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Situated in the desirable Greeley School District, this stunning 5-bedroom, 3.5-bath home is just one block from the lakefront and a short walk to charming downtown Winnetka. With over 4200sqft of above ground living space the fully finished basement is not included in the size! Designed for both style and function, the home showcases a chef's kitchen by Benvinuti & Stein with Viking, Sub-Zero, and Bosch appliances-perfect for everyday living and entertaining. No detail has been overlooked since the current owners moved in. Thoughtful upgrades include a complete remodel of the primary bath, new windows and flooring in the sun-filled all-seasons room, and a full lower-level renovation complete with a beautiful new laundry room. The second floor features three spacious bedrooms, while the third-floor loft offers incredible versatility with one bedroom, an office (or additional bedroom), a large living area, and a full bath. The 2.5-car garage includes built-out rooms above-ideal for storage, a playroom, or an art studio. This home combines timeless design, modern updates, and an unbeatable location near schools, shopping, dining, and the beach. All new mechanicals(hvac, ac 2023, new sump pump, new water heater, new windows in the sun room, the list goes on of upgrades.

4 Beds ⋅ 4 Baths ⋅ 12494483 MLS ⋅ CLOSED Status

Situated in the desirable Greeley School District, this stunning 5-bedroom, 3.5-bath home is just one block from the lakefront and a short walk to charming downtown Winnetka. With over 4200sqft of above ground living space the fully finished basement is not included in the size! Designed for both style and function, the home showcases a chef's kitchen by Benvinuti & Stein with Viking, Sub-Zero, and Bosch appliances-perfect for everyday living and entertaining. No detail has been overlooked since the current owners moved in. Thoughtful upgrades include a complete remodel of the primary bath, new windows and flooring in the sun-filled all-seasons room, and a full lower-level renovation complete with a beautiful new laundry room. The second floor features three spacious bedrooms, while the third-floor loft offers incredible versatility with one bedroom, an office (or additional bedroom), a large living area, and a full bath. The 2.5-car garage includes built-out rooms above-ideal for storage, a playroom, or an art studio. This home combines timeless design, modern updates, and an unbeatable location near schools, shopping, dining, and the beach. All new mechanicals(hvac, ac 2023, new sump pump, new water heater, new windows in the sun room, the list goes on of upgrades.

386 Fairview Avenue, Winnetka

$1,410,000

4 Beds ⋅ 4 Baths ⋅ 12419145 MLS ⋅ CLOSED Status

940 Forest Glen Drive, Winnetka

$4,200,000

Perfectly situated in a discreet upscale enclave east of Sheridan road. Beautifully tucked away is where you'll find this gorgeous estate on a professionally landscaped .659 acre. With exceptional quality, elegance and design throughout there are many updates that have been done over the last 3 years. Upon entering the foyer you'll see 12-14 ceilings and gorgeous marble floors. New Kitchen with state of the art appliances, an expansive island, a true Chef's dream with butler's pantry, Stainless steel Subzero appliances, Cristallo Quartzite counters, double sinks, an espresso bar, fireplace and lots of space for eat in kitchen. Brand new theater that rivals any that you've ever been to, gym, game room, a wine room that holds roughly 1000 bottles, completely renovated 3.5 car garage with custom dog grooming station, as well as a one year new outdoor kitchen made for entertaining with state of the art grill and pizza oven with custom limestone fireplace. The lower level has been designed to accommodate one's treasured art collection with special lighting to showcase your personal collection, plus 5th bedroom and bath. Master suite is enormous for his and hers spaces, fireplace & sitting area, a massive closet and dressing area with island, double sinks, steam shower, Jet tub and heated floors: a perfect oasis. All bedrooms are ensuite and quite large with generous closet space. Gorgeous outdoor areas can be found around the entire exterior of home on first and second floors, including a 2nd floor deck overlooking the beautifully landscaped yard offering spectacular views, with fireplace and plenty of room for couches and seating to enjoy those warmer summer evenings. Additional features include an elevator, heated flooring throughout, Control 4 security system, 8 fireplaces in total, a stunning warm and inviting library with sliding ladder, perfect to cozy up in and read that book you've had on your list. The magnificent staircase with custom iron railing leading up to 2nd floor with skylight above showcases the sophistication throughout that can be found within this very special home. This stunning property is not only high tech in many ways, it also caters to family living with so many new design features that allow for children and adults to have fun without ever leaving. A true statement property.

