View All Uptown Chicago IL Homes with Double Island Listings

$774,900
3 Beds 3 Baths 12754804 MLS NEW Status
VACANT AND READY FOR A NEW OWNER! This truly expansive 3-bedroom, 3-bath duplex-down with low monthly assessments and one garage parking space-all in a desirable Uptown location. The bright, open main level features hardwood floors, a generous living and dining area, and a fireplace surrounded by windows and French doors. The kitchen offers white cabinetry, granite countertops, stainless-steel appliances, a center island, abundant storage, and a new refrigerator. Two spacious bedrooms and two full baths are located on the main level, including a large primary suite with excellent closet space and private bath. A covered, oversized rear deck provides the perfect setting for outdoor dining and entertaining. The HUGE lower level significantly expands the home's living space with new carpeting, a second fireplace, an enormous recreation and media area, third bedroom, full bath, in-unit laundry, and oversized private storage. The flexible floor plan easily accommodates guests, a home office, fitness area, or separate living space. Additional highlights include a new A/C unit, central heating, and garage parking. Enjoy convenient access to the lakefront, beaches, parks, public transportation, shopping, dining, and the new neighborhood Trader Joe's planned for October 2026. Tremendous space, low monthly assessments, valuable updates, private outdoor space, and parking make this move-in-ready home an exceptional Uptown value!

853 W Lakeside Place Unit #1W, Chicago

$325,000
1 Beds 2 Baths 12731410 MLS CLOSED Status
Welcome to Uptown! This oversized 1-bedroom, 1.1-bath corner condo delivers the space, features, and location that are hard to find at this price point. Set within a gated vintage property with beautiful original architectural details and impressive curb appeal, this move-in-ready home includes gated parking, in-unit laundry, central air, a private covered terrace, extra storage, a walk-in closet, and an en-suite primary bath. The expansive, light-filled living space features multiple exposures, abundant windows, crown molding, and plenty of room for a large sectional plus a separate dining area that comfortably seats six. The open-concept chef's kitchen is designed for both everyday living and entertaining, featuring a Viking range/oven, granite countertops and backsplash, natural wood cabinetry, oversized island with seating, and built-in desk/coffee bar area** with potential for a wine fridge or beverage center. A sliding glass door opens directly to the private covered terrace, offering ample space for outdoor seating and grilling. The king-sized primary bedroom provides excellent flexibility for additional dressers, a desk, or work-from-home space, plus a generous walk-in closet. The en-suite primary bathroom features marble tile, dual vanities, and a whirlpool tub. A separate powder room with black hexagon tile and gold accents provides an additional bath rarely found in a one-bedroom condo. Additional features include a **new refrigerator, updated lighting, central A/C, in-unit washer/dryer, excellent interior storage, separate additional storage, and gated parking included in the price**. The association has completed a reserve study/restoration plan and is actively planning for the long-term maintenance of this distinctive vintage property. Pet-friendly and rentals allowed. Outstanding Uptown location near the **Lawrence Red Line station, Green Mill, Aragon Ballroom, Riviera Theatre, Montrose Beach, Foster Beach, Lake Michigan, and Lake Shore Drive, with convenient access to Target, Aldi, Mariano's, Jewel-Osco, restaurants, nightlife, shopping, and public transportation.

4834 N Kenmore Avenue Unit #GN, Chicago

$599,000
2 Beds 2 Baths 12733138 MLS CONTINGENT Status
Stunning Extra-Wide 2BR/2BA Condo in the Heart of Andersonville. Set in an all brick-and-limestone boutique building, this unit includes a SPACIOUS, OVERSIZED and SEPARATE 1.5 car garage (18.5 ft. W X 19 ft. D X 12.67 H) with abundant storage located inside the building. Move right into this mint-condition, condo offering 1,500 square feet of meticulously maintained open living space. Every detail has been thoughtfully considered - from the high ceilings and oversized windows to the upgraded lighting that fills the combined living/dining area with warmth and light. The chef's kitchen was remodeled in 2017 with painted cabinetry, quartz countertops, an extended island, new backsplash, and new sink, complemented by a newer refrigerator (2020) and stove (2017). Also refreshed in 2017: refinished/stained floors, freshly painted walls, a custom living room built-in, and a stylish fireplace wrap - giving the whole home a cohesive, move-in-ready feel. Retreat to the private primary suite, complete with a spacious walk-in closet and a hotel-caliber marble bath boasting a double vanity, jacuzzi tub, and separate shower. Major systems have been thoughtfully maintained, including a newer condenser, evaporator coil & refrigerant (2017) and water heater (2018), plus a washer/dryer replaced in 2023 - offering real peace of mind for the next owner. The location can't be beat - steps from Clark Street's best dining, shopping, and entertainment, with easy access to the Red Line, Metra, the lake, bike trail, and beach.

