151 Winnetka, IL Real Estate Listings

Sort by:
Open 5/9
$1,495,000Est. Payment
5 Beds | 4 Baths | 4,654 Sqft
140 Westview Road, Winnetka, IL 60093
House For Sale

A lush half-acre in Winnetka's most ideal location - walk to the award-winning Crow Island (K-4), Skokie (5/6), and Washburne (7/8) Schools. This 5 bedroom home has been completely and tastefully renovated with additions designed by Paul Konstant. With terrific curb appeal and a sought-after open floor plan, this home has formal living spaces which include a traditional living room with bay windows and fireplace, and a sun-lit dining room. A private first-floor office with custom cabinetry, wet bar, and fireplace overlooks the professionally landscaped yard. A new cook's kitchen with high-end appliances and generous quartz island along with breakfast/sitting area opens to the spacious family room and sizeable playroom with 3 walls of windows. A luxe first-floor primary suite with walk-in closet, new bathroom with marble countertops, walk-in shower, and bathtub. The impressive first-floor space includes a charming mudroom, sunny first-floor laundry, and storage room off the attached 2 car garage. The second floor includes a spacious suite with an en suite bath, 3 additional bedrooms that share an updated hall bath, and a separate office with built-in cabinetry. The unsurpassed outdoor living space includes a fenced-in yard, hardscaped patio, firepit, and bar. Meticulously maintained and move-in ready, 140 Westview offers a lifestyle that includes exceptional indoor and outdoor living space with a city chic/suburban flair.

$1,650,000Est. Payment
4 Beds | 4 Baths | 4,011 Sqft
1015 Starr Road, Winnetka, IL 60093
House For Sale

Amazing property located on the beautiful and private Starr Street. This architecturally significant home was designed by John Van Bergen, who worked with Frank Lloyd Wright. Work with the team of Award Winning builder and Award Winning architect to remodel this beautiful property. The listing price offers the property as is. The builder is open to work with your client's ideas. The additional remodeling cost will be based on the architectural plans developed by the buyer. Due to architectural significance, this property is eligible for real estate property tax freeze and 20% increase in the FAR allowance. The property is also available as a new construction project. The current price reflects the land value only. Builder is available to meet with your clients to discuss their wants and needs.

$2,275,000Est. Payment
5 Beds | 6 Baths | -- Sqft
175 De Windt Road, Winnetka, IL 60093
House For Sale

Privacy at it's best! Stately English home tucked away on one of Winnetka's most beautiful private roads with it's own gated entrance. This incredible sun filled home lives beautifully inside and outside! A grand reception hall with sweeping staircase welcomes you into the home boasting gorgeous detail throughout and a fabulous and flexible floorplan for entertaining on the main level. Large kitchen with breakfast area that overlooks the backyard and opens to the dining room which could also be a large family room off the kitchen. Two family living and gathering spaces could be used in various ways...you decide how you want to live in this incredible home. Close the doors to the handsome wood paneled office/library for a quiet space to relax in. The primary suite is an oasis...a sitting room/office with a fireplace, walk-in closet and beautiful bathroom. 3 other nice sized family bedrooms and a large laundry room on the 2nd level. Retreat to the spacious 3rd floor...a huge hangout room plus a 5th bedroom (ensuite) perfect for guests or live in childcare. 2-car attached garage with storage, mudroom and full bath on first floor. Looking for great outdoor space...enjoy the Chalet landscaped backyard, fully fenced in. Expansive bluestone patio with fire pit plus several seating areas...perfect for grilling, dining, & lounging! Perfect Winnetka location, walk to schools, town and the lake nearby. AN EXCEPTIONAL FAMILY HOME in every way!

