Winnetka IL Real Estate & Homes for Sale

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Beds:
4
Baths:
3.00
Sq.Ft.:
3,163
Status:
NEW LISTING
MLS#:
12642920
Type:
Single Family
Lot size:
0.2 Acres
Year built:
1925
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 847-881-0200
View additional info

ADDITIONAL INFORMATION

If you are looking for a right-size, upsize, or downsize home that can effortlessly adapt to your changing needs, you've found your dream home. 1087 Ash is pure perfection! There is so much more than meets the eye, as the substantial addition is beautifully tucked behind the original home. Step into the sunny three-season room - perfect for morning coffee or an afternoon mahj game - and get the reveal of the incredible space and light this home offers. The formal living room, with leaded glass windows and a wood-burning fireplace, flows into an entertainment-sized dining room and then into the thoughtfully updated kitchen, featuring chef's appliances, a large island, and banquet seating for six. An adjoining sun-filled family room with custom built-ins and a gas fireplace opens to the deck overlooking the lushly landscaped backyard. And wait for it- the big surprises on the first floor: a 4th bedroom with an adjacent full bath plus two additional bonus rooms that can flex to fit your lifestyle. Need a 5th bedroom and an office? Check. Two offices and a playroom? Check. An office, gym, or guest space? Check. These extra rooms are a true luxury! Head upstairs and you'll find two generously sized family bedrooms with great closets, a pretty hall bath, and a super spacious primary suite with vaulted ceilings, two walk-in closets, and a beautifully updated bath. The lower level adds even more versatility with a carpeted rec room, bonus room, storage space, and a large laundry/mechanical/storage area. The outside space is equally fab-the professionally landscaped yard is lovely, and there is a 2 car garage with a parking pad for 2 cars on the alley. And can we talk about the fabulous tree street location? It's a dream! No need to carpool to school- Grades K-8 Winnetka schools are just blocks away. Walk or bike Winnetka Park District golf, tennis, paddle, ice rink and ballfields, the Metra, and all of the fabulous restaurants ( Pomeroy, Tocco, Hometown and more!) and shopping in vibrant downtown Winnetka. What more could you want? 1087 Ash checks every box - and then some! Don't miss this incredible home- it is truly special!

Beds:
4
Baths:
4.00
Sq.Ft.:
2,800
Status:
NEW LISTING
MLS#:
12639601
Type:
Single Family
Lot size:
0.21 Acres
Year built:
1915
A broker reciprocity listing Courtesy: Compass 847-446-9600
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ADDITIONAL INFORMATION

Bright, spacious, and beautifully maintained, this charming home offers timeless character, gracious proportions, and an exceptional in-town location on a lush, deep lot with a gorgeous patio with thoughtfully designed seating wall - perfect for entertaining and outdoor enjoyment. High ceilings, classic architectural details, and abundant natural light create a warm and inviting atmosphere throughout. The gracious living room features handsome built-ins and a lovely bay window overlooking the picturesque front yard and sought-after neighborhood, just moments from town, train, parks, and K-8 schools. The formal dining room is beautifully proportioned for both everyday living and special gatherings, while the inviting den/family room opens seamlessly to the sunny south-facing backyard. The bright eat-in kitchen offers abundant cabinetry and prep space, generous table space, and delightful views of the beautifully landscaped yard. Upstairs, the spacious primary suite includes a large bedroom, private office or sitting room with beautiful views of the lush south yard, dressing area and an en suite bath. The third-floor retreat provides wonderful flexibility as a large 4th bedroom, playroom, office, or yoga studio. The finished lower level includes a recreation/playroom, additional bedroom/office, full bath, and extensive storage. Freshly decorated and meticulously cared for throughout, this is an absolutely charming home in a vibrant neighborhood close to town, train, golf course, playfields, tennis center, and schools. A truly special offering.

Beds:
4
Baths:
5.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
12645391
Type:
Single Family
Year built:
1918
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 847-881-0200
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ADDITIONAL INFORMATION

