Quick Chicago IL MLS Search

Browse All Chicago IL 5 Bedroom Properties for Sale

$350,000
5 Beds ⋅ 3 Baths ⋅ 12756455 MLS ⋅ PENDING Status

4953 S Michigan Avenue Unit #7, Chicago
$499,900
5 Beds ⋅ 2 Baths ⋅ 12753730 MLS ⋅ NEW Status
Fully occupied, renovated brick 2-flat with strong rental income and modern finishes. Each unit features open-concept layout, exposed brick accents, exposed ductwork, recessed lighting, updated kitchens and baths, in-unit laundry, and thoughtful design details throughout. Unit 1 is a 2 bed / 1 bath and Unit 2 is a 3 bed / 1 bath, providing a desirable rental mix for investors or future owner-occupants. Recent major renovation included updated kitchens, baths, mechanicals, electrical, plumbing, windows, exterior doors, concrete, and garage. The property features an unfinished walkout basement, fully fenced backyard, two rear open decks, and a detached 2-car garage. Property is currently tenant-occupied with existing leases in place. Convenient location near the Ogden/Cermak corridor with access to CTA Pink Line transportation, neighborhood retail, parks, restaurants, and major roadways. A turnkey multi-unit opportunity with modern finishes, garage parking, outdoor space, and immediate rental income. The property also features a full unfinished walkout basement, fully fenced backyard, two rear open decks, and a detached 2-car garage.

2103 S Christiana Avenue, Chicago
$1,500,000
5 Beds ⋅ 4 Baths ⋅ 12727324 MLS ⋅ CONTINGENT Status
***SOLD BEFORE PRINT***

1769 W Olive Avenue, Chicago
$650,000
5 Beds ⋅ 4 Baths ⋅ 12755646 MLS ⋅ NEW Status
WHY BUY ONE LIVING SPACE WHEN YOU CAN HAVE TWO? BRAND-NEW CONSTRUCTION WOODLAWN DUPLEX designed for luxury living, house hacking, and income potential! Live upstairs and let the garden unit help reduce your mortgage-or maximize the property's rental potential in one of Woodlawn's most exciting locations. UNIT 1 offers 3 spacious bedrooms and 2.5 baths with HARDWOOD FLOORS THROUGHOUT. Enjoy an impressive overly sized open layout with quartz countertops, waterfall island, custom wet bar with glass rinser, fireplace, smart toilets, and high-end washer and dryer per unit. The spacious primary suite features its own private bath with double vanities. The GARDEN UNIT features 2 bedrooms and 1 bath with its own open modern open kitchen, living area, and high end washer/dryer in unit. Ideal for long-term rental income, extended family, or potential short-term rental use where permitted. Short-term rentals in the surrounding area can command strong rates, with demand supported by nearby attractions and institutions. LOCATION MATTERS! Minutes from the OBAMA PRESIDENTIAL CENTER, University of Chicago, Jackson Park, Museum of Science and Industry, Hyde Park, the lakefront, and convenient transportation. More upgrades include SOLAR PANELS that you ACTUALLY OWN to help reduce utility expenses, tankless hot water, a HUGE REAR DECK built for entertaining, and a BRAND-NEW 2-CAR GARAGE. NEW CONSTRUCTION. TWO LIVING SPACES. INCOME POTENTIAL. PRIME WOODLAWN LOCATION. GRANTS ASSISTANCE MAY BE AVAILABLE for qualified buyers. Schedule your private showing today!

6547 S Evans Avenue, Chicago
$384,900
5 Beds ⋅ 3 Baths ⋅ 12756587 MLS ⋅ NEW Status
Step into this beautifully remodeled home and be greeted by a stunning accent wall and refinished hardwood floors. The main level features three bedrooms, a full bathroom, and a completely remodeled kitchen. Upstairs, the spacious attic boasts beautiful cathedral ceilings and offers the perfect setting for a primary bedroom. The additional room can be converted into a walk-in closet, nursery, or extra storage space.The fully finished basement includes a family room, laundry area, and an additional room that can be used as an office, guest room, or flex space. Additional features include two furnaces, two central air-conditioning systems, a two-car garage, and a generously sized yard.Situated in a highly sought-after area, this home is conveniently located near shopping, dining, and transportation.

3531 W 73Rd Place, Chicago
$1,775,000
5 Beds ⋅ 5 Baths ⋅ 12756258 MLS ⋅ NEW Status
Premier new construction boutique elevator building overlooking Eckhart Park with sprawling 4200 sf floor plan all on one level making it an amazing single family home alternative. Residence 401 is the best unit in the building with an unprecedented 53 ft width, sunny southern and eastern exposure with dramatic skyline views, ideal corner unit layout with 4 bedroom + den + family room, 4.5 bathrooms and panoramic green views of the park with protected views of the Chicago skyline. Incredibly spacious living area with wide plank flooring, floor-to-ceiling windows, and feature wall with gas fireplace. High end chef's kitchen with custom full height cabinetry, top of the line integrated appliances including SubZero and Miele, a wine fridge plus two additional fridge drawers, quartz countertops & full height backsplash, and a plethora of storage including a walk-in pantry. Secondary family room with wet bar and beverage center. 4 generously sized en-suite bedrooms each separated for privacy plus an additional den with french doors perfect for home office or gym. Substantial primary suite with large walk-in closet, and spa-like bathroom with heated floors, water closet, oversized shower, and separate soaking tub. Full laundry room with side-by-side W/D and sink. This home boasts three sizable outdoor terraces with wood tile and synthetic turf. One parking spot included in the price. Second adjacent spot must be purchased with the unit. Hot Noble Square/West Town neighborhood, conveniently located minutes from downtown with Michelin Star restaurants, boutiques, and cafes within walking distance yet tucked away on a quiet tree lined street facing the park.

1340 W Chestnut Street Unit #401, Chicago
$339,900
5 Beds ⋅ 2 Baths ⋅ 12756062 MLS ⋅ NEW Status
Beautifully remodeled brick bungalow. Welcome to this beautiful, recently remodeled brick bungalow offering seven bedrooms across three levels, along with spacious and versatile living areas. The main floor features three bedrooms, a comfortable living room, and formal dining room, perfect for everyday living and entertaining. The finished attic provides two additional bedrooms, offering excellent flexibility for guests, a home office, or extended family. The finished basement includes two more bedrooms, a spacious family room, a full bathroom, and a convenient summer kitchen, creating an ideal additional living space. Additional features include an enclosed porch, mostly new windows, and a two-car brick garage with a new roof. With its classic brick exterior, updated features, generous bedroom count, and multiple living spaces, this home offers both character and functionality for a growing or extended family.

6318 S Fairfield Avenue, Chicago
$549,900
5 Beds ⋅ 3 Baths ⋅ 12755567 MLS ⋅ NEW 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 three city lots, 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 each side, 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
$1,749,000
5 Beds ⋅ 4 Baths ⋅ 12752641 MLS ⋅ NEW Status
Turning onto this single block of North Fairfield, you immediately sense a visual change and a hush. Capped at both ends, this street feels like a hidden architectural enclave, a perfectly preserved stretch of classic Chicago jumbo bungalows sitting on rare, wide, deep lots. At 4929 North Fairfield, that sense of sanctuary carries right inside. Much of the original vintage character remains on the main level, where classic architectural details set a warm, welcoming tone. Upstairs, the roof was raised to create a full, sunlit second floor that expands the footprint while filling the home with natural light. Downstairs, an excavated basement creates true living spaces below, ideal for extended recreation or additional entertaining options. Combining grand modern square footage with a massive private yard, this property offers a rare combination of space, character, and room to write your own chapter. A detailed list of improvements and construction will be provided to interested parties.

4929 N Fairfield Avenue, Chicago
$379,000
5 Beds ⋅ 3 Baths ⋅ 12755295 MLS ⋅ NEW Status
What is it about this area? Lake Michigan is minutes away, and so is everything built around it. Rainbow Beach, the South Shore Cultural Center, 2 golf courses, and the lakefront harbors. The Obama Presidential Center just opened in Jackson Park in 2026, and reinvestment is visible up and down these blocks. Also roughly 35 minutes to the Loop by train, 20-30 by car. First thing the notice is the extra-wide lot you are sitting on. Walking into 6 bedrooms, 3 full baths. This 1915 brick bungalow was taken down to the studs and rebuilt in 2026, not a lipstick flip. The main level gives you 3 bedrooms, large spanning windows in the living room, you'll get tht factor upon entering, a separate dining room, and a brand-new kitchen with white shaker cabinets, quartz counters, stainless appliances, and a walk-in pantry. The new second level adds 2 more bedrooms off a stairway that makes a real first impression. Downstairs, the finished basement handles everything else: rec room, 6th bedroom, another full bath, laundry, storage. New central A/C, luxury flooring throughout, rear deck, white picket fence, 2-car detached garage..more.

