View All Uptown Chicago IL Homes with Bonus Room Listings

$799,000
3 Beds 2 Baths 12752054 MLS NEW Status
This impeccably maintained 3-bedroom, 2 bath penthouse pairs sophisticated modern design w/ exceptional private outdoor space in the heart of Uptown! Soaring 11' ceilings & oversized windows flood the home w/ natural light. Hardwood flooring throughout, 8-foot solid core doors & clean architectural lines create a contemporary feel throughout. The sleek European kitchen is a chef's dream, featuring integrated panel refrigerator & dishwasher, Thermador/Bosch appliances, white quartz countertops, marble backsplash, under cabinet & pendant lighting, & a generous breakfast bar w/ seating for four. The expansive open concept living and dining space is fantastic for entertaining, anchored by a striking custom fireplace & opening directly to a private terrace w/ gas hookup for a grill. The serene primary suite provides ample room for a King-sized bed, professionally organized walk-in closet, & a luxurious primary bathroom w/ heated porcelain floors, a floating double vanity & an oversized walk-in shower w/ a rain head. Two guest bedrooms, a beautiful hall bathroom, & a huge laundry closet with side-by-side Whirlpool washer/dryer set complete the main living level. The full-floor rooftop is a true urban oasis w/ panoramic city view, pergola & fire pit, contemporary planters, irrigation, & artificial turf. Adjacent to the roof deck is a bonus room that would make an ideal office or workout space. This boutique, seven-unit building is professionally managed with a spacious garage w/ bike storage. Walk to the Lake, Aragon Ballroom, Green Mill, Lawrence and Argyle Red Line "L" stations, and so much more!

4858 N Kenmore Avenue Unit #3N, Chicago

$560,000
2 Beds 2 Baths 12572174 MLS CLOSED Status
***MULTIPLE OFFERS RECEIVED. HIGHEST AND BEST CALLED FOR BY MONDAY, FEBRUARY 23RD @ 12 NOON. NO ESCALATION CLAUSES OR LOVE LETTERS.*** Nestled on a one-way street in Uptown is this rarely offered end-unit townhome. Featuring 2-3BR's, 1.1BA's, and an attached 1 car garage, this lives more like a single family home, and offers 3 sides of light and exposure. Inside the main level features an open concept living/dining/kitchen space with newly refinished hardwood floors, new recessed lighting, plus a powder room on this level. The kitchen has ample cabinet storage, all newer appliances, and expansive counter space for entertaining, meal prep, and bar seating. The living room has two Juliet balconies to allow for beautiful sunsets and spring breezes to fill the space, and the kitchen leads to a balcony perfect for grilling. Upstairs are two generously sized bedrooms with brand new carpet and a full wall of closets in each room. The primary bedroom can easily accommodate a king size bedroom set, and the 2nd bedroom leads to a balcony space overlooking the backyard. Speaking of the backyard--YES, a full fenced-in BACKYARD!!! The ground level has in-unit laundry, and a bonus room that could be used as a rec room/3rd bedroom or office, and has sliding doors that lead to a custom designed "Catio" for those with four-legged friends who want to enjoy the outdoors. The backyard is beautifully landscaped with brick pavers, and is the perfect space to spend magical evenings dining al fresco, and space to start a garden. Of the five townhomes in the association, this one has the largest yard! Across the street is the Winthrop Family Community Garden, offering a beautiful landscape to gaze upon from the living room and primary bedroom, and rest assured with the peace of mind that it can never be built on! This pocket of Uptown offers convenience to dining and nightlife, with restaurants like Lucy's, Stan's Donuts, and plenty of excellent restaurant options on Wilson Avenue. Catch a jazz show at Green Mill Tavern, the Riviera, or Aragon Ballroom just two blocks to the north. Public transit is simple with the newly renovated CTA Wilson Red and Purple Line Stations around the corner, and plenty of bus options on Broadway and Lawrence Avenues, plus easy access to Lake Shore Drive via the Wilson on/off ramps. Enjoy summers at the beaches of Lake Michigan, or the Lakefront Trails, just at the end of Wilson Avenue!

