North Side Homes for Sale

**Discover the Charm of North Side: Your Next Home Awaits!**

Nestled along the picturesque banks of the river, North Side is a vibrant neighborhood that effortlessly blends urban convenience with suburban tranquility. Known for its rich history and diverse community, this area offers a unique living experience that appeals to families, young professionals, and retirees alike. Tree-lined streets are adorned with charming boutiques, cozy cafés, and a variety of dining options, making it a delightful place to explore on foot.

North Side boasts an array of homes for sale, catering to a wide range of tastes and budgets. From historic brownstones that exude character to modern condos featuring sleek designs and stunning views, there’s something for everyone. Many properties come equipped with spacious backyards, perfect for summer barbecues or a tranquil retreat after a long day. Additionally, the neighborhood is known for its excellent schools and proximity to parks, making it an ideal choice for families looking to settle down.

As you explore the homes for sale in North Side, you’ll discover a community that values connection and engagement. Residents often gather for local events, farmers' markets, and seasonal festivals, fostering a strong sense of belonging. With easy access to public transportation and major highways, commuting to downtown or neighboring areas is a breeze.

Don’t miss the opportunity to make North Side your new home. With its charming atmosphere, diverse housing options, and welcoming community spirit, it’s the perfect place to create lasting memories. Start your home search today and experience all that North Side has to offer!

Newest North Side Homes for Sale

$980,000

5 Beds ⋅ 3 Baths ⋅ 12802422 MLS ⋅ NEW Status

Just when you thought you would never find a house! Nestled in the charming area of East Rogers Park, a stately Vintage Victorian home Turn-of-the-Century Victorian Home on DOUBLE LOT, 5 bedroom, 3 bath home beautifully loaded with vintage and gorgeous custom features. Built in 1892, this home graces an expansive 50-foot wide lot, with a welcoming 25x8 porch that spans the front facade. Sunny large living room with bay window, separate first floor parlor/rumpus/TV room/, formal dining room with gorgeous custom hand-milled hutch w roll-out drawers and rain glass cabinet doors. Hand-milled Birch pocket door glides with ease between parlor and dining room. Expect to be impressed by this AMAZING STUNNING CHEF'S KITCHEN with 100% all Custom Hand-Milled Poplar and Birch Wood Cabinetry! Roll-outs, Lazy Susan, and a H-U-G-E Pantry are just some of the fabulous features. The rear sunroom with Cathedral ceiling beadboard overlooking the backyard is perfect for enjoying your morning meal. Step out the back door and enjoy the covered deck, perfect for BBQ. I can almost smell those steaks cooking, can't you? Beautifully Renovated First floor bathroom with shower will impress your guests. The 2nd floor has 4 bedrooms, fully Renovated bath will spoil you while you enjoy the extra deep soaking tub with a separate shower with frameless glass doors. Top/Attic floor with 5th bedroom and 3rd bath is a huge space and can be a magnificent master suite, yoga studio, family room or more! Full unfinished walk out basement with dark room for your budding photographer, or use as wine storage. Large workman's bench in basement and another in the garage. Completely fenced back and side yard perfect for gardening, summer parties, or a neighborhood kids hang-out. Newer 3 car garage, with a 2-4 car driveway for extra parking for parties. The BIG EXPENSIVE STUFF, Complete Kitchen, 2 Complete Baths, Roof, Gutters, Electric, Plumbing, Garage, Siding, Windows, Furnace, A/C, Water Heater, Kitchen Appliances, are all NEW or NEWER. Too Much to try to list here. BE SURE TO READ THE ADDITIONAL INFORMATION WITH TONS OF DETAILS IN THE DROPDOWN BOX. A short walk to Redline or Metra, 2.5 blocks to Lake Michigan, Beach and Parks, a short stroll to restaurants, pubs, and shopping! A FABULOUS Home in Rogers Park! Remember, It's ALWAYS Cooler by the LAKE!

