A rare opportunity to own a truly distinctive corner duplex penthouse in one of the city's most coveted locations.
30 pictures
Apartment
USD 4,500,000
viewed
Chicago, Cook County
TerraceLift
1 week + 2 days ago
Exquisite Duplex Penthouse at Tribune Tower Residences A Once in a Lifetime Offering: Experience the pinnacle of Chicago luxury living in the only two
18 pictures
Apartment
USD 1,395,000
viewed
Chicago, Cook County
TerraceBalconyEquipped kitchen
3 weeks + 1 day ago
Enjoy elevated luxury living in this rarely available, beautifully upgraded extra-wide duplex at The Conservatory, showcasing unobstructed views of Lake
12 pictures
House
USD 459,000
viewed
Chicago, Cook County
Equipped kitchenParking
Sep 25, 2026
This spacious and light-filled 3 bedroom/2.1 bath duplex-up showcases modern design and expert craftsmanship throughout.
4 pictures
House
USD 1,450,000
viewed
Chicago, Cook County
TerraceParking
Sep 18, 2026
George St.
20 pictures
Apartment
USD 425,000
viewed
Chicago, Cook County
DeckEquipped kitchen
3 days + 11 hours ago
exposure lets natural light shine in.
25 pictures
Apartment
USD 449,900
viewed
Chicago, Cook County
PatioFireplaceEquipped kitchenParking
3 days + 11 hours ago
THIS MOVE-IN READY 2BED/2BATH UNIT FEATURES AN OPEN CONCEPT FIRST FLOOR LIVING SPACE.
12 pictures
Apartment
USD 2,698,000
viewed
Wilmette, Cook County
PatioTerraceEquipped kitchenSwimming pool
1 week + 2 days ago
New Construction 3 Bed, 3.5 Bath Duplex Residence with an 802 SF Private Landscaped Patio!
29 pictures
Apartment
USD 1,949,000
viewed
Chicago, Cook County
PatioTerraceDeckFireplaceEquipped kitchen
2 weeks + 4 days ago
Lincoln Park new construction 4-bedroom, 3.1-bath duplex-up featuring a private rooftop deck and covered rear deck with outdoor fireplace.
32 pictures
Apartment
USD 1,599,000
viewed
Chicago, Cook County
PatioDeckFireplaceEquipped kitchenParking
2 weeks + 4 days ago
Lincoln Park new construction 4-bedroom, 3.1-bath duplex down featuring a covered rear deck with outdoor fireplace plus private garage roof deck.
39 pictures
Apartment
USD 1,450,000
viewed
Chicago, Cook County
TerraceDeckEquipped kitchenParking
3 weeks + 2 days ago
Rarely available duplex penthouse in the heart of the Southport Corridor!
20 pictures
Apartment
USD 849,000
viewed
Chicago, Cook County
GardenTerraceDeckFireplaceEquipped kitchen
3 weeks + 1 day ago
This completely and thoughtfully renovated 3 bed, 2.5 bath duplex offers an incredibly rare amount of private outdoor space, including a huge walled yard
5 pictures
Apartment
USD 1,949,000
viewed
Chicago, Cook County
Equipped kitchenParking
Oct 02, 2026
*NEW, UNDER CONSTRUCTION WITH FALL 2026 DELIVERY*PENTHOUSE DUPLEX UP! NOT YOUR COOKIE CUTTER DUPLEX!
26 pictures
Apartment
USD 760,000
USD 799,000
5%
viewed
Chicago, Cook County
TerraceDeckFireplaceEquipped kitchen
1 week + 2 days ago
This stunning two bedroom, two bath penthouse duplex loft delivers dramatic architectural character, an expansive open floor plan and two outdoor spaces
16 pictures
Apartment
USD 549,000
viewed
Chicago, Cook County
TerraceEquipped kitchenParking
1 week + 6 days ago
Huge extra wide new construction duplex ready for delivery! Biggest unit in the building at 4beds & 4 baths!