5055 N Clark Street Unit #2S, Chicago

$425,000
2 Beds 3 Baths 12569327 MLS CONTINGENT Status
Nestled on a peaceful, tree-lined street in the heart of vibrant Uptown, 4627 N Kenmore Ave Unit 1E is a duplex condo that effortlessly combines modern style, everyday comfort, and unparalleled convenience. From the moment you step inside, you'll feel the warmth of home in the sun-soaked living area, where oversized windows bathe the space in natural light and a cozy gas fireplace invites you to unwind. The open-concept layout flows seamlessly into the chef's kitchen, a true centerpiece equipped with stainless steel appliances, gleaming granite countertops, rich maple cabinetry, and a spacious island perfect for everything from casual breakfasts to hosting friends and family. The main level is designed to impress, featuring beautiful hardwood floors that stretch throughout, a dedicated dining area ideal for dinner parties, and a charming balcony that's perfect for morning coffee or evening relaxation. A convenient half bath adds to the functionality of this level. Upstairs, the thoughtful design continues. The primary suite is a peaceful retreat, boasting generous closet space and a private ensuite bathroom. The large second bedroom offers endless possibilities, use it as a guest room, a home office, or a creative space to suit your needs. High ceilings throughout the home give it an airy feel, while abundant storage and an in-unit washer/dryer enhance the practicality of daily living. One of the standout features. A parking space is included in the price, an invaluable perk in this bustling neighborhood! Additionally, the property allows rentals, offering flexibility for both homeowners and investors. The building itself is equally impressive, with recent updates ensuring peace of mind for years to come. A full roof replacement was completed in 2020, a new AC unit installed in 2021, and a furnace upgrade in 2018, all signs of a well-cared-for property. Location is everything, and this condo delivers. Just minutes from the Red Line, Target, local parks, Montrose Beach, and the lakefront, you'll have endless options for outdoor fun and city exploration. Add to that Uptown's dynamic dining scene and eclectic shops, and you'll never run out of things to do right in your neighborhood. Whether you're looking for a serene retreat or a home that connects you to the best of Chicago living, this is a rare opportunity you won't want to miss. Schedule your showing today and see firsthand why this duplex condo is truly one of a kind!

4627 N Kenmore Avenue Unit #1E, Chicago

$425,000
2 Beds 2 Baths 12710041 MLS CLOSED Status The Sheridan Grande BLDG.
A true urban oasis. Check out this 2bed/2bath, appx 1,400 sqft. 4th floor condo in Uptown! Walk in to a lovely foyer, including large laundry room/closet to the left, featuring upgraded LG washer/dryer units (2024) and extra storage. Continue on into the amply-sized combo kitchen and living room, with separate dining space large enough for an 8-person table. Large sliding doors take you to the attached front balcony. Kitchen features upgraded LG stainless appliances (2022), wrap around granite counter top that finishes at a 4-6 person breakfast bar, with space for an additional island for even more kitchen storage. Second bedroom and bathroom just off the living space will fit a queen-size bed and furniture with ease. Further down takes you to the grand primary suite featuring functional walk-in closet, space for a king-size bed and furniture, and well-appointed en-suite bath with separate soaking tub and shower. Natural light is abundant from the slew of windows. A/C compressor replaced in 2024. Unit comes with assigned exterior parking space and additional storage cage on the first floor. Building features 2 pedestrian elevators, dog run, bike storage stalls in garage ($25.00 annual fee), and expansive rooftop deck available for use year round by all residents. Up to 2 pets allowed per unit, no breed/weight restrictions. This is a lovely place to call home. Schedule your tour today!

4848 N Sheridan Road Unit #407, Chicago

$535,000
3 Beds 3 Baths 12692388 MLS CLOSED Status
Exceptional design, thoughtful upgrades, and an unbeatable Uptown location converge in this beautifully reimagined 3-bedroom, 2.1-bath townhome. Extensively renovated in 2018, this sophisticated residence offers a seamless blend of modern elegance, functional living, and energy-efficient performance within a gated community just moments from Chicago's lakefront, transit, and neighborhood conveniences. Step inside to discover an expansive open-concept floor plan accentuated by soaring ceilings, rich bamboo flooring, recessed lighting, and an abundance of natural light streaming through updated Low-E windows. Designed with both everyday living and effortless entertaining in mind, the stunning chef's kitchen serves as the centerpiece of the home, featuring stainless steel appliances, a substantial quartz island with seating, and seamless connectivity to the spacious living and dining areas. Every detail has been curated for comfort and longevity. High-efficiency HVAC, brand new furnace, central air conditioning, a whole-house humidifier, and a NEST smart home system provide year-round comfort while maximizing energy efficiency. Upstairs, three generously proportioned bedrooms offer exceptional flexibility, including a spacious primary retreat complete with a large closet and an updated ensuite bath featuring a double vanity and timeless finishes. The partially finished lower level expands the home's versatility, offering the perfect space for a home office, fitness studio, media room, recreation area, or additional storage. A full-size side-by-side washer and dryer further enhance everyday convenience. Outdoor living is equally impressive. A newer composite deck, privacy fencing, and updated front concrete create a rare urban sanctuary ideal for morning coffee, evening gatherings, or simply unwinding outdoors. The home also includes an assigned exterior parking space, with additional zoned street parking available for residents and guests. Professionally managed and exceptionally maintained, the association provides peace of mind with assessments that include exterior maintenance, common insurance, snow removal, scavenger (trash) service, and parking. Water is not included in association fees. With no planned special projects currently pending, homeowners can enjoy confidence in both ownership and future value. Positioned in one of Chicago's most vibrant and connected neighborhoods, residents enjoy immediate access to the CTA Red Line, Metra, multiple bus routes, Montrose Beach, Montrose Dog Beach, Target, Aldi, Jewel-Osco, Walgreens, CVS, neighborhood parks, and an ever-growing collection of restaurants, cafes, and entertainment destinations. Offering the space of a single-family home, the convenience of townhome living, and a location that places the best of Chicago at your doorstep, this exceptional residence presents a rare opportunity to secure a truly move-in-ready home in one of the city's most sought-after neighborhoods.

