152 Houses For Sale in Winnetka, IL

Sort by:
Est. Payment$849,000
4 Beds | 3 Baths | 2,945 Sqft

1180 Oakley Ave, Winnetka, IL 60093

House For Sale

An incredible value on an incredible street. If you're looking for a rewarding project, this is a wonderful opportunity to update and/or expand a historic home in Hubbard Woods. This magnificent 4 bedroom, 2.5 bath property has great bones and exudes charm, class, and echoes of a bygone era. Built in 1919, the 2,965 appx square foot home features 10-foot ceilings on the 1st floor, hardwood floors throughout, large bedrooms, floor-to-ceiling windows in the living room and dining room and sits on the largest lot on the street (appx .39 acres). Steps from downtown Hubbard Woods, Metra station, schools, parks. Don't miss this rare opportunity to purchase a historic gem on Oakley Avenue, one of Winnetka's most desirable streets. For more information on this property, contact the listing agent, Lyon Folker Campbell Partners at (847) 504-6182 or [email protected]

Est. Payment$899,000
4 Beds | 4 Baths | 3,620 Sqft

746 Foxdale Avenue, Winnetka, IL 60093

House For Sale

Oversized lot in desirable east Winnetka & Greeley Elementary. 100 foot frontage with attached two car garage. Ideally situated within walking distance to downtown Winnetka & Hubbard Woods, Metra & Tower beach. Exceptionally well maintained home with tons of space. Many updates including new roof, siding, gutters, boiler, water heater, & kitchen appliances (see spec sheet in additional documents). The spacious family room addition features high ceilings, skylights, fireplace & built in shelving and is located immediately adjacent to the kitchen & breakfast area - the perfect footprint for a massive great room. The home also features separate formal living & dining rooms as well as an all season sun room that could be used as second media or playroom. Four bedrooms & two baths on the second level. Master bedroom features ensuite bath & walk in closets. Newly painted and carpeted basement rec room. The unfinished basement has great ceiling height and tons of additional space that is just waiting to be finished. Large fenced backyard with deck. Adjacent to the Greenbay walking/biking/running trail. Terrific house in an amazing location - bonus feature - best block party in Winnetka!

Est. Payment$1,025,000
3 Beds | 3 Baths | 5,106 Sqft

128 Church Road, Winnetka, IL 60093

House For Sale

Stunning Mediterranean style home surrounded by almost half an acre of lush grounds! Inviting first floor features exactly what today's buyer is looking for: newer, eat in white kitchen overlooking family room with fireplace and first floor laundry with mud room entry! Rounding out the first floor are formal living and dining rooms, a charming sunroom and a screened in porch. Oversized patio makes the perfect backyard retreat! Master suite with room for office or attached nursery, walk in closet, and dual vanity bath. Two additional generously sized bedrooms share hall. bath. Finished basement and newer garage. Foot path into Indian Hill Road for scooter & bike rides - walk to Indian Hill train station & park!


Michele Millan

Est. Payment$875,000
4 Beds | 4 Baths | 2,547 Sqft

1116 Tower Road, Winnetka, IL 60093

House For Sale

A beautiful Keck Tudor with modern design elements, nestled on a pretty tree-lined street in Hubbard Woods. Built-ins and a wood burning fireplace lend a whisper of cottage charm to this spacious and updated home. Made for entertaining, a large island that seats 6, is at the heart of an updated white kitchen with clean lines, overlooking the family room with 1/2 bath. French doors lead to a bluestone & brick patio extending the living space to a lovely private backyard with mature trees and foliage offering great views. The 2nd level features two spacious ensuite bedrooms, 2 additional bedrooms, a 3rd full bath, and an office/5th bedroom. Pull down stairs to a 3rd floor attic with vaulted ceiling offers possible expansion and ample storage. The lower level has a recreation area, pantry/storage and laundry room. There is an attached 1 car garage being used as a workshop and a detached 1.5 garage off the driveway. New back steps, rear fence, washer & dryer, newer hot water heater, chimney & exterior paint. Close to town, schools & train and easy access to the lakefront, Greenbay Bike Trail, Skokie Lagoons and Forest Preserve trail.

