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381 Linden Street, Winnetka
$1,599,000
4 Beds ⋅ 3 Baths ⋅ 12806007 MLS ⋅ NEW Status
FIRST FLOOR BEDROOMS - WALK TO TOWN - A RARE opportunity to enjoy effortless living in one of Winnetka's most beloved neighborhoods. Nestled in mature landscaping and enchanting gardens, this beautifully maintained home offers the perfect blend of comfort, charm, and convenience. Thoughtfully designed for today's lifestyle, the flexible floor plan features two sought-after first-floor bedrooms, creating exceptional accessibility and ease for those seeking single-level living without sacrificing space, plus two more bedrooms on the second floor. A circular floorplan that offers flexibility with a separate dining room, living room, family room and eat-in kitchen. Sun-filled living spaces flow seamlessly from room to room, creating an inviting atmosphere for both everyday living and entertaining. Large picture windows and skylights frame lush garden views at every turn, bringing the beauty of the outdoors inside. Outside, winding pathways, blue stone terraces, private seating areas, and hidden garden retreats create a serene sanctuary that feels worlds away from the everyday. The location is simply exceptional. Leave the car behind and enjoy a truly walkable lifestyle with easy access to Winnetka's vibrant village center, coffee shops, restaurants, boutiques, parks, schools, and the Metra. Stroll to neighborhood favorites, meet friends for dinner, browse local shops, or enjoy a morning walk through the tree-lined streets. This home truly offers a lifestyle that is as effortless as it is exceptional. A hidden gem where timeless charm, privacy, and convenience come together in the heart of Winnetka.

381 Linden Street, Winnetka

1390 Scott Avenue, Winnetka
$1,975,000
6 Beds ⋅ 5 Baths ⋅ 12795446 MLS ⋅ NEW Status
This special Hubbard Woods home was saved & thoughtfully restored by caring long time Winnetka residents who didn't want to see this classic beauty turned into another cookie-cutter new construction. After teaming up with a top local architect/builder, a two+ year, no expense spared, gut renovation brought this handsome, center-entry brick colonial back to its former glory with no expense spared! The interior is ALL NEW CONSTRUCTION including electric, plumbing, windows, roof, flooring, lighting, kitchen/baths, insulation, layout, heating, cooling, and the list goes on and on! Six well appointed bedrooms, five (3.2) beautiful new bathrooms, with four floors + over 4,000 sq ft of stunning new construction living space. The corner lot on sought-after Scott Ave allows for natural light to flow in throughout the day. The Chef's kitchen is magazine worthy with custom cabinets, 9' island, top-of-the-line appliances & fixtures. This extends to the bar area conveniently open to the dining room. A mudroom is conveniently near the back door off the kitchen. The spacious living room features a cozy fireplace & opens to the sunroom/den. The sunroom has french doors that lead you to the bluestone patio area & large backyard. The second floor features four well appointed bedrooms, a laundry room and two full bathrooms. The primary suite is a dream with a spa-like Italian marble bathroom. The third floor features the 5th and 6th bedroom, as well as another gorgeous full bathroom. The large finished basement has two rec room areas, a second laundry room & half bath. The home currently has a one-car attached garage but an additional two-car detached garage has been fully permitted & is slated to break ground prior to the holidays!! This magical location has it all; walkable to downtown Hubbard Woods, restaurants, shops, train, Nick Corwin park & the best Halloween celebrations in town! Award winning Hubbard woods elementary school & New Trier. This home truly has the BEST of both worlds with the solid bones of an older home, while also having the new modern amenities & systems of a brand new construction.

