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$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
$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
$525,000
3 Beds ⋅ 2 Baths ⋅ 12736381 MLS ⋅ CONTINGENT Status
Welcome to this rare, sun-drenched 3-bedroom, 2-bathroom duplex penthouse in the heart of vibrant Uptown! Spanning 1,700 sq. ft. across two levels, this urban retreat offers a unique and versatile layout complete with a bonus loft space for living large. The main level features an expansive, open-concept living and dining area centered around a custom fireplace, flowing into a chef's kitchen with granite countertops and high-end stainless steel appliances. Step outside to three private outdoor decks, including a top-tier rooftop space with sweeping city views that's perfect for entertaining. The primary suite serves as a true sanctuary, featuring a walk-in closet and a spa-like bath with a Jacuzzi tub and separate shower. Unbeatable location with a Walk Score of 95: just 1.5 blocks to the CTA Red Line, moments to DuSable Lake Shore Drive, Lake Michigan beaches, and world-class dining and entertainment.

4648 N Winthrop Avenue Unit #3S, 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
$725,000
2 Beds ⋅ 2 Baths ⋅ 12716650 MLS ⋅ CONTINGENT Status ⋅ Andersonville BLDG.
Modern, light-filled 2-bedroom penthouse in a beautiful historic Chicago greystone, tucked onto a quiet residential street in one of the city's most vibrant neighborhoods. Fully updated in 2021, this home blends contemporary style and convenience with the architectural character of the original building. The south-facing main living space is bathed in incredible natural light and features hardwood floors, 9 foot ceilings, and motorized blinds for effortless comfort. At the heart of the home, a large open kitchen offers abundant storage, generous counter space, and a functional layout perfect for everyday living and entertaining. The spacious, updated primary suite includes a well-appointed bath with a large shower featuring both rainfall and handheld options. The unit has been professionally finished throughout in designer Farrow & Ball paint. Every room feels curated and move-in ready. Enjoy central air and heat, a full size washer and dryer, and a parking spot with a Level 2 EV charger. The unit has ample storage to round out the thoughtful details. You will find custom solid-wood closet organizers throughout, including both bedrooms, pantry, and hallway closets. Enjoy two private outdoor spaces: a convenient side deck off the kitchen, ideal for grilling or enjoying your morning coffee, and a roof deck (30x14) with sweeping views and room to gather. The unit includes full south building roof rights (an unfinished additional 27x21 area). Both finished decks feature premium, low-maintenance composite decking and gas line hookups. Unbeatable location: a 0.1-mile walk to the CTA Red Line and just half a mile to Andersonville's beloved independent shops and restaurants, a downtown express bus stop, and the attractions of Uptown-historic music venues, a climbing gym, international markets and more. The lakefront is under a mile away. Coffee shops, grocery stores, bakeries, gyms, parks, and museums are all just steps from your door. Well-maintained building with engaged, friendly neighbors and healthy reserves. A rare opportunity to own a turn-key penthouse in a welcoming, diverse community where there's always something to do nearby. The 2021 rehab included all new electrical, plumbing, as well as new water and sewer service lines. Spray foam insulation was added for increased comfort and energy savings. There is a layer of concrete between each floor providing excellent privacy and quiet.

1226 W Winnemac Avenue Unit #3S, Chicago
$400,000
2 Beds ⋅ 1 Baths ⋅ 12605524 MLS ⋅ CLOSED Status
LOCATION, LOCATION, LOCATION!!! This gorgeous and distinguished greystone building sits just a few short blocks East from the vibrant heart of Andersonville, and about the same distance West of the lakefront, with its great walking/biking trails, and powder-sand beaches! This great 2-bed/1-bath condo combines timeless character with a custom-designed open floor plan and perfectly proportioned living spaces throughout. From the moment you enter, you'll appreciate the bright and airy feel of the high ceilings, hardwood floors, and easy flow, designed for both comfortable everyday living and effortless entertaining. The expansive living room is filled with natural light, and is anchored by a lovely gas fireplace - a perfect setup to stay cozy & warm on those cold Chicago Winter nights! Large doors next to the fireplace open directly to the oversized private deck which spans the full width of the unit. This expansive outdoor living space provides the perfect setting for morning coffee, dining al fresco, or relaxing with friends. The beautifully-designed kitchen features rich Cherry cabinetry, stainless steel appliances, ample storage, and an open connection to the main living area with room for a dining table in between. The spacious primary bedroom offers a peaceful retreat with excellent storage options, including a walk-in closet, and built-in shelving. Enter the second bedroom though lovely French doors, and find flexibility for guests, a home office, or a workout or crafting space! Additional highlights include in-unit laundry, an assigned outdoor parking spot, and a truly move-in-ready home available for immediate occupancy. Don't miss your opportunity to live in this unbeatable location just moments from Lake Michigan, the CTA Red Line, neighborhood parks, and the premier dining, shopping, coffee shops, nightlife, and retail corridors along N Clark and N Broadway. Schedule your showing TODAY!!!

