286 Leonard Wood South, Highland Park, Illinois 60035

Subdivision > Fort Sheridan

$560,000

For Sale
Status: New
Sqft: 1,856
Cost/Sqft: $302
Beds: 2
Baths: 2
Year Built: 1885
Property Taxes: $8,938
Days On Market: 1
Lot Size: 0,00

Description

Experience the perfect blend of historic character, comfort and convenience in this rarely available two-bedroom, first-floor condo, ideally situated in the coveted Tower Barracks at Fort Sheridan. Meticulously maintained and spacious, this distinctive duplex-down residence enjoys sweeping views of the iconic Parade Grounds and showcases soaring ceilings, exposed brick and timeless architectural details. The light-filled living room features a cozy fireplace and flows seamlessly into the dining area. The well-appointed eat-in kitchen offers granite countertops, generous workspace and access to a private, south-facing deck. The inviting outdoor retreat is perfect for morning coffee, dining or the avid gardener. The primary bedroom features two large walk-in closets and a well-appointed bath. The bright, finished lower-level offers exceptional additional living space, enhanced by natural light and heated floors. A generously sized family room provides the perfect setting for relaxing or gathering, while a second bedroom with a large walk-in closet, updated full bath and convenient office nook offer flexibility for guests, work or everyday living. A spacious laundry room and abundant storage add to the home's functionality. Additional amenities include one heated garage parking space. Set within the extraordinary Fort Sheridan community, this home offers a lifestyle unlike any other on the North Shore. Nestled between Lake Forest, Highland Park and Highwood along the shores of Lake Michigan, this historic enclave features beach access, miles of scenic walking and nature trails, breathtaking ravines and beautifully preserved architecture. Enjoy the peaceful natural surroundings while being just a short walk from the Fort Sheridan Metra station, Starbucks and vibrant downtown Highwood. Don't miss this wonderful opportunity to enjoy the history, natural beauty and distinctive lifestyle of Fort Sheridan, paired with the comfort and convenience of thoughtfully designed living.

Property Specifics

Condos/Townhomes
3
—
1885
Finished, Full
Brick
—
Tower Barracks
No
—
Lake
Fort Sheridan
594 / Monthly
Insurance, Exterior Maintenance, Lawn Care, Scavenger, Snow Removal
Public
Public Sewer
Central Air
Gas, Radiant Floor
12806711
16104080120000

Property History

DATE: EVENT: PRICE: SOURCE:
13 Nov, 2026 Listed for sale $560,000 MRED MLS

Room Specifics

All Bedroom Info:
Total Bedrooms: 2
Bedrooms Above Ground: 2
Bedrooms Below Ground: 0
Master Bedroom Info:
Dimensions: 14X11
Location: Main Level
Floor Type: —
Second Bedroom Info:
Dimensions: 12X14
Location: Lower
Floor Type: —
Bathroom Info:
Full Bathrooms: 2
Partial Bathrooms: 0
Bathroom Amenities: —
Bathroom in Basement: 1
Dining Room Info:
Dimensions: 9X18
Location: Main Level
Floor Type: —
Kitchen Info:
Dimensions: 18X16
Location: Main Level
Floor Type: —
Features: Eating Area-Table Space
Laundry Room Info:
Dimensions: 9X12
Location: Lower
Floor Type: —
Living Room Info:
Dimensions: 14X17
Location: Main Level
Floor Type: —
Family Room Info:
Dimensions: 21X26
Location: Lower
Floor Type: —
Additional Rooms Info:
Rooms: Deck
Basement: Finished, Full
First Additional Room Info:
Name: Deck
Dimensions: 16X18
Location: Main Level
Floor Type: —

Other Specifics

1
—
Heated Garage, Garage Owned, Attached, Garage
In Unit
—
—
—
Landscaped
Common
—
None
Storage, Walk-In Closet(s)
Range, Microwave, Dishwasher, Refrigerator, Washer, Dryer, Disposal
Not in DB
Park
Bike Room/Bike Trails, Park, Trail(s)
Gas Log

Tax History

Year Property Taxes
2026 $8,938

Nearby Similar Homes

240 Whistler Road, Highland Park, Illinois 60035
For Sale
$2,100,000
5 beds / 5.1 baths / 6,989 ft2
Condos/Townhomes / Built: 1895
23

271 Whistler Road, Highland Park, Illinois 60035
For Sale
$699,999
2 beds / 2.1 baths / 1,692 ft2
Condos/Townhomes / Built: 1885
36

155 Whistler Road, Highland Park, Illinois 60035
For Sale
$649,000
2 beds / 2.1 baths / 1,768 ft2
Condos/Townhomes / Built: 1885
29

701 Lyster Road, Highwood, Illinois 60040
For Sale
$689,900
3 beds / 2.1 baths / 3,040 ft2
Condos/Townhomes / Built: 2002
16

23 Rienzi Lane, Highwood, Illinois 60040
For Sale
$849,000
3 beds / 2.1 baths / 2,800 ft2
Condos/Townhomes / Built: 2005
30

Nearby Sold Comparables

286 Leonard Wood, Highland Park, Illinois 60035
Sold
$329,000
2 beds / 2.0 baths / 2,050 ft2
Condos/Townhomes / Built: —
5681

286 Leonard Wood Drive, Highland Park, Illinois 60035
Sold
$375,000
2 beds / 2.0 baths / 1,665 ft2
Condos/Townhomes / Built: 1885
4995

268 Leonard Wood South, Highland Park, Illinois 60035
Sold
$349,500
2 beds / 2.0 baths / 1,792 ft2
Condos/Townhomes / Built: 1885
4818

268 Leonard Wood South Avenue, Highland Park, Illinois 60035
Sold
$399,000
2 beds / 2.0 baths / 1,792 ft2
Condos/Townhomes / Built: 1885
3988

268 Leonard Wood South, Highland Park, Illinois 60035
Sold
$575,000
2 beds / 3.0 baths / 2,414 ft2
Condos/Townhomes / Built: 1885
1643

290 Leonard Wood South, Highland Park, Illinois 60035
Sold
$357,500
1 beds / 1.0 baths / 1,400 ft2
Condos/Townhomes / Built: 1885
7381


Contact Agent

Listing Provided By

@properties Christie's International Real Estate