View All Chicago IL Airbnb-Friendly Homes Listings

$800,000
12754162 MLS NEW Status
LAKE VIEWS from this 3,750 sq ft condo (commercial or residential) with private entrances - ONLY 213 PER SQ FT --Rare opportunity w lake views. New Eastside/ Lakeshore East MIXED USE OR 1 USE-"As-Is Ready" or develop the property-CITY ZONING LETTER AVAILABLE-Commercial / RESIDENTIAL / MIXED LIVE-WORK / SERVICES / OVERNIGHTS / *SEE ZONING LETTER - 3,750 sq ft divided into 8 areas. Can divide tax PINs and sell off or lease out - MANY possibilities, ready to be developed or used as-is. Rare opportunity to own your own commercial space within the PUD #70 (Planned Unit Development) The unit has three entrances/exits, a semi-private entry, a semi-private elevator, and private stairs. It also has wraparound windows with three exposures. 5 toilets, 7 sinks included in a currently small kitchen, maintenance closet and three bathrooms. Great spa - hair - nails- medical - imaging - office -Kitchen and bathroom capable - Currently commercial can be converted to full residential or split as mixed. We have an advisory letter from Chicago City Zoning of what is zoned capable. Owners have the right to use the building amenities. Building amenities include a 5-star "resort-like" health club and spa. Basketball, racquetball, ping-pong, free weights, machine weights, cardio, winter garden, child's playroom, famous geodesic year-round sunny pool, saunas, and steam rooms. A new multi-function room with an open kitchen and media space. Parking is 220/mo reserved. Discounted parking tickets are sold to owners to sell/give to clients and customers. 8 FOR 12-hour parking. Dog friendly. Visiting guests/clients may come through the main building lobby and check in with the front desk, OR enter a semi-private entrance for direct access. There are unlimited possibilities of use! HOA /mo 3,576 includes heat, a/c, gas, amenities, pool, health club, spa, lounge, conference room. Currently used as a day care, property may be converted to residential or get approval for an Airbnb-type set up. Zoned for almost all. See zoning letter. Showings only on weekends or after 6:00pm daily. There are two grocery shopping options, either Bockwinkel's Harbor Market (across the street) or a 2-story Mariano's grocery store with good prices and a plethora of item options for your daily shopping needs. Very friendly building with lots of social activities and events such as a book club, world affairs club, bingo, summer picnic, children's Halloween party, children's holiday party, and a resident holiday party, to name a few. Great Outer Drive East community in the New Eastside neighborhood. Nestled in the New Eastside neighborhood is Lakeshore East Park. This 6-acre oasis in the neighborhood's nucleus includes large grassy areas, a children's playlot, and a dog park. Maggie Daley Park is across Randolph Street and incorporates tennis courts, a children's activity area, park district facilities with programming, the famous ribbon ice skating rink, mini-golf, and professional outdoor climbing walls. Millennium Park is a block away from all the world-famous music venues, including the Grant Park Orchestra, Saturday morning exercise classes, and outdoor movies in the summer. Located in the New Eastside neighborhood, this prestigious condo is just moments away from fine dining, upscale shopping, the lake and harbor, and cultural landmarks. Experience the pinnacle of luxury living in a residence that offers both serenity and sophistication. 30-minute free parking for showings, guests, and deliveries.

400 E Randolph Street Unit #2NDFLOOR6B, Chicago

$299,900
1 Beds 1 Baths 12737451 MLS ACTIVE Status
Stunning City & River Views in the Heart of Chicago! Welcome home to the highly sought-after '10 tier 17th floor unit at River Plaza, where panoramic skyline and river views take center stage. This spacious 820 sq. ft. one-bedroom, one-bath residence offers front-row seats to everything that makes downtown Chicago extraordinary. Watch boats cruise the river, trains glide through the city, and the skyline come alive-all from the comfort of your own home. Flooded with natural light through oversized windows, this move-in-ready home features beautiful new hardwood floors (2025), an open and versatile layout, and incredible storage with two oversized closets. The bright white kitchen is equipped with stainless steel appliances and a convenient breakfast bar, flowing seamlessly into the expansive living area-perfect for entertaining, working from home, or simply taking in the breathtaking views. The spacious bedroom offers endless furniture possibilities, while the refreshed bath and built-in glass shelving add style and function. The lifestyle at River Plaza is second to none. Residents enjoy 24-hour door staff, a beautifully renovated indoor pool, hot tub, sundeck, fitness center, business center with Wi-Fi, bike storage, on-site laundry, grocery store, deli, salon, and more-all under one roof. The building is exceptionally well maintained, with recent HVAC improvements, updated hallways, approximately $4 million in reserves, and a strong ownership profile with approximately 70 owner occupancy. Investor-friendly with no rental cap (12-month minimum lease; no short-term rentals/Airbnb). Monthly assessments include RCN cable with 250+ channels and 155 Mbps internet. Cats are welcome; no dogs. Whether you're looking for your first home, a city pied-a-terre, or a smart investment, this is your opportunity to own a front-row seat to one of Chicago's most iconic neighborhoods. Come experience why life is better at River Plaza.

