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555 Hill Terrace Unit #307, Winnetka
$300,000
1 Beds ⋅ 1 Baths ⋅ 12606299 MLS ⋅ CLOSED Status
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

555 Hill Terrace Unit #307, Winnetka

1368 Scott Avenue, Winnetka
$1,650,000
5 Beds ⋅ 5 Baths ⋅ 12627550 MLS ⋅ CLOSED Status
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.

1368 Scott Avenue, Winnetka

841 Prospect Avenue, Winnetka
$1,615,000
5 Beds ⋅ 4 Baths ⋅ 12607166 MLS ⋅ CLOSED Status
Coveted East Winnetka location just two blocks from Tower Road Beach! This charming 5-bedroom, 3.1-bath home offers timeless character and wonderful living space, complete with an inviting front porch. The living room showcases a coffered ceiling, oversized wood-burning fireplace, and beautiful period millwork. A bright sunroom with built-in bookcases provides the perfect retreat. Hardwood floors run throughout the first floor, which also features a spacious dining room with a bay window and a kitchen with a breakfast bar that opens to the family room. The family room overlooks the back deck and yard-ideal for everyday living and entertaining. A powder room completes the main level. The second floor offers four bedrooms, including a generous primary suite with built-in storage, two closets, and a private bath. Three additional bedrooms share a hall bath; one features a bay window, and one is currently being used as an office. All bedrooms offer ample closet space. The third floor includes a charming treetop bedroom, a full bath, and additional attic storage. An unfinished basement provides endless potential to expand your living space. Unbeatable location close to Hubbard Woods Metra, steps to Tower Road Beach and park, and within the sought-after Greeley Elementary School district. Don't miss this special home in an A+ location. Property is being conveyed as-is.

841 Prospect Avenue, Winnetka

574 Orchard Lane, Winnetka
$1,000,000
3 Beds ⋅ 3 Baths ⋅ 12589833 MLS ⋅ CLOSED Status
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!

574 Orchard Lane, Winnetka

1255 Forest Glen Drive, Winnetka
$2,350,000
5 Beds ⋅ 5 Baths ⋅ 12605782 MLS ⋅ CLOSED Status
Classic Hemphill Colonial on an oversized 75-foot-wide lot, completely renovated in 2014 with all the charm of a 1950s home but the newness of newer construction. What you will love is this home is all done for you with all the must haves that are hard to find- like attached garage, mudroom, high ceilings, newer windows, designer kitchen, dream primary suite, 2nd floor laundry, huge basement with high ceilings , and quiet street. This brick home blends timeless architecture with modern living. The main level has a formal living room and dining room but the show stopper 2014 addition of a huge family room with vaulted cathedral ceilings and tons of windows. Connecting to the designer kitchen with an oversized center island, eat-in dining area, walk-in pantry, Thermador, Wolf, and Miele applainces, including a built-in coffee machine. The kitchen flows seamlessly into the family room and backyard, creating an ideal layout for everyday living and entertaining. Hardwood floors, custom millwork, and quality finishes are found throughout- 2 fireplaces with gas starter and marble surround. Family room has a built in dry bar with additional beverage storage. The primary suite is a private retreat featuring two walk-in closets and a luxurious bathroom with a freestanding Victoria Albert Tub soaking tub, perrin and rowe fixures, rain shower, marble bathroom, separate vanities and sinks, heated floors. 2nd Floor Laundry room and 3 additional bedrooms with 2 full bathrooms dedicated to them. The fully dug-out basement provides expansive additional living space-ideal for a recreation room, home gym, office, or guest suite, plus a half bath. Additional highlights include an attached garage, updated systems, and a wide backyard with ample room for outdoor enjoyment. An opportunity to own a move-in-ready Hemphill Colonial offering modern updates, generous living space, and an exceptional location. Professional landscaping and bluestone patio in the backyard with a sprinkler system. Water Heater 2026. Showings will resume April 14th.