7948 S Colfax Avenue, Chicago
$85,000
5 Beds ⋅ 3 Baths ⋅ 12755683 MLS ⋅ NEW Status
Investment by opportunity in North Lawndale!! 2 Unit With a 2 story Coach house in the back!!! Two properties for the price of one! Building is ready for the next savvy investor! Commercial storefront, apartment unit on top, and separated coach house in the back! Endless possibilities!! NEW CONTRUCTION ALL AROUND THIS SECTION OF THE CITY! Schedule your showing today!

1304 S Karlov Avenue, Chicago
$159,900
5 Beds ⋅ 2 Baths ⋅ 12755439 MLS ⋅ NEW Status
Solid brick and stone 2-flat located in the West Garfield Park neighborhood. This property offers a total of 5 bedrooms and 2 bathrooms, providing spacious living arrangements across both units. Features include a full finished basement offering additional living or storage space and classic architectural details throughout. Property is being sold in AS IS condition, no surveys nor disclosures, taxes prorated. Excellent investment opportunity or rehab project with great potential. Conveniently located near schools, parks, public transportation and major expressways. SEE ATTACHED CITY OF CHICAGO LIST OF BUILDING VIOLATIONS Subject to prior offer cancellation.

925 S Springfield Avenue, Chicago
$1,995,000
5 Beds ⋅ 4 Baths ⋅ 12709204 MLS ⋅ NEW Status
Tucked into a quiet, coveted pocket of Lincoln Park, this exceptional single-family residence pairs architectural pedigree with a level of craftsmanship rarely found on the market. Five bedrooms, three full and one half bath, and a floor plan engineered for real life - four bedrooms conveniently on one level - set the stage for a home that feels as good to live in as it looks. Light pours through the front living room, where custom sheers, gallery-style art lighting, hand-detailed crown molding, and rich hardwood floors set an unmistakably elegant tone. At the heart of it all: a chef's kitchen outfitted with a curated suite of Bosch, Viking, KitchenAid, GE and Sub-Zero appliances, custom Valcucine cabinetry, and sleek stainless countertops - as beautiful as it is built to perform. The kitchen flows effortlessly into a sun-washed breakfast nook with custom banquette seating and a family room anchored by a dual-sided wood-burning fireplace, framed by a wall of Marvin French doors. Beyond those doors, an outdoor retreat awaits: built-in gas lines for grilling, a Solus fire pit, and fully landscaped, furnished living spaces that erase the line between indoors and out. Above it all, a sprawling rooftop terrace with a six-person hot tub delivers the kind of setting that turns ordinary evenings into occasions. Upstairs, the primary suite is a genuine retreat - a run of custom closets, a spa-caliber bath with dual vanities, a soaking tub, a glass-enclosed shower, and a new bidet toilet. Three additional bedrooms (one currently serving as a home office), a well-appointed hall bath, and bedroom-level laundry with a new Bosch washer/dryer complete this floor. The fully finished lower level is built for both productivity and play: a second family room with a custom workstation, a wet bar with wine fridge, and a versatile fifth bedroom with built-in shelving - ideal for guests, an au pair, or in-laws. A second laundry room with dual units, a sink, and an additional refrigerator round out this exceptional level. The details continue: a heated two-car garage with EV charging (2021) and custom organization, a mud room, skylights throughout, a heated slate foyer and walkway, and a full security system with cameras - every inch considered, every update intentional. (Full upgrade list available upon request.) Just steps from St. Alphonsus and Lincoln Park's celebrated dining scene, with Wrightwood Park and Jonquil Park moments away and the city's best shopping and culture within easy reach - this is Lincoln Park living, elevated.

2452 N Janssen Avenue, Chicago
$599,900
5 Beds ⋅ 3 Baths ⋅ 12755079 MLS ⋅ NEW Status
JEFFERSON PARK GEM WITH A BACKYARD RETREAT LIKE NO OTHER! Meticulously maintained and exceptionally inviting, this charming 2 flat, within walking distance to Jefferson Park station, offers spacious living and dining rooms, beautiful hardwood floors, a newer kitchen, a 2nd floor rental unit and a fully finished basement ideal for extended family, guests, recreation, or additional living space. But the true heart of this home is the extraordinary two-level rear deck. Directly connected to the house and accessible from both the first and second levels, this expansive outdoor living space is an entertainer's dream. A covered gazebo, mature grapevines, warm wood decking, and a built-in hot tub create a private backyard oasis that feels more like a destination than an ordinary city backyard. It's the perfect setting for summer gatherings, quiet evenings, morning coffee, or relaxing in the hot tub surrounded by greenery. The oversized, fully fenced yard provides exceptional privacy and additional space for entertaining, gardening, or enjoying the outdoors. This is more than a very nice Jefferson Park home-it is a home with a truly special outdoor lifestyle.

5128 W Ainslie Street, Chicago
$1,450,000
5 Beds ⋅ 5 Baths ⋅ 12753041 MLS ⋅ NEW Status
Rare West Town/East Village offering combining the perfect bland of scale, architecture, design and outdoor living. This exceptional 4,000 Sq Ft, 5 bed, 4.5-bath home spans four finished levels and pairs soaring high ceilings, two primary suite options, a private south facing roof deck with postcard worthy skyline views, a fenced backyard, multiple outdoor entertaining spaces and an attached 2-car (tandem) garage. Extensively upgraded and impeccably maintained, this is sophisticated city living with room to spread out. From the moment you enter, the home reveals a thoughtful balance of architectural volume and refined, transitional design. White oak floors, modern tile, custom wall coverings, designer window treatments, upgraded lighting and organized closets create a cohesive and polished aesthetic throughout. The main level welcomes you with a gracious foyer and an abundance of storage before unfolding to a spacious in-law suite with a full bath. The suite opens out to the fenced backyard, recently refreshed with brand new artificial turf. An attached 2-car tandem garage w/ lofted storage completes this level. The 2nd floor is the architectural centerpiece, where 14' ceilings and southern exposure fill the expansive living spaces with natural light and frame tranquil views of tree-lined Superior St. The beautifully renovated kitchen combines crisp white & navy cabinetry with quartz countertops, a farmhouse sink, second prep sink, subway tile backsplash, new breakfast bar, upgraded plumbing fixtures, warming drawer, wet bar and pantry. The kitchen flows effortlessly into the oversized open-concept living and dining room, anchored by a new stone-surround fireplace and illuminated by soaring ceilings and double Juliet balconies. Just beyond, the rear deck extends the living space to the outdoors, creating an ideal setting for al fresco dining, grilling and entertaining. A sophisticated powder room featuring brass fixtures and chic designer wall coverings completes the level. Heading up, the 3rd floor introduces two generous guest bedrooms each with a walk-in closet, plus a hall bath and dedicated laundry room. The first of two primary suite possibilities offers an expansive walk-in closet and updated ensuite bath featuring a new vanity/ lighting, shower and Jacuzzi tub. At the top level, vaulted ceilings create a dramatic sense of volume and an entirely different experience. Use this exceptional space as a second oversized primary suite, family room, media lounge, home office, guest retreat or a combination of them all. The space opens directly to the private South facing roof deck, recently rebuilt (2023) and enhanced with new Trex decking. Here spectacular Chicago skyline views create the quintessential urban backdrop. A luxurious full bath with dual new vanities, updated shower and Jacuzzi tub, along with an XL walk-in closet, complete this level. THOUGHTFULLY INVESTED & BEAUTIFULLY MAINTAINED, recent improvements reflect a significant commitment to comfort and long-term ownership: 2026: New storm doors, new backyard turf, laundry moved to the third floor and venting completely rebuilt through the home. 2025: New LG front-load washer and dryer (both Wi-Fi enabled). 2023: Balcony roof completely rebuilt, Entire first floor fully re-tiled, including hallway and bedroom. New hot water heater, New Carrier 5-speed 16 SEER air conditioner/heat pump, New Carrier 96% efficient, two-stage 120,000 BTU furnace. 2022: New tear-off roof, Approx 350 SF of deteriorated plywood replaced, GAF FeltBuster Synthetic Roofing Felt, Grace Ice & Water Shield installed along roof perimeter, New drip edge & metal flashing as needed, and New GAF Timberline 30 yr architectural shingle roof. All of this and more set on a quiet tree-lined street- this home offers a rare combo of residential tranquility & neighborhood energy. Chicago Ave's acclaimed restaurants, cafes, boutiques, nightlife and everyday conveniences are just steps away.