4 Beds ⋅ 7 Baths ⋅ 12444526 MLS ⋅ CLOSED Status

Perfectly situated in a discreet upscale enclave east of Sheridan road. Beautifully tucked away is where you'll find this gorgeous estate on a professionally landscaped .659 acre. With exceptional quality, elegance and design throughout there are many updates that have been done over the last 3 years. Upon entering the foyer you'll see 12-14 ceilings and gorgeous marble floors. New Kitchen with state of the art appliances, an expansive island, a true Chef's dream with butler's pantry, Stainless steel Subzero appliances, Cristallo Quartzite counters, double sinks, an espresso bar, fireplace and lots of space for eat in kitchen. Brand new theater that rivals any that you've ever been to, gym, game room, a wine room that holds roughly 1000 bottles, completely renovated 3.5 car garage with custom dog grooming station, as well as a one year new outdoor kitchen made for entertaining with state of the art grill and pizza oven with custom limestone fireplace. The lower level has been designed to accommodate one's treasured art collection with special lighting to showcase your personal collection, plus 5th bedroom and bath. Master suite is enormous for his and hers spaces, fireplace & sitting area, a massive closet and dressing area with island, double sinks, steam shower, Jet tub and heated floors: a perfect oasis. All bedrooms are ensuite and quite large with generous closet space. Gorgeous outdoor areas can be found around the entire exterior of home on first and second floors, including a 2nd floor deck overlooking the beautifully landscaped yard offering spectacular views, with fireplace and plenty of room for couches and seating to enjoy those warmer summer evenings. Additional features include an elevator, heated flooring throughout, Control 4 security system, 8 fireplaces in total, a stunning warm and inviting library with sliding ladder, perfect to cozy up in and read that book you've had on your list. The magnificent staircase with custom iron railing leading up to 2nd floor with skylight above showcases the sophistication throughout that can be found within this very special home. This stunning property is not only high tech in many ways, it also caters to family living with so many new design features that allow for children and adults to have fun without ever leaving. A true statement property.

977 Sheridan Road, Winnetka

$985,000

Estate-Owned Property in coveted Winnetka Location. Exceptional opportunity on a 9,000 sq ft lot (60 x 150) in one of Winnetka's most desirable neighborhoods. This home offers incredible potential. Renovate. Expand. Build new....up to approx. 3,600 sq ft (per current Village guidelines, to be confirmed by buyer). Ideal for downsizing or growing family...bring your ideas and plans and lets go! Make no mistake....this home needs it all, but the end result could be an enchanting bigger-than-it-looks cottage ready for another hundred years. Estate sale - property conveyed strictly as-is. Outstanding location: Close to Metra, downtown Winnetka, Lake Michigan, parks, trails, and shopping. Top-rated schools. This is a rare chance to build or reimagine in a premier North Shore setting! These sort of opportunities grow more and more rare by the day. *Current survey and required BMO rider are in additional info.*

3 Beds ⋅ 2 Baths ⋅ 12489126 MLS ⋅ CLOSED Status

Estate-Owned Property in coveted Winnetka Location. Exceptional opportunity on a 9,000 sq ft lot (60 x 150) in one of Winnetka's most desirable neighborhoods. This home offers incredible potential. Renovate. Expand. Build new....up to approx. 3,600 sq ft (per current Village guidelines, to be confirmed by buyer). Ideal for downsizing or growing family...bring your ideas and plans and lets go! Make no mistake....this home needs it all, but the end result could be an enchanting bigger-than-it-looks cottage ready for another hundred years. Estate sale - property conveyed strictly as-is. Outstanding location: Close to Metra, downtown Winnetka, Lake Michigan, parks, trails, and shopping. Top-rated schools. This is a rare chance to build or reimagine in a premier North Shore setting! These sort of opportunities grow more and more rare by the day. *Current survey and required BMO rider are in additional info.*

785 Locust Street, Winnetka

$2,460,000

Welcome to your serene oasis nestled on a private .85-acre lot in the heart of Winnetka. This enchanting home greets you with a gated drive and is surrounded by mature trees, offering unmatched privacy. Inside, the living room boasts a cozy fireplace, while the updated kitchen flows into a adjacent dining room. The family room, also with a fireplace, opens to a patio and spacious yard, offering exceptional views of the great outdoors. The first floor also features large mudroom (with Dutch door), laundry, and updated powder room. Upstairs, the luxurious primary suite offers a fireplace, renovated bath, and stunning views of the lush surrounds. Three additional bedrooms and a renovated hall bath complete this level. The third floor provides a versatile open space for endless possibilities for recreation, extra bedroom space or private office. Recent upgrades include new electrical and plumbing updates, a new roof and gutters (2023), and exterior painting (2022), with all bathrooms renovated in 2018. This charming home offers the potential to expand into your forever home or enjoy its timeless allure as it stands. Don't miss this extraordinary opportunity in a prime location.