1255 Forest Glen Drive, Winnetka

845 Glen Oak Drive, Winnetka
$2,555,000
4 Beds ⋅ 5 Baths ⋅ 12583662 MLS ⋅ CLOSED Status
Located in a superb East Winnetka location this 4 bedroom 3.2 bath lovely classic Hemphill built home boasts 3 car attached garage and an elevator. Glen Oak Drive is a private cul-de-sac street on the lake east of Sheridan Road with only 5 stately homes. A separate circular drive & double door entry leads into a large and gracious foyer with pretty moldings and staircase. When you step into the spacious foyer, you are greeted by the open and beautiful staircase. Off the foyer is a spacious living room featuring a decorative fireplace and built in bookcases. The living room flows into a sun filled sunroom with skylight and sliding glass doors leading to a bluestone terrace and private back yard. Adjacent to the sunroom is an inviting family room with a wood-burning fireplace and wet bar. A lovely formal dining room has impressive moldings and is adjacent to the kitchen. There is a handsome private office boasting wood paneling and built in bookcases and an elegant guest powder room, just steps away off the foyer with second first floor powder room. The large kitchen features abundant white cabinetry, center island, stainless steel appliances and a designated eating area. Conveniently located off the kitchen is the laundry room with many cabinets and closets for all your storage needs and an additional powder room. The oversized attached heated 3 car garage is 1050 SF and has a staircase leading to an attic above and a second staircase to the basement. A traditional staircase or the elevator brings you upstairs to the second floor which features 4 large bedrooms with fabulous closet space and 3 full bathrooms. The primary suite bedroom has access to a private balcony overlooking the backyard, 2 large walk-in closets and a primary bath with separate shower and tub. In the full basement there is a recreation room, an area for a fifth bedroom or second office, walk-in cedar closet and abundant storage. The elevator services all 3 levels of the house. There are beautiful architectural moldings and chair rail detail in the house along with dark stained hardwood floors throughout and nine foot ceilings that grace the first floor. The lower level is spacious and awaits your personalization. Enjoy seasonal views of the lake and cool breezes from this classic home in a most coveted location near Tower Road Beach.

845 Glen Oak Drive, Winnetka

642 Ash Street, Winnetka
$1,450,000
4 Beds ⋅ 4 Baths ⋅ 12626097 MLS ⋅ CLOSED Status
Location, curb appeal and charm - all in one! This East Winnetka home welcomes you with a large front porch and bright foyer leading to a spacious living room with fireplace and room for two seating areas. French doors open to a deck, flooding the space with light. The large kitchen and family room anchor the rear of the house with windows on three sides, a generous eat-in area, and direct access to the deck and yard-perfect for indoor/outdoor living and entertaining. A butlers pantry connects the kitchen to the separate formal dining room and completes the main level. Upstairs features a lovely primary suite, three additional bedrooms, and a full bath. The lower level offers a large rec room, fifth bedroom, another full bath, laundry, and abundant storage. A mudroom area connects you to the attached over sized one car tandem garage. Thoughtful layout, great flow, and flexible living space-move-in ready. Do not miss!

642 Ash Street, Winnetka

67 Brier Street, Winnetka
$1,890,008
5 Beds ⋅ 6 Baths ⋅ 12431472 MLS ⋅ CLOSED Status
New construction home with 5BR, 6Bath,2 car detached garage, will be ready by March 2026. This more than 4000 sqft house boasts thoughtfully designed living space, combining modern luxury with everyday functionality, front and back porches and second floor primary BR with balcony, two heating and cooling zones, two laundries, two dishwashers, two wine coolers. Step inside to soaring ceilings, and open layout, and high-end finishes throughout. The gourmet kitchen is a chef's paradise with custom cabinetry and countertops, has a large center island, and with premium appliances. Each spacious BR features an en-suite bathroom. The primary suite is true retreat, boasting a spa-like bathroom with soaking tub, walk-in shower, heated floor, has dual vanities and generous walk-in closet. Entertain effortlessly in the expansive living and dining areas or take the gathering outdoors on the deck and landscaped yard. The fully finished third floor comes with huge bedroom with full bath. The fully finished lower level comes with dry kitchen with dishwasher/wine cooler, bedroom, work room, storage and bathroom. With detached garage, this home has nice backyard, dedicated office space, smart home features, and energy efficient systems. Perfectly located within walking distance of Joseph SearsK-8 and New Trier High schools, Indian Hill Metra station. Few minutes away from Winnetka downtown, Library, Shopping and all fabulous downtown restaurants. Short walk to Lake Michigan - this home truly has it all.

