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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
$775,000
6 Beds ⋅ 5 Baths ⋅ 5223186 MLS
Set on 1.24 lush acres with 209 feet of frontage, this six-bedroom Colonial delivers what Shaker rarely offers at any price: real land, real scale and real architectural pedigree. Designed in 1910, the home carries genuine provenance across 5,098 square feet. Inside, a dramatic curved staircase wrapped in hand-forged wrought iron scrollwork rises through two stories of original leaded glass, including a heraldic stained glass crest -- irreplaceable craftsmanship you simply cannot recreate. Grand formal entry and rooms with soaring leaded-glass windows, original fireplaces and hardwood floors carry the scale of an era that valued room to gather. A substantial first-floor library, richly paneled in wood with its own fireplace, offers the kind of retreat today's homes cannot. The kitchen features granite countertops, a butler's pantry and a light-filled breakfast room. The primary suite is a retreat unto itself, with a generous sleeping area framed by gorgeous windows, an updated bath with double sinks and new countertops, and a dedicated dressing area. Slate roof, plaster walls throughout, three fireplaces, central air and a three-car garage and a circular driveway with entrances on both Shaker and Attleboro. Violation-free POS. A coveted Shaker Boulevard address (originally 17219 Shaker), two blocks from the Attleboro Rapid station -- minutes to University Circle, world-class cultural institutions, hospitals, universities and downtown Cleveland. Homes with this lot, this address and this pedigree do not come available often in Shaker. A rare opportunity to own a genuine piece of the community's founding story.

2800 Attleboro 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
$699,000
6 Beds ⋅ 4 Baths ⋅ 5219756 MLS
Architecturally striking and effortlessly livable, this fully renovated Shaker Heights residence offers a rare combination of artistic design and everyday comfort. With six bedrooms and four full bathrooms, the home unfolds across multiple levels with a sense of fluidity and grace. Whether entertaining, working from home, or simply enjoying quiet moments, every space has been elevated to support modern life in style. A dramatic floating three-level staircase anchors the entry, setting the tone for the home’s clean lines and open flow. Sleek tile flooring extends throughout the first level, guiding you into an expansive, light-filled living space where design and purpose meet. The chef-inspired kitchen is both striking and functional, featuring quartz countertops, crisp white cabinetry, stainless steel appliances, a stunning tile backsplash, and a full breakfast bar—an ideal hub for gathering. From the open-concept family room, oversized sliders lead to a stamped concrete patio and a fully fenced yard for seamless indoor-outdoor entertaining. A vaulted home office/den on the main level offers a sunlit space to work or create, while dual laundry areas provide convenience. The primary suite is a true retreat, offering a spa-like glamour bath with dual vanities, an expansive custom-tiled walk-in shower, and a separate nursery or sitting wing—designed for versatility. The lower level extends the home’s potential, with an additional bedroom, a spacious recreation room, and a full in-law suite (including full kitchen) with private entrance—ideal for multi-generational living, guests or rental income opportunities. With a newer roof and HVAC, refined updates throughout, and a prime location across from a prestigious private school, near shopping, dining, and parks, this home offers architectural distinction and contemporary luxury.

20601 Shelburne Road, Shaker Heights
$990,000
6 Beds ⋅ 5 Baths ⋅ 5215255 MLS
A striking center-hall brick Georgian on one of Shaker Heights' tree-lined streets. The grand foyer makes an immediate impression, drawing the eye to an elegant split staircase that sets the tone. French doors to one side open to the formal dining room; to the other, the living room flows to a screened porch, a refined office/library at the opposite end. Floor-to-ceiling windows in both the dining and living rooms flood the spaces with light and offer wonderful views of the outdoors. Generously proportioned rooms are suited for grand entertaining and everyday life. The living room focal point is a stately, oversized fireplace, while the light-filled dining room is made for long dinners and good company. The kitchen is spacious— butcher block counters, an exposed brick wall, a Dutch door, and an adjoining scullery that connects seamlessly to the dining room. Just off the kitchen, a sunny breakfast room is the kind of space you'll find yourself in every morning. The family room is where this home shines. Sprawling and beautifully appointed, it features a built-in beverage bar and multiple sets of French doors that open directly to the backyard — a manicured retreat with a patio, firepit, and privacy. A remodeled powder room and first-floor laundry round out the main level. Upstairs, a light-filled reading nook anchors the second floor. Six to seven bedrooms and three full bathrooms offer plenty of flexibility. The oversized primary suite includes a dedicated dressing area. A private rear wing — reached via the back staircase — has two bedrooms, a sitting room, and a remodeled full bathroom, perfect as a guest, teen, or au pair suite. The finished third floor offers a spectacular, ballroom-scale room ready to be whatever you need it to be — gym, playroom, or something else entirely. Attached two-car garage. Meticulously maintained and thoughtfully improved by its owners. The finished third floor offers an additional 750 square feet of living space.