6742 N Glenwood Avenue, Chicago

$275,000

3 Beds ⋅ 3 Baths ⋅ 12796033 MLS ⋅ NEW Status

4556 Sheridan Street, Davenport

$340,000

4 Beds ⋅ 3 Baths ⋅ 12784914 MLS ⋅ NEW Status

Cute as a button and move in ready! This 4 bed- 3 full bath cape cod home boasts main floor laundry, a walk out basement, 2 main floor bedrooms, 2 upstairs bedrooms, the master has a unique vanity and sink connected to the walk-in closet, and a large non-conforming room in the basement along with a family room and full bath. The living room has a beautiful gas fireplace as a focal point and new lvp, not to mention a gorgeous 4 season room off of the updated kitchen. The landscaped fenced backyard also has a 16x16 shed with power and a new patio to entertain or relax. Seller retains ring cameras.

2733 E 50Th Court, Davenport

$700,000

4 Beds ⋅ 2 Baths ⋅ 12802222 MLS ⋅ NEW Status

HOT EDGEWATER LOCATION! Attention investors, builders, and developers. A rare opportunity presents an exceptional redevelopment opportunity in the sought-after Edgewater/Andersonville/West Ridge corridor. This long-time family-owned home has been cherished for over 60 years and is ready for its next chapter. Built around 1900, the property offers approximately 1800 sq. ft. of above-grade living space, plus a full basement, and currently features 4 bedrooms and 1.5 bathrooms. Whether you're a developer, investor, or buyer looking to create your dream home, this property presents endless possibilities. Ready for a complete renovation or new construction, this is your chance to transform a classic Chicago property in one of the city's most sought-after neighborhoods. Enjoy close proximity to the lake, parks, dining, shopping, public transportation, and everything the city has to offer. Property is being sold as-is and requires major renovations Utilities are currently off, including electricity and gas. Daytime showings only due to lack of lighting.

6320 N Glenwood Avenue, Chicago

$1,100,000

3 Beds ⋅ 3 Baths ⋅ 12799949 MLS ⋅ NEW Status

Gorgeous move in ready 4 bedroom 3 bathroom single family home with a finished basement in the highly coveted gated community of Landmark Village in West Lakeview/Roscoe Village! A one-of-a-kind "suburb in the city" where neighbors play ball and ride bikes in the streets, block parties happen every summer, and weeknight food trucks are the norm. Welcome guests into your new home which features an adorable front porch with newer Trex decking and a spacious formal foyer with a coat closet which opens to a massive living room featuring a wood-burning fireplace with gas starter. Across from the living room is a large dining room which easily fits a table for 10, perfect for entertaining as well as the kitchen which has white cabinets, granite countertops and newer stainless steel appliances. The second level features three bedrooms and two full bathrooms. The primary suite, which has vaulted ceilings, easily fits a king-sized bed with ample space for nightstands and dressers and features a wood burning fireplace as well as two walk-in closets. Attached is the sunny primary ensuite bathroom with dual sinks. Two additional bedrooms, one of which has direct access to a private sundeck, and a renovated 2nd bathroom complete this floor along with a linen closet. Downstairs is a fully finished basement with a family room featuring a gas fireplace, the 4th bedroom which is massive and easily functions as a guest room/office, a full bathroom and the laundry room with side-by-side washer and dryer, and an extra storage area! 1 car attached garage and 1 exterior space in the driveway! Guest parking available in community as well but requires permit passes, which are free. The backyard, accessed from the kitchen, features a paver patio but could be converted to grass or artificial turf and fenced in, if so desired. Updates abound in this well-cared for home! Basement bathroom renovated 2024, interior painted 2024, custom closets in primary bedroom and nursery 2024, New ejector pump 2025 and asphalt driveway 2023, new roof 2021, new water heater 2024, new Trane AC and furnace in 2026, new washer/dryer 2024, new microwave 2025, new dishwasher 2024, new fridge and oven 2017, landscaping professionally redesigned 2024, new Trex decking on front porch 2025, among many other updates. This single-family home is part of the homeowners association of Landmark Village and the monthly assessments take care of the water, garbage, landscaping, snow removal (except owners have to shovel their own driveways), and common maintenance of the gates, streets, and intercom system. A+ location for fun just steps from Hamlin Park, Che-Chi Wang Park, Weibolt Park, and Jahn playground. Walk to Whole Foods, Jewel, Menards, Costco, the Brown line EL at Paulina or Diversey, Midtown Athletic Club, and the shops and restaurants of both Roscoe Village & Southport Corridor. Single family homes with basements in this highly desirable gated community rarely come on the market so don't let this fantastic opportunity pass you by!