1390 Scott Avenue, Winnetka

795 Pine Street, Winnetka
$3,499,000
6 Beds ⋅ 7 Baths ⋅ 12797319 MLS ⋅ ACTIVE Status
Extraordinary luxury new construction in a prime Winnetka location, with anticipated completion Summer 2027. Set on over a quarter acre, this exceptional residence will offer approximately 5,500 square feet with 8 bedrooms, each offering en-suite bath access, and 7 baths, blending elevated craftsmanship, timeless finishes, and thoughtful design for sophisticated yet comfortable living. Soaring 9'6" ceilings, engineered hardwood flooring, and designer ceiling details create an impressive backdrop for beautifully appointed interiors. The chef's kitchen will feature Sub-Zero and Wolf appliances, custom cabinetry, quartz countertops, a 10-foot island with seating, and a fully equipped butler's pantry with wine refrigeration. Opening seamlessly to the family room with a custom fireplace and built-ins, this inviting gathering space is designed for effortless everyday living and entertaining. A dramatic 12-foot folding door system connects the interior to the backyard, creating an exceptional indoor-outdoor living experience. An attached two-car garage with an EV charger adds modern convenience. Ideally located moments from downtown Winnetka, the train, parks, schools, and Lake Michigan. A rare opportunity to personalize finishes and create your dream home in an outstanding North Shore setting. Please note: Interior photos showcase the builder's previous project.

795 Pine Street, Winnetka

1097 Merrill Street Unit #G2, Winnetka
$285,000
2 Beds ⋅ 1 Baths ⋅ 12784655 MLS ⋅ ACTIVE Status
Rarely available and ideally located in the heart of Hubbard Woods, this charming 2-bedroom, 1-bath condo is the largest unit in Winnetka Manor. Just steps from the Metra, shops, restaurants, parks, Lake Michigan, and the bike path, this home offers an exceptional blend of character, comfort, and convenience. The inviting layout featuring a spacious living room, separate dining room, and two generous bedrooms. Hardwood floors, fresh neutral paint, and abundant natural light enhance the timeless appeal. The updated kitchen features granite countertops and stainless-steel appliances, while the refreshed bath, decorative fireplace mantel, California Closets throughout, and a walk-in primary closet add thoughtful touches. Winnetka Manor is a well-maintained community. Terrific move-in-ready home!

1097 Merrill Street Unit #G2, Winnetka

1288 Sunview Lane, Winnetka
$1,995,000
5 Beds ⋅ 5 Baths ⋅ 12786632 MLS ⋅ ACTIVE Status
Completely redesigned from top to bottom, this home offers the feel of new construction while preserving the character of the original property. The floor plan includes 5 bedrooms, 3 full baths, and 2 half baths, with four bedrooms upstairs and a main-level bedroom with ensuite that works as a guest suite or second primary. The main floor flows easily between living, dining, kitchen, and family spaces, with two masonry fireplaces, a second family room, and a dedicated office. A fully finished basement adds recreation space, laundry, and storage, and a second laundry is located on the bedroom level. Outdoor living includes a large rear patio, generous backyard, and rooftop deck. The half-acre lot provides rare outdoor space in this Winnetka setting. Additional features include a two-car garage with EV charging and hardwood flooring throughout. Minutes from New Trier, Skokie Playfields, downtown shopping and dining, Metra, and the lakefront, 1288 Sunview is a rare combination of thoughtful design, substantial space, and an exceptional lot.

1288 Sunview Lane, Winnetka

510 Ash Street, Winnetka
$1,995,000
12780362 MLS ⋅ ACTIVE Status
A rare offering on one of East Winnetka's most desirable streets, just two blocks from Lake Michigan. This exceptional property presents a unique opportunity to either thoughtfully renovate an existing home or create a custom residence with the potential for approximately 8,400 square feet of finished living space. Set on a beautiful, private lot surrounded by lush greenery, the property offers the perfect canvas for reimagining a home in an extraordinary setting. With no comparable lots currently available, and neighboring properties valued at over $5 million, the possibilities are truly exceptional. Enjoy an easy walk to downtown Winnetka, Greeley School, New Trier High School, the Metra train, Lake Michigan, parks and more. A rare opportunity to bring your vision to life in an unmatched location, whether through a beautiful renovation or a custom new build. Existing home is sold as-is, with no inspections.

