744 Prospect Ave, Winnetka, IL 60093
Property image
Property image
OFF MARKET

744 Prospect Ave
Winnetka, IL 60093

  • 6 Beds
  • 5.5 Baths
  • 6,820 sqft (on 0.48 acres)

$3,744,500

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $25,101/mo*
Refinance Your Home

$3,744,500

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $25,101/mo*
Refinance Your Home
6 Beds
5.5 Baths
6,820 sqft
(on 0.48 acres)

Local Information

  • Map ViewExplore the area around 744 Prospect Ave.
  • Schools2 Elementary Schools2 Middle Schools2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Description

LUXURY AND ELEGANCE OF 1918 UPDATED WITH THE MAGNIFICENCE OF TODAY'S STANDARDS AND LUXURY! THE HOME YOU HAVE BEEN DREAMING OF IS AVAILABLE NOW! YOUR SEARCH FOR PERFECTION LIVES AT 744 PROSPECT AVENUE AND YOU CAN TOO. INCREDIBLE NEIGHBORHOOD, PARKS, SCHOOLS, SHOPPING AND LIFESTYLE AMENITIES ALL IN ONE LOCATION. JUST BLOCKS FROM LAKE MICHIGAN AND 16 MILES NORTH OF THE CITY OF CHICAGO, THIS HANDSOME GEORGIAN WAS BUILT TO LAST. FEATURING 5 BEDROOMS & 3.1 BATHS IN THE MAIN HOUSE. ALONG WITH A COACH HOME OVER THE 3 CAR GARAGE THAT FEATURES A LIVING ROOM, 1 BEDROOM & BATH AND GALLEY KITCHEN. THE MAIN HOUSE FEATURES A ROTUNDA ON THE BACK OF THE HOME AND PRESENTLY INCLUDES THE FAMILY ROOM AND MASTER SUITE ON THE SECOND FLOOR. THERE ARE BUILT-IN BOOK CASES IN SEVERAL ROOMS, ARCHITECTURAL DETAILS AND HARDWOOD FLOORS THROUGHOUT THE HOME. THE UPDATES INCLUDED A MAGNIFICENT KITCHEN WITH HUGE ISLAND AND FLOOR TO CEILING PANTRY SPACE. THE MAPLE PRALINE CABINETRY AND GRANITE COUNTERS. THE COOKING NICHE FEATURES A 48" GAS WOLF RANGE COMPLETE WITH PROOFING OVEN AND A POT FILLER. THE SUBZERO REFRIGERATOR HAS A MATCHING CABINET DOOR AND THE SUBZERO FREEZER DRAWERS ARE LOCATED IN THE ISLAND ALONG WITH THE BUILT IN MICRO-WAVE OVEN. THE MASTER SUITE IS THE ENVY OF THE NORTHSHORE WITH A DRESSING ROOM SURROUNDED BY MIRRORED CLOSETS, TWO WINDOW SEATS, TWO SEP BATHS AND THE MASSIVE BEDROOM LOCATED IN THE ROTUNDA. BEDROOMS 2 AND 3 ARE SEPARATED BY A JACK-N-JILL BATH. THERE IS ALSO A LARGE STORAGE AREA CURRENTLY BEING USED AS A LINEN CLOSET, BUT ALSO HAS A HOOK UP FOR LAUNDRY ON THE SECOND FLOOR. THE THIRD FLOOR FEATURES A EXPANSIVE BONUS ROOM GREAT FOR A GAME ROOM, STUDY AREA OR WHATEVER YOUR IMAGINATION CAN CREATE PLUS TWO ADDITIONAL BEDROOMS AND A FULL BATH. THERE IS A SEPARATE STAIRCASE FOR THIS SECTION OF THE HOME BUT A DUAL STAIRCASE FOR SAFETY. THE COUNTRY CLUB QUALITY REAR YARD HAS A STUNNING BRICK TERRACE ADJACENT TO THE KITCHEN AND STEPS AWAY FROM THE INGROUND POOL AND HOT TUB, JUST WAITING TO MELT AWAY THE STRESS OF THE DAY. THIS HOME, THIS SETTING, THE AMENITIES AND THE LIFESTYLE IT CREATES WILL GENERATE A LIFETIME OF GREAT FEELINGS AND MEMORIES. DON'T LET IT SLIP AWAY.
744 Prospect Ave, Winnetka, IL 60093 is a 6 bedroom, 6 bathroom, 6,820 sqft single-family home built in 1918. It last sold for $2,325,000 on Sep 10, 2021. It is currently off market. The Trulia Estimate is $3,744,500, with a rent estimate of $7,715/month.

Home Highlights

Parking
Garage
Outdoor
Porch, Patio, Deck, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 744 Prospect Ave

Interior Features

Interior Details
BasementAtticNumber of Rooms: 12Types of Rooms: Dining Room
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Tile, Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryer
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: MetalDeckExterior: BrickPatioPorch
Pool
Pool
Parking & Garage
GarageParking Spaces: 3Parking: Garage Detached

Property Information

Year Built
Year Built: 1918
Property Type / Style
Property Type: Single Family HomeArchitecture: Georgian

Community

Units in Building: 1

Lot Information

Lot Area: 0.48 acres

Price History for 744 Prospect Ave

DatePriceEventSource
09/10/2021$2,325,000Sold
MRED as distributed by MLS GRID #11080484
08/14/2021$2,549,900PendingMRED as distributed by MLS GRID #11080484
08/11/2021$2,549,900ContingentMRED as distributed by MLS GRID #11080484
07/13/2021$2,549,900PriceChange
MRED as distributed by MLS GRID #11080484
06/08/2021$2,649,900PriceChange
MRED as distributed by MLS GRID #11080484
05/07/2021$2,735,000Listed For SaleMRED as distributed by MLS GRID #11080484
04/07/2021ListingRemovedKeller Williams
01/10/2021$2,850,000Listed For SaleAgent Provided
08/25/2008$2,880,000Sold
MRED as distributed by MLS GRID #06822556
09/17/1998$1,650,000Sold
N/A