405 N Wabash Avenue Unit #1710, Chicago

$250,000
2 Beds 1 Baths 12737112 MLS CONTINGENT Status
Just one block from the lakefront and beach, this beautifully maintained home offers comfort, thoughtful updates, and an unbeatable location. Step inside to a spacious living room filled with natural light, gleaming natural hardwood floors, and fresh paint throughout. A charming architectural arch adds warmth and character to the living space. The generously sized bedrooms feature full-size windows and ample closet space. The updated kitchen features quartz countertops, stainless steel appliances, and a top-of-the-line LG dishwasher installed less than a year ago. Enjoy the convenience of in-unit LG washer and dryer, added by the current owner, plus a newer toilet and a brand-new furnace for added peace of mind. The unit also includes a large, dedicated storage locker, providing valuable extra space for everything, plus an additional separate bike storage room. Location is truly one of the standout features! The lakefront and beach are just a block away, the Red Line is approximately a 7-minute walk, and the 147 bus runs right outside the property, making commuting and getting around the city incredibly convenient. Enjoy easy access to shopping, dining, public transportation, and all that vibrant Rogers Park has to offer. With an affordable price point, low property taxes, investor-friendly ownership, and a pet-friendly building, this is a wonderful opportunity to enjoy convenient Chicago living just steps from the lake. Feel secure with ring camera security system and additional locks added to the door. Airbnb allowed!! Don't miss it!

1353 W Fargo Avenue Unit #GW, Chicago

$550,000
2 Beds 2 Baths 12709469 MLS CLOSED Status
Experience the perfect blend of timeless vintage charm and modern updates in this rare 2-bedroom, 2-bath duplex, located in one of East Lakeview's most desirable courtyard buildings within the highly acclaimed Nettlehorst School District. Nestled on a quiet, tree-lined street, this beautifully updated home offers a flexible floor plan with two generously sized bedrooms, either of which can serve as the Primary Suite. The sun-filled main level features 9-foot ceilings, gleaming hardwood floors, a stunning limestone fireplace and fresh paint (2025) The updated kitchen boasts SS appliances including a Fisher & Paykel refrigerator (2021), new quartz countertops (2025), and the convenience of an in-unit washer/dryer (2024). The finished lower level offers luxury vinyl flooring, a beautifully renovated full bath and additional living space ideal for a family room and/or home office. This pet/investor friendly building (NO Airbnb) includes private basement storage, easy street parking, and assessment that covers heat, cable, internet, building maintenance, landscaping and snow removal. This unbeatable location is just steps from Chicago's lakefront, tennis courts, golf course, beaches, bike and running trails, with CTA buses, the Red Line, and easy access to O'Hare. Jewel-Osco, Whole Foods, neighborhood cafes, restaurants, boutiques, nightlife and Wrigley Field are all within walking distance. Move right in and enjoy sophisticated city living in one of Chicago's most sought-after neighborhoods!

542 W Brompton Avenue Unit #1N, Chicago

$440,000
2 Beds 2 Baths 12607371 MLS CLOSED Status
You cannot beat this location!!!! Everything Fulton Market/West Loop have to offer are just steps away from you and everything River North/Loop have to offer are just minutes away....all while being tucked away in a quiet side street to avoid the hustle and bustle of the city. Countless bars, restaurants, grocery stores, and stores are within minutes of walking distance. The other beauty of this location lies with the ease of transportation; even though this unit has a seperate deeded indoor/heated parking spot, it is also right next to blue/pink/green L stops, highway, and Ogilvie Train Station. As you walk into this unit, you will be greeted by a very spacious open-floor plan. One of the wonderful ammenities of this top-floor unit is that the entire Northern side wall is covered in floor to ceiling windows to allow maxium sunlight inside. The grand floor plan allows space for a dining area overlooking the living room; however, the possibilities are endless with this space. You can convert the dining space to an office area or even extend the kitchen to have a massive island overlooking the living room. The balcony is perfectly located to boast exceptional views of the Willis (Sears) Tower, while being large enough to grill out on those warm summer nights. The very roomy master bedroom, again fully equipped with floor to ceiling windows, also includes duel closets as well as an updated onsuite private bathroom. Towards the front end of the unit lies the second bedroom, second FULL bathroom, in-unit laundry, as well as closet space for storage. Don't forget about the incredible ammenties of this building: large shared outdoor terrace, show-stopping party room (with shuffleboard), and fully furnished gym. INVESTOR FRIENDLY and also rare building to be AIRBNB FRIENDLY!!! Parking spot available for purchase for $30,000.

660 W Wayman Street Unit #707, Chicago

$860,000
3 Beds 2 Baths 12515122 MLS CLOSED Status
***MULTIPLE OFFER RECEIVED, HIGHEST AND BEST DUE WEDNESDAY AT 7. Nestled in the heart of East Lakeview, this pristine 3-bedroom, 2-bath townhome is a rare urban oasis offering exceptional indoor-outdoor living with a dramatic floor-to-ceiling glass wall that fully opens to an oversized private patio-perfect for entertaining, relaxing, or giving your dog his own private outdoor space. Talk about Dog friendly! The open-concept main level centers around a striking chef's kitchen with crisp white cabinetry, Sub-Zero refrigeration, Bosch appliances, and a statement waterfall island. Upstairs, the primary suite feels like a retreat with two closets (including an enormous walk-in) and a spa-inspired bath with soaking tub, glass-enclosed shower, and dual vanity. All bedrooms feature Juliet balconies, and the flexible third bedroom with glass-paneled walls adapts seamlessly for guests, work, or lounging and features a built in office nook. Additional features include in-unit laundry, one exterior parking space, a newer roof, fee simple ownership with no HOA assessments, and potential Airbnb flexibility. Steps from the lakefront, Top schools Alcott Elementary and Lincoln Park High School, Belmont Harbor, Lincoln Park's trails, Southport cafes and boutiques, and the Brown and Purple Lines, this home delivers unmatched style, privacy, and convenience in one of Chicago's most vibrant communities.