Classic cedar shake Colonial on an exceptional 100-foot-wide lot in East Winnetka, just moments from the train, schools, beaches and town. Thoughtfully renovated with a fresh coastal aesthetic, this light-filled home beautifully blends timeless architectural detail and old-world craftsmanship with today's airy, modern style. A welcoming foyer opens to a gracious living room with hardwood floors, gas fireplace, and a charming covered porch-perfect for morning coffee or evening gatherings. The elegant dining room features recessed lighting, refined millwork, sweeping views of the professionally landscaped grounds and tiered brick terrace, and a built-in bar designed for seamless entertaining. The beautifully renovated kitchen blends style and function with high-end appliances, custom cabinetry, quartz countertops, a coffee bar, oversized island with seating, and a sunlit breakfast area ideal for gathering and entertaining. The inviting family room radiates warmth and character, featuring custom built-ins, a striking beamed ceiling, and expansive glass doors that seamlessly connect the indoors to the outdoors. The tranquil primary suite features a private sitting room and master bath. The second floor also includes three additional family bedrooms and two full baths. The third floor has been transformed into an exceptional space - the perfect versatile area for play, sleep, or work. The finished lower level offers outstanding living space with a recreation room, exercise room, bar area, laundry, half bath, and ample storage. Completing the package is an oversized 2.5-car custom garage with additional storage. A rare opportunity to own a beautifully updated home in one of East Winnetka's most desirable central locations.

Open House:

Saturday, 5/16 4:00-6:00PM

More Open House Info >

Beds:
3
Baths:
3.00
Sq.Ft.:
4,356
Status:
NEW LISTING
MLS#:
12644656
Type:
Single Family
Lot size:
0.53 Acres
Year built:
1953
A broker reciprocity listing Courtesy: @properties Commercial 312-337-0200
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ADDITIONAL INFORMATION

BRAND NEW ROOF JUST INSTALLED WITH TRANSFERABLE WARRANTY!! Beautifully maintained home offering over 4,300 square feet above grade on a rare 0.53-acre corner lot in a sought-after Winnetka location. The centerpiece of the home is the dramatic main living space featuring soaring vaulted cathedral ceilings, abundant natural light, and an impressive open feel that creates an immediate sense of scale and warmth. Hardwood floors and a flowing layout provide comfortable everyday living along with excellent entertaining space throughout. A heated and air-conditioned bonus room off the garage adds exceptional versatility, ideal for a home office, gym, playroom, studio, or additional lounge space. Situated on a generous corner lot with expansive outdoor space, the property offers endless potential to enjoy as-is or further personalize over time. Conveniently located near top-rated schools, parks, downtown Winnetka, and Metra access, this is a rare opportunity to own a home with outstanding space, character, and flexibility in an exceptional North Shore location.

Beds:
5
Baths:
5.00
Sq.Ft.:
6,900
Status:
Active
MLS#:
12637128
Type:
Single Family
Lot size:
0.33 Acres
Year built:
2004
A broker reciprocity listing Courtesy: Compass 847-416-0446
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ADDITIONAL INFORMATION

Solid stone construction, classic architecture, timeless design and refined living come together in perfect harmony in one of the most coveted and convenient locations in Winnetka/ Hubbard Woods with close proximity to town, train and Lake Michigan. Built in 2006 by Adamczyk Fine Homes and Interiors offering three levels of unparalleled craftmanship and quality totaling almost 7000 square feet. Step into the foyer with its stunning custom staircase, leading to a sun-drenched living room with fireplace and a beautifully paneled office. The spacious elegant dining room, complete with its own fireplace and a butler's pantry featuring both wine and beverage refrigerators, sets the stage for unforgettable gatherings. The gourmet kitchen is a chef's dream, boasting an oversized island, and a separate breakfast area. It seamlessly flows into the family room, where built-in bookcases, a fireplace, and French doors open to a serene bluestone patio and sizable fenced private backyard. Functional and practical mudroom/laundry room connects to the attached two-car garage. Upstairs, the sunlit second floor offers a luxurious primary suite with spa-like bath, and dual walk-in closets. There are four additional comfortable bedrooms. The fifth bedroom can be flexible space as a private sitting room (or extra 15 x 14 walk-in closet for the primary suite), Two more bathrooms complete the upper level. The deep pour lower level with high ceilings is a retreat of its own, featuring a stone wine room, two recreation areas, the sixth bedroom with full bathroom, exercise room, and storage. Outside, the meticulously landscaped grounds provide a picturesque backdrop for this extraordinary home. With its refined details, quality materials, flowing floorplan, and thoughtful design, this property offers a perfect blend of sophistication and comfort. Truly, a forever home that will stand the test of time! New Brava Synthetic Composite Roof 2025, 2 new ACs 2022 & 2020, furnace 2023.

