Winnetka, IL Homes

/29
$950,000

Pending
- 3 Beds
- 2 Baths
- 2,333 Sq Ft
154 Glenwood Ave, Winnetka, IL 60093

Rare opportunity in East Winnetka. Nestled beside a quiet neighborhood park, this beautifully updated 1919 Tudor blends timeless architectural character with thoughtful modern updates in one of Winnetka's most sought-after locations. A scenic path just behind the home provides easy access to the Green Bay Trail, making it an easy walk or bike ride to Hubbard Woods School, the Metra, and downtown

Bonnie Tripton @properties Christie's International Real Estate

154 Glenwood Ave, Winnetka, IL 60093
/18
$2,195 Per Month
- 1 Bed
- 1 Bath
- 900 Sq Ft
- Condo for Rent
545 Chestnut St Unit E545-302, Winnetka, IL 60093

Book a tour by copying this link into your browser. PLEASE MAKE SURE TO INCLUDE THE ADDRESS & UNIT # DURING BOOKING TO CONFIRM AVAILABILITY. Welcome to your new home in vibrant Winnetka, IL! This charming property offers a comfortable living experience in a picturesque neighborhood, surrounded by fantastic dining options and retail stores. With easy access to prominent educational

545 Chestnut St Unit E545-302, Winnetka, IL 60093
/2
$950,000

Sold Jan 20, 2026

Unlisted Address
- 4 Beds
- 3 Baths
- 2,062 Sq Ft
- Built 1928
Last Sold Summary
- $461/SF
- 2 Days On Market
Current Estimated Value $1,081,116

Last Listing Agent Susan Duffey @properties Christie's International Real Estate

Unlisted Address

/9
Est $1,490,986

Not Listed For Sale

338 Linden St, Winnetka, IL 60093
- 3 Beds
- 3 Baths
- 2,407 Sq Ft
- Built 1962
338 Linden St, Winnetka, IL 60093

Last Sold Summary
- 0 Days On Market
Last Listing Agent Christina Fawcett @properties Christie's International Real Estate

/44
$1,795,000

Pending
- 5 Beds
- 3.5 Baths
1037 Oak St, Winnetka, IL 60093

Located in the heart of Winnetka and within the highly sought-after Crow Island School District, this impeccably maintained 5-bedroom, 3.1-bath home checks every box. Thoughtfully reimagined and beautifully updated, the first floor offers exceptional flow, abundant natural light and timeless finishes throughout. At the center of the home is the stunning kitchen, completely gutted and renovated in

Catherine Dunlop @properties Christie's International Real Estate

1037 Oak St, Winnetka, IL 60093
/7
$2,195 Per Month
- 1 Bed
- 1 Bath
- 700 Sq Ft
- Condo for Rent
545 Chestnut St Unit E811-308, Winnetka, IL 60093

Book a tour by copying this link into your browser. PLEASE MAKE SURE TO INCLUDE THE ADDRESS & UNIT # DURING BOOKING TO CONFIRM AVAILABILITY. Welcome to your next home in the charming district of Winnetka, IL! This inviting property is ideally situated near an array of restaurants and department stores, making it perfect for both convenience and enjoyment. With key locations such as Saint

545 Chestnut St Unit E811-308, Winnetka, IL 60093
/2
$910,000

Sold Dec 17, 2025

158 Woodland Ave, Winnetka, IL 60093
- 3 Beds
- 3 Baths
- 2,200 Sq Ft
- Built 1920
Last Sold Summary
- 2% Above List Price
- $414/SF
Current Estimated Value $1,028,987

Last Listing Agent Catherine O'Connell @properties Christie's International Real Estate

158 Woodland Ave, Winnetka, IL 60093

/22
Est $1,515,398

Not Listed For Sale

1028 Cherry St, Winnetka, IL 60093
- 4 Beds
- 3.5 Baths
- 2,711 Sq Ft
- Built 1925
1028 Cherry St, Winnetka, IL 60093

Last Sold Summary
- 0 Days On Market
Last Listing Agent Katie Traines @properties Christie's International Real Estate