820 W Wolfram Street Unit #F, Chicago

$400,000
4 Beds 3 Baths 12402324 MLS CLOSED Status
Experience the perfect blend of raw-contemporary style and space in this stunning 4-bedroom, 3-bathroom "duplex down" condo in Bronzeville. Spanning an impressive 3,600 square feet, this home features soaring 13-foot ceilings, rich wood floors, and beautifully exposed wood beams-exuding character and warmth. The entire dwelling is bathed in natural light, with floor-to-ceiling windows showcasing architectural interest and an expansive open layout-ideal for entertaining or everyday living. The well-appointed kitchen is complete with a large granite-topped island, ample storage, stainless steel appliances, and an adjoining dining area. The living room features a gas fireplace, beautiful wood flooring, and an open-to-below design revealing the living room below, creating a dramatic double-height ceiling and an abundance of natural light. The spacious primary suite includes a generous walk-in closet and a well-appointed en suite bathroom with double sinks and step-in shower. Two balconies enhance the main level, offering added outdoor living spaces. The fully finished lower level offers two private entrances and features two spacious bedrooms with 13-foot ceilings, a full bathroom with dual vanities, a laundry area, and a flexible living space-ideal for a home theater, fitness room, home office, flex space, or playroom. The expansive lower level, with two separate exterior entrances, offers the potential to be converted into a fully independent living space-ideal for extended family, guests, or as a private unit. Thoughtfully designed with abundant closet space and an assigned parking space, this home meets every need. Ideally located near Lake Michigan, parks, shopping, and schools, with the added convenience of a bus stop on the corner, quick access to public transportation, expressways and downtown, this property is perfectly positioned for convenient living. Guests will appreciate hassle-free street parking and access to public transportation. The building provides each unit with additional dedicated storage space conveniently located on the basement level. Investor-friendly property offering strong potential for long-term leasing - community maintains a no-Airbnb policy to ensure neighborhood stability. Enjoy the richness of culture, history, and community that vibrant Bronzeville has to offer, with proximity to Mandrake Park, Burnham Park, Oakwood Beach (home of the secret mermaid), Lake Meadows Shopping Center, Mariano's grocery store, Lake Michigan, and the Lakefront Trail, 1/2 mile to Bronzeville Dog Park #592, 2 miles to DuSable Black History Museum and Education Center, 1/2 mile to Bronzeville Winery, enjoy live jazz music at Norman's Bistro. Move Confidently!

765 E 41St Street Unit #1A, Chicago

$615,000
2 Beds 2 Baths 12445600 MLS CLOSED Status
Stunning, Rarely Available 2-Bed 2-Bath Duplex-Up Penthouse Unit In Sought After 60657 Lofts Offers An Expansive 16ftx15ft Private Roof Deck With Breathtaking Chicago Skyline Views! Perfectly Located In The Heart Of West Lakeview, Just Blocks From Vibrant Southport Corridor & Charming Roscoe Village, This Boutique Elevator Building Combines Historic Charm With Modern Living. This Spectacular Home Was Just Beautifully Renovated In 2025, With No Detail Spared! Gorgeous Chef's Kitchen Features New Quartz Countertops, Under Mount Sink, Stainless Sprayer Faucet, Refinished White Cabinetry, Decorative Mosiac Tile Backsplash, Brushed Gold Hardware, Over Head Lighting, Custom Shelving & All-New LG Stainless Steel Smart Appliances. Breakfast Bar Seats Up To Three & Flows Seamlessly Into The Open Dining & Living Area, Anchored By A Gas Fireplace - Perfect For Entertaining! Architectural Highlights Include 9FT Ceilings, Painted Exposed Brick & Exposed Ductwork On The Main Floor. West-Facing Wall Of Windows On Both Levels, Drenches Home With Natural Sunlight-Enjoy Gorgeous Sunsets & Peaceful Horizon Views. Upstairs, The Primary Suite Is A Private Retreat: A Massive 17'x13' Bedroom Fits A King Bed & Large Furniture, Has A Spacious Walk-In Closet, Shelving Nook & Extra Storage Cabinet. Enter Through Glass-Panel French Doors To Brand-New, Fully Renovated Spa-Like Primary Bathroom: This Luxurious Space Showcases Custom Tile Work, White Refinished Vanity With Quartz Countertop, Glass Shower Panel, Framed Mirror, Brushed Gold Hardware, Fixtures & Lighting. Access The Private Terrace Directly From Primary Suite, Which Is A Quiet Retreat To Enjoy Your Morning Coffee, Take A Break From Work Or Entertain Over Looking The City Skyline. Exterior Water Spigot Makes Watering Plants & Flowers Very Convenient. Exterior Electrical Outlets. The Spacious Main Floor Second Bedroom Offers Versatility With Pocket Doors At Each Entrance For Privacy. This Nice Size Room Fits A Queen Bed & Has An Additional Area Perfect For A Home Office. A Walk-In Closet Houses The Brand-New LG Washer & Dryer With Ample Closet Space. Gorgeous Renovated Main Floor Full Bath Is Accessible From Hallway Or Via Pocket Door In 2nd Bedroom For An En-Suite Feel. All New Flooring, Tub, Polished Ceramic Subway Tile Surround, Natural Wood Vanity, Lighting, Black Matte Hardware, Fixtures & Mirror All Have A Beautiful Sleek Design. Additional 2025 Updates With This Massive Renovation Include: Entire Unit Freshly Painted, Refinished Hardwood Floors Throughout, New Tile Flooring, New Lighting, Ceiling Fans & Outlets/Switches Throughout. Central Air/Gas Forced Heat. Storage Galore Throughout Unit! Additional Private 8'x4' Storage Cage & Common Bike Area. 1 Deeded, Heated Garage Parking Space Included. The Building Offers 2 Common Rooftop Decks With Unbeatable Skyline & Sunset Views. The West-Side Deck Features Table Seating, Gas Grill, Indoor Prep Kitchen & Bathroom. Enjoy Living Steps From Whole Foods, Target, Trader Joe's. Paulina Market, Starbucks, LA Fitness, CorePower Yoga, Chi50 Pilates, Frasca Restaurant & Bitter Pops. Don't Miss Anthropologie, Lululemon, Vuori, Sephora, Coda di Volpe, Ella Eli, Crosby's, Itoko,Volo & Many More Top-Rated Restaurants, Boutiques & Conveniences Nearby! Paulina Brown Line EL, Ashland & Belmont CTA Bus Lines ALL 1 Block Away. Pet Friendly-Max 2 Dogs & 1 Cat. Investor Friendly-No Rent Cap (No Short-Term Rentals Or AirBnb) Professionally Managed. Strong Reserves. Assessments Include High-Speed Internet & Cable. Massive Renovation In 2025: All New Windows & Slider Replaced(2025), All New Kitchen Appliances/Washer Dryer, Entire Unit Freshly Painted, Floors Refinished, Major Remodel Of Both Bathrooms & Kitchen (2025), Window Treatments (2022),Water Heater (2019). Burley Elementary. Truly Have It All In This Unbeatable Lakeview Location!