Beds:
6
Baths:
6.00
Sq.Ft.:
7,000
Status:
Active
MLS#:
12637769
Type:
Single Family
Lot size:
1.55 Acres
Year built:
1933
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 847-881-0200
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ADDITIONAL INFORMATION

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 the land value alone is worth at least $2 million dollars. 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 outlining the incredible backyard. Step down to a beautiful formal living room with a stone Parisian FP & custom French doors that open up to the cozy sunroom with picturesque windows overlooking the backyard. Finely appointed dining room with Visual Comfort light fixture layered with de Gournay wallpaper, antique marble fireplace and another set of French doors open out to the bluestone patio and deep backyard. Finely crafted white Chef's kitchen by O'Brien Harris with Villa Blanca marble, Clark & Barlow hardware, antique mirrored backslash and Holly Hunt pendents. Seamless transition to family rm ideal for cooking and entertaining at the same time. Command center mudroom, 2 powder rooms, and brand new laundry room also on this level. Two staircases lead the way up to large 2nd floor with intimate "Ralph Lauren" inspired den richly finished in restored paneled chestnut walls & handsome built-ins w/ dark marble FP. Large primary suite with room for even more expansion over porch is completed with Ann Sacks white bath and gracious marble FP with custom built-ins accented by a built-in window bench. 3 additional bedrooms with one being a large family bedroom w/ en-suite bath. The other 2 beds share pretty all white redone bathroom. Up to the oversized fully finished 3rd floor with 2nd family room and 2 beds ideal for in-law quarters or nanny. Lower level with mechanicals and ample storage space. The vibe of this home is effortlessly inviting-warm, layered, and livable across all 3 finished levels, seamlessly blending indoor & outdoor living. And with ample space to add a pool, the vision of true Southern comfort could be fully realized, elevating this already timeless retreat into a personal resort unlike any other.

Beds:
6
Baths:
9.00
Sq.Ft.:
6,000
Status:
Active
MLS#:
12638690
Type:
Single Family
Year built:
2014
A broker reciprocity listing Courtesy: Stone Realty Group 312-504-6647
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ADDITIONAL INFORMATION

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 and full outdoor kitchen. Perfect yard for a pool and/or sports court. Heated 3-car garage. Smart home with Crestron System. Backup generator. Incredible attention to detail & finishes. A must see!! Glencoe Schools!

Beds:
5
Baths:
9.00
Sq.Ft.:
6,950
Status:
Active
MLS#:
12606067
Type:
Single Family
Lot size:
0.5 Acres
Year built:
2006
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 312-682-8500
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ADDITIONAL INFORMATION

Beds:
4
Baths:
6.00
Sq.Ft.:
4,680
Status:
Active
MLS#:
12608265
Type:
Single Family
Lot size:
0.32 Acres
Year built:
2010
A broker reciprocity listing Courtesy: Compass 847-446-9600
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ADDITIONAL INFORMATION

This extraordinary residence, originally dating to the 1920s and completely rebuilt in 2010-including a fully excavated lower level-offers an exceptional blend of timeless architectural character and refined modern luxury across four impeccably finished levels. Set on an expansive 75 x 187 lot, the stately brick exterior, enhanced by a handsome porte cochere, creates a memorable and elegant introduction to the home, hinting at the remarkable quality and thoughtful design found within. Every detail has been meticulously curated to deliver a home of extraordinary craftsmanship, scale, and sophistication. Rich custom millwork, beautifully crafted windows, bespoke cabinetry, exquisite stonework, and designer lighting are seamlessly integrated throughout, creating a cohesive and elevated aesthetic. The interior offers both grand, light-filled spaces ideal for entertaining and more intimate, comfortable areas designed for everyday living. The property itself is equally impressive, with lush, professionally landscaped grounds (designed by Red Spade Environments) fully irrigated by an in-ground sprinkler system. The outdoor living experience is truly exceptional, featuring a stunning patio with pergola that invites relaxed gatherings, as well as a second, more casual patio just off the kitchen and family room-perfect for effortless indoor-outdoor living. Adding to the charm and uniqueness of the setting is a charming brick garage with its own outdoor fireplace and patio, creating a warm and inviting retreat for entertaining or quiet, tranquil evenings at home. Perfectly positioned in a highly sought-after location, this home offers unparalleled convenience to top-rated schools, scenic parks, a nearby golf courses (18 hole and 9 hole par 3), tennis and paddle facilities, and the vibrant town center with its shops, dining, and train access. Combining architectural integrity, modern amenities, and an unbeatable location, this is a truly special offering that embodies both elegance and lifestyle at the highest level.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,435
Status:
Active
MLS#:
12631351
Type:
Single Family
Lot size:
0.17 Acres
Year built:
1956
A broker reciprocity listing Courtesy: Compass 847-446-9600
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ADDITIONAL INFORMATION

