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$319,900
6 Beds 3 Baths 5230466 MLS
Don't miss this exceptional duplex investment opportunity in the heart of Shaker Heights! Whether you're looking to expand your investment portfolio or occupy one unit while generating rental income from the other, this spacious property offers outstanding flexibility and value. The upstairs unit features 4 bedrooms, an additional office, and 2 full bathrooms, providing plenty of space for a large household or work-from-home setup. The downstairs unit offers 2 bedrooms, a bonus office, and 1 full bathroom, making it an attractive option for tenants or owner-occupants alike. Major updates include a roof that's only 2 years old, newer hot water tanks, and one newer furnace, helping reduce future maintenance expenses. Conveniently located near shopping, dining, parks, public transportation, University Circle, Cleveland Clinic, and Downtown Cleveland, this property is well-positioned for strong rental demand. Whether you're an experienced investor or purchasing your first multifamily property, This home is an opportunity you don't want to miss. Schedule your private showing today!

17411 Chagrin Boulevard, Shaker Heights

$419,000
6 Beds 3 Baths 5229525 MLS
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

$450,000
6 Beds 6 Baths 5225341 MLS
At first glance, you'll think you've found two stunning custom homes, but this exceptional side-by-side duplex offers so much more. Beautifully renovated and move-in ready, this rare Shaker Heights property presents an incredible opportunity for investors seeking strong rental income or owner-occupants looking to live in one residence while offsetting their mortgage by renting the other. Each spacious home offers approximately 2,000 square feet of thoughtfully designed living space featuring 3 bedrooms, 2 full baths, 1 half bath, and an attached two-car garage. Step inside to discover hardwood floors throughout the living room, dining room, staircase, and all three bedrooms, complemented by fresh neutral paint and stylish modern finishes. The updated kitchens are designed to impress with granite countertops, contemporary backsplashes, stainless steel appliances, and durable luxury flooring. Oversized family rooms provide the perfect gathering space for entertaining or everyday living, while convenient first-floor half baths add functionality. Upstairs, each primary suite serves as a private retreat with double closets and an updated ensuite bath. Two additional generously sized bedrooms and an updated full bath complete the second level. Private basements offer separate laundry areas along with bonus rooms ideal for a home office, fitness room, hobby space, or additional storage. Separate gas and electric utilities, quality renovations throughout, and turnkey condition make this property ready for immediate occupancy or rental. With projected market rents of approximately $2,200 to $2,400 per unit, the income potential is outstanding. Ideally located near University Circle, Cleveland Clinic, University Hospitals, Case Western Reserve University, Downtown Cleveland, shopping, restaurants, parks, and all that Shaker Heights has to offer, this rare beautifully updated property delivers exceptional lifestyle appeal and long-term investment potential.

17914 Chagrin Boulevard, Shaker Heights

$295,000
5 Beds 3 Baths 5222456 MLS
Welcome to 3559 Gridley Road in Shaker Heights. Brick, stucco and vinyl sided duplex with a 2-car detached garage. Lovingly cared for, updated and owned by the same family for 50+ years. The 1st and 2nd floor units have identical layouts. 1st/main floor unit is in fabulous shape. Refinished hardwood floors, newer replacement windows, neutral colors, charming built-ins, formal living and dining room, spacious kitchen, wood burning fireplace, 2 spacious bedrooms &, vintage hall full bath & a 3 season sun porch. Impeccably maintained 2nd floor unit features 3 bedrooms and 2 full baths across the 2nd and 3rd levels. Beautiful hardwood floors, newer replacement windows, neutral colors, charming built-ins, formal living and dining rooms, spacious kitchen, wood burning fireplace, 2 spacious bedrooms & a 3 season sun porch. The 2nd level also has access via a side entrance hallway up to the 3rd floor, which has an additional bedroom, common area, bedroom, living area, full bath & small finished storage area. The unfinished basement features a washer, dryer, and additional storage space. 2-car detached garage. Close to Gridley Triangle Park and quick access to Case Western Reserve University, Cleveland Clinic, University Hospitals, University Circle and downtown Cleveland. Main level unit will be listed for rent on 07/15/2026, so owner-occupant buyers need to hurry. Seller to make property city Point of Sale (POS) compliant by title transfer.