2928 Attleboro 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
$1,075,000
6 Beds ⋅ 6 Baths ⋅ 5213456 MLS
Located in the highly sought-after Shaker Heights Club District, this stunning 6-bedroom, 6-bathroom Tudor blends timeless architectural charm with extensive modern updates. Featuring gorgeous woodwork, crisp white walls, original hardwood floors throughout, and incredible character at every turn, this home offers classic elegance w/ today’s modern functionality. Over the past 2 years, the majority of the home has undergone significant renovations & thoughtful improvements. The third floor was transformed into a flexible suite that can serve as a primary suite or guest suite, complete w/ a luxurious en-suite bathroom featuring heated floors, double vanity, soaking tub, separate shower, walk-in closet, wet bar, sitting area, & fireplace. The kitchen was fully opened & renovated with soapstone countertops, new appliances, & refinished original hardwood floors after removing tile, creating a bright, functional, modern space. The basement was finished with a full bathroom & gas fireplace, adding valuable additional living & entertaining space. The laundry room was relocated from the basement to the second-floor for convenience. A sump pump & central air conditioning were also added.The first floor is filled w/ natural light from original leaded-glass windows & features an oversized living room w/ a gas burning fireplace, an elegant dining room, and an updated kitchen w/ a dedicated eating area for a breakfast table. Also on the first floor are an office/den, powder room, & attached 2-car garage. The second floor features 3 large bedrooms, including a Jack-and-Jill setup, plus 2 additional bedrooms over the garage & 3 full bathrooms. The upper-level suite provides a rare & highly flexible layout for homes of this era. The backyard is oversized for the Club District, offering ample green space for entertaining, play, and relaxation, & is partially fenced-in. The home will be POS compliant at closing. Ideally located just moments from the Van Aken District!

3002 Manchester 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
$800,000
6 Beds ⋅ 5 Baths ⋅ 5209851 MLS
Featured in "Distinguished Homes of Shaker Heights", this Meade and Hamilton gem is close to everything--including perfection. Lush walking trails and fine dining are a delightful walk away. The property has been impeccably preserved and thoughtfully updated. The owner created a gracious front landscape with circular drive, authentic stonework and curated plantings which add an aire of elegance and immediate curb appeal. The living room is appointed with window seats flanking the original fireplace while providing access to the charming sunroom with updated double French doors to the stone patio and rear yard. A banquet-size dining room with detailed molding, a bay window and fireplace is perfectly sited for gracious entertaining. The butler's pantry and eat-in kitchen are well designed. A few steps up the broad staircase the original, wood-paneled library now serves as a dramatic family room with shelves lining the walls, a veranda overlooking the expansive backyard, the original fireplace and leaded glass windows adding to the ambiance. The second floor has six bedrooms--four main bedrooms--all nicely sized with good closets. The primary suite was reinvented by this homeowner with a totally redone bath and walk-in closet. All of the other three bedrooms enjoy an en-suite full bath. At the rear of the second floor two smaller bedrooms (one now used as an office and the other as a meditation space) share a full bath. Closets galore throughout the second floor. The third floor has one expansive finished space which is an ideal playroom, workshop or hobby area plus a sizable storage area. Enjoy the lower level media room and do laundry in the bright and cheerful laundry area. The large flat back yard is waiting for games and guests. Central air. Unbeatable location. Close to walking trails and parks, hospitals, cultural institutions, fine restaurants and an easy commute to downtown by car or rapid transit.

14211 Larchmere Boulevard, 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
$1,400,000
8 Beds ⋅ 5 Baths ⋅ 5212371 MLS
A Historic Waterfront Masterpiece on South Woodland Perched on a sprawling 1.09-acre lot in the heart of historic Shaker Heights, 16310 S Woodland Road is a rare architectural jewel that seamlessly pairs timeless 1919 craftsmanship with an irreplaceable natural setting. Sitting proudly alongside the iconic Marshall Mansion, this magnificent 8-bedroom, 7,628-square-foot brick Colonial offers an elite lifestyle reserved for the few, featuring your own private sanctuary with Marshall Lake right in your backyard. Step inside the grand entryway and you are immediately greeted by the home's crowning glory: breathtaking, luxurious woodwork. From the richly detailed custom paneling and pristine hardwood floors to the masterful crown moldings and handsome built-ins, the artisanal millwork throughout the home radiates an era of uncompromised quality. The expansive interior layout flows effortlessly, highlighted by a sunken living room featuring a dramatic bay window designed specifically to frame the serene, shimmering views of the lake. Outside, the estate transforms into a private park-like oasis. Relax on the grounds or host unforgettable gatherings against the backdrop of the water and the historic elegance of your neighboring estate. Complete with a spacious layout, premium historical pedigree, and close proximity to the Van Aken District, top-tier schools, and the rapid transit for easy access to downtown, this is more than a home—it is a legacy property. Schedule your private tour to experience Shaker Heights luxury at its absolute finest.