4633 N Winthrop Avenue, Chicago

$1,425,000
3 Beds 4 Baths 12543415 MLS CLOSED Status
Meticulously maintained and built in 2008, this stunning Andersonville residence blends luxury, space, and an unbeatable location. Inside, you'll find walnut floors throughout, a chef's kitchen with rich walnut cabinetry, stainless steel appliances, honed granite countertops, a spacious island, and an oversized walk-in pantry-perfect for entertaining or everyday living. The sun-drenched interior features soaring ceilings and oversized windows on every level. The second floor offers three generously sized bedrooms, including a luxurious primary suite with a spa-like marble bath featuring a steam shower, rain shower head, whirlpool tub, and custom-built closets. A second-floor laundry room adds everyday convenience. The lower level expands your living space with an additional bedroom and full bath featuring double sinks and a tub-ideal for guests or extended family. There's also a spacious bonus room complete with a dry bar and beverage center, plus radiant heated floors and a second laundry area. Modern comforts abound: dual-zoned HVAC, gas fireplace, surround sound wiring, and recent updates including new roof, tuckpointing, and parapet (2024), chimney recapped and sealed (2024), and newer furnaces (2023). Outdoor living is just as impressive with a private roof deck featuring composite decking, a landscaped backyard with newer paver patio, and an attached 2-car garage with a radiant heated driveway. All of this in a prime Andersonville location, just half a block from Clark Street's vibrant shops and restaurants, close to the CTA, El, Metra, Mariano's, parks, and only 3/4 mile to the lake.

1433 W Winnemac Avenue, Chicago

$575,000
2 Beds 2 Baths 12484801 MLS CLOSED Status
Spacious & bright, 2 bed, 2 bath Andersonville penthouse, perched among the trees with private roof deck! This intelligently designed home features a stunning great room with 10-foot ceilings: handsome kitchen with rich cabinetry, crisp white quartz counters, stainless steel appliances & breakfast bar, connected to dining area and large living room (with wood burning fireplace) plus a private balcony - the first of 3 outdoor spaces. The real star is the private roof deck - 1 flight up, with tree-top views and plenty of space for outdoor fun. Movie Night? Check. Dinner Party? Check. Sunbathing? Check! The list goes on! Back inside, enjoy king-sized primary suite with large, organized walk-in closet and attached bath with double sinks and shower with body sprays. There's also a sizable guest bedroom that easily fits a queen-sized bed, and with large window is perfect as a home office combination, with adjacent full bath for your guests. Bonus coffee bar area (with dual wine & beverage fridge) off the kitchen leads to your grilling balcony & rear stairs, that take you to your assigned parking space and basement storage unit. Hardwood floors, crown molding, central air/heat plus in-unit laundry complete this well-maintained home. A+ location convenient to brand-new CTA Red Line stop and Clark Street dining/shops/nightlife, with easy access to gyms, coffee shops, Lake Shore Drive/lakefront...everything that makes Andersonville one of the best neighborhoods to call home!

1313 W Carmen Avenue Unit #3N, Chicago

$520,000
2 Beds 2 Baths 11980104 MLS CLOSED Status
Gorgeous 2 bed + office + sunroom 2 bathroom condo in Andersonville within walking distance of tons of fantastic shops and restaurants.This corner condo is exceptionally bright and sunny with windows on three sides! The 1400 square foot condo is located in a classic center entrance vintage Chicago building on sought after Winnemac Street. Large living room with tons of windows and a bonus sunroom (currently being used as a formal dining area which can fit a table for 10). The fully updated eat-in kitchen has white cabinets, stainless steel appliances, quartz counters, a pantry closet and leads to a spacious private deck, perfect for dining or lounging. Very large primary suite which easily fits a king sized bed, has two closets including a walk in closet, and an attached fully updated primary bathroom. The second bedroom was massive so it was divided into two rooms - a smaller second bedroom and a separate office although you could remove the wall and turn it back into a massive second bedroom if you'd prefer not to have a separate office area. This condo features great storage space with a coat closet, linen closet, pantry, laundry closet with side by side laundry which has additional storage space, bike storage in the basement and not one but two storage areas in the basement just for this unit. Professionally organized closets and hardwood floors throughout. Completing this property is 1 exterior parking space. Well run HOA with good reserves. Amazing location! Walk to the Lake, Foster Beach, Montrose Beach, Winnemac Park, coffee shops like La Colombe, restaurants like Hopleaf and Big Jones, all of the festivals and events in Andersonville and more. Tons of transportation options - 5 minutes to the Argyle Red Line stop, multiple bus lines nearby or hop on 90/94 or Lake Shore Drive.

