$1,599,000

251 Oakland Drive, Highland Park, IL 60035

Active
4 beds (5 possible) 4.5 baths 4,491 sqft (plans) Built 1929 Residential MLS #MRD12735318 1 days on market
Listing courtesy of @properties Christie's International Real Estate · 847-432-0700 · MLS #MRD12735318 · Status: Active
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.

Property details

Interior

Appliances
Range, Microwave, Dishwasher, High End Refrigerator, Washer, Dryer, Disposal, Range Hood, Gas Oven, Humidifier
Interior features
Vaulted Ceiling(s), Walk-In Closet(s), Beamed Ceilings, Separate Dining Room
Flooring
Hardwood
Fireplaces
2
Fireplace details
Wood Burning, Gas Log
Basement
Finished, Full
Laundry
Gas Dryer Hookup, Sink
Additional rooms
Bedroom 5, Breakfast Room, Foyer, Mud Room, Office, Recreation Room, Storage, Walk In Closet
Total rooms
12

Building & exterior

Style
Traditional
Age
91-100 Years
Exterior
Brick, Cedar
Roof
Asphalt
Foundation
Concrete Perimeter
Windows
Skylight(s)
Patio & porch
Patio
Other structures
None

Parking

Garage spaces
2
Total spaces
2
Parking details
Asphalt, Garage Door Opener, Heated Garage, Yes, Garage Owned, Attached, Garage

Lot & location

Lot dimensions
112x100
Lot description
Corner Lot, Mature Trees
Township
Moraine
County
Lake

Utilities

Heating
Natural Gas
Cooling
Central Air
Water
Lake Michigan
Sewer
Public Sewer
Electricity
200+ Amp Service
Equipment
Security System, CO Detectors, Ceiling Fan(s), Sump Pump, Sprinkler-Lawn, Water Heater-Gas

HOA & community

Assessment includes
None
Community features
Street Lights, Street Paved

Schools

Elementary
Braeside Elementary School (112)
Junior high
Edgewood Middle School (112)
High school
Highland Park High School (113)

Taxes & terms

Annual taxes
$19,746 (2025)
Parcel number (PIN)
16362090040000
PIN
16362090040000
Ownership
Fee Simple
Possession
Closing
Special conditions
None
Listed
8/25/2026

Rooms

RoomSizeLevelFlooring
Bedroom 519X12BasementCarpet
Breakfast Room18X15MainStone
Foyer17X8MainHardwood
Mud Room8X5MainStone
Office23X19ThirdCarpet
Recreation Room25X23BasementCarpet
Storage17X14BasementCarpet
Walk In Closet11X6SecondHardwood
Bedroom 215X11SecondHardwood
Bedroom 315X11SecondHardwood
Bedroom 416X15ThirdCarpet
Dining Room15X13MainWood Laminate
Family Room22X18MainHardwood
Kitchen16X14MainHardwood
Laundry11X8BasementCeramic Tile
Living Room25X16MainHardwood
Master Bedroom20X15SecondHardwood

What would this home cost per month?

Using this listing's actual tax bill (2025) — adjust anything.

Rates move daily — edit to today's quote. Under 20% down adds PMI automatically.

Estimated monthly payment
$0
Principal & interest
Property taxes
Insurance
PMI (under 20% down)
HOA / assessments

Estimates only — not a loan offer or quote; your rate, insurance and PMI depend on your credit and lender. Run other scenarios on the full mortgage calculator, or ask us to connect you with lenders our clients actually close with.

Recently sold nearby

AddressBeds / BathsSoldPrice
550 Sheridan Road 4 bd / 3.5 ba Apr 2026 $1,150,000
520 Sheridan Road 4 bd / 4 ba May 2026 $1,200,000
200 Braeburn Road 5 bd / 4.5 ba Jun 2026 $950,000
219 Woodland Road 3 bd / 3.5 ba May 2026 $600,000

Sold data courtesy of MRED as distributed by MLS GRID; properties may be listed or sold by various participants in the MLS.

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Listings courtesy of MRED as distributed by MLS GRID. MLS GRID

Based on information submitted to the MLS GRID as of 2026-08-26 14:56:05. 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.

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