16310 S Woodland Road, Shaker Heights
$259,900
8 Beds ⋅ 3 Baths ⋅ 5207247 MLS
Brick Shaker Heights double. Excellent income opportunity. Large units. Convenient location near shopping, downtown, and library. Award winning schools. Upstairs unit vacant to allow for easy showings. 3 car garage. Hardwood floors. Basement rec room.

3638 Lindholm Road, Shaker Heights
$289,999
7 Beds ⋅ 3 Baths ⋅ 5204509 MLS
Welcome to this spacious multi-family home in the highly desirable city of Shaker Heights! This well maintained property offers incredible versatility for both owner-occupants and investors. Each unit features a living room with fireplace, formal dining room, kitchen with stainless steel appliances, 2 bedrooms, 1 full bath and rear porch. The third floor offers 3 additional bedrooms and 1 full bath great for additional living and income potential. The backyard has ample parking and detached 2 car garage. Schedule your private showing today, this one won’t last long!

17415 Winslow Road, Shaker Heights
$649,000
6 Beds ⋅ 4 Baths ⋅ 5205280 MLS
Perched gracefully on a hill in the highly sought-after Malvern neighborhood of Shaker Heights, this storybook center hall colonial delivers timeless charm, exceptional curb appeal, and an unbeatable location. A stunning Japanese maple beautifully frames the home, setting the tone before you even step inside. The welcoming center hall foyer opens to a spacious living room, a cozy office or TV room, and a delightful screened-in porch—perfect for relaxing evenings. To the right, a generous dining room flows into the updated kitchen, which features butcher block countertops, stainless steel appliances, a farmhouse sink, and a versatile eat-in counter ideal for casual dining or working from home. A convenient powder room completes the first floor. Upstairs, the elegant staircase leads to a landing adorned with leaded glass windows, adding a touch of classic character. The second floor offers four well-appointed bedrooms with hardwood floors and ample storage. The front-facing primary suite includes an en-suite bathroom and walk-in closet, while two bedrooms share a charming Jack and Jill bath. The third floor provides a flexible full suite with two additional bedrooms, a shared full bath featuring a clawfoot tub and shower surround, and abundant storage space. The lower level features a finished recreation room along with a clean mechanical and laundry area finished with Nature Stone flooring. Outside, the private backyard is perfect for entertaining or everyday enjoyment, complete with a stone patio, raised garden beds, and plenty of green space. A solid two-car garage with a new door adds to the home’s functionality. Additional highlights include central A/C, a working fireplace, Alexa-controlled exterior lighting and security, and abundant natural light throughout. Ideally located moments from Van Aken District, Shaker Heights CC, Thornton Park, and the RTA Rapid Transit, with quick access to highways and downtown, this home truly offers the best of Shaker living.

19901 Malvern 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
$449,000
6 Beds ⋅ 5 Baths ⋅ 5199168 MLS
Great opportunity to add to your portfolio with this tenant-occupied property. Offering a functional layout and convenient location near shopping, schools, local amenities, and major routes, this home has strong potential for an investor or future owner-occupant. Please do not disturb tenant. Showings by appointment only.

3448 Lynnfield Road, Shaker Heights
$850,000
6 Beds ⋅ 4 Baths ⋅ 5193279 MLS
Stunning, lovingly restored Tudor in Shaker Heights where timeless character meets thoughtful modern updates. You will feel the warmth, history and love as soon as you step through the front door. The fully reimagined kitchen was taken down to the studs and redesigned to honor the home’s original period, featuring custom Amish hard maple cabinetry, honed granite countertops, porcelain tile flooring, and unlacquered brass hardware. The second floor offers four bedrooms and two full baths, plus a versatile bonus room off the primary suite, ideal for a home office, dressing room, or sitting area. The third floor provides two additional bedrooms and a full bath, creating a seamless extension of living space. The backyard features a patio, greenhouse, and a spacious yard ready for your personal touch. Since 2023, extensive updates include whole-house exterior waterproofing, complete kitchen renovation, radiant heat in the four-season room, electrical panel, asphalt driveway, refinished hardwood floors on all three levels, new lighting throughout, front gutters, and refreshed bathrooms. Perfectly situated in Shaker Heights, this home offers walkable access to the Lower Shaker Lake and Nature Center, Shaker Square Farmers Market, the Rapid, Larchmere, and everyday conveniences—while providing easy access to University Circle, Downtown Cleveland, world-class cultural institutions, major medical centers, and professional sports. A timeless home offering space, character, and an unbeatable connection to the best of Shaker Heights and Cleveland.

