View All North Center Chicago IL Homes with Guest House Listings

3 Beds ⋅ 2 Baths ⋅ 12577262 MLS ⋅ CLOSED Status

Located on a rare cul-de-sac in Lincoln Square, this well-maintained 3-bed, 2-bath residence offers a quieter residential setting within the highly sought-after Coonley School District. The home is intelligently designed across three finished levels, beginning with a bright, open main floor that features hardwood and ceramic flooring, oversized windows, and a seamless flow from the living area to the kitchen overlooking the private backyard. Situated on an oversized lot, the home offers a sense of privacy and space from neighbors that is truly rare for the area. On the upper level, you'll find comfortably sized bedrooms with ample storage along with a recently renovated full bathroom. The basement offers exceptional flexibility, featuring a partially finished area perfect for a cozy media lounge, home office, or guest quarters, complete with a second full bathroom, dedicated laundry room, and ample storage space. Outdoor enthusiasts will appreciate the large private backyard, ideal for gardening or entertaining under the city sky. Located near the Western Brown Line station, multiple grocery stores, and the vibrant dining and shops of Lincoln Square, this home provides effortless access to everything you need. Take inspiration from neighboring homes that have added garages with expanded living space above or extended behind the house over time. With its multi-level floor plan, spacious lot, and prime location, this property offers a rare combination of space and convenience in one of Chicago's most desirable neighborhoods.

4222 N Claremont Avenue, Chicago

$2,550,000

5 Beds ⋅ 5 Baths ⋅ 12571083 MLS ⋅ CLOSED Status

This spectacular home boasts a captivating brick facade that blends classic elegance with limestone accents and clean lines. 5 Bdrm, 4.1 Bath home on a 30 ft lot offering 4,500 sq ft of luxurious living. Wide floor plan together with 10' ceilings provides exceptional space for living and entertaining. Home wired for sound with speakers included. Extensive high-quality millwork throughout the whole house - wainscotting, crown molding, trims. The chef's kitchen features 6-burner range, Thermador fridge, huge island, butler pantry and a wine fridge. Flowing seamlessly from the kitchen, the spacious family room with a gas fireplace and custom built-ins, with direct access to the rear deck for same-level outdoor living. Lower level features radiant heated floors, a spacious Rec Room with wet bar, an office, guest bedroom, full bathroom, sauna, and 2nd laundry setup. Outdoor space features a brick-paved patio, outdoor fireplace, and a garage rooftop deck. Front steps with radiant heat for worry-free winters. Located in the vibrant North Center neighborhood across the street from Bell School.

3723 N Oakley Avenue, Chicago

$1,699,000

2 Beds ⋅ 4 Baths ⋅ 12570881 MLS ⋅ CLOSED Status

One-of-a-kind transformation of a classic Chicago brick two-flat into a custom-designed single-family residence in the heart of Northcenter. Affectionately known by neighbors as the "Gas-Light House," this distinctive 3-level home blends early 1900s craftsmanship with exceptional modern upgrades. You are welcomed into the dramatic two-story entry gallery featuring a 20-foot exposed brick wall and hand-crafted steel staircase-a showcase of timeless masonry and custom design. The open-concept main level offers generous living and dining spaces, complete with a bar/office nook and space to display your prized collectibles or vintage motorcycles. The chef's kitchen is truly exceptional: a 10-burner Lynx Star Pro range with double oven, stainless Viking commercial-grade double hood, Sub-Zero refrigerator and separate freezer, granite-topped center island, custom buffet, and butler's pantry. A hidden powder room with Art Deco flair completes the main level. Upstairs, the front bedroom is bathed in natural light and served by a full vintage Kohler bath featuring a clawfoot soaking tub. The rear of the upper level is dedicated to the luxurious primary suite, with sound-absorbing upholstered walls, built-in surround sound, and a spa-inspired bath with Jacuzzi tub and glass-enclosed shower-featured on HGTV's "Love That Bath". The custom walk-in closet offers extensive storage with accent lighting and built-ins. The lower level includes a private home gym, guest bedroom, full bath, and a bright, well-appointed laundry room with high-end appliances, cabinetry, utility sink, and hanging space. At the rear of the home, the stunning family room addition pays homage to Prairie and Arts & Crafts architecture-with rich wood-paneled walls, beamed ceilings, gas fireplace, stained glass windows, and period-perfect lighting. Glass doors open to a beautifully landscaped patio beneath a soaring pergola, ideal for outdoor entertaining. The heated 2019-built garage is more than just a parking space: it includes a lofted storage level, workshop power supply, fire-resistant Hardy board siding with wood shake accents, and reclaimed original windows and doors. Outdoors, enjoy a built-in grilling station with a stainless Lynx rotisserie infrared grill, storage, and a peaceful koi pond. Mechanically superb, the home features dual-zone HVAC, new windows, a rubber roof, gutter heaters, upgraded drainage, and a comprehensive flood protection system-all sure to impress your inspector. Priced accordingly for the 3-bedroom layout. Located on one of Northcenter's most coveted blocks, just steps to award-winning Bell School, Lane Tech, parks, restaurants, shops, theaters, public transit, Wrigley Field, Lake Michigan, and the North Branch Riverwalk. This home would be extraordinary anywhere-but here, it's exceptional. Come experience it for yourself.