4647 N Kenmore Avenue Unit #B, Chicago

$610,000
3 Beds 2 Baths 12664956 MLS CLOSED Status
MULTIPLE OFFERS RECEIVED! Highest and Best due Sunday 5/7 at 4:30 PM. Gorgeous and Remodeled 3 Bed, 2 Bath Uptown Penthouse with Luxurious Upgrades and Improvements! Be prepared to fall in love with this fabulous townhouse on a tree lined street that offers the perfect blend of space, elegance, and comfort! Absolutely stunning light and bright LV/DR combination features 13' vaulted ceilings, huge windows, recessed lighting, gas fireplace, and newer light fixtures. The stunning open-concept layout is complimented by hardwood flooring, crown molding and white doors and trim throughout. Spectacular designer inspired gourmet kitchen boasts 47" soft close cabinets, granite countertops, All S.S. appliances, large pantry, and an oversized center island w/large vented hood over five burner range. Additional kitchen entertaining area includes custom cabinets w/granite countertops, wine cooler and tons of storage. Glamorous Main bedroom includes newer lighting, and a huge walk-in closet with custom closet system. Remodeled in 2024, Gorgeous SPA-like main ensuite features double vanity w/quartz countertops, white custom soaking tub,(2024) deluxe steam shower,(2024) and stunning white backsplash and porcelain flooring (2024). Two additional large bedrooms include generous closets, and newer lighting. Fabulous deck offers picturesque views and the perfect place for entertaining or relaxing. Additional amenities include In Unit Washer/Dryer(2022), HVAC (2021), Water Heater (2021), 1 car garage parking space, additional storage locker, Lutron dimmers, smart locks, surround sound, and Nest thermostat. Located close to restaurants, entertainment, Aragon Theatre, Red-line, parks and Lakefront. Make it Yours today!

4831 N Winthrop Avenue Unit #3S, Chicago

$475,000
2 Beds 2 Baths 12589862 MLS CLOSED Status
Situated on a quiet, one way street in the heart of Uptown, this beautifully updated 2 bedroom, 2 bathroom condo offers an ideal combination of space, comfort, and location just steps from everything the neighborhood has to offer. Recently painted and featuring hardwood floors throughout, the home provides a clean, modern feel with a functional layout designed for both everyday living and entertaining. The oversized kitchen offers excellent storage and prep space, complete with granite countertops, stainless steel appliances, and solid wood cabinetry. Seller had an island made to fit perfectly in the kitchen space that is included in the sale. The open layout allows for a seamless flow into the main living area, creating a comfortable space for relaxing or hosting guests. Both bedrooms are generously sized with ample closet space and the primary bedroom fits a king sized bed. The primary bathroom was just redone and includes an ensuite double vanity bathroom with heated floors. The second full bathroom is conveniently located for guests or additional household members. One of the standout features of this home is the rare private deck AND front patio, offering a large area perfect for enjoying fresh air, grilling, or creating an outdoor seating area. IN UNIT washer/dryer makes doing laundry a breeze. Additional highlights include excellent natural light and a location that provides easy access to public transportation, including the Red Line, making commuting throughout the city simple. Just a few blocks from Lake Shore Drive and Lake Michigan, the home is also right around the corner from Target, Aldi, The Riviera Theater, Nabala Cafe, Carino, Gigios Pizzeria, Stan's Donuts, and so much more. Garage parking is available for lease a couple blocks away for approximately $200 per month via SpotHero. With its spacious layout, outdoor living areas, and prime Uptown location close to the lake and transit, this condo is a fantastic opportunity to enjoy city living with everyday convenience.

4648 N Winthrop Avenue Unit #2A, Chicago

$1,250,000
4 Beds 3 Baths 12614166 MLS CLOSED Status
**** MULTIPLE OFFERS HAVE BEEN RECEIVED, BEST AND FINAL DUE BY 8P SUNDAY**** Step into perfection in this extraordinary Andersonville duplex, where every detail has been thoughtfully designed and beautifully executed. This all-brick custom residence sits on an oversized 33-foot lot, allowing for an impressive 24-foot-wide interior rarely found in the city. The gracious main level offers exceptional flow with formal living and dining spaces, plus a welcoming family room, creating the ideal layout for both elegant entertaining and effortless daily living. At the heart of the home, the chef's kitchen is a true showpiece, featuring a 10+ foot island, butler's pantry, and refined finishes curated for those who love to cook, gather, and host. Multiple outdoor spaces elevate the experience even further, including front and rear terraces with direct access to the private garage roof deck, complete with gas & water for seamless indoor-outdoor living all season long. Custom Sonos system with dynamic in ceiling speakers in the home. A dramatic, well-positioned staircase leads to the private bedroom level below, where 9+ foot ceilings and radiant heated floors create warmth and comfort throughout. The stunning primary suite is a true retreat, offering a 14x7 walk-in closet, meditation area, spa bath with double vanity, and oversized steam shower. Three additional bedrooms, one currently configured as an office, and another full bath provide lifestyle flexibility. With its scale, finish level, and lifestyle appeal, this home gives upper-bracket custom single-family living a serious run for its money. Professionally landscaped front and rear yards are maintained seasonally, while the self-managed association keeps overhead low and maintenance a priority. One garage space included. All just moments from Andersonville favorites, Rogers Park Montessori, the Waldorf School, the Red Line, and the lake.

1448 W Carmen Avenue Unit #1, Chicago

$810,000
3 Beds 3 Baths 12607279 MLS CLOSED Status
Spectacular extra-wide new construction in the heart of Andersonville. Set on a 35-foot-wide lot, this spectacular north-facing duplex-down offers a serene living experience on one of Andersonville's quietest streets while still being less than a three-minute walk from all of the shops, restaurants and vibrant energy of Clark & Foster. With your own private side entrance, enter this home to a dramatic, double-high atrium providing stair access to both the upper and lower levels. As you ascend to the main living space the width of this unit will blow your mind. Finally, a condo with a generously sized kitchen, a generously sized living room and a true, defined dining room! Not to mention a south-facing deck finished with 24" x 24" porcelain tile overlooking charming, tree-lined Winona. Features of this home include: 4-inch American white Oak hardwood floors, 8-foot solid core two-panel inset doors and 9-foot ceilings and custom closets throughout. Kitchens include a full Thermador appliance package, 1.25-inch quartz counters with waterfall-edge island, custom cabinets with soft-close hinges and drawers. A gas, ventless fireplace with beautiful surround is the focal point of the family room which also has a powder room and large coat closet. The lower level has 3 nicely sized bedrooms, custom closets throughout, a hall bath with hexagonal marble stone flooring, marble tub and shower surround and floating vanity with 1.25-inch quartz countertop. The primary bedroom captures tremendous southern light and primary bath features a floating vanity, double sinks, 12" x 24" stone floors, enormous walk-in shower with rain shower, hand-held, soap niche and bench. The unit also comes with a garage-top deck finished with 24" x 24" porcelain tiles. Garage parking included. Available for immediate delivery.