2575 Coventry Road, Shaker Heights
$329,000
7 Beds ⋅ 3 Baths ⋅ 5194645 MLS
Investors! Fully Occupied Duplex grossing $2,788.00/month with long-term, stable tenants now available. Fantastic location within 1.5 Miles of VanAken District, 3.04 Miles of the JACK Thistledown Racino, and 4.1 miles of Coventry District. Currently bringing in positive cash flow in a high-demand rental area. Most major items have been replaced within the last 15 years and will deliver a clear POS by closing. This hot deal is ready today for a smooth transition into your portfolio. Schedule your private tour now.

17615 Winslow Road, Shaker Heights
$331,600
6 Beds ⋅ 2 Baths ⋅ 5193272 MLS
Fantastic turnkey opportunity in Shaker Heights, perfect for a savvy investor or an owner-occupant looking for a location that's so popular in the historic Winslow district.

18520 Winslow 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
$170,000
6 Beds ⋅ 3 Baths ⋅ 5185428 MLS
Investor opportunity in Shaker Heights. Duplex property featuring beautiful architectural character, classic details, and strong curb appeal, offered as-is and in need of renovation. POS report available; buyer to assume required escrow and compliance. The property offers a solid layout with potential to reconfigure the upper level into a third unit (buyer to verify), providing an opportunity to maximize future earning potential. Significant updates are needed throughout, making this an ideal project for experienced investors or buyers using renovation financing. Buyers to verify condition, zoning, use, and unit count to their own satisfaction.

3575 Gridley Road, Shaker Heights
$840,000
6 Beds ⋅ 4 Baths ⋅ 5184123 MLS
Some homes speak softly and this Howell & Thomas residence is one of them. Held within the same family for 27 years, 2593 Coventry Road presents a rare opportunity to experience historic Shaker Heights living with warmth, intention, and timeless appeal. Thoughtfully updated over the past five years, the home reflects understated luxury while honoring its architectural roots. Sun-filled spaces flow easily for both everyday living and memorable gatherings, anchored by a remodeled chef’s kitchen designed for connection and ease. A private elevator provides seamless livability between the main and second floors, eliminating the need for a first-floor primary and offering flexibility for years to come. With six bedrooms and three-and-a-half baths, the home offers nearly 4,800 square feet of finished living space, including a fully finished third floor that expands the home’s flexibility for additional bedrooms, guest accommodations, or work-from-home needs. Outdoors, a landscaped and fenced backyard becomes a private escape, complete with a heated pool and patio that invites relaxed entertaining. Perfectly situated in Shaker Heights, this home offers walkable access to the Lower Shaker Lake and Nature Center, Shaker Square Farmers Market, the Rapid, Larchmere, and everyday conveniences; while providing easy access to University Circle, Downtown Cleveland, world-class cultural institutions, major medical centers, and professional sports. Tree-lined streets, classic architecture, and thoughtful modern updates come together to create a home that feels both timeless and entirely livable. This is not simply a house - it’s a lifestyle - quietly waiting to be discovered.

2593 Coventry Road, Shaker Heights
$169,999
6 Beds ⋅ 2 Baths ⋅ 5175608 MLS
Collect almost $3,000/mo with this Shaker duplex. Email agent for market rent roll & video tour along with complete investment analysis, drone footage, information on the mechanical systems of the building. Professional property management availalbe. Local & out of state investors welcome!

3705 Sudbury Road, Shaker Heights
$365,000
6 Beds ⋅ 3 Baths ⋅ 5176990 MLS
GORGEOUS duplex with CENTRAL AC on one of Shaker Heights' most sought-after streets has been remodeled to compete with the modern luxury apartment rentals, but with more space and at a better price! Truly everything that needed to be improved has been, so that you can enjoy worry-free ownership for years to come. The 2-bedroom, 1-bath first floor unit is currently rented through 5.31.26 for $1700. Tenant has been in place since 2022. The Up Unit, which features 4 bedrooms plus a sizeable Bonus Room, as well as 2 bathrooms, spans both the 2nd and 3rd floors and would be great space for an owner-occupant (finished 3rd floor is not included in the square footage). Property improvements include: interior renovations with LVP throughout 1st and 2nd floors, paint, new kitchens with all stainless steel appliances (2022), remodeled bathrooms (2022), 2 new electrical panels (2022), 2 AC condensers (2023), new HWT (2022 + 2025), Ohio Basement Systems with 5-years annual service contract (2022 - see invoice). Other features include: newer garage with automatic opener + vinyl windows with blinds. Property will transfer POS-compliant. A truly fantastic property in a great location to add to your investment portfolio or to house-hack. Schedule a tour today.

17424 Winslow Road, Shaker Heights

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