4 Beds ⋅ 3 Baths ⋅ 12466389 MLS ⋅ CLOSED Status

Welcome to your serene oasis nestled on a private .85-acre lot in the heart of Winnetka. This enchanting home greets you with a gated drive and is surrounded by mature trees, offering unmatched privacy. Inside, the living room boasts a cozy fireplace, while the updated kitchen flows into a adjacent dining room. The family room, also with a fireplace, opens to a patio and spacious yard, offering exceptional views of the great outdoors. The first floor also features large mudroom (with Dutch door), laundry, and updated powder room. Upstairs, the luxurious primary suite offers a fireplace, renovated bath, and stunning views of the lush surrounds. Three additional bedrooms and a renovated hall bath complete this level. The third floor provides a versatile open space for endless possibilities for recreation, extra bedroom space or private office. Recent upgrades include new electrical and plumbing updates, a new roof and gutters (2023), and exterior painting (2022), with all bathrooms renovated in 2018. This charming home offers the potential to expand into your forever home or enjoy its timeless allure as it stands. Don't miss this extraordinary opportunity in a prime location.

1161 Pine Street, Winnetka

$2,945,000

4 Beds ⋅ 6 Baths ⋅ 12499553 MLS ⋅ CLOSED Status

1004 Oak Street, Winnetka

$3,600,000

Reminiscent of the timeless white painted Colonial retreats off the East Coast of Hyannis Port, this Winnetka estate set on 1.4 acres of gracious grounds captures that same coastal charm right here in the North Shore. Set on premier Woodley Road with a beautiful natural canopy of mature trees, this 8 beds, 5.2-bath home seamlessly blends grand entertaining with casual living through a quintessential floor plan designed for modern day living. Elegance unfolds the moment you step into the grand reception foyer crowned by a cascading wrought-iron staircase serving as the gateway to the home's formal spaces. Sunlit living room, anchored by a stately FP and framed by floor-to-ceiling windows, flows effortlessly into a dreamy sunroom wrapped in grasscloth wallpaper-offering serene views of the lush backyard. Tucked off the solarium a richly paneled library with FP creating the ultimate private retreat. Elegant dining room with French doors opening to the expansive terraces sets the stage for seamless indoor-outdoor entertaining. At the heart of the home is the expansive Chef's kitchen, designed for both culinary excellence & effortless hosting. Chefs' kitchen with great space, custom cabinetry, island with breakfast bar seating, desk command center, top of the line appliances, separate breakfast area, and fully loaded butler's pantry with wine fridge, sink, and custom cabinetry. Off the kitchen, Ralph Lauren-inspired family room w/ warm chestnut paneling, FP, bay window, and French doors opening to the bluestone patio & new tasteful in-ground spa. Thoughtfully designed mudroom with custom cabinetry connects to the heated 3 car garage, perfectly positioned as a discreet backdoor drop zone. Gracious 2nd floor is anchored by the private primary suite wing-offering a serene sanctuary with a spacious bedroom, sitting room with FP, and currently set up as his-and-her baths with an additional den (or bedroom). 3 additional ensuite bedrooms on this level, one tucked away on the north wing with a light-filled art studio. Fully equipped 2nd floor laundry also on this level. Third floor with soaring ceilings, large rec space, and three oversized bedrooms with a full bath offer endless possibilities. The lower level provides even more versatility, with a spacious rec room/gym, custom wine cellar, and ample storage. From inside to out, 5 Woodley is an all American classic that always continues to only get better with time. This is a phenomenal opportunity to take this graceful & solidly built home to a new level of 2025 luxury.

