New Trier Township H S Winnetka, IL homes for sale & real estate

86 homes

Sort:

Recommended

ABOUT THIS HOME
New Trier Township H S Winnetka, IL Homes for Sale
Gracefully tucked away on 1.55 acres of lush manicured grounds, 62 Woodley Road is a true Southern-inspired masterpiece reimagined for today's living. From the moment you approach the iconic black lacquered screen door with its Chippendale detail, you're drawn into a world of classic sophistication. Step inside to a grand foyer entrance where timeless black and white checkered marble floors meet a dramatic double atrium staircase wrapped in elegant wrought iron setting the tone for the architectural beauty that unfolds throughout. Gracious comfort exudes throughout this 13 room estate with that desirable southern exposure that allows natural sunlight to flood through the endless windows out

$2,739,000

6 beds5 baths7,000 sq ft

62 Woodley Rd, Winnetka, IL 60093

Custom french doors • 1.55 acres • Formal living room

3D WALKTHROUGH

ABOUT THIS HOME
New Trier Township H S Winnetka, IL Homes for Sale
Welcome to a truly exceptional ranch-style smart home, nestled in the serene northeast corner of Glenview, surrounded by lush greenery on a generously sized lot. This extraordinary residence boasts an expansive layout of approximately 2280 sq ft, showcasing elegant designer finishes and a plethora of bespoke features that marry technology with style. You'll instantly fall in love with this distinctive home, tailor-made for daily living, leisurely retreats, and vibrant entertaining. As you enter, you are greeted by a grand foyer that flows gracefully into a formal living room, where a cozy fireplace beckons beneath soaring 12-ft ceilings-setting the perfect ambiance for gatherings. The heart

$1,150,000

3 beds2.5 baths2,280 sq ft

623 Echo Ln, Glenview, IL 60025

0.25 acre lot • 2 garage spots • Listed 65 days

3D WALKTHROUGH

ABOUT THIS HOME
New Trier Township H S Winnetka, IL Homes for Sale
House Beautiful! Stunning Newer Custom Built Brick Colonial Home in Wilmette. 5100 Sq ft. Built like a fortress! Designer exterior trim with composite panels and columns. Knockout layout features Gorgeous 2 story foyer with custom oak staircase and sitting area. 10' ft ceilings throughout! Bay windows with tons of sunlight. Unique trim includes beautiful crown molding and 10" floor baseboards. 5 bedrooms and 4.5 baths. 2 offices, absolutely beautiful! Oak hardwood floors with walnut inlay's. Spacious living room with gas burning fireplace. Full formal dining room features custom brass chandelier by Savoy house. Enormous kitchen with high end appliances including Sub Zero refrigerator,

$1,489,000

5 beds4.5 baths5,100 sq ft

1133 Manor Dr, Wilmette, IL 60091

High end appliances • Bay windows • Custom oak staircase

ABOUT THIS HOME
New Trier Township H S Winnetka, IL Homes for Sale
Extraordinary opportunity for an in town oasis in the heart of East Winnetka on ~ 1/2 acre of lushly landscaped grounds with walk to everywhere. A private, fully renovated classic located in a premier location with 150 ft frontage, just steps to town, train, beach, Community House and more. Meticulously transformed and completely reimagined inside and out with one of the best first floor living spaces, this 6 bedrooms and 5.1 bath home showcases the highest quality finishes and attention to detail, including a thoughtfully redesigned floor plan for today's lifestyle, exquisite architectural millwork and replaced hardwood floors, every modern amenity, and newer sun-filled windows with serene

$3,150,000

6 beds5.5 baths6,384 sq ft

646 Prospect Ave, Winnetka, IL 60093

0.43 acre lot • 4 garage spots • Built 1898

NEW CONSTRUCTION

ABOUT THIS HOME
New Trier Township H S Winnetka, IL Homes for Sale
Introducing magnificent new luxury construction located in the highly coveted McKenzie School District & minutes from the heart of Wilmette's vibrant downtown. Nestled on a quiet charming cobble stone tree lined street & rare oversized extra wide & deep lot (60X171), this 5,800 sq. ft. luxe home features 8 bedrooms, 6.1 baths, and 3 car garage equipped with EV charger. Skillfully constructed with unwavering commitment to meticulous craftsmanship, high end quality, thoughtful design, and sleek sophistication- 1209 Maple is an extraordinary opportunity to customize your dream home. The expansive main level features separate formal living and dining rooms and vast open-concep

