1027 Cherry St, Winnetka, IL 60093
OFF MARKET

1027 Cherry St
Winnetka, IL 60093

  • 5 Beds
  • 4.5 Baths
  • 4,598 sqft

$1,960,400

Trulia Estimate
as of Aug 7, 2026
Est. Refi. Payment $13,363/mo*
Refinance Your Home

$1,960,400

Trulia Estimate
as of Aug 7, 2026
Est. Refi. Payment $13,363/mo*
Refinance Your Home
5 Beds
4.5 Baths
4,598 sqft

Local Information

  • Map ViewExplore the area around 1027 Cherry St.
  • Schools2 Elementary Schools2 Middle Schools2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1999
Living Area
4,598 sqft
Price/Sqft
$426
Parking
Garage

About this House

Sun filled, NOT IN FLOOD PLAIN, large scale center entry home, READY for occupancy! This is one of the best "tree" street locations, short distance to all 3 elementary schools, parks, train in town!! Expansive first floor, features beautifully detailed Living room with high ceilings that opens to library/office with custom built in file drawers & spacious formal dining room with dentil moldings at the front and hardwood floors. Large scale white kitchen opens to breakfast area w/built in cabinets, wet bar/refrigerator, family room w/blue stone fireplace & a full wall of floor to ceiling windows overlooking patio & private fenced yard. Huge mud/laundry room is off kitchen has tons of storage w/built in cabinets. On the second floor are 4 bedrooms and 3 full baths. There is a beautiful, very large scale master suite w/sitting area, 2 walk in closets, his & her sinks, separate shower and tub. Two family bedrooms share a full bath with double sinks. The 4th bedroom has an en suite bath. If you're looking for a second home office, one of the bedrooms has custom built in file drawers, which will be removed if purchaser wishes. Lower level full basement has Rec room, 5th bedroom and 4th full bath, workout room, walk in cedar closet, & large storage rm with built in shelves. This house is larger square footage than can be build today. 4500+ sq ft
1027 Cherry St, Winnetka, IL 60093 is a 5 bedroom, 5 bathroom, 4,598 sqft single-family home built in 1999. It last sold for $1,085,000 on May 1, 2020. It is currently off market. The Trulia Estimate is $1,960,400, with a rent estimate of $7,212/month.

Home Details for 1027 Cherry St

Interior Features

Interior Details
BasementNumber of Rooms: 12Types of Rooms: Walk In Closet, Dining Room
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDisposalDryerRefrigeratorWasher
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Tile, Carpet, Hardwood

Exterior Features

Exterior Home Features
Roof: Asphalt, OtherExterior: WoodPatio
Parking & Garage
GarageParking Spaces: 2Parking: Garage Detached

Property Information

Year Built
Year Built: 1999
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 8851 sqft

Price History for 1027 Cherry St

DatePriceEventSource
05/01/2020$1,085,000Sold
MRED as distributed by MLS GRID #10547679
04/04/2020$1,175,000PendingAgent Provided
03/06/2020$1,175,000PriceChange
Agent Provided
02/19/2020$1,199,000PriceChange
Agent Provided
11/23/2019$1,249,000PriceChange
Agent Provided
11/19/2019$1,265,000PriceChange
Agent Provided
10/14/2019$1,299,000Listed For SaleAgent Provided
05/10/2013$1,305,000Sold
MRED as distributed by MLS GRID #08247556
03/21/2013$1,385,000PendingAgent Provided
02/25/2013$1,385,000PriceChange
Agent Provided
01/12/2013$1,450,000Listed For SaleAgent Provided
10/05/2004$1,560,000Sold
N/A
02/09/1999$1,000,000Sold
N/A
03/05/1998$357,500Sold
N/A

Market trends in Winnetka

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.93M
Sale-to-List Price
—
Price per sq ft
$511
Available listings
34
8MoM
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Property Tax and Assessment

Year2024
Tax$27,235
Assessment$1,350,010
Home facts updated by county records

Comparable Sales for 1027 Cherry St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
995 Oak St, Winnetka, IL
0.10
Single-Family Home
$1,730,000
07/13/26
4
4.5
3,639
972 Elm St, Winnetka, IL
0.15
Single-Family Home
$1,350,000
06/24/26
5
3.5
2,800
917 Willow Rd, Winnetka, IL
0.28
Single-Family Home
$1,675,000
08/28/25
5
5
4,352
520 Provident Ave, Winnetka, IL
0.17
Single-Family Home
$2,100,000
12/08/25
5
4.5
3,800
1082 Ash St, Winnetka, IL
0.17
Single-Family Home
$2,100,000
06/08/26
4
3.5
3,932
1004 Oak St, Winnetka, IL
0.05
Single-Family Home
$2,945,000
01/21/26
5
5.5
5,500
1092 Spruce St, Winnetka, IL
0.24
Single-Family Home
$1,800,000
09/10/25
5
4.5
2,872
567 Provident Ave, Winnetka, IL
0.30
Single-Family Home
$1,716,000
08/15/25
5
4.5
3,747
1087 Ash St, Winnetka, IL
0.14
Single-Family Home
$1,670,000
07/23/26
4
3
3,163
1092 Ash St, Winnetka, IL
0.18
Single-Family Home
$1,875,000
04/24/26
4
3
3,622

Nearby homes

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Assigned Schools

These are the assigned schools for 1027 Cherry St.
View nearby schools on GreatSchools
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

  • 76 % Say it's quiet

  • 74 % Say car is needed

  • 72 % Say there are community events

  • 72 % Say it's walkable to grocery stores

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

  • 70 % Say neighbors are friendly

  • 66 % 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
    Flag
  • allisonbowersbrown
    "Park district, block parties, parades, fireworks. Neighborhood get together, school and church events. "
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • Phil L. .
    "Great parks, families and restaurants. Easy walk to restaurants , train, and interesting stores. Lots of people out walking, running or on bikes. "
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • Winnetka mom
    "I’ve lived here for 14 years and Winnetka is the most warm, welcoming neighborhood I’ve ever lived in!"
    1
    Flag
  • 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
    Flag
  • 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
    Flag
  • Coveyandclay
    "family friendly and perfect for children! parks are wonderful and schools are best in country. park district facilities are top notch"
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Gabriel
    "Safe, quiet and architecturally nice. A great place to live and raise a family. Great schools and close to the lake. "
    0
    Flag
  • mtoyama60
    "Wonderful neighborhood close to lake and town and highly rated schools. Family community. Quiet residential street. Great investment."
    0
    Flag
  • Patty E.
    "I want to move here ,whith my kids."
    0
    Flag

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Apartments for Rent

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Explore by feature - Pet Friendly

25 pet-friendly rentals in Winnetka, IL

Explore by feature - Air Conditioning

12 rentals with air conditioning in Winnetka, IL

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21 rentals with a washer/dryer in Winnetka, IL

Homes for sale near 1027 Cherry St

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Off Market Homes Near 1027 Cherry St

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