1234 W Winnemac Avenue Unit #4, 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
$480,000
2 Beds ⋅ 2 Baths ⋅ 12612390 MLS ⋅ CLOSED Status
Welcome to 4425 N Racine Ave #2N-a beautifully updated, sun-filled home offering the perfect blend of space, style, and flexibility in the heart of Uptown. Expansive windows fill the open-concept living and dining area with natural light, anchored by a cozy fireplace-ideal for both relaxing and entertaining. The kitchen, updated in 2023, features modern finishes, ample storage, and a seamless flow into the main living space. The oversized primary suite offers a true retreat with a spa-like bath, including a double vanity, separate shower, and jacuzzi tub. A spacious second bedroom with charming wainscoting sits next to a full second bath, perfect for guests or a home office. Step outside to your large private rear deck-an ideal extension of your living space for relaxing or hosting. Enjoy in-unit laundry, central heat and air, and garage parking included. Rental-friendly and investor-friendly, this home offers both comfort and long-term flexibility. All just moments from the CTA, Southport Corridor, lakefront, dining, and shopping.

4425 N Racine Avenue Unit #2N, Chicago
$1,025,000
3 Beds ⋅ 3 Baths ⋅ 12609846 MLS ⋅ CLOSED Status ⋅ Andersonville BLDG.
This is the one you've been waiting for! Incredible opportunity to own this stunning, 2400 square foot newer construction 3BR/2.5BA duplex in the heart of Andersonville, one of Chicago's most vibrant and exciting neighborhoods! This meticulous and modern 24 foot wide south facing home is better than new construction, featuring a generously sized main living/dining space that opens out to a massive 240 sq. ft. covered terrace with composite wood decking, ideal for entertaining, relaxing, grilling, and soaking in the sunlight. Beautiful open white kitchen has quartz counters, lrg breakfast bar, stainless Bosch appliances, undermount lighting and glass subway tiled backsplash. The large primary suite is conveniently located on the main floor and includes a walk-in organized closet, double quartz vanities, a walk-in shower, Grohe & Toto fixtures & heated flooring. This level is complete with a powder room, coat closet & pantry. Downstairs, you will be blown away by an absolutely enormous, extra wide family room with 10 foot ceilings, flooded with light! In this space, enjoy relaxing on an oversized sofa watching the latest latest Netflix hit, entertaining by the built-in wet bar with wine cooler & trendy open shelving, or using the space for a multitude of other things. The lower level also includes equally sized 2nd & 3rd bedrooms with ample closets and a sleek, white bathroom with double quartz vanity, quartz tiling and cozy heated floors. The full laundry room with size-by-side Maytag front loading washer & dryer complete this level. This fabulous home also boasts 8 foot doors throughout, extra storage in basement, and garage parking space. Incredible A+ location on tree-lined street, close to Red Line Train/bus lines, and right around the corner from all of the exciting restaurants, coffee shops, art galleries, boutiques, nightlife and so much more that Andersonville has to offer!

1470 W Winona Street Unit #102, 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
$816,519
3 Beds ⋅ 3 Baths ⋅ 12501283 MLS ⋅ CLOSED Status
Experience penthouse living that truly feels like a single-family home nestled in between iconic Uptown and Andersonville. This rare 3-story residence sits on a charming tree-lined street and features an extra-wide floor plan with expansive room sizes, hardwood floors throughout, soaring ceilings and incredible natural light. Designed for both comfort and entertaining, the home showcases a dramatic two-sided custom fireplace between the living and dining areas plus an oversized eat in kitchen with generous workspace. Two private balconies provide outdoor retreats-one off the main living area and another from the spacious second level primary suite. The suite boasts vaulted ceilings, double closets and a private bath complete with double vanities, steam shower, and a soaking tub. There are an additional 2 bedrooms and full bath on this floor. The third-floor family room offers versatile living space ideal for a home office, studio, media room, or guest suite. Parking - no problem, garage space included. Perfectly positioned just two blocks from Clark Street's vibrant shops and restaurants, 1.5 blocks to the Red Line, and four blocks from the lakefront, with an express bus nearby for a quick 10-minute commute downtown.