Est. Payment$539,000
4 Beds | 3 Baths | 2,432 Sqft

1857 Winnetka Road, Northfield, IL 60093

House For Sale

SPACE TO MOVE! BIKE, WALK, DINE, EXPLORE! Delightful home in Northfield! Updated and move-in ready, this house boasts a wonderful floor plan with a new master bath, refinished hardwood floors, freshly painted rooms and new light fixtures giving it an inviting feel. Family room addition with wood burning fireplace and built-in cabinetry overlooks a blue stone patio and lovely yard. Master Bedroom with beautiful new marble master bath plus three additional bedrooms and shared bathroom on the second floor. Incredible opportunity with full-unfinished basement! Northfield is home to award winning Sunset Ridge school which has just been rebuilt. Just blocks away from shopping, dining, schools, and across from the forest preserve. Incredible opportunity to expand your horizons!

Est. Payment$1,375,000
6 Beds | 5 Baths | -- Sqft

315 Sunset Road, Winnetka, IL 60093

House For Sale

Dining al fresco will be a dream on your exquisite Terrace that offers spectacular panoramic vistas of the gorgeous gardens and lushly landscaped .4 of an acre in East Winnetka. Relax and hear the waves lapse against the shores of Lake Michigan at Elder Beach and Elder Park, which are just around the corner. It's all about a lifestyle here. This lovely home is perfect for entertaining as well as family living on its 4 levels of living space with fresh, neutral decor. Five beautiful French doors in the grand formal Living Room and Dining Room with gleaming hardwood floors open out onto the terrace. The spacious DeGuilio kitchen with gourmet culinary appliances will make cooking meals a breeze for the chef in your family. Enjoy casual meals at the island with room for 4 stools or at the large table area in the Breakfast area, which also has a planning desk. Step into the jaw dropping, architecturally stunning Family Room, which features built ins, a wet bar and French doors accessing both the upper Terrace and lower Patio. Take in views of sunsets as well as the Sunset Road parkway, which is enjoyed by neighbors as additional recreational space, from the charming Sunroom, which features a tile floor, built ins, and 3 sides of light from oversized windows. Head upstairs and you will find the Master Suite, which has a Sitting Room/Dressing Room accessing the luxurious Master Bath, which features an oversized double vanity and Steam Shower. 2 Additional Family BR's access a bright and sunny Tandem Room, perfect as a playroom or office. A hall BA completes the 2nd Fl. The 3rd Floor features 3 Bedrooms with tree top views and a Hall BA. A spacious Recreation Room with bar, 2 large storage rooms, a Laundry/ Utility Room and a full BA complete the Lower Level. The location is phenomenal.... 315 Sunset is located on a quiet cul de sac with a parkway. In addition to the lake around the corner, New Trier HS (grades 10-12) and Greeley School (JK-4) are within 2 blocks.

Est. Payment$473,000
3 Beds | 3 Baths | 1,840 Sqft

370 Winnetka Avenue, Winnetka, IL 60093

House For Sale

Appealing, much-loved 3 bedroom/2.5 bath East Coast Colonial across from the front door of New Trier High School ... great commute for teens! Spacious Living Room features handsome fireplace (as is), French doors and hardwood flooring under carpet. Charming Dining Room has 2 corner cupboards + pretty view of patio & deep backyard. Family Room is a comfortable size and perfect for TV or Office. Second floor with 3 Bedrooms and 2 full baths. Useful Basement with Storage Room and Laundry. Superb, convenient location in East Winnetka: tennis courts and big field across the street; one block to train, playground & outdoor ice rink; 2 blocks to lake; 3 blocks to award-winning Sears School in Kenilworth (nursery thru 8th grades). Just a short walk to several terrific restaurants, too. Great combo of Kenilworth schools & Winnetka Park District. Bring your ideas -- ready for renewal!

Est. Payment$1,175,000
6 Beds | 5 Baths | 4,917 Sqft

1124 Merrill Street, Winnetka, IL 60093

House For Sale

Modern and sizeable true six bedroom brick house with full finished basement with plenty of free flowing living space for comfort and hosting. Location, Location, Location in the heart of Hubbard Woods. Leave the car at home and enjoy the very close proximity of restaurants, shops, parks, tower beach and the Metra. Firstfloor en-suite bedroom for short term visitors and or long term guests. Five bedrooms second level including spacious master suite and 2 additional full baths. Open and contemporary kitchen with a recent upgrade in appliances. Two story foyer upon entry. Oversized mud room and crown molding throughout. Possible seventh bedroom in finished basement which includes full bathroom, tall ceilings, wet bar, additional laundry, and plenty of space for play/exercise. Brick paver patio and green space in the rear for warmer weather enjoyment. Roof recently replaced.