Welcome to this truly charming, picture-perfect home in an unbeatable walk-to-everything location. The beautifully designed first floor showcases an elegant living room with fireplace that flows effortlessly into the dining room, highlighted by stunning built-ins. The inviting family room-also featuring custom built-ins-is the perfect place to gather and opens seamlessly to a sleek, thoughtfully designed kitchen with a generous eating area, all leading to a private patio and lush backyard-ideal for both everyday living and memorable entertaining. Upstairs, the exceptional primary suite feels like a true retreat, with soaring ceilings, expansive space, and a lovely Juliette balcony overlooking the serene backyard. The spa-like en suite bath features a luxurious shower, handsome double vanity, private water closet and excellent storage. Two additional bedrooms each enjoy access to their own baths, while a beautifully designed coffee/wine bar with fridge and sink adds a sophisticated and indulgent touch. The bright and cheerful lower level offers a versatile workspace and playroom, a well-equipped laundry area, and outstanding storage, including a cedar closet. An attached one-car garage, along with an additional parking pad off the alley, provides convenience and flexibility. Impeccably maintained and thoughtfully updated throughout, this is a truly special home that effortlessly blends comfort, style, and functionality.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,932
Status:
Active
MLS#:
12628467
Type:
Single Family
Year built:
1928
A broker reciprocity listing Courtesy: Compass 847-446-9600
View additional info

ADDITIONAL INFORMATION

Beds:
5
Baths:
5.00
Sq.Ft.:
3,347
Status:
Active
MLS#:
12627550
Type:
Single Family
Year built:
1930
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 847-432-0700
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ADDITIONAL INFORMATION

Spacious 5 bedroom 4 1/2 bath Dutch Colonial in desirable Hubbard Woods, ideally situated in a wonderful neighborhood just moments from Hubbard Woods School, the Metra train, downtown shops, restaurants and scenic forest preserve trails for biking, running, kayaking and fishing. The first floor offers loads of natural light, with welcoming living and dining areas plus a dedicated office. The eat-in kitchen with new appliances flows seamlessly into a sunlit family room overlooking the backyard. A convenient mudroom leads out to a spacious deck and a sunny, south-facing backyard-ideal for relaxing or entertaining. Upstairs, you'll find the primary suite with a newly remodeled bathroom and huge walk-in closet. Four additional bedrooms, a second, newly remodeled bathroom and third bathroom to top it off. The basement offers mostly finished space with new flooring and lighting, a full, vintage bathroom, expansive recreation room with built-out laundry space, utility room, and abundant storage options. Recent updates include: 2026 * Routine sewer rodding. 2025 * New pressure tank for boiler * Basement remodel (framed/painted walls, new flooring, lighting and laundry cabinets) * New basement refrigerator. 2024 * New Pella windows on back of house * New Samsung dryer * Routine boiler maintenance * Chimney sweep. 2023 * New deck * New Pella windows on front of house * New Gas range * New Refrigerator * New Microwave. 2022 * Primary Bathroom expansion/remodel * Primary walk-in closet expansion * Hall bathroom remodel * New Ro-Hi reverse osmosis water filter system * New Samsung washer * Routine sewer rodding * New driveway. 2020 * Re-conditioned fireplace/chimney: tuckpointed exterior chimney, tuckpointed firebox, * New chimney liner, new appliance liner (for boiler & hot water heater exhaust) * New Whirlpool dishwasher. 2019 * New roof on house and garage * New A/C condenser * Routine sewer rodding. 2017 * New boiler. 2016 * New hot water heater.

Beds:
4
Baths:
5.00
Sq.Ft.:
4,574
Status:
Active
MLS#:
12620950
Type:
Single Family
Lot size:
0.92 Acres
Year built:
1955
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 847-881-0200
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ADDITIONAL INFORMATION

This incredible & expansive 4 bedroom, 3.2 bathroom home is situated on a spectacular property in an idyllic & private location. Surrounded by mature trees and beautiful foliage, the fantastic gardens & outdoor area boast three bluestone patios. The home brings the outdoors inside with oversized windows throughout the home. When you walk into the home, you are welcomed in the large foyer and move into the living room with marble surround fireplace that is sun-filled and bright. This leads you to the enclosed porch area where you can bask in the sun with walls of windows & surrounded by private, beautiful and mature landscaping. This home truly brings the outdoors inside to you! The dining room is perfect for hosting events and leads to the white eat-in kitchen with an island and double ovens that is very spacious for cooking and entertaining. The kitchen is conveniently located next to the first-floor laundry room. Down the hall from the kitchen is a huge wood beamed ceiling family room with patio doors that open to the outside, a fireplace with granite surround and built-in bookshelves where the media resides. The octagonal office with an oversized vaulted ceiling and is flanked with floor to ceiling windows and beautiful built-in bookshelves. Working from home has never been more relaxing in this serene setting. Take the steps off the family room up to the recreation room where you can play pool, games or watch tv in this amazing playroom area. The functionality of having a large first floor primary suite, with attached bathroom, closets galore, near your own outdoor oasis is spectacular. You are in your own bed and breakfast when sleeping in the first-floor primary suite retreat surrounded by gardens and a bluestone walkway. The second floor has three additional bedrooms and two full bathrooms. With an attached 3 car garage, circular driveway on the property and parking for guests in front of the home, you are ready to host any event at this incredible home. The lower level has storage galore and a wine cellar. This is a very special home that has been well loved for many years on the most incredible and expansive property.