/60
$4,995,000
- 6 Beds
- 9 Baths
- 7,480 Sq Ft
1380 Westmoor Trail, Winnetka, IL 60093

It is exceptionally rare to find a privately set masterpiece with sweeping views of the Winnetka Golf Course that also offers the opportunity to step directly into a freshly completed 2025/2026 designer showcase renovation. Nestled on a beautifully landscaped half-acre site overlooking the golf course, this extraordinary stone residence has been impeccably transformed through a comprehensive

Lori Nieman @properties Christie's International Real Estate

1380 Westmoor Trail, Winnetka, IL 60093
/10
$2,450 Per Month
- 2 Beds
- 1 Bath
- 700 Sq Ft
- Condo for Rent
894 Green Bay Rd Unit 896B-06, Winnetka, IL 60093

Book a tour by copying this link into your browser. PLEASE MAKE SURE TO INCLUDE THE ADDRESS & UNIT # DURING BOOKING TO CONFIRM AVAILABILITY. Welcome to your new home in the charming district of Winnetka, IL! This inviting property offers a prime location surrounded by an array of delightful restaurants and department stores, making everyday errands a breeze. Additionally, you’ll be just a

894 Green Bay Rd Unit 896B-06, Winnetka, IL 60093
/46
$2,200,000

Sold Oct 15, 2025

1503 Edgewood Ln, Winnetka, IL 60093
- 4 Beds
- 5 Baths
- 3,319 Sq Ft
- Built 1927
Last Sold Summary
- 23% Above List Price
- $663/SF
- 3 Days On Market
Current Estimated Value $2,017,813

Last Listing Agent Sarah Lyons @properties Christie's International Real Estate

1503 Edgewood Ln, Winnetka, IL 60093

/32
Est $1,910,173

Not Listed For Sale

804 Boal Pkwy, Winnetka, IL 60093
- 4 Beds
- 3.5 Baths
- 4,490 Sq Ft
- Built 1955
804 Boal Pkwy, Winnetka, IL 60093

Last Sold Summary
- 16 Days On Market
Last Listing Agent Selma Nemeth @properties Christie's International Real Estate

/45
$1,950,000

Pending
- 5 Beds
- 3 Baths
- 3,280 Sq Ft
1440 Tower Rd, Winnetka, IL 60093

An extraordinary Colonial offering timeless elegance, exceptional estate-like privacy, and breathtaking views along the 12th hole of the Winnetka Golf Course. Set on nearly one acre of beautifully landscaped grounds and positioned approximately 250 feet from the road, this property feels like a private retreat yet is just minutes from downtown Winnetka, the Metra, premier shopping, dining, and

Sarah Lyons @properties Christie's International Real Estate

1440 Tower Rd, Winnetka, IL 60093
/18
$2,050 Per Month
- 1 Bed
- 1 Bath
- 1,000 Sq Ft
- Condo for Rent
894 Green Bay Rd Unit 896A0-9, Winnetka, IL 60093

Book a tour by copying this link into your browser. PLEASE MAKE SURE TO INCLUDE THE ADDRESS & UNIT # DURING BOOKING TO CONFIRM AVAILABILITY. Welcome to your new home in the charming district of Winnetka, IL, where comfort meets convenience. This inviting property offers a wonderful living experience close to an array of local amenities, including an excellent selection of restaurants and

894 Green Bay Rd Unit 896A0-9, Winnetka, IL 60093
/49
$2,350,000

Sold Jan 09, 2026

180 Apple Tree Rd, Winnetka, IL 60093
- 5 Beds
- 3.5 Baths
- 4,800 Sq Ft
- Built 1955
Last Sold Summary
- 6% Below List Price
- $490/SF
- 45 Days On Market
Current Estimated Value $2,419,610