3559 Gridley Road, Shaker Heights

$320,000
7 Beds 3 Baths 5221904 MLS
Welcome to the Winslow Road Historic District! This classic Tudor-style duplex home is one of the most architecturally distinguished properties on this beautiful and historic Shaker Heights street. Rich in character, this timeless property showcases stunning original architectural details, including beautiful woodwork, classic craftsmanship, and the charm that makes this Shaker Heights neighborhood so desirable. The upper unit offers 5 bedrooms and 2 full bathrooms and is currently tenant-occupied at $1,830 per month. The lower unit features 2 bedrooms and 1 full bathroom and is rented for $1,200 per month, providing immediate cash flow for investors. Whether you're looking to expand your investment portfolio, or aspire to purchase a property with the opportunity to owner-occupy in the future, this duplex home offers exceptional value. Enjoy a prime location just minutes from the Van Aken District, rapid transit, parks, shopping, restaurants, and everything that makes Shaker Heights one of Northeast Ohio's most sought-after communities.

18428 Winslow Road, Shaker Heights

$219,900
4 Beds 2 Baths 5218646 MLS
Shaker Heights Duplex | Investment or Owner-Occupant Opportunity Don't miss this well-maintained duplex in sought-after Shaker Heights. The first-floor unit comes with a subsidized tenant in place, providing guaranteed rental income of $1,175/month from day one — giving any buyer immediate cash flow at closing. The second-floor unit is vacant offering flexibility for an owner-occupant looking to house-hack or an investor ready to place their own tenant. Some turn work will be needed on the second floor. Seller will place a tenant prior to closing upon buyer request. Both units feature updated luxury vinyl plank flooring, refreshed kitchens with white shaker cabinets and stainless appliances, and updated bathrooms. The first floor showcases a spacious living room with fireplace, crown molding, arched doorways, and a dining room with chandelier — classic Shaker character throughout. The large unfinished basement offers substantial storage and utility space. Outside, enjoy a covered front porch with brick columns, fresh driveway, detached garage, and a well-kept lawn. Sold as-is. Point of Sale (POS) inspection to be assumed by buyer. A rare chance to own in Shaker Heights with built-in income and the flexibility to grow.

3698 Menlo Road, Shaker Heights

$159,900
6 Beds 2 Baths 5218303 MLS
Freshly updated and full of opportunity, this Shaker Heights duplex offers a rare combination of immediate usability and future upside. The freshly painted exterior provides great curb appeal, while the vacant upper unit has been freshly painted and is ready for occupancy, allowing an owner-occupant or investor to begin generating income right away. Both units are served by central air conditioning, and the property features a hard-to-find three-car garage for additional parking, storage, or rental potential. The unfinished third floor offers flexible bonus space for storage, hobbies, or other permitted uses, while the basement provides additional usable space and utility. Conveniently located near shopping, dining, parks, and major commuter routes, this property is an excellent opportunity for both investors and owner-occupants looking to build equity in the desirable Shaker Heights School District.

3646 Chelton Road, Shaker Heights

$449,900
9 Beds 3 Baths 5217713 MLS
Exceptional investment and lifestyle opportunity in the heart of Shaker Heights, just moments from the vibrant Van Aken District and convenient rapid transit service to downtown. Freshly painted and rich in architectural character, this stately brick-and-stone Tudor stands out as one of the most impressive homes on a street renowned for its beauty and charm. Both units showcase the timeless craftsmanship Shaker Heights is celebrated for, featuring high ceilings with exposed beams, abundant natural light, built-in cabinetry, and inviting gas fireplaces. The expansive upper unit lives like a single-family home, offering six spacious bedrooms and two full baths, while the 1st floor unit boasts beautifully refinished hardwood floors, three bedrooms, one full bath, and a private lower-level family/recreation room with an additional gas fireplace. Ideally located near premier shopping, dining, and entertainment, this remarkable property combines historic elegance with modern convenience. Additional updates include both hot water tanks replaced in 2020, and the seller plans to complete all point-of-sale repairs prior to title transfer, making this an outstanding turnkey opportunity. Conveniently located close to restaurants, shopping, hospitals, Little Italy, University Circle, museums and more!

