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$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

$599,900
3 Beds 2 Baths 12484835 MLS CLOSED Status
Spacious, updated condo in the heart of Uptown near the Argyle commercial corridor and Aragon Ballroom entertainment district. This top-floor residence features 3 large bedrooms, 2 fully renovated bathrooms, and a flexible floor plan with a separate dining room and living room. The oversized living room can easily be used as a 4th bedroom, office, guest suite, or den, offering versatility for a variety of living needs. The renovated kitchen is equipped with premium Viking stainless steel appliances, ample cabinetry, and solid counter space-ideal for both everyday cooking and entertaining. Both bathrooms have been modernized with quality fixtures and finishes. All bedrooms provide generous proportions suitable for large furnishings, workspace setups, or additional storage needs. A rare highlight of the home is the private rooftop-level patio with city views, perfect for outdoor dining, container gardening, or relaxing. The unit also includes one gated, reserved parking space, a valuable convenience in this location. The building offers extra private storage and dedicated bike storage in the basement, adding functionality for residents who need space for seasonal items, recreational equipment, or gear. Located near the Argyle and Lawrence CTA Red Line stations, multiple bus routes, Montrose Beach, Foster Beach, the Lakefront Trail, and the Uptown entertainment district, this home provides exceptional transit access, walkability, and proximity to restaurants, cafes, retail, nightlife, and parks. Nearby neighborhoods such as Andersonville, Edgewater, Lakeview, and Ravenswood offer additional dining, shopping, and commuting options. With strong housing demand and continued neighborhood investment, this property appeals to those seeking urban convenience, rental potential, architectural charm, and long-term value. The building's historic character paired with modern upgrades presents a unique alternative to newer construction while maintaining manageability in monthly expenses. Flexible layout supports live-work configurations, shared living, or income-producing possibilities.

4834 N Kenmore Avenue Unit #3N, Chicago

$430,000
2 Beds 2 Baths 12155584 MLS CLOSED Status
Beautiful, extra-wide 2 bedroom, 2 bath, South West corner unit with heated garage parking in Uptown boutique, elevator building! Located on tree-lined Kenmore, this home enjoys a spacious floor plan and stunning 5-year new kitchen: stylish cabinetry, quartz counters, stainless steel appliances & bold backsplash, with breakfast bar that has seating for 4. The great room has a wood-burning fireplace with gas start (perfect for those cozy fall nights), room for dining table, and steps out to a large balcony (the first of 2). This is a great space for entertaining or daily life. The primary suite enjoys large, professionally organized walk-in closet and private bath featuring dual sinks and large jetted tub, plus this room shares access to your second, private outdoor space. Huge guest bedroom with another walk-in closet, and guest bath with stand-up shower. Inviting (open) front closet with bench and storage as you enter the home, plus walnut stained hardwood floors throughout, central air/heat and in-unit laundry. 1 indoor, garage parking (with additional storage area) included in the price. Great location near CTA Red Line, express buses, Target, Aragon and Riviera Theaters, dining (Demera, Lucy's, Fat Cat), nightlife (Green Mill), and conveniently located near Lake Shore Drive and lakefront path, Argyle dining and Andersonville's Clark Street shopping & entertainment district. Come home!

4704 N Kenmore Avenue Unit #3C, Chicago

$515,000
2 Beds 3 Baths 12101276 MLS CLOSED Status
DRAMATIC AND STUNNING duplex-up penthouse with City views in prime Uptown neighborhood is PERFECT for entertaining. This 2-bedroom, 3-bath home with parking included is larger than most 2-bedroom homes in the neighborhood, approx. 2,130 sq. ft. with two living rooms! First floor living room with custom painting detail leads to a beautiful open kitchen/dining area with 42" white cabinetry, stainless steel appliances, custom backsplash, granite counters, and a tall island perfect for bar stools. Spacious first floor bedroom with an en-suite bath. The second floor is a designer showplace with a classic martini wet bar with storage, a second living room with oversized picture windows/flooded with natural light, custom wall treatments, and leads to a private oasis/outdoor terrace with spectacular City views! Second floor primary suite with new custom closets, spa like bathroom w/oversized jetted tub, double sinks and modern mirror/finishes. Enjoy your private terrace with covered roof or relax to the large common roof deck, just steps away from this unit! The proximity of the common roof deck makes this roof top feel exclusive to this home. The monthly assessments include cable tv, high-speed internet, common insurance and water. Extra "optional" storage right outside the unit front door is available for $20/month from the association. Close to the CTA-Wilson stop, restaurants, nightlife, shopping, grocery stores, coffee shops, entertainment, and the lakefront. This is a "MUST-SEE" home, perfect for entertaining, located in the heart of The Uptown Theatre District, multiple venues are blocks away.

1116 W Leland Avenue Unit #3A, Chicago

$185,000
1 Beds 1 Baths 11845609 MLS CLOSED Status
Welcome to this recently updated charming vintage condo located in the vibrant Chicago Uptown Theatre neighborhood. Nestled on the peaceful, tree-lined Magnolia Ave. This elevated first-floor condo features a fantastic layout, boasting a sizable main living space lined with large windows that flood the area with an abundance of natural light. The kitchen has been tastefully remodeled with brand-new stainless steel appliances and new butcher block-style countertops. The primary bedroom is generously sized. and there's ample space for a dining table in the living room. The condo is set back on the property allowing you to enjoy the natural surroundings of trees. Other notable features include in-unit laundry, new luxury vinyl floors throughout, and the comfort of central air and heat. For your convenience, there is a large storage room in the basement and a designated bike area. The building is well-managed, with a proactive association and professional property management ensuring everything runs smoothly. Commuters will appreciate the convenience of nearby public transportation options, including the CTA Red Line and Metra Ravenswood stop, as well as the proximity to Dusable Lakeshore Drive. Street and rental parking options are also available in the area. This condo offers an incredible location for city living, just steps away from the shopping, dining, nightlife, and activities of the Uptown Entertainment District, Andersonville, and Montrose Beach. Embrace the character and convenience of this wonderful home in the heart of Chicago's lively Uptown Theatre neighborhood. No pet restrictions for your furry ones. Nearby parking is available for rent and/or purchase.

4836 N Magnolia Avenue Unit #1B, Chicago

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Uptown, Chicago IL · Curated MLS Search

Homes with Nightlife Neighborhoods in Uptown, Chicago IL

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

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