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$334,000

Welcome to this charming brick Tudor duplex in Shaker Heights, where timeless character blends seamlessly with modern comfort. This picturesque two-family home offers a versatile opportunity—live in one unit while generating rental income from the other, or add a solid asset to your investment portfolio in a highly walkable neighborhood. The inviting first-floor unit features 2 bedrooms and 1 full bath, highlighted by gleaming hardwood floors, a classic fireplace, and an updated kitchen with granite countertops and included appliances. Upstairs, the expansive second unit spans two levels, offering 4 bedrooms and 2 full baths, along with a second fireplace and a beautifully remodeled (2026) kitchen featuring white cabinetry, quartz countertops, and stainless steel appliances. Recent updates enhance both style and functionality, including new carpet on the third floor (2024), refinished hardwood floors on the second floor (2024), and fresh paint throughout the second and third floors (2026). Each unit enjoys its own private sun deck—perfect for morning coffee or relaxing evenings—while original leaded glass windows add warmth and storybook charm throughout. Newer furnaces, central air systems, and hot water tanks provide peace of mind, complemented by a well-maintained detached garage. Ideally located, this home is just a short stroll to the vibrant Van Aken District for shopping and dining, with convenient access to public transit for an easy commute downtown. Schedule your private showing today! Point of Sale violations will be compliant prior to closing.

6 Beds ⋅ 3 Baths ⋅ 5202833 MLS

Welcome to this charming brick Tudor duplex in Shaker Heights, where timeless character blends seamlessly with modern comfort. This picturesque two-family home offers a versatile opportunity—live in one unit while generating rental income from the other, or add a solid asset to your investment portfolio in a highly walkable neighborhood. The inviting first-floor unit features 2 bedrooms and 1 full bath, highlighted by gleaming hardwood floors, a classic fireplace, and an updated kitchen with granite countertops and included appliances. Upstairs, the expansive second unit spans two levels, offering 4 bedrooms and 2 full baths, along with a second fireplace and a beautifully remodeled (2026) kitchen featuring white cabinetry, quartz countertops, and stainless steel appliances. Recent updates enhance both style and functionality, including new carpet on the third floor (2024), refinished hardwood floors on the second floor (2024), and fresh paint throughout the second and third floors (2026). Each unit enjoys its own private sun deck—perfect for morning coffee or relaxing evenings—while original leaded glass windows add warmth and storybook charm throughout. Newer furnaces, central air systems, and hot water tanks provide peace of mind, complemented by a well-maintained detached garage. Ideally located, this home is just a short stroll to the vibrant Van Aken District for shopping and dining, with convenient access to public transit for an easy commute downtown. Schedule your private showing today! Point of Sale violations will be compliant prior to closing.

18427 Winslow Road, Shaker Heights

Listing Courtesy of: Yinzhu Piao, yinzhu@kw.com With Keller Williams Greater Metropolitan

Selling Office: Keller Williams Greater Metropolitan.

$295,000

Welcome to this charming two-family home on one of Shaker Heights' most desirable streets - historic Winslow Road. This light-filled home features generous living rooms, formal dining rooms, and beautiful old-world style that is highly sought after in this particular area. The lower unit is tenant occupied, featuring 2 bedrooms and a full bathroom. The upper unit combines both the second and third floors with four bedrooms and two full bathrooms. This property has been thoughtfully maintained and recently upgraded with new front windows, a fully renovated bathroom, fresh carpeting, and updated appliances including a new fridge, washer, and dryer. Siding and gutters were also replaced in 2024, adding to the home's curb appeal and efficiency. Nestled in a quiet, tree-lined neighborhood with no through traffic, yet right by the vibrant Van Aken District, RTA Blue Line, Shaker Towne Center, Heinen's, and more. Only minutes to John Carroll University, Beachwood Place, Cleveland Clinic, and University Circle. A rare rental opportunity that combines space, charm, and unbeatable location.