Est. Payment$1,889,000
5 Beds | 6 Baths | 5,256 Sqft

989 Oak Street, Winnetka, IL 60093

House For Sale

Enjoy your summer in this fabulous home with great open floor plan featuring gorgeous white chef's kitchen w/lg island and breatkfast area opening to sunlit family room. Fabulous DR and LR plus private Library. Stunning master suite w/ 2 walk-in closets and luxurious master bath. Three additional bdrms, two additional full baths and laundry room complete 2nd level. 3rd level with full bath and lg bedroom. Basement with Recreation room with wet bar and fireplace, exercise room and 6th bdrm and full bath. Many designer updates and finishes throughout home. Scott Byron landscaping. Lovely patio, private hot tub in rear yard, fenced yard, 2 car garage. NEST home system. Close to town, transportation, parks and schools. Exceptional home - truly turn key!

Est. Payment$1,150,000
5 Beds | -- Baths | -- Sqft

3 Longmeadow Road, Winnetka, IL 60093

House For Sale

Nearly one acre located on desirable Longmeadow Road in Winnetka. This fabulous property is an excellent opportunity to renovate, expand or design a new construction home and is NOT in a flood plain. This location and property is rare with surrounding expansive lots sizes and the quiet winding street. Create your dream home on this exceptional lot and stunning location. A gracious foyer welcomes you into this 5 bedroom, 4.1 bath home with a grand living room and over-sized bay window overlooking the expansive rear yard. The formal dining room is highlighted with custom built in storage leads to the sunlit spacious family room. Enjoy a special wood paneled office with built in bookshelves and fireplace.The eat in kitchen has a butcher clock island and butler's pantry plus laundry /mud room area and attached 2 car garage. Simplified living at its best with the first floor master bedroom retreat, private bathroom, his and hers closets plus two additional bedrooms on this level each with with en-suite baths. On the second level you will find two wood beamed bedrooms and a Jack and Jill bath on the second level. A huge basement includes a recreation room and storage galore! This home is sold "AS IS" and can be transformed as you wish. This rare property is gorgeous with a lovely stone patio, an abundance of mature landscaping and privacy. Wilmette schools and New Trier High School with amenities in Northfield township. Close to transportation, parks, schools, and more! This unique property is a must see! Easy to Show at Anytime! FaceTime, Zoom or in person showings available at your convenience.

Betsy Burke

Est. Payment$868,000
4 Beds | 3 Baths | 2,556 Sqft

1004 Spruce St, Winnetka, IL 60093

House For Sale

Classic good looks, impeccable updating, and careful maintenance on a wonderfully-landscaped corner lot in one of Winnetka's most popular neighborhoods - this very special 4 bedroom, 3 bath home checks all the boxes! Charming curb appeal is introduced by a generous covered front porch. The main floor boasts spacious living and dining rooms. The living room is big and divided into 2 inviting groupings, one in front of the cozy fireplace and the other soaking up sunlight from 3 large windows. The dining room entertains perfectly and could easily accommodate 12 or more guests. The kitchen is well-designed with warm wood cabinetry, granite counters, stainless appliances, great prep spaces, and loads of storage. It opens into a sun-filled family room complete with handsome built-ins, a casual dining table and access to both the back yard and a lovely private deck. 4th bedroom is located on the main floor with an adjacent full bath and is currently used as an office. The 2nd floor is flooded with brightness from large skylights, the top landing is loft-like and would work easily as a homework or reading space. The master bedroom suite is perfect, a wonderful size, a great walk-in closet, a gorgeous new bath and French doors to a large 2nd-story deck. The 2 family bedrooms are nicely sized with good closets and share the newly updated hall bath. There is also a washer and dryer on the 2nd. The basement is full-sized with two nicely finished rooms, one used as a playroom/rec room and the other as an office/exercise space. Additionally, there is a laundry/utility room and 2 storage areas. Outdoors there is a detached 2-car garage (2001), professional landscape, and lovely perennial gardens. The location is ideal - walking distance to town, train, all 3 schools, and Skokie Playfields. For more information on this property, contact the listing agent, Betsy Burke at (847) 565-4264 or [email protected]

