1259 Cherry St, Winnetka, IL 60093
Property image
Property image
OFF MARKET

1259 Cherry St
Winnetka, IL 60093

  • 3 Beds
  • 2 Baths
  • 2,070 sqft (on 0.27 acres)

$1,852,400

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $12,455/mo*
Refinance Your Home

$1,852,400

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $12,455/mo*
Refinance Your Home
3 Beds
2 Baths
2,070 sqft
(on 0.27 acres)

Local Information

  • Map ViewExplore the area around 1259 Cherry St.
  • Schools2 Elementary Schools2 Middle Schools2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Description

Terrific Location and amazing opportunity in Crow Island School District! Remodel existing home or build new.Property is in need of TLC and is being sold as-is.
1259 Cherry St, Winnetka, IL 60093 is a 3 bedroom, 2 bathroom, 2,070 sqft single-family home built in 1928. It last sold for $405,000 on Jul 30, 2018. It is currently off market. The Trulia Estimate is $1,852,400, with a rent estimate of $4,656/month.

Home Highlights

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

Home Details for 1259 Cherry St

Interior Features

Interior Details
BasementNumber of Rooms: 9Types of Rooms: Dining Room
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: StuccoFoundation Type: Crawl Raised
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 1928
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.27 acres

Price History for 1259 Cherry St

DatePriceEventSource
07/30/2018$405,000Sold
MRED as distributed by MLS GRID #09879301
06/21/2018$429,000PendingAgent Provided
05/30/2018$429,000PriceChange
Agent Provided
05/21/2018$439,000PriceChange
Agent Provided
05/14/2018$449,000PriceChange
Agent Provided
05/01/2018$459,000PriceChange
Agent Provided
04/23/2018$469,000PriceChange
Agent Provided
04/10/2018$489,000Listed For SaleAgent Provided
03/29/2018$275,000Sold
N/A
03/25/2018$499,000PendingAgent Provided
03/09/2018$499,000Listed For SaleAgent Provided
01/01/2018$399,900ListingRemovedAgent Provided
11/21/2017$399,900PriceChange
Agent Provided
10/30/2017$439,900PriceChange
Agent Provided
10/10/2017$459,900PriceChange
Agent Provided
09/25/2017$479,900PriceChange
Agent Provided
09/12/2017$499,900PriceChange
Agent Provided
09/06/2017$524,900PriceChange
Agent Provided
06/10/2017$554,900PriceChange
Agent Provided
05/25/2017$470,000PriceChange
Agent Provided
04/19/2017$554,900PriceChange
Agent Provided
04/18/2017$564,900PriceChange
Agent Provided
04/03/2017$554,900PriceChange
Agent Provided
10/13/2016$564,900PriceChange
Agent Provided
09/22/2016$574,900PriceChange
Agent Provided
09/07/2016$599,900Listed For SaleAgent Provided
07/26/2013$540,000Sold
MRED as distributed by MLS GRID #08344485
05/05/2006$690,000Sold
N/A
09/19/2003$550,000Sold
N/A
08/20/1999$400,000Sold
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$1,665,000
Home facts updated by county records

Comparable Sales for 1259 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
1101 Oak St, Winnetka, IL
0.30
Single-Family Home
$1,375,000
07/31/25
4
2.5
2,170
1595 Mount Pleasant St, Northfield, IL
0.68
Single-Family Home
$525,000
10/09/25
3
1.5
1,418
1166 Cherry St, Winnetka, IL
0.18
Single-Family Home
$1,400,000
07/21/25
4
3.5
3,611
320 Lagoon Dr, Northfield, IL
0.59
Single-Family Home
$629,000
10/24/25
3
1.5
1,386
1105 Elm St, Winnetka, IL
0.33
Single-Family Home
$1,340,000
06/24/26
3
3.5
2,435
342 Latrobe Ave, Northfield, IL
0.64
Single-Family Home
$672,500
01/06/26
4
2
2,188
270 Euclid Ave, Winnetka, IL
0.37
Single-Family Home
$1,384,000
04/08/26
4
3
2,898
303 Auburn Ave, Winnetka, IL
0.31
Single-Family Home
$1,400,000
05/04/26
4
3
3,737
913 Cherry St, Winnetka, IL
0.65
Single-Family Home
$950,000
03/19/26
4
1.5
1,396

Nearby homes

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Assigned Schools

These are the assigned schools for 1259 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

  • 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
    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

44 pet-friendly rentals in Winnetka, IL

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23 rentals with air conditioning in Winnetka, IL

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41 rentals with a washer/dryer in Winnetka, IL

Homes for sale near 1259 Cherry St

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Off Market Homes Near 1259 Cherry St

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