1645 W School Street Unit #414, Chicago

$290,000
1 Beds 1 Baths 12395755 MLS CLOSED Status
Attention investors and owner-occupants-welcome to Dearborn Plaza at 545 N Dearborn St, Unit W1602. This spacious one-bedroom, one-bathroom condo features a private balcony and is move-in ready after an upgrade in May 2025. The unit includes brand new stainless steel kitchen appliances-refrigerator, stove, microwave-and a newer dishwasher. The modern, open-concept kitchen with white cabinetry offers ample storage and is perfect for entertaining. Enjoy in-unit laundry, an oversized bathroom with a soaking tub, and flooring throughout, including brand new flooring in the bedroom as of May 2025. The large bedroom that fits a king size bed includes a walk-in closet with built in shelving. Residents enjoy access to 50,000 square feet of resort-style amenities, including a 24/7 door staff, dry cleaner, bike storage, outdoor pool and sundeck with grills, running track, dog run, sauna, fitness center, indoor basketball court, party room, game room, business center, and a library with coffee and computer access. Monthly assessments cover cable, internet, air conditioning, heat, gas, and water-leaving only electricity for the owner. Building reserves was over $2 millions as of December 2024, with no special assessments planned. Rentals are allowed with a minimum 30-day lease, no rental cap, and no Airbnb permitted. On-site parking is available for rent at $350/month through third-party management on the third floor (not owned by the association). The building is pet-friendly with a limit of two pets per unit, up to 25 lbs each. Experience the best of modern, convenient city living-schedule your private tour today.

545 N Dearborn Street Unit #W1602, Chicago

$785,000
4 Beds 3 Baths 12355564 MLS CLOSED Status
INCREDIBLE OPPORTUNITY - 3BR+2BA SINGLE-FAMILY RESIDENCE, PLUS 1BR+1BA MULTI-GENERATIONAL OR RENTAL UNIT (AIRBNB ALLOWED)...OR EASILY CONVERT PROPERTY BACK TO FULL SINGLE-FAMILY RESIDENCE! Nestled among million-dollar homes in the hidden gem of Smith Park in West Town, this one-of-a-kind property offers unmatched flexibility, income potential, and modern comfort. This residence is Airbnb/STR certified by the city and is just 13 minutes from downtown, 8 minutes from the United Center, and steps from the Metra. A thriving neighborhood filled with top-rated dining, coffee shops, and boutique shopping. The top floor unit is a showstopper with 30-ft ceilings, six stunning UV-treated stained-glass-style skylights, and an open-concept living space bathed in natural light. Hardwood floors and soaring ceilings create a grand yet inviting atmosphere. Luxurious primary suite with walk-in and second closet, spa-like ensuite bath with soaking tub and step-in shower. Chef's kitchen, 3 out-door spaces (new grill included), and even a 240-bottle wine area! The ground-floor unit is a bright and spacious 1BR+1BA retreat, ideal for rental income, an Airbnb investment, or an in-law suite. Property boasts newer roof, and newer mechanicals and features. Easy parking with permitted street parking (up to 5 spaces!) and free parking across the street at Smith Park. Enjoy the park's pool, tennis courts, dog-friendly playground, playing fields, walking track, and even chess tables. DON'T MISS THIS RARE FIND - CHCICAGO'S BEST KEPT SECRET!