1225 W Carmen Avenue Unit #2N, 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
$955,000
3 Beds ⋅ 2 Baths ⋅ 12592014 MLS ⋅ CLOSED Status
Meticulously maintained and perfectly positioned, this rare 3BD/2BA simplex penthouse in the heart of Andersonville offers the ultimate blend of modern luxury and expansive private outdoor living. Built in 2018, this all-brick residence retains its "like-new" luster with high-end finishes and an intelligent, open-concept layout. The light-filled interior features a stunning living area anchored by a gas fireplace, flowing into a chef's kitchen with premium Thermador appliances and a dedicated dining space. Step out onto the wide front balcony to enjoy morning coffee overlooking a quiet, tree-lined one-way street. The primary suite is a true retreat, featuring a private back balcony, a large walk-in closet, and a spa-inspired ensuite bath with heated floors and steam shower. Two additional generous bedrooms are located on the main level. Ascend to the versatile upper-level bonus space-ideal for a high-performance home office-which opens to a massive private rooftop deck with breathtaking, unobstructed views of the Chicago skyline. This location is a commuter's dream, offering effortless access to both the Red Line and the UP-N Metra, placing the entire city within reach. Includes 1 garage space and storage. This is a pristine, move-in-ready asset in one of Chicago's most coveted walk-to-everything pockets.

1355 W Winnemac Avenue Unit #3, 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
$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
$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
$783,000
4 Beds ⋅ 3 Baths ⋅ 12511591 MLS ⋅ CLOSED Status
East Andersonville/Uptown Location! Rare, extra-wide 4 bedroom/2.5 duplex with private entrance and an atypical, wide design that lives like a single-family home. This new-construction residence offers a smart, functional layout ideal for today's lifestyle, featuring a spacious living and dining area with access to a private rear deck, in a addition to a garage roof deck for exceptional outdoor living. Contemporary kitchen includes custom cabinetry, quartz countertops, premium stainless steel appliances with a bar fridge. The luxurious primary suite features a walk-in closet and spa-inspired bath with heated floors and double vanity. One bedroom is conveniently located off the main level, perfect for guests, office use, or flexible living. Hardwood floors flow throughout, complemented by full-size laundry, custom blinds, and ample storage. Unit includes a garage spot. Constructed of steel siding, brick and block, this stately building stands tall on a quiet, one-way, tree-lined street. Pet friendly building. Steps to cobblestone-lined Argyle Street and neighborhood favorites like Milly's Pizza and First Sip Cafe, plus authentic global cuisine. Mariano's, Whole Foods, and Target are nearby, along with beautiful lakefront beaches, parks and bike paths. Enjoy quick access to Andersonville, the L and DuSable Lake Shore Drive.

4932 N Kenmore Avenue Unit #1W, Chicago
$715,000
3 Beds ⋅ 3 Baths ⋅ 12458837 MLS ⋅ CLOSED Status
Welcome to this extra-wide Andersonville 3-bedroom, 2.5-bath duplex down, set in an intimate 4-unit building. It sits on a quiet street in beautiful Andersonville. With soaring 10-foot ceilings, graceful archways, and windows on three sides, the home is flooded with natural light across both levels and offers the feel of a single-family residence. The showstopper kitchen has been completely remodeled, featuring brand-new stainless steel appliances, modern cabinetry, stylish backsplash, quartz countertops, and an oversized island perfect for entertaining. A separate formal dining room and living room are connected by a striking two-sided fireplace, while hardwood floors throughout the main level add warmth and elegance. Downstairs, the newly designed primary suite boasts a spa-caliber bathroom with a steam shower, soaking tub, and dual vanity. Both the second full bath and half bath have been fully updated, as has the spacious laundry room, now complete with full-size front-load machines and a utility sink. All three bedrooms are thoughtfully situated on the same level. Two private outdoor spaces extend the living area, and garage parking is included. Perfectly located neat the lakefront, CTA buses and trains, Carmen play lot, and all of Andersonville's beloved shops and restaurants, this home truly blends modern comfort with neighborhood charm.

