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Browse All Chicago IL 5 Bedroom Properties for Sale

$169,000
5 Beds ⋅ 2 Baths ⋅ 12624314 MLS ⋅ ACTIVE Status
Gorgeous, renovated brick two-flat is an investor's dream and guarantees YEARS of cash flow with long term tenants! This is a solid investment that will produce great returns!! Tenants will enjoy living in a quiet neighborhood convenient to The University of Chicago, major highways, public transportation, restaurants, shopping, and Lake Michigan. In-unit features include: Brand New Appliances, Open Concept Layout, Large Closet Space, and LED Lighting. This property won't last!

531 W 61St Place, Chicago
$240,000
5 Beds ⋅ 3 Baths ⋅ 12624073 MLS ⋅ CONTINGENT Status
Great Opportunity to Own this Fantastic 1.5 Story Home. Plenty of Space and Great Location!! Property features 3 bathrooms, 3 bedrooms on 2nd level and 2 bedroom in the basement, can also be used as recreation room of Family room. Newer flooring, newer mechanicals, newer roof, solid wood cabinetry including bathroom vanities and kitchen cabinets. Updated Electrical throughout. Huge back Yard with nice Patio for summer fun and entertainment. This Austin beauty has a lot to offer. Close to Green and Blue trains and 2 bus lines, 20 minutes to downtown and 5 minutes to Oak Park.

415 N Lawler Avenue, Chicago
$130,000
5 Beds ⋅ 3 Baths ⋅ 12623764 MLS ⋅ ACTIVE Status

10721 S Wentworth Avenue, Chicago
$65,000
5 Beds ⋅ 3 Baths ⋅ 12623050 MLS ⋅ ACTIVE Status
Solid investment opportunity with strong upside potential. This frame 2-flat includes two spacious 2-bedroom units and an additional 1-bedroom garden unit, offering multiple income streams. The property features individual heating systems for each unit, improving efficiency and tenant appeal. While the building requires rehabilitation, it presents a prime value-add opportunity for investors seeking to renovate and increase rental income or resale value. The large backyard offers ample space to add a garage or parking pad-an attractive feature for future tenants.

8405 S Baltimore Avenue, Chicago
$499,900
5 Beds ⋅ 3 Baths ⋅ 12622995 MLS ⋅ ACTIVE Status
SOLID AND GOOD CARE BRICK TWO FLAT WITH GARDEN APARTMENT IT OFFERS TWO BEDROOMS, ENCLOSE FURNACED PORCH FORMAL DINING-ROOM AND BIG LIVING-ROOM IN EACH APARTMENT SEPARATED GAS AND ELECTRIC. FEATURES HARDWOOD FLOORS, NICE AND BIG KITCHENS REMODELED BATHROOMS. 3 HEATING UNITS, SOME NEW WINDOWS AND ROOF, IRON GATE, NEW PATIO, TWO CAR GARAGE, GREAT LOCATION CLOSE TO TRANSPORTATION, SCHOOLS AND SHOPPING.

6113 S Sacramento Avenue, Chicago
$249,000
5 Beds ⋅ 2 Baths ⋅ 12621998 MLS ⋅ CONTINGENT Status
Great opportunity to own a multi-unit property in an up-and-coming area! 2-unit building plus an unfinished basement. The adjacent lot with the 2-car garage is included in the list price. Second floor unit was rehabbed in 2022. New roof, gutters, and window seals were installed in 2022. Newly painted aluminum siding and garage (April 2026). Newer sewer lines and sidewalks. This is a fantastic opportunity for a wise investor or a first-time homebuyer. Rent prices are very low because they are long-time tenants (month-to-month tenancy).

6408 S Aberdeen Street, Chicago
$133,300
5 Beds ⋅ 2 Baths ⋅ 12596933 MLS ⋅ PENDING Status

1333 W 71St Street, Chicago
$920,000
5 Beds ⋅ 4 Baths ⋅ 12622087 MLS ⋅ ACTIVE Status
Brick single family house

3646 S Parnell Avenue, Chicago
$1,875,000
5 Beds ⋅ 4 Baths ⋅ 12619971 MLS ⋅ CONTINGENT Status
New construction 5BR / 4BA duplex-down in a great part of Lakeview, offering single-family-style living with high-end finishes throughout. The main level features an open-concept living and dining space and a chef's kitchen with custom cabinetry, walk-in pantry, Sub-Zero & Wolf appliances, and oversized island. Enjoy a separate wet bar area with beverage center outdoor living with a massive private front terrace with porcelain pavers. The lower level includes radiant heated floors throughout and the large primary suite which offers a spa-inspired bath, soaking tub, separate shower, and custom walk-in closet. Four additional bedrooms provide flexible living options. Additional features include white oak floors, custom millwork, Marvin windows, advanced soundproofing, smart wiring, garage parking, and a prime Lakeview location near dining, parks, and transit. SOME CUSTOMIZATION OPPORTUNITIES ARE STILL AVAILABLE TO MAKE YOUR DREAM HOME A REALITY (based on project timing). ANTICIPATED DELIVERY: JULY 2026. *Images of completed project are of recent build by same developer. *Renderings and plans, etc. are for marketing purposes only; finishes/plans may change at the discretion of Seller. Buyer(s) and their representation to confirm all finishes prior to purchase.

