342 Rosewood Ave

Winnetka IL 60093

4585 sq. ft.

Single-Family

Last sold for $2,050,000

Paige Dooley, last sold this property on 12 December 2025 after 60 days on market.

Overview

Sophisticated perfection on an extra wide lot in one of Winnetka's most picturesque neighborhoods! Breathtaking 5BR/4.1BA beauty immediately captivates with its stately facade, grand walk-up entrance and exceptional curb appeal. A seamless blend of comfortable elegance and contemporary refinement, every detail reflects thoughtful design and superior craftsmanship.A bold designer palette complemented by crown moldings, French doors, arched entryways, expansive windows, rich hardwood floors, custom wall coverings, and stunning light fixtures- all contributing to an effortlessly flowing layout. An elegant dining room flows into the butler's pantry and an exceptionally scaled eat-in kitchen/family room with a large center island, walk-in pantry and top of the line appliances. A sunlit breakfast area opens directly to the backyard and adjoins the "heart of the home" great room, anchored by a cozy, gas burning fireplace. The framed French doors lead to everyone's favorite : a newly installed spacious "outdoor room" and a gorgeous Red Spade backyard redesign. Upstairs, the serene primary suite serves as a luxurious retreat with a lofted ceiling, custom built-ins, a balcony, generous walk-in closet and beautiful spa bath with double sink vanity, Toto bidet, steam shower and radiant heated floors. Three additional bedrooms and two handsome baths plus second floor laundry provides ultimate convenience. An additional layer of living space in the lower level with an oversized recreation room, custom wet bar with sink, dishwasher and refrigeration, fabulous temperature-controlled wine cellar, exercise room/fifth bedroom and full bath - making this area ideal for entertaining or unwinding in style. Outside, the picturesque and private setting with exterior lighting, blue stone patios, grey composite decking, elegant brick paver accents, thoughtfully constructed field stone retaining walls and elevated landscape beds - all highlight the gorgeous and professionally curated landscape with mature trees and blooming perennials. Flawlessly maintained and thoughtfully upgraded with many incredible recent updates: furnace, AC, hot water heater, attic insulation, sump pump, whole house filtration system, plant watering system, outdoor lighting, fresh paint, restained hardwood floors and many more.... This spectacular, turnkey home in a fabulous walk to everything location - including town, train, schools and parks - truly, leaves nothing to be desired in this don't miss opportunity. Home not in the floor plain -see property disclosure and FEMA attachment explaining.

Features

4 bedrooms

5 bathrooms

2 carspaces

2 garage spaces

4585 sq. ft. floor area

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Winnetka over the last 12 months, the estimated median property value of 342 Rosewood Ave is $1.74m.

Median value

$1.74m

Estimated value range

$514k - $5m

Median days on market

Estimated value trend

increase over the last 12 months

Average days on market is based on recent, comparable sales in Winnetka. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 342 Rosewood Ave

2025

Sold

$2,050,000

12 Dec 2025 by Paige Dooley

2016

Sold

$1,353,750

20 Dec 2016 by Tom McCarey, of @properties Christie's International Real Estate

2015

Sold

$1,275,000

06 Nov 2015 by Frank Capitanini, of Coldwell Banker Realty

Happy sellers in Winnetka

We have insufficient information to provide an overview of customer satisfaction for Winnetka. Viewing the agent profiles, reviews and sales for Winnetka can provide insights for this location.