1225 W Carmen Avenue Unit #1N, Chicago
$828,000
3 Beds ⋅ 3 Baths ⋅ 12425549 MLS ⋅ CLOSED Status
Welcome home to this stunning 3BR/3BA duplex-down in the heart of Andersonville, Tired of cookie-cutter? This floorplan is incredibly unique, functional, and provides for optimal entertaining space. The main floor has the open concept floorplan everyone is looking for with the kitchen overlooking the spacious living room, and an adjacent separate dining space. The inviting living room is highlighted by a wood burning fireplace, custom mantle, and has direct access to the front balcony overlooking the beautifully manicured front common patio area. The kitchen has been updated and is adorned with Espresso cabinetry, Quartz countertop, large separate pantry, breakfast bar, subway tile backsplash, and all replaced stainless steel appliances (sans dishwasher). Newly gut renovated primary bathroom provides for a spa-like urban oasis, as well as a fully updated guest bathroom. Gorgeous hardwood floors run throughout the main level, including newer hardwood floors in both main floor bedrooms. Lower level family room provides a cozy retreat featuring a second fireplace, radiant heated flooring, and adjacent wet bar with integrated beverage refrigerator. Thoughtfully designed office/den space directly adjacent to the family room has been designed with French doors, built-in desk/working space, and custom shelving. Highly upgraded with attention to detail including designer light fixtures, custom wainscoting, in-ceiling speakers on both levels, and smart storage solutions throughout. Outdoor parking space and separate storage unit included! Boutique 5-unit building that is 100% owner occupied with healthy reserves. Situated on a picturesque tree-lined street, this walk-to-everything Andersonville location has access to the Argyle Red Line train, the lakefront, and countless bars, restaurants, and shops that make Andersonville so special!

1313 W Carmen Avenue Unit #1N, Chicago
$606,000
3 Beds ⋅ 3 Baths ⋅ 12416865 MLS ⋅ CLOSED Status
Craving outdoor space? Nestled in the vibrant Buena Park neighborhood-and just 3 blocks from Lake Michigan, this 3-bedroom, 3-bath duplex-down delivers the ultimate indoor-outdoor lifestyle with an expansive extra large exclusive private deck. Inside, the largest home in this intimate 2008 all-brick walk-up lives like a single-family residence: 9-ft ceilings with crown molding, a stone-clad gas fireplace anchoring an open living/dining area, and a cook's kitchen boasting soapstone counters, peninsula seating, walk-in pantry, and stainless steel appliances. Enjoy two spacious bedrooms and two full baths on the main floor-including a king-sized primary suite with double vanity, soaking tub, and separate shower-plus side-by-side laundry. Downstairs, new carpet (2020) cushions a flexible family/office zone, third bedroom, and full bath-ideal for guests, workouts, or WFH. 2024 high-efficiency furnace with smart thermostat and a 2006 water heater. One assigned covered exterior parking space sits behind a newly upgraded electronic fenced garage (2025).

927 W Agatite Avenue Unit #1S, Chicago
$496,000
2 Beds ⋅ 2 Baths ⋅ 12398211 MLS ⋅ CLOSED Status
Welcome to this beautifully updated, sun-filled 2-bedroom, 2-bath corner home with 2 parking spaces in a boutique elevator building. With south-facing oversized windows, this unit is drenched in natural light throughout the day. The spacious living room features custom built-ins surrounding a sleek, tiled gas fireplace, a built-in bar area perfect for entertaining, and direct access to a charming private balcony. The open kitchen is thoughtfully designed with granite countertops, under-cabinet lighting, an undermount sink, updated stainless steel appliances, and a large island for dining or prep. Smartly designed with a split floor plan, both bedrooms are tucked away from the main living space, offering privacy and a peaceful retreat. The generous primary suite boasts two professionally organized closets and dual-layer sheer/blackout shades. The spa-like en-suite bath includes double vanities, heated floors, a soaking tub, and a separate shower. The unit comes with two prime parking spaces, one garage spot and a second exterior space. All this just steps to the train, and minutes to Montrose Beach, Southport Corridor, Uptown, Wrigleyville, and Andersonville. Easy access to Lake Shore Drive makes commuting a breeze.