$409,000Est. Payment
3 Beds | 3 Baths | -- Sqft
469 Linden Street, Winnetka, IL 60093
Townhouse For Sale

Rare opportunity! This fabulous 3 bedroom, 2.1 bath brick townhome offers care free living and convenient walk to everything in the heart of Winnetka! Significant owner improvements include renovated first level including new kitchen/appliances, new powder room, basement remodel with the addition of a 3rd bedroom, office area and full bath. You will love the light-filled end unit, exposed brick walls, hardwood floors, and tons of storage. The large living room features a wood burning fireplace with sliding glass doors leading to a private patio with gas grill and perennial garden. On the second level you will find 2 spacious bedrooms with great closets and a beautiful updated full bath. One parking spot is included with an option for additional parking and pets are allowed. Close to town, train, shops and restaurants. Simplified living at its best. Must see this very special home!

Open 5/8
$749,900Est. Payment
3 Beds | 3 Baths | -- Sqft
419 Provident Avenue, Winnetka, IL 60093
House For Sale

No Showings until Saturday the 8th. this beautiful remodel of a picture-perfect brick home in the coveted "tree streets". Oversized light-filled living room w/ fireplace that flows into the open concept white kitchen with large island and dining area. Attached family room den with french doors to large paver brick patio. Master bedroom with attached remodeled bath and two additional bedrooms and remodeled hall bath on the 2nd floor. Unfinished LL is a blank slate ready to be customized w/ storage, play area, and laundry. Deep yard with great patio and a newer 2 car garage.

$1,075,000Est. Payment
4 Beds | 3 Baths | -- Sqft
888 Cherry Street, Winnetka, IL 60093
House For Sale

Step into this picture perfect Cape Cod charmer with front porch just 2 blocks from town and train in popular "Tree Street" location. Open floor plan features a sun filled double entry that opens to the beautiful living room with fireplace with gas logs, hardwood floors, and loads of windows. Formal dining room is open to living room. A fabulous large scale white & stainless steel kitchen awaits you with cook top island, greenhouse window, and separate breakfast room. Best part of this kitchen is it's open to the family room with second beautiful fireplace and sliding doors to a great raised deck with full view of the expansive back lawn. Ideally located first floor laundry room and powder room are just off the kitchen. Skylight second floor hall opens to large scale skylight primary suite w/walk in closet, skylight updated bath with his & hers sinks. Three family bedrooms all good scaled and a white update hall bath complete the 2nd floor. Finished Rec room or "Zoom" study room in lower level as well as huge storage/playroom. Fenced in back yard is huge, owner even set up hockey rink during winter, and a long driveway to 2 car garage.

$525,000Est. Payment
2 Beds | 2 Baths | 1,218 Sqft
972 Tower Road, Winnetka, IL 60093
House For Sale


$699,000Est. Payment
3 Beds | 3 Baths | 2,471 Sqft
550 Happ Road, Northfield, IL 60093
House For Sale

This lovely, 2-story home on just under a 1/2 acre of beautifully landscaped yard, boasts 7 spacious rooms including 3 bedrooms and 2 1/2 bathrooms. Features include newly finished hardwood floors throughout, 3 fireplaces, and large light-filled windows. The living room boasts a huge picture window and built-in bookshelves that frame either side of the wood-burning fireplace. Opening off the living room is the dining room which in turn opens on to a family room surrounded by windows, a vaulted ceiling, a second fireplace, and a bay window with a built-in seating area. A sliding door opens from the family room onto a brick paver patio surrounded by the garden. Enjoy the kitchen with its sunny eating area, newly painted cabinets, quartz countertops, and separate pantry. The second-floor master bedroom with bath features 2 closets, one of which is a walk-in. A hall bath and 2 additional bedrooms complete the second floor. The basement is partially finished with a rec room and 3rd fireplace while the rest of the basement includes a laundry/utility and storage area. The yard is truly fabulous with beautiful perennial gardens and shed. All this, and close to town, parks, and award-winning schools including New Trier High School, Middlefork Primary, and state of the art, Sunset Ridge Middle School. Please note that some pictures have been virtually staged.