708 N Rockwell Street, Chicago

$1,088,000
6 Beds 3 Baths 12327379 MLS CLOSED Status
Nestled in Edgewater, a top North Side enclave, 6070 N Hermitage Avenue blends charm, space, and opportunity. On an 8,100-square-foot double lot, this meticulously maintained Victorian is a canvas for your vision: a private sanctuary, lucrative investment, or urban escape. Its versatile layout, outdoor spaces, and prime location shine in a fast-moving market. Step into this three-story home, where each floor offers adaptable spaces suited for multigenerational living, rental income, or extended guest stays. The first floor features a self-contained apartment-freshly painted, rent-ready-with two bedrooms, a bath with walk-in shower, and an updated eat-in kitchen with all-in-one washer/dryer. A third bedroom, now an office, adds flexibility, with hardwood floors and beveled glass accents throughout. The east-facing living room glows with morning light, and a fireplace in the dining room warms chilly evenings. The second floor offers a freshly painted kitchen and living areas-perfect for a pied-a-terre or guest suite-with a second fireplace for chilly summer nights and separate entrances for privacy. The third floor, with its own heat and AC, boasts a stunning large spa bath with a huge walk-in shower and a former kitchen with intact piping. An expansive primary suite, currently an owner's retreat, doubles as a studio or office. This level suits in-law or guest use. Every floor has porches and decks for hosting. An entertainer's dream, unwind on the east-facing front porch, enjoy movie nights on the rear deck, or host lawn parties in the fenced yard with garden and fire pit. Two decks offer escapes, lush landscaping an oasis. A three-car garage, two parking pads, zoned street parking, and alley access add convenience. Lovingly maintained by the same owners for 29 years, this property features updated kitchens, baths, hardwood floors, modernized electrical/plumbing, new third-floor furnace, refreshed decks, rebuilt porch, solid garage, and maintained foundation, roof, and gutters. Distinctive lighting, custom cabinetry, and painted trim add warmth. With separate utilities, this legal two-unit offers flexibility-live in one, rent the other. The third floor enhances multi-generational or leisure space. Window units, mounted TVs, and appliances (dishwasher, fridge, microwave) make it Airbnb-ready. Basement coin laundry adds revenue, relocatable if desired. Adaptable for owner-occupant income, long-term, or short-term rentals, it promises returns on a rare city lot. Steps from the new Petersen/Ridge Metra station, near CTA Red Line and Lake Shore Drive, it's commuter-friendly with Foster Beach, Sheridan Road shopping, and dining nearby. Edgewater balances urban ease and charm, and this property's size and condition set it apart in a rising market. Its welcoming energy invites memories. Professional photos spark possibilities-homeowner haven, investor gem, or visionary reimagining. In dynamic Edgewater, this opportunity won't last. Seize it!

6070 N Hermitage Avenue, Chicago

$475,000
2 Beds 2 Baths 12317418 MLS CLOSED Status
Beautiful vintage courtyard building located on a quiet, tree-lined street in East Lakeview/Nettlehorst School District. This vintage 2 bedroom, 2 bath duplex unit is a rare find in this highly sought after building. Flexible floor plan w/spacious room sizes, either bedroom can be used as primary. Recently remodeled bathrooms and kitchen, featuring BRAND NEW SS appliances & quartz countertops, this unit is sure to impress. Other amenities include in unit washer/dryer, all rooms with freshly painted walls and ceilings and NEW blinds, lighting and two (2) window ac's. The main floor features 9' ceilings, newly refinished hardwood floors, a beautiful vintage limestone mantle, new light fixtures throughout the unit. The lower level features brand new hardwood looking ceramic tile and renovated full bathroom with new vanity and toilet. Easy street parking and rental options complete this home. HOA includes heat, cable and internet. Additional basement storage available. Located just steps from the lakefront with tennis courts, golf course, bike trails and running paths. Excellent transportation 1 block away, buses to downtown, red line and Addison bus to the blue line offers an easy commute to O'Hare. Lakeview is a lively, sought-after neighborhood with plenty of cool shopping, restaurants and nightlife venues within walking distance! Jewel/Osco and Whole Foods are 2-blocks away and Wrigley Field is within cheering distance! Truly a great walking neighborhood. Don't miss this one, it won't last long! Pack your bags and move right in! Investor friendly building. NO Airbnb.

550 W Brompton Avenue Unit #1S, Chicago

$840,000
4 Beds 3 Baths 12257473 MLS CLOSED Status
Stunning, updated 4 bedroom, 2.1 bath, brick townhome in the heart of Lincoln Park and the center of DePaul University. This townhome in the Oscar Mayer School district enjoys a great floor plan featuring hardwood floors throughout the spacious combined living room/dining room. The gas fireplace and sliding glass doors opening to a very large, east-facing, private brick patio make it ideal for entertaining or every day indoor-outdoor enjoyment! The chef's kitchen boasts granite countertops, stainless steel appliances, ample storage and adjoining breakfast area for casual dining. Retreat to the second floor to find two king sized bedrooms with new carpeting, plenty of closet space, bath with new tub and laundry area with full size washer and dryer. There are two additional generous bedrooms on the newly carpeted third floor, including the luxe primary suite with fireplace, huge walk-in closet, dressing area and tasteful bath. The additional room is ideal for a fourth bedroom, office or nursery. Furthermore, in 2024, the owner added New carpeting on the second and third floor, New indoor paint, All New lighting fixtures, New second floor tub, New glass in both sliding doors. The driveway off the alley leads to an assigned private parking space. With the investor-friendly policies, this home offers flexibility and value. There are No assessments, No HOA and No rental restrictions. Perfect for a Private Home, an Investment or an Airbnb! Rare find in one of Chicago's most vibrant neighborhoods: walk-to shops, restaurants, park and train. Location, Space, Comfort and Beauty!