1856 W Superior Street, Chicago
$800,000
5 Beds ⋅ 2 Baths ⋅ 12706507 MLS ⋅ NEW Status
One family has loved and occupied this home for nearly 100 years. Now, it's ready for reinvention. Located on a serene one-way block in historic Edgewater Glen AND in Pierce Elementary! The wide, long lot means each unit is large and has fantastic natural light. First floor is 2/1. Second floor 3/1. Full unfinished basement has nearly 8' ceilings. The home's original built-ins, millwork, doors and hardwood floors have been preserved, throughout. Incredibly well-maintained with replacement windows throughout, 2015 boiler, 2022 water heater, 2024 fully tuckpointed, newer 2.5 car garage and more! First floor kitchen does not have a refrigerator or finish flooring, so cash or portfolio lender for purchase is recommended. Sold "as is". This block of Granville is NOT within the boundaries of the Edgewater Glen Historic District so may be renovated without restriction.

1515 W Granville Avenue, Chicago
$1,350,000
5 Beds ⋅ 4 Baths ⋅ 12753253 MLS ⋅ NEW Status
Set on a picturesque, tree-lined street in the sought-after Audubon School District, this beautifully appointed five-bedroom, 3.1-bath Roscoe Village residence delivers exceptional space, timeless character, and an effortless indoor-outdoor lifestyle. An elegant living room with a tray ceiling flows into the formal dining room, while rich hardwood floors, crown molding, custom millwork, and a striking iron-and-wood staircase add architectural distinction throughout. At the rear of the home, the expansive eat-in kitchen has been elevated with Taj Mahal quartzite countertops and backsplash, refinished maple cabinetry, updated hardware, stainless steel appliances, and a double-oven range. The kitchen opens seamlessly to an inviting family room anchored by a beautifully retiled fireplace, creating a sophisticated yet comfortable setting for everyday living and entertaining. French doors extend the space onto a large, sun-filled deck ideal for al fresco dining and relaxed summer gatherings. Three bedrooms occupy the upper level, including a serene primary retreat with soaring vaulted ceilings, skylights, a sleek linear gas fireplace, and a private balcony overlooking the backyard. The fully renovated primary bath offers a spa-like escape with a marble shower, soaking tub, heated porcelain tile floors, dual vanities, and refined lighting. Custom closet organizers, room-darkening shades, and refreshed flooring further enhance the home's comfort and functionality. The finished lower level provides exceptional flexibility with a spacious recreation room, two additional bedrooms, a full bath, and a convenient mudroom. Meticulously maintained and thoughtfully improved, the home also features updated patio doors, newer laundry appliances and water heater, an electric sump pump, recent masonry and tuckpointing, and updated HVAC systems. Complete with three fireplaces, multiple outdoor spaces, and a 2.5-car garage, this sophisticated residence offers gracious city living moments from the acclaimed dining, boutiques, and cafes along Roscoe Street, St. Benedict, the Paulina Brown Line, and near Hamlin Park.

3242 N Leavitt Street, Chicago
$1,895,000
5 Beds ⋅ 3 Baths ⋅ 12728602 MLS ⋅ NEW Status
Don't miss this exceptional single-level completely updated luxury residence of approx. 3500 sq ft in a boutique elevator building with LOW assessments, perfectly situated in the heart of highly desirable East Lakeview! This gorgeous 5-bedroom, 3-bathroom home beautifully blends vintage character and timeless elegance with the modern updates and conveniences you've been looking for. A gracious and welcoming foyer opens to the stunning living room, where oversized windows fill the space with natural light, soaring ceilings add to the sense of grandeur, and a handsome gas fireplace creates a warm and inviting focal point. The living room flows seamlessly into the elegant dining room, featuring beautiful moldings and rich hardwood floors-perfect for both sophisticated entertaining and comfortable everyday living. The large, updated chef's kitchen is designed for both cooking and gathering, with a generous center island, new countertops, stainless steel appliances, abundant cabinetry, and exceptional workspace. Adjacent to the kitchen, the charming breakfast room features new built-ins and plenty of room for a table, creating the perfect spot for morning coffee or casual meals. The spacious bedrooms offer wonderful flexibility, including a fabulous primary suite with direct access to your private balcony, excellent closet space, and a beautifully updated en-suite bath featuring a relaxing soaking tub, separate shower, double vanity, and generous storage. Three additional bedrooms-one currently enjoyed as a TV room/den-share an updated hall bath, while a private second en-suite bedroom offers your guests their own comfortable retreat. A versatile lower-level bonus room provides even more living space and can easily serve as a home gym, office, workspace, playroom, or whatever best suits your lifestyle. Additional highlights include central air, in-unit laundry, an extra storage closet in the lower level, one garage parking space, one exterior parking space, and shared outdoor space for dining, entertaining, and relaxing. High ceilings throughout, updated windows, central air, in-unit laundry - All the updates and conveniences you are looking for...And the location is truly fantastic! Step outside and you're just moments from the wonderful boutiques, cafes, and restaurants along Broadway. Walk to everything-the lake, Belmont Harbor, lakefront bike path, shopping, casual and fine dining, coffee shops, gyms, Wrigley Field, and all major grocery stores. Enjoy an easy commute with the express bus to downtown at Belmont and the Red Line just a short walk away. Located in the Nettelhorst School District. Beautifully appointed, incredibly spacious, wonderfully flexible, and in one of Chicago's most coveted neighborhoods. Love where you live!

443 W Aldine Street Unit #3, Chicago
$824,900
5 Beds ⋅ 4 Baths ⋅ 12754237 MLS ⋅ NEW Status
Rarely available and beautifully renovated from top to bottom within the last five years, this exceptional five bedroom offering provides the perfect blend of timeless character and contemporary, steps from all the energy and convenience of Division. Situated on one of the neighborhood's most picturesque tree-lined streets, this unique residence boats abundant natural light, and an expansive open-concept layout designed for effortless everyday living and entertaining. The heart of the home is the designer chef's kitchen, appointed with sleek modern cabinetry, quartz countertops, a striking tile backsplash, premium stainless steel appliances and an island. Kitchen flows seamlessly into the light and bright family room with soaring ceilings! Enjoy your private backyard retreat. Please find the primary suite on the second level featuring oversized windows, and a spa-inspired ensuite bath with dual vanities, a steam shower, soaking tub, and designer finishes. An additional spacious bedroom and full bathroom complete the second floor. Three bedrooms and another beautifully appointed full bathroom providing exceptional flexibility on the top floor! Ideally located in one of Chicago's most desirable neighborhoods, you'll enjoy an unbeatable walkable lifestyle just steps from the acclaimed restaurants, cafes, boutiques, and nightlife along Division Street and Chicago Avenue. Nearby parks, neighborhood festivals, public art, and convenient access to the CTA Blue Line, bus routes, and downtown make Ukrainian Village one of the city's most vibrant and connected communities. This is a rare opportunity to own a move-in-ready gem at an affordable price.

2534 W Haddon Avenue, Chicago
$579,900
5 Beds ⋅ 3 Baths ⋅ 12754676 MLS ⋅ NEW Status
What a yard! Gorgeous frame 2 unit spanning 2 lots in Jefferson Park side of Portage Park Chicago. Fully enclosed, this double lot has mature landscaping, an oversized garage, raised patio and additional storage shed. It doesn't lack hang out space nor growing space! This 2 unit has a partially finished basement with a bedroom/bar setup and full bath. The attic is unfinished with further expansion potential. The second floor has central heat and air with a brand new condenser and updated fridge. It features all hardwood, original hutch and high ceilings. Most of the windows have been updated in the last 15 - 20 yrs. Roof estimated 10-15yrs old. The 1st floor is boiler heated with 2 large bedrooms and a big kitchen with back sunroom. This unit is in need of some TLC. Unit 1 and garden are vacant and ready while 2nd floor's lease ends in Feb. 28th 2027. Great location by greenspace, walk to the Metra, bus and Jeff Park Blue line transit center and just 2 blocks from Jewel, great dive bars, Starbucks, Prussing Elementary, great Pilipino and Polish restaurants.. ALL within a 5 minute walk...