Beds:
6
Baths:
10.00
Sq.Ft.:
15,000
Status:
Active
MLS#:
12600188
Type:
Single Family
Lot size:
0.93 Acres
A broker reciprocity listing Courtesy: Village Realty Group Inc 847-251-5714
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ADDITIONAL INFORMATION

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 privacy, wellness, and architectural presence-without compromise. Designed with a timeless, classic architectural aesthetic and infused with modern innovation for 2026 living, this residence delivers true first-floor living and entertaining with every amenity required for builders "Five Star Living Every Day". The main floor estate amenities feature builders signature 50-foot art gallery with museum-quality lighting, a spectacular kitchen connected to outdoor entertaining, a 60-foot in-ground pool, dining capacity for 30, dine-in wine cellar, billiards and bar lounge, home theater, golf and sports simulator room, private office and den, wellness center with steam, sauna, whirlpool spa, cold plunge, massage room, and fitness center, and a luxurious primary suite, all on the main level. Situated on a rare one-acre lot in the coveted Crow Island School District, the 3 stop elevator to the second floor offers four ensuite guest bedrooms, with additional guest accommodations and extensive storage on the 10' ceilings lower level. Extensive landscaping and heated outdoor living spaces for entertainment and pool and outdoor spa fun complete this unique opportunity. Offered at $16,900,000. Serious inquiries only

Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
12620403
Type:
Single Family
Year built:
1921
A broker reciprocity listing Courtesy: Compass 312-319-1168
View additional info

ADDITIONAL INFORMATION

Beds:
4
Baths:
5.00
Sq.Ft.:
3,639
Status:
Active
MLS#:
12613148
Type:
Single Family
Lot size:
0.21 Acres
Year built:
1994
A broker reciprocity listing Courtesy: Compass 847-446-9600
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ADDITIONAL INFORMATION

Easy, in-town living in this wonderful home! This spacious home is conveniently located in the ideal 'walk to everything' location in the heart of Winnetka - close to absolutely everything. Built in 1995 with all the amenities one needs: classic center entry layout, large welcoming foyer, bright interior with an abundance of natural light, large scaled rooms, eat-in kitchen adjacent to family room which has sliding doors out to the southern patio and fully fenced yard. Primary suite with ensuite bath (with soaking tub, double vanities & separate shower), walk-in closet & skylight. Three additional bedrooms and 2 full baths round out the 2nd floor. Finished lower level with heated floors and a rec room and play area plus full bath. Plenty of storage throughout the home including the large storage room in the basement. All in move-in condition! Special amenities include first floor laundry/mudroom, 2 car attached / heated garage. This well designed and light-filled house is located on a large corner lot (50 x 187) and is bathed in sunlight all day long. A short walk to the center of downtown Winnetka for shopping, restaurants, parks and train and a short walk to K-8 schools, golf, tennis, paddle facilities and ice arena. All the space you need in all the right places!

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
12589833
Type:
Single Family
Lot size:
0.15 Acres
Year built:
1922
A broker reciprocity listing Courtesy: Baird & Warner 847-446-1855
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ADDITIONAL INFORMATION

Perfectly situated in a prime East Winnetka location, this charming home offers an exceptional opportunity to enjoy one of the North Shore's most sought-after neighborhoods at an approachable price point. Just blocks from the lake, town, Metra, Greeley Elementary, and New Trier High School, the lifestyle and convenience are unmatched. Thoughtfully updated over time, the home features bright, sun-filled living spaces enhanced by skylights, creating a warm and inviting atmosphere throughout. The main level offers a comfortable living room, an updated eat-in kitchen, and a separate dining room, along with two well-proportioned bedrooms and a full bath. The second floor is dedicated to the primary suite with an adjoining office space-ideal for today's work-from-home needs. Hardwood floors run throughout, and the home has been carefully maintained with numerous improvements already in place. The finished basement provides valuable additional living space with a rec room, powder room and laundry room. The backyard is a true highlight, featuring a lovely patio and generous green space-perfect for relaxing or entertaining. A newer two-car garage, conveniently accessed off Walnut by an easement, preserves the yard while adding everyday ease and functionality. Set on a beautiful block, this is a rare opportunity for buyers seeking the charm, location, and community of East Winnetka!