3923 N Janssen Avenue Unit #1E, Chicago
$575,000
5 Beds ⋅ 3 Baths ⋅ 12621240 MLS ⋅ CONTINGENT Status
Step into this beautifully updated 5-bedroom, 3-bath raised ranch, offering nearly new-construction living throughout. Soaring cathedral ceilings and abundant natural light create an airy, open feel on the main floor, while the fully finished lower level features impressive 10-foot ceilings, a cozy wood-burning fireplace, and two additional bedrooms-perfect for guests, multigenerational living, or a private home office suite. Thoughtfully designed with spacious closets, wood flooring throughout, this home has been meticulously maintained since its 2017 rebuild, offering truly no-maintenance living. All major systems and appliances-roof, windows, furnace, AC, water heater, kitchen suite, and more-were installed in 2017, with a new 2025 washer adding extra convenience. A full finished basement, dual sump pumps with battery backup, a detached 2.5-car garage tucked neatly at the rear of the lot, and set up for a security system ensure peace of mind.

3740 N Pacific Avenue, Chicago
$824,900
5 Beds ⋅ 6 Baths ⋅ 12619919 MLS ⋅ ACTIVE Status
Incredible house hack/investment opportunity in Rogers Park off the Jarvis Red Line Station. This beautiful legal 3 unit boasts 2 bathrooms for each unit with unique floor plans that resemble condo layouts than the traditional multi unit cable car. All three units have en-suite bathrooms, open concept living areas, outdoor space AND a parking space! In addition all the units have in unit laundry and central air and heat. Making this an ideal purchase for any house hacker that desires all the modern conveniences rarely affordable in a house hack. Recent updates to both the units and the building make this an ideal opportunity for an investment where you can add cosmetic updating. The basement has been their for 7 years and 1st floor tenant has lived in the building for 20 years. 7341 N Honore is perfectly positioned between Pottawattomie Park and Patrick Touhy Park. Just blocks away from Jewel- Osco, restaurants and bars. 15 minutes to the lake at Fargo Beach!

7341 N Honore Street, Chicago
$3,000,000
5 Beds ⋅ 5 Baths ⋅ 12615483 MLS ⋅ ACTIVE Status
**8 of 16 Homes PRE-SOLD before the MLS!** 1282 Washington is an exclusive collection of 16 single-level residences in the peaceful West Loop, just 2-3 blocks from Skinner West Elementary, Whitney Young High School, Skinner Park, and the dog park. The elegant masonry design features stunning residences that will offer more bedrooms, more bathrooms, more offices, and more living spaces than any other new construction in the area, plus the largest private outdoor spaces in the West Loop. These are condos, but for people with a 10-year plan in the city's best neighborhood. Residence 3B is an incredible single-level home with all the rooms of a single-family home. Boasting fantastic SW natural light, this private elevator home greets you with a grand formal entry, apart from other condos in the area. The home spans 4 suites, gracious Primary Suite with massive Dressing Room and Primary Bath with separate European glass shower and standalone soaking tub, separate private Office, bright Family Room with attached Library/homework area, and TWO expansive, private walkout terraces totaling 515 SF of outdoor living space. The bespoke chef's kitchen stands ahead of other new developments in Chicago, delivering full-height custom cabinetry from Scavolini, curved kitchen island with plenty of counter space and seating, quartz countertops and full-height backsplash, and an integrated appliance suite from Miele and Wolf. Separate 30" refrigerator and 30" freezer columns, integrated gas cooktop, gas oven, speed oven/microwave, and walk-in pantry ensures that the kitchen is ready for your next homecooked meal or catered event. With a full-sized laundry room and large closets throughout, the home is smartly and thoughtfully designed for the needs of today's buyer. Plus two heated garage parking spaces are included in the purchase price. Early buyers will have the opportunity to personalize the finishes in their home. 3/4/5 Bedroom+ Family+ Office homes available from 1.9M to 4.3M. Sales Gallery Now Open! Call today to secure your next West Loop home!