2220 N Kenmore Avenue Unit #A, Chicago

$285,000
2 Beds 2 Baths 12303617 MLS CLOSED Status
Bright and modern, this beautifully updated 2-bedroom, 2-bath condo offers stylish city living in Chicago's vibrant Tri-Taylor neighborhood, just steps from the Blue Line and minutes from the Illinois Medical District. Designed for both comfort and convenience, the open-concept layout features a recently remodeled kitchen, a spacious living and dining area, and solid hardwood floors throughout. The expansive primary suite easily accommodates a king-size bed and includes a spa-like en-suite with a tub, walk-in shower, and ample built-in storage. A spacious second bedroom, generously sized closets, in-unit laundry, and a south-facing balcony overlooking Claremont Park complete this fantastic home. From 2022 to 2023, the property operated as a highly successful Airbnb, generating an average of $43K per year. With a short-term rental-friendly HOA, this is an exceptional opportunity for investors or those seeking a flexible living space. Additional updates include a newer furnace (2017), AC (2020), hot water tank (2018), refrigerator (2021), dishwasher and microwave (2022), LG washer/dryer (YEAR TBD), and freshly repainted exterior staircase (2024). Situated in a prime location near the CTA Blue Line, I-290 expressway, UIC, Rush University Medical Center, and the UIC Medical District, this home offers unbeatable convenience and accessibility. ***One owner is a licensed real estate broker in the state of Illinois, but is not the listing agent of the property.***

2337 W Harrison Street Unit #3, Chicago

$900,000
2 Beds 4 Baths 12189106 MLS CLOSED Status
Incredible opportunity to benefit from the tireless transformation by the current owners of this historic home in West Ridge into a case study on modern design and luxury living. Turn-key does not come close to describing the extent to which this bright 3 bedroom, 4 bath brick bungalow on an oversized corner lot has been improved. The entire exterior envelope of the home has been faithfully restored with high-end replacement windows, restorative masonry and a brand new Euroshield eco-friendly rundle slate roof. The landscaping and hardscaping are professionally designed with underground sprinklers and a recently redesigned yard with luxury pavers and privacy fencing. Step inside to be greeted by the bright and spacious living room with south and east exposures and a direct vent gas fireplace. Moving down the central hallway, you will find a bedroom and bath on one side and the self-contained primary suite on the other; with a well organized walk-through closet, built-in laundry and a true spa double-vanity ensuite bathroom with separate waterfall soaking tub and steam shower. Continuing on, you arrive at the open concept kitchen, dining and sunroom area of the home, also bathed in light from the continuous wall of windows on the south and west exposures with an oversize picture window facing north over one of the sinks. This is a great entertaining space as guests lounge in the sunroom area while the meal is prepared. The chef's kitchen contains high-end 48" Wolf range with four burners, a French top and a 48" hood with a 1500cfm blower, a Liebherr refrigerator/freezer/wine cooler combo, a Miele dishwasher and two oversized undermount sinks over a combination of quartzite and silestone counters with designer cabinetry, plumbing and lighting fixtures. And this is only half the house! The lower level has been completely renovated and comprises a fully separate and highly sought after luxury one bedroom AirBnB apartment/suite that is booked without fail any and every time it is made available. The other half of the lower level contains additional living quarters for the owners, including family and bonus rooms heretofore used as an art studio/ home office and a large steam room with adjoining bathroom. It should come as no surprise that the mechanicals are all modern and state of the art with: underfloor radiant hot-water on demand heating, SpacePak cooling, built in speakers and sound system, comprehensive home security system and a host of other accouterments that are best seen in person! The home is located within a short walk to the Rogers Park Metra station, buses, trains, Evanston, Lake Michigan and Lake Shore Drive to bring you into downtown Chicago.

7050 N Ridge Boulevard, Chicago

$765,000
3 Beds 3 Baths 12276754 MLS CLOSED Status
NEED MORE SPACE? 2500 square foot duplex up for sale in Prime Old Town! Walk to Lake Michigan, Wells Street, Topo Gigio, Foxtrot, Pete's Coffee/Starbucks, Magnificent Mile, Lincoln Park Zoo and Farmer's Market. Sought after private schools within a couple blocks include Catherine Cook and Immaculate Conception ( Latin School is about a 10 minute walk) Tons of light, windows and privacy in this penthouse corner residence. Three generous bedrooms, all with Hunter ceilings fans, three full bathrooms with marble and terrazzo and all have heated floors. Two family rooms, one on each floor. 3 outdoor spaces with upgraded, maintenance-free composite decking. Gorgeous white kitchen with glass fronts and upper cabinets, wine storage, stunning dark granite counters and island, stainless steel appliances, adjacent pantry, and a window over the kitchen sink! A living room and dining area on the main floor, gas fireplace, built in book cases and custom window seat with storage. Soaring ceilings, ornate crown molding and baseboards, LED lighting throughout, and custom stain glass transoms atop each door frame. Rich walnut-stained authentic oak hardwood floors throughout and just installed new carpet in all the bedrooms. Oversized closets and storage throughout the home. The master suite has wall to wall custom closets, an attached Terrazzo spa bath, a concealed jewelry box, and it steps out to a south facing balcony with clear views of the Sears tower and the entire Chicago skyline. Upstairs find an additional family room already equipped with a stunning mahogany billiard table, side by side laundry closet, and an additional guest bedroom and bathroom. This home is loaded with upgrades and although built in 1996, everything has been upgraded since including: electric, Anderson windows and sliding doors, all Kohler plumbing fixtures, blown in cellulose insulation in every wall, a whole house fan, new water heater (2025), and new HVAC from 2009. ATTACHED garage parking and additional storage included in the price. The building has two guest parking spots available upon reservation, no rental cap, super high reserves (ask me for the amount). AIRBNB FRIENDLY ( ASK ME THE RULES FOR RENTALS).