510 Ash Street, Winnetka

510 Ash Street, Winnetka
$1,995,000
5 Beds ⋅ 3 Baths ⋅ 12775682 MLS ⋅ ACTIVE Status
A rare offering on one of East Winnetka's most desirable streets, just two blocks from Lake Michigan. This exceptional property presents a unique opportunity to either thoughtfully renovate an existing home or create a custom residence with the potential for approximately 8,400 square feet of finished living space. Set on a beautiful, private lot surrounded by lush greenery, the property offers the perfect canvas for reimagining a home in an extraordinary setting. With no comparable lots currently available, and neighboring properties valued at over $5 million, the possibilities are truly exceptional. Enjoy an easy walk to downtown Winnetka, Greeley School, New Trier High School, the Metra train, Lake Michigan, parks and more. A rare opportunity to bring your vision to life in an unmatched location, whether through a beautiful renovation or a custom new build. Existing home is sold as-is, with no inspections.

510 Ash Street, Winnetka

61 Woodley Road, Winnetka
$2,595,000
12213495 MLS ⋅ ACTIVE Status
Discover a once-in-a-lifetime opportunity to build your dream estate in one of the North Shore's most coveted neighborhoods. Situated on prestigious Woodley Road in Winnetka, this rarely available 1.45-acre property offers an extraordinary canvas for creating a truly exceptional residence. The existing home has already been demolished, leaving this premier homesite shovel-ready. Bring your own architect and builder, or take advantage of thoughtfully designed plans already in the final stages of the permitting process. With multiple PINs and over 63,000 square feet of land, the possibilities are endless. This property presents the rare opportunity to create a private estate with unparalleled scale, luxury, and privacy. Nestled among some of the North Shore's finest homes, the setting perfectly balances serene seclusion with everyday convenience. Located within the nationally acclaimed New Trier High School District, the property is just minutes from the boutiques, restaurants, and amenities of both Winnetka and Wilmette. Bring your vision and your grandest ideas to this remarkable offering.

61 Woodley Road, Winnetka

82 Woodley Road, Winnetka
$2,699,000
6 Beds ⋅ 6 Baths ⋅ 12680099 MLS ⋅ ACTIVE Status
Tucked away on one of Winnetka's most prestigious and serene lanes, this estate offers a rare blend of timeless North Shore elegance and a sense of true sanctuary. This isn't just a home; it's a sprawling residence designed for a lifestyle of both grand-scale entertaining and quiet, sun-drenched mornings. From the moment you pull up the winding drive, the home's commanding presence and lush, manicured grounds set the stage. Inside, the craftsmanship is unmistakable. You'll find expansive living spaces defined by rich architectural details and massive windows that frame the private, park-like backyard. The chef's kitchen is a masterpiece of function and style, flowing effortlessly into inviting family spaces that feel warm despite their scale. A first floor bedroom includes a private full bath and access to the patio. The primary suite serves as a genuine retreat, complete with a spa bath and enough closet space to satisfy any wardrobe. A sitting area surrounded by windows and a walkout overlooks the exquisite property. Each additional bedroom is en-suite and generously sized, ensuring everyone has their own corner of comfort. The third level includes flexible space with 3 lovely rooms and a full bath. There is an extra bonus space above the attached garage-perfect for a studio! Outside, the property truly shines. The expansive patio and rolling lawns create an incredible backdrop for summer garden parties or a quiet evening under the stars. Living here means more than just enjoying a beautiful residence; it's about the Winnetka lifestyle. You're minutes away from world-class schools, boutique shopping in the village, the shores of Lake Michigan, and the Metra for an easy commute to the city. It's sophisticated, it's private, and it's ready for its next chapter.

82 Woodley Road, Winnetka

62 Woodley Road, Winnetka
$2,569,900
6 Beds ⋅ 6 Baths ⋅ 12637769 MLS ⋅ ACTIVE Status
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.

62 Woodley Road, Winnetka



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