1304 W Winona Street Unit #1N, Chicago

$825,000
3 Beds 2 Baths 12601776 MLS CLOSED Status
Spectacular extra-wide new construction in the heart of Andersonville. Set on a 35-foot-wide lot, this spectacular south-facing simplex offers a serene living experience on one of Andersonville's quietest streets while still being less than a three-minute walk from all of the shops, restaurants and vibrant energy of Clark & Foster. Not your cookie-cutter condo, as you enter this home you will be blown away by the width and the layout! Finally a condo with a generously sized kitchen, a generously sized living space and a true, defined dining area. Not to mention a south-facing deck finished with 24" x 24" porcelain tile overlooking charming, tree-lined Winona. Features of this home include: 4-inch American white Oak hardwood floors, 8-foot solid core two-panel inset doors, 9-foot ceilings and custom closets throughout. Kitchens include a full Thermador appliance package, 1.25-inch quartz counters with waterfall-edge island, custom cabinets with soft-close hinges and drawers. A gas, ventless fireplace with beautiful surround is the focal point of the family room. As you continue through the home, you'll find 3 nicely sized bedrooms, a hall bath with hexagonal marble stone flooring, marble tub and shower surround and floating vanity with 1.25-inch quartz countertop. The primary bedroom boasts a large walk-in closet, and primary bath features a floating vanity, double sinks, 12" x 24" stone floors, and an enormous walk-in shower with rain shower, hand-held, soap niche and bench. Not to be overlooked is a large, walk-in laundry room with stackable washer/dryer and plenty of room for storage. Garage parking included. Available for immediate delivery. Photos coming 2/19.

1304 W Winona Street Unit #2, Chicago

$744,900
4 Beds 3 Baths 12593507 MLS CLOSED Status
Welcome to this beautifully updated 4-bedroom, 3-bath duplex-down in the heart of Uptown, offering the space and comfort of a single-family home with approximately 2,500 sq. ft. of living space. Step inside to soaring ceilings, crown molding, and abundant natural light throughout the main level. Newly refinished hardwood floors lead to a spacious living and dining area centered around one of two cozy fireplaces, creating a warm and inviting atmosphere. The updated kitchen features granite countertops, stainless steel appliances, and a large island-perfect for everyday living or entertaining. The king-size primary suite offers a true retreat with three custom closets and a spa-inspired ensuite bath featuring marble finishes, a jetted soaking tub, and a steam-shower cabin. The expansive lower level provides exceptional living space with floor-to-ceiling windows, a large family room with a second fireplace, and a bar center ideal for gatherings. A private front patio extends the living space outdoors. Additional highlights include: large private deck with gas line for grilling, garage parking plus additional exterior parking space, ample storage with 10+ closets, dedicated exterior storage room (approx. 4' x 14'), large laundry room, two mailboxes - ideal for home office or business use. This highly desirable duplex-down layout offers generous space, beautiful finishes, and an unbeatable location near the lake and transit. Enjoy living steps from Uptown's vibrant dining and entertainment scene, including performances at the iconic Aragon Ballroom and Riviera Theatre, and live jazz at the legendary Green Mill Lounge. Everyday conveniences like Target, JewelOsco, and ALDI are just blocks away.

5021 N Kenmore Avenue Unit #1N, Chicago

$840,000
3 Beds 3 Baths 12569592 MLS CLOSED Status
Spectacular extra-wide new construction in the heart of Andersonville. Set on a 35-foot-wide lot, this spectacular south-facing duplex-down offers a serene living experience on one of Andersonville's quietest streets while still being less than a three-minute walk from all of the shops, restaurants and vibrant energy of Clark & Foster. With your own private side entrance, enter this home to a dramatic, double-high atrium providing stair access to both the upper and lower levels. As you ascend to the main living space the width of this unit will blow your mind. Finally, a condo with a generously sized kitchen, a generously sized living room and a true, defined dining room! Not to mention a south-facing deck finished with 24" x 24" porcelain tile overlooking charming, tree-lined Winona. Features of this home include: 4-inch American white Oak hardwood floors, 8-foot solid core two-panel inset doors and 9-foot ceilings and custom closets throughout. Kitchens include a full Thermador appliance package, 1.25-inch quartz counters with waterfall-edge island, custom cabinets with soft-close hinges and drawers. A gas, ventless fireplace with beautiful surround is the focal point of the family room which also has a powder room and large coat closet. The lower level has 3 nicely sized bedrooms, custom closets throughout, a hall bath with hexagonal marble stone flooring, marble tub and shower surround and floating vanity with 1.25-inch quartz countertop. The primary bedroom captures tremendous southern light and primary bath features a floating vanity, double sinks, 12" x 24" stone floors, enormous walk-in shower with rain shower, hand-held, soap niche and bench. The unit also comes with a garage-top deck finished with 24" x 24" porcelain tiles. Garage parking included. Available for immediate delivery. Photos coming 2/19.