Last Listing Agent Jena Radnay @properties Christie's International Real Estate

180 Apple Tree Rd, Winnetka, IL 60093

/31
Est $2,974,860

Not Listed For Sale

824 Boal Pkwy, Winnetka, IL 60093
- 5 Beds
- 7 Baths
- 6,300 Sq Ft
- Built 2019
824 Boal Pkwy, Winnetka, IL 60093

Last Sold Summary
- 6 Days On Market
Last Listing Agent Paul Gorney eXp Realty

/58
$4,200,000
- 6 Beds
- 9 Baths
- 6,950 Sq Ft
1128 Mount Pleasant Rd, Winnetka, IL 60093

Built to impress, this beautifully designed, custom crafted home is discreetly tucked in next to Crow Island Woods you will have nature at your doorstep and be perfectly situated on an amazing half-acre lot. This stunning 5 + bedroom, 6.3 bath home combines timeless architecture with thoughtful modern accents, offering a level of comfortable, elegant living in the North Shore's most sought-after

Eugene Fu @properties Christie's International Real Estate

1128 Mount Pleasant Rd, Winnetka, IL 60093
/26
$625,000

Sold Jul 01, 2026

680 Green Bay Rd Unit 306, Winnetka, IL 60093
- 2 Beds
- 2 Baths
- 1,680 Sq Ft
- Built 1978
Last Sold Summary
- $372/SF
- 2 Days On Market
Current Estimated Value $616,036

Last Listing Agent Connie Dornan @properties Christie's International Real Estate

680 Green Bay Rd Unit 306, Winnetka, IL 60093

/5
Est $1,528,730

Not Listed For Sale

1501 Tower Rd, Winnetka, IL 60093
- 4 Beds
- 4.5 Baths
- 3,462 Sq Ft
- Built 1949
1501 Tower Rd, Winnetka, IL 60093

Last Sold Summary
- 22 Days On Market
Last Listing Agent Carrie Tarzon @properties Christie's International Real Estate

/44
$1,725,000
- 5 Beds
- 4.5 Baths
- 6,580 Sq Ft
555 Cherry St, Winnetka, IL 60093

Beautifully restored idyllic Victorian home expanded for today's living features a flexible floorplan with easy flow, generously sized rooms, dramatic ceiling heights, detailed millwork and plaster moldings, inlaid floors and an abundance of tall oversized windows. The lushly landscaped property highlighted by majestic oak trees is ideally located on a favorite east Winnetka street near lakefront

Howard Meyers Compass

555 Cherry St, Winnetka, IL 60093
/33
$1,925,000

Sold Oct 23, 2025

355 Myrtle St, Winnetka, IL 60093
- 5 Beds
- 4.5 Baths
- 4,544 Sq Ft
- Built 1930
Last Sold Summary
- 12% Below List Price
- $424/SF
- 45 Days On Market
Current Estimated Value $2,078,119

Last Listing Agent Mary Grant @properties Christie's International Real Estate

355 Myrtle St, Winnetka, IL 60093

/28
Est $1,338,876

Not Listed For Sale

1476 Scott Ave, Winnetka, IL 60093
- 3 Beds
- 2.5 Baths
- 2,970 Sq Ft
- Built 1967
1476 Scott Ave, Winnetka, IL 60093

Last Sold Summary
- 4 Days On Market
Last Listing Agent Joanne Hudson Compass

/43
$2,569,900
- 6 Beds
- 6 Baths
- 7,000 Sq Ft
62 Woodley Rd, Winnetka, IL 60093

The time is NOW to jump on this "southern charm" architectural beauty on exclusive Woodley Road. Beautifully appointed on a magnificent 1.5 acre lush lot with rolling greens, this estate is in prime position to be elevated to the next level of luxury. With over 8500 square feet of classic tasteful space over three floors of living, this house could never be duplicated close for the list price as

Jena Radnay @properties Christie's International Real Estate

62 Woodley Rd, Winnetka, IL 60093
/35
$1,477,000

Sold Aug 15, 2025

1218 Cherry St, Winnetka, IL 60093
- 4 Beds
- 3.5 Baths
- 1,962 Sq Ft
- Built 1940
Last Sold Summary
- 21% Above List Price
- $753/SF
- 4 Days On Market
Current Estimated Value $1,538,540