6 Beds ⋅ 3 Baths ⋅ 5117886 MLS

Welcome to this charming two-family home on one of Shaker Heights' most desirable streets - historic Winslow Road. This light-filled home features generous living rooms, formal dining rooms, and beautiful old-world style that is highly sought after in this particular area. The lower unit is tenant occupied, featuring 2 bedrooms and a full bathroom. The upper unit combines both the second and third floors with four bedrooms and two full bathrooms. This property has been thoughtfully maintained and recently upgraded with new front windows, a fully renovated bathroom, fresh carpeting, and updated appliances including a new fridge, washer, and dryer. Siding and gutters were also replaced in 2024, adding to the home's curb appeal and efficiency. Nestled in a quiet, tree-lined neighborhood with no through traffic, yet right by the vibrant Van Aken District, RTA Blue Line, Shaker Towne Center, Heinen's, and more. Only minutes to John Carroll University, Beachwood Place, Cleveland Clinic, and University Circle. A rare rental opportunity that combines space, charm, and unbeatable location.

18412 Winslow Road, Shaker Heights

Listing Courtesy of: Alexis Thorpe, alexistherea@gmail.com With Keller Williams Living

Selling Office: Keller Williams Living.

$250,000

This two-family brick Tudor home is straight out of a storybook! As you approach, you'll be greeted by the warm, timeless allure of this picturesque dwelling. Step inside, and you'll find not one, but two delightful living spaces. The first-floor unit is a cozy haven, 2 bedrooms and 1 full bath. The hardwood floors gleam leading you to an original fireplace that's just perfect for curling up. The kitchen has been updated with granite countertop, appliances included! But wait, there's more! Venture upstairs to the second unit, spanning two stories and revealing 4 charming bedrooms and 2 full baths. The living room, complete with its own original fireplace, exudes a sense of history and comfort. The Kitchen has stainless appliances granite countertop and plenty of space. Both units have sun decks that beckon you to unwind with a good book and a cup of tea. The property's cherished leaded glass windows harken back to a bygone era, casting a soft, romantic glow. A well-kept detached garage ensures that your vehicles and treasures have a home of their own. And when it comes to keeping cozy, you're in good hands with younger furnaces and hot water tanks - ensuring warmth on even the chilliest of nights, and cool air in the hot summer days. With its blend of historic charm and modern conveniences, you'll feel like you've stepped into a magical world when you return home. Live in 1 and collect rent from the other. Walk to the Van Aken Transit line head downtown or walk to Shaker’s Van Aken District called the VAD.

6 Beds ⋅ 3 Baths ⋅ 5029460 MLS

This two-family brick Tudor home is straight out of a storybook! As you approach, you'll be greeted by the warm, timeless allure of this picturesque dwelling. Step inside, and you'll find not one, but two delightful living spaces. The first-floor unit is a cozy haven, 2 bedrooms and 1 full bath. The hardwood floors gleam leading you to an original fireplace that's just perfect for curling up. The kitchen has been updated with granite countertop, appliances included! But wait, there's more! Venture upstairs to the second unit, spanning two stories and revealing 4 charming bedrooms and 2 full baths. The living room, complete with its own original fireplace, exudes a sense of history and comfort. The Kitchen has stainless appliances granite countertop and plenty of space. Both units have sun decks that beckon you to unwind with a good book and a cup of tea. The property's cherished leaded glass windows harken back to a bygone era, casting a soft, romantic glow. A well-kept detached garage ensures that your vehicles and treasures have a home of their own. And when it comes to keeping cozy, you're in good hands with younger furnaces and hot water tanks - ensuring warmth on even the chilliest of nights, and cool air in the hot summer days. With its blend of historic charm and modern conveniences, you'll feel like you've stepped into a magical world when you return home. Live in 1 and collect rent from the other. Walk to the Van Aken Transit line head downtown or walk to Shaker’s Van Aken District called the VAD.

18427 Winslow Road, Shaker Heights

Listing Courtesy of: Bob Zimmer, rzimmer@kw.com With Keller Williams Greater Metropolitan

Selling Office: Howard Hanna.