Beautiful spacious home for sale in historic Fort Sheridan within easy walking distance to Lake Michigan, lakeshore forest preserve, two Metra stations, and all the incredible restaurants and entertainment of Highwood. Featuring a large open floor plan main floor with vaulted ceiling and large windows allowing plenty of natural light into the living area. The kitchen is a chef's dream with a 60" Wolf stove with grill and griddle, generous cabinetry, large central island with power, and plenty of counter space. The dining room and living room feature elegant mill work and are ideal for entertaining. The family room features a fireplace and large windows to the backyard. Between the first and lower level built in bookcases usher you to a large finished basement that is endlessly adaptable to any use and has abundant storage space including a chest freezer. The second floor features two full bathrooms and four spacious bedrooms including a luxurious master suite with two walk-in closets and a spa-like en suite bathroom. The second floor was remodeled extensively in 2023 including new flooring, crown molding, painting, and a full remodel of both bathrooms. The master bathroom features a standalone tub, "wet room" style shower, and LED mirror with modern lighting. In addition to the remodel of the second floor in 2023, the main floor was fully painted as well as the exterior of the house. New sump pump installed in 2026. Home includes a modern 2 car garage and beautiful backyard including two raised cedar garden beds. Across the street is a charming playground perfect for entertaining children. Enjoy the serenity and natural beauty of this historic neighborhood, excellent school districts, immediate access to nature, and easy access to the city via Metra.
Est. $3,439 per month, based on comparable rentals
Sale and tax history for 44 Westover Rd
Sale History
Tax History
Date
Event
Price
MRED as Distributed by MLS Grid #12579144
Jun 1, 2026
Sold (MLS) (Closed)
$915,000
$244/sq ft
Mar 2, 2026
Contingent (Contingent - Continue to Show)
—
Feb 27, 2026
Listed (Active)
$899,000
$240/sq ft
MRED as Distributed by MLS Grid #11709993
May 8, 2023
Sold (MLS) (Closed)
$735,000
$196/sq ft
Mar 21, 2023
Pending
—
Mar 1, 2023
Contingent (Contingent - Continue to Show)
—
Jan 30, 2023
Listed (Active)
$750,000
$200/sq ft
+22
Historic Fort Sheridan, located on the shores of Lake Michigan is the place to enjoy, the place to live! This beautiful home, surrounded by history, encompasses everything for today's buyer. The open floorplan brings endless possibilities. The kitchen features all stainless steel appliances, an island to gather around, a 60" Wolf stove with griddle & grill, expansive cabinetry, butlers pantry, plus a breakfast area with views to the patio & yard. The kitchen opens to the bright family room anchored by a grand fireplace. The living room is bathed in light through large windows & skylit volume ceiling. The dining room, with detailed mill work, invites gatherings & celebrations. Newly refinished hardwood flooring, recessed lighting & fine window treatments define the 1st floor. The second floor's 4 large bedrooms include the Primary Suite, with private bath & two walk-in closets, three more bedrooms, a large hall bath & tons of closets provide space for everything & everyone. Enjoy two unique "loft areas" one for office (or sitting area) between the first & second floors & a second "library loft" between the first & lower level. The finished basement has room for office, exercise or play plus two huge closets! Large two car garage. Here, at 44 Westover, you'll be surrounded by nature, from the serene lake front to the surrounding bluffs, walking trails & open space. You'll be across from a small playground that's "almost" all your own! You'll enjoy the close proximity to shops & restaurants in Highwood, Highland Park & Lake Forest & you'll have easy access to the Metra, Sheridan Road & the highway!
MRED as Distributed by MLS Grid #08637204
Jun 18, 2014
Listing Removed
—
Jun 6, 2014
Listed (New)
*
MRED as Distributed by MLS Grid #07713789
May 20, 2011
Listing Removed
—
Apr 4, 2011
Price Changed (Price Change)
*
Mar 9, 2011
Price Changed (Price Change)
*
Jan 19, 2011
Listed (New)
*
MRED as Distributed by MLS Grid #06332382
Feb 9, 2007
Sold (MLS)
$628,000
$167/sq ft
Jan 24, 2007
Listing Removed
—
Nov 6, 2006
Listed
$645,000
$172/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$17,997 (+5.0%)
$50,282 + $173,527
$223,809
2024
$17,147 (+6.5%)
$50,282 + $173,527
$223,809
2023
$16,096 (+0.5%)
$47,405 + $163,597
$211,002
2022
$16,010 (+7.9%)
$42,730 + $147,464
$190,194
2021
$14,832 (+2.4%)
$46,940 + $137,118
$184,058
2020
$14,487 (+3.1%)
$45,375 + $132,545
$177,920
2019
$14,055 (−5.2%)
$45,163 + $131,925
$177,088
2018
$14,832 (+2.4%)
$46,846 + $145,806
$192,652
2017
$14,489 (+4.0%)
$46,846 + $145,806
$192,652
2016
$13,937 (+2.2%)
$46,576 + $144,965
$191,541
2015
$13,640 (−4.9%)
$44,341 + $138,009
$182,350
2013
$14,347 (+2.5%)
$46,355 + $132,647
$179,002
2012
$13,996 (+6.4%)
$47,557 + $136,088
$183,645
2011
$13,149 (+23.1%)
$48,291 + $138,188
$186,479
2010
$10,686 (+20.3%)
$46,144 + $126,840
$172,984
2008
$8,882 (+9.4%)
$48,902 + $134,421
$183,323
2007
$8,115
$47,156 + $129,622
$176,778
Public record
Beds
4
Baths
2.5
Stories
2
Lot width
—
Lot depth
—
Lot size
6,970 Sq. Ft.
Year renovated
1999
Sq. Ft.
3,731
Year built
1999
Style
Single Family Residential
County
Lake County
APN
16-10-420-004
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 15, 2026.
Property details
Parking
Parking Information
# of Garage Spaces: 2
# of Parking (Total): 2
Parking Features: Garage Door Opener, Garage Owned, Detached, Garage