1100 W Montrose Avenue Unit #207, Chicago
$665,000
4 Beds ⋅ 3 Baths ⋅ 12397039 MLS ⋅ CLOSED Status
Tucked just steps away from the heart of Andersonville, this 4-bedroom, 3-bathroom condo tells a story of care, comfort, and quiet refinement-written by its original owner and now ready for its next chapter. From the moment you step inside, the warmth of newly refinished hardwood floors underfoot and the soft glow of fresh paint on the walls greet you like an old friend. Sunlight pours into an open-concept living space anchored by a brand-new gas fireplace, its hand-rebuilt mantle inviting books, photographs, or a glass of wine after a long day. The smart thermostat has already adjusted the temperature just right. The kitchen, reimagined in 2024 with sleek new countertops and backsplash, opens naturally into the main living area-perfect for quiet mornings or hosting dinner with friends. Just beyond, a private deck awaits. Outfitted with a TV and space to lounge, it's your own outdoor retreat for movie nights under the stars or catching a Cubs game al fresco. Downstairs, the primary suite is a true haven. Dual vanities, a jetted Jacuzzi tub, and the sense of separation from the rest of the home offer daily escape. Two additional bedrooms provide space for guests, children, or creative pursuits, while the fourth room stands ready to become a home office, reading room, or formal dining space-whatever your lifestyle demands. Closets throughout the home were custom-designed in 2023 for efficiency and beauty, a reflection of the meticulous attention that has gone into every detail. The lower level, newly carpeted in June 2025, offers yet another cozy space to retreat or entertain. And the perks go beyond the unit itself. With one dedicated parking space and easy, permit-free street parking, coming home is always easy. Shared rooftop deck offer sweeping views and space to gather, while your own private rooftop storage room means you never have to sacrifice on space. And the location? It's as ideal as it gets. Just steps from the newly rebuilt Argyle Red Line, across the street from a peaceful park, and around the corner from an award-winning Montessori school. In minutes, you're in the heart of Andersonville, surrounded by boutiques, bakeries, and the kind of community people seek for a lifetime.

1257 W Carmen Avenue Unit #1S, Chicago
$519,000
2 Beds ⋅ 3 Baths ⋅ 12395993 MLS ⋅ CLOSED Status
Situated in the heart of the historic Uptown Entertainment district just steps from multiple concert venues, the lakefront trail, and Andersonville, this turn-key 2 BD / 2.5 BA duplex down condo spans over 1,700 square feet with two private outdoor areas plus ample garage and storage space. Upstairs features an open concept floor plan with a large living and dining area combo outfitted with custom Hunter Douglas remote-controlled blinds flanking one of two gas fireplaces within the unit. The chef's kitchen has cherry cabinets, granite countertops, and stainless steel appliances. The main level is complete with hardwood floors throughout, a powder room, a spacious 2nd bedroom, and an oversized en-suite primary bedroom featuring a spa-like bathroom with updated walk-in shower and jacuzzi tub. Enter the sprawling lower level and experience 12 ft ceilings, a large family room entertainment area with the second gas fireplace, a full bathroom, walk-in laundry room with side-by-side washer/dryer, loads of additional storage, Rheem HVAC (2021), and a Navien tankless water heater (2019). Completing the unit is a separate private 9x3 storage room, front and rear private deck space, wired intercom, security system, and an attached garage. Low HOA fees are the cherry on top. Don't wait to visit this spectacular Uptown property!

4660 N Winthrop Avenue Unit #1N, Chicago
$532,500
3 Beds ⋅ 2 Baths ⋅ 12343808 MLS ⋅ CLOSED Status ⋅ Margate Park BLDG.
This stunning 2,000 sq ft unit is filled with natural light and features hardwood floors throughout! The spacious main living area offers a designated dining space and flows seamlessly into a large kitchen, complete with new upgraded stainless steel appliances, a granite island, 42" cabinets, and a beautiful single-basin copper sink and faucet. Off the living room, enjoy a covered balcony - the perfect spot to relax and city watch! Down the hall, you'll find three bedrooms and two bathrooms. The first bedroom, which connects to the hall bathroom, easily fits a queen-sized bed and additional furniture. The primary bedroom features its own ensuite bathroom, while the third bedroom is also generously sized for a queen bed plus furniture. A stackable in-unit washer and dryer are conveniently located in the hallway. At the end of the hall, a back porch provides an ideal space for a BBQ grill! One exterior parking spot is included in the price. Located in a prime Uptown spot, you're just a block from the lake and Foster Street Beach, and one block from Mariano's grocery store. Plus, you're steps away from fantastic dining options on Argyle Street, including Na Hang Vietnam, Furama, and Sun Wah BBQ. Popular neighborhood spots like Tweet and Big Chicks are also just around the corner!