5753 W Giddings Street, Chicago
$68,000
5 Beds ⋅ 4 Baths ⋅ 12754472 MLS ⋅ NEW Status
ATTENTION REHABBERS/INVESTORS!! - Full gut rehab - 2 story, 4 units with basement ready for rehab - Property sold in completed "as-is" condition - Seller makes no repairs or offers any repair credits. NO SURVEY, NO TERMITE PROVIDED BY SELLER - CONVEYED WITH SPECIAL WARRANTY DEED AND TAX PRORATIONS AT 100%. PLEASE SUBMIT ALL OFFERS IN WRITING WITH PROOF OF FUNDS AND SIGNED BUYER DISCLOSURES. NO THIRD PARTY INVESTORS/OR WHOLESALE CONTRACTS

7300 S Peoria Street, Chicago
$335,000
5 Beds ⋅ 3 Baths ⋅ 12754448 MLS ⋅ NEW Status
This beautiful brick two unit offers two completely separate living spaces. First floor unit has two beds, one bath. Second floor unit offers three beds and one bath. Spacious attic bedroom features its own half bath! This property also has separate utility bills, two hot water tanks, and two parking spaces. Close to public transportation, great layout, tenants on both units are MTM. *SHOWINGS ONLY ON WEDNESDAYS 12PM-2PM & SATURDAYS 1PM-3PM*

2722 S Homan Avenue, Chicago
$79,900
5 Beds ⋅ 2 Baths ⋅ 12747640 MLS ⋅ NEW Status
Exceptional Investment Opportunity in Auburn Gresham Priced at just $79,900-approximately $91 per square foot-this 5-bedroom, 2-bathroom home at 8332 S. Kerfoot Avenue offers outstanding value and exciting possibilities in Chicago's Auburn Gresham neighborhood. Offered in as-is condition, the property provides a fantastic opportunity for investors or buyers ready to renovate and bring their vision to life. Its generous bedroom count and flexible layout make it an excellent candidate for resale, rental income, or a customized transformation. Recently renovated five-bedroom single-family homes in the 60620 area have sold for an average of approximately $341,500, highlighting the potential value a well-executed renovation may create. At only $79,900, this is a compelling opportunity to acquire a Chicago property at a highly competitive price. Bring your vision and schedule your showing today-opportunities with this combination of price, space, and potential don't come around often. Property is being sold in as-is condition. The estimated ARV is based on nearby renovated sales and is not a guarantee of future value. Buyers should independently verify property details, renovation costs, and resale potential

8332 S Kerfoot Avenue, Chicago
$300,000
5 Beds ⋅ 2 Baths ⋅ 12751313 MLS ⋅ NEW Status

7927 S Parnell Avenue, Chicago
$144,900
5 Beds ⋅ 2 Baths ⋅ 12754196 MLS ⋅ NEW Status
Investor Special / Value-Add Opportunity! 5-bed, 2-bath all-brick 2-story home with a 3-car garage and side driveway, a rare find in Chicago. The property needs renovation but offers a strong opportunity for investors or buyers looking to build equity. Partially finished basement provides additional space and potential for an in-law suite/garden unit, subject to buyer due diligence and approvals. With an estimated ARV of approximately $300,000, this property is ideal for a flip, rental, or owner-occupant looking for a starter home with upside!

8443 S Manistee Avenue, Chicago
$1,250,000
5 Beds ⋅ 4 Baths ⋅ 12754178 MLS ⋅ NEW Status
Stately, all brick 2012 built home with the perfect blend of sophisticated design and modern finishes. This home was updated in 2024 and features an extra wide footprint, front fenced yard and attached garage - features hard to find in the City! Enjoy 5 bedrooms, 3 1/2 baths and 2 living rooms; three levels of beautifully finished living space (all above grade). 2 impressive outdoor spaces! A private fenced front yard and an impressive 900-square-foot rooftop deck designed for entertaining and outdoor living. The main level showcases a bright, open-concept floor plan with tall ceilings, oversized windows, and seamless flow between the living, dining, and kitchen spaces. The spacious living area is ideal for both everyday living and entertaining, while the dedicated dining space comfortably accommodates large gatherings. At the heart of the home is a stunning chef's kitchen featuring high-end Bosch appliances, Sub-Zero fridge, custom cabinetry, quartz countertops, abundant storage and an oversized island. A powder room, pantry and coat closet complete the thoughtfully designed first floor. The second level offers three generously sized bedrooms, two beautifully appointed bathrooms, and a versatile family room or lounge area-perfect for movie nights, a playroom, or a second living space. The luxurious primary suite provides a true retreat with a gas fireplace, two large walk-in closets, and a spa-inspired en-suite bath featuring a double vanity, soaking tub, oversized walk-in shower and private water closet. An additional bedroom on this level offers flexibility for guests, a home office or fitness room. Located in on a perfectly tucked away lot, this home is close to everything Andersonville and Edgewater have to offer while offering privacy. Minutes from the new Ridge Metra Station, the CTA Red Line, the lakefront, and Andersonville's acclaimed restaurants, cafes, boutiques, Gethsemane and neighborhood favorites. This remarkable home delivers the perfect combination of luxury, convenience, space and lifestyle in one of Chicago's most desirable neighborhoods.

5954 N Paulina Street, Chicago
$2,099,988
5 Beds ⋅ 6 Baths ⋅ 12753914 MLS ⋅ NEW Status
Welcome to this stunning corner lot home on a beautiful tree lined street, perfectly located in NORTH-CENTER and the Coonley School District. THIS GORGEOUS Sun Drenched Five-Bedroom, Four full and Two half luxury baths. Superior construction by a very experienced home builder in 2020 with great attention to quality and detail. Step into the Foyer that leads exquisite living with an open and airy living room with a cozy fireplace and dining room, to the well appointed custom kitchen with Amish Cabinetry, Wolf and Sub-zero commercial grade appliances a wet bar and walk-in pantry. The Great Room features custom built-ins, fireplace and dramatic floor to ceiling windows leading to your private rear yard along with a built in exterior grill and exterior wood-burning fireplace. The garage rooftop deck includes a lighted Covered Pergola for all of your exterior entertaining. The Second floor boasts an expansive Primary Suite, dual walk in closets, a luxurious bath, with steam steam shower and separate oversized soaking tub. There's also two spacious ensuite bedrooms along with separate laundry room. The expansive lower level features radiant heat throughout. A large recreation room with wet bar continues your family retreat. The ensuite fourth bedroom is perfect for your guests and bedroom five could doubles as a home office or gym. This home is a distinctive Hardie Board home with designer finishes throughout. Every Detail has been well thought out, steps away from Coonley School, Wells Park, Great Restaurants, Shopping, and Public Transportation - 4100 N Oakley welcomes you home!

4100 N Oakley Avenue, Chicago
$1,275,000
5 Beds ⋅ 4 Baths ⋅ 12721216 MLS ⋅ NEW Status
Stunning 2022 new construction on an extra-wide and landscaped, lush lot with five bedrooms plus den, three and a half baths, and nearly 4,000 finished square feet across three levels, with a rare four bedrooms up. Behind the board-and-batten and brick facade, black windows, and covered front porch is a house that was finished with real intent, not builder defaults. The main level runs front to back, sight-lines from the living room straight through to the family room and its gas fireplace, set in a shiplap surround under a solid white oak mantel. Because the house clears the homes on either side, the main level draws natural light from every exposure throughout the day. Formal dining wall accents, refined millwork, and a chef's kitchen built for real cooking: two-tone custom cabinetry, waterfall quartz island with seating, gloss patterned tile backsplash, undercabinet lighting, double wall ovens, gas cooktop under a stainless hood, breakfast nook, walk-in pantry, and a separate butler's pantry with its own prep sink. A powder room with patterned tile accent wall and black hex floor serves guests, and a rear mudroom with oak bench, cubbies, and hooks opens to the patio, the detail that earns its keep every winter. Upstairs, the primary suite is a serene retreat featuring a vaulted ceiling with exposed white oak beams, walk-in closet, and a spa-inspired bath with full-height porcelain slab walls, soaking tub, double vanity with quartz, marble-look tile floor, and an oversized frameless glass shower with rainhead and handheld. Three more generously sized bedrooms look out into the treetops, and a dual-vanity full bath and true second-floor laundry room with cabinetry, quartz-topped utility sink, and patterned cement tile complete the level. The finished lower level lives like a second home: a recreation room with linear gas fireplace and tray ceiling, wet bar with espresso cabinetry, quartz counter and wine fridge, office with French doors, and a fifth bedroom with full bath and glass shower, currently set up as a private gym, with a walk-in closet large enough to hold a treadmill. Generous windows along the rear keep the whole level bright. Outside, a fully fenced yard with paver patio sized for both a dining table and a lounge group, low-maintenance turf lawn, and planted borders. A full concrete side walk runs the length of the house past a deep bed of roses and ornamental grasses, and the detached two-car garage is sided, roofed, and lit to match the house. White oak floors, black hardware, and custom shades throughout. Close to the Metra, the Forest Preserves, bike trails, and Sauganash shops.

