View All Uptown Chicago IL Homes with Garden Listings

$279,000
2 Beds 1 Baths 12745173 MLS ACTIVE Status
Charming Garden Unit in the Heart of Uptown - Your Own Private Entrance! Welcome home to this beautifully updated 2-bedroom, 1-bath garden unit tucked inside a stately, gated brick building in one of Chicago's most vibrant neighborhoods. This isn't a typical garden unit - it's bright, thoughtfully finished, and comes with two private entrances (front and back), so you never have to share a hallway if you don't want to. Step inside to a crisp kitchen with marble herringbone backsplash and stainless-steel appliances, opening onto a spacious living and dining area with room to entertain. The primary bedroom easily fits a king bed and has generous closet space, while the second bedroom and a large flexible den/office give you room to work from home, set up a workout space, or carve out a craft room - whatever your life needs right now. In-unit washer/dryer, extra storage, and tasteful modern finishes throughout round out the interior. Outside, residents share a genuinely lovely backyard garden - a rare find in the city. Why this location is special: This building sits in the heart of Uptown's entertainment district, close to the historic Green Mill and legendary venues like the Aragon Ballroom and Riviera Theatre. Just minutes from: The lakefront, the new Red Line Lawrence stop and the Purple Line Express at Wilson, Mariano's, Jewel-Osco, Target, and Aldi, neighborhood schools, some of the city's best restaurants and nightlife. The details that matter: HOA just $198/month - remarkably low for the neighborhood, covering building upkeep and shared spaces. a real community, not a revolving door of renters. Gated entry for added security. Street parking with a residential permit (no dedicated garage spot included). This is a rare opportunity to own in Uptown at an accessible price point, in a building people actually stay in.

4733 N Kenmore Avenue Unit #4, Chicago

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

4633 N Winthrop Avenue, Chicago

$1,050,000
8 Beds 4 Baths 12431216 MLS CLOSED Status
Extraordinary opportunity to own this classic Chicago mansion with 8 bedrooms on a 50 x 150 foot lot. This RT-4 zoned, 1905 stone home boasts 3 floors of living space and has undergone restoration work to reveal some of its jaw dropping vintage craftsmanship. Situated in an ideal Uptown location this property is located in close walking distance to the Wilson Red Line and Purple Line express lines, several bus lines and the Broadway Target and Aldi. Step through the gate and into your fully fenced in front and side yard complete with huge stone porch. A stunning floor mosaic greets you as you enter through a dual set of double wooden doors into the grand foyer with original stained glass and a resorted wooden staircase. Rich decorative hardwood flooring throughout this level welcomes you into a huge living room space with an enormous formal dining room complete with coffered ceiling, custom cabinetry, buffet and extraordinary fireplace. An ample sized kitchen in the back of the house has been lovingly updated with modern stainless steel appliances including a dishwasher. The kitchen is flanked by both a laundry / storage room and walk-in pantry. An updated and convenient half bath located below the stairwell. Up the grand and ornate staircase you'll find two more floors of living space with 8 large bedrooms and 3 additional baths, which have been updated. The room sizes are varied, but all large and homey. There is also a great room on the top floor with soaring ceilings that is currently used as a recreation room, but can also be used as a bedroom. The lower level is finished and could be updated to create even more living space. It has a newly updated boiler (2018) and is currently used as a large storage space. You'll feel the extra wide lot in the large backyard fitted with a stone patio, lawn and garden perfect for relaxing and entertaining. Additionally, the property comes with a total of 5 exterior parking spaces. The many possible uses for this home include; short term rental, development, TOD, commercial, or office spaces. Don't miss out on the opportunity to own this piece of Chicago history.

4516 N Sheridan Road, 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

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Uptown, Chicago IL · Curated MLS Search

Homes with Garden in Uptown, Chicago IL

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

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