3822 N Claremont Avenue, Chicago

$2,000,000

6 Beds ⋅ 6 Baths ⋅ 12467472 MLS ⋅ CLOSED Status

The open is canceled. The property is under contract. Tucked behind a storybook front yard on a tree-lined block, this newly constructed home with interiors by Hubbard Design Group blends playful warmth with quiet sophistication. Set on an extra-wide and extra-deep 30' x 154' lot, the home is set back from the street, giving you a broad green lawn and a welcoming 9-foot covered front porch. It's the kind of yard that begs for sidewalk chalk, lemonade stands, and slow Sunday mornings; equal parts privacy and presence. Inside, timeless elegance meets modern comfort. White oak flooring, subtle millwork, and airy 10-foot ceilings lend every room a sense of refined ease. At the front of the home, the formal living and dining room is anchored by a gas fireplace with a hand-finished surround, flanked by tall windows, perfect for holiday dinners or cozy evenings in. Beyond a graceful arched, wide hallway, the heart of the home opens up: a show-stopping kitchen and family room that balances function and form. The double-sided island seats five, topped with Calacatta quartzite. Custom off white cabinetry frames two 30" built-in refrigerator and freezer columns and pairs with a Wolf 48" gas range. A hidden scullery with a second dishwasher and sink makes entertaining effortless and everyday life beautifully contained. Designer tile accents and a full-height backsplash add visual richness. Arched built-ins surround the family room fireplace, and natural light pours in from all sides. Downstairs, the fully radiant-heated lower level is designed for real life. Host movie nights in the rec room, store your favorites in the glass-enclosed wine cellar, or retreat to the spa-inspired 7' x 9' sauna after a long day. There's also a guest suite with a full bath, a flex space perfect for a gym or sixth bedroom, and a wet bar with designer fixtures for good measure. Upstairs, family living is reimagined. Four bedrooms-three with ensuite baths-provide comfort and autonomy. The primary suite, thoughtfully located at the front of the home, offers peaceful treetop views and sunlight throughout the day. A spa-inspired bath features heated floors, a soaking tub, a luxurious walk-in steam shower and a private water closet, while a spacious walk-in closet keeps everything in order. And then there's the train-yes, it's behind the house. But what could have been a flaw has been reimagined. The home was pushed back on the lot, creating the deep front yard and engineered acoustics that make the occasional rumble feel more like a hum-city energy at a gentle distance. Inside, you'd hardly notice. Outside, you're reminded that convenience lives just steps away. Location-wise, 4243 N Wolcott straddles the line between North Center and Ravenswood, claiming the best of both. You're in the desired Ravenswood Elementary district - a big plus for families seeking excellent public schools. Within blocks, you'll find family essentials and neighborhood charm in every direction. Saturday mornings start at the Northcenter Farmers Market, where live music, pastries, and produce are as much a ritual as a resource. Grab coffee at Spoken or Hexe on your stroll home, or treat the family to breakfast in the garden courtyard at Willow Cafe and Bistro. When dinner rolls around, options abound: sizzling Korean BBQ at Cho Sun Ok, wood-fired pies from Spacca Napoli, or a burger at The Bad Apple. Family-friendly breweries like Begyle, Half Acre, and Dovetail offer relaxed patios, food trucks, and community vibes where strollers and pints are equally welcome. And with beloved local events like Ribfest, Harvest Jam, and movie nights in Welles Park, the calendar fills itself. This is more than just a home; it's a backdrop for a life with rhythm, intention, and joy. In a city that often asks for compromise, 4243 N Wolcott gives you space, style, and neighborhood spirit without asking you to give anything up.