Market trends in Winnetka

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
26
7MoM
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Property Tax and Assessment

Year2024
Tax
Assessment$2,420,000
Home facts updated by county records

Comparable Sales for 744 Prospect Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
755 Lincoln Ave, Winnetka, IL
0.05
Single-Family Home
$2,650,000
10/27/25
5
4.5
5,904
680 Walden Rd, Winnetka, IL
0.27
Single-Family Home
$2,950,000
02/04/26
6
4.5
6,411
646 Prospect Ave, Winnetka, IL
0.21
Single-Family Home
$3,250,000
05/11/26
6
5.5
5,300
770 Prospect Ave, Winnetka, IL
0.04
Single-Family Home
$1,725,000
07/21/25
6
4.5
4,381
824 Humboldt Ave, Winnetka, IL
0.18
Single-Family Home
$2,180,000
07/30/25
5
4.5
4,800
845 Glen Oak Dr, Winnetka, IL
0.43
Single-Family Home
$2,555,000
05/20/26
5
4
4,597
500 Maple St, Winnetka, IL
0.53
Single-Family Home
$2,550,000
06/18/26
5
4
5,646
681 Walden Rd, Winnetka, IL
0.23
Single-Family Home
$1,905,000
04/28/26
5
4.5
3,737
891 Spruce St, Winnetka, IL
0.35
Single-Family Home
$2,610,000
08/15/25
6
5.5
5,000
803 Pine St, Winnetka, IL
0.20
Single-Family Home
$2,050,000
08/28/25
5
4
4,460

Nearby homes

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Assigned Schools

These are the assigned schools for 744 Prospect Ave.
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The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Winnetka

At least 78 Trulia users voted on each feature.

  • 94 % Say people would walk alone at night

  • 90 % Say it's dog friendly

  • 88 % Say kids play outside

  • 88 % Say there's holiday spirit

  • 87 % Say there are sidewalks

  • 82 % Say yards are well-kept

  • 81 % Say it's walkable to restaurants

  • 80 % Say parking is easy

  • 78 % Say there's wildlife

  • 75 % Say it's quiet

  • 74 % Say car is needed

  • 72 % Say there are community events

  • 71 % Say they plan to stay for at least 5 years

  • 71 % Say it's walkable to grocery stores

  • 70 % Say neighbors are friendly

  • 67 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • DRD
    "Great schools and public works. Incredible beaches. Great fire and police systems. Amazing playing fields for kids’ sports. "
    0
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  • allisonbowersbrown
    "Park district, block parties, parades, fireworks. Neighborhood get together, school and church events. "
    0
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  • Jillian D.
    "I take the metra and walk to work. It’s easy and about as fast in the train to Chicago as it is in a car. Going west without a car is not as doable though. "
    1
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  • Acparacchini
    "Great dog beach, easy walk to town with coffee shops, restaurants, etc and bring the dog! 4th of July parade and everyone brings their dogs "
    0
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  • Phil L. .
    "Great parks, families and restaurants. Easy walk to restaurants , train, and interesting stores. Lots of people out walking, running or on bikes. "
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  • Jillian D.
    "I take the train and walk. There are usually window seats available on the Metra when I leave winnetka at 7:21. "
    1
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  • Jillian D.
    "There are lots of green parks for doggos to play at! There’s also lil fountains where you can get water for people and dogs in the summer. "
    2
    Flag
  • Sarahvaile687
    "Winnetka music festival, summer music in the park...there are plenty of events hosted by the community."
    1
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  • Winnetka mom
    "I’ve lived here for 14 years and Winnetka is the most warm, welcoming neighborhood I’ve ever lived in!"
    1
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  • Benjamin J. D.
    "They would like it. It’s a great community with tons of parks. Move here! You won’t regret it. It’s like living in a Rockwell painting."
    1
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  • Mklein
    "Lived here for 22 years. Raised our family here. Would do it again given the chance. Great mix of people from different backgrounds and heritage. Only downfall is politically backwards and cannot get anything done in the village that’s required to stay current with infrastructure or lifestyle. "
    5
    Flag
  • Sbardoni29
    "Wonderful place to live. Gorgeous homes and great apartment living above shops and restaurants. So close to the lake and Metra runs right through city to downtown. "
    0
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  • Coveyandclay
    "family friendly and perfect for children! parks are wonderful and schools are best in country. park district facilities are top notch"
    0
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  • Coveyandclay
    "great parks and lots of kids playing there all the time. very family friendly. many kids events put on by park district also."
    0
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  • Erin K. C.
    "Very dog friendly. There is a great private dog beach that is well maintained with a dog wash and passholder only gate. All dogs are required to be well behaved and up to date on all shots. "
    0
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  • Acparacchini
    "Lived in Winnetka essentially since I was 9! Great place to raise a family. Beautiful homes, great town, great beaches, excellent schools, easy transportation to the city! "
    2
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  • Gabriel
    "Safe, quiet and architecturally nice. A great place to live and raise a family. Great schools and close to the lake. "
    0
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  • mtoyama60
    "Wonderful neighborhood close to lake and town and highly rated schools. Family community. Quiet residential street. Great investment."
    0
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  • Patty E.
    "I want to move here ,whith my kids."
    0
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Explore by feature - Pet Friendly

44 pet-friendly rentals in Winnetka, IL

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23 rentals with air conditioning in Winnetka, IL

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Homes for sale near 744 Prospect Ave

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Off Market Homes Near 744 Prospect Ave

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