1317 W Winnemac Avenue Unit #1, Chicago

$900,000
4 Beds 4 Baths 11938677 MLS CLOSED Status
Incredible indoor and outdoor living spaces in this fabulous duplex down condo located on a quiet, tree-lined street in the heart of Andersonville. This all brick, newer construction three unit condo building was built in 2018, everything looks brand new! The light-filled, spacious open floor plan on the main level includes the living room, dining room, bar area, kitchen, powder room, and large family room area. Hardwood floors and high ceilings throughout the entire main level. There are gorgeous custom shelves flanking both sides of the fireplace in the family room, and a custom built-in bench perfect for seating/table space in the eating area . The amazing, contemporary, chic, chef's kitchen is a delight with high end appliances, opening to the spacious family room area - perfect for entertaining and everyday living. The lower level, with wonderful high ceilings, offers four good-sized bedrooms and three full baths. Additionally you will find so much closet and storage space throughout the condo. A terrific bonus - radiant heated floors throughout the lower level! Incredible outdoor spaces including a large front deck off the living room, a large, private deck off the family room, and a huge private garage roof deck. One garage parking space included, along with a storage space. Easy, plentiful street parking for additional vehicles or guests. Wonderful location in Andersonville, easy walk to restaurants, shops, and transportation. Move right in - this is a 10!

1355 W Winnemac Avenue Unit #1, Chicago

$650,000
7 Beds 4 Baths 11927122 MLS CLOSED Status
Location, Location, Location!!! Nestled in the Heart of Uptown Chicago! This classic red brick 3-Flat building is on an Oversized Chicago lot 33 x 142 feet, presents a Unique Opportunity for both Renovation Enthusiasts and Crafty Investors! RT-4 Zoning, whether you envision it as a Restored Religious Congregation, lovely 3 story Single Family, or an incredible rehabbed incoming generating opportunity, this uptown Gem is a Blank Canvas ready for its Next Chapter! Property is being sold "As Is". 1st and 2nd floor units features living rooms and kitchens. Hosting 2 bedrooms and 1 full bathroom in the first floor and 5 bedrooms and 1 full bathroom on the second floor. 3rd floor is very spacious open floor loft with a balcony and an additional bonus room. Full finished basement have 2 half baths, plenty storage spaces with washer and dryer. The adjacent parking lot to the building provides about 16 exterior parking spaces. Just steps away from red line public transit, just blocks away from Lake Michigan and Lake shore Drive. Walking distance to the schools, grocery stores, restaurants, and nightlife entertainment (Aragon Ballroom, the Riviera Theater and more.) This is walker's paradise. Bring your creative ideas to this Blank Canvas, full of so many potentials and enjoy all the goodness this neighborhood has to offer. PLEASE NOTE THAT THIS BUILDING HAS TO SELL WITH THE PARKING LOT LAND NEXT TO IT total of 66 x 142. (4718 N Winthrop Ave with a different price $550,000).

4716 N Winthrop Avenue, Chicago

$630,000
3 Beds 2 Baths 11913763 MLS CLOSED Status
LAST PENTHOUSE REMAINING! Announcing seven exceptional, new construction condominiums in the exciting, rapidly-emerging East Andersonville/Uptown locale! Smart functional layouts that appeal to today's lifestyles! Unit 3S is a premium penthouse with interior stairs to a bonus room and PRIVATE, ENORMOUS roofdeck - BREATHTAKING VIEWS! We also offer several different floorplans; from 3 bedroom/2 bath simplexes, 3 bedroom/2.5 bath duplex homes and one 4 bedroom/2.5 bath duplex with an atypical, extra-wide unexpected design! You'll enjoy expansive outdoor spaces, via front-facing terraces, large decks and Penthouses that feature the highly-coveted private roofdecks accessible directly from interior stairs! Each residence is appointed with premium finishes, many of which can still be selected by Buyers to make the home their own! Stately building stands tall on a gorgeous one-way, tree-lined street! Stroll up the block to the quaint, cobble-stone lined Argyle Street to enjoy neighborhood favorites like the highly acclaimed Milly's Pizza or First Sip Cafe or enjoy true flavors of authentic ethnic cuisine! All the major retailers such as Mariano's, Whole Foods and Target ultra-conveniently nearby! A few blocks east is the most beautiful strip of lakefront beaches, parks biking and miles of jogging and biking paths! A short trip to the ultra-popular Andersonville strip! Grab the L or take the newly-resurfaced DuSable LSD straight downtown! Come take a look, fall in love and pick your home! Delivering soon! Photos are of staged unit 3N