$1,199,000Est. Payment
4 Beds | 5 Baths | 2,984 Sqft
74 Brier Street, Winnetka, IL 60093
House For Sale

This home is located at 74 Brier Street Winnetka, IL 60093 US and has been listed on Homes.com since 29 April 2021 and is currently priced at $1,199,000, approximately $402 per square foot. This property was built in 2017. 74 Brier Street is within the school district(s) Kenilworth School District 38 and New Trier Township High School District 203 with nearby schools including The Joseph Sears School and New Trier Township High School Winnetka Campus. Similar properties nearby are <a href="/property/1240-sunset-rd-winnetka-il-60093/id-600013482625/">1240 Sunset Rd</a>, <a href="/property/428-beverly-dr-wilmette-il-60091/id-600013055049/">428 Beverly Dr</a>, <a href="/property/609-ivy-ct-kenilworth-il-60043/id-600013429066/">609 Ivy Ct</a>, <a href="/property/74-brier-st-winnetka-il-60093/id-600012834279/">74 Brier St</a>, <a href="/property/1190-oakley-ave-winnetka-il-60093/id-600012832824/">1190 Oakley Ave</a>, <a href="/property/2711-eastwood-ave-evanston-il-60201/id-600013348475/">2711 Eastwood Ave</a>, <a href="/property/9560-drake-ave-evanston-il-60203/id-600012879674/">9560 Drake Ave</a>, <a href="/property/516-meadow-rd-winnetka-il-60093/id-600013378064/">516 Meadow Rd</a>, <a href="/property/835-lake-ave-wilmette-il-60091/id-600013067860/">835 Lake Ave</a>, and <a href="/property/2755-reese-ave-evanston-il-60201/id-600012836747/">2755 Reese Ave</a>.

$430,000Est. Payment
0.19 Acres
724 Foxdale Avenue, Winnetka, IL 60093
Lots Land For Sale

BUILD NEW IN EAST WINNETKA! 70Ft Frontage. Enjoy a great walk to everything location - both downtown Winnetka and Hubbard Woods- two Metra stations, an abundance of restaurants and shopping, beaches, parks and boat launches. A great opportunity for new construction on a lovely street!

$3,625,000Est. Payment
4 Beds | 5 Baths | 7,046 Sqft
71 Indian Hill Road, Winnetka, IL 60093
House For Sale

This ranch style contemporary French home, boasting one of Winnetka's most prestigious addresses, is a one of a kind work of art! Designed by Norman Yeretsky and built in 1974, this 7000+ square foot home is situated on 1.18 acres facing the 12th green of Indian Hill Country Club. The sun-drenched foyer/gallery with terrazzo floors and a wall of windows overlooking the pool leads to a dramatic living room with impressive 14' beamed ceilings, ornamental moldings, hardwood floors, an antique French marble mantle over the gas log fireplace and truly stunning views of the golf course. The living room leads to a huge step-down garden/dining room with high vaulted ceilings, a skylight, exposed brick and terrazzo floors. The fully equipped kitchen has an eat-in area and tons of cabinets plus an oversized walk-in pantry. Off the dining room is a small, intimate gathering space and a tiled wet bar with sub-zero ice maker and built-in wine refrigerator. The den between the bar area and the family room lends itself to a number of uses, including in-home office, at-home learning, playroom or casual sitting room. The enormous family room overlooks the pool and backyard. A fourth bedroom, in this wing, has a private exterior entrance and a full, updated bathroom. While currently used as a game room, it was originally a two-room suite designed for live-in's and could easily be converted back to this configuration making it great for multi-generational living, a home office, or you name it. The other three bedrooms are on the opposite side of the home. Enter the main bedroom wing through beautiful French architectural doors just off the foyer. First, pass the black and white granite powder room with architectural detailing. The primary bedroom suite is a giant octagonal bedroom with an antique marble mantle over a gas logged fireplace and is flanked by two separate private spaces. One side includes a study/dressing room with floor to ceiling shelves, a walk-in closet, built-ins and a private bathroom. The other side has a lovely sitting room/dressing room, built-in window seats, a walk-in closet, floor to ceiling shelves and drawers, a built-in dressing table, a marble bathtub, and a walk-in shower. Two more generous bedrooms are down the hall as well as a shared bath and access to the pool area. The backyard includes a massive blue patio for social gatherings as well as a pool with a diving board and a slide. The home has a three-car attached and heated garage complete with extra cabinet storage. The paver driveway has plenty of parking for guests. This home is in Harper Elementary and award-winning Wilmette District 39. This home is perfect for so many buyers and is like living in a resort every day.