30 pictures
Apartment
USD 1,200,000
viewed
Chicago, Cook County
GardenTerraceFireplaceEquipped kitchen
2 weeks + 5 days ago
Set in one of Lincoln Park's most coveted residential pockets, this newer-construction duplex corner residence at 1205 W Montana pairs sophisticated design
16 pictures
Apartment
USD 850,000
viewed
Chicago, Cook County
GardenTerraceDeckEquipped kitchenParking
2 weeks + 6 days ago
Exceptional, extra-wide 2660 sqft - 3BR/3BA duplex in a classic 1891 Chicago greystone in the heart of East Village (redone in 2019).
18 pictures
Apartment
USD 799,000
viewed
Chicago, Cook County
PatioFireplaceEquipped kitchen
Sep 26, 2026
Beautiful duplex down, three bedroom condo in a historic East Lakeview Greystone.
32 pictures
Apartment
USD 1,039,000
viewed
Chicago, Cook County
TerraceBalconyFireplace
Sep 18, 2026
An oversized and generous, 3 bedroom 2.1 bathroom duplex penthouse - better than new construction.
27 pictures
Apartment
USD 1,985,000
viewed
Chicago, Cook County
TerraceFireplace
Sep 18, 2026
This intimate two-residence building features a spacious duplex-down thoughtfully designed to deliver sophisticated indoor-outdoor living, timeless craftsmanship
5 pictures
Apartment
USD 1,900,000
viewed
Chicago, Cook County
TerraceFireplaceEquipped kitchenParking
Sep 18, 2026
This wonderful 4 bed 3.1 bath duplex residence has an intelligent spacious floor plan - the main level encompases open concept living spaces and incredible
50 pictures
Apartment
USD 1,575,000
viewed
Evanston, Cook County
BalconyEquipped kitchenSwimming pool
Sep 18, 2026
DUPLEX PENTHOUSE DESIGNED BY AWARD-WINNING ARCHITECT DAVID HOVEY DELIVERS A DRAMATIC ARCHITECTURAL STATEMENT - DOWNTOWN CHICAGO, EVANSTON, AND LAKE MICHIGAN
30 pictures
Apartment
USD 4,995,000
viewed
Chicago, Cook County
8 Bedrooms
5,110 sq.ft
TerraceEquipped kitchen
Oct 07, 2026
Featured in Interiors Magazine, this extraordinary duplex-up penthouse is one of the largest floor plans in the building, spanning two breathtaking levels
19 pictures
Apartment
USD 1,900,000
USD 2,000,000
5%
viewed
Chicago, Cook County
TerraceDeckEquipped kitchen
Oct 03, 2026
This stunning 4-bedroom, 3.1-bathroom duplex penthouse in the heart of Lincoln Park has a thoughtfully designed floor plan, refined finishes, and exceptional
50 pictures
Apartment
USD 2,099,000
USD 2,150,000
2%
viewed
Chicago, Cook County
Deck
Sep 25, 2026
limestone building features three distinctive residences: Unit 1F: 4 bedrooms + den, 2 baths, Unit 1R: 3 bedrooms + den, 2.5 baths, Unit 2 (Penthouse Duplex
5 pictures
Apartment
USD 1,525,000
viewed
Chicago, Cook County
TerraceDeckFireplaceEquipped kitchenParking
Sep 20, 2026
This spacious 4 bed 3.1 bath duplex is set in an intimate all masonry new construction 2 unit building on a beautiful, quiet tree lined street in prime
43 pictures
House
USD 8,400,000
viewed
Chicago, Cook County
Office roomEquipped kitchen
Sep 20, 2026
Own the pinnacle of Chicago elegance in this 7880 sq ft duplex penthouse, formerly home to Vince Vaughn and the original headquarters of Hugh Hefner's
5 pictures
Apartment
USD 1,550,000
viewed
Chicago, Cook County
TerraceParking
Sep 18, 2026
George St. This incredible 3 bed 3.1 bath PENTHOUSE DUPLEX-UP home with FULLY PAVED AND BUILT OUT PRIVATE ROOF TERRACE.
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