Winnetka, IL Real Estate Listings

About Winnetka Real Estate Listings 

Interested in calling Winnetka, IL, home? Browse available Winnetka homes and Winnetka real estate listings below. Our advanced North Shore real estate website features all Winnetka property listings currently on the real estate market, and is updated every 15 minutes, so Winnetka home buyers are viewing the most up-to-date property listings. For additional information on any Winnetka homes for sale, just click th "Request Info" button when viewing the details of that property. We can provide you with disclosures, past sales history, dates, and prices of homes and condos recently sold nearby, and more.

We also encourage all users to register for a free account so that you can receive email alerts whenever new Winnetka homes hit the market that match your search preferences, allowing you to stay one step ahead of other home buyers. Or you can also break down your search right now and browse Winnetka homes by property type, architectural style, or home feature. 

Search Winnetka, IL Homes & Real Estate Listings

• All Listings
• Under $100,000
• $500,000 - $600,000
• $600,000 - $700,000
• $900,000 - $1,000,000
• Over $1,000,000

Bedrooms

Bathrooms

Price Range

Save Search

Sort by:

Newest First

New

$1,995,000

1235 Scott Avenue, Winnetka, 60093

5 Beds 7 Baths 4,546 SqFt Residential MLS® # 12504622

New

$2,799,000

334 Woodland Avenue, Winnetka, 60093

4 Beds 5 Baths 3,748 SqFt Residential MLS® # 12507097

New

$1,995,000

335 Fairview Avenue, Winnetka, 60093

4 Beds 5 Baths 3,288 SqFt Residential MLS® # 12513222

New Contingent

$650,000

943 Westmoor Road, Winnetka, 60093

2 Beds 3 Baths 1,619 SqFt Residential MLS® # 12499034

Contingent

$599,000

630 Winnetka Mews 402, Winnetka, 60093

2 Beds 2 Baths 1,675 SqFt Residential MLS® # 12500601

Contingent

$1,649,000

611 Ash Street, Winnetka, 60093

4 Beds 4 Baths 0 SqFt Residential MLS® # 12507234

Contingent

$1,950,000

520 Provident Avenue, Winnetka, 60093

4 Beds 5 Baths 3,800 SqFt Residential MLS® # 12499816

$2,850,000

205 Scott Avenue, Winnetka, 60093

5 Beds 5 Baths 6,162 SqFt Residential MLS® # 12503772

$1,595,000

1350 Westmoor Trail, Winnetka, 60093

5 Beds 5 Baths 4,925 SqFt Residential MLS® # 12502961

$3,295,000

889 Cherry Street, Winnetka, 60093

5 Beds 7 Baths 5,339 SqFt Residential MLS® # 12505224

Contingent

$1,250,000

305 Poplar Street, Winnetka, 60093

3 Beds 3 Baths 3,128 SqFt Residential MLS® # 12499401

$8,800

↓ $700

526 Orchard Lane, Winnetka, 60093

4 Beds 4 Baths 3,076 SqFt Residential Lease MLS® # 12497473

Contingent

$2,195,000

1161 Pine Street, Winnetka, 60093

4 Beds 3 Baths 3,667 SqFt Residential MLS® # 12466389

Contingent

$575,000

471 Linden Street, Winnetka, 60093

3 Beds 2 Baths 1,927 SqFt Residential MLS® # 12448472

Contingent

$2,295,000

386 Fairview Avenue, Winnetka, 60093

4 Beds 4 Baths 5,284 SqFt Residential MLS® # 12494483

$2,739,000

62 Woodley Road, Winnetka, 60093

6 Beds 6 Baths 7,000 SqFt Residential MLS® # 12493480

$3,000

↓ $250

1097 Tower Road A, Winnetka, 60093

2 Beds 1 Bath 1,200 SqFt Residential Lease MLS® # 12483024

$2,888,000

331 Sheridan Road, Winnetka, 60093

5 Beds 5 Baths 0 SqFt Residential MLS® # 12490342

Contingent

$589,000

730 Oak Street, Winnetka, 60093

3 Beds 3 Baths 1,600 SqFt Residential MLS® # 12489453

$2,499,900

180 Apple Tree Road, Winnetka, 60093

5 Beds 4 Baths 4,800 SqFt Residential MLS® # 12488843

$1,995,000

1370 Sunview Lane, Winnetka, 60093

4 Beds 5 Baths 4,632 SqFt Residential MLS® # 12488904

$950,000

979 Vine Street, Winnetka, 60093

4 Beds 2 Baths 2,100 SqFt Residential MLS® # 12476547

Contingent

$2,299,000

43 Indian Hill Road, Winnetka, 60093

4 Beds 6 Baths 0 SqFt Land MLS® # 12475558

$1,299,000

1295 Sunview Lane, Winnetka, 60093

0 Beds 0 Baths 0 SqFt Land MLS® # 12472653

1 2

Next

What to Expect When Buying a Home in Winnetka, IL

