3414 N Oakley Avenue
Chicago, IL, 60618
$1,500,000
4 Beds
4 Baths
3,260 SqFt
0 Acres
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$1,500,000
3414 N Oakley Avenue
Chicago, IL, 60618
MLS #MRD12734355 image #0MLS #MRD12734355 image #1MLS #MRD12734355 image #2MLS #MRD12734355 image #3MLS #MRD12734355 image #4MLS #MRD12734355 image #5MLS #MRD12734355 image #6MLS #MRD12734355 image #7MLS #MRD12734355 image #8MLS #MRD12734355 image #9MLS #MRD12734355 image #10MLS #MRD12734355 image #11MLS #MRD12734355 image #12MLS #MRD12734355 image #13MLS #MRD12734355 image #14MLS #MRD12734355 image #15MLS #MRD12734355 image #16MLS #MRD12734355 image #17MLS #MRD12734355 image #18MLS #MRD12734355 image #19MLS #MRD12734355 image #20MLS #MRD12734355 image #21MLS #MRD12734355 image #22MLS #MRD12734355 image #23MLS #MRD12734355 image #24MLS #MRD12734355 image #25MLS #MRD12734355 image #26MLS #MRD12734355 image #27MLS #MRD12734355 image #28MLS #MRD12734355 image #29MLS #MRD12734355 image #30MLS #MRD12734355 image #31MLS #MRD12734355 image #32MLS #MRD12734355 image #33MLS #MRD12734355 image #34MLS #MRD12734355 image #35MLS #MRD12734355 image #36MLS #MRD12734355 image #37MLS #MRD12734355 image #38MLS #MRD12734355 image #39MLS #MRD12734355 image #40MLS #MRD12734355 image #41MLS #MRD12734355 image #42MLS #MRD12734355 image #43MLS #MRD12734355 image #44MLS #MRD12734355 image #45
A rare offering in the heart of Roscoe Village, this distinguished four-bedroom, three-and-a-half-bath residence combines dramatic architectural scale, exceptional storage, and beautifully designed indoor-outdoor living. Recently refreshed from top to bottom, the home features newly refinished hardwood floors, freshly painted interiors, refinished kitchen cabinetry, and substantial improvements to its roof, mechanical systems, landscaping, and exterior spaces. The main level makes an unforgettable impression with a soaring two-story dining room designed for memorable gatherings. A gracious living room and expansive family room-each anchored by a gas fireplace-offer distinct spaces for entertaining and relaxing. At the center of the home, the chef’s kitchen is richly appointed with granite countertops, double ovens, refinished cabinetry, and a premier suite of stainless steel appliances, including a Viking range. An elegant butler’s pantry completes the entertaining experience with a wet bar, wine rack, and beverage refrigerator. The family room opens directly to a generous backyard with both a brick-paver patio and lawn, complemented by refreshed landscaping, new patio stairs, and a new wrought-iron fence. Above, the resurfaced roof deck provides a peaceful private retreat with a wonderful sense of openness-perfect for morning coffee, sunset cocktails, or quiet evenings outdoors. All four bedrooms are privately arranged across the upper levels and enhanced by fully built-out California Closets. The light-filled primary suite is exceptionally spacious, offering three large walk-in closets and a luxurious travertine bath with a steam shower. The second and third bedrooms are also generously proportioned and enjoy pleasant views over the tree-lined street. Additional closets in the foyer and extensive third-floor storage beneath the eaves ensure every inch of the home is as functional as it is beautiful. A heated 2.5-car garage elevates the offering further, complete with double glass doors opening to the yard and a rare heated bonus room above-ideal for a private office, studio, fitness room, or lounge. Significant recent investments include a new main-house roof, updated roof deck, refinished hardwood floors, refreshed landscaping, newer radiant-heat boiler, updated furnaces and air-conditioning systems, and a newer washer and dryer. The location is equally exceptional, with the shops, restaurants, and cafes of Roscoe Village just outside the door. Audubon Elementary, Bell Elementary, multiple parks, Mariano’s, and everyday conveniences are all nearby, along with neighborhood favorites including Le Sud, Volo, and Turquoise. Convenient Brown Line access and nearby bus routes complete an effortlessly connected city lifestyle.

Property Details

Price:
$1,500,000
MLS #:
MRD12734355
Status:
Active
Beds:
4
Baths:
4
Type:
Single Family
Neighborhood:
chinorthcenter
Listed Date:
Sep 21, 2026
Finished Sq Ft:
3,260
Year Built:
1897
TraditionalChi – North CenterChinorthcenterAudubon Elementary SchoolAudubon Elementary SchoolLake View High School

Schools

School District:
299
Elementary School:
Audubon Elementary School
Middle School:
Audubon Elementary School
High School:
Lake View High School

Interior

Appliances
Double Oven, Range, Microwave, Dishwasher, High End Refrigerator, Bar Fridge, Disposal, Stainless Steel Appliance(s), Wine Refrigerator
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Fireplaces Total
2
Heating
Natural Gas, Forced Air, Radiant
Interior Features
Cathedral Ceiling(s), Wet Bar

Exterior

Architectural Style
Traditional
Community Features
Gated, Sidewalks, Street Lights, Street Paved
Construction Materials
Aluminum Siding, Brick
Garage Spaces
2.5
Parking Features
Garage Door Opener, Heated Garage, Yes, Garage Owned, Detached, Garage
Parking Spots
25
Parking Total
2.5
Window Features
Skylight(s)

Financial

HOA Fee Frequency
Not Applicable
HOA Includes
None
Tax Year
2025
Taxes
$17,076
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Debra Dobbs is one of Chicago’s top realtors with more than 41 years in the real estate business.

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Current real estate data for Single Family in Chicago as of Sep 22, 2026
2,492
Single Family Listed
76
Avg DOM
242
Avg $ / SqFt
$547,798
Avg List Price

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Property Summary

    3414 N Oakley Avenue Chicago IL is a Single Family for sale in Chicago, IL, 60618. It is listed for $1,500,000 and features 4 beds, 4 baths, and has approximately 3,260 square feet of living space, and was originally constructed in 1897. The current price per square foot is $460. The average price per square foot for Single Family listings in Chicago is $242. The average listing price for Single Family in Chicago is $547,798. To schedule a showing of MLS#mrd12734355 at 3414 N Oakley Avenue in Chicago, IL, contact your Compass | Debra Dobbs | The Dobbs Group agent at 3123074909.
3414 N Oakley Avenue
Chicago, IL