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107 Houses For Sale in Winnetka, IL

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New
$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.

New
$225,000Est. Payment
2 Beds | 1 Bath | 955 Sqft
173 Happ Road, Northfield, IL 60093
House For Sale

Investor, Rehabber, Fixer Upper Or Developer! Perfect Opportunity For Having A Remodelled Or Rebuilt Home in Northfield. Close To Schools, Shopping and Transportation. New Trier District. Build Your Dream House and Enjoy The Neighborhood As Well.

New
$2,735,000Est. Payment
6 Beds | 5 Baths | 6,820 Sqft
744 Prospect Avenue, Winnetka, IL 60093
House For Sale

The essence of Winnetka is beautifully captured within this timeless, stately brick Georgian, located in the best East "nook" with winding roads and lake breezes. Majestic in its own right with a curved custom carved rotunda centers the elegance throughout 3 floors of captivating living spaces full of character. Gracious corner lot with mature privacy landscaping with pool & bonus 1 bed coach house over the 3 car garage. Sweeping reception hall with a grand staircase, finely carved moldings & custom swing French doors allow southern exposure light to shine on lush grounds. Light filled sun/family room with custom builtins, stunning arched floor to ceilings windows, and French doors create a unique space. Stately French glass doors open to the oversized living room with a prominent fireplace surrounded by custom bookshelves, and alcove window allowing light to flow in seamlessly. Graceful formal dining room w/ detailed wainscoting and stunning windows opens to the DeGiulio chef's kitchen highlighted with maple praline cabinetry, large island w/ breakfast bar seating, top of the line appliances, and separate sunny breakfast area. Step out French doors to a wrap around patio overlooking the pool. Spacious mudroom with custom cabinetry and powder room finish off this level. Wide prominent staircase to the 2nd level with a stunning primary suite w/ a beautifully built-out walkthrough closet & dressing room surrounded by mirrored closets, and dual separate white marble baths. The primary bedroom mirrors the beautiful sunroom windows as it is located in the rotunda, creating a sunny relaxing private oasis. 2 additional family bedrooms to the other side of the second level share jack and jill bath. Fully finished 3rd level has 2 additional bedrooms w/ full bath, and recreation room. Unfinished LL with great storage, laundry could be built out for play/game room. Three car garage w updated coach house makes perfect guest quarters w/ living room, bedroom, bath and kitchen

New
$5,499,000Est. Payment
7 Beds | 10 Baths | -- Sqft
115 De Windt Road, Winnetka, IL 60093
House For Sale

A rare and prestigious opportunity to own one of Winnetka's most iconic estates; 115 De Windt is timeless elegance come to life. With exquisite design & construction unmatched today, this quality generational estate is waiting for its next piece of history. Completely restored & updated to perfection, this 14,000 sq. ft. home spreads over 4 levels of living space surrounded by best most beautifully landscaped grounds full of privacy, terraced bluestone patios, fountain & pool. Freshly completed Mick DeGiulio wing with gourmet kitchen, butlers pantry opens to breakfast to family room w/incredible herringbone floors & French stone fireplace. This new enhancement seamlessly blends with the stoic entry w/ 11.5-ft ceilings & 63-foot long gallery foyer which welcomes guests through the magnificent courtyard front entrance. State-of-the art integrated sound and lighting systems to the finest cabinetry, flooring, and appliances, its a true showpiece. Handsome oak library office with hidden wet bar, huge formal dining room with room for a 16-person table opening to back patios, and 4-season room off gracious living room. 2nd floor with serene private master suite w/ a gas fireplace, two walk-in closets & access to the back stairway. lavish master bath completed with the De Giulio renovation, showcases exceptional craftmanship, stunning iceberg quartz surfaces and top-of-the-line luxuries. 4 additional bedrooms and three full baths provide ample living quarters for a large family. Two lounging spaces off main corridor allow for bonus living and works spaces also on 2nd floor. Fully finished 3rd level with one-of-a-kind industrial style office.recreation room with steel beamed vaulted ceilings, 2 more bedrooms, and full excercise room with half bath. LL with media, changing rooms for pool, impressive sit in wine cellar, arcade style game room & more. Endless space yet with a sense of warmth and elegance that you must feel to understand. A true beauty that very few homes on

New
$899,000Est. Payment
4 Beds | 4 Baths | -- Sqft
124 Eddy Lane, Northfield, IL 60093
House For Sale

Set on nearly an acre (.93) in sought after Northfield School District, this recently updated 4 bedroom, 3.1 bath home has spectacular views from every room. Sun-filled spaces and an open floor plan make this home perfect for today's lifestyle. Extraordinary space with a welcoming foyer, formal living and dining room, updated kitchen, and generous family room with floor to ceiling windows overlooking the lush backyard. The second-floor master suite includes a white bathroom and walk-in closet along with 3 roomy bedrooms and an updated hall bath. The lower level includes a spacious rec room with custom built-ins, private home office, sizable laundry, and doors leading to a private patio. Highlights include an attached 2 car garage, fully fenced yard, and 2 patios for entertaining. This home is move-in ready and NOT IN THE FLOOD PLAIN. Award-winning Middlefork, Sunset Ridge, and New Trier Schools! Easy to show!

