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Steeped in history and beautifully reimagined for modern living, this magnificent Captain's Mansion, dating to 1892, offers a rare opportunity to own a piece of Fort Sheridan's distinguished architectural heritage. Located just three homes from Lake Michigan within the National Historic Landmark District, this exceptional 7,654-square-foot residence seamlessly blends the grandeur and craftsmanship of the late 19th century with extensive contemporary renovations. Soaring ceilings, sun-filled interiors, hardwood floors, two staircases, multiple fireplaces, and seasonal lake views create an extraordinary setting for everyday living and entertaining. A gracious foyer introduces the home's impressive scale and timeless elegance, opening to a beautiful living room with fireplace and a formal dining room, both featuring stunning 11-foot ceilings. The newly redesigned gourmet kitchen combines style and functionality with updated cabinetry, quartz countertops, a generous center island, new stainless steel Wolf double ovens and cooktop, a new Sub Zero refrigerator, and a spacious pantry with a beverage bar and abundant storage. The expansive family room addition offers exceptional gathering space with direct access to a new Trex composite patio and fenced side yard. The second floor features three spacious ensuite bedrooms, including a luxurious primary suite with an oversized custom walk-in closet and a newly renovated spa-inspired bathroom featuring radiant heated floors, quartz countertops, a spacious shower, Jacuzzi tub, and heated towel rack. A comfortable loft and conveniently located laundry room complete this level. The versatile third floor offers a spacious second family room and two additional rooms ideal for bedrooms, home offices, or flexible living spaces. The finished lower level provides even more room to spread out, with a recreation room, additional bedroom, full bathroom, and second laundry room. Extensive recent improvements enhance the home's comfort and functionality, including three new HVAC and air conditioning systems (2025), electrical upgrades, new lower-level luxury vinyl flooring, screen doors, sprinkler system, custom mudroom closets, and window treatments. Freshly painted interiors and an attached three-car garage further complement this exceptional, move-in-ready residence. Originally part of the historic Fort Sheridan military installation, this remarkable home offers the rare opportunity to experience the architectural character and grandeur of a bygone era without sacrificing modern comforts. Surrounded by the natural beauty of Lake Michigan, scenic walking trails, and historic architecture, Fort Sheridan offers a distinctive lifestyle just minutes from the restaurants and shops of Highwood, Highland Park, and Lake Forest, with convenient access to Metra and downtown Chicago. An extraordinary combination of history, architectural beauty, generous living spaces, and modern luxury in one of the North Shore's most distinctive settings.

6 Beds ⋅ 7 Baths ⋅ 12770627 MLS ⋅ NEW Status

Steeped in history and beautifully reimagined for modern living, this magnificent Captain's Mansion, dating to 1892, offers a rare opportunity to own a piece of Fort Sheridan's distinguished architectural heritage. Located just three homes from Lake Michigan within the National Historic Landmark District, this exceptional 7,654-square-foot residence seamlessly blends the grandeur and craftsmanship of the late 19th century with extensive contemporary renovations. Soaring ceilings, sun-filled interiors, hardwood floors, two staircases, multiple fireplaces, and seasonal lake views create an extraordinary setting for everyday living and entertaining. A gracious foyer introduces the home's impressive scale and timeless elegance, opening to a beautiful living room with fireplace and a formal dining room, both featuring stunning 11-foot ceilings. The newly redesigned gourmet kitchen combines style and functionality with updated cabinetry, quartz countertops, a generous center island, new stainless steel Wolf double ovens and cooktop, a new Sub Zero refrigerator, and a spacious pantry with a beverage bar and abundant storage. The expansive family room addition offers exceptional gathering space with direct access to a new Trex composite patio and fenced side yard. The second floor features three spacious ensuite bedrooms, including a luxurious primary suite with an oversized custom walk-in closet and a newly renovated spa-inspired bathroom featuring radiant heated floors, quartz countertops, a spacious shower, Jacuzzi tub, and heated towel rack. A comfortable loft and conveniently located laundry room complete this level. The versatile third floor offers a spacious second family room and two additional rooms ideal for bedrooms, home offices, or flexible living spaces. The finished lower level provides even more room to spread out, with a recreation room, additional bedroom, full bathroom, and second laundry room. Extensive recent improvements enhance the home's comfort and functionality, including three new HVAC and air conditioning systems (2025), electrical upgrades, new lower-level luxury vinyl flooring, screen doors, sprinkler system, custom mudroom closets, and window treatments. Freshly painted interiors and an attached three-car garage further complement this exceptional, move-in-ready residence. Originally part of the historic Fort Sheridan military installation, this remarkable home offers the rare opportunity to experience the architectural character and grandeur of a bygone era without sacrificing modern comforts. Surrounded by the natural beauty of Lake Michigan, scenic walking trails, and historic architecture, Fort Sheridan offers a distinctive lifestyle just minutes from the restaurants and shops of Highwood, Highland Park, and Lake Forest, with convenient access to Metra and downtown Chicago. An extraordinary combination of history, architectural beauty, generous living spaces, and modern luxury in one of the North Shore's most distinctive settings.