$3,199,000

8 beds6.5 baths5,800 sq ft

1209 Maple Ave, Wilmette, IL 60091

0.24 acre lot • 3 garage spots • Built 2026

Property at 764 Boal Pkwy, Winnetka, IL 60093, 3 beds, 3.5 baths

$1,550,000

3 beds3.5 baths3,146 sq ft

764 Boal Pkwy, Winnetka, IL 60093

Property at 410 Green Bay Rd, Glencoe, IL 60022, 4 beds, 3.5 baths

$949,000

4 beds3.5 baths3,962 sq ft

410 Green Bay Rd, Glencoe, IL 60022

Property at 513 Edens Ln, Northfield, IL 60093, 4 beds, 2.5 baths

$749,900

4 beds2.5 baths2,149 sq ft

513 Edens Ln, Northfield, IL 60093

Property at 2536 Old Glenview Rd, Wilmette, IL 60091, 3 beds, 2 baths

$780,000

3 beds2 baths1,460 sq ft

2536 Old Glenview Rd, Wilmette, IL 60091

Property at 1295 Sunview Ln, Winnetka, IL 60093, 4 beds, 3 baths

$1,299,000

4 beds3 baths2,316 sq ft

1295 Sunview Ln, Winnetka, IL 60093

Property at 320 Woodley Rd, Winnetka, IL 60093, 6 beds, 6 baths

$5,349,000

6 beds6 baths13,000 sq ft

320 Woodley Rd, Winnetka, IL 60093

Property at 908 Elm Pl, Glencoe, IL 60022, 6 beds, 4.5 baths

$2,375,000

6 beds4.5 baths4,736 sq ft

908 Elm Pl, Glencoe, IL 60022

Property at 410 Prairie Ave, Wilmette, IL 60091, 5 beds, 5.5 baths

$2,849,000

5 beds5.5 baths5,600 sq ft

410 Prairie Ave, Wilmette, IL 60091

Property at 1370 Sunview Ln, Winnetka, IL 60093, 4 beds, 4 baths

$1,995,000

4 beds4 baths4,632 sq ft

1370 Sunview Ln, Winnetka, IL 60093

Property at 1180 Oak Ridge Dr, Glencoe, IL 60022, 5 beds, 5.5 baths

$3,390,000

5 beds5.5 baths— sq ft

1180 Oak Ridge Dr, Glencoe, IL 60022

Property at 1925 Lake Ave #318, Wilmette, IL 60091, 2 beds, 2 baths

$360,000

2 beds2 baths1,383 sq ft

1925 Lake Ave #318, Wilmette, IL 60091

Property at 2430 Dorina Dr, Northfield, IL 60093, 8 beds, 7.5 baths

$2,795,000

8 beds7.5 baths7,800 sq ft

2430 Dorina Dr, Northfield, IL 60093

Property at 64 Crescent Dr, Glencoe, IL 60022, 6 beds, 7.5 baths

$3,799,900

6 beds7.5 baths11,500 sq ft

64 Crescent Dr, Glencoe, IL 60022

Property at 979 Vine St, Winnetka, IL 60093, 4 beds, 1.5 baths

$950,000

4 beds1.5 baths2,100 sq ft

979 Vine St, Winnetka, IL 60093

Property at 15 Landmark, Northfield, IL 60093, 3 beds, 2.5 baths

$775,000

3 beds2.5 baths2,784 sq ft

15 Landmark, Northfield, IL 60093

Property at 628 Happ Rd, Northfield, IL 60093, 3 beds, 1.5 baths

$749,000

3 beds1.5 baths1,602 sq ft

628 Happ Rd, Northfield, IL 60093

Property at 828 Lavergne Ave, Wilmette, IL 60091, 3 beds, 1.5 baths

$420,000

3 beds1.5 baths1,247 sq ft

828 Lavergne Ave, Wilmette, IL 60091

Property at 455 Sheridan Rd, Kenilworth, IL 60043, 7 beds, 8.5 baths

$5,975,000

7 beds8.5 baths11,000 sq ft

455 Sheridan Rd, Kenilworth, IL 60043

Property at 219 Lincoln Dr, Glencoe, IL 60022, 6 beds, 9.5 baths

$7,888,000

6 beds9.5 baths12,709 sq ft

219 Lincoln Dr, Glencoe, IL 60022

Property at 1630 Sheridan Rd Unit 2F, Wilmette, IL 60091, 2 beds, 2.5 baths

$699,000

2 beds2.5 baths1,600 sq ft

1630 Sheridan Rd Unit 2F, Wilmette, IL 60091

Property at 1531 Wilmette Ave, Wilmette, IL 60091, 3 beds, 2 baths

$750,000

3 beds2 baths1,345 sq ft