1282 W Washington Boulevard Unit #2A, Chicago
$500,000
5 Beds ⋅ 2 Baths ⋅ 12619248 MLS ⋅ ACTIVE Status
Come see this property located in the desirable Irving Park neighborhood, offering a great opportunity for both investors and owner-occupants. This property sits on a well-positioned lot and features solid bones with plenty of potential to update, renovate, or customize to your vision. Whether you're looking to create your ideal living space or maximize rental income, this is a versatile property that allows you to make it your own. Conveniently located near parks, schools, shopping, and public transportation, making it attractive for tenants and future resale alike. A great value-add opportunity in a strong and growing area.

4136 N Sacramento Avenue, Chicago
$74,900
5 Beds ⋅ 2 Baths ⋅ 12618253 MLS ⋅ PENDING Status
Excellent opportunity to own a large Investment property in the Greater Grand Crossing community! The home features a fireplace, an expansive open kitchen, and a large basement that can be utilized as additional living space. It is located near schools, shopping, and public transit.

7804 S Ellis Avenue, Chicago
$550,000
5 Beds ⋅ 2 Baths ⋅ 12609065 MLS ⋅ ACTIVE Status

2836 S Union Avenue, Chicago
$1,370,000
5 Beds ⋅ 5 Baths ⋅ 12616276 MLS ⋅ ACTIVE Status
Set on an exceptionally rare double lot, this remarkable three-story residence offers a level of privacy and outdoor living almost unheard of in the city. Here, your views are your own; lush, open, and uninterrupted, creating a true sense of escape just minutes from everything Chicago has to offer. Designed for both relaxation and entertaining, the fully fenced grounds feel like a private resort. Enjoy a beautifully landscaped yard complete with a putting green, tranquil water feature, pool, outdoor kitchen with pergola, surround sound, and expansive green space for recreation, gardening, or simply unwinding. Mature perennials frame the home from every angle, delivering color, texture, and serenity throughout the seasons. Step inside to a grand, architecturally designed interior where a soaring three-story foyer sets the tone. Rich craftsmanship is showcased in the inlaid oak flooring, custom millwork, solid oak doors, and a graceful winding staircase. Sunlight pours through countless windows, filling the home with warmth while offering breathtaking views, from morning light to glowing sunsets. The home features two exceptional primary suites, each offering a distinct experience. One presents a more traditional layout with an expansive, spa-like bath often mistaken for an additional room. The other is a vaulted sanctuary, highlighted by an arched wall of windows and sweeping, unobstructed views that stretch for miles. Every season is meant to be enjoyed here, from spring magnolias perfectly positioned outside your windows, to vibrant autumn foliage, to the soft glow of the city skyline on winter evenings. Thoughtfully designed for modern living, the home also offers a welcoming family room with fireplace, a first-floor bedroom and full bath, a formal dining room for elegant entertaining, and a kitchen that opens beautifully to the backyard, making everyday moments feel extraordinary. A second-floor office /flex space are ideal options for working from home or creating a nursery or studio. From the charming front porch swing to the striking metal fence and extended driveway with ample parking, every detail, inside and out, has been carefully considered. Ideally located in Norwood Park, near major highways, Metra access, fitness centers, hospitals, schools, and a variety of shopping and dining destinations, this home offers the perfect balance of tranquility and convenience. Lovingly maintained by the same family for generations, this is more than a home. It's a legacy property. Now, it's your opportunity to carry it forward and experience a lifestyle that is truly unmatched in Chicago.

6883 W Hobart Avenue, Chicago
$180,000
5 Beds ⋅ 2 Baths ⋅ 12610328 MLS ⋅ ACTIVE Status
Great investment property! Property is located close to the expressway and transportation. Offers five bedrooms total. Three bedrooms in Unit #1 and two bedrooms in Unit #2. Property sits on a double lot. Great opportunity to own a two unit building on a solid block. Come check out and add this to your porfolio of properties today! Property is being sold AS-IS. Fully occupied and tenants are on a month to month lease.

10136 S Union Avenue, Chicago
$496,000
5 Beds ⋅ 2 Baths ⋅ 12615729 MLS ⋅ ACTIVE Status
Immaculately maintained and spacious 5 bedrooms 2 bath home on large 50 x 140 lot in highly sought after Garfield Ridge! With the add on of an addition this beautiful updated home offers a flexible floor plan with living space on three finished levels. Features include living room with floor to ceiling windows, updated kitchen with a ton of white cabinets including a great buffet wall, ss appliances, along with a breakfast room! office in one of the bedrooms, Gather in the nice family rm or spacious lower level with a recreation room, bath and large laundry rm. Tons of storage in this home including a large tall attic. Enjoy outdoor fun in this large backyard , storage shed and large side concrete drive to accommodate many cars! So many updates including plantation shutters, hardwood floors under vinyl planks, dual zone HVAC. Hard to find this size lot and a driveway (no alley). You will love this home and neighborhood!!!