41 Scott Loop, Highland Park

240 Whistler Road Unit #1E, Highland Park

$2,100,000

Built in 1893 and designed by the celebrated Chicago firm Holabird & Roche, this landmark building in the heart of Fort Sheridan began its life as the Infantry Drill Hall and later served as the post gymnasium. Today it holds just 11 distinctive condominiums, and this end unit is one of its most special. With exposures to the east, north, and south, the home is filled with light throughout the day. The building's original wide, arched entrance on the east facade has been reimagined as a dramatic wall of windows, a striking reminder of the building's history. The kitchen pairs clean, contemporary design with serious function, including a Sub-Zero refrigerator and freezer, a Bosch dishwasher, and a six-burner FiveStar range with two ovens. A large marble island with a breakfast bar is the natural gathering spot, and the eating area beside it is surrounded by floor-to-ceiling windows. The kitchen opens to the family room, where 16-foot ceilings and walls of glass lead out to a 38-foot balcony overlooking the meadow and stream, a lovely place to start the morning or unwind at the end of the day. The primary suite has 13-foot ceilings, floor-to-ceiling windows, and its own balcony facing the historic water tower. The primary bath includes a walk-in shower, whirlpool tub, separate Toto toilet room, makeup vanity, and walk-in closet. One of many large closets, professionally built out, throughout the home. The lower level offers remarkable flexibility, with a family room lit by 25 feet of windows, two more bedrooms, two baths, an exercise area, a bonus room and workshop, ideal for guests, a home office, or extended family. Everyday living is easy here, with an elevator just outside the front door, all primary living spaces on the main level, and four assigned spaces in the attached heated garage. Step outside to gravel walking paths and head east for views of Lake Michigan, plus you're just a short walk from Highwood's restaurants, festivals, and food trucks in the park. A rare chance to own a piece of North Shore history, beautifully suited to how we live today.