Last Listing Agent Mary Egebrecht Jameson Sotheby's Intl Realty

1218 Cherry St, Winnetka, IL 60093

/59
Est $1,597,081

Not Listed For Sale

1321 Scott Ave, Winnetka, IL 60093
- 6 Beds
- 5 Baths
- 3,358 Sq Ft
- Built 1928
1321 Scott Ave, Winnetka, IL 60093

Last Sold Summary
- 3 Days On Market
Last Listing Agent Joanne Hudson Compass

/3
$1,290,000
- Land
- 1.36 Acres
- $948,529 per Acre
2033 Winnetka Rd, Winnetka, IL 60093

Reduced new price for the land is more than $100,000 less than the original !! Rare chance to own 1.36 acres of land on beautiful Winnetka rd will provide you endless possibilities to build your dream home. Incredible opportunity to collaborate with experienced luxury builder or bring your own builder. Winnetka High School District. Amazing location- close to Northfield Park District,Westfield

Natalya Gorodetsky Core Realty & Investments, Inc

2033 Winnetka Rd, Winnetka, IL 60093
/23
$639,000

Sold Mar 27, 2026

640 Winnetka Mews Unit 405, Winnetka, IL 60093
- 3 Beds
- 3 Baths
- 1,862 Sq Ft
- Built 1971
Last Sold Summary
- $343/SF
- 5 Days On Market
Current Estimated Value $631,566

Last Listing Agent Joanne Hudson Compass

640 Winnetka Mews Unit 405, Winnetka, IL 60093

/10
Est $1,069,352

Not Listed For Sale

826 Humboldt Ave, Winnetka, IL 60093
- 3 Beds
- 1.5 Baths
- 1,059 Sq Ft
- Built 1913
826 Humboldt Ave, Winnetka, IL 60093

Last Sold Summary
- 873 Days On Market
Last Listing Agent Paul Harb Wilmette Real Estate & Management Company LLC

/14
$16,900,000
- 6 Beds
- 10 Baths
- 15,000 Sq Ft
915 Sunset Rd, Winnetka, IL 60093

A Home That Redefines Scale and Lifestyle. With over 17,000 square feet of meticulously designed living space-including 7,500 square feet dedicated to main-floor living and entertaining-this residence represents one of the most comprehensive lifestyle homes ever built in Winnetka. Designed and built by noted builder, every element was curated for collectors, entertainers, and owners who value

Mary Maris Village Realty Group Inc

915 Sunset Rd, Winnetka, IL 60093
/10
$500,000

Sold May 01, 2026

97 High St, Winnetka, IL 60093
- 2 Beds
- 3.5 Baths
- 1,364 Sq Ft
- Built 1949
Last Sold Summary
- 17% Below List Price
- $367/SF
- 16 Days On Market
Current Estimated Value $530,036

Last Listing Agent Lilia Balan Pavlova Properties

97 High St, Winnetka, IL 60093

/26
Est $1,739,878

Not Listed For Sale

850 Eldorado St, Winnetka, IL 60093
- 3 Beds
- 2.5 Baths
- 2,240 Sq Ft
- Built 1945
850 Eldorado St, Winnetka, IL 60093

Last Sold Summary
- 3 Days On Market
Last Listing Agent Meg Sudekum @properties Christie's International Real Estate

/26
$3,200,000

Pending
- 5 Beds
- 4.5 Baths
- 3,683 Sq Ft
48 Indian Hill Rd, Winnetka, IL 60093

Tucked away in one of Winnetka's most coveted private roads, this exceptional 5-bedroom, 4.5-bathroom estate offers a prime spacious lot surrounded by majestic, mature trees. The property boasts an extraordinary setting that guarantees ultimate privacy while maximizing its unique geographic advantage. The home features dramatic, unobstructed vistas overlooking the historic Indian Hill Golf Course