Est. Payment$950,000
5 Beds | 4 Baths | 4,126 Sqft

2130 Old Willow Road, Northfield, IL 60093

House For Sale

NEED SPACE? Surprises await inside this spectacular sprawling ranch with over 4,100 sq ft of living space on the first level plus a huge partially finished basement with additional living, working and storage space galore! With a newly updated interior in the heart of Northfield, this is the house you've been waiting for! No busy streets to cross! Short walk to get to the highly rated Northfield Schools, shopping, dining and more! Spoil yourself in the expansive kitchen/great room fashioned with 2 subzero refrigerators, one with 2 zone wine storage, a Wolf induction stovetop, double Wolf ovens, Bosch dishwasher, a walk-in pantry and a huge island with seating for everyone! This home boasts huge rooms with tons of living space including a great room off the kitchen, a living room and a fantastic 4 season sun room overlooking the expansive yard and pool. The master suite is a personal retreat with a huge walk-in closet and a new master bathroom with a spa tub, steam shower and double bowl sinks. Other highlights include a wonderful mudroom with laundry and a full bathroom, a 3 car attached garage with electric car charging station, a heated Koi pond, and a new roof recently installed. Easy to show virtually and in person!

Est. Payment$1,475,000
4 Beds | -- Baths | 3,542 Sqft

145 Sheridan Road, Winnetka, IL 60093

House For Sale

"Fresh, Simple Elegance" epitomizes the stunning gut renovation of this East Winnetka gem within a stone's throw of the lake, town and train. Artfully designed at every turn, this 4BR/4BA home with rare first floor Master suite boasts a beautiful, fresh "Coastal" aesthetic that celebrates the fusion of high design with a relaxed comfort that brings tranquility to every room. No detail overlooked. The circular floor plan allows each room to flow effortlessly into the next while creating the perfect balance of privacy and space. The front foyer draws you into a breathtaking open living space with beautiful French doors, fireplace and floor-to-ceiling windows that bring the serenity of the outside in from almost every angle. The living/dining room transitions into a spectacular family/sunroom that exudes of stylish comfort with stunning views of the backyard and access to the lovely new paver patio. The jaw-dropping Chef's kitchen is truly one-of-a kind. Gorgeous custom cabinetry, quartz countertops, top-of-the-line appliances and a fabulous, oversized island -- as perfect for a cozy cup of coffee as an entertainment spread like you've never seen. Large, bright laundry room, mudroom and access to heated 2-car garage all located off of kitchen. The first floor also features a large office with custom built-ins and beautiful bay window. A spectacular Master bedroom retreat with elegant custom millwork, European spa bath with radiant floor heat and walk-in-closet, along with 2nd bedroom and exquisitely designed full hall bath complete the first floor. The 2nd floor features two spacious, sun-filled bedrooms each with double closets, ensuite baths and views of the garden. The fully floored attic is accessed off of the 4th bedroom and offers a tremendous amount of storage or turnkey opportunity to finish for additional living space. 145 N. Sheridan is truly a special home... the simple, clean lines and nod to the natural world offer a moment of calm and breath of fresh air.

Est. Payment$4,999,000
6 Beds | -- Baths | 8,800 Sqft

27 Indian Hill Road, Winnetka, IL 60093

House For Sale

This home is located at 27 Indian Hill Road Winnetka, IL 60093 US and has been listed on Homes.com since 17 May 2020 and is currently priced at $4,999,000, approximately $568 per square foot. This property was built in 2005. 27 Indian Hill Road is within the school district(s) Avoca School District 37 and New Trier Township High School District 203 with nearby schools including Avoca West Elementary School, Marie Murphy School, and New Trier Township High School Winnetka Campus. Similar properties nearby are <a href="/property/13-woodley-rd-winnetka-il-60093/id-600030695986/">13 Woodley Rd</a>, <a href="/property/15-woodley-rd-winnetka-il-60093/id-600012834748/">15 Woodley Rd</a>, <a href="/property/187-hazel-ave-glencoe-il-60022/id-600013006993/">187 Hazel Ave</a>, <a href="/property/219-sheridan-rd-kenilworth-il-60043/id-600013170665/">219 Sheridan Rd</a>, <a href="/property/27-indian-hill-rd-winnetka-il-60093/id-600012834964/">27 Indian Hill Rd</a>, <a href="/property/434-greenleaf-ave-glencoe-il-60022/id-600013477451/">434 Greenleaf Ave</a>, and <a href="/property/2-bristol-rd-winnetka-il-60093/id-600013484149/">2 Bristol Rd</a>.