5 Beds ⋅ 6 Baths ⋅ 12791592 MLS ⋅ NEW Status ⋅ Fort Sheridan BLDG.

Built in 1893 and designed by the celebrated Chicago firm Holabird & Roche, this landmark building in the heart of Fort Sheridan began its life as the Infantry Drill Hall and later served as the post gymnasium. Today it holds just 11 distinctive condominiums, and this end unit is one of its most special. With exposures to the east, north, and south, the home is filled with light throughout the day. The building's original wide, arched entrance on the east facade has been reimagined as a dramatic wall of windows, a striking reminder of the building's history. The kitchen pairs clean, contemporary design with serious function, including a Sub-Zero refrigerator and freezer, a Bosch dishwasher, and a six-burner FiveStar range with two ovens. A large marble island with a breakfast bar is the natural gathering spot, and the eating area beside it is surrounded by floor-to-ceiling windows. The kitchen opens to the family room, where 16-foot ceilings and walls of glass lead out to a 38-foot balcony overlooking the meadow and stream, a lovely place to start the morning or unwind at the end of the day. The primary suite has 13-foot ceilings, floor-to-ceiling windows, and its own balcony facing the historic water tower. The primary bath includes a walk-in shower, whirlpool tub, separate Toto toilet room, makeup vanity, and walk-in closet. One of many large closets, professionally built out, throughout the home. The lower level offers remarkable flexibility, with a family room lit by 25 feet of windows, two more bedrooms, two baths, an exercise area, a bonus room and workshop, ideal for guests, a home office, or extended family. Everyday living is easy here, with an elevator just outside the front door, all primary living spaces on the main level, and four assigned spaces in the attached heated garage. Step outside to gravel walking paths and head east for views of Lake Michigan, plus you're just a short walk from Highwood's restaurants, festivals, and food trucks in the park. A rare chance to own a piece of North Shore history, beautifully suited to how we live today.

240 Whistler Road Unit #1E, Highland Park

$649,000

Discover a distinctive blend of historic character and modern sophistication in this exceptional three-story townhome nestled within the storied Fort Sheridan community along Lake Michigan. An open floor plan, two spacious bedrooms, and two and a half bathrooms create an inviting setting for both everyday living and entertaining. The updated kitchen is beautifully appointed with granite countertops, and a center island, while updated bathrooms offer contemporary style and comfort. Architectural appeal shines through in the dramatic ceiling heights, with 10-foot ceilings on the second floor and soaring 11-foot ceilings on the third, featuring arched windows on the top level. A wooden deck extends the living space outdoors, and a two-car garage and dedicated utility room provide added convenience. Enjoy the distinctive Fort Sheridan lifestyle, where historic surroundings meet the natural beauty of Lake Michigan. Explore nearby scenic trails and lakefront vistas, catch the train at the Fort Sheridan Metra station, or stop by Starbucks just moments away. A rare opportunity to enjoy refined, low-maintenance living in one of the North Shore's most distinctive historic communities.

2 Beds ⋅ 3 Baths ⋅ 12785449 MLS ⋅ ACTIVE Status ⋅ Fort Sheridan BLDG.

Discover a distinctive blend of historic character and modern sophistication in this exceptional three-story townhome nestled within the storied Fort Sheridan community along Lake Michigan. An open floor plan, two spacious bedrooms, and two and a half bathrooms create an inviting setting for both everyday living and entertaining. The updated kitchen is beautifully appointed with granite countertops, and a center island, while updated bathrooms offer contemporary style and comfort. Architectural appeal shines through in the dramatic ceiling heights, with 10-foot ceilings on the second floor and soaring 11-foot ceilings on the third, featuring arched windows on the top level. A wooden deck extends the living space outdoors, and a two-car garage and dedicated utility room provide added convenience. Enjoy the distinctive Fort Sheridan lifestyle, where historic surroundings meet the natural beauty of Lake Michigan. Explore nearby scenic trails and lakefront vistas, catch the train at the Fort Sheridan Metra station, or stop by Starbucks just moments away. A rare opportunity to enjoy refined, low-maintenance living in one of the North Shore's most distinctive historic communities.

