251 Oakland Dr Highland Park, IL 60035
251 Oakland Dr Highland Park, IL 60035 | MLS 12735318 Photo 1
251 Oakland Dr Highland Park, IL 60035 | MLS 12735318 Photo 2
251 Oakland Dr Highland Park, IL 60035 | MLS 12735318 Photo 3
251 Oakland Dr Highland Park, IL 60035 | MLS 12735318 Photo 4
251 Oakland Dr Highland Park, IL 60035 | MLS 12735318 Photo 5
For more information on this listing, contact us at: (773) 998-2401
Active
$1,599,000

251 Oakland Dr Highland Park, IL 60035

Detached Single Property Type
4 Beds
4 Full 1 Half Baths
4,491 Sq. Ft.
1929 Year Built
Lake County
View All Property Details
Exceptional location between Braeside and Ravinia! Don't be fooled from the outside-this meticulously maintained home offers nearly 4,500 square feet of beautifully designed living space filled with timeless character. A major 2001 renovation reconfigured the first floor while updating the electrical and plumbing, installing Marvin windows, attaching the 2-car garage, and adding a stunning conservatory. Rich millwork, classic paneling, and three brick fireplaces add warmth and charm throughout. The spacious living room, family room, and conservatory provide outstanding spaces for entertaining and everyday living. The flexible floor plan features 5 bedrooms, including one in the finished basement. The second floor offers a spacious primary suite, two additional bedrooms, and a full bath, while the third floor includes another bedroom, bonus room, and full bath. The finished basement boasts a large recreation room, bedroom/office or exercise room, full bath, laundry with kitchenette, and abundant storage. New roof installed last year. and exterior painted this year. Enjoy the beautiful yard with mature trees and two inviting patios. Ideally located near Rosewood Beach, Ravinia Festival, the Ravinia Business District, North Shore Trail, Braeside School, and the Metra station.
MLS # 12735318
Monthly HOA N/A
On Site 25 Days
Last Updated 8/31/2026

Location

Contact Agent

Property Rocks

Property Rocks

(773) 998-2401

Property Details

Community Information

Address 251 Oakland Dr, Highland Park, IL 60035
County Lake
Township Moraine
Zip Code 60035

School Information

School District 112
Middle School Edgewood Middle School
Elementary School Braeside Elementary School

Architecture

Bedrooms 4
Bathrooms 4 Full / 1 Half
Year Built 1929
Style Traditional
Construction Materials Brick, Cedar
Age Range 91-100 Years
Type Detached 3 Stories
Roof Asphalt
Foundation Concrete Perimeter
Basement Type Finished, Full
Parking Features Asphalt, Garage Door Opener, Heated Garage, Yes, Garage Owned, Attached, Garage

Features / Amenities

Interior Features Vaulted Ceiling(s), Walk-In Closet(s), Beamed Ceilings, Separate Dining Room
Appliances Range, Microwave, Dishwasher, High End Refrigerator, Washer, Dryer, Disposal, Range Hood, Gas Oven, Humidifier
Equipment Security System, CO Detectors, Ceiling Fan(s), Sump Pump, Sprinkler-Lawn, Water Heater-Gas
Fireplace Features Wood Burning, Gas Log
Fireplaces Total 2
Flooring Hardwood
Laundry Gas Dryer Hookup, Sink
Rooms Bedroom 5, Breakfast Room, Foyer, Mud Room, Office, Recreation Room, Storage, Walk In Closet
Patio And Porch Patio
Window Skylight(s)
Parking Total 2
Garage Spaces 2
Air Conditioning Central Air
Heat Source / Type Natural Gas
Fireplace(s) Family Room, Living Room
Total Rooms 12

Property Features

Lot Size 0.25 Acres
Lot Dimensions .25-.49 Acre
Lot Features Corner Lot, Mature Trees
Sewer Public Sewer
Water Lake Michigan
Electric 200+ Amp Service
Transportation School Bus Service, Commuter Train
Open House Count 0
Directions Sheridan Rd north of Lake Cook and South of Roger Williams to Oakland , West to 2nd house on north side of street

Tax and Financial Info

Tax Year 2025
Tax Annual Amount $19,746
Ownership Fee Simple

Rooms

Level
Bedroom 5Basement
Recreation RoomBasement
StorageBasement
LaundryBasement
Breakfast RoomMain
FoyerMain
Mud RoomMain
Dining RoomMain
Family RoomMain
KitchenMain
Living RoomMain
N/A
N/A
Walk In ClosetSecond
Bedroom 2Second
Bedroom 3Second
Master BedroomSecond
OfficeThird
Bedroom 4Third

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251 Oakland Dr Highland Park, IL 60035 | MLS 12735318
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Listing provided courtesy of @Properties Christie's International Real Estate.

Listings courtesy of MRED MLS as distributed by MLS GRID

Based on information submitted to the MLS GRID as of September 18, 2026 1:15 PM CST. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Properties displayed may be listed or sold by various participants in the MLS

(773) 998-2401
251 Oakland Dr Highland Park, IL 60035
  • $1,599,000
  • 4 beds
  • 4 full  1 half baths
  • 4,491 Sq. Ft.