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$825,000 Contingent

  • For Sale
  • Contingent
  • Single Family
  • 2 Beds
  • 2 Full Baths
  • 1,938 Sq. Ft.
  • 2 Car Garage
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Don't let the storybook cottage charm fool you-this home lives much larger than it appears from the outside. Thoughtfully expanded and beautifully maintained, it offers generous living spaces while retaining all the warmth, character, and timeless appeal that make cottage-style homes so beloved. The main level features a spacious, sun-filled living room anchored by a beautiful wood-burning fireplace, an expansive updated kitchen with abundant cabinetry, and a dining area flanked by windows with plantation shutters. A bonus family room with vaulted ceilings and skylights, along with a full bathroom, adds valuable flexibility and completes the main level. Upstairs, you'll find two bedrooms with hardwood floors and a shared hall bath. The finished basement offers even more living space, featuring a second fireplace, a wall of closets, and a utility room with additional storage. Step outside to a picturesque, professionally landscaped garden with two patios and plenty of space for relaxing or entertaining. From its inviting curb appeal to its surprisingly spacious interior, this home strikes the perfect balance between charm and function. Timeless details and thoughtful updates are complimented by a versatile layout designed for comfortable everyday living and effortless entertaining.

Full Property Details for 376 Rosewood Ave

General

  • Price: $825,000
  • Taxes: $11,504 (2024)
  • Status: Contingent
  • Type: Single Family
  • Source: MRED
  • MLS ID: 12671135
  • Updated: 6/16/2026
  • Added to Site: 25 day(s) ago

Interior

  • Basement: Partially
  • Interior Features: Vaulted Ceiling(s), 1st-Floor Bath
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Fireplace(s): Living Room, Basement, Wood-Burning
  • Flooring: Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 2

Additional Information

  • Equipment: Carbon Monoxide Detectors, Ceiling Fan(s), Lawn Sprinkler
  • Other Features: School Bus Service

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 2
  • Parking Features: Concrete, Garage Door Opener, Yes, Garage Owned, Detached, Garage

Location

  • Area: Winnetka
  • County: Cook
  • Township: New Trier
  • Driving Directions: Willow Road East of Hibbard to Rosewood. North on Rosewood to 376

School Information

  • School District: 36
  • Elem School District: 36
  • Midd School District: 36
  • High School District: 203
  • Elementary School: Crow Island Elementary School
  • Middle School: Carleton W Washburne School
  • High School: New Trier Twp H.S. Northfield/Wi
  • Private School: New Trier Twp H.S. Northfield/Wi

Community

  • Assoc. Fees Include: None

Heating & Cooling

  • Cooling Type: Central Air Conditioning
  • Heating Type: Natural Gas

Utilities

  • Sewer: Public Sewer
  • Water: Lake Michigan, Public

Structural Information

  • Architectural Info: Cape Cod
  • Architectural Style: Cape Cod
  • Construction: Cedar, Stone
  • Exterior Const.: Cedar, Stone
  • Basement: Yes
  • Basement Desc.: Partially Finished, Partial
  • Foundation: Concrete Perimeter
  • Roof: Asphalt
  • Windows: Skylight(s), Plantation Shutters
  • Sub-Flooring: Hardwood
  • Square Feet: 1,938
  • Sq. Ft. Source: Assessor
  • Year Built: 1954
  • Built Before 1978: Yes

Lot Features

  • Lot Size Range: Less than .25 Acre
  • Lot Dimensions: 80 x 99

Financial Considerations

  • Parking Included: Yes
  • Assessment Year: 1954
  • Tax Amount: $11,504
  • Tax Year: 2024
  • Pays Sewer: Public Sewer

Disclosures and Reports

  • Ownership: Fee Simple
  • Property ID: 5201210210000

Listed by Jameson Sotheby's International Realty

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Listing agent

— 376 Rosewood Ave —

  • Jameson Sotheby's International Realty

(847) 951-5677

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NMLS#: 1598647

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Save up to an additional 20% by bundling your home and auto together!

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Find the right home insurance for your new home!

with our affiliated in-house agency

Request a Quote

Save up to an additional 20% by bundling your home and auto together!

Schools serving 376 Rosewood Ave

School Districts:Winnetka School District 36, New Trier Township High School District 203
NameGradesDistance
Crow Island Elementary School
1112 Willow Road, Winnetka, IL 60093
K-40.1 mi
Carleton W Washburne School
515 Hibbard Road, Winnetka, IL 60093
7-80.4 mi
New Trier Township H S Northfield
7 North Happ Road, Northfield, IL 60093
9-1.3 mi
New Trier Township H S Winnetka
385 Winnetka Avenue, Winnetka, IL 60093
10-121.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 376 Rosewood Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/11/2026
Listed
$825,000
57.14%
MLS
8/16/2017
Sold
$525,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 376 Rosewood Ave

Year
Property Taxes
Change
Tax Assessment
Change
2023
$11,055
—
$77,000
51%
2023
$11,055
6%
$51,000
—
2022
$10,384
-24%
$51,000
-9%
2021
$13,609
1%
$55,769
—
2020
$13,451
2%
$55,769
-2%
2019
$13,236
-18%
$56,761
-15%
2018
$16,086
13%
$67,064
—
2017
$14,177
-5%
$67,064
—
2016
$14,848
42%
$67,064
43%
2015
$10,464
-2%
$47,028
—
2014
$10,704
-4%
$47,028
-9%
2013
$11,202
1%
$51,414
-3%
2012
$11,041
—
$53,002
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Jameson Sotheby's International Realty

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376 Rosewood Avenue, Winnetka, IL 60093 (MLS# 12671135) is a Single Family property with 2 bedrooms and 2 full bathrooms. 376 Rosewood Avenue is currently listed for $825,000 and was received on June 11, 2026. Want to learn more about 376 Rosewood Avenue? Do you have questions about finding other Single Family real estate for sale in Winnetka? You can browse all Winnetka real estate or contact a Coldwell Banker agent to request more information.

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