155 Whistler Road, Highland Park

$699,999

Step into this completely renovated (by homeowner) and beautifully appointed Fort Sheridan townhome and prepare to be mesmerized. An unobstructed park view sets the stage for this exceptional home, where 11-foot ceilings, sophisticated design, and state-of-the-art technology come together to create a truly one-of-a-kind living experience. The home has been thoughtfully opened up to create an airy, light-filled floor plan. The first floor features stunning chevron-patterned flooring, a sleek linear modern gas fireplace, and a spectacular custom kitchen. Designed for both everyday living and entertaining, the kitchen showcases 6-foot custom white oak cabinetry, an extra-wide drawer system, a 7-foot island with integrated wine refrigerator and microwave, and gorgeous quartz countertops with a waterfall edge. Additional details include a reverse-osmosis water purification system, under-cabinet toe-kick lighting, and a custom white oak banquette with integrated storage. Even the powder room is gorgeous with hand made cement Moroccan tiles. Smart-home technology is seamlessly integrated throughout, including Lutron Caseta lighting, Sonos surround sound and built-in speakers, and motorized Hunter Douglas window shades. Every detail has been considered, including modern HVAC registers, contemporary outlets with USB-A/C charging ports, and sleek screwless switch plates. Ascend the custom white oak staircase to the second floor, where beautifully appointed bedrooms feature custom wall paneling, spacious closets, extra-wide French doors, and 2 gorgeous bathrooms outfitted with Kohler fixtures. The primary suite offers a generous walk-in closet and a luxurious walk-in shower with floor-to-ceiling tile. The lower level provides exceptional functionality with a new washer and dryer, floating laundry folding cabinet, abundant additional storage, and an epoxy-floored attached two-car garage. Nothing has been overlooked in this extraordinary renovation. Sophisticated, stylish, and exceptionally well executed, this is an effortless way of life in one of the North Shore's most special settings. Living in Fort Sheridan is truly paradise-nestled along Lake Michigan and surrounded by ravines, preserves, and natural beauty. Enjoy beach access, scenic trails, and close proximity to downtown Highwood, Highland Park, and Lake Forest, with an easy commute to Chicago. A rare opportunity to enjoy beautifully designed, completely renovated living in the heart of Fort Sheridan.

2 Beds ⋅ 3 Baths ⋅ 12781749 MLS ⋅ ACTIVE Status

Step into this completely renovated (by homeowner) and beautifully appointed Fort Sheridan townhome and prepare to be mesmerized. An unobstructed park view sets the stage for this exceptional home, where 11-foot ceilings, sophisticated design, and state-of-the-art technology come together to create a truly one-of-a-kind living experience. The home has been thoughtfully opened up to create an airy, light-filled floor plan. The first floor features stunning chevron-patterned flooring, a sleek linear modern gas fireplace, and a spectacular custom kitchen. Designed for both everyday living and entertaining, the kitchen showcases 6-foot custom white oak cabinetry, an extra-wide drawer system, a 7-foot island with integrated wine refrigerator and microwave, and gorgeous quartz countertops with a waterfall edge. Additional details include a reverse-osmosis water purification system, under-cabinet toe-kick lighting, and a custom white oak banquette with integrated storage. Even the powder room is gorgeous with hand made cement Moroccan tiles. Smart-home technology is seamlessly integrated throughout, including Lutron Caseta lighting, Sonos surround sound and built-in speakers, and motorized Hunter Douglas window shades. Every detail has been considered, including modern HVAC registers, contemporary outlets with USB-A/C charging ports, and sleek screwless switch plates. Ascend the custom white oak staircase to the second floor, where beautifully appointed bedrooms feature custom wall paneling, spacious closets, extra-wide French doors, and 2 gorgeous bathrooms outfitted with Kohler fixtures. The primary suite offers a generous walk-in closet and a luxurious walk-in shower with floor-to-ceiling tile. The lower level provides exceptional functionality with a new washer and dryer, floating laundry folding cabinet, abundant additional storage, and an epoxy-floored attached two-car garage. Nothing has been overlooked in this extraordinary renovation. Sophisticated, stylish, and exceptionally well executed, this is an effortless way of life in one of the North Shore's most special settings. Living in Fort Sheridan is truly paradise-nestled along Lake Michigan and surrounded by ravines, preserves, and natural beauty. Enjoy beach access, scenic trails, and close proximity to downtown Highwood, Highland Park, and Lake Forest, with an easy commute to Chicago. A rare opportunity to enjoy beautifully designed, completely renovated living in the heart of Fort Sheridan.

271 Whistler Road, Highland Park

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