4932 N Kenmore Avenue Unit #3S, Chicago

$634,000
3 Beds 2 Baths 11903347 MLS CLOSED Status
Announcing seven exceptional, new construction condominiums in the exciting, rapidly-emerging East Andersonville/Uptown locale! Smart functional layouts that appeal to today's lifestyles! Unit 3N is a premium penthouse with interior stairs to a bonus room and PRIVATE, ENORMOUS roofdeck - BREATHTAKING VIEWS! We also offer several different floorplans; from 3 bedroom/2 bath simplexes, 3 bedroom/2.5 bath duplex homes and one 4 bedroom/2.5 bath duplex with an atypical, extra-wide unexpected design! You'll enjoy expansive outdoor spaces, via front-facing terraces, large decks and Penthouses that feature the highly-coveted private roofdecks accessible directly from interior stairs! Each residence is appointed with premium finishes, many of which can still be selected by Buyers to make the home their own! Stately building stands tall on a gorgeous one-way, tree-lined street! Stroll up the block to the quaint, cobble-stone lined Argyle Street to enjoy neighborhood favorites like the highly acclaimed Milly's Pizza or First Sip Cafe or enjoy true flavors of authentic ethnic cuisine! All the major retailers such as Mariano's, Whole Foods and Target ultra-conveniently nearby! A few blocks east is the most beautiful strip of lakefront beaches, parks biking and miles of jogging and biking paths! A short trip to the ultra-popular Andersonville strip! Grab the L or take the newly-resurfaced DuSable LSD straight downtown! Come take a look, fall in love and pick your home! Delivering soon! Photos are of actual staged unit 3N

4932 N Kenmore Avenue Unit #3N, Chicago

$445,000
2 Beds 3 Baths 11876556 MLS CLOSED Status
In sought-after Andersonville, this recently constructed two-story duplex, boasting ultra-high 10-foot ceilings, provides an optimal and streamlined design for social gatherings and daily living. Every room and surface in this home has undergone meticulous enhancements. The kitchen has been entirely remodeled, taking full advantage of the expanded window area. This intelligent design ensures a continual stream of natural light for the kitchen. An all-wood accent wall not only offers an organic contrast but also provides ample storage space. Equipped with stainless appliances, a Wolf gas range, a hood vent, and bar seating for four, this kitchen exudes magazine-worthy aesthetics. Lighting throughout the unit has been added and refined, ensuring a warm ambiance at any hour. The living room, accentuated by its expansive corner setting, is bathed in natural light and anchored by a striking floor-to-ceiling fireplace. Flanking the living area are options for both indoor and outdoor dining. An elegant dining room effortlessly merges with the living and kitchen areas, while the expansive south-facing deck extends the living space outdoors, epitomizing indoor-outdoor living. The duplex design distinctively separates the bedrooms, ensuring a peaceful retreat. Each bedroom boasts spacious, fully customized walk-in closets and abundant natural light. All bathrooms embody contemporary elegance and have been freshly revamped. A bonus: external storage and one designated parking spot are included in the price. This duplex is situated in a contemporary, boutique 5-unit building-currently fully owner-occupied-it's evident this building is impeccably maintained. This unique property is a mere stroll away from the Red Line, lakefront running and biking trails, various parks, Chicago's finest and most diverse restaurants and bars, and eclectic shops; this is the vibrant community spirit that Andersonville has become famous for!

1313 W Carmen Avenue Unit #1S, 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.

Uptown, Chicago IL · Curated MLS Search

Homes with Bonus Room in Uptown, Chicago IL

An editorially curated view of every active homes with bonus room listing in Uptown, Chicago IL. Updated in real time from the local MLS, presented without the noise.

Browse Active Listings