5016 N Sheridan Road Unit #1, Chicago
$820,000
3 Beds ⋅ 3 Baths ⋅ 12348330 MLS ⋅ CLOSED Status
A Nature Lover's Dream in the Heart of Andersonville! Welcome to this rarely available, 3 bedroom /3 bathroom single-family home on one of Andersonville's most picturesque, tree-lined streets-just one block from vibrant Clark Street! Nestled in one of Chicago's hottest North Side neighborhoods, this home offers the perfect balance of urban convenience and tranquil, green living. The current owner has lovingly transformed the expansive backyard into a lush, curated nature garden-a true private oasis in the city. Birds, butterflies, and blooms abound in this serene outdoor space, ideal for morning coffee, peaceful evenings, or entertaining under the stars. Step out from the primary suite's private deck and take in the view of your beautifully manicured retreat. Inside, the home features a spacious and functional layout with 3 bedrooms plus a den, and 2 full bathrooms upstairs, offering plenty of room for relaxation and work-from-home flexibility. The open living areas, skylights, and thermal pane windows create a warm and airy atmosphere throughout. The main level has a separate kitchen, huge dining room that would accomodate your largest table, separate living room, there is an option to have a 1st floor bedroom which has currently been opened up to a very intimate family seating room. There is a full bathroom and laundry room on the 1st floor level. The unfinished basement includes a forth bathroom rough-in, offering expansion potential to suit your needs. Additional features include gas forced-air heat, central air. The property has also been successfully run as a high-performing Airbnb, consistently earning $7K-$9K per month, making this a perfect opportunity for investors, owner-occupants, or those seeking a hybrid live/income-producing home. Located just steps from Andersonville's best shops, restaurants, the farmer's market, and the Red Line, this is city living at its most charming.

1435 W Winnemac Avenue, Chicago
$660,000
4 Beds ⋅ 3 Baths ⋅ 12331953 MLS ⋅ CLOSED Status
This 4BR, 3BTH duplex down has a fantastic layout, and with approximately 2600 ft.2 of living space, it's as large as many single family homes in the area, but with lower property taxes. It also sits in a superior location at the nexus of three of Chicago's most vibrant neighborhoods including the Arglye shopping and restaurant district in Uptown, Edgewater Beach and Andersonville. Just 2.5 blocks from the Red Line "L" and only 3 blocks from Margate Park and the lakefront and with a plethora of grocery stores and restaurants all right outside your door, it simply doesn't get better than this. This home has an open concept design with a very large kitchen that offers tons of counter space and storage, including a separate pantry, as well as all stainless appliances, and a peninsula with room for bar stool seating. Great room adjacent to the kitchen could be used as a living room or dining room. There's also a huge family room in the lower level with nicely appointed wet-bar, perfect for entertaining. A spacious 3rd bedroom with walk-in closet, a full bath, laundry room with side by side laundry and a large 5 by 11 ft storage room finish out the lower level. The 4th bedroom is on the main floor close to the kitchen and has French Doors to be flexibly used as a dining room, office or bedroom. Primary bedroom suite has double sinks, a large steam shower with body sprays and overhead shower head, a makeup vanity for additional space and storage, a walk-in closet and a private balcony overlooking a small private patio area. The building also has a common roof deck with exceptional views and outdoor furniture for all to enjoy. All this in a well cared, full brick building with a great association. Garage parking spot is included in the price.

5018 N Kenmore Avenue Unit #1N, 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
$552,725
4 Beds ⋅ 2 Baths ⋅ 12300391 MLS ⋅ CLOSED Status
Wow! Endless space awaits you in this south facing, all brick building. Extra large 4 bedroom plus 2 full bath duplexed home with private outdoor space and assigned parking in Margate Park. Enjoy the perfect floor plan that gives tremendous flexibility: more than ample room for working from home, entertaining groups large and small and enjoying the convenience of a home gym. The main level provides generous living and dining areas, with the outdoor space located perfectly: immediately off the kitchen. Enjoy relaxing and watching TV with a woodburning fireplace conveniently located in the living room. The kitchen features granite countertops plus all stainless appliances, with ample counter space for cooking and preparing to grill on your private deck. The large primary en suite offers an organized walk-in closet plus a large bath. The second full bath features a walk-in steam shower featuring dual shower heads, bench and body spray. The oversized family room showcases exposed brick detailing. Hardwood floors and wonderful storage throughout this home. The separate laundry room features side by side washer and dryer plus extra cabinetry for full function of the space. There is also dedicated storage located outside the unit, in addition to a bike room. Space pac system of central air plus steam heat, with heat included in the assessment. Pet friendly building. Steps to everything: lakefront, CTA Red Line, shopping, grocery, dining. Minutes to Andersonville. This one will not disappoint!

852 W Lakeside Place Unit #1E, Chicago



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