4243 N Wolcott Avenue, Chicago

$1,605,000

4 Beds ⋅ 4 Baths ⋅ 12360192 MLS ⋅ CLOSED Status

Masterfully rebuilt in 2021, this stunning residence offers 4 bedrooms and 3.1 bathrooms in the heart of North Center with added bonus of unique 500 sq ft detached guest suite! The separate, detached heated guest suite has office space, offers radiant heated floors, full bathroom, and attached one-car garage (perfect for guests or in-law arrangement)! Hardwood floors, custom millwork, and recessed lighting flow throughout main and upper levels, creating an elegant backdrop for refined living. Positioned on a highly coveted, cul-de-sac-like street with beautiful mature trees, this home's main level's open-concept design showcases oversized windows flooding living spaces with natural light, featuring built-in arched bookshelves and perfect space for large dining table. Gourmet kitchen impresses with duo-tone cabinetry featuring white perimeter cabinets and large island with dark navy blue cabinetry and breakfast bar seating, thick quartz countertops, Wolf stove with griddle, Sub-Zero refrigerator with panel-front matching cabinetry, herringbone tile backsplash, shiplap-wrapped range hood, and gorgeous farmhouse sink! Thoughtfully designed mudroom offers custom storage solutions, while neighboring powder room charms with vintage wall-mounted sink. 2nd level leads you to your spacious primary suite filled with abundant natural light! Spa-inspired primary bath boasts wall-to-wall double sink vanity with ample storage, full wall custom tile backsplash, and luxurious walk-in steam shower with bench seating. Two additional bedrooms down the hall share well-appointed full bath with dual sink vanity and shower/tub combo. Second-floor laundry provides modern convenience. Light-filled basement features luxury vinyl plank flooring, built-in storage with desk area, versatile fourth bedroom currently utilized as home gym with adjacent 3rd full bathroom showcasing floor-to-ceiling tile work and frameless glass shower door - this space can easily be utilized as guest space, in-law arrangement, or home office! Superior finishes, designer light fixtures, and thoughtful details throughout entire home. Enjoy the outdoors with spacious patio that creates a perfect outdoor entertaining space connecting the main house to the detached guest suite! Your sizable grassy front yard is perfect for outdoor activities, gardening, or simply relaxing in a serene, green setting. Walking distance to Welles Park, steps from North Center's vibrant dining and shopping district, and convenient to Brown Line transportation. Easy access to Lake Shore Drive and I-90/94 expressways. Welcome home!