Winnetka is located along Chicago’s North Shore and offers direct access to lakefront parks, public beaches, and a walkable village center. The housing stock includes a range of architectural styles, including Georgian, Tudor, and newer custom builds. Residents benefit from Metra access, high-performing schools, and close to local boutiques and restaurants. Quiet streets, mature trees, and large lot sizes contribute to the area’s appeal.

Most homes are detached single-family properties, with very limited attached housing options. Homes east of Green Bay Road tend to carry higher values due to lake proximity, but buyers also find desirable listings throughout the western sections. Whether you're relocating locally or arriving from outside the region, we’ll help you evaluate current inventory, recent sales data, and long-term value indicators before making a move.

Who Typically Buys Homes in Winnetka?

Winnetka attracts buyers who prioritize school performance, neighborhood consistency, and access to lakefront spaces. Families with children are common, particularly those seeking top-ranked public education and outdoor recreation. Buyers upgrading from smaller homes elsewhere in the North Shore often target Winnetka for its larger properties and deep yards. Relocating professionals with hybrid or flexible work schedules also consider the area for its train access and quiet surroundings.

Some buyers moving from the city select Winnetka to balance proximity with a more residential pace. Others move within the community to adjust their home size while remaining close to schools and amenities. Our team regularly works with first-time suburban buyers and long-time North Shore residents, helping each client focus their search around layout, price, and future resale considerations.

FAQs About Buying and Living in Winnetka, IL

How far is Winnetka from downtown Chicago?

Winnetka is roughly 20 miles north of Chicago. The Metra Union Pacific North Line offers direct rail service to Ogilvie Transportation Center, and driving downtown takes approximately 40 minutes, depending on traffic.

Are public schools in Winnetka highly rated?

Yes. Winnetka is served by New Trier Township High School and District 36 elementary schools, which are consistently recognized for academic performance and extracurricular programs. School access is one of the primary reasons families move to the area.

What types of homes are common in Winnetka?

The area is known for large single-family homes, including both historic and recently built properties. Architectural styles range from traditional brick to newer transitional builds. Condos and townhomes are limited but available in some pockets near the village center.

What’s the typical price range for homes in Winnetka?

Home prices generally range from the upper $600,000s to several million dollars for lakefront properties. The average single-family home often sells between $1.2 million and $2.5 million, depending on location, lot size, and updates.

Is Winnetka considered walkable?

Parts of Winnetka near the downtown core are pedestrian-friendly, with easy access to shops, the library, and the train station. Many neighborhoods have sidewalks and quiet traffic, making walking and biking common for local trips.

Are there recreational amenities in Winnetka?

Yes. Residents have access to public beaches, the Winnetka Golf Club, indoor and outdoor tennis courts, and bike paths. The Park District also runs youth programs, fitness facilities, and seasonal events throughout the year.

How competitive is the housing market in Winnetka?

Demand in Winnetka remains steady, with low inventory during peak seasons driving competitive conditions. Homes in move-in-ready condition or close to schools tend to sell quickly. We can guide you through market timing and offer strategies to strengthen your offer.

What property taxes can I expect?

Property taxes in Winnetka reflect the area’s public services and school funding. Rates vary based on assessed value and local taxing bodies. We’ll review annual tax estimates and historical trends with you when evaluating homes.