6224 N Keystone Avenue, Chicago
$1,795,000
5 Beds ⋅ 4 Baths ⋅ 12753514 MLS ⋅ NEW Status
A remarkable designer residence where timeless architecture, exceptional craftsmanship, and sophisticated interiors come together in one of Logan Square's premier locations. Originally built in 2021 and thoughtfully imagined by acclaimed designer London Walder Interior Design, this exceptional five-bedroom, three-and-a-half-bath home offers luxurious finishes, cutting-edge technology, and beautifully curated living spaces throughout. Designed for both everyday living and effortless entertaining, the open-concept main level centers around a stunning chef's kitchen featuring custom cabinetry, an impressive 11-foot waterfall island, hand-picked natural marble countertops, a 48-inch Wolf range, paneled Sub-Zero refrigerator, paneled Thermador dishwasher, open shelving, and a spacious walk-in pantry. The adjoining living room, anchored by a fireplace, opens seamlessly to the home's exceptional outdoor living spaces. The second level offers three spacious bedrooms, including a luxurious primary suite featuring architectural ceiling beams, a generous walk-in closet, and a spa-inspired bath with radiant heated floors. Two additional bedrooms share a beautifully appointed Jack-and-Jill bath. The finished lower level provides exceptional flexibility with a spacious recreation room, wet bar, two additional bedrooms, a full bath, and radiant heated floors, creating the perfect space for entertaining, guests, fitness, or a home office. Outdoor living is equally impressive. The professionally designed backyard features a private entertaining blue stone patio complete with a built-in grilling station, gas fire pit, and multiple seating areas. Above the heated two-car garage, the expansive pergola covered rooftop deck is equipped with gas, water, and electric service, offering endless possibilities for outdoor dining and entertaining. The heated garage also includes a 240-volt EV charging outlet with 40-amp service. Every detail has been thoughtfully considered, from integrated smart home technology and Lutron lighting with automated shades throughout to the gated entry and premium finishes that define every space. Ideally located on one of Logan Square's most desirable residential streets, just moments from Milwaukee Avenue's acclaimed restaurants, neighborhood boutiques, parks, and the Blue Line, this exceptional home offers an elevated lifestyle in one of Chicago's most vibrant neighborhoods.

2657 W Belden Avenue, Chicago
$3,750,000
5 Beds ⋅ 5 Baths ⋅ 12750844 MLS ⋅ NEW Status
A rare and seamless blend of architectural history and sophisticated modern living. Situated on one of the neighborhood's most desirable blocks, this spectacular 5,500 square foot, 5-6 bedroom, 4.5 bathroom greystone has been meticulously renovated for a comfortable contemporary lifestyle while honoring its classic Gold Coast character. The handsome three-story stone exterior is capped by an ornate, original copper pediment and roof cresting - welcoming one to the home's many well-preserved historic details. Inside, the expansive front living room offers an inviting layout with space for multiple seating arrangements, a stately fireplace, and a bright and large view, framing mature trees and beautiful Gold Coast architecture. The dining room features the second of the home's three original fireplaces and easily accommodates large family gatherings and dinner parties. The leaded-glass pocket doors provide an elegant partition between the dining room and the home's kitchen. Bathed in morning light, the expansive chef's kitchen is a triumph of thoughtful design and high-end utility. A thick slab of deeply veined white marble tops the oversized central island, which features comfortable counter seating beneath pendant lighting. The culinary suite is anchored by a 48" Wolf range with dual ovens, a Sub-Zero refrigerator, a Bosch dishwasher, and a dedicated wine and beverage fridge. A large bay window, built-in banquette seating, and custom storage cleverly tucked under the rear staircase ensure this magnificent space is as functional as it is beautiful. Stepping out onto the rear terrace reveals a curated private escape. A custom pergola provides shade, while integrated infrared heaters extend the space's use into the cooler months. Designed for effortless entertaining, this exceptional outdoor sanctuary features dedicated areas for grilling and alfresco dining, alongside a full outdoor living room where a fire table provides an inviting focal point for evening gatherings. Back inside, the grand main staircase provides a masterclass in late 19th-century craftsmanship. Rich hardwood handrails and treads contrast with the crisp white wainscoting and expertly carved newel posts. Cleverly concealing a discreet main-floor powder room, the staircase rises past a stunning original stained-glass window to the home's upper levels. Occupying the entire front portion of the home's second level, the primary suite has a deep-set picture window with leafy street views and two closets. The ensuite primary bathroom features beautiful tilework, an oversized, spa-quality shower, separate soaking tub, and double sinks. A second ensuite bedroom with a balcony and a multi-use family room are also located on this level. The home's third floor thoughtfully accommodates three additional, generously sized bedrooms. The front bedroom with cathedral ceilings and a library wall is accessed by a pass-through 14x10ft bonus room, which can be easily tailored to your lifestyle and needs. Completing this level, the two remaining bedrooms share a classic Jack-and-Jill bathroom. The lower level is home to a large family room, a temperature-controlled glass wine room, a dedicated home gym (bedroom six) with modern bath and shower, and a rear mudroom with laundry. A two-car tandem garage completes the home. 1437 N. Dearborn is a truly exceptional and inviting home not often found in the neighborhood. This is a rare opportunity; located two blocks from Lake Michigan and Lincoln Park, in close proximity to beaches, top-rated schools, seasonal farmers' markets, world-class shopping, and fine dining.

1437 N Dearborn Street, Chicago
$2,850,000
5 Beds ⋅ 5 Baths ⋅ 12753243 MLS ⋅ NEW Status
Style, Substance, & Location offered in this enormous light filled 1/2 floor residence. Stunning skyline views and 2 huge, covered terraces. Residence 5B is a thoughtfully upgraded home with private elevator entry, 5 large suites (3 ensuite baths and 2 with shared jack & jill bath), 2 distinct offices, large family room, separate library area, massive living/dining/kitchen great room all sharing floor to ceiling skyline facing glass. Covered 500 SF terrace (17ft x 30ft) to double your entertainment space all with an incredible view of Willis Tower. Fully appointed kitchen with top-of-the-line appliances and cabinetry. Primary suite with 2 walk-in closets and incredible spa appointed bath. A quiet retreat terrace off the primary suit. Dual HVAC systems offering efficient and balanced climate. Fully appointed with window treatments, timeless wallpaper, integrated sound system, and custom closets throughout the home. This home provides the space and livability of a single-family home in a single-level condo in the most vibrant neighborhood in the city known for its incredible schools, vibrant living, and access to downtown.