Chicago
$335,000
5 Beds ⋅ 2 Baths ⋅ 12615772 MLS ⋅ PENDING Status
Great investment opportunity in the Austin neighborhood! This property needs some TLC and offers strong potential for renovation, rental income, or value-add investment. Buyer and buyer's agent to conduct their own due diligence prior to submitting an offer. Located on Chicago's West Side, the property has convenient access to public transit (CTA Green Line & buses), parks and recreation nearby including Columbus Park, local retail and amenities, and easy connections to downtown Chicago. Sold as-is;Submit your offer today-don't miss this opportunity!

4912 W Fulton Street, Chicago
$59,900
5 Beds ⋅ 2 Baths ⋅ 12615706 MLS ⋅ CONTINGENT Status
Reabbers and Investors, lowest priced 2 flat in the area!!! Separate heating already in place, dry basement. Property is being sold AS_IS. Seller will not supply survey.

11576 S State Street, Chicago
$774,900
5 Beds ⋅ 3 Baths ⋅ 12614346 MLS ⋅ ACTIVE Status
Forest Glen / Sauganash / Edgebrook developers and investors- bring your architect and contractor! Huge private lot (over 11,600 sf) bordering the forest preserve, with dedicated street and no direct neighbors! Deer literally live around the property, while still maintaining a City of Chicago address! Developers can consider options to parcel out, demolish, and or rehab/expand the existing property. The value in this opportunity is in the multi-lot, over-sized property, but the property includes an existing 3,500 sf, 5 bedroom, 3 bath home and two separate garages (3.5 car attached and 2.5 car separate garage in alley). The existing property needs to be updated with new roofing, siding, and interior improvements.

5787 N Clifford Avenue, Chicago
$199,900
5 Beds ⋅ 2 Baths ⋅ 12613801 MLS ⋅ PENDING Status
2 flat Graystone in Austin Area with 3 bedrooms on 2nd floor, 2 bedrooms on 1st floor, 5 minutes to I-290 expressway. This is a once in a lifetime investment opportunity. Solid 2 flat would make this a remarkable fix and fip candidate / Come and make an offer and have this be your Spring project! Property is being sold occupied / Please Do not disturb Occupants / being sold in AS IS condition / no survey nor disclosures / taxes are prorated / Please see agent remarks for offer submission instructions.

212 N Leamington Avenue, Chicago
$850,000
5 Beds ⋅ 3 Baths ⋅ 12612159 MLS ⋅ ACTIVE Status
Gorgeous true 3-story Victorian on an oversized 45X124 lot in the heart of Edison Park! Over 3200 sqft on 3 levels plus the finished basement. A terrific floor plan, very spacious rooms, family room with vaulted ceiling & fireplace, vintage style features throughout but also many updates, 4 bedrooms and large deck on the 2nd floor, top floor is all primary suite on with balcony, fireplace, great closet space and full bath. Zoned heat & A/C. Finished basement. Fenced yard. Brick paver patio. 2-car garage. Near Olympia Park & Monument Park, Downtown EP, restaurants, shopping, highly desirable local schools, the Metra & Uptown Park Ridge. A+ location in this wonderful community.

6548 N Oliphant Avenue, Chicago
$4,495,000
5 Beds ⋅ 5 Baths ⋅ 12595802 MLS ⋅ ACTIVE Status
On one of Lincoln Park's most coveted blocks, 1811 N Howe Street is a home that reveals itself in layers - each level, each room, each outdoor space more unexpected than the last. At nearly 5,900 square feet across three levels, this French Provincial limestone and brick residence is defined by a singular architectural vision: a soaring interior atrium with 30-foot ceilings and a south-facing glass block wall that floods the home with extraordinary natural light from the Brazilian cherry hardwood floors below to the high ceiling above. It is a home that manages to feel both grand and luminous, dramatic and deeply livable. The main level is designed for the full range of daily and celebratory life. A separate formal dining room - appointed with one of five antique fireplace mantels, each averaging over $20,000 - opens to a generously proportioned living room, also with a fireplace. The kitchen is equipped with a Sub-Zero refrigerator, Wolf range and oven, Bosch dishwasher, granite countertops, and Perenti custom cabinetry. A spacious family room anchors the rear of the main level. A powder room and two-car detached garage complete this level. The home's outdoor space features a spectacular private in-ground swimming pool surrounded by an expansive patio - a coveted rarity in Chicago - plus a courtyard entry at the front. The second level is devoted to private living. The primary suite features a gas fireplace, a spa-caliber bath with whirlpool tub, steam shower, granite double vanity, and a walk-in closet. Two additional bedrooms share this level, each served by refined ensuite baths, joined by a dedicated sauna, second-floor laundry, and a large private terrace. The third level adds a fourth bedroom, a full bath, a substantial den that serves equally as a fifth bedroom or creative space, and access via an outdoor walkway to a rooftop terrace above the garage with open sky above. A further upper terrace crowns the home. Six gas fireplaces in all - five with antique mantels - are distributed across every principal level, giving each room its own warmth and character. Three-zone HVAC (2016) and a newer hot water tank (2020) ensure mechanical reliability throughout. Interior design by Marty Lescht. Sprinkler system and landscape lighting. HOB (Howe/Orchard/Burling) neighborhood has an active and supportive association, including 24/7 security monitoring. Steps from Lincoln Park, the lakefront path, the farmers' market, and the best dining, shopping, and cultural life Chicago has to offer - in one of the city's most treasured neighborhoods.