19000 Winslow Road, Shaker Heights

$188,000
6 Beds 2 Baths 5214477 MLS
Opportunity knocks in Shaker Heights! This spacious side-by-side duplex offers over 2,600 square feet with a total of 6 bedrooms and 2 full baths. One unit is currently occupied at $1305 per month providing immediate income, while the vacant unit presents an excellent opportunity for renovation, lease-up, or owner-occupancy. The occupied unit offers additional upside through future updates and rent growth. Being sold strictly as-is, with buyer to assume all Shaker Heights Point of Sale violations. POS report available upon request via email. With strong rental demand, large unit sizes, and numerous renovated duplexes in the area commanding over $300k, this property presents a compelling value-add opportunity for investors looking to build equity through strategic improvements. Conveniently located near shopping, parks, schools, public transportation, and major commuter routes. Bring your vision and unlock the potential of this Shaker Heights investment opportunity. Absolutely no seller financing, no wholesale contracts, END BUYERS ONLY! ***Multiple offers received, highest & best offers due Monday 6/8/26, 9am***

3561 Daleford Road, Shaker Heights

$389,500
6 Beds 3 Baths 5212651 MLS
What a fantastic opportunity to own a beautiful two-family property that exudes character throughout and has been lovingly maintained by the owner-occupied for many years. An excellent opportunity for an occupant owner looking to offset their mortgage with rental income or for an investor with interest in a strong rental market. First-floor unit is rented to a wonderful tenant who has lived there 3+ years with 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 with two more bedrooms on the 3rd floor and a full bath as well as a storage area. Included is a 3-car garage, in addition to parking area alongside the garage. The 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. There are so many other unique features such as hardwood floors, laundry chutes in each unit, wood-stained doors, original heat registers, glass door knobs, spiral steps at back hallway from the basement to the third floor. Newer water, sewer infrastructure lines were installed, and a copper water line installed to the property. Selling willing to escrow for the install of an acceptable quote of a/c for the second/third floor. Conveniently located near schools, libraries, Van Aken District, Rapid railway to Downtown Cleveland and Cleveland Hopkins Airport. Listing agent is a licensed real estate agent/owner, and the occupant of the second-floor, showings can be same day.

3646 Lynnfield Road, Shaker Heights

$429,900
7 Beds 4 Baths 5212976 MLS
Location! Location! Location! Historic Winslow district. Majestic Shaker Heights one of a kind two family brick Tudor features leaded glass windows, vaulted ceilings, beautiful moldings, hardwood floors throughout. Gorgeous 5 bedroom upstairs unit with two story living room perfect for owner occupant or luxury rental featuring brand new upscale kitchen. Up unit is currently tenant occupied. Built-in corner cabinets with leaded glass doors in formal dining room. Beautiful 2 bedroom first floor unit currently vacant and available to show. Walking distance to Van Aken shopping district, RTA line to downtown. Both units feature updated forced air heating and central air. 3 car garage. Total of 7 bedrooms and 4 baths! Shaker Heights point of sale compliant.

19627 Winslow Road, Shaker Heights

$199,000
4 Beds 2 Baths 5201452 MLS
Remodeled Shaker Heights Duplex – Owner Occupied Possible The Opportunity: A meticulously updated up/down duplex in the heart of Shaker Heights. Fully remodeled and generating $2,050 total monthly rent, this property offers a stable, turn-key addition to your portfolio with high-demand appeal and zero deferred maintenance on the interior. Key Interior Features: Fully Updated Units: Both 2-bed, 1-bath units feature brand-new kitchens with stainless appliances, sleek cabinetry, renovated bathrooms, and gleaming refinished hardwood floors. Move-In Ready: Extensive interior renovations mean no immediate work is required. Classic Shaker charm meets modern luxury. Investor Efficiency: Utilities: Separate gas and electric meters (tenants pay their own usage). Storage & Parking: Clean basement with laundry hookups and a 2-car detached garage. Infrastructure: Updated mechanicals and fresh paint throughout. Prime Location: Steps from the RTA Blue Line and minutes from the Van Aken District, University Circle, and Cleveland Clinic. This is a high-demand rental pocket known for strong property values. Stable, remodeled, and performing from Day 1.

