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Highwood Real Estate, Homes and Condos for sale

All Highwood homes currently listed for sale in Highwood as of 09/17/2019 are shown below.  You can change the search criteria at any time by pressing the 'Change Search' button below.

If you have any questions or you would like more information about any Highwood homes for sale or other Highwood real estate, please contact us and one of our knowledgeable Highwood REALTORS® would be pleased to assist you.


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$649,000
944 Leonard Wood West, Highwood IL 60040
4
BEDS
3.1
BATHS
3,918
SQFT
$166
$/SQFT
0.19
ACRES
2003
BUILT
"Stunning home along the historic Fort Sheridan parade ground. When you walk through the front door you are immediately impressed w/the bright & spacious interior. Traditional open floor plan boasts high ceilings & natural light. Hardwood floors throughout the 1st flr, formal living rm & sep dinning rm overlook the beautiful 54 acre parade ground. Granite kitchen w/double oven, island, 42 cabinets, butlers pantry, plenty of storage + eating area overlooking backyard. Large master bdrm w/double c"
* PRICE LOWERED - $675,000 TO $649,000 
$635,000
42 Holabird Loop, Highwood IL 60040
4
BEDS
3.1
BATHS
3,072
SQFT
$207
$/SQFT
0.20
ACRES
2000
BUILT
"This Stunning 4+ Bedroom home in the Fabulous Fort Sheridan is a Must See! Enter through a Grand 2 Story Foyer and get ready to be IMPRESSED! 1st floor boasts a Bright Living Room, Formal Dining Room, Gourmet Kitchen with SS Appliances, Granite Island and Counters, Sunlit Eating area overlooking a Lavish Fenced Yard. Spacious Family Room with Fireplace is great for entertaining! Office, Powder & Mud Rooms conclude 1st level. Upstairs, step through French Doors into a Luxurious Master Suite, fea"
* LISTED OVER 120 DAYS 
$599,900
775 Endicott Road, Highwood IL 60040
4
BEDS
3.1
BATHS
3,798
SQFT
$158
$/SQFT
2001
BUILT
"Wonderful, Newer, Highly Upgraded Fort Sheridan Home with a 2 Story Foyer, Gorgeous Bridal Staircase, Brazilian Cherry Floors, Wonderful Custom Built-ins, Low E Windows, 9' Ceilings and Doorways. Built in Bose Speaker System on Main Floor and Patio. Gourmet Kitchen with 42 inch Cabinets, 10 foot Granite Island, Stainless, Sub- zero, Double Oven and so Much More! Huge Master Suite with 2 Walk in Closets and an Elegant Private Bath with a Jacuzzi and Multi-head Shower! Zoned Heat and A/C, HEPA Air"
* LISTED OVER 120 DAYS  * PRICE LOWERED - $625,000 TO $599,900 
$575,000
23 PRALLS Loop, Highwood IL 60040
4
BEDS
3.1
BATHS
2,890
SQFT
$199
$/SQFT
0.12
ACRES
1999
BUILT
"Welcome to the amazing community of Fort Sheridan! Gorgeous grounds, meticulously maintained community, convenient access to Lake Michigan, multiple beaches (dog beach), great restaurants & bars, & public transportation to work downtown. The community offers many fun social activities throughout the year & the neighborhood is filled with multiple playgrounds. This is a stunning home offering abundant natural light throughout, high ceilings & windows, a modern open floor plan great for enterta"
$449,000
140 Michigan Avenue, Highwood IL 60040
4
BEDS
3.1
BATHS
2,544
SQFT
$176
$/SQFT
0.17
ACRES
1929
BUILT
"Completely remodeled brick home with brand new appliances, brand new AC/furnace/water heater, new windows, and refinished hardwood floors throughout of the house. Master bathroom was newly built. Lovely private great room on the second floor of the garage with AC and hearing. Desired location and nice neighborhood."
* NEW LISTING 
$425,000
697 Lyster Road, Highwood IL 60040
3
BEDS
3.1
BATHS
2,560
SQFT
$166
$/SQFT
2002
BUILT
"This Immaculate 3 Bedroom Townhome in the Fabulous Fort Sheridan is move-in-ready for YOU! First level features a large Family Room with sliding doors, Wet Bar, Powder Room, and a Laundry Room with sink. Second Level boasts a Formal Dining Room with French Doors, Gourmet Kitchen with Stainless Steel Appliances, Granite Counters, and Sunlit Eating area. Spacious Living Room with Fireplace is great for entertaining and opens to an oversized wooden deck! Second Powder Room concludes this level. St"
$409,900
20 Webster Avenue Unit G, Highwood IL 60040
3
BEDS
3.1
BATHS
1,991
SQFT
$206
$/SQFT
2019
BUILT
"Introducing The Dakota End Unit*Upgraded And Gorgeous*2000 Square Feet*Now Is The Time For You To Buy In The Exploding Community Of Highwood Before It's Too Late*Groundbreaking New Construction Townhomes At An Exceptional Price*Be The First To Live In These Modern*Open Concept 3 Bedroom/2.5 Bath Units*Stylishly Designed*Loads Of Windows*Premium Finishes*42Cabinets*Quartz Countertops*Subway Tile*Frigidaire Stainless Appliances*Large Island And Breakfast Area*Lower Level Family Room*Den Or Office*"
$389,900
20 Webster Avenue Unit C, Highwood IL 60040
3
BEDS
3.1
BATHS
1,791
SQFT
$218
$/SQFT
2019
BUILT