1811 N Howe Street, Chicago
$785,000
5 Beds ⋅ 4 Baths ⋅ 12612466 MLS ⋅ ACTIVE Status
Experience the perfect blend of vintage charm and modern sophistication in this meticulously maintained multi-unit building, perfectly situated on the border of Avondale and Logan Square. The primary unit has beautiful hardwood floors. Enjoy an updated kitchen with stainless steel appliances. This is not your standard 2-flat; it is a versatile investment or owner-occupant sanctuary designed for the modern buyer. featuring two legal dwelling units, plus a separate third unit currently operating as a short-term rental. Ideal for investors or owner-occupants. The lower level offers additional finished space with strong potential for conversion to an ADU (Accessory Dwelling Unit) or future duplex-down expansion (subject to zoning approval and City of Chicago regulations). Buyers to perform their own due diligence regarding short-term rental licensing and ADU eligibility. Property provides multiple revenue streams, flexible living arrangements, and long-term value-add potential. The building features an updated roof, electric panels, windows, and mechanicals, along with three separate water meters. Outdoor highlights include a private rear patio and an oversized two-car garage, a rare find in the area. Prime location with excellent access to public transportation including nearby CTA bus routes and convenient access to the CTA Blue Line and CTA Brown Line, making commuting downtown or to O'Hare simple.Surrounded by some of the neighborhood's most popular dining and coffee spots, including Daisies, Lula Cafe, Eden, and local favorites along Kedzie, Irving Park, Belmont, and Milwaukee corridors. A strong opportunity for investors or owner-occupants seeking a turn-key multi-unit in a rapidly appreciating area with solid rental demand.

3036 N Kedzie Avenue, Chicago
$669,000
5 Beds ⋅ 3 Baths ⋅ 12595429 MLS ⋅ ACTIVE Status
This beautiful side-by-side 2-unit corner building with a detached 2-car garage is fully renovated throughout. Updates include all-new appliances, granite countertops, new flooring, updated bathroom tile, and fresh paint. The larger unit comes fully furnished and is ready to be rented immediately as an Airbnb. This is a fantastic opportunity for an owner-occupant to live in one unit while generating income from short-term rentals in the second unit, or for an investor seeking a move-in-ready, income-producing property. A rare and versatile opportunity you do not want to miss.

6259 W Peterson Avenue, Chicago
$134,900
5 Beds ⋅ 2 Baths ⋅ 12611103 MLS ⋅ ACTIVE Status
Located in the sought after Grand Crossing community this large two story home has undergone a full renovation and is move in ready with an expansive floor plan where the home lives and feels much larger than the home appears! The main level features a very open and modern layout with a living room/dining room combo where the flooring has been updated and is newer, custom wainscoating in the dining room gives the space a charming classic feel. The main level bathroom offers a standalone shower with a new modern vanity, the kitchen is also updated with quartz counters, a stylish backsplash and the space has been opened to include a breakfast nook as well! The second level of the home lives much larger with 4 spacious bedrooms, a family room sitting area and full modern bathroom! The basement is unfinished and the rear yard offers parking pad with ability and space to build a garage! This home is move in ready, great condition and the space will have you amazed as you enter!!

7122 S Champlain Avenue, Chicago
$150,000
5 Beds ⋅ 3 Baths ⋅ 12610025 MLS ⋅ PENDING Status
NICE MULTI-UNIT DWELLING WITH 3 SEPERATE UNITS. ALL UNITS HAVE BEEN UPDATED. PROPERTY BEING SOLD AS IS.

6732 S Honore Street, Chicago
$425,000
5 Beds ⋅ 3 Baths ⋅ 12586544 MLS ⋅ ACTIVE Status
Beautiful, large single-family brick home in up-and-coming North Lawndale which boasts access to local parks, community centers, and historic sites. 2026 gut rehab. House originally built in 2008. Multiple new construction homes on the same block. Adjacent lot for sale as well from the same owner. New electrical wiring, new HVAC units, new plumbing, new windows, all new inside finishes including kitchen, appliances, bathrooms. New detached 2 car garage. New roof. Nearby attractions include Shedd Park (0.5 mi), the urban agricultural hub Farm on Ogden (0.3 mi), and the Firehouse Community Arts Center. The area is walkable with access to CTA bus and rail options. Welcome home!