Joseph Nash @properties Christie's International Real Estate

48 Indian Hill Rd, Winnetka, IL 60093
/35
$1,615,000

Sold May 29, 2026

841 Prospect Ave, Winnetka, IL 60093
- 5 Beds
- 3.5 Baths
- 2,478 Sq Ft
- Built 1899
Last Sold Summary
- 11% Above List Price
- $652/SF
- 5 Days On Market
Current Estimated Value $1,631,210

Last Listing Agent Christie Ascione @properties Christie's International Real Estate

841 Prospect Ave, Winnetka, IL 60093

/25
Est $500,271

Not Listed For Sale

778 Green Bay Rd, Winnetka, IL 60093
- 3 Beds
- 3 Baths
- 1,559 Sq Ft
- Built 1968
778 Green Bay Rd, Winnetka, IL 60093

Last Sold Summary
- 4 Days On Market
Last Listing Agent Joanne Hudson Compass

/41
$1,779,000

Pending
- 4 Beds
- 2.5 Baths
- 3,950 Sq Ft
639 Lincoln Ave, Winnetka, IL 60093

Nestled in an exceptional location, this beautifully appointed home offers the perfect combination of charm, comfort, and convenience. Just moments from vibrant downtown Winnetka, you'll enjoy easy access to outstanding restaurants, boutique shopping, the train station, and the beach-making it easy to embrace the very best of the community. Inside, the thoughtfully designed floor plan features

Anne Malone Engel & Voelkers Chicago North Shore

639 Lincoln Ave, Winnetka, IL 60093
/50
$2,050,000

Sold Aug 28, 2025

803 Pine St, Winnetka, IL 60093
- 4 Beds
- 4 Baths
- 4,460 Sq Ft
- Built 2022
Last Sold Summary
- 16% Below List Price
- $460/SF
- 320 Days On Market
Current Estimated Value $2,174,367

Last Listing Agent Michael Kelly Compass

803 Pine St, Winnetka, IL 60093

/63
Est $9,170,233

Not Listed For Sale

765 Sheridan Rd, Winnetka, IL 60093
- 7 Beds
- 8 Baths
- 15,784 Sq Ft
- Built 2005
765 Sheridan Rd, Winnetka, IL 60093

Last Sold Summary
- 8 Days On Market
Last Listing Agent Jena Radnay @properties Christie's International Real Estate

/48
$4,699,000

Pending
- 6 Beds
- 9 Baths
- 6,000 Sq Ft
231 Woodlawn Ave, Winnetka, IL 60093

Magnificent East Glencoe home- approximately 9,000 sf of total finished space. 6 BR all ensuite plus 3 additional half baths. Stone & brick exterior on over .5 acre lot. Close to train. Featuring a spectacular kitchen, media room, cherry library, workout room, sauna, wine cellar, and fully fenced expansive private outdoor living space with fireplace / TV and separate fire pit with seating area

Craig Stone Stone Realty Group

231 Woodlawn Ave, Winnetka, IL 60093
/45
$2,345,000

Sold Jul 15, 2026

1258 Scott Ave, Winnetka, IL 60093
- 5 Beds
- 5.5 Baths
- 3,426 Sq Ft
- Built 1979
Last Sold Summary
- 7% Above List Price
- $684/SF
- 3 Days On Market
Current Estimated Value $2,147,223

Last Listing Agent Sara Sullivan Compass

1258 Scott Ave, Winnetka, IL 60093

/46
Est $2,735,349

Not Listed For Sale

953 Spruce St, Winnetka, IL 60093
- 4 Beds
- 5.5 Baths
- 5,026 Sq Ft
- Built 2009
953 Spruce St, Winnetka, IL 60093

Last Sold Summary
- 10 Days On Market
Last Listing Agent Bonnie Tripton @properties Christie's International Real Estate

Showing Results 81 - 120, Page 3 of 18

Illinois Cook County

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Winnetka, IL Homes

Real Estate & Homes