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19208 Chagrin, Shaker Heights
$375,000
6 Beds ⋅ 4 Baths ⋅ 5252900 MLS
BACK ON THE MARKET AT NO FAULT OF THE SELLERS! Incredible opportunity to own a spacious, income producing 2-family property in a prime Shaker Heights location. The property is a short walk from the shops, restaurants, and entertainment of the Van Aken District and within the highly desirable Shaker Heights school district. Valid POS certificate through 2028. An inspection report is available upon an accepted offer. FHA and VA buyers are welcome! Whether you're looking to live in one unit while the other helps pay your mortgage or add a turnkey income property to your portfolio, this duplex offers excellent flexibility. Situated on a beautiful, tree lined corner lot, this classic brick colonial features two units, each with its own street address and private front entrance. The upper unit enters from Chagrin, while the lower enters from Storer, both units have central air. The rear hallway, staircase, back entrance, and basement are shared.The lower unit is a fully remodeled 3 bedroom, 1.5 bath residence, while the upper unit is a newly updated 3 bedroom, 2 full bath residence that is vacant and move in ready. Both units feature spacious living areas, fireplaces, and hardwood floors throughout. The property offers a three car garage, generous storage, and separate laundry facilities for each unit. A large basement bonus room provides additional flexibility for a home office, gym, or recreation space. Gas and electric are separately metered and paid directly by tenants, leaving water and sewer as the owner's only recurring utility expenses. Lower unit is currently rented for $1,700 per month to a reliable tenant, approximately $300 below market value. The upper unit has an estimated market rental value of $2,200 per month. At current rents, the property offers approximately $3,900 in monthly income. Once the lower unit reaches market rent, the property could generate approximately $4,200 per month, or $50,400 annually. Schedule your private showing today!

19208 Chagrin, Shaker Heights

3624 Rolliston Road, Shaker Heights
$354,900
6 Beds ⋅ 3 Baths ⋅ 5247982 MLS
At 3,415 square feet with 6 bedrooms and 3 full baths, 3624 Rolliston Road offers something that can be hard to find in the Shaker Heights multi-family market. Generous space, classic character, and extensive updates already completed. At just $107 per square foot, there is a lot of finished, move-in-ready home here for the money. Inside, you’ll find the beautiful original hardwood floors, distinctive front windows, and spacious rooms that give Shaker Heights homes so much of their charm. But this one brings plenty of modern updates along with that character. Both kitchens and all three full bathrooms have been beautifully renovated, while major improvements include a new roof, two new furnaces, new hot water tanks, new plumbing, and updated electrical. The second-floor unit offers even more flexibility, continuing to the third floor with two additional bedrooms and a bonus space that could easily become a home office, playroom, workout room or whatever fits your needs. Each unit also enjoys its own outdoor space, with a deck for the lower unit and a balcony for the upper. Whether you’re looking for a spacious owner-occupied home with rental income to help offset expenses or an investment property with the big-ticket improvements already taken care of, this one gives you plenty of options and plenty of room. Come see 3624 Rolliston Road in person. You may be surprised just how much home you’re getting here.

3624 Rolliston Road, Shaker Heights

3670 Winchell Road, Shaker Heights
$309,900
7 Beds ⋅ 4 Baths ⋅ 5244892 MLS
Welcome to 3670 Winchell Rd in Shaker Heights! This exceptional two-family home offers tremendous flexibility—perfect for an investor or owner-occupant looking to offset their mortgage with rental income. Featuring classic Shaker Heights charm and craftsmanship, the property offers over 3,000 square feet of above-grade living space, three full bathrooms, a partially finished basement with an additional full bath, and a three-car brick garage. The first-floor unit features a spacious living room filled with leaded windows, beautiful hardwood floors, and a paneled fireplace, flowing into a large formal dining room. The kitchen offers generous cabinet and counter space, a charming breakfast room, and access to a covered patio overlooking the backyard. The second and third-floor unit offers a spacious living room with original hardwood floors and a fireplace, built-ins in the dining area, a well-appointed kitchen with breakfast area, and a covered patio. The third floor, accessible by two stairways, includes an updated full bath and three additional rooms ideal for bedrooms, an office, guest space, or family room. Additional highlights include a partially finished basement, ample storage, fresh landscaping, a three-car garage, and a new roof (2024). The property will transfer POS compliant. Conveniently located near the Van Aken District, public transportation, Case Western Reserve University, Cleveland Clinic, and University Hospitals. Whether you're expanding your investment portfolio or looking to live in one unit and rent the other, this duplex offers excellent flexibility and income potential. Schedule your private showing today!

