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
39 pictures
Apartment
USD 1,450,000
viewed
Chicago, Cook County
TerraceDeckEquipped kitchenParking
1 week + 3 days ago
Rarely available duplex penthouse in the heart of the Southport Corridor!
5 pictures
Apartment
USD 1,949,000
viewed
Chicago, Cook County
Equipped kitchenParking
2 weeks + 4 days ago
*NEW, UNDER CONSTRUCTION WITH FALL 2026 DELIVERY*PENTHOUSE DUPLEX UP! NOT YOUR COOKIE CUTTER DUPLEX!
20 pictures
Apartment
USD 425,000
viewed
Chicago, Cook County
DeckEquipped kitchen
3 weeks + 2 hours ago
exposure lets natural light shine in.
27 pictures
Apartment
USD 575,000
viewed
Chicago, Cook County
TerraceDeckFireplaceEquipped kitchenParking
3 weeks + 1 day ago
In the heart of Bucktown, this professionally designed and beautifully renovated 2-bedroom plus den, 2-bath corner duplex timber loft offers a rare combination
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Updated
Foreclosure
House
Request Details
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Donnellson, Montgomery County
3 Bedrooms
1 Bathroom
1,176 sq.ft
1 day + 2 hours ago
Therefore, there could be an opportunity to strike a great deal with the owner and the bank
16 pictures
Apartment
USD 850,000
viewed
Chicago, Cook County
GardenTerraceDeckEquipped kitchenParking
1 week + 2 hours ago
Exceptional, extra-wide 2660 sqft - 3BR/3BA duplex in a classic 1891 Chicago greystone in the heart of East Village (redone in 2019).
16 pictures
Apartment
USD 549,000
viewed
Chicago, Cook County
Equipped kitchenParking
Sep 25, 2026
Huge extra wide new construction duplex ready for delivery! Biggest unit in the building at 4beds & 4 baths!
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
25 pictures
House
USD 675,000
viewed
Chicago, Cook County
BalconyFireplaceEquipped kitchen
Sep 18, 2026
Perched on the top floor of an intimate six-unit building, this three-bedroom, two-bath duplex penthouse lives large, with soaring vaulted ceilings, hardwood
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
9 pictures
Apartment
USD 1,595,000
viewed
Chicago, Cook County
9 Bedrooms
Equipped kitchen
Sep 10, 2026
Discover refined city living in these new construction duplex residences by BAK HOME Development, ideally positioned on prestigious Lakewood Avenue in
30 pictures
Apartment
USD 1,200,000
viewed
Chicago, Cook County
GardenTerraceFireplaceEquipped kitchen
6 days + 2 hours 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
30 pictures
Apartment
USD 4,995,000
viewed
Chicago, Cook County
8 Bedrooms
5,110 sq.ft
TerraceEquipped kitchen
1 week + 6 days ago
Featured in Interiors Magazine, this extraordinary duplex-up penthouse is one of the largest floor plans in the building, spanning two breathtaking levels
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.
26 pictures
Apartment
USD 799,000
viewed
Chicago, Cook County
TerraceDeckFireplaceEquipped kitchen
Sep 18, 2026
This stunning two bedroom, two bath penthouse duplex loft delivers dramatic architectural character, an expansive open floor plan and two outdoor spaces
25 pictures
Apartment
USD 645,000
viewed
Chicago, Cook County
Equipped kitchen
Sep 18, 2026
A rare opportunity to own a truly distinctive corner duplex penthouse in one of the city's most coveted locations.
19 pictures
Apartment
USD 1,900,000
USD 2,000,000
5%
viewed
Chicago, Cook County
TerraceDeckEquipped kitchen
2 weeks + 3 days ago
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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House
USD 635,000
viewed
Chicago, Cook County
3 Bedrooms
PatioOffice roomFireplaceEquipped kitchen
4 days + 2 hours ago
Experience this updated 3-bedroom, 2.5-bath duplex-down in West TownWicker Park, featuring multiple outdoor spaces and thoughtful renovations throughout
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House
USD 635,000
viewed
Chicago, Cook County
3 Bedrooms
2 Bathrooms
PatioOffice roomFireplaceEquipped kitchen
4 days + 2 hours ago
Experience this updated 3-bedroom, 2.5-bath duplex-down in West TownWicker Park, featuring multiple outdoor spaces and thoughtful renovations throughout
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Apartment
Request Details
viewed
Chicago, Cook County
2 Bedrooms
Equipped kitchenParking
4 days + 2 hours ago
This duplex home includes a fresh kitchen renovation, new flooring in kitchen, new lighting and fresh paint.
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Apartment
Request Details
viewed
Chicago, Cook County
2 Bedrooms
2 Bathrooms
Equipped kitchenParking
4 days + 2 hours ago
This duplex home includes a fresh kitchen renovation, new flooring in kitchen, new lighting and fresh paint.