Beds:
5
Baths:
5.00
Sq.Ft.:
5,231
Status:
Active
MLS#:
12611137
Type:
Single Family
Lot size:
0.22 Acres
Year built:
1926
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 847-881-0200
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ADDITIONAL INFORMATION

Refined elegance meets timeless North Shore charm in this premier East Winnetka location, served by Joseph Sears School (JK-8) and New Trier High School. This beautifully updated and impeccably appointed residence offers 5 bedrooms and 4.1 baths, gracious formal living and dining rooms, and a seamless open-concept layout designed for both sophisticated entertaining and everyday living. At the heart of the home is a stunning, Mick DeGiulio-inspired chef's kitchen featuring high-end finishes, custom cabinetry, and thoughtful design that flows effortlessly into the sun-filled family room.Completely renovated and expanded in 2017, the home has been meticulously maintained and further enhanced. Thoughtful upgrades include custom built-in closets and a flexible floor plan with a separate entrance-ideal for a private practice or dedicated work-from-home environment. Additional improvements include a full chimney replacement in 2022 and professionally designed landscaping completed in 2019, creating a polished and inviting outdoor setting.Rare for the area, the home features a two-car attached garage, a well-designed mudroom, and an expanded lower level offering exceptional versatility for recreation, fitness, guests, or additional workspace.

Beds:
6
Baths:
6.00
Sq.Ft.:
5,458
Status:
Active
MLS#:
12611829
Type:
Single Family
Lot size:
0.99 Acres
Year built:
1988
A broker reciprocity listing Courtesy: Greystone Realty 847-997-1639
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ADDITIONAL INFORMATION

MULTIPLE OFFERS! HIGHEST AND BEST DUE 5PM ON 4/24/26! Set at the end of a quiet, private cul-de-sac on a rare acre lot, this custom-built Georgia marble home with an inground pool showcases timeless elegance and exceptional craftsmanship in the Woodley neighborhood of Winnetka. A gracious foyer with stained glass double entry doors, marble tile floors, fresh paint, and a sparkling crystal chandelier, greets you to six bedrooms, four full baths, two half baths and over 5,400 square feet of refined living and sophistication. The eat in chef's kitchen features beautiful quartzite countertops with breakfast bar seating, stacked upper cabinets, walk in pantry, and premium appliances, including a Sub-Zero refrigerator, Thermador double oven, Bertazzoni cooktop with hood, and a Bosch dishwasher. The grand family room offers oak hardwood floors, soaring 15-foot vaulted ceilings with skylights, a striking stone wood-burning fireplace, and a wet bar, all overlooking the newer expansive Trex deck that wraps around the concrete inground pool. A west-facing four-season room is filled with natural light and provides views of the stone paver patio-ideal for summer bonfires. The main level offers an executive office with rich wood paneling, decorative sconces, and a built-in bookcase. Additional highlights include a comfortable living room with second gas-start fireplace and floor to ceiling Pella casement windows, a formal dining room, half bath, a first-floor guest suite with a newly renovated ensuite bath, and a well-organized laundry room with cubbies, wash sink, and folding area. Upstairs, you'll find five spacious bedrooms with brand-new carpet and solid-core doors, along with two full baths. The expansive primary suite features dual walk-in closets, individual vanities, a soaking tub, water closet, and an oversized steam shower. The finished basement adds approximately 2,300 square feet of recreation space, complete with built-in surround sound, a full kitchenette, bookshelves, ample storage, and a half bath. The home offers dual-zoned HVAC, a sump pump with battery backup, central vacuum system, a three-car garage equipped with a 220V outlet for electric vehicle charging, a newer asphalt driveway with stamped concrete front steps, freshly painted exterior, landscape lighting, outdoor speakers, and a partially fenced generous yard for backyard activities. Ideally located on the North Shore with easy highway access, this home is served by the highly sought-after New Trier High School and is within walking distance to award winning Marie Murphy Middle School. A true hidden gem of Winnetka!

Beds:
5
Baths:
4.00
Sq.Ft.:
3,465
Status:
Active
MLS#:
12610110
Type:
Single Family
Lot size:
0.22 Acres
Year built:
1924
A broker reciprocity listing Courtesy: Compass 847-446-9600
View additional info

ADDITIONAL INFORMATION

Welcome to 373 Sunset Road, an spacious 5-bedroom, 3.1-bath brick and frame home in sought-after East Winnetka. Ideally located near Greeley Elementary, New Trier High School, the Indian Hill Metra, and just moments from Lake Michigan beaches, this home offers a wonderful blend of classic architecture and exceptional space. The gracious floor plan features a welcoming foyer, office/music room, formal dining room, and a large family room with fireplace and sliding doors to the patio and backyard. The galley-style kitchen opens to a light-filled breakfast room (currently used as a sitting room) overlooking the expansive yard (50 x 192) and in-ground pool. The second level includes a spacious primary suite with walk-in closet and large bath, along with three additional bedrooms a hall bath and a home office. The third floor offers flexible living with a sitting /office area and fifth bedroom space, and full bath-ideal for guests, work, or recreation. The unfinished lower level provides excellent storage in two storage rooms and future potential. Set on a lush, deep lot, the property features a large patio, pool, and sweeping green space-perfect for outdoor living and entertaining. A rare opportunity in one of Winnetka's most desirable locations.