6 N Carpenter Street Unit #5B, Chicago
$269,900
5 Beds ⋅ 3 Baths ⋅ 12753037 MLS ⋅ CONTINGENT Status
Welcome to 9236 S. Blackstone Avenue, Chicago! This beautifully renovated 5-bedroom single-family home seamlessly blends modern updates with spacious living. From the moment you step inside, you'll be greeted by a bright open-concept floor plan designed for today's lifestyle, offering the perfect flow for everyday living and effortless entertaining. The home has been completely updated with new plumbing, new electrical, and new flooring, providing peace of mind and a truly move-in-ready experience. The expansive layout offers generous living spaces and versatile bedrooms to accommodate families of all sizes, guests, or a home office. Situated on an oversized double lot, the outdoor space is a rare find in the city. Whether you're hosting summer barbecues, family gatherings, celebrations, or simply enjoying your own private backyard retreat, this property offers endless possibilities for entertaining and recreation. Conveniently located near parks, schools, shopping, public transportation, and major expressways, this exceptional home combines modern comfort, functionality, and incredible outdoor space. Don't miss the opportunity to make this stunning home yours-schedule your private showing today! Drive by today and call to schedule your private tour! Bienvenido a 9236 S. Blackstone Avenue, Chicago! Esta hermosa residencia unifamiliar de 5 recamaras ha sido completamente renovada y combina un diseno moderno con espacios amplios y funcionales. Desde el momento en que cruza la puerta, sera recibido por un concepto abierto que ofrece una excelente distribucion, ideal para la vida diaria y para disfrutar de momentos inolvidables con familiares y amigos. La propiedad ha sido totalmente actualizada, incluyendo plomeria nueva, instalacion electrica nueva y pisos completamente nuevos, brindandole tranquilidad y la comodidad de una casa lista para habitar. Uno de los mayores atractivos de esta propiedad es su amplio terreno doble (double lot), una caracteristica poco comun en la ciudad. Este extraordinario espacio exterior es perfecto para organizar reuniones familiares, parrilladas, fiestas, celebraciones o simplemente disfrutar de un amplio jardin privado con infinitas posibilidades. Ubicada en una zona con facil acceso a parques, escuelas, comercios, transporte publico y principales vias de comunicacion, esta propiedad ofrece la combinacion perfecta entre comodidad, funcionalidad y estilo moderno. No deje pasar esta increible oportunidad de adquirir una casa completamente renovada con un terreno excepcional! Agende su visita privada hoy mismo y descubra todo lo que esta magnifica propiedad tiene para ofrecer. Pase a conocer esta hermosa propiedad y llamenos hoy mismo para programar su cita personalizada! Descubra en persona todo lo que esta casa tiene para ofrecer y permitanos mostrarle cada uno de sus increibles espacios. Sera un placer atenderle!

9236 S Blackstone Avenue, Chicago
$484,900
5 Beds ⋅ 4 Baths ⋅ 12753036 MLS ⋅ NEW Status
Welcome to 1059 N Lorel Avenue-an exceptional, beautifully updated Chicago Victorian Residence offering an impressive amount of living space across multiple finished levels, situated on a highly desirable OVERSIZED CHICAGO LOT. Step inside to a bright and inviting open-concept floor plan featuring beautiful hardwood floors throughout and generous living and entertaining spaces. The main level offers a seamless flow between the living, dining, and kitchen areas, along with a convenient powder room for guests. The second floor features FOUR exceptionally spacious bedrooms, providing outstanding flexibility for family, guests, or home-office space, along with beautifully appointed bathrooms. Continue upstairs to the incredible private attic-level primary suite-a true owner's retreat featuring an en-suite bathroom and walk-in closets, creating a private sanctuary separated from the home's additional bedrooms. The FULL FINISHED BASEMENT provides even more valuable living and entertainment space and is perfectly suited for a HOME THEATER, recreation room, game room, gym, or additional family room. Altogether, the home features 5 spacious bedrooms, 3 full bathrooms + 1 half bathroom, an open floor plan, hardwood flooring, and extensive improvements including updated plumbing, electrical, flooring, and interior finishes. Outside, the oversized Chicago lot provides additional space for outdoor entertaining, recreation, gardening, and enjoying your own private backyard retreat. 5 BEDROOMS * 3.1 BATHS * PRIVATE PRIMARY SUITE * WALK-IN CLOSETS * 4 SECOND-FLOOR BEDROOMS * FULL FINISHED BASEMENT * HARDWOOD FLOORS * OVERSIZED LOT A rare opportunity to enjoy the space of a suburban home with the convenience of Chicago living. Move-in ready and designed to impress-drive-by and call to schedule your private showing today! Pase por la propiedad y llamenos hoy mismo para programar su visita privada! Hablamos Espanol!

1059 N Lorel Avenue, Chicago
$435,000
5 Beds ⋅ 3 Baths ⋅ 12696590 MLS ⋅ NEW Status
2 Flat on a beautiful street in Albany Park! Perfect opportunity to owner occupy with income, or possible rehab to a single family home. Larger unit is a duplex up consisting of a 2 bedrooms on the main floor, family room, dining room, kitchen that leads out to a generous deck. 2nd floor has a large bedroom with ensuite bathroom. Garden/1st floor is a 2 bedroom with family room, proper dining room, workable size kitchen and bath. Interior door leads to a shared laundry room. Great backyard and 2 car garage.

4602 N Karlov Avenue, Chicago
$275,000
5 Beds ⋅ 2 Baths ⋅ 12752678 MLS ⋅ NEW Status
Regular sale offered at $275,000! Recently updated brick two-flat featuring spacious rooms, hardwood flooring throughout and individual heating systems. The first-floor unit is vacant and easy to show. The upper unit offers a generous four-bedroom layout with a modern kitchen and updated ceramic-tile bath. Large enclosed rear porches, a fenced yard with wrought-iron fencing and a rear parking pad for two vehicles complete the property. Convenient access to public transportation. An excellent opportunity for an owner-occupant or investor. Basement is open with laundry hookup. Very large space. 2nd floor has a current tenant.

6322 S Honore Street, Chicago
$295,000
5 Beds ⋅ 3 Baths ⋅ 12752509 MLS ⋅ ACTIVE Status
Price to sell - Beautifully renovated and thoughtfully updated, this spacious home offers six bedrooms, three full bathrooms, and a two-car detached garage. The above-grade living space features five bedrooms and two full bathrooms, while the finished basement provides an additional bedroom, a third full bathroom, and versatile space ideal for recreation, entertaining, a home office, or extended-family living. Extensive improvements include a new HVAC system, new windows, updated electrical and plumbing systems throughout, a new sewer line, and a new sewer backflow-prevention valve. Modern finishes and a functional layout create a comfortable, move-in-ready home with plenty of room to accommodate a variety of lifestyles. Conveniently located in Chicago's Park Manor neighborhood near parks, schools, shopping, restaurants, public transportation, and major expressways. Although fully renovated, the property is being sold AS IS. Inspections are permitted for the buyer's informational purposes and personal satisfaction only. All room sizes, lot dimensions, and measurements are approximate and should be independently verified by the buyer.

7038 S King Drive, Chicago
$636,000
5 Beds ⋅ 4 Baths ⋅ 12752412 MLS ⋅ ACTIVE Status
THE HEART OF BRIDGEPORT, Healy School District. Brick 3-unit, 2 units are 1-bed/1-bath. 2nd floor is 3 bed/2-bath with in-unit laundry, master bedroom has a walk-in closet.New high-efficiency, gas-forced heating furnaces per unit WITHIN 9 YEARS. The roof is 9 years old. A REPLACE ALL NEW WINDOWS IN LESS THAN 7 YEARS.EXTRA Laundry in the basement AND 4 CARS PARKING SPACE AT BACKYARK can generate more income. ALL UNITS EASY RENTED, VERY GOOD CASH FLOW.GREAT QUIET RESIDENTIAL HOUSE IN THE HEART OF CHICAGO WITH BIG PATIO HAS GREAT VISION TO ENJOY BEAUTIFUL DOWNTOWN! PERFECT FOR INVESTMENT OR LIVING IN ONE AND RENTING TWO IN THE HOT BRIDGEPORT.

