Refine Search
Sort by
$402,000
2 Beds 2 Baths 12678326 MLS CLOSED Status
Welcome to Madison Place! This stunning penthouse-level 2-bedroom, 2-bathroom luxury condo is located in a meticulously maintained building in the heart of Skokie. The unit features a spacious open kitchen, a separate dining area, and a large family room that opens to your own private balcony-perfect for relaxing or entertaining. The primary suite includes a walk-in closet and a generously sized bathroom with a double vanity, separate shower, and soaking tub. Additional highlights include an in-unit washer and dryer, dedicated storage space, and parking in a heated garage. Ideally situated, Madison Elementary School is directly across the street, with vibrant Downtown Skokie, restaurants, shopping, and several parks all nearby. Public transportation is easily accessible, making commuting simple and convenient. The building also features a newly updated lobby and beautifully maintained grounds.

5055 Madison Street Unit #601, Skokie

$350,000
2 Beds 2 Baths 12575309 MLS CLOSED Status North Shore Towers BLDG.
Absolutely stunning, fully updated, and truly move-in ready, this spacious condo is located in a secure, well-established elevator building in a prime Skokie location. From the moment you step inside, you are welcomed by gleaming, bold hardwood floors that flow throughout the home and immediately highlight the impressive scale and sophistication of the space. The extra-large living and dining rooms offer an open and inviting layout and connect seamlessly to the beautifully updated kitchen, ideal for both everyday living and entertaining. The kitchen features a massive peninsula with breakfast bar seating, walls of cabinetry for exceptional storage, granite countertops, a stylish tile backsplash, a modern one-touch faucet, and stainless steel appliances. Double sliding glass doors lead to the large balcony while allowing abundant natural light to pour into the home. The front entry is thoughtfully designed with a generous coat closet plus a second closet that is a true shoe collector's dream, complete with sturdy built-in shelving. The primary suite is impressively sized and serves as a relaxing retreat, offering a large walk-in closet with custom built-ins and a beautifully updated en-suite bathroom with a tiled shower, glass door, and a large double-sink vanity. The second bedroom is also generously sized and features its own walk-in closet with built-ins. A full hallway bathroom with a tub conveniently connects to the laundry room with a stackable washer and dryer. Arguably one of the most updated units in the entire building, this sophisticated home delivers true penthouse vibes with its expansive rooms and high-end finishes throughout. Additional features include a private storage unit, trash chute, two assigned parking spaces in the heated garage, and an impressive list of amenities including an exercise room, sauna, party room, and outdoor pool. The location is exceptional, just minutes from Old Orchard Mall, fantastic dining options, everyday conveniences, healthcare facilities, and quick highway access that makes commuting downtown effortless. Do not miss this incredible opportunity. Schedule your private showing today.

9560 Gross Point Road Unit #404B, Skokie

$412,000
2 Beds 2 Baths 12367674 MLS CLOSED Status Optima Old Orchard Woods BLDG.
Bright northwest Optima Woods corner unit with 2 beds/2baths + den/office and private balcony to watch sunsets.This condo offers upgrades & picturesque views of the forest preserve & entry fountain. Beautiful upgraded hardwood & tile floors, upgraded stainless steel kitchen appliances; granite counters & 2 zoned furnaces/AC units,1 new in 2020, An extra large primary bedroom offers a generous 9 X 9 walk- in closet plus an office/den. The primary suite includes a shower w/body sprays and double sinks. This desirable 1488 sq ft unit also features a west facing balcony for afternoon sunshine & grilling, floor-to-ceiling windows with custom blinds, in-unit laundry plus spectacular forest views from every room. One indoor deeded & heated parking spot & storage locker. Pet-friendly building. Assessment includes heat, AC, water, gas, basic cable, scavenger, lawn care, snow removal & common insurance. Enjoy the use of a year-round indoor pool, sauna & whirlpool within the SAME building, plus a sundeck, a penthouse level workout room with breathtaking views, tennis courts, an enormous party room, dog park, onsite management, indoor guest parking - all on premises. Minutes to I-94 expressway, shopping, dining, movies, theater, hospital, bike trails, Niles North HS, Mariano's, Metra train, Skokie park district and more. Investor-friendly building. Tenant occupied but meticulously maintained. Photos shown were taken previously. Home warranty included for all appliances for greater peace of mind.

9655 Woods Drive Unit #402, Skokie

$975,000
4 Beds 3 Baths 12204562 MLS CLOSED Status
This is a stunning penthouse condo located in the highly desirable Optima Old Orchard Woods Building. This 4 bed 3 bath penthouse boasts over 3800 square feet, high quality finishes, and 9 ft floor-to-ceiling windows throughout the home! Enjoy the unbeatable views of the city skyline and forest preserve! Stunning stainless steel Viking, Thermador, and Sub Zero appliances in the kitchen! The living area features cherry hardwood floors and great open concept space. The bedrooms are spacious and feature great walk in closet areas! This building has amazing amenities including 3spots in the heated parking garage, fitness center located on the same floor, smart car charging station, tennis court, indoor pool, hot tubes, BBQ areas, valet cleaners, and party room! This home is close to the local public transportation, schools, and shopping. Enjoy incredible luxury high rise living!

