$1,599,000

beds

baths

half bath

4,491

square ft

251 Oakland Drive

Highland Park, Illinois 60035

New / MLS #12735318 / Single Family / Highland Park

Listing information updated 8/25/2026 at 6:03pm

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.

Full Features

Architecture Style:

Traditional

Exterior Type:

Brick,Cedar

Basement:

Finished,Full

Beds Above Grade:

Beds Below Grade:

Cooling System:

Central Air

Heating System:

Natural Gas

Appliances:

Range, Microwave, Dishwasher, High End Refrigerator, Washer, Dryer, Disposal, Range Hood, Gas Oven, Humidifier

Main Level Primary Bedroom:

Fireplace:

Yes

Pool:

Age:

91-100 Years

Roof Type:

Asphalt

Parking Type:

Garage - Asphalt,Garage Door Opener,Heated Garage,Yes,Garage Owned,Attached,Garage

Parking Spaces:

Garage:

Attached

Room Count:

Water Front:

Square Feet:

4,491

Lot Size:

.25-.49 Acre

Acreage:

0.252

Internal Features:

Vaulted Ceiling(s), Walk-In Closet(s), Beamed Ceilings, Separate Dining Room

External Features:

Patio/Porch

Room Information

Living Room:

25x16 - Main

Dining Room:

15x13 - Main

Kitchen:

16x14 - Main

Family Room:

22x18 - Main

Primary Bedroom:

20x15 - Second Level

2nd Bedroom:

15x11 - Second

3rd Bedroom:

15x11 - Second

4th Bedroom:

16x15 - Third

Bedroom 5:

19x12 - Basement Level

Breakfast Room:

18x15 - Main Level

Foyer:

17x8 - Main Level

Mud Room:

8x5 - Main Level

Office:

23x19 - Third Level

Taxes & Assessments

Tax Amount:

$19,746

Tax Year:

2025

Location

Zip Code:

60035

City:

Highland Park

County:

Lake

Schools

School District(s):

112, 113

Elementary School:

Braeside Elementary School

Middle School:

Edgewood Middle School

High School:

Highland Park High School

Architecture Style:

Traditional

Exterior Type:

Brick,Cedar

Basement:

Finished,Full

Beds Above Grade:

Beds Below Grade:

Cooling System:

Central Air

Heating System:

Natural Gas

Appliances:

Range, Microwave, Dishwasher, High End Refrigerator, Washer, Dryer, Disposal, Range Hood, Gas Oven, Humidifier

Main Level Primary Bedroom:

Fireplace:

Yes

Pool:

Age:

91-100 Years

Roof Type:

Asphalt

Parking Type:

Garage - Asphalt,Garage Door Opener,Heated Garage,Yes,Garage Owned,Attached,Garage

Parking Spaces:

Garage:

Attached

Room Count:

Water Front:

Square Feet:

4,491

Lot Size:

.25-.49 Acre

Acreage:

0.252

Internal Features:

Vaulted Ceiling(s), Walk-In Closet(s), Beamed Ceilings, Separate Dining Room

External Features:

Patio/Porch

Living Room:

25x16 - Main

Dining Room:

15x13 - Main

Kitchen:

16x14 - Main

Family Room:

22x18 - Main

Primary Bedroom:

20x15 - Second Level

2nd Bedroom:

15x11 - Second

3rd Bedroom:

15x11 - Second

4th Bedroom:

16x15 - Third

Bedroom 5:

19x12 - Basement Level

Breakfast Room:

18x15 - Main Level

Foyer:

17x8 - Main Level

Mud Room:

8x5 - Main Level

Office:

23x19 - Third Level

Tax Amount:

$19,746

Tax Year:

2025

Zip Code:

60035

City:

Highland Park

County:

Lake

School District(s):

112, 113

Elementary School:

Braeside Elementary School

Middle School:

Edgewood Middle School

High School:

Highland Park High School

Listing Office: @PROPERTIES

Listing Office Phone: 847.432.0700

Disclaimer: The data relating to real estate for sale on this website comes courtesy of Midwest Real Estate Data, LLC as distributed by MLS GRID. Real estate listings held by brokerage firms other than @properties are marked with the Broker Reciprocity thumbnail logo and detailed information about them includes the name of the listing brokers. Properties displayed may be listed or sold by various participants in the MLS. Based on information submitted to the MLS GRID as of 8/25/2026 at 6:03pm. 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. Some listings have been excluded from this website.

New Listings in Highland Park, IL

Recently Sold Homes in Highland Park, IL

Nearby Homes for Sale

251 Oakland Drive, Highland Park, IL 60035 is a single family home currently listed at $1,599,000. 251 Oakland Drive features 5 Beds, 4 Baths, 1 Half Bath. This single family home has been listed on @properties Christie's International Real Estate since August 25th, 2026 and was built in 1929. Nearby schools include Braeside Elementary School, Edgewood Middle School, and Highland Park High School. The nearest transit stops include Ravinia Park Metra Metra Union Pacific North line.