3041 S Lowe Avenue, Chicago
$1,199,000
5 Beds ⋅ 6 Baths ⋅ 12752105 MLS ⋅ ACTIVE Status
Welcome to this exceptional Greystone vintage 3-unit building offering 5 bedrooms, 5 full bathrooms, and 1 half bathroom, perfectly blending classic Chicago charm with modern comfort. Featuring beautiful landscaping, a fenced backyard, and thoughtfully designed living spaces, this remarkable property presents an outstanding opportunity for both homeowners and investors. A stunning hardwood staircase welcomes you through the main entrance, providing access to both the first- and second-floor units. Let's begin with the second-floor residence. As you enter, you're greeted by a bright and spacious living room, highlighted by a beautiful English skylight lantern above the foyer and oversized windows that fill the home with abundant natural light. Located just off the living room, the primary suite offers a private retreat with a separate sitting area, generous closet space, direct access to a private balcony, and large windows that create a warm and inviting atmosphere. On the opposite side of the living room, the second bedroom features a walk-in closet and ample living space. The unit includes two full bathrooms-one with a luxurious walk-in steam shower and the other with a relaxing soaking tub. Conveniently located between the bedrooms, the dedicated laundry room adds everyday comfort and functionality. Toward the rear of the home, the open-concept family room and kitchen create the perfect gathering space, centered around a cozy fireplace with both gas and wood-burning options. The kitchen is beautifully appointed with stainless steel appliances, a large center island with breakfast bar seating, pantry storage, and expansive windows that surround the space with exceptional natural light. The first-floor unit mirrors the upper-level layout, offering incredible flexibility for multi-generational living or rental income. It features its own fully equipped kitchen, two full bathrooms, a dedicated laundry room, and an added layer of security with alarm sensors installed on every window. From the rear staircase, you'll find access to the basement studio unit. Before entering the studio, you'll pass a spacious recreation room, utility area, and a separate laundry room dedicated exclusively to the lower-level residence. Inside the studio, you'll find a thoughtfully designed living space featuring a full kitchen with stainless steel appliances, a microwave, air fryer, and range hood. The studio also includes one full bathroom, one half bathroom, and generous closet space, creating a comfortable and functional living arrangement that's perfect for guests, extended family, or rental income. The rear staircase also provides convenient access to the rooftop, the first-floor unit, and the second-floor residence, making movement throughout the building both practical and efficient. Designed with long-term comfort and peace of mind, the property is equipped with multiple tankless water heaters, multiple zoned furnaces, multiple sump pumps, and a comprehensive security system, showcasing the exceptional care and quality invested throughout the home. Step outside to enjoy the beautifully landscaped, fenced backyard featuring a brick paver patio, mature landscaping, and multiple outdoor seating areas-an ideal setting for entertaining family and friends or simply relaxing outdoors. Conveniently located near public transportation, bus routes, restaurants, grocery stores, shopping, and everyday conveniences, this exceptional Greystone offers the perfect combination of timeless Chicago architecture, modern functionality, and outstanding investment potential. Don't miss this rare opportunity to own a versatile, meticulously maintained multi-unit property that seamlessly blends historic character, modern upgrades, and exceptional income potential-all in one of Chicago's most desirable neighborhoods.

4448 N Tripp Avenue, Chicago
$850,000
5 Beds ⋅ 3 Baths ⋅ 12704054 MLS ⋅ ACTIVE Status
**Steps from Horner Park and the Chicago River, 4104 N. Richmond offers a rare East Irving Park opportunity with 3 levels of finished living space, 5 bedrooms, 2.5 baths, beautiful vintage hardwood floors, and a flexible layout designed for the way people live today.** The main level features a spacious living room, dining room, powder room, and a bright open kitchen with generous counter space and island seating-creating an easy flow for everyday living and entertaining. A flexible room just off the kitchen can serve as a **5th bedroom, home office, den, playroom, or guest space**. Upstairs, the second level offers **3 bedrooms and a full bath**, while the third floor feels like a private retreat with a bedroom, separate sitting/office area, vaulted ceilings, hardwood floors, and a spacious ensuite bath with a soaking tub and separate shower. Plus the convenience of a 2nd floor laundry access. A major recent improvement adds real value: **the homeowner has invested more than $25,000 in a comprehensive French drain and whole-house drainage system**, providing an important infrastructure upgrade rarely seen at this price point. Because of the extensive drainage work, portions of both the **front and rear yards were recently disturbed and are being resodded**, giving the next owner a fresh start outdoors. And the location is hard to beat. **Horner Park is just moments away**, offering expansive green space, sports fields, playgrounds, walking and biking paths, and access to the Chicago River and canoe launch. Families will appreciate the convenient proximity to **Bateman Elementary, Lane Tech College Prep, and DePaul College Prep**, while commuters enjoy easy access to public transportation and major expressways. Surrounded by **new construction, renovated homes, and continued neighborhood investment**, 4104 N. Richmond delivers something increasingly difficult to find on Chicago's North Side: **space, character, multiple living zones, a private yard, significant recent infrastructure investment, and an outstanding park-and-river location-all in one home.**

4104 N Richmond Street, Chicago
$427,000
5 Beds ⋅ 4 Baths ⋅ 12751858 MLS ⋅ ACTIVE Status
Beautifully updated and luxurious 5-Bed/4-Bth home offering over 4,500 sq ft of finished living space! Recently rehabbed, this stunning home combines sophisticated design with modern comfort and is truly move-in ready. Step inside to an expansive living and dining area featuring an elegant statement wall and coffered ceilings that create an elevated first impression. The gorgeous kitchen is the heart of the home, showcasing crisp white cabinetry, stainless steel appliances and an oversized island with breakfast bar. Two spacious bedrooms and full bath complete the main level. Upstairs, the luxurious Primary Suite offers a private retreat with generous living space, walk-in closets and a beautiful en-suite bath. Two additional bedrooms and another updated full bath provide plenty of space for family and guests. The finished basement expands the living space even further with a large recreation room, custom wet bar and the home's fourth full bath. No detail was overlooked in this comprehensive renovation, with updates including a new roof, windows, A/C, water heater, appliances, plumbing, electrical, ductwork and more. With its high-end finishes, thoughtful layout and impressive amount of living space, this exceptional home offers the perfect blend of luxury, style and functionality. Schedule your private tour today!

7801 S Eberhart Avenue, Chicago
$899,000
5 Beds ⋅ 3 Baths ⋅ 12740416 MLS ⋅ ACTIVE Status
Unique Opportunity in Bucktown to make this your own home. This family estate sale once used as a multi generational home was broken up to accommodate multiple family members and now being sold. There are 5 bedrooms including 1 on the ground level 2 on the 1st and 2 on the 2nd floor. Can easily be converted to a 2 or 3 unit with the block being RT-4 Zoning. This All Brick Structure is in need of renovation but has endless potential! Plus a large back yard and 1.5 car garage which at one time in the past was a coach home. There is a tenant in the lower level of home that will be moving. Steps to the Clybourn Metra station, Damen/Western Blue Line CTA, and minutes to I-90/94. Easy access to the elevated 606 Trail and the swimming pool/sports courts at Holstein Park. Enjoy Bucktown's vibrant lifestyle with renowned dining, craft coffee houses, and boutique retail right outside your door. Bring your contractor and design ideas! The Zoning is RT-4 and single-family conversion potential draws in premium buyers who want custom homes, not just multi-unit investors.Transit Trifecta, Explicitly mentions Clybourn Metra, Blue Line, and Highway access.Bucktown Icons:The 606 Trail and Holstein Park

1946 W Armitage Avenue, Chicago
$863,900
5 Beds ⋅ 4 Baths ⋅ 12749829 MLS ⋅ ACTIVE Status
Welcome home to 6100 N. Mason. This jumbo mission style bungalow located in South Edgebrook, has been meticulously maintained and updated by the current owners. Situated on an oversized corner lot and really shows pride of ownership throughout. This 5 bedroom 3 1/2 bath home is bursting with natural sunlight. The first floor features a large cooks dream updated eat-in kitchen, with 42" custom cherry cabinets, all high end stainless steel appliances, counter top TV, granite countertops, an instant hot and filtered cold water faucet, beautiful tiled backsplash and a breakfast bar. You'll also find a beautifully updated full bath, large living room, separate large dining room and 3 bedrooms. On the second floor you'll find the large primary suite with a spa-like updated full bath, another bedroom, a powder room and a 2nd laundry room with a Bosch W/D. The full walkout basement truly expands your living space with a large family room with a wet bar, a recreation room, a large laundry room, utility/storage/workshop room and a bonus hot tub room. The fully fenced backyard will give so much enjoyment with the large composite deck with a Sunsetter retractable awning, above ground pool, a shed for storage and an extra large brick paver patio. And you won't have to cut the grass in the large back yard. It's low maintenance turf. This is more than just a home. It's a rare opportunity to live in one of Chicago's most desirable communities.