Est. Payment$975,000
5 Beds | -- Baths | 3,276 Sqft

1220 Sunset Road, Winnetka, IL 60093

House For Sale

Located within the Friend Rose subdivision, this picturesque, center entry Colonial is situated at the end of the peacefully quiet, cul de sac. You are welcomed into the home through double entry doors into a spacious foyer flanked by the sizeable living room and formal dining room, complete with traditional moldings. The fully renovated kitchen includes quartz counter tops, new hardwood floors and double ovens. The family room with wet bar and wood burning fireplace and mudroom/laundry room complete the first floor. The second level has five bedrooms, including the master suite and two additional full baths. The finished basement has designated storage, office space, kitchenette and full bath, featuring a steam shower. The 2.5 car attached garage allows plenty of space for two car plus additional storage. The traditional elegance and styling of today's modern buyer make this home a must see!

Est. Payment$1,145,000
5 Beds | -- Baths | -- Sqft

830 Heather Lane, Winnetka, IL 60093

House For Sale

VERY EASY TO SHOW and priced to SELL! A RARE Winnetka offering.....this comfortable and polished home is all about lifestyle living. Set in a quiet cul-de-sac on over half an acre, this retreat overlooks a small pond and the forest preserve. The entire experience provides a feeling of tranquility, that is hard to find. Finished in a beautiful, neutral palate, this special home exudes refined luxury with exceptional custom finishes and has an ideal floor-plan that includes everything you are looking for...two fireplaces, hardwood floors and large windows offering picturesque views. Light-filled rooms with excellent flow lend themselves to dining and entertaining including a beautiful living room and dining room, both with fireplaces, a family room and bright sunroom, all with floor to ceiling windows. The expansive first floor has a separate wing with an updated master suite, walk-in closet, and a newly renovated bathroom. Completing the main level is an additional full bath, his and her offices, a galley kitchen and eating area, and a laundry/mud room attached to a two-car garage. The second level includes 4 spacious bedrooms, all with incredible views, and 2 full baths. The lower level completes the home with a large recreation/playroom, a fantastic & fun, easy to maintain indoor pool with two full baths/locker rooms, and plenty of storage space. The pool area attaches to an outside grotto perfect for a hot tub and leads to an expansive backyard and a custom bluestone patio that is perfect for hosting family and friends all summer. The outdoor space is truly an idyllic oasis. This is a unique opportunity not to be missed!

Est. Payment$1,399,125
5 Beds | -- Baths | 5,000 Sqft

922 Cherry Street, Winnetka, IL 60093

House For Sale

Masterfully built, French inspired brick & limestone home combines exceptional, high-end finishes with fabulous floor plan designed for both daily living and entertainment. Step inside to a dramatic 2 story foyer with spiral staircase and flowing first floor that features a private living room with fireplace, a gracious dining room and a spacious Chef's kitchen with butler pantry and built-in breakfast area that overlooks paver patio and professionally landscaped backyard. The kitchen opens into a sun-drenched family room with beautiful French doors, custom built-ins and a stunning stone fireplace. Second floor features a lovely, open landing and tranquil private master suite w/balcony, spa bath and generous walk-in closet. 2 additional bedrooms with Jack & Jill bath and large laundry room complete the 2nd floor. Follow the spiral staircase to a fantastic third floor guest suite with full bath and walk-out attic space. Lower level features a handsome office w/gas fireplace, large recreation room, and additional bedroom w/full bath. No detail is overlooked in this exquisite home... just blocks from downtown Winnetka, the train, parks and schools! This one is not to be missed! 3D VIRTUAL TOUR AVAILABLE.

list-24px Created with Sketch. width="24" height="24" viewBox="0 0 24 24" version="1.2" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink" overflow="visible" preserveAspectRatio="none" > version="1.1" xmlns="http://www.w3.org/2000/svg" xmlns:xlink="http://www.w3.org/1999/xlink" width="30px" height="24px" >