1810 S Hamlin Avenue, Chicago
$319,900
5 Beds ⋅ 2 Baths ⋅ 12609770 MLS ⋅ ACTIVE Status
Attention investors or owner occupants. This gorgeous 3 bedroom single family home with included coach house is ready for a new owner. Live in the Main front house and continue to rent the rear for added income. Both properties scream pride of ownership. Freshly painted from top to bottom, new flooring, brand new appliances: stove, fridge, dishwasher, washing machine & dryer. Water main just replaced from the outside in. Modern kitchen and bath. Rear coach house features 2 bedrooms, laundry in basement. Stove, fridge, washer, dryer, microwave all included in sale as well. Tenant occupied and would love to stay if possible. Henry Clay elementary school directly across the street. Minutes away from shopping and Indiana boarder!

13231 S Buffalo Avenue, Chicago
$129,900
5 Beds ⋅ 2 Baths ⋅ 12608396 MLS ⋅ CONTINGENT Status

3345 W Monroe Street, Chicago
$279,999
5 Beds ⋅ 3 Baths ⋅ 12607387 MLS ⋅ ACTIVE Status
Located along a quiet, tree-lined street in Auburn Gresham, this timeless brick 2-flat has been lovingly maintained and is ready for its next chapter. Picture mornings on the screened in porch with coffee in hand. Step inside and you'll find two spacious units, each with sunlit living rooms, separate dining spaces, and eat-in kitchens waiting for your personal touch. The enclosed rear porches invite imagination and are perfect for a reading nook, office, or extra storage. Downstairs, the partially finished basement opens even more possibilities with two additional rooms and plumbing that is ready for an additional bathroom. This space can become an in-law suite, creative studio, or increase your rental income and make it a duplex down from the first floor unit. Out back, the fenced yard and two-car garage offer both comfort and practicality. So, whether you're an investor seeking steady income or a homeowner ready to build roots, this classic Chicago 2-flat offers the space, charm, and flexibility for you to grow.

7923 S Carpenter Street, Chicago
$7,750,000
5 Beds ⋅ 5 Baths ⋅ 12282585 MLS ⋅ ACTIVE Status
Classic limestone and brick single-family home on two and a half lots on coveted Burling Street with spectacular outdoor space. This outdoor footprint includes a swimming pool, outdoor kitchen, temperature controlled four-season glass atrium with accordion windows, sport court, and a gated parking pad for guests. The main level features high ceilings across a large living room with hardwood floors and a stone fireplace, a formal dining room with modern millwork and glass French doors that open to the deck, a grand staircase, a powder room, a chef's kitchen, a built-in breakfast table, and a family room with a second fireplace and a coffered ceiling. The family room connects via sliding doors to a four-season sunroom accessing the best-in-class outdoor space. Back inside, the second level features two secondary bedrooms, a laundry room, and a fabulous primary suite with a third fireplace, two custom walk-in closets, and a spa bath with a dual vanity, soaking tub, and steam shower. The top floor is dedicated to a large entertainment space, a game room with a wet bar, a guest bedroom or office, a full bath, and two more decks. This home's lower level has a large recreation space, a guest bedroom, a full bath, a 2nd laundry room, and access to the home's attached garage. Additional callouts include heated sidewalks, front steps, and parking pad, amazing natural light throughout, arched transitions and doorways, designer light fixtures, abundance of storage, composite decking, irrigation, and professional landscaping. There is private neighborhood security with multiple cars working each night. Located within a short walk to the best dining and shopping in Lincoln Park, 1838 N Burling is elevated living on Chicago's North Side.