2859 N Wolcott Avenue, Chicago

$1,400,000

6 Beds ⋅ 5 Baths ⋅ 12801445 MLS ⋅ NEW Status

Remarks: Developers, investors, and anyone looking to put down roots in the absolute heart of the Southport Corridor, here is your opportunity. Set on a rare, oversized 30 ft lot just steps from everything Southport has to offer, this property provides multiple options for anyone looking for a wider layout in the area. Owners looking to put down roots can renovate to create the home of their dreams. Investors looking to take advantage of increased rents can add value and hold as a long-term investment. Developers, this 30 ft wide footprint will sell immediately. The home has been used as a single family for many years, but has separate access points to the upper and main levels, with separate kitchens and baths, providing the option of renting out the units immediately if so desired. The upper floor provides two bathrooms, one full bath and one half bath, while the main level and basement provide an additional four beds and three full bathrooms. The home provides beautiful original millwork, built-ins, doors, and fireplaces that can be salvaged or reused during renovations. The property has been well cared for. Electrical has been updated and inspected, and a new boiler has recently been installed. On the rear of the property sits an oversized three-car parking pad to be used as the new owner sees fit, completely free of obstructions such as utility poles, etc. For those not familiar with the immediate location, Bosworth offers exceptional walkability to some of Lakeview and Southport's most sought-after neighborhood amenities. You're just steps to acclaimed restaurants such as Coda di Volpe and Crosby's Kitchen, neighborhood parks such as Margaret Donohue, and just minutes from Lake Michigan.

3420 N Bosworth Avenue, Chicago

$459,000

2 Beds ⋅ 3 Baths ⋅ 12800449 MLS ⋅ NEW Status

New roof. New siding. Both done in 2023, so the big exterior items are handled for years to come. This home sits on a level 0.24 acre lot in Prairie Heights with a three-car attached garage. The main level has 9' ceilings, a gas log fireplace in the living room and a kitchen with granite counters and an island. You'll find the primary bedroom, a second bedroom, and laundry all on one floor. The finished basement adds an additional living space, a third bedroom, a bath, and plenty of storage. Out back: a screened porch, a deck, and an above-ground pool that stays. 3 full baths. Central air, sump pump and radon mitigation in place.

6135 Deere Creek Lane, Davenport

$970,000

5 Beds ⋅ 2 Baths ⋅ 12800256 MLS ⋅ NEW Status

Located in Chicago's coveted Lincoln Square neighborhood, this five-bedroom, two-bathroom single-family home offers an excellent opportunity to own in one of the city's most sought-after North Side communities. The lot width (36') provides greenery and generous light from both the side and back yards. With five bedrooms, there is plenty of flexibility for a growing household, guest accommodations, a home office, or additional living space to suit your needs. Whether you're looking to move right in, personalize a home to reflect your style, or explore its full potential, this property presents the chance to enjoy the space and convenience of single-family living in a highly sought-after neighborhood. The property is situated on a quiet, tree-lined street, a half block from Winnemac Park and located in the Amundsen and McPherson school districts. Truly an A+ location that is a short stroll to Lincoln Square's vibrant pedestrian strip. Enjoy effortless access to boutique shopping, world-class dining, local bakeries, Winnemac Park, the Davis Theater, the Damen or Western Brown Line CTA station, and the Ravenswood Metra Station. Don't miss your chance to start your next chapter in this charming neighborhood.