"Introducing The Camden Model At Webster Place*Gorgeous Finishes Here*Now Is The Time For You To Buy In The Exploding Community Of Highwood Before It's Too Late*Groundbreaking New Construction Townhomes At An Exceptional Price*Be The First To Live In These Modern*Open Concept 3 Bedroom/2.5 Bath Units*Stylishly Designed*Loads Of Windows*Premium Finishes*42Cabinets*Quartz Countertops*Subway Tile*Frigidaire Stainless Appliances*Large Island And Breakfast Area*Lower Level Family Room*Den Or Office*Be"
$389,900
20 Webster Avenue Unit B, Highwood IL 60040
3
BEDS
3.1
BATHS
1,791
SQFT
$218
$/SQFT
2019
BUILT
"Introducing The Camden Model At Webster Place*Gorgeous Finishes Here*Now Is The Time For You To Buy In The Exploding Community Of Highwood Before It's Too Late*Groundbreaking New Construction Townhomes At An Exceptional Price*Be The First To Live In These Modern*Open Concept 3 Bedroom/2.5 Bath Units*Stylishly Designed*Loads Of Windows*Premium Finishes*42Cabinets*Quartz Countertops*Subway Tile*Frigidaire Stainless Appliances*Large Island And Breakfast Area*Lower Level Family Room*Den Or Office*Be"
$350,000
319 Oak Terrace Avenue, Highwood IL 60040
4
BEDS
3.1
BATHS
0.17
ACRES
1940
BUILT
"Excellent investment opportunity with a 2 bedroom / 1 bathroom single family home in the front and a 2 bedroom / 1 bathroom coach house in the back. Features new siding, roof, asphalt driveway, etc. Long term tenants in both properties (20 years & 6 years... Lease will go month to month starting in August, to allow for a new owner to take over). This property has been owned by the same family for nearly 50 years. Beyond the coach house is a nice yard. Current rents are $1,350 each (Could be clos"
$349,000
615 Western Avenue, Highwood IL 60040
5
BEDS
3.1
BATHS
0.17
ACRES
1964
BUILT
"This clean and pristine 2-flat in Highwood is move-in ready! The property is situated on a deep lot, with plenty of room to garden and room for extra cars. 2nd flr unit features 3 x-large bdrms with spacious living areas. 1st flr unit features 2 x-large bdrms with spacious living areas. Both units have loads of storage. Close to bike trails, walking paths, restaurants, festivals and all Highwood has to offer. An excellent investment opportunity or a great place to live and rent the extra apartm"
* LISTED OVER 120 DAYS 
$299,000
10 Michigan Avenue, Highwood IL 60040
3
BEDS
3.1
BATHS
0.18
ACRES
1928
BUILT
"Two unit duplex is nicely updated and located in one of the most desirable streets in Highwood, Features hardwood floors. Tile floors in lower level and each unit has separate heat and electric. Large driveway and plenty of storage. Across street from Exmoor Country Club."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $319,000 TO $299,000 
$295,000
108 Prairie Avenue, Highwood IL 60040
5
BEDS
3.1
BATHS
0.14
ACRES
1941
BUILT
"In town all Brick two flat home. First floor offers ceramic and hardwood floors, crown molding, nicely updated granite eat in kitchen, living room dining room combo with wood-burning gas starting fireplace, three bedrooms, two bathrooms and den/ante room. Second floor currently rented offering extra income. Unit has private entrance, kitchen, living room, two bedrooms and one bathroom. Full basement with shared laundry facilities and plenty of space for a rec room and bedroom. Plumbed for a b"
* PRICE LOWERED - $299,900 TO $295,000 
$280,000
121 High Street, Highwood IL 60040
4
BEDS
3.1
BATHS
1,956
SQFT
$143
$/SQFT
0.16
ACRES
"Quiet and desirable Highwood Location. Open floor plan on the first floor with refinished hardwood flooring and freshly painted throughout. The kitchen has plenty of white cabinetry, a breakfast nook, eat-in kitchen, and ceramic tile flooring. Living room with wood-burning fireplace. Additional first-floor office/playroom. The second floor has carpet for a cozy feeling during the winter season. Each floor having a full bathroom for extra convenience. Wood deck, fenced backyard, and an extended "
* NEW LISTING 
$230,000
206 Highwood Avenue, Highwood IL 60040
2
BEDS
3.1
BATHS
1,021
SQFT
$225
$/SQFT
0.27
ACRES
1918
BUILT
"Charming 1-Level Living Home, in an Amazing Location, 2 Blocks from Town/Train. Close to Schools, Parks. Great Highwood Shops & Restaurants! Property Zoned R3A - Restricted Multi-Family. Huge approx. 57' x 200' Lot. Hardwood Floors Thru-out, Older Updated Kitchen, Older Updated Windows. Walk-up Attic with Great Possibility for Expansion. Full Unfinished Basement, Big Patio & Enormous Fenced Backyard. 2-Car Detached Garage. Home Being Sold As Is."
* LISTED OVER 120 DAYS  * PRICE LOWERED - $245,000 TO $230,000 
$185,000
730 SHERIDAN Road Unit 2C, Highwood IL 60040
2
BEDS
3.1
BATHS
1,037
SQFT
$178
$/SQFT
1983
BUILT
"2 BEDRROMS 1 BATHROOM, LARGE BALCONY AND STORAGE ROOM CONDO IN A WELL MAINTEINED BRICK BUILDING CONVENIENTLY LOCATED, CLOSE TO DOWNTOWN, RESTAURANTS, THE LAKE, THE TRAIN, THE SHOPPINGS 2-TANDEM PARKING SPACES."
* LISTED OVER 120 DAYS 
 
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