1531 Wilmette Ave, Wilmette, IL 60091

Property at 801 Harvard St, Wilmette, IL 60091, 6 beds, 6.5 baths

$2,850,000

6 beds6.5 baths5,595 sq ft

801 Harvard St, Wilmette, IL 60091

Property at 821 Harms Rd, Glenview, IL 60025, 4 beds, 4 baths

$2,200,000

4 beds4 baths— sq ft

821 Harms Rd, Glenview, IL 60025

Property at 526 Linden Ave, Wilmette, IL 60091, 5 beds, 6.5 baths

$3,250,000

5 beds6.5 baths5,875 sq ft

526 Linden Ave, Wilmette, IL 60091

Property at 542 Laramie Ave, Wilmette, IL 60091, 3 beds, 2 baths

$500,000

3 beds2 baths1,260 sq ft

542 Laramie Ave, Wilmette, IL 60091

Property at 1265 Longmeadow Ln, Glencoe, IL 60022, 6 beds, 7 baths

$3,795,000

6 beds7 baths— sq ft

1265 Longmeadow Ln, Glencoe, IL 60022

Property at 313 Hawthorn Ave Unit F, Glencoe, IL 60022, 2 beds, 1.5 baths

$400,000

2 beds1.5 baths1,500 sq ft

313 Hawthorn Ave Unit F, Glencoe, IL 60022

Property at 1517 Gregory Ave, Wilmette, IL 60091, 6 beds, 5.5 baths

$1,993,888

6 beds5.5 baths— sq ft

1517 Gregory Ave, Wilmette, IL 60091

Property at 527 Warwick Rd, Kenilworth, IL 60043, 6 beds, 6.5 baths

$2,735,000

6 beds6.5 baths5,500 sq ft

527 Warwick Rd, Kenilworth, IL 60043

Property at 794 Greenwood Ave, Glencoe, IL 60022, 6 beds, 7.5 baths

$5,749,000

6 beds7.5 baths9,000 sq ft

794 Greenwood Ave, Glencoe, IL 60022

Property at 1492 Asbury Ave, Winnetka, IL 60093, 4 beds, 2.5 baths

$1,099,000

4 beds2.5 baths2,380 sq ft

1492 Asbury Ave, Winnetka, IL 60093

Property at 1133 Mayfair Ln, Glencoe, IL 60022, 4 beds, 3 baths

$1,519,000

4 beds3 baths2,977 sq ft

1133 Mayfair Ln, Glencoe, IL 60022

Property at 941 Harms Rd, Glenview, IL 60025, 3 beds, 2.5 baths

$1,290,000

3 beds2.5 baths3,480 sq ft

941 Harms Rd, Glenview, IL 60025

Property at 2185 New Willow Rd, Northfield, IL 60093, 3 beds, 3 baths

$799,000

3 beds3 baths4,278 sq ft

2185 New Willow Rd, Northfield, IL 60093

Property at 396 Forest Edge Dr, Glencoe, IL 60022, 5 beds, 4.5 baths

$2,999,000

5 beds4.5 baths4,843 sq ft

396 Forest Edge Dr, Glencoe, IL 60022

Property at 32 Woodley Rd, Winnetka, IL 60093, 5 beds, 5.5 baths

$4,950,000

5 beds5.5 baths9,908 sq ft

32 Woodley Rd, Winnetka, IL 60093

Viewing page 2 of 3

Based on information submitted to the MLS GRID as of Fri Nov 21 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

More to explore in New Trier Township H S Winnetka, IL

Featured
Bedroom

How to buy a house in New Trier Township H S Winnetka, IL

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Illinois

Chicago homes for sale
$350,000
Naperville homes for sale
$629,500
Schaumburg homes for sale
$299,900
Arlington Heights homes for sale
$432,500
Glenview homes for sale
$754,500
Oak Park homes for sale
$400,000
Evanston homes for sale
$435,000
Des Plaines homes for sale
$385,000
Orland Park homes for sale
$379,450
Downers Grove homes for sale
$514,000
Mount Prospect homes for sale
$419,500
St. Charles homes for sale
$455,000
Skokie homes for sale
$445,000
Glen Ellyn homes for sale
$550,000
Northbrook homes for sale
$582,000

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.