1838 N Burling Street, Chicago
$300,000
5 Beds ⋅ 3 Baths ⋅ 12603574 MLS ⋅ CONTINGENT Status

4608 S Fairfield Avenue, Chicago
$259,900
5 Beds ⋅ 2 Baths ⋅ 12599972 MLS ⋅ ACTIVE Status

5932 S Parnell Avenue, Chicago
$2,500,000
5 Beds ⋅ 4 Baths ⋅ 12581028 MLS ⋅ CONTINGENT Status

5643 N Glenwood Avenue, Chicago
$1,300,000
5 Beds ⋅ 5 Baths ⋅ 12601387 MLS ⋅ PENDING Status
Welcome to 7015 N. Sheridan Rd - a rare opportunity to own a piece of Chicago history on an oversized 46 x 150 lot on the east side of Sheridan, just steps from the lake. Originally built in the 1800s, this expansive 5-bedroom, 4.1-bath home blends timeless architectural charm with thoughtful modern updates. From the moment you step into the grand foyer, you'll be captivated by the intricate woodwork, stunning staircase with stained glass details, and preserved vintage character throughout. The main level offers a spacious living room with gleaming hardwood floors and recessed lighting, a cozy sitting area with a gas fireplace, and a formal dining room that flows seamlessly into the oversized kitchen. The kitchen is truly the heart of the home-featuring stainless steel appliances, an island, and abundant cabinetry and counter space. A convenient mudroom leads to the rear porch, expansive parking area, and easy access to the beach-perfect for rinsing off after lake days. Upstairs, the second level features three generously sized rooms, including a primary suite with multiple closets and a beautifully updated en suite bath complete with a double vanity, soaking tub, and separate shower. Two additional rooms are connected by a Jack-and-Jill bath, with flexibility for bedroom or office use. The top floor offers a private suite with its own bedroom, ample storage, and full bathroom-ideal for guests or extended living. The lower level provides exceptional versatility, featuring two laundry areas, extensive storage, and a fully equipped in-law suite with a private entrance, 2 bedrooms, 1 bath, in-unit laundry, and a modern kitchen with living and dining space. This is one of the last remaining homes of its kind in the area-offering historic charm and incredible future upside-all just steps from Lake Michigan.

7015 N Sheridan Road, Chicago
$160,000
5 Beds ⋅ 2 Baths ⋅ 12600884 MLS ⋅ PRICE CHANGE Status

7700 S Lowe Avenue, Chicago
$369,900
5 Beds ⋅ 3 Baths ⋅ 12599736 MLS ⋅ ACTIVE Status
This home is simply gorgeous! Beautiful open floor plan that exudes warmth, charm, and BRAND NEW SPACIOUS 2 CAR GARAGE! There are beautiful new wood floors that are on the main level and stairs. The kitchen features large granite island for cooking and entertaining (refrigerator and stove to be included). The new lighting illuminates the spacious rooms and meticulous workmanship. There are 2 master size bedrooms on the second level with a laundry room for convenience, as well as, one in the beautiful, finished basement. The yard is huge for outdoor activities. Basically, this is an all-new home that you can enjoy for years to come! Rehab was completed with approved architectural drawings and permits approved. There are 2 buildable lots adjacent to the home that can also be purchased. Must see to appreciate!

8839 S Colfax Avenue, Chicago
$350,000
5 Beds ⋅ 2 Baths ⋅ 12597004 MLS ⋅ CONTINGENT Status
Welcome to this updated Bungalow! Featuring new, LG appliances and modern finished throughout. Featuring updated kitchen, and spacious basement! Conveniently situated with easy access to major expressways including I-94/Dan Ryan, making commuting to downtown Chicago and surrounding areas a breeze. Close to public transportation, shopping, dining, schools, and local parks. Ready for any buyer to call this property HOME!

7549 S Michigan Avenue, Chicago
$1,395,000
5 Beds ⋅ 5 Baths ⋅ 12594472 MLS ⋅ ACTIVE Status
This extraordinary custom-built estate redefines luxury living in Chicago's West Elsdon neighborhood. Constructed in 2005 with a full masonry and stone exterior, the residence offers over 5,760 square feet of living spaces, combining high-end mechanical systems with exceptional custom craftsmanship. The privately gated residence features 5 spacious bedrooms and 3 bathrooms, 2 powder rooms, including 3 bedroom suites with private bathrooms, offering comfort and privacy for family and guests. Every closet is finished with custom shelving systems. The first level showcases radiant heated floors, providing consistent and energy-efficient comfort. The second-level elegant living room features a gas fireplace and a stunning Rich Toffee custom library wall complete with a rolling ladder, creating a warm and sophisticated gathering space. The expansive chef's kitchen is equipped with Sub-Zero side-by-side oversized refrigeration, double ovens, two dishwashers, and a built-in trash compactor. The second-floor private garden includes a charming outdoor fireplace and beautifully maintained perennial landscaping creating a peaceful sanctuary above the city. A built-in elevator provides convenient access to every level of the home. The primary suite on the third level features a private balcony, built-in cabinet and a spa-inspired bathroom with a standalone shower and deep Jacuzzi soaking tub. The expansive rooftop deck offers breathtaking 360-degree skyline views, providing the perfect setting for entertaining or relaxing. 3-car heated garage plus additional outdoor parking spaces within the gated grounds. Located just 15 minutes from Downtown Chicago, the property offers convenient access to I-55, I-90/94, and I-294, as well as the Pulaski Orange Line and Midway International Airport, this exceptional property offers the rare combination of size, privacy, luxury amenities, and convenient city access. Schedule your private tour today!