Beds:
1
Baths:
1.00
Sq.Ft.:
760
Status:
Active
MLS#:
12606299
Type:
Single Family
Year built:
1926
A broker reciprocity listing Courtesy: @properties Christie's International Real Estate 847-881-0200
View additional info

ADDITIONAL INFORMATION

Welcome to the charming chimneys. Quiet and secluded. Pretty and bright top floor unit looking out on quaint, treelined courtyard. A large living room greets you with abundant natural light and a charming, wood burning fireplace. Separate, updated white kitchen with shaker style cabinets and granite countertops. Appliances include a double oven, gas stove, dishwasher and refrigerator/freezer. Bright and light hardwood floors throughout. Nice desk nook and large bedroom with closet for storage. Updated bathroom with custom shower. 2 convenient air conditioning units. Parking spot included. Large storage room downstairs with ample laundry room available for coin laundry. Assessments include HEAT. Outstanding location across from the Indian Hill Metra train station. Blocks to the Lake and New Trier. Come see! AS IS

Open House:

Sunday, 5/24 5:00-8:00PM

More Open House Info >

Beds:
4
Baths:
2.00
Sq.Ft.:
2,100
Status:
Active
MLS#:
12606031
Type:
Single Family
Year built:
1919
A broker reciprocity listing Courtesy: Jason Mitchell Real Estate IL 708-917-6640
View additional info

ADDITIONAL INFORMATION

Nestled just blocks from Winnetka's famed lakefront, this 4-bed/1.5-bath single-family home at 979 Vine St offers approximately 2,100 sq ft of living space, hardwood floors, a spacious kitchen, and thoughtful layout across levels. Located a few blocks to Tower Road Park/ beach - Lake Michigan and Lloyd Park Boat Launch.. Steps to Green Bay Train - for biking, running, and casual strolls. Plus close to downtown amenities. Homes within a one-mile radius average about $1.7-2.2 million, making this residence a rare opportunity to live the lakefront lifestyle without the million-plus premium. Zoned to allow up to two units. Assumable mortgage at under 4, on portion of purchase price. Remodel to create a multi million dollar property. Contact listing broker for more details.

Beds:
4
Baths:
4.00
Sq.Ft.:
5,409
Status:
Active
MLS#:
12587281
Type:
Single Family
Lot size:
0.52 Acres
Year built:
1835
A broker reciprocity listing Courtesy: Compass 847-446-9600
View additional info

ADDITIONAL INFORMATION

Beds:
4
Baths:
5.00
Sq.Ft.:
4,390
Status:
Active
MLS#:
12585208
Type:
Single Family
Lot size:
0.17 Acres
Year built:
2015
A broker reciprocity listing Courtesy: Compass 312-319-1168
View additional info

ADDITIONAL INFORMATION

Blending timeless elegance with modern sophistication, this stunning 2016 Winnetka home feels better than new. Designed for light, flow, and effortless living, it features 10-foot ceilings, white oak floors, and expansive windows that fill each room with warmth. The gourmet kitchen showcases custom cabinetry, large island, and professional appliances is perfect for everyday living and entertaining. With 5 spacious bedrooms, 2 offices, and a beautifully finished lower level, there is space for everyone to live, work, and play in comfort and style. For added convenience, laundry rooms are thoughtfully located on both the lower level and the upper level. Outside, enjoy a fenced yard, bluestone patio, and the charm of a quiet cul-de-sac near parks and the lakefront. A half block from the highly coveted Hubbard Woods School, and only minutes from Metra, shops, restaurants, and Tower Beach, this meticulously maintained home offers luxury, comfort, and an unbeatable location in the heart of Hubbard Woods.