$585,900Est. Payment
4 Beds | 2 Baths | 2,528 Sqft
856 Foxdale Avenue, Winnetka, IL 60093
House For Sale

Bright, Open Concept, Spacious 2500 sf Arts and Crafts Home, Full of Character and Beautiful Woodwork in Desirable Park-Like Setting in Winnetka. You will enjoy this wonderful historic home built by Arthur Rudolph in 1923. Fabulous Architectural features including dormers, cedar-shake roof, arched walkways, coved ceilings, oak pillars and huge sun porch on one full side of the home. Main Level featuring Open Concept Living Space accented by Arched doorways to Huge Sunporch with 3 walls of windows where light spills in everywhere! Family Room with coved ceiling where you can overlook beautiful mature yard with oak trees. Dining Room boasts Large 3-part Window. Country Kitchen with Maple flooring. Upper level hallways offer hardwood flooring. Large bedrooms with plenty of closet space including built in cabinets in hallway closets. 4th bedrooms makes a perfect nursery with heater and closet. Main Upper Level Bath has ceramic tile flooring, Jacuzzi tub, pedestal sink and matching fixtures. Master Suite is the ideal place to watch the sunrise and set with windows on 3 sides. Master Suite has 2 large his/hers closets. Quality hardwood flooring throughout most of the home. Living Dining and Family Rooms featuring Oak Hardwood. Kitchen featuring Maple Hardwood. Kitchen has room for expansion and your creativity for some updating. All Bedrooms have hardwood. Large unfinished English walk-out basement with high ceilings. Large 2.5 Car Garage with 2nd Story with window, ideal for storage. Beautiful yard with mature oaks in this park-like atmosphere. Quiet street with home set in just the right place to create a very private backyard where nature abounds. Radiator heat throughout is so quiet and moist. Upgraded electrical including basement. Spacious Room Sizes: Living Room: 22 x 17 Dining Room: 12 x 12 Kitchen 9 x 12 Family Room; 17 x 17 Mudroom: 9 x 12 Main Floor Bath: 7 x 10 Master bedroom: 17 x 30 Second Bedroom:12 x 13 Third Bedroom: 12 x 13 Fourth Bedroom: 9 x 11 Lot

$1,100,000Est. Payment
4 Beds | 4 Baths | 3,532 Sqft
429 Linden St, Winnetka, IL 60093
House For Sale

Unique intown charmer, this home has it all! Designed by a noted North Shore architect, it is a truly striking blend of architectural style in perfect harmony with its surroundings. Situated in the heart of Winnetka, this home combines the best of city style with the comforts of suburban living. Volume ceilings in the Living Room, Dining Room, Breakfast Room, and Family Room, accented by a round Clerestory window. Exquisite first floor Master Suite completes the first floor. Nine Velux electronically operated skylights. Second floor has two bedrooms with baths and an optional 4th bedroom which is open to first floor. Second floor deck with lattice privacy screen. Finished basement with nine foot ceilings. Beautifully landscaped yard to enjoy warm summer nights! So many stunning details, you need to see to believe. This is a very special home just waiting for your family. A jewel!

$460,000Est. Payment
3 Beds | 2 Baths | -- Sqft
258 Churchill Street, Northfield, IL 60093
House For Sale

An idyllic ranch-style home located on a quiet, tree-lined cul-de-sac. This Northfield charmer features 3 generously sized bedrooms, 2 baths and a dedicated office space. Walk in to the spacious living/dining room connected to the open-concept kitchen. Enjoy the sun-filled dining room with large bay windows and a wood burning fireplace. The large patio and private backyard are the perfect oasis for entertaining or relaxing on a warm summer day. Located within 2 award-winning schools: New Trier High School and the newly built Sunset Ridge school. Walking distance to the newly built bandstand, renovated Clarkson Park playground, shopping, farmer's market, and everything Northfield has to offer.