9715 Woods Drive Unit #1902, Skokie

$395,000
2 Beds 2 Baths 11847473 MLS CLOSED Status Madison Place BLDG.
Stunning Penthouse Retreat in the Heart of Skokie. Welcome to the epitome of luxury living in this exquisite two-bedroom, two-bath penthouse condo. Nestled in a modern, newer construction building, this residence offers a seamless blend of elegance, comfort, and convenience. Upon entering, you'll be immediately captivated by the soaring ceilings and the flood of natural light that illuminates the open-concept living space. The contemporary kitchen is a chef's dream, featuring top-of-the-line stainless steel appliances, sleek granite countertops, and abundant cabinet storage. For added ease, the unit includes a full-size in-unit laundry room. The generously sized bedrooms provide a serene escape, with the primary suite standing out as a true retreat. This haven boasts a spacious walk-in closet, a private balcony, and a luxurious spa bath with both a tub and a separate shower. It's the perfect sanctuary for relaxation. The highlight of this penthouse is the expansive 740-square-foot terrace, offering breathtaking views of the iconic Chicago skyline. This outdoor oasis has a shaded retractable awning and is ideal for entertaining guests, savoring a morning coffee, or unwinding with a glass of wine while enjoying the evening sunsets. It's a rare gem within the complex, providing a sense of privacy and additional light that truly enhances the living experience. Located just a short stroll from downtown Skokie, you'll have easy access to an array of shops, restaurants, and local amenities. Whether you're in the mood for a lively night out or a quiet night in, everything you need is within reach. The home also includes three garage parking spaces- a feature unique to this unit- one being a handicapped-accessible spot. Additionally, there are three roomy storage units conveniently located in front of each parking space, making organization and accessibility effortless. With its prime location on the northeast corner of the top floor, this penthouse not only offers incredible views but also a sense of tranquility and separation from other buildings. It's more than just a home; it's a lifestyle. Discover the unparalleled charm and sophistication of this stunning penthouse condo and make it your own!

5105 Madison Street Unit #610, Skokie

$855,000
3 Beds 3 Baths 12076331 MLS CLOSED Status Optima Old Orchard Woods BLDG.
Stunning penthouse condo in sought-after Optima Old Orchard Woods Oak building with two private balconies perfect for entertaining! Cherry hardwood floors in main living area. Enjoy unbelievable views of the panoramic city and forest. This beautiful designer 3 bedroom, 3 -bathroom condo features 9ft floor-to-ceiling windows and over 2500 square feet. The price includes 2 indoor heated parking spaces. Building amenities include indoor visitor parking, smart car charging stations, a fitness center, tennis court, year-round glass-enclosed indoor pool, hot tubs, picnic and BBQ area with grills, valet cleaners, and a fully renovated party room. This home is close to public transportation, expressways, Old Orchard Mall, and much more.

9655 Woods Drive Unit #1902, Skokie

$540,000
3 Beds 3 Baths 12049672 MLS CLOSED Status
PENTHOUSE CONDO LOCATED ON 20TH FLOOR IN SKOKIE OPTIMA BUILDING.MAGNIFICENT WESTERN VIEWS.3 BEDROOMS, 2.1 BATHS.4 PARKING SPACES(#785-788).2 BALCONIES.NEEDS SOME WORK, SOLD `AS IS`.SPECIAL ADDENDUM, PROOF OF FUNDS, CERTIFIED E.M. CHECK REQUIRED(MIN. $2,000).ROOM SIZES ESTIMATED.SELLER WILL NOT COMPLETED ANY REPAIRS.100% REAL ESTATE TAX PRO-RATION.BUYER RESPONSIBLE FOR UP TO 6 MONTHS OF HOA FEES AND ANY UPCOMING SPECIAL HOA FEES.BUYER RESPONSIBLE FOR VILLAGE BUILDING VIOLATIONS(IF ANY).PROPERTY TO REMAIN ON THE MARKET FOR 15 DAYS BEFORE SELLER WILL RESPOND TO OFFERS.SUBMIT OFFERS VIA ONLINE MANAGEMENT SYSTEM-SEE AGENT REMARKS FOR DETAILS.***DO NOT SEND OFFERS TO LISTING AGENT.***DO NOT SEND `BLIND OFFERS`-SEE PROPERTY FIRST.***NO ESCALATION CLAUSE OFFERS-SELLER WILL REJECT.***

9655 Woods Drive Unit #2004, Skokie

$380,000
2 Beds 2 Baths 12041417 MLS CLOSED Status Madison Place BLDG.
Welcome to Madison Place. This well maintained and updated building offers an inviting Lobby. Bright and open Corner Penthouse. This 1600 SQ well maintained condo offers a large Primary Suite with a walk in closet and panoramic views of the Chicago skyline. The foyer entry leads way to a front hall closet and in unit Laundry room with cabinet storage. There is a second full bathroom and a spacious second Bedroom. Open to the Kitchen and Dining Room the bright Living Room has sliding doors to the spacious balcony. The large Kitchen with wood cabinetry has room for a table. Two Parking spots side by side. #12,13 with 2 storage closets-each in front of a parking spot labeled 603. On site Engineer M-F and Saturday morning.

5055 Madison Street Unit #603, Skokie



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.