1249 Cherry St, Winnetka, IL 60093
OFF MARKET

1249 Cherry St
Winnetka, IL 60093

  • 5 Beds
  • 3 Baths
  • 2,591 sqft

$1,292,200

Trulia Estimate
as of Aug 7, 2026
Est. Refi. Payment $8,834/mo*
Refinance Your Home

$1,292,200

Trulia Estimate
as of Aug 7, 2026
Est. Refi. Payment $8,834/mo*
Refinance Your Home
5 Beds
3 Baths
2,591 sqft

Local Information

  • Map ViewExplore the area around 1249 Cherry St.
  • Schools2 Elementary Schools2 Middle Schools2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1929
Living Area
2,591 sqft
Price/Sqft
$499
Parking
Garage

About this House

Charming English Country Stone house with Slate roof ideally located on one of Winnetka's favorite tree streets. 2015 remodel with new open concept kitchen-family room. Three new full baths with floor radiant heating. New and updated electrical. House completely repiped with copper w/ new water service from the street. Ensuite Master bedroom with large walk in closet. Second floor new bath with large soaking tub. Grand living room with stone fireplace and 10ft beamed ceiling. First floor study/guest bedroom with connecting full bath. High-end white cabinet cook's kitchen with island prep area, oversized double oven, cooktop and bar seating. Screened porch overlooking new professionally landscaped yard with new 2016 flagstone patio. LL family room with english bar, bedroom with walk-in closet and laundry room. 2.5 car garage with walk up storage room. Walk to Crow Island, Skokie, Washburn schools along with Neilsen Tennis Center and ice center. Home has full walk-in attic. Welcome Home!
1249 Cherry St, Winnetka, IL 60093 is a 5 bedroom, 3 bathroom, 2,591 sqft single-family home built in 1929. It last sold for $812,000 on May 14, 2018. It is currently off market. The Trulia Estimate is $1,292,200, with a rent estimate of $5,484/month.

Home Details for 1249 Cherry St

Interior Features

Interior Details
BasementAtticNumber of Rooms: 8Types of Rooms: Walk In Closet, Dining Room
Heating & Cooling
Heating: GasAir ConditioningCooling System: CentralHeating Fuel: Gas
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood, Linoleum Vinyl

Exterior Features

Exterior Home Features
Roof: SlateExterior: StonePatioPorch
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1929
Property Type / Style
Property Type: Single Family HomeArchitecture: Bungalow

Community

Units in Building: 1

Lot Information

Lot Area: 9347 sqft

Price History for 1249 Cherry St

DatePriceEventSource
05/14/2018$812,000Sold
MRED as distributed by MLS GRID #09869233
03/04/2018$825,000PendingAgent Provided
02/28/2018$825,000PriceChange
Agent Provided
02/19/2018$879,000Listed For SaleAgent Provided
01/16/2015$675,000Sold
MRED as distributed by MLS GRID #08653417
10/24/2014$699,000PendingAgent Provided
08/03/2014$699,000PriceChange
Agent Provided
06/24/2014$725,000Listed For SaleAgent Provided

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$12,845
Assessment$565,660
Home facts updated by county records

Comparable Sales for 1249 Cherry St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1253 Cherry St, Winnetka, IL
0.01
Single-Family Home
$875,000
08/29/25
3
3
1,920
1087 Ash St, Winnetka, IL
0.31
Single-Family Home
$1,670,000
07/23/26
4
3
3,163
1288 Sunview Ln, Winnetka, IL
0.34
Single-Family Home
$875,000
01/12/26
5
3.5
2,714
1092 Ash St, Winnetka, IL
0.32
Single-Family Home
$1,875,000
04/24/26
4
3
3,622
270 Euclid Ave, Winnetka, IL
0.36
Single-Family Home
$1,384,000
04/08/26
4
3
2,898
1092 Spruce St, Winnetka, IL
0.35
Single-Family Home
$1,800,000
09/10/25
5
4.5
2,872
1105 Elm St, Winnetka, IL
0.32
Single-Family Home
$1,340,000
06/24/26
3
3.5
2,435
972 Elm St, Winnetka, IL
0.53
Single-Family Home
$1,350,000
06/24/26
5
3.5
2,800
303 Auburn Ave, Winnetka, IL
0.30
Single-Family Home
$1,400,000
05/04/26
4
3
3,737
1020 Cherry St, Winnetka, IL
0.43
Single-Family Home
$1,120,000
07/13/26
4
2
1,854

Nearby homes

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Assigned Schools

These are the assigned schools for 1249 Cherry St.
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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

  • 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
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Apartments for Rent

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Explore by feature - Pet Friendly

25 pet-friendly rentals in Winnetka, IL

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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 1249 Cherry St

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Off Market Homes Near 1249 Cherry St

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