Situated on a premier, tree-lined street in the highly coveted Blaine School District, this exceptionally rare Lakeview multi-family investment asset underwent a comprehensive, high-end rehabilitation in 2025, generating a powerhouse monthly rental income of $11,200 ($134,400 gross annually) anchored by a secure duplex lease extending into March 2028. Presenting an unrivaled turn-key opportunity for either a yield-focused portfolio investor or a live-in owner looking to substantially subsidize their mortgage, the impressive 4,264-square-foot footprint features three renovated two-bedroom residences and an owner-caliber three-bedroom, two-and-a-half-bath penthouse duplex up. The stunning, sun-drenched penthouse showcases soaring cathedral and beamed ceilings illuminated by bright skylights, a gracious living room with architectural bay windows and a gas fireplace, and a professional-grade gourmet kitchen boasting rich granite countertops, a massive prep island, and a premier Viking refrigerator alongside high-end stainless steel appliances. This crown jewel unit is completed by an expansive private roof deck perfect for entertaining, second-floor in-unit laundry, and a tranquil primary suite featuring a spa-like master bathroom with a double-bowl vanity, separate soaking tub, and a custom shower. Complementing the duplex are the three turn-key two-bedroom residences showing high-value finishes such as updated kitchens with stainless steel appliances, new individual thermostats, and pristine hardwood flooring, with the rear unit featuring a large, versatile three-season sunroom. Mechanical and structural integrity is built directly into this passive income producer, highlighted by comprehensively updated electrical wiring, an optimized heating system with freshly insulated lines, and fully flushed radiators for effortless seasonal climate control. Finished with a dry, spacious basement providing dedicated resident storage lockers, new common laundry, and a detached two-car garage with a newly replaced door, this magnificent building sits just steps from the boutique shopping and dining of the Southport Corridor, public transit, and the vibrant local energy of Wrigleyville.
Listing Courtesy of Midwest Real Estate Data as distributed by MLS GRID / Listed By: Brett Bucholz, Coldwell Banker Realty
$650,000 (USD)
Chicago Area Condominium
Active
111 E Chestnut Street 30C Chicago, IL 60611
2 Bed
2 Baths
1425 sqft
MLS# 12557523
Spectacular 30th-floor vistas of Lake Michigan sunrises and the city's iconic landmarks define this expansive 1,425 sq. ft. Gold Coast retreat, currently undergoing a sophisticated, bright design refresh. This premier corner residence features 16 dramatic floor-to-ceiling windows showcasing panoramic views of the historic Water Tower and the illuminated Palmolive Building. Currently in progress but fully viewable for showings, the home is being transformed with newly lightened solid oak floors and a fresh, bright custom paint palette that maximizes the abundant natural light throughout. The versatile layout begins with a grand foyer and elegant French doors leading to a king-sized second bedroom or executive office, opening into an expansive living and dining area perfect for entertaining. The kitchen is outfitted with sleek black granite counters and stainless steel appliances, while long-term peace of mind is guaranteed by four recently updated Zoneline GE HVAC units. Modern conveniences abound, including an in-unit laundry closet, an included storage locker, high-speed mesh Wi-Fi, and a premium cable package. Located in a full-service building with 24-hour door staff, a fitness center, and a heated outdoor pool, this home is positioned just steps from Michigan Avenue and Oak Street Beach-representing an exceptional opportunity to secure a refreshed, high-floor luxury footprint.
Listing Courtesy of Midwest Real Estate Data as distributed by MLS GRID / Listed By: Brett Bucholz, Coldwell Banker Realty
$425,000 (USD)
Chicago Area Condominium
Active
111 E Chestnut Street 40J Chicago, IL 60611
2 Bed
1 Baths
1000 sqft
MLS# 12642970
A rare 40th-floor find in the heart of the Gold Coast, Unit 40J delivers a turnkey, two-bedroom floor plan complete with the building's most coveted upgrade: a private in-unit washer and dryer. This reimagined residence features a comprehensive refresh, highlighted by a chef-inspired kitchen with brand-new white quartz countertops and a deep undermount sink. The primary bathroom has been equally modernized with a new dual-sink quartz vanity. Expansive hardwood floors unify the home, extending from the entry foyer through the living and dining areas and into the newly added second bedroom. High-impact western exposure provides exceptional natural light and sunset vistas over Connors Park through eight floor-to-ceiling windows. This is an investor-friendly building known for its robust annual social calendar and updated amenities, including a fitness center, heated outdoor pool, and two professional-grade grilling decks. Monthly assessments offer a simplified lifestyle, covering high-speed WiFi and a premium TiVo DVR cable package, with the owner responsible only for electric. Positioned just steps from the Magnificent Mile and Oak Street Beach, this residence offers both immediate luxury and long-term investment potential.
Listing Courtesy of Midwest Real Estate Data as distributed by MLS GRID / Listed By: Brett Bucholz, Coldwell Banker Realty
$415,000 (USD)
Chicago Area Condominium
Active
111 E Chestnut Street 55D Chicago, IL 60611
1 Bed
1 Baths
1000 sqft
MLS# 12664800
A must-see in person, this beautifully updated 1,000 sq ft one-bedroom on the 55th floor offers incredible western views over Connors Park through eight floor-to-ceiling windows-ideal for sunset and nighttime cityscapes. The space shows even better in person with fresh paint throughout, brand-new hardwood floors in the living room and bedroom, and newly installed roller shades-blackout in the bedroom and light-filtering in the living area. The open kitchen features granite countertops and stainless steel appliances, while the elegant marble bathroom includes dual sinks and a Jacuzzi tub/shower. A separate dining area offers flexibility for use as a den or office. Additional highlights include a decorative marble foyer, in-unit laundry, and generous closet space. Full-service building amenities include 24-hour door staff, outdoor heated pool, fitness center, two BBQ decks, party and conference rooms, and on-site valet dry cleaning. Rent includes 500mb high-speed WiFi and TiVo DVR with premium movie channels through the building's bulk cable/internet package.