1304 W Winona Street Unit #1S, Chicago

$755,000
3 Beds 2 Baths 12566767 MLS CLOSED Status
Elevate your lifestyle in this stunning, top-floor unit within a meticulously crafted, full-masonry building. Offering the perfect blend of modern design and timeless quality, every inch of this property is thoughtfully designed with superior attention to detail. Step into a light-filled oasis, thanks to oversized European multi-position windows that bathe every room in natural light and invite refreshing breezes from all exposures. Inside, you'll find luxurious European-inspired finishes: wide 5" plank engineered hardwood floors, sleek recessed LED lighting, soaring 9+ foot ceilings, and solid 7' core doors that exude sophistication. The gourmet kitchen is a chef's dream, boasting custom European-style flat-panel cabinetry, an oversized island, quartz countertops, a Bosch appliance package, under-cabinet lighting, and even a dry beverage bar for entertaining. The spa-like bathrooms feature porcelain tile, polished chrome fixtures, and quartz countertops, while the primary suite adds a touch of indulgence with its NuHeat heated floors and programmable thermostat. Outdoor living is just as spectacular, with a private front balcony and an exclusive rooftop terrace featuring composite decking, lighting, power, and gas connections-perfect for hosting or unwinding under the stars. The property also includes a fully fenced perimeter, concrete sidewalks, a rear driveway, and parking to ensure convenience and security. Discover elevated living where style, comfort, and design come together flawlessly. Garage Parking included. Conveniently located near amazing restaurants and coffee shops, close to interstate. Beautiful location!

4937 N Winthrop Avenue Unit #3N, Chicago

$770,000
3 Beds 3 Baths 12562722 MLS CLOSED Status
Exquisite 3-bedroom, 3-bath duplex-down residence in the heart of Uptown with a rare private two-car garage. This expansive unit lives like a single-family home and showcases inlaid hardwood floors, crown molding throughout, two fireplaces, and soaring ceilings on both levels. Exceptional natural light fills the space with desirable north, west, and east exposures. The main level is designed for everyday living and effortless entertaining, with generous living and dining areas that flow seamlessly into the thoughtfully designed chef's kitchen which features rich cherry cabinetry, granite countertops, brand new premium stainless-steel appliances, and an expansive island. The serene, main level primary suite easily accommodates a king-size bed and offers a newly renovated spa-inspired ensuite bath with luxurious marble finishes, a whirlpool soaking tub, and a custom new separate glass-enclosed shower. A second bedroom, newly updated full bath, and private deck complete the main level. The lower level provides an ideal extension of the home with a spacious family room with wet bar and wine cooler, large third bedroom, recently updated full bath, laundry room, discreet under-stairs storage, private storage room, and outdoor access. Set on a quiet, tree-lined stretch of Winthrop Avenue, this home is just steps from the brand new Argyle Red Line Station, providing modern, accessible transit and quick access downtown and across the city. Enjoy easy walks to Foster Beach, Margate Park, and the lakefront trail as well as nearby dining, shopping, and entertainment in Uptown and Andersonville.

4933 N Winthrop Avenue Unit #1N, Chicago

$1,710,000
6 Beds 5 Baths 12521948 MLS CLOSED Status
***MULTIPLE OFFERS RECEIVED. HIGHEST AND BEST CALLED FOR BY MONDAY, JANUARY 19TH @ 12 NOON. NO ESCALATION CLAUSES OR LOVE LETTERS.*** Tucked away on a quiet tree-lined street is this classic Chicago Greystone set on an exceptionally rare 40' x 150' lot. Renovated in 2018 and thoughtfully enhanced in 2022, the home blends turn-of-the-century character with modern comfort. Between the wide lot offering a generous setback from neighbors on both sides, and large windows in every room, the entire home is filled with an abundance of natural light, while hardwood floors and high ceilings add to the home's vibrance and charm. A professionally landscaped front yard leads into a gracious foyer and a flowing main level with a formal living room anchored by a gas fireplace, a gracious formal dining area, and a high-end kitchen featuring stainless steel appliances (Wolf range, Sub-Zero refrigerator), quartz countertops, an island with bar seating, and a nook for an eat-in area. Beyond the kitchen is an oversized family room opening to a steel back deck overlooking perennial prairie gardens and raised vegetable beds. A powder room, built-in pantry storage, and full laundry room complete this level. Atop the sweeping staircase, the second floor offers four spacious bedrooms and three full baths. The sun-drenched south-facing primary suite features a gorgeous window bay, walk-in closet, and spa-inspired bath with dual vanities, soaking tub, full height pull-out storage cabinet, and a walk-in shower. The three other bedrooms on this level enjoy abundant natural light, optimized storage, and hardwood floors, plus a second laundry hookup conveniently located in a hallway closet. The fully finished lower level was repurposed and remodeled in 2022, and is accessed via its own private entrance. This space functions as a flexible 2-bedroom, 1-bath suite with a private entrance, full kitchen, laundry, heated bathroom floors, and bright, comfortable living spaces-ideal for guests, multi-generational living, work-from-home/home business space, additional household support, or supplementary income. The staircase down to the basement from the main level has potential to be re-installed by the new owner--ask agent for details! With no alley behind the property, the backyard lives like a private urban sanctuary-an expansive, sunny retreat to host unforgettable evenings with family and friends. Own this home with peace of mind, knowing the current owners have poured over $450,000 into enhancing the home's efficiency, longevity, and eco-friendliness--an Improvement List can be provided upon request! Andersonville was rated as "America's Coolest Neighborhood" in 2021 by TimeOut, and this block of Carmen encapsulates the best of Uptown/Andersonville living--small town charm with big city conveniences, and a lively block club (Winona Foster Carmen Winnemac, "WFCW"). Nestled between the Broadway and Clark Street corridors, this area offers effortless walkability and access to beloved grocery stores (Jewel-Osco and Marianos are closest), gyms, coffee shops, boutique galleries, dining, nightlife and entertainment. Just around the corner is Asia on Argyle (home to the summer Argyle Night Market and incredible Asian cuisine options), historic Green Mill Tavern Jazz Club, Aragon Ballroom, and the Riviera Theatre. Equidistant to the Argyle and Berwyn CTA Red Line Stations, as well as CTA buses on Broadway, Clark Street and Foster Avenue. For those who enjoy spending summers at Lake Michigan, Foster Beach, Saddle & Cycle Club, and the Lakefront Trail are just 5 blocks away! Carmen Park playground is a few doors down, and many school options abound including McCutcheon, Chicago Montessori, Rogers Park Montessori, Sacred Heart, and Waldorf School.