3914 W 51St Street, Chicago
$310,000
5 Beds ⋅ 2 Baths ⋅ 12590543 MLS ⋅ ACTIVE Status
Investment opportunity at 4327 W Monroe St in Chicago! This two-flat is fully occupied, making it an ideal income-producing property from day one. The building features two units-a spacious 3-bedroom, 1-bath unit and a comfortable 2-bedroom, 1-bath unit-offering strong rental appeal and steady cash flow. Whether you're expanding your portfolio or looking for a solid investment, this property checks all the boxes with established tenants already in place. Conveniently located with easy access to local amenities, transportation, and more. Don't miss out on this reliable, income-generating asset! Sold AS-IS.

4327 W Monroe Street, Chicago
$345,000
5 Beds ⋅ 3 Baths ⋅ 12586510 MLS ⋅ CONTINGENT Status
Great investment opportunity in Englewood! This well-maintained two-unit building features two spacious units, each offering 2 bedrooms and 1 bathroom. Both units have separate utilities and individual meters, providing convenience for owners and tenants. The finished basement, powered by electricity, offers additional living space and can function as a potential in-law suite or extended living area. One washer and dryer will remain with the property. Outside, enjoy a rear patio deck that is perfect for relaxing or entertaining, along with two parking spaces in the back for added convenience. This property is ideal for owner-occupants or investors looking to generate rental income. *Please note photos have been cleaned up with AI software*

7034 S Hermitage Avenue, Chicago
$5,900,000
5 Beds ⋅ 6 Baths ⋅ 12593204 MLS ⋅ ACTIVE Status
Motivated Seller offers unparalleled opportunity to own a full floor penthouse at a truly outstanding value! Spanning 8,400 square feet, this residence offers 360-degree views of Chicago's iconic skyline, world-class architecture, and Lake Michigan, delivering front-row sunrise to sunset views. Perched above the Park Hyatt Hotel, this 5-bedroom, 4.2-bath home provides access to top-tier amenities: Spa, Indoor Pool, Fitness Center, In-Room Dining, and NoMI Restaurant. Enter the home through your own private and secure elevator foyer, leading to an expansive living and dining area with windows perfectly framing the lake, and illuminated by gallery-grade ERCO lighting to highlight any art collection. The thoughtful layout balances space both for large scale entertaining or quiet evenings at home. Crafted with the finest finishes and materials throughout, including an exceptional Bulthaup kitchen with integrated professional appliances. 2 garage parking spaces included. Premier location offering everything a first-class city like Chicago has to offer, within walking distance: Acclaimed Dining, Shopping, Museums, Lakefront, River Walk, Harbors, and more. Welcome Home.

800 N Michigan Avenue Unit #63PH, Chicago
$150,000
5 Beds ⋅ 2 Baths ⋅ 12592272 MLS ⋅ ACTIVE Status
Investor's opportunity! This unique property was originally a single-family home and has been converted into a legal 3-unit building, offering excellent income-producing potential. Perfect for investors or owner-occupants looking to generate rental income while building long-term equity. The property offers a great opportunity for value-add improvements, renovation, or portfolio expansion. With multiple units, it provides the potential for strong cash flow and long-term appreciation. Conveniently located near public transportation, major expressways, shopping, restaurants, schools, and local amenities, making it highly attractive for tenants and commuters alike. A great opportunity to maximize rental income and increase property value. Do not miss your chance to secure this multi-unit investment opportunity. Schedule your showing today! Short sale. Sold "as-is."

1044 W Marquette Road, Chicago
$550,000
5 Beds ⋅ 3 Baths ⋅ 12267332 MLS ⋅ CONTINGENT Status

Chicago
$2,950,000
5 Beds ⋅ 5 Baths ⋅ 12537934 MLS ⋅ CONTINGENT 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
$449,999
5 Beds ⋅ 3 Baths ⋅ 12590537 MLS ⋅ RE-ACTIVATED Status

5037 W West End Avenue, Chicago
$295,000
5 Beds ⋅ 2 Baths ⋅ 12585003 MLS ⋅ PENDING Status
Perfect home with additional living quarters for in-laws or you can live in one unit and rent out the other. Home has 5 bedrooms. 3 bdrms in upper unit including a master with bar or turn into an office. 2 bdrms in lower level. Newer laminate wood flooring. Newly painted. Newer plumbing. Home has 2 separate kitchens in each unit. It has 2 separate electrical boxes along with separate utilities along with shared washer/dryer. 2 car garage with deck along with storage or turn it into a "Man Cave." Low taxes. Backyard view of La Villta Park which has 21 acres to enjoy. Close to I-55. Selling As-Is. SQ is for upper unit.

2823 S Troy Street, Chicago
$139,999
5 Beds ⋅ 2 Baths ⋅ 12583848 MLS ⋅ CONTINGENT Status

Chicago
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