View All Uptown Chicago IL Homes with Large Yard Listings

$450,000
2 Beds 1 Baths 12613646 MLS CLOSED Status
This gorgeous, sun-drenched condo is a vintage lover's dream. Located next to a park, this spacious home is light-filled, airy and boasts with 10ft tall ceilings with an open floorplan. Featuring period woodwork throughout, a lovely decorative fireplace with bookcases, and the original mosaic tile floor in the sitting/sunroom plus custom built-in bookshelves for extra storage or display space in the office/library/sitting room. The clever distribution and demarcation of areas allow for flexible use as dining room, living room, and office and is a great space for entertaining guests or unwinding with a book. The kitchen is equipped with white cabinets, a tile backsplash, and a new Bosch dishwasher (2021) and KitchenAid range and hood (2021) and has a seating area on the back deck just off it. The bathroom features custom hand painted tile and updated hardware. The large primary bedroom has the original built-in dresser and good closet space. A built-in window AC unit (2024) comfortably cools the living and dining rooms, and the unit is equipped with vents to have AC filtered throughout should the new owner wish to install a new HVAC system in the walk-in closet off the entryway. There is lots of storage, both inside the unit and out, including a huge coat closet, a walk-in closet in the second bedroom, and a dedicated storage room in the basement. Also in the basement is the building's free laundry room and storage for bikes. If you need a place for your car, great! It comes with deeded garage parking. On top of it all, you don't have to limit your green thumb to houseplants if you live here as there's a beautiful yard with a bevy of perennials plus a south-facing raised bed garden for growing veggies. It's perfectly located for commuting, with the red line one block away and the Sheridan express bus to downtown two blocks down Foster. It's also short walking distance to the lake/beach/bike path, one block to two grocery stores (Mariano's and Jewel) and an easy walk to all the restaurants, shops, and great venues in Andersonville and Uptown. The building is pet friendly, owner-occupied, and has a well-run association with ample reserves and no upcoming specials or big projects. It's a special one--don't miss it.

5125 N Winthrop Avenue Unit #1F, Chicago

$570,000
3 Beds 2 Baths 12613818 MLS CLOSED Status
This Sheridan Park condo is a true breath of fresh air, blending timeless character with thoughtful updates throughout. Rich hardwood floors set the tone, while vintage details, like the beautifully refinished peer mirror at the entry, add warmth and charm. The sun-filled living room feels both inviting and spacious, centered around a classic wood-burning fireplace and opening to a generous brick terrace overlooking a picturesque, tree-lined street. A versatile third bedroom, accessed through elegant French doors, offers excellent flexibility, ideal as a private office, guest room, or creative space, complete with great natural light and ample closet storage. The expansive kitchen is designed for both everyday living and entertaining, featuring newer appliances, a breakfast bar, and a large eat-in area, along with pantry and in-unit laundry. It flows seamlessly into a comfortable family room, creating an easy, connected living space. The primary suite comfortably accommodates a king-sized bed and includes an en suite bath, while the second bedroom is equally spacious and bright. Flexible living areas throughout make this home as functional as it is inviting. Outdoor space is just as appealing, with a sizable deck off the kitchen leading down to a shared grassy yard and a one-car garage. Additional storage in the basement adds to the home's convenience. Tucked on a quiet street yet just moments from Uptown's vibrant dining and shopping scene, the Red Line, and close to Andersonville, Wrigleyville, Lincoln Square, and the lakefront, this location truly offers the best of city living.

4415 N Racine Avenue Unit #2S, Chicago

$475,000
3 Beds 2 Baths 12598298 MLS CLOSED Status
Spacious Vintage Condo in Prime Location! Step into this charming vintage 3-bedroom, 2-bath home offering generous living space and timeless character. The oversized living/dining room flows seamlessly into a large kitchen and an additional sunroom-perfect for a home office, reading nook, or extra lounge space. The renovated kitchen (2022) features new countertops, backsplash, cabinetry, and black stainless steel appliances. Both bathrooms have been tastefully refreshed with brand-new counters, sinks, faucets, and backsplash. Updated overhead lighting enhances the entry, living room, hallway, office, and two bedrooms. Recent mechanical updates include a new hot water heater, furnace, and air conditioning condenser (2024), along with an in-unit washer and dryer (2022). The building completed a full roof repair in 2016. Additional features include a private storage cage, bike storage, and access to approximately 1,200 sq ft of shared basement space. Enjoy outdoor living in the beautifully maintained yard with patio, lighting, and seating-ideal for relaxing or entertaining. Perfectly located just 1/2 mile from iconic venues like the Green Mill Cocktail Lounge, Aragon Ballroom, and Riviera Theatre. Outdoor enthusiasts will love the quick access to Montrose Beach and the 18-mile lakefront trail. The gracious sellers are offering to cover one year of parking at the Weiss parking garage! Fantastic space, unbeatable location-don't miss this opportunity!