$825,000Est. Payment
1.4 Acres
2180 Old Willow Road, Northfield, IL 60093
Lots Land For Sale

Outstanding opportunity to build your dream home on this 1.4 acres with 175" frontage on the new desirable strip of Old Willow Road with luxury new constructions homes. $40,000 of tree removal was already done as well as an entire wall of tall Arborvitaes on the back of the lot for privacy. Walking distance to Middlefork Primary and Sunset Ridge Schools. A. Perry Homes can provide a one stop solution to design and build your dream home. Renderings are in the pictures.

$3,945,000Est. Payment
4 Beds | 5 Baths | 5,600 Sqft
16 Longmeadow Road, Winnetka, IL 60093
House For Sale

Cohesively designed to be a natural peaceful oasis with a "zen" aura from inside to out, this masterful Tony Grunsfeld classic modern ranch radiates to a whole new level of designer perfection after a very extensive 2 year rebuild from the ground up. Intricate attention was given to every element of this home from the custom entrance reflection pond with basalt columns from Seattle that signals peace and balance to the exterior Colorado stone that seamlessly blends in with nature to the hand picked cedar planked accent ceiling with in-grove lighting to highlight warmth. This sanctuary set on an exquisitely manicured 1 acre lot allows nature to shine in through all 75 new Architectural Series Pella floor to ceiling windows. A welcoming atrium reception hallway sets the tone of this masterpiece with the original Borgini Gold Calcutta marble floors restored to their grand beauty with a custom honed soft sheen. Light fills the space through the custom atrium skylights to depict endless space from inside to outside and night custom LED linear lighting leads the way to the stars. State of the Art Chef's kitchen is highlighted with one of kind pendant lighting with Carrera marble accents with a waterfall oversized honed grey quartz island. Sleek yet formal dining room overlooks the family room area separated by a white oak built-in buffet table with a Iceberg Quartz waterfall lit countertop. Beautiful breakfast alcove w/ access to the extensive bluestone patio & outdoor kitchen featuring quartz counters and Wolf grill. Tranquil primary suite w/ gas-burning fireplace & serene private patio is the perfect space to unwind for the day with an equally as luxurious bath with custom double vanity w/ black veined quartz countertop, Ann Sacks tile, heated floors, walk-in steam shower, and Victoria Albert custom colored charcoal soaking tub. Three additional bedrooms all with outdoor spaces allow one to escape to their own private getaway place. Sleek newly engineered lower level

$1,000,000Est. Payment
3 Beds | 3 Baths | 2,120 Sqft
2040 Suffork Road, Northfield, IL 60093
House For Sale

NO SIGN! LOCATION, LOCATION, LOCATION! Stunning, Spacious 9 Rooms, light-filled & updated Quad Level with Vaulted ceilings, Gleaming hardwood floors throughout the main level. Fabulous open floor windows galore with view of lush landscaped 1.1 acres. Spacious gourmet kitchen with top-of-the-line appliances, including large Viking stove with 2 ovens. Kitchen island w/second sink and seating plus extra room for a table or sitting area. Living/dining room with lots of windows that allow for a great view of the spectacular yard. Large master suite with walk-in closet & spacious bath with separate shower and tub. Two additional bedrooms and a full bath complete 2nd the second level. Spacious family room that opens out to the incredible fenced-in yard that is perfect for outdoor play. Large finished recreation room, office, spacious laundry room and storage are all on the lower level. Attached 2 car garage and second one in the backyard. Award-winning District 29, Middlefork, state-of-the-art Sunset Ridge feeds into New Trier High School. A must-see!

version="1.1" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink" width="30px" height="24px" >