3670 Winchell Road, Shaker Heights

19619 Winslow Road, Shaker Heights
$409,000
6 Beds ⋅ 3 Baths ⋅ 5229525 MLS
POS COMPLIANT! Perfectly positioned just a short walk from the vibrant Van Aken District, this beautifully updated two-family home offers an exceptional opportunity for both investors and owner-occupants. Extensively renovated in 2015, the property features major improvements including updated Romex electrical wiring, modern plumbing, stylish kitchens and bathrooms, central air conditioning throughout both units, and the addition of a dedicated third-floor laundry area to service the upper unit. Best of all, the home is currently vacant, allowing an owner-occupant to choose their preferred unit while generating rental income from the other—or giving investors the flexibility to lease both units at current market rates. The first-floor unit offers two spacious bedrooms, one full bathroom, beautiful hardwood floors, and an updated kitchen complete with quality cabinetry, granite countertops, and abundant storage. The expansive upper unit spans the second and third floors and features four bedrooms, two full bathrooms, hardwood flooring throughout (with brand-new carpet installed in one bedroom this week), and an equally impressive updated kitchen featuring quality cabinetry, granite countertops, and ample storage. The upper unit also enjoys the convenience of its own dedicated laundry area. The large basement provides excellent storage space and includes a separate laundry area for the first-floor unit. Outside, you'll find a two-car garage with additional off-street parking for a third vehicle, a charming grassy yard, and peace of mind knowing the exterior received a fresh coat of paint in 2026 along with extensive masonry work completed the same year. Whether you're looking to build your investment portfolio or offset your mortgage with rental income, this turnkey property in one of Shaker Heights' most desirable locations is an opportunity you won't want to miss.

19619 Winslow Road, Shaker Heights

3646 Lynnfield Road, Shaker Heights
$375,000
6 Beds ⋅ 3 Baths ⋅ 5212651 MLS
Fantastic opportunity to own a beautiful two-family property that exudes character throughout, home-like feel that is attractive to tenants/owner occupants and well maintained. An excellent opportunity for an owner occupant looking to offset their mortgage with rental income, or for an investor seeking to capitalize on a strong rental market within a desirable blend of a single-family home community. It has beautiful hardwood floors, decorative fireplace, large window, formal dining room with built-in cabinets. Second floor living room has a soaring vaulted beam ceiling, large window, decorative fireplace, and a Juliet loft area adding architectural charm, formal dining with built-in cabinets, french doors, and a cove ceiling. The kitchen/bathrooms have tiled floors, and bathrooms have been updated. Most of the windows are vinyl resulting in lower gas bills. There are two bedrooms on the second floor, also 2 bedrooms on the 3rd floor with a full bath and a storage area. Included is a 3-car garage, in addition to parking area alongside the garage. Tenant parks alongside the garage giving full access to all three garage spaces at the present time. There is ample space to turn around to exit the property. Additionally, both units have rear porches and updated electrical panels which can accomodate a/c mini splits, many other unique features such as laundry chutes in each unit, wood-stained doors, original heat registers, spiral steps at back hallway from the basement to the third floor. Basement laundry area has a laundry hook for both units, all appliances stay. Newer water, sewer infrastructure lines were installed, as well as a copper water line installed to the property. Convenient travel to Van Aken District, Cleveland Clinic, University Hospitals, Rapid railway to Downtown Cleveland and Cleveland Hopkins Airport. Owner is a licensed real estate agent, and the occupant of the second-floor, showings can be same day. Seller plans to complete point of sale repairs.

3646 Lynnfield Road, Shaker Heights

18427 Winslow Road, Shaker Heights
$334,000
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

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