1252 W Carmen 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

$925,000
3 Beds 2 Baths 12456028 MLS CLOSED Status
Stunning Andersonville Penthouse with Private Rooftop Oasis. Live above it all in this incredible 3-bedroom, 2-bath Andersonville Penthouse, where luxury, design, and location come together seamlessly. Set atop a reimagined historic greystone, this one-of-a-kind home features a showstopping 1,200 SF private rooftop deck-custom-built for entertaining and relaxation. Just steps from Andersonville's vibrant shops, dining, and nightlife, this third-floor residence offers three private outdoor spaces: a spacious front balcony, a rear terrace, and the ultimate rooftop retreat. Your rooftop paradise is outfitted with a hot tub, pergola, two-sided gas fireplace, radiant heater, outdoor kitchen with built-in grill and beer taps, refrigerator, TV mount, and lush landscaped planters-all accessible via interior stairs for seamless indoor-outdoor living. Inside, the home boasts an open-concept island kitchen with rich cabinetry, quartz counters, custom backsplash, and top-tier appliances including Sub-Zero fridge, Blue Star range, Bosch dishwasher, and a beverage center. Thoughtful touches like oak floors, crown molding, integrated speakers. The king-sized primary suite is a spa-inspired sanctuary with a stone bath, oversized steam shower with body sprays, double vanity, and radiant heat flooring. Two additional spacious bedrooms and a beautifully appointed second bath with a jetted tub complete the layout. Additional perks include in-unit laundry, garage parking plus tandem exterior space, and extra storage. Truly a rare find in one of Chicago's most sought-after neighborhoods.

1457 W Carmen Avenue Unit #3W, Chicago

$553,000
3 Beds 2 Baths 12450378 MLS CLOSED Status
Welcome to 5133 N Kenmore Ave Unit 2N-an updated vintage condo that blends character with modern comfort just steps from the lakefront and vibrant Andersonville. The spacious, light-filled floor plan offers an open kitchen with granite countertops, stainless appliances, and a breakfast-bar island with direct access to the back deck-perfect for dining outside. A generous dining area flows into the living room with a cozy gas fireplace. The expansive primary suite features a walk-in closet, spa-like bath with Jacuzzi tub and separate shower, a charming office nook, and access to the front porch. A second bedroom sits off the hallway, while the third flex bedroom works well as a guest room, den, office or TV room with an included built-in murphy bed. In 2025, the home underwent a thoughtful renovation: the entire condo was painted, hardwood floors were refinished, kitchen cabinets were painted white, and the primary bathroom received a new vanity, new vanity mirrors, and new bathroom fans. The ceiling lighting was also fully updated throughout the home. Major systems and appliances were refreshed as well, including a new furnace and air conditioner (2025), oven, dryer and garbage disposal (2025), and a new washing machine (2023). Additional highlights include in-unit laundry, central air, hardwood floors, front and back outdoor spaces, excellent closet storage and a storage locker in the building's lower level. Mariano's is down the block; beaches, shops, and the CTA Red Line, express buses, and Lake Shore Drive are all nearby. Rental parking options are available. Schedule a showing today!

5133 N Kenmore Avenue Unit #2N, Chicago

$535,000
2 Beds 2 Baths 12461855 MLS CLOSED Status
Custom-designed and truly one of a kind, this expansive 2 bed, 2 bath loft in the sought-after Gunnison Street Lofts was completely built out for the owner with no detail overlooked. Originally a 3-bedroom layout, it was reconfigured into a spacious 2-bedroom to maximize living and entertaining space while showcasing custom millwork and luxury finishes throughout. Soaring 17-foot ceilings and floor-to-ceiling windows flood the space with natural light. Bamboo hardwood flooring runs throughout the open-concept living and dining area, which is an entertainer's dream with integrated A/V, custom lighting, and direct access to a private outdoor deck. The chef's kitchen stands out with a rare dual-island layout, honed granite countertops, Sub-Zero refrigerator, Bosch and Dacor appliances, back-painted glass backsplash, custom cabinetry, and a dry bar with wine fridge and glass display. The king-sized primary suite features a spa-caliber bath with heated slate floors, a walk-in steam shower with rain head and bench, dual glass vessel vanities, and custom tilework. The second bedroom is designed with floor-to-ceiling custom millwork, built-in desk, and a queen-sized Murphy bed, perfect for flexible use as an office or guest space. Additional highlights include 14-foot motorized window treatments, surround sound speakers, oversized solid core doors, built-ins, recessed lighting, professionally organized closets, and a dedicated laundry room with storage and newer in-unit washer and dryer. One heated garage parking space and private storage are included. Set in an intimate 22-unit elevator building with a classic brick and terra cotta facade, just steps from the new Lawrence Red Line stop, the lakefront, parks, restaurants, entertainment, and everything Uptown has to offer!

1215 W Gunnison Street Unit #205, Chicago

$399,000
2 Beds 2 Baths 12458305 MLS CLOSED Status
Enjoy sweeping skyline and lake views from this bright, top-floor, 2-bed, 2-bath corner condo at 1000 W Leland. The spacious living and dining area features floor-to-ceiling windows, hardwood floors, and a striking custom marble-surround fireplace that serves as the room's focal point. Just off the living room, step onto the large private balcony for unobstructed northern city & lake views, perfect for relaxing or entertaining. The open layout flows into the updated kitchen with new white quartz countertops, black hardware, stainless steel appliances, an KitchenAid electric cooktop, and an island with seating. The primary suite includes floor-to-ceiling windows, a walk-in closet, and a stylish ensuite bath with a marble-accented walk-in shower and modern vanity. The bright second bedroom features large windows and can serve as a guest room, office, or workout space. A full guest bath, located on the opposite side of the unit for privacy, includes a tub/shower combo and updated finishes. Both baths and the primary bedroom have been freshly painted. Additional highlights include in-unit laundry with a stackable Bosch washer/dryer, carpet in the bedrooms, and multiple storage options. This boutique, pet-friendly building offers a fitness room, bike storage, package lockers, and a rooftop deck with panoramic views. One secured interior garage parking is included. Ideally located near shops, Target, Mariano's, Aldi, restaurants, nightlife, and just blocks from Montrose Beach, lakefront trails, and Uptown's iconic entertainment venues (with more on their way). Convenient access to the newly re-opened CTA Red Line stations and express buses makes commuting easy!