2312 W Hutchinson Street, Chicago

$2,000,000

4 Beds ⋅ 6 Baths ⋅ 12373013 MLS ⋅ CLOSED Status

SOLD BEFORE PRINT. Tucked behind a storybook front yard on a tree-lined block, 4243 N Wolcott is a newly constructed home designed by Hubbard Design Group that blends playful warmth with quiet sophistication. Set on an extra-wide and extra-deep 30' x 154' lot, the home sits back from the street, allowing for a generous green lawn and a welcoming 9' front porch. It's the kind of yard that begs for sidewalk chalk, lemonade stands, and slow Sunday mornings-equal parts privacy and presence. Inside, timeless elegance meets modern comfort. White oak floors, custom millwork, and high ceilings lend every room a sense of refined ease. At the front of the home, the formal living and dining room is anchored by a stately fireplace flanked by tall windows, perfect for holiday dinners or cozy evenings in. It's elevated but never showy-a home where quality speaks quietly. Beyond a graceful arched hallway, the heart of the home opens up: a show-stopping kitchen and family room that balances function and form. The double-sided white oak island seats five, inviting everything from pancake breakfasts to science fair prep. Warm cabinetry, integrated appliances, and a hidden scullery with a second dishwasher and sink make entertaining effortless and everyday life beautifully contained. Arched built-ins surround the family room fireplace, and natural light pours in from front to back. Downstairs, the fully radiant-heated lower level is designed for real life. Host movie nights in the rec room, store your favorites in the glass-enclosed wine cellar, or retreat to the sauna after a long day. There's also a guest suite with a full bath, a flex space perfect for a gym or sixth bedroom, and a wet bar for good measure. Upstairs, family living is reimagined. Four bedrooms-three with ensuite baths-provide comfort and autonomy. The primary suite, now thoughtfully located at the front of the home, offers peaceful treetop views and sunlight throughout the day. A spa-inspired bath features heated floors, a soaking tub, walk-in shower, and private water closet, while a spacious walk-in closet keeps everything in order. And then there's the train-yes, it's behind the house. But what could have been a flaw has been reimagined. The home was pushed back on the lot, creating the deep front yard and quiet indoor acoustics that make the occasional rumble feel more like a hum-city energy at a gentle distance. Inside, you'd hardly notice. Outside, you're reminded that convenience lives just steps away. Location-wise, 4243 N Wolcott straddles the line between North Center and Ravenswood, claiming the best of both. You're in the desired Ravenswood Elementary district - a big plus for families seeking excellent public schools. Within blocks, you'll find family essentials and neighborhood charm in every direction. Saturday mornings start at the Northcenter Farmers Market, where live music, pastries, and produce are as much a ritual as a resource. Grab coffee at Spoken or Hexe on your stroll home, or treat the family to breakfast in the garden courtyard at Cafe Selmarie. When dinner rolls around, options abound: sizzling Korean BBQ at Cho Sun Ok, wood-fired pies from Spacca Napoli, or a burger at The Bad Apple. Family-friendly breweries like Begyle, Half Acre, and Dovetail offer relaxed patios, food trucks, and community vibes where strollers and pints are equally welcome. And with beloved local events like Ribfest, Harvest Jam, and movie nights in Welles Park, the calendar fills itself. This is more than just a home-it's a backdrop for a life with rhythm, intention, and joy. In a city that often asks for compromise, 4243 N Wolcott gives you space, style, and neighborhood spirit-without asking you to give anything up. WalkScore 91 | TransitScore 70 | BikeScore 76 | 28-minute Lyft, 33-minute L ride, or a 41-minute cycle to The Loop | 4 Divvy stations within 0.2 mi or less | 0.2 mi to the Montrose Brown Line station | The 50/78/80 bus lines are within 0.5 mi or closer.

4305 N Wolcott Avenue, Chicago

$1,235,000

4 Beds ⋅ 4 Baths ⋅ 11917008 MLS ⋅ CLOSED Status

Welcome to this stunning, new construction duplex down home situated on a 32-foot-wide lot in the desirable neighborhood of North Center and Audubon school district. Built by long standing home developer, Mangan Builders, this home offers the perfect blend of modern design and timeless elegance. This extra wide floorplan offering four bedrooms three and a half baths with unmatched private outdoor space and garage parking lives like a single-family home and boasts ample space for comfortable living. Enormous eat-in kitchen with top-of-the-line appliances, oversized waterfall quartz island, two-toned cabinetry, black absolute flamed granite, and large walk-in pantry make this kitchen a chef's dream. Large family room off the kitchen with gas fireplace and Calacatta stone mantle opens to a massive 400 square foot covered terrace covered with pavers and turf featuring an outdoor fireplace, water, electric and gas; perfect for entertaining. Spacious living room with huge windows allowing light to flood the entire room can also be used as a formal dining room and features a dry bar with additional cabinets for flatware. Stylish powder room and additional closets complete this floor. Lower level with 4 bedrooms and 3 bathrooms features lush carpet and radiant heated flooring throughout. Spacious primary bedroom with detailed accent wall paneling and a massive walk-in closet fully built out. Spa like ensuite bathroom features rain shower, separate soaking tub, double vanity, stone countertops, and heated tiled floors. Sizable second and third bedroom with built out closets. Fourth bedroom features an ensuite bathroom and is perfect for a guest suite. Full laundry room with utility sink, mud room, and additional closet space complete this magnificent home. 1 bedroom coach house also available for $299,000. This full brick and limestone building with a timeless facade boasts top of the line finishes and quality throughout including concrete in-between floors and designer finishes. With its prime location, you'll enjoy the convenience of being just steps away from all the vibrant shops and award-winning restaurants that Roscoe Village and North Center have to offer, along with the highly regarded school district.

3651 N Damen Avenue Unit #1, Chicago

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North Center, Chicago IL · Curated MLS Search

Homes with Guest House in North Center, Chicago IL

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