Listing Courtesy of Midwest Real Estate Data as distributed by MLS GRID / Listed By: Brett Bucholz, Coldwell Banker Realty
$400,000 (USD)
Chicago Area Condominium
Active
111 E Chestnut Street 31J Chicago, IL 60611
1 Bed
1 Baths
1000 sqft
MLS# 12643392
vailable for possession by month-end, this high-floor 31st-floor J tier residence presents a premier opportunity for both investors and homeowners in the heart of the Gold Coast. Offering a compelling buy vs. rent case, this spacious 1,000 sq. ft. home is located in a highly sought-after, investor-friendly building with no history of special assessments. The residence is defined by sophisticated marble flooring that spans the entry foyer, kitchen, and the expansive living and dining areas. Eight floor-to-ceiling windows frame unobstructed western vistas of Connors Park and the city's iconic sunset skyline. The galley kitchen features recently updated appliances, while the primary bedroom serves as a quiet sanctuary with light-toned wood luxury vinyl flooring. A stone-top vanity anchors the bathroom, complementing the home's refined materiality and pristine maintenance. Residents enjoy a full-amenity lifestyle with 24-hour door staff, a fitness center, an outdoor heated pool, dual BBQ decks, and a robust annual social calendar. Monthly assessments cover high-speed WiFi and a premium TiVo DVR cable package, with the owner responsible only for electric. Positioned just steps from the Magnificent Mile and Oak Street Beach, this residence is perfectly prepared for its next chapter.
Listing Courtesy of Midwest Real Estate Data as distributed by MLS GRID / Listed By: Brett Bucholz, Coldwell Banker Realty
$225,000 (USD)
Chicago Area Condominium
Active
474 N Lake Shore Drive 4607 Chicago, IL 60611
0 Bed
1 Baths
642 sqft
MLS# 12438829
Enjoy open west-facing city views from this spacious 642 sqft studio on the 46th floor of 474 N Lake Shore Drive. Recently updated with new hardwood flooring and fresh paint, this high-floor home is filled with natural light from large picture windows and offers a flexible layout for living, working, and relaxing in the heart of Streeterville. The kitchen features granite countertops, maple cabinetry, and GE appliances, along with the convenience of an in-unit washer and dryer. Building amenities include 24-hour door staff, on-site fitness center, indoor pool, expansive sundeck with stainless steel grills and seating areas, and professional management. Assessments include cable and internet. Just steps from the lakefront path, Navy Pier, Northwestern, Michigan Avenue shopping, Target, Whole Foods, and some of Chicago's best dining and entertainment.
Listing Courtesy of Midwest Real Estate Data as distributed by MLS GRID / Listed By: Brett Bucholz, Coldwell Banker Realty
$3,250 / mo (USD)
Chicago Area Rental Home
Active
111 E Chestnut Street 31J Chicago, IL 60611
1 Bed
1 Baths
1000 sqft
MLS# 12643403
Available for a June 1st move-in, this high-floor 31st-floor J tier residence offers an expansive 1,000 sq. ft. floor plan in the heart of the Gold Coast. This true one-bedroom home features a simplified living experience where the rent includes high-speed WiFi, a premium TiVo DVR cable package, and water. Tenants are responsible only for electric, which provides full individual control over the PTAC heating and cooling units-a major benefit during shoulder seasons allowing for A/C during the day and heat at night as needed. The residence is defined by sophisticated marble flooring throughout the entry foyer, kitchen, and the oversized living area, which offers plenty of room for a dedicated professional desk setup. Eight floor-to-ceiling windows frame unobstructed western vistas of Connors Park and the city's iconic sunset skyline. The primary bedroom serves as a quiet sanctuary with light-toned wood luxury vinyl flooring. Please note that kitchen photos are from a prior shoot and may not reflect all current appliances (including the stove). Residents enjoy a full-amenity lifestyle with 24-hour door staff, a fitness center, an outdoor heated pool, and dual BBQ decks. Steps from the Magnificent Mile and Oak Street Beach, this is the perfect urban sanctuary.
Listing Courtesy of Midwest Real Estate Data as distributed by MLS GRID / Listed By: Brett Bucholz, Coldwell Banker Realty
$3,200 / mo (USD)
Chicago Area Rental Home
Active
111 E Chestnut Street 39J Chicago, IL 60611
1 Bed
1 Baths
1000 sqft
MLS# 12660117
Professional photos coming later this week. 1000 sq ft large 1 BR with 8 floor to ceiling windows & great Sunset views. This home overlooks Landmarked Quigley seminary, Connors Park & City Skyscrapers. Hardwood floors in LR & DR. Bedroom is not pictured because it hsas new luxury vinyl floors. Marble entry foyer, kit & bath floors with granite counters. Lots of closets + storage locker on same floor. W/D in unit. Full service building with 24Hr Door Person, Heated Pool, Fitness Center, conference room, Dry Cleaners, Party room w full kitchen and bar & 2 BBQ decks with 10 grills. Great Location. Non-Smoking building.
Listing Courtesy of Midwest Real Estate Data as distributed by MLS GRID / Listed By: Brett Bucholz, Coldwell Banker Realty