1000 W Leland Avenue Unit #12G, Chicago

$635,000
3 Beds 2 Baths 12371380 MLS CLOSED Status
Welcome to your dream home-modern luxury meets timeless design in this impeccably crafted/designed 3 bed, 2 bath residence. Built in 2024 by the renowned Vari Architects Group, this high second-floor unit offers a refined living experience with elegant finishes, thoughtfully designed spaces, and sophisticated style from the moment you step inside. Enjoy a spacious layout with a 17' x 7' front terrace that offers composite decking, gas and electric hookups, and built-in lighting plus an additional private rooftop deck space above the garage-perfect for relaxing or entertaining. This gated and full-masonry building (no split-face block) stands out with clean, contemporary architecture . Inside, you'll find wide 5" plank engineered hardwood floors, 7' solid-core doors, recessed LED lighting and expansive European-style windows flood the home with natural light. The chef's kitchen is a true showpiece, featuring custom flat-panel European cabinetry, an oversized quartz island, high end SS appliances, under-cabinet lighting, an integrated small appliance garage complete with internal electrical outlets, a custom pantry, and a stylish dry bar with built-in shelving and a beverage fridge. Both bathrooms are elegantly appointed with quartz countertops, porcelain tile, and polished chrome fixtures. The luxurious primary bath also includes a NuHeat radiant heated floor system with programmable thermostat. Oversized garage parking spot with bike rack included in price! Located on a peaceful tree-lined street just one block from the El station, this home is steps from Andersonville's beloved shops, bakeries, and restaurants, and just a short walk to the lakefront, dog beach, and Puptown Dog Park for your furry friends. Notable upgrades include: * A custom-built Murphy bed with integrated desk in the second bedroom by Closet Factory ($15,000 cost/value with a lifetime warranty), creating a versatile guest room/home office combo. * High-end, custom light filtering window treatments from Ashland Blinds (over $5000 cost/value). Don't miss this rare opportunity to own a modern, thoughtfully upgraded home in one of Chicago's most vibrant neighborhoods.

4906 N Kenmore Avenue Unit #2S, Chicago

$885,000
3 Beds 3 Baths 12300056 MLS CLOSED Status
Welcome home to The Renslow. Completed in 2021, this boutique, 14 unit elevator building brings the utmost in luxury to Andersonville, one of the most sought after neighborhoods in all of Chicago and voted coolest neighborhood in America! Immediately when you walk into the large foyer you'll notice the stunning white oak floors, 9' ceilings with crown molding, and 8' solid-core doors. To your left opens into the expansive living area with a ventless gas fireplace encased in Venetian plaster. Natural light floods this corner unit from the East and North. The dining room features custom cabinetry with glass doors, while the built-in bench adds extra seating and additional storage. Large patio doors take you to your first of two outdoor spaces. This balcony easily fits a grill and furniture allowing you to dine al fresco or enjoy a morning cup of coffee as the sun rises. With a 36" Wolf gas cooktop and hood, KitchenAid double ovens, a JennAir refrigerator, and a separate beverage refrigerator, the kitchen will exceed your expectations. Ample two-tone cabinets, open shelving, plus a massive central island with a waterfall edge provide plenty of storage, workspace, and room for several barstools. Take advantage of the surround sound to play your favorite music while you dine. Down the hall you'll find in-unit laundry, more storage, 2 guest bedrooms, a powder room, and a full bathroom. At the end of the hall leads you to the owner's suite. The large ensuite has heated basketweave tile floors, a steam shower with rainfall head, hand and body sprayers, and a dual vanity. The bedroom easily allows for a king-size bed and the custom walk-in-closet provides plenty of storage. As incredible as this home is, it gets even better. The 400 sf rooftop terrace is the perfect setting to entertain on warm summer nights. Fully equipped with Trex decking, a gas line, water, electric and WiFi, this space is ready for the next homeowner to enjoy the stunning views of the city. Completing this property is an assigned heated garage space, bike storage, and a massive 10'x8' climate controlled storage room. Walk to the locally owned shops, dine on the patio at some of your favorite restaurants, or grab a cup of coffee from one of the charming cafes that make Andersonville an incredible place to call home. Schedule a showing today!