67 Brier Street, Winnetka

1505 Tower Road, Winnetka
$1,305,000
3 Beds ⋅ 4 Baths ⋅ 12606156 MLS ⋅ CLOSED Status
Renovated in 2019, this home was completely reimagined with a fresh modern aesthetic and refined mid-century edge. Ideally located in a sought-after neighborhood near parks, schools, the train, and town, it offers incredible natural light, an easy-flow layout, and the kind of space, style, and functionality that is hard to find. A generous foyer opens to sun-filled living and dining spaces with new hardwood floors, modern built-ins, and wood-burning fireplace, all flowing seamlessly into the sleek white kitchen with breakfast bar, quartz countertops, striking designer backsplash, and Bosch stainless steel appliances, including a drawer microwave. A four-season room with new flooring, high-efficiency windows, and heater that extends the living space and opens to an oversized back deck overlooking the huge fenced backyard. Set on a 200-foot-deep lot, the attached two-car garage is a rare and highly desirable feature for this style of home, offering everyday convenience while allowing for even more usable outdoor space. A first-floor office with a closet sits next to a full bath, creating ideal flexibility for work-from-home needs, guests, or a potential fifth bedroom. Upstairs, you'll find three bedrooms including a private primary suite with its own balcony overlooking the deep backyard-the perfect spot for morning coffee. The spacious primary bath features double sinks, a separate shower, and soaking tub, while the two additional bedrooms share a hall bath. An oversized rooftop deck above the garage is an unexpected standout feature and adds even more outdoor living space. The finished lower level includes a recreation room with fireplace, a fourth bedroom, full bath, and bright laundry room. With four full bathrooms, thoughtful design, and major 2019 improvements including roof, windows, hot water heaters, kitchen & kitchen appliances, bathrooms, flooring, and stylish lighting throughout, this is a true move-in-ready home with a rare combination of size, style, attached garage, and oversized yard. Just move in and enjoy easy access to Nick Corwin Park, Hubbard Woods School, the train, and town.

1505 Tower Road, Winnetka

91 Abbottsford Road, Winnetka
$2,009,100
5 Beds ⋅ 5 Baths ⋅ 12611137 MLS ⋅ CLOSED Status
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.

91 Abbottsford Road, Winnetka

1423 Asbury Avenue, Winnetka
$2,237,500
6 Beds ⋅ 7 Baths ⋅ 12482150 MLS ⋅ CLOSED Status
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.

1423 Asbury Avenue, Winnetka

1523 Tower Road, Winnetka
$1,103,000
4 Beds ⋅ 3 Baths ⋅ 12620073 MLS ⋅ CLOSED Status
Meticulously maintained central-entry brick Colonial in the sought-after Hubbard Woods School District. Offering grand living spaces filled with natural light, this 4-bedroom, 3-bath home truly checks every box. A gracious foyer opens to the inviting living room, featuring a wood-burning fireplace, abundant windows, and custom built-in cabinetry. The separate dining room, with French doors leads to the sunroom and expansive professionally landscaped yard. The charming white kitchen has newer appliances and a planning desk, while a first-floor office is conveniently located adjacent to a full bath with shower. Upstairs, the luxe primary suite features a beautifully renovated bath with heated floors, a walk-in shower, and a heated towel rack. Three additional spacious bedrooms share an updated hall bath with tub. The lower level offers an expansive recreation room, new washer and dryer, and plenty of storage. A hard-to-find attached 2-car garage and generous driveway parking add to the home's appeal. Perfectly located across from Nick Corwin Park, just a short drive to the expressway, and within walking distance to town, this classic Winnetka combines timeless charm with spaces for today's lifestyle.

1523 Tower Road, Winnetka



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