829 W Lakeside Place Unit #1W, 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

$1,050,000
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

$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

$852,000
3 Beds 3 Baths 12292276 MLS CLOSED Status Andersonville BLDG.
***HIGHEST AND BEST OFFER SUBMISSION DEADLINE 5PM MONDAY, 2/24*** -RARE OPPORTUNITY IN THE HEART OF SOFO-ANDERSONVILLE: EXPANSIVE 2,600+ SF DUPLEX WITH MODERN UPDATES & PRIME LOCATION- Nestled in the sought-after SOFO-Andersonville neighborhood, this rarely available duplex offers a generous 2,600+ square feet of refined living space. Boasting two oversized living areas, three spacious bedrooms, and three stylish bathrooms, this home is the perfect blend of comfort and convenience. Located just steps from Clark Street, yet tucked away on peaceful, tree-lined Carmen Avenue, you'll be immersed in the vibrant culture, dining, and shopping that Andersonville is known for. Upon entering, you're greeted by an elegant, open-concept living and dining area with a modern fireplace and an impressive two-story window wall that overlooks the casual living space below and floods both with natural light. The updated kitchen features sleek quartz countertops, stainless steel appliances, a large island, and a well-organized pantry with pull-out shelving. On the same level, the oversized primary en suite serves as a true retreat, complete with a newly renovated spa-like bathroom and a spacious walk-in closet with custom modular organizers. A second generously-sized bedroom, another fully updated bathroom, and a private deck accessible from both the hallway and primary en suite round out this floor. The lower level continues to impress with 9-foot ceilings and an enormous 500 sf recreation room, perfect for entertaining or relaxing, complete with its own fireplace and direct access to a private, sunken patio. A large third bedroom and another full bathroom complete this level, ensuring ample space for all your needs. Additional highlights include a large utility room with brand-new side-by-side laundry, recently replaced HVAC system (2021) and water heater (2021). An overhead sewer and sump pump system ensure the space remains dry. Storage is plentiful throughout, including a spacious storage room just behind the unit in the common area. The property sits on a rare, 180-foot deep lot, where six owners share a park-like, fully fenced yard-an ideal space for both relaxation and play. Included with the unit is a garage parking space along with extra storage. With its perfect mix of modern amenities and unbeatable location, this duplex is truly a rare find.

1465 W Carmen Avenue Unit #1W, Chicago

$395,000
2 Beds 1 Baths 12191474 MLS CLOSED Status
This gorgeous, sun-drenched condo is a vintage lover's dream--especially if you want to have an updated, functional kitchen to go with it. Located on the top floor and next to a park, it affords wonderful privacy, expansive treetop and city views, and incredible light that illuminates the generous 1400sf space. Entering the condo, you'll be struck by the 10ft. tall ceilings, open floorplan, and by the well-preserved hardwood floors and period woodwork throughout, lovely decorative fireplace with bookcases, and the original mosaic tile floor in the sitting/sunroom. The clever distribution and demarcation of areas allows flexible use as dining room, living room, and office and is a great space for entertaining guests or unwinding with a book. The updated kitchen is equipped with a plethora of white cabinets, stainless Bosch appliances and backsplash, plus granite counters, and has a seating area on the back deck just off it. The large primary bedroom features the original built-in and good closet space. There is lots of storage, both inside the unit and out, including a huge coat closet, a walk-in closet in the second bedroom, and a dedicated storage room in the basement. Also in the basement is the building's free laundry room and storage for bikes. If you need a place for your car, great! It comes with deeded garage parking. On top of it all, you don't have to limit your green thumb to houseplants if you live here as there's a beautiful yard with a bevy of perennials plus a south-facing raised bed garden for growing veggies. It's perfectly located for commuting, with the red line one block away and the Sheridan express bus to downtown two blocks down Foster. It's also short walking distance to the lake/beach/bike path, one block to two grocery stores (Mariano's and the Jewels) and a ten minute walk to all the restaurants, shops, and great venues in Andersonville and Uptown. The building is pet friendly, owner-occupied only, and has a well-run association with ample reserves and no upcoming specials or big projects. It's a special one--don't miss it.

5125 N Winthrop Avenue Unit #3F, Chicago

Start Your Search



The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of Midwest Real Estate Data LLC. Real Estate listings held by brokerage firms other than our company are marked with the MRED Broker Reciprocity logo or the Broker Reciprocity thumbnail logo (the MRED logo) and detailed information about them includes the names of the listing brokers. Some properties which appear for sale on this website may subsequently have sold and may no longer be available. The accuracy of all information, regardless of source, including but not limited to square footages and lot sizes, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals. The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Copyright 2026 MRED LLC. All rights reserved.

Based on information submitted to the MLS Grid as of . All data is obtained from various sources and has not been, and will not be, verified by broker or MLS Grid. MRED supplied Open House information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.

The Digital Millennium Copyright Act of 1998, 17 U.S.C. § 512 (the DMCA) provides recourse for copyright owners who believe that material appearing on the Internet infringes their rights under U.S. copyright law. If you believe in good faith that any content or material made available in connection with our website or services infringes your copyright, you (or your agent) may send us a notice requesting that the content or material be removed, or access to it blocked. Notices must be sent in writing by email to DMCAnotice@theMLSGRID.com.

The DMCA requires that your notice of alleged copyright infringement include the following information: (1) description of the copyrighted work that is the subject of claimed infringement; (2) description of the alleged infringing content and information sufficient to permit us to locate the content; (3) contact information for you, including your address, telephone number and email address; (4) a statement by you that you have a good faith belief that the content in the manner complained of is not authorized by the copyright owner, or its agent, or by the operation of any law; (5) a statement by you, signed under penalty of perjury, that the information in the notification is accurate and that you have the authority to enforce the copyrights that are claimed to be infringed; and (6) a physical or electronic signature of the copyright owner or a person authorized to act on the copyright owner’s behalf. Failure to include all of the above information may result in the delay of the processing of your complaint.

Some listings have been excluded from this website.

Uptown, Chicago IL · Curated MLS Search

Homes with Large Yard in Uptown, Chicago IL

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

Browse Active Listings