6100 N Mason Avenue, Chicago
$1,200,000
5 Beds ⋅ 5 Baths ⋅ 12644332 MLS ⋅ ACTIVE Status
HOT WEST TOWN Multi-Family 4 Unit Property- separate front brick facade building featuring 2 units plus a garden unit (Non-conforming garden unit-with no representation of legality of garden unit) and a separate rear building offering an additional 2 one bedroom, one bath units with hardwood floors, all units have Individual Space Heat. Coin-Operated Common Area Laundry Facility. Additional room, and water closet in the lower level for the owner's personal use only. Nice deck in yard, 2 rear parking spaces with privacy gate. Immediate income increase by renting the 2 parking spaces. Easy access to public transportation, just steps to the blue line, grocery stores, convenient highway access, popular restaurants, entertainment, and minutes to River West, Fulton Market and downtown. Build your dream home, hold for long term investment, 1031x, offers R3 zoning. Many possibilities.

1542 W Thomas Street, Chicago
$465,000
5 Beds ⋅ 2 Baths ⋅ 12750993 MLS ⋅ CONTINGENT Status
Fantastic Norwood Park Opportunity! Bring your ideas and vision to this spacious 5-bedroom, 2-bath home that has been owned by the same family for over 50 years. Offering great bones and tons of potential, this is the perfect opportunity for buyers looking to renovate, customize, and build equity in a highly desirable neighborhood. Hardwood floors are believed to be under the carpeting on the main level. Additional highlights include flood control and a newer garage built approximately six years ago. Conveniently located near schools, parks, shopping, dining, and public transportation. With some updating and TLC, this longtime family home is ready for its next chapter. Sold As-Is.

5649 N Moody Avenue, Chicago
$675,000
5 Beds ⋅ 4 Baths ⋅ 12750859 MLS ⋅ ACTIVE Status
A beautifully updated brick bungalow, blending timeless charm with thoughtful modern enhancements. Offering 6 bedrooms and 4 full baths, this home features separated living and dining rooms, a beautiful kitchen with stainless steel appliances (refrigerator and oven), induction cooktop, a cozy breakfast nook, a stylish wet bar perfect for entertaining, and a beautifully finished deck ideal for relaxing or hosting gatherings. Plenty of closet space throughout adds comfort and convenience. Modern upgrades elevate the experience: Level 2 Tesla charger, copper water service, smart dimmers, and CAT6 wiring in every room for seamless homeoffice performance. A wholehouse tankless reverseosmosis water filtration system provides purified water for drinking, cooking, and everyday use. The second floor enjoys zoned heating and cooling powered by highefficiency Mitsubishi heat pumps. Entertainment lovers will appreciate the thoughtfully designed hometheater environments: * Living Room: Builtin inwall speakers with Dolby Atmosready wiring supporting multiple configurations (7.1, 5.1.2, 3.1.4). * Basement: Builtin inceiling speakers with Dolby Atmosready wiring for advanced setups (7.1, 7.1.2, 5.1.4, 3.1.4), plus prewiring for a ceilingmounted projector. A layout that blends comfort, technology, and style - a thoughtfully upgraded home ready to be lived and loved.

4334 N Monitor Avenue, Chicago
$129,900
5 Beds ⋅ 2 Baths ⋅ 12747474 MLS ⋅ ACTIVE Status
Located in sought-after Auburn Gresham, this charming Chicago-style bungalow offers an expansive floor plan, incredible space, and plenty of potential for future equity growth. This is a home that truly should not be overlooked! What makes this property especially unique is its generous layout. The finished second floor features 3 bedrooms plus a den, while the main level offers 2 additional bedrooms and a full bath, creating a natural 5-bedroom, 2-bathroom floor plan - a rare find in a Chicago bungalow! Inside, you'll find many of the classic features buyers love, including beautiful hardwood floors, original natural wood trim, and an abundance of windows that fill the home with natural light. The property also includes a 2-car brick garage, adding valuable convenience and functionality. Situated on a great block with numerous renovated homes nearby, this property offers an ideal combination of location, size, and opportunity. Whether you're looking for a spacious home or a property with significant upside potential, this bungalow checks the boxes. Opportunities with this much space and potential don't come around often. Don't miss your chance to see everything this home has to offer - schedule your showing today!

7615 S Carpenter Street, Chicago
$725,000
5 Beds ⋅ 2 Baths ⋅ 12750206 MLS ⋅ ACTIVE Status
Bring your architect and design dreams to this grand vintage mansion, currently a 5 large bedroom (all on the same floor) and 2 bath home. A historic masterpiece, near the United Center, boasting incredible curb appeal and unmatched exterior details.. offering an extraordinary opportunity to restore a true architectural treasure. This sprawling estate nestled on a large, 44 X 125, lot, has soaring ceilings, expansive floor plan, oversized windows, and beautiful vintage details. Some new electrical, plumbing and duct work has been started. Approximate ages of building components: Furnace (3 years), Roof (10 years), and Tuckpointing (12 years).

2050 W Monroe Street, Chicago
$599,000
5 Beds ⋅ 3 Baths ⋅ 12751156 MLS ⋅ CONTINGENT Status
Classic yellow-brick, legal three-flat in Portage Park, situated on an oversized 31' x 125' lot. All three units are currently rented and occupied. The first- and second-floor units feature gorgeous original woodwork and detailing, along with two-bedroom, one-bath layouts, large dining rooms, hardwood floors, spacious kitchens, and generously sized rooms. The garden unit offers one bedroom and one bath. Recent building improvements include new windows, newer roofs on both the building and garage, lintel and masonry work, and updated landscaping. Each unit has its own boiler, and tenants pay their own utilities. The basement offers common-area coin-operated laundry and a bonus room ideal for storage, an art studio, crafts, or other uses. A large, landscaped backyard and detached two-car garage complete the property. Please refer to the showing schedule for prearranged showing times.

5057 W Newport Avenue, Chicago
$1,100,000
5 Beds ⋅ 4 Baths ⋅ 12751215 MLS ⋅ ACTIVE Status
Welcome to 4945 W Berenice Ave - a truly one-of-a-kind single-family home designed with intention. Thoughtfully crafted to preserve the charm and character of the neighborhood while blending sophisticated modern living with the timeless elegance of restored historic homes, this residence offers exceptional design, comfort, and functionality throughout. The main level welcomes you with a beautifully appointed living room a formal dining room, featuring elegant fireplace and a cozy barista bar perfect for your morning coffee ritual. The gourmet kitchen is the heart of the home, showcasing luxurious quartz countertops, sophisticated two-tone cabinetry, high-end stainless-steel appliances, a 5-burner range, refrigerator, and a sun-filled kitchen island. The second level features a stunning primary suite complete with a spa-inspired bathroom, oversized shower, dual vanity, and spacious walk-in closet. Two additional bedrooms, a beautifully appointed full bathroom, and a conveniently located laundry room complete the level. The lower level offers even more versatile living space, featuring a generously sized recreation room with a wet bar, two additional bedrooms, and a full bathroom - ideal for guests, a home office, media room, or extended living arrangements. Every finish and detail has been carefully selected to honor the architectural character and originality of the surrounding homes. Inspired lighting, rich oak flooring, warm textures, timeless finishes, and thoughtful details are seamlessly paired with modern conveniences to create a home that feels both sophisticated and inviting.

4945 W Berenice Avenue, Chicago
$350,000
5 Beds ⋅ 2 Baths ⋅ 12749441 MLS ⋅ ACTIVE Status
Greystone architecture and original details give this early 1900s two-flat a character that's distinctly Chicago. Projecting bays, tall windows, hardwood floors and original millwork bring warmth and architectural interest throughout two well laid out residences. The first-floor unit offers 2 bedrooms and 1 bath with separate living and dining rooms, an updated kitchen with granite countertops and stainless steel appliances, in-unit laundry hookup, and a primary bedroom with walk-in closet. Upstairs, the 3-bedroom, 1-bath residence features an expansive living and dining space, updated kitchen and bath, hardwood floors, and in-unit laundry hookup. A full unfinished basement offers additional storage and utility, while generous outdoor space and parking for up to four vehicles are valuable additions. With two distinct residences, the property lends itself equally well to owner-occupancy or a fully income-producing investment. Located near Garfield Park, just east of the Conservatory, with convenient access to public transportation and downtown, this is an opportunity to own an architecturally rich piece of Chicago in a prime location. This property can be purchased as a package with nearby buildings 5315 W Monroe (MLS#12748904); 3344 W Fulton (MLS#12748759) or purchased separately. MULTIPLE OFFERS RECEIVED - Highest & best Due by Tuesday 9/8 at 2PM

4319 W Jackson Boulevard, Chicago
Start Your Search



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.

5 Bedroom Chicago Real Estate

Our website features the best real estate search for 5 bedroom properties available in Chicago and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!