3397 Westbury 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

$260,000
4 Beds 4 Baths 5192730 MLS
Great opportunity to own one of the very few four family properties in Shaker Heights! The property consists of 4 one bedroom units. The front units have living, dining, kitchen and bedroom while the back are a bit smaller with living, kitchen and bedroom. The property has a full basement, large attic and two 2-car garages. All units are currently occupied and bringing in a total of $3,125 per month. Cheshire is a well located beautiful street just down from the shops, galleries and restaurants on Larchmere. Shaker Square and its shops, restaurants, drug store, grocery store and theater are just another block further. The RTA Green and Blue line trains are nearby to whisk your tenants off to downtown, the airport or the Van Aken District. Minutes to University Circle, Cleveland Clinic and University Hospitals. Don't miss out on this great investment opportunity.

2536-2538 Cheshire Road, Shaker Heights

$216,000
6 Beds 3 Baths 5189611 MLS
Great opportunity for investor or owner occupant with this two family home situated in the Lomond neighborhood of Shaker Heights. Each unit offers central air with full living room, full dining room, 2 bedrooms, and 1 bath. Dining rooms feature window seat and built in cabinetry. Natural wood floors throughout both units. Units boast spacious kitchens with first floor including a dishwasher and extra counter space that can be utilized for eat-in, work from home, or study area. All appliances remain with the home. Second floor has access to the third floor, and includes additional 2 bedrooms, bathroom, and kitchenette area. Come and view this home in the heart of Shaker Heights. Property is agent owned.

3631 Rolliston Road, Shaker Heights

$355,000
8 Beds 6 Baths 5168757 MLS
Elegant Side-by-Side Duplex in Sought-After Shaker Heights Discover timeless charm and modern convenience in this classic side-by-side duplex perfectly positioned in the heart of Shaker Heights (44122). Just a short stroll from the lively Van Aken District, enjoy easy access to restaurants, shops, and Heinen’s Grocery, Mitchell's for ice cream lovers, plus the RTA transit line only one block away—taking you to Shaker Square and downtown Cleveland in minutes. Each spacious unit offers four bedrooms and two and a half baths, blending comfort and character with beautiful hardwood floors, inviting wood-burning fireplaces, and thoughtfully designed layouts. The north side is vacant and ready for your personal touch—an ideal opportunity for an owner-occupant or fresh renovation. The south side is currently tenant-occupied on a month-to-month basis, providing immediate income flexibility. Both homes include all appliances and showcase the architectural warmth that makes Shaker Heights so special. Whether you’re looking to live on one side and lease the other, or invest in a high-demand rental property, this duplex offers the perfect combination of location, lifestyle, and long-term value.

3475 Norwood Road, Shaker Heights

$319,000
6 Beds 3 Baths 5185404 MLS
Attention Investors! Fully occupied, lovingly maintained, cash-flowing property in Shaker Heights now available. Currently grossing $3,250.00/month with reliable tenants locked in on 1 year leases. Conveniently located within 1.2 miles of shopping, parks, and healthcare. Approximately $100K in improvements have been made within the last 4 years, including a New Roof (2025), New Front Steps(2025), Storm Doors(2025), Basement windows (2025), Replaced Interior Electric Outlets with GFC compatible (2025), Replaced Furnaces (2024), Replaced Water Heater Upstairs (2024), Replaced lower unit Front Windows (2024), Replaced Sewer line from street to house (2024), Replaced Water Heater Downstairs (2024), Replaced Sump Pump (2024), Finished downstairs basement with flooring (2023), Updated both kitchens and repaired both bathrooms (2023), Two New Electrical Panels(2023), Miscellaneous plumbing updates(2023). All you have to do is purchase to start making immediate income. Call to schedule your showing today.

3613 Lynnfield Road, Shaker Heights

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