5015 N Clark Street Unit #305, Chicago

$905,000
4 Beds 2 Baths 12335222 MLS CLOSED Status
***Multiple Offers Received, Highest & Best due Monday, April 28th at 9:30am*** This light-filled, beautifully updated Victorian welcomes you with a charming front porch and timeless curb appeal. Inside, you'll find quality craftsmanship, architectural detail, custom millwork, and multiple outdoor living spaces - all just blocks from the vibrant shops and restaurants of Uptown and Andersonville. The airy living room features high ceilings, crown molding, and original pocket doors. Hardwood floors flow into the dining area with built-ins, a cozy office/den with custom bookshelves, a half bath, and the fully updated kitchen. Thoughtfully designed with modern luxury and classic charm, the kitchen offers quartz countertops, a farm sink, tile backsplash, stainless appliances, floating shelves, a center island with seating, a pantry and floor to ceiling storage. It opens to a covered deck with tongue-and-groove ceiling, recessed lighting, and space for outdoor dining. Step down to a brick paver patio surrounded by landscaping and situated under a mature maple tree- perfect for relaxing or entertaining. Upstairs, you'll find four bedrooms (one is a perfect size for an office), including a spacious primary suite with a walk-in closet. A second bedroom also features a walk-in, and the fully renovated bath includes a deep soaking tub, separate rain shower, and sleek modern vanity. The lower level provides a large recreation room, expansive laundry area, and ample storage. Additional features include an unfinished attic with pull down stairs/ladder, a WiFi thermostat, and a 2-car detached garage. Enjoy close proximity to the lakefront, beaches, running and biking trails, Montrose Dog Beach, and Foster Turf Fields. Convenient access to the Red Line, Metra, Lake Shore Drive, and major expressways makes commuting easy. You're also near beloved music venues like the Riviera, Aragon Ballroom, and Green Mill, plus a wide variety of local favorites like Hop Leaf, La Colombe, m.henry, Sun Wah BBQ, and more. A must-see!

1255 W Argyle Street, Chicago

$1,570,000
4 Beds 3 Baths 12310787 MLS CLOSED Status
Spectacular home in every way situated on a 30 ft wide lot steps to Clark Street in Andersonville. This perfectly designed, executed and updated home exudes modern style and every convenience while maintaining its classic Chicago character. Enter the open living and dining room after stepping off the beautiful, heated tile entry to spacious living with highlights that include a custom limestone fireplace surround, outstanding imported chandelier, classic Chicago details in staircase and crown molding. Light pours in from the updated windows selected to recreate the original 1908 design on the front of the home. Walk to the back of the home to see the showstopper kitchen, eating/entertaining area and wet bar. Silestone counters, an abundance of cabinets, large island, high end appliances, gorgeous Ann Sacks wall tile and the most beautiful arched window built custom for maximum light and to showcase the beautifully landscaped backyard. Enjoy great space for large table or additional living space. The exquisite bar is an entertainer's dream with beautiful cabinets, lighting and backsplash and convenient pantry. Just outside the door is a large deck with built in bench and leads to superbly landscaped yard with bluestone seating area and walkway lined with beautiful plants, grasses and unique evergreens, making a true oasis from the nearby bustle of the dynamic neighborhood. Back inside, there's a full bedroom and beautiful full bath completing the main floor of the home. Upstairs is a comfortable family room, perfect for binge watching, great home office or 4th bedroom, another guest room and full bath, and an enviable primary suite. This oversized bedroom provides a peaceful place to begin and end the day after enjoying the stunning bath with huge shower with overhead rain shower, heated floors, custom vanity with quartzite, and beautiful lighted mirrors offering abundant hidden storage. Capping off this upper level is a convenient second floor laundry room with farmhouse sink, front loading machines on pedestals, great storage and an awesome vintage swing door. The full unfinished basement provides unlimited storage and the potential for additional living space. This magnificent home is truly move-in ready and not to be missed.

1443 W Winona Street, Chicago

$660,000
3 Beds 2 Baths 12300212 MLS CLOSED Status
Sunny and spacious in a great location! Welcome home to this stunning condo in a classic, all brick Chicago flat which was completely renovated in 2016, and boasts all the modern updates today's buyer desires. The open floor plan provides a warm and inviting living space centered around gas fireplace with modern stone surround. There is a true dining area with plenty of space for a large table. The sunroom makes a perfect place to work, read or even nap and fills the living space with loads natural light. The living space flows seamlessly into the kitchen which is anchored by an island with counter seating and features a Viking range, quartz countertops , a pantry cabinet and new Samsung glass front refrigerator and dishwasher. The seller has thoughtfully converted a small utility closet to additional storage space featuring pull out cabinets and a beverage fridge. The primary suite is a spacious and stylish retreat featuring craftsman style wood wainscoting, two closets and plenty of light from the bay window. The primary bath is all you could ask for with a walk in shower, large soaking tub, double vanity and separate wc. This home has two more spacious bedrooms and in unit laundry. Garage parking space and extra storage closet included. Outside you'll find a private deck, and residents enjoy the common yard with a fire pit and dog run. Located on a quiet, tree lined street with easy access to transit and short walk to all the shopping, dining and entertainment of Clark Street including Bar Roma, The Magic Lounge and Tala House.

1330 W Winnemac Avenue Unit #2, Chicago

$500,000
2 Beds 2 Baths 12287960 MLS CLOSED Status
Welcome to this fantastic 1,400 SF Andersonville condo, perfectly located just steps from the vibrant shops, pubs, restaurants, and gyms on Clark Street. This beautifully updated home features an open-concept kitchen and living area that serves as the heart of the space. The newly renovated kitchen, completed in 2020, boasts white quartz countertops, a modern backsplash, cherry cabinets, a spacious island, and high-end stainless steel appliances, including a new fridge and sink. Smart lighting throughout the condo adds convenience and modern flair. Flooded with natural light, the living area offers a warm and inviting ambiance, while the expansive primary bedroom provides direct access to a private, quiet deck-the perfect retreat for morning coffee or evening relaxation. The primary bathroom is well-appointed with double sinks and a separate shower. Hardwood floors run throughout the home, adding to its elegant appeal. Outdoor living is enhanced by the private deck, a fenced-in landing area, and a lovely garden space to the side of the building. Additional features include in-unit washer and dryer, a new water heater (2021), and a new A/C system for year-round comfort. Parking is a breeze with easy street parking options. You have the opportunity to rent at a nearby garage for $165 a month. With convenient access to the Red Line and Clark/Broadway bus routes, this home combines modern updates, thoughtful design, and an unbeatable walkable location in the heart of Andersonville. Don't miss this incredible opportunity to make it yours!

1463 W Winnemac Avenue Unit #2E, Chicago

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Uptown, Chicago IL · Curated MLS Search

Homes with Double Island in Uptown, Chicago IL

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

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