8 Beds ⋅ 7 Baths ⋅ 12452300 MLS ⋅ CLOSED Status

Reminiscent of the timeless white painted Colonial retreats off the East Coast of Hyannis Port, this Winnetka estate set on 1.4 acres of gracious grounds captures that same coastal charm right here in the North Shore. Set on premier Woodley Road with a beautiful natural canopy of mature trees, this 8 beds, 5.2-bath home seamlessly blends grand entertaining with casual living through a quintessential floor plan designed for modern day living. Elegance unfolds the moment you step into the grand reception foyer crowned by a cascading wrought-iron staircase serving as the gateway to the home's formal spaces. Sunlit living room, anchored by a stately FP and framed by floor-to-ceiling windows, flows effortlessly into a dreamy sunroom wrapped in grasscloth wallpaper-offering serene views of the lush backyard. Tucked off the solarium a richly paneled library with FP creating the ultimate private retreat. Elegant dining room with French doors opening to the expansive terraces sets the stage for seamless indoor-outdoor entertaining. At the heart of the home is the expansive Chef's kitchen, designed for both culinary excellence & effortless hosting. Chefs' kitchen with great space, custom cabinetry, island with breakfast bar seating, desk command center, top of the line appliances, separate breakfast area, and fully loaded butler's pantry with wine fridge, sink, and custom cabinetry. Off the kitchen, Ralph Lauren-inspired family room w/ warm chestnut paneling, FP, bay window, and French doors opening to the bluestone patio & new tasteful in-ground spa. Thoughtfully designed mudroom with custom cabinetry connects to the heated 3 car garage, perfectly positioned as a discreet backdoor drop zone. Gracious 2nd floor is anchored by the private primary suite wing-offering a serene sanctuary with a spacious bedroom, sitting room with FP, and currently set up as his-and-her baths with an additional den (or bedroom). 3 additional ensuite bedrooms on this level, one tucked away on the north wing with a light-filled art studio. Fully equipped 2nd floor laundry also on this level. Third floor with soaring ceilings, large rec space, and three oversized bedrooms with a full bath offer endless possibilities. The lower level provides even more versatility, with a spacious rec room/gym, custom wine cellar, and ample storage. From inside to out, 5 Woodley is an all American classic that always continues to only get better with time. This is a phenomenal opportunity to take this graceful & solidly built home to a new level of 2025 luxury.

5 Woodley Road, Winnetka

$610,000

Refreshed and upgraded with new paint throughout, new roof, new garage door and new lighting at a new price! Nestled in the heart of Winnetka and within the highly sought-after New Trier School District, this updated 3-bedroom, 2.1-bath end unit townhouse offers a rare combination of space, design, and walkability. The main level welcomes you with an abundance of natural light and an airy, open layout ideal for everyday living and entertaining. The newer kitchen updated in 2024 impresses with quartz countertops, excellent cabinet storage, and sleek stainless steel appliances. Both the living room and dining room feature sliding glass doors that lead to a private backyard patio-perfect for summer gatherings or morning coffee outdoors. The first floor also includes a powder room, and laundry room. Upstairs, the primary suite is a true retreat, complete with generous closets and an en-suite bathroom. Two additional bedrooms and a full hall bath with a tub round out the second floor. Additional highlights include a detached garage, attic storage, newer A/C, newer windows and a location that simply can't be beat-walk to the Metra, schools, parks, dining, shops, and the lakefront. With style, function, and convenience all in one, this move-in ready home offers the best of North Shore living.

3 Beds ⋅ 3 Baths ⋅ 12489453 MLS ⋅ CLOSED Status

Refreshed and upgraded with new paint throughout, new roof, new garage door and new lighting at a new price! Nestled in the heart of Winnetka and within the highly sought-after New Trier School District, this updated 3-bedroom, 2.1-bath end unit townhouse offers a rare combination of space, design, and walkability. The main level welcomes you with an abundance of natural light and an airy, open layout ideal for everyday living and entertaining. The newer kitchen updated in 2024 impresses with quartz countertops, excellent cabinet storage, and sleek stainless steel appliances. Both the living room and dining room feature sliding glass doors that lead to a private backyard patio-perfect for summer gatherings or morning coffee outdoors. The first floor also includes a powder room, and laundry room. Upstairs, the primary suite is a true retreat, complete with generous closets and an en-suite bathroom. Two additional bedrooms and a full hall bath with a tub round out the second floor. Additional highlights include a detached garage, attic storage, newer A/C, newer windows and a location that simply can't be beat-walk to the Metra, schools, parks, dining, shops, and the lakefront. With style, function, and convenience all in one, this move-in ready home offers the best of North Shore living.

730 Oak Street, Winnetka

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