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.
Single-familyProperty Type
1929Year Built
0.25 acresLot Size
$356Price/Sq.Ft.
2 car garageParking
Listed by Ted Pickus• @properties Christie's International Real Estate
Listed by Lisa Schulkin• @properties Christie's International Real Estate
Ravinia, located between Lake Michigan and Skokie Valley Road, is a residential and cultural Highland Park neighborhood with a leafy street grid and a storied music campus. The neighborhood’s character concentrates at the Ravinia Festival grounds along Roger Williams Avenue, where picnic lawns, concertgoers, and the Metra platform set a lively, seasonal rhythm. Ravinia Festival anchors the calendar, while the Ravinia District’s small storefronts and patios keep the streetscape active between shows. Housing leans to early-20th-century cottages and larger homes shaded by mature trees. Green space and lake breezes shape daily routines, with walking routes threading toward the shoreline. Metra service at Ravinia Park Station ties the area to downtown Chicago without changing the quiet residential feel.
Provided by Walk Score and Local Logic
Offer insights
251 Oakland Dr · $1,599,000
$1.62M and above
75% chance or better to win
Why $1.62M+ is a strong offer
DAYS ON MARKET
18 days
The average home goes pending in 53 days.
SALE-TO-LIST
100.3%
Most homes are selling 0% above list price.
About offer insights
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Living
Dining
Interior features
Walk-in closets
Beamed ceilings
Separate dining room
Skylights
Finished attic with interior stair
Finished full basement
Two fireplaces (family room and living room) with wood burning and gas log options
Security system
CO detectors
Ceiling fans
Humidifier
Sump pump
Lawn sprinkler system
Gas water heater
Bedrooms
4 bedrooms (plus one possible 5th bedroom)
One bedroom located below grade (basement)
Master bedroom on second floor
Bathrooms
4 full bathrooms
1 half bathroom
Whirlpool tub
Basement bathroom(s) present
Kitchen
Island kitchen
Range
Gas oven
Microwave
Dishwasher
High-end refrigerator
Range hood
Disposal
Laundry & utility
Basement laundry room with gas dryer hookup and utility sink
Washer and dryer included
Flooring
Hardwood flooring throughout main living areas
Wood laminate in dining room
Stone flooring in breakfast room and mud room
Ceramic tile in basement laundry
Carpet in select bedrooms, recreation room and storage
Heating & cooling
Natural gas heating
Central air conditioning
Exterior features
Patio
Corner lot with mature trees
School bus service and commuter train access
Home design
Detached single-family home
3 stories
Fee simple ownership
Rehab completed in 2001
Approximate total finished area 4,491
Parking
Attached heated 2-car garage with asphalt driveway, garage door opener; garage is owned
Security
Security system
Construction
Brick and cedar exterior
Asphalt roof
Concrete perimeter foundation
Originally built ~91–100 years ago
Built before 1978
Utilities
Water source: Lake Michigan
Public sewer
200+ amp electric service
HOA & community
No master association required
Community features include street lights and paved streets
Other
Some listing photos are virtually staged
Property not currently leased
Possession at closing
Electricity and solar
View estimated energy costs and solar savings for this home
This zoning district provides for moderate density residential and normal accessory uses. It is not intended to allow commercial, industrial, governmental, recreational, or like uses in this district; however, certain facilities required to serve educational, religious, or other needs of the area may be allowed within the district as conditional uses subject to restrictions intended to preserve and protect the residential character.
Permitted uses
Include but are not limited to:
Day care facility
Housing-Group
Housing-Single unit
Educational/school
Golf related
Park & open space
Oct 13, 2025 • Final
Exterior work - roof, residential
Tear off and replace the roof on a residential building.
Roofing
Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
2/10 Heat Factor
7 days above 98° expected this year, 14 days in 30 years
2/10 Wind Factor
1% chance of strong winds in next 30 years
4/10 Air Factor
4 unhealthy days expected this year, 5 days in 30 years
Provided by First Street
Historical weather
Highland Park, IL • 60035
Average low and high temperatures (°F)
30
15
38
21
53
33
59
42
64
47
78
61
81
68
80
66
76
60
66
50
50
38
36
23
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
86/ 100
Very good sunlight
Sunscore
This home receives average direct sun exposure in the zip code. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9.4 hrs
5.7 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 251 Oakland Dr
$1,562,359
$37K under list price of $1.60M
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $930K to $2.0M.