New
$845,000Est. Payment
4 Beds | 3 Baths | -- Sqft
60 Indian Hill Road, Winnetka, IL 60093
House For Sale

OUTSTANDING COLONIAL IN SERENE INDIAN HILL ROAD SETTING! CHARM & EUROPEAN FLAIR ABOUND. FRESH WHITE PAINT AND HARDWOOD FLOORS THROUGHOUT GIVE THE HOUSE A "STUDIO MCGEE" FEEL. FOYER WITH STRIPED RUNNER, HUGE LIVING ROOM WITH BAY WINDOW, FIREPLACE & BUILT-INS. DINING ROOM WITH LOVELY MOULDING AND TONS OF NATURAL LIGHT. UPDATED EAT-IN KITCHEN WITH NEWER REFRIGERATOR, DISHWASHER AND STOVE, MUDROOM WITH BENCH. 1ST FLOOR OFFICE/BEDROOM/DEN WITH ACCESS TO FULL BATH. SUNROOM OVERLOOKS PRETTY FENCED YARD WITH PATIO PERFECT FOR SUMMER ENTERTAINING. SECOND FLOOR WAS RECENTLY RENOVATED AND INCLUDES FOUR BEDROOMS, TWO FULL BATHS, A PIN-WORTHY LAUNDRY AREA AND DECK FOR MORNING COFFEE OVERLOOKING INDIAN HILL ROAD. CONVENIENTLY LOCATED TO THORNWOOD PARK, HARPER SCHOOL AND MUCH MORE. WILMETTE SCHOOLS. NO BASEMENT. TENANT OCCUPIED UNTIL 6/30/2021.

New
$975,000Est. Payment
4 Beds | 4 Baths | -- Sqft
425 Chestnut Street, Winnetka, IL 60093
House For Sale

Adorable and updated, 425 Chestnut is nestled on deep lot in a prime location in the heart of Winnetka. From the cheerful (new in 2021) front porch you will enter into the large living room with hardwood floors, custom built-ins and high ceilings. Working from home is easy in the front sun room/office with new custom built-ins and glass paneled french doors for privacy. The graciously sized dining room has a pretty bay window and french doors which open up to the sunny and bright family room and a gracious, open, updated white kitchen. Newer stainless appliances await, as well as a beautiful, over sized Cararra marble kitchen island. The open family room offers everything we are looking for in today's homes, including two sets of French doors overlooking the deck and a fully fenced in backyard, as well as a lovely wood burning fireplace with a gas hook-up option. The first floor is complete with an updated powder room and a first floor laundry room with wainscoting and a new (2021) LG Washer and Dryer. Upstairs you will find hardwood floors throughout (new in 2015) as well as the primary bedroom and bath with white, pillowed subway tile and Cararra vanity, plus an additional generously sized family bedroom. The third floor offers two more family bedrooms and another newer full bathroom with glass shower. The basement makes the house complete with a versatile play space and a fifth bedroom with an updated full bath perfect for a teenager, a guest or as a nanny suite. As an additional, invaluable bonus and just in time for the new owners, this home offers a transferable Lifetime Warranty from US Waterproofing (2021). Updates include...In 2015: New hardwood flooring throughout the 2nd and 3rd floor and new HVAC. In 2021: new LG water and dryer, new GE gas oven, new furnace motherboard, new front porch, US Waterproofing Lifetime Transferrable Warranty, and new basement flooring, trim and paint. Only a couple of blocks from True Juice, The Book Stall, La Tequiza, The Gra

New
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.

$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!

$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.

$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.

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

EAST WINNETKA, MOVE-IN READY, ADORABLE HOME ON DEEP FENCED LOT! STEPS FROM SHOPS & RESTAURANTS IN HUBBARD WOODS, TRAIN & LAKE MICHIGAN & HUBBARD WOODS ELEMENTARY SCHOOL! 2 BED & 2 NEWER BATHS. FULL FINISHED BASEMENT W/ REC ROOM & OFFICE. NEWER FURNACE, A/C, ROOF, PLUMBING, ELECTRICAL, WINDOWS & DRIVEWAY W/ 2 CAR GARAGE. NEWER EAT-IN KITCHEN WITH NEW CABINETS, SS APPLIANCES & GRANITE COUNTERTOPS. FULLY FENCED YARD. NOT A THING TO DO!

$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.

$1,100,000Est. 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.

$230,000
$3,395,000Est. 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.

$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

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