Beds:
6
Baths:
7.00
Sq.Ft.:
5,350
Status:
Active
MLS#:
12482150
Type:
Single Family
Year built:
1920
A broker reciprocity listing Courtesy: Compass 847-446-9600
View additional info

ADDITIONAL INFORMATION

Better than NEW! This artfully restored & renovated home has the incredible combination of a classic center entry colonial home with sophisticated formal rooms and all the current amenities for today's modern lifestyle. This four-level home features abundant natural light, oversized windows, wide room openings and gleaming hardwood floors throughout. Spacious rooms, a current layout, high-end finishes and thoughtful design exist at every turn. Located in the northern end of Winnetka, just blocks to Hubbard Woods school, town, train, shops, restaurants, parks, the forest preserve bike and running trails. Easy access to downtown Chicago. First floor includes a gourmet kitchen with butler's pantry, formal dining room, sun-drenched living & family spaces, a private home office, and a custom mudroom with full laundry room. Upstairs, the luxurious primary suite offers a spa-like shower, double vanity and walk-in closets. Additional bedrooms are generously sized, one bedroom is en-suite and the 3rd & 4th bedrooms share a large hall bath. There is additional 2nd floor laundry for ultimate convenience. Fully finished lower level and 3rd fl provide flexible living space for extra BR's, recreation, guests, or work-from-home needs. Both have gorgeous full bathrooms. Exceptional outdoor living includes brick patio, lush landscaping and private, fenced yard. A rare blend of classic charm and modern luxury in a prime location.

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Andrea D. Conner, License 471020674, Xome Inc., License 478026347, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Ste 100, Lewisville, TX 75067


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Winnetka Real Estate

Winnetka is located in Illinois. Winnetka, Illinois has a population of 12,658. Winnetka is more family-centric than the surrounding county with 48.66% of the households containing married families with children. The county average for households married with children is 29.73%.

The median household income in Winnetka, Illinois is $250,001. The median household income for the surrounding county is $72,121 compared to the national median of $69,021. The median age of people living in Winnetka is 42.6 years.

Winnetka Weather

The average high temperature in July is 83.1 degrees, with an average low temperature in January of 16.7 degrees. The average rainfall is approximately 36.4 inches per year, with 35.9 inches of snow per year.

Winnetka Map

Winnetka Real Estate Market Conditions

  • Median sales price

    $1,905,000
    14.5%
    change since last quarter
  • # Active listings

    33
    30-day change

Winnetka Schools and Demographics

Education near Winnetka, IL

City County
High School Graduates 99.05 87.97
College Degree - 2 year 1.95 6.73
College Degree - 4 year 90.39 40.75
Graduate Degree 32.62 12.01
Expenditures per Student 21,907 21,907
Students per Teacher 14 14

Elementary Schools near Winnetka, IL

Grades Students P/T Ratio ZIP
Avoca West Elementary School KG - 05 446 9.7 60025
Central Elementary School KG - 04 507 13.8 60091
Crow Island Elementary School KG - 04 391 12.2 60093
Glen Grove Elementary School 03 - 05 530 14.1 60025
Greeley Elementary School PK - 04 276 10.9 60093
Harper Elementary School KG - 04 428 15.1 60091
Henking Elementary School PK - 02 483 12.9 60025
Hoffman Elementary School 03 - 05 599 15.1 60025
Hubbard Woods Elementary School KG - 04 249 9.7 60093
Lyon Elementary School PK - 02 476 15.2 60025
McKenzie Elementary School KG - 04 512 14.9 60091
Middlefork Primary School PK - 03 203 11.8 60093
Pleasant Ridge Elementary School 03 - 05 549 15 60025
Romona Elementary School PK - 04 518 13.8 60091
South Elementary School KG - 02 352 13.5 60022
The Joseph Sears School PK - 08 495 8.7 60043
Washington Elementary School PK - 06 303 11.2 60025
West School 03 - 04 258 12.6 60022

Middle Schools near Winnetka, IL

Grades Students P/T Ratio ZIP
Carleton W Washburne School 07 - 08 440 10.4 60093
Central School 05 - 08 589 10.1 60022
Highcrest Middle School 05 - 06 841 12.8 60091
Marie Murphy School 06 - 08 261 9.3 60091
Springman Middle School 06 - 08 854 13.9 60025
Sunset Ridge Elementary School 04 - 08 279 8.6 60093
The Skokie School 05 - 06 439 11.1 60093
Wilmette Junior High School 07 - 08 884 12.3 60091

High Schools near Winnetka, IL

Grades Students P/T Ratio ZIP
New Trier Township H S Winnetka 10 - 12 3,086 11.6 60093

Ungraded Schools near Winnetka, IL

Grades Students P/T Ratio ZIP
New Trier Township H S Northfield 09 - 09 971 11 60093

Demographics near Winnetka, IL

City County
Neighborhood Type Suburban
Population 12,658 5,265,398
Population Density 3,325 5,572
Median Age 42.6 37.3
People per Household 2.9 2.5
Median Household Income 250,001 72,121
Average Income per Capita 143,109 41,706

Real estate near Winnetka