closets, and the home offers an abundance of storage space throughout. The second floor has separate electrical service, and the property is equipped with 2 separate high-efficiency HVAC systems for added comfort and efficiency. Major updates include a newer roof (approximately 4 years old), vinyl windows throughout, updated mechanicals, and a newer electrical panel. Enjoy two cozy decks perfect for relaxing or entertaining. The oversized garage with 10-foot garage doors can accommodate large vans, including the largest Sprinter models, making it ideal for contractors, business owners, RV storage, or additional workspace needs. The home also offers two separate laundry areas for added convenience. Fantastic location close to parks, schools, shopping, restaurants, and public transportation. A rare opportunity with endless possibilities. Schedule your showing today and bring your offer!

5438 W Melrose Street, Chicago

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