325 W Schiller Avenue Unit #3W, Chicago

$295,000
1 Beds 1 Baths 12265363 MLS CLOSED Status
Gorgeous pool/plaza views from this beautiful, south-facing, perfect one bedroom with office space--Plus, a large balcony off of the living space overlooking the pool/plaza/city for morning coffee, grilling, or enjoying a sunset. Fresh paint, gorgeous white 42" kitchen cabinetry, new black pull handles, soft close doors, lazy susan, pullout garbage/recycling, granite countertops, stainless steel appliances (gas oven/cooktop, refrigerator, dishwasher and microwave), and new under cabinet lighting. Wide-plank, Hickory pre-finished Hardwood flooring throughout-2022. Pretty, new lighting throughout-2023. Double closet at entry. Sharp bathroom. Bedroom comes with drapery and a double closet--it will fit a king-sized bed, dresser, and 2 nightstands. Assessments include: Heat, Cable (Astound/RCN with Tivo/Wifi), Internet/600MB, Cooking Gas, Water, Garbage/Recycling, Reserves/Savings. Building has it all: gorgeous outdoor pool, plaza with water feature, workout room, 24 hr doorman, 24 hr maintenance, onsite management (M-F), drycleaner/Amazon hub/receiving room, rooftop laundry with an app to check machines/vend, rooftop deck, and a fabulous party room. Free wifi in party room, pool, and laundry area. No additional fees for workout room, pool, or party room (unless booked for a private party). Bus lines: 22, 36, 151, 156, and 73 are across the street. Divvy bikes-50 ft away. Lincoln Park, Nature Boardwalk, LP Zoo, North Ave Beach, Green City Farmer's Market, and more are just across the street. Stroll to all the great restaurants & shops in Lincoln Park & Old Town. Approx 4 Mil in reserves, cash, & operating accts. Investor friendly. No short term rentals/airbnb/vrbo/etc allowed. All leases must be 1 yr min. Pet friendly with NO weight restrictions. Free and zoned neighborhood parking. (You may be able to find garage rental through other owners in our building for approx ~275/mo) Carpe diem!

1960 N Lincoln Park West Unit #406, Chicago

$2,000,000
2 Beds 3 Baths 12193221 MLS CLOSED Status
This is a RARE beauty right at the intersection of Boystown and Wrigley! This building was TRANSFORMED in 2018 - beautifully designed full-lot commercial space on the main floor and just up the stairs is a STUNNING loft style home that added an additional TWO floors! Perfect for a small business live/work dream, in the middle of it all with a large footprint and your own private residence with over 1,000 additional sqft of outdoor living! Or rent the 2,600 sqft ground level commercial for great passive income on this lowered property tax mixed use gem. Just upstairs, enter into the large living space which boasts TONS of room to spread out in your very own city oasis. This home is LUXURIOUS, a beautifully designed mix of old and new Chicago - industrial steel juxtaposed with antique oak doors - decked out with HIGH quality details in every finish and addition. Note the 22 foot ceilings and huge custom wall of sound and weather insulated windows! From the living room you have access to one of your many outdoor spaces, your private balcony overlooking the strip. The open kitchen is a chef's dream - stainless steel appliances throughout, a Wolf six burner range, and full pantry are notable additions to this carefully curated residence. Just down the hall you have access to your SECOND private outdoor space: a sprawling Trex roof deck with hot-tub reinforcement! Up the stairs is your loft style primary suite that features your THIRD outdoor space, an additional balcony. This sprawling bedroom features a big walk-in closet, sleek hardwood floors, and access to your SHOWSTOPPING ensuite bathroom that features a Signature Hardware cast iron clawfoot bathtub, Kingston Brass bathroom features, as well as your washer and dryer. Other notable features of the residence include a beautiful second bedroom and bath, Johnathan Adler chandelier, smart light switches, and a sprinkler system that runs not only through the commercial space BUT ALSO the residence as well. The split bedroom layout is PERFECT for someone who likes to host OR lucrative Pride/Cubs AirBnb potential! The detail oriented ground level commercial is turnkey for a pet friendly business in a very pet friendly neighborhood. This can also be VERY easily reconfigured to several other business ventures with the desirable flexible C zoning. SPACE is the name of the game! Commercial spans the 25x122 lot footprint. Original parking converted to additional commercial square footage can be swapped back at new owner's choosing. Located on Halsted near Addison, this mixed-use building is steps from CTA routes, grocery, restaurants, and several highly beloved community hubs in an extremely walkable area.

3524 N Halsted Street, Chicago

$247,000
1 Beds 1 Baths 12162209 MLS CLOSED Status
Bright and spacious top-floor 1 bedroom, 1 bathroom condo located in highly desirable Graceland West. This unit offers abundant natural light from east and west-facing windows, providing beautiful treetop views. The kitchen features ample storage with 42" cherry Shaker cabinets, granite countertops, and newer stainless steel appliances, 3-stage water filter, along with a separate dining area. The open layout allows for distinct living and dining spaces, as well as room for a home office. The large bedroom, complete with a walk-in closet, is conveniently situated next to the full bathroom. Hardwood floors run throughout the unit, which also includes custom Levelor blinds, a Carrier HVAC system with central A/C replaced in 2023, in-unit laundry, a sizable storage unit, and bike storage. Enjoy the building's well-maintained and beautifully landscaped courtyard, equipped with seating and grills. The association is financially sound, with a new roof installed in 2022 and recent masonry work as well. This pet-friendly building is approximately 65% owner-occupied but allows rentals (excluding short-term or Airbnb), and offers ample and easy street parking (zoned during night games and events). Located steps from the top of the vibrant Southport Corridor, the home is close to both the El and Metra, restaurants, Target, Jewel, Wrigley Field, and so much more. Enjoy the best of city living in a quiet, residential neighborhood. Professional photos coming soon.