4935 N Seeley Avenue, Chicago

$7,995,000

7 Beds ⋅ 7 Baths ⋅ 12773593 MLS ⋅ NEW Status

An architectural triumph in the heart of Chicago, this extraordinary 7 bed/7 bath East Ravenswood residence pairs the scale and sophistication of a private retreat with the warmth and livability of a true family home. Designed by award-winning Chicago architect Chip von Weise of von Weise Associates, the approximately 12,000-square-foot residence is thoughtfully composed as three distinct pavilions connected by dramatic glass-enclosed stair halls, creating an effortless dialogue between architecture, landscape, and light. Set on an exceptional 92-by-165-foot lot, the home unfolds around a private outdoor oasis with a 13-foot-deep swimming pool, spa, generous terraces, a fire pit, and lush professional landscaping. Radiant-heated pavers, sidewalks, and driveway extend the home's comfort well into the colder months, while the three-car attached garage and expansive drive provide parking for several additional vehicles. Inside, walls of glass and a refined palette of limestone, stucco, zinc, and warm woods create a sophisticated yet inviting backdrop. The expansive main level offers gracious entertaining spaces, a stunning Ernestomeda kitchen with custom cabinetry, a family room anchored by a fireplace, formal office, and seamless access to the terrace and pool. Multiple fireplaces add warmth throughout (eight in total), while beautifully appointed powder rooms-including one with antiqued mirror wall panels-bring an unexpected note of glamour. The private quarters are equally impressive, with seven bedrooms on the second level, along with an office and gym. A flexible secondary living area provides an ideal gathering space, while the lower level takes the concept of home recreation to another level with a full sport court, recreation room, and home theater. Featured in Modern Luxury as an "Everyday Getaway," the residence was conceived as a place where sophisticated design and everyday life could coexist beautifully. Every detail reflects that philosophy: elevated enough to impress, comfortable enough to truly live in, and designed to make the most of its remarkable indoor-outdoor setting. A rare opportunity to own an architecturally significant private retreat with the amenities of a five-star resort, all within the city.

4401 N Hermitage Avenue, Chicago

$329,900

3 Beds ⋅ 2 Baths ⋅ 12799828 MLS ⋅ NEW Status

Outstanding ,5 bedroom split foyer with over 1700 square feet of living space. VERY open floor plan with cathedral ceilings, eat-in kitchen with breakfast bar and newer counter tops. New LVP flooring on main level and new carpet in lower level. Finished basement with 2 additional bedrooms, and 3/4 bath. New windows 2018, new roof 2017. Enjoy the amazing back yard complete with a 30' above ground 4' deep pool (new sand filter pump and liner 2025), hot tub, large canopied lounge area and beautiful privacy fence with solar lanterns. Lots of summer time fun to be had, schedule your private showing today.

2817 High Point Drive, Davenport

$469,900

3 Beds ⋅ 2 Baths ⋅ 12799329 MLS ⋅ NEW Status

SOLID BRICK RANCH IN SOUGHT-AFTER WEST RIDGE.OFFERS 3 GOOD SIZE BEDROOMS AND 2 FULL BATHS. FULL FINISHED BASEMENT.HARDWOOD FLOORS. UPDATED KITCHEN ANDS BATHS. MOST OF THE WINDOWS REPLACED. EASY TO SHOW.

3110 W Jarvis Avenue, Chicago

$459,000

4 Beds ⋅ 6 Baths ⋅ 12747821 MLS ⋅ NEW Status

LIVE HERE. WORK HERE. OWN THE CORNER. Discover an exceptionally versatile live-work opportunity in a prime Davenport location! Positioned on a highly visible corner at Brady Street and East 46th Street, this C-2 zoned property offers approximately 2,992 square feet on a spacious 0.42-acre lot, with approximately 15,800 vehicles passing daily according to 2025 Iowa DOT traffic data. Currently used as both a family residence and place of business, the property combines comfortable, beautifully updated living space with the visibility, accessibility, and parking needed to operate a business. Recent improvements include a new roof, solar panels, privacy fencing, a fully remodeled kitchen, and remodeled bathrooms. Parking is abundant, with approximately 13 spaces in front and room for up to seven additional vehicles in the rear-potentially accommodating as many as 20 vehicles. The flexible layout and prominent corner location create possibilities for an owner-occupant, entrepreneur, investor, or business owner. Imagine operating an office, salon, studio, boutique, professional service, or other permissible business while enjoying the convenience of living on-site. Whether you envision a live-work property, business headquarters, investment property, or an entirely new concept, this property provides the space and visibility to bring that vision to life. Prime location. High traffic visibility. Extensive parking. Beautiful updates. Endless potential. Buyer and buyer's agent to independently verify zoning, permitted uses, residential occupancy, parking capacity, solar system information, measurements, and all property information with the appropriate authorities and professionals.

4537 N Brady Street, Davenport

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North Side Homes for Sale

Newest North Side Homes for Sale

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