4302 N Clark Street Unit #3, Chicago

$600,000
3 Beds 2 Baths 12129512 MLS CLOSED Status
This exceptional corner lot residence boasts distinctive features, including a spacious private yard-an ideal canvas for creating your own urban sanctuary. The open-concept living and dining area showcases 11-foot ceilings, expansive picture windows, and fresh quartz countertops complemented by ample cabinet space and a large island, creating a perfect setting for entertaining. The generously sized guest room features a beautifully renovated second bathroom with a walk-in shower. The primary bedroom's en suite is equipped with a spacious tub, a full walk-in shower, a toilet room, and double vanities. On the same level, the third bedroom offers flexibility-it can be divided into two bedrooms or serve as a versatile space for a second living area, office, gym, and more. Throughout the entire home, upgraded lighting, recent paint, nearly new custom window treatments, and hardwood floors add to its appeal. Notably, this residence is a must-see, with no HOA fee and investor and AIRBNB-friendly policies. Additional storage is available under the stairs, and two sheds in the yard will remain for the buyer, providing an ideal solution for outdoor activities. Conveniently located just one block away from Scofflaw, Giant, the Way Out, Damn Fine Coffee, and all that Armitage has to offer. Plus, it's a quick 10-minute drive to the highway and less than a 15-minute walk to the Blue line! Take a 3D Tour, CLICK on the 3D BUTTON & Walk Around. Watch a Custom Drone Video Tour, Click on Video Button!

1857 N Sawyer Avenue Unit #A, Chicago

$430,000
2 Beds 2 Baths 12024428 MLS CLOSED Status
Beautiful vintage courtyard building located on a quiet, tree-lined street in East Lakeview/Nettlehorst School District. This vintage 2 bedroom, 2 bath duplex unit is a rare find in this highly sought after building. Flexible floor plan w/spacious room sizes and the ability to use either bedroom as your primary bedroom. A recently remodeled bathroom and kitchen, featuring quartz countertops, SS appliances, this unit is sure to impress. Other amenities include in unit washer/dryer, electric smart blinds, Lutron Caseta smart home switches in most rooms. The main floor features 9' ceilings, hardwood floors, a beautiful vintage limestone mantle, new light fixtures throughout the unit, and 3 entrances. Easy street parking and rental options complete this home. HOA includes heat, cable and internet. Additional basement storage available. Located just steps from the lakefront with tennis courts, golf course, bike trails and running paths. Excellent transportation 1 block away, buses to downtown, red line and Addison bus to the blue line offers an easy commute to O'Hare. Lakeview is a lively, sought-after neighborhood with plenty of cool shopping, restaurants and nightlife venues within walking distance! Jewel/Osco and Whole Foods are 2-blocks away and Wrigley Field is within cheering distance! Truly a great walking neighborhood. Don't miss this one, it won't last long! Pack your bags and move right in! Investor friendly building. NO Airbnb.

546 W Brompton Avenue Unit #1S, Chicago

$355,000
1 Beds 1 Baths 12003731 MLS CLOSED Status Fairbanks At Cityfront BLDG.
Sophisticated Loft Living in the heart of Streeterville. 10' 6" Ceilings. Private deck facing south. Open flexible floor plan. Enjoy hardwood floors, a gorgeous kitchen with Italian cabinets, granite countertops, stainless appliances, and a deep sink. Fantastic work-at-home office nook. Barn doors lead to the spacious bedroom with a walk-in closet and modern bathroom. In-unit laundry room. LEED Gold building. High speed elevators. 2 State-of-the-Art Fitness spaces. Large resident only Dog Run. Contemporary party room, business center and theater. South-facing outdoor pool, sundeck and gardens on a beautifully, landscaped terrace. 24-hour door staff in an elegant lobby. Onsite management, engineering team and dry cleaner in the building. Whole Foods downstairs. Egg Harbor next door. Conveniently situated between Michigan Ave., the Lakefront, Navy Pier, Ohio Street Beach and the Chicago River. Restaurants, shopping, nightlife, and entertainment galore. Walk to Foxtrot, Target, Trader Joes, AMC River East and Lucky Strike. Nearby I-90/94, Wacker Dr. and Lake Shore Dr. Monthly assessment includes all utilities (and Internet Zentro 500mbps up and down and Direct TV) but electricity. Pet (2 dog max. 1st dog - no weight limit. 2nd dog - 40 lb. max.). Investor Friendly. AIRBNB prohibited. One secure, attached, deeded parking space - extra 20K. External Storage locker included. Furnishings available for an additional cost.

240 E Illinois Street Unit #504, Chicago

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Chicago, IL · Curated MLS Search

Airbnb-Friendly Homes in Chicago, IL

An editorially curated view of every active airbnb-friendly homes listing in Chicago, IL. Updated in real time from the local MLS, presented without the noise.

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