Chesterland, OH Homes

• 

  

  

  /44

  $437,500

  Under Contract

  • 3 Beds
  • 2 Baths
  • 3,018 Sq Ft

  8585 Carmichael Dr, Chesterland, OH 44026

  Meticulously Maintained Four-Level Split with Custom Addition on a One-Acre Lot! Updated 3-bedroom, 2-bath home combining privacy and convenience. Multi-level decks, screened porch, babbling brook, and wooded views! Interior highlights include fresh paint, LVT, ceramic, and carpet flooring, beautiful granite countertops, updated baths with full ceramic tile shower, and a new sliding glass door.

  

  Joseph Zingales

  Berkshire Hathaway HomeServices Professional Realty

  8585 Carmichael Dr, Chesterland, OH 44026
• 

  

  

  /31

  $5,500 Per Month

  • 3 Beds
  • 3.5 Baths
  • 4,263 Sq Ft
  • House for Rent

  7050 Wilson Mills Rd, Chesterland, OH 44026

  Adjacent to Gates Mills, this beautifully renovated 4,000 sq. ft. ranch sits on a private, wooded 5-acre lot. The home offers three spacious bedrooms, each with its own bath, along with a large primary suite featuring a walk-in closet. Enjoy the convenience of first-floor laundry, a private office, and a generous family room with a cozy fireplace. Outside, a new patio and a two-car garage

  Anthony Romano Century 21 Homestar

  7050 Wilson Mills Rd, Chesterland, OH 44026
• 

  

  

  /50

  $625,000

  Sold Jun 01, 2026

  8301 Sherman Rd, Chesterland, OH 44026

  • 4 Beds
  • 2.5 Baths
  • 5,618 Sq Ft
  • Built 1930

  Last Sold Summary

  • 14% Below List Price
  • $111/SF
  • 73 Days On Market

  Current Estimated Value $640,961

  Last Listing Agent Jamie Iannetta Keller Williams Greater Metropolitan

  8301 Sherman Rd, Chesterland, OH 44026
• 

  

  

  /23

  Est $365,813

  Not Listed For Sale

  9706 Mayfield Rd, Chesterland, OH 44026

  • 3 Beds
  • 2 Baths
  • 1,892 Sq Ft
  • Built 1955

  9706 Mayfield Rd, Chesterland, OH 44026

  Last Sold Summary

  • 1 Day On Market
• 

  

  

  /50

  $625,000

  • 3 Beds
  • 2.5 Baths
  • 3,228 Sq Ft

  10506 Mayfield Rd, Chesterland, OH 44026

  Welcome to a truly one-of-a-kind custom log home nestled in the natural beauty of Chesterland.Impressive 3-bedroom, 2-bath raised ranch offers approximately 3,228 total square feet and combines exceptional craftsmanship, quality construction, and a setting that feels more like a mountain retreat than Northeast Ohio. Built by Neville Log Homes of Montana using Engelmann Spruce and Lodgepole Pine

  

  Sal Jackson

  Berkshire Hathaway HomeServices Professional Realty

  10506 Mayfield Rd, Chesterland, OH 44026
• 

  

  /50

  $495,000

  Sold Sep 30, 2025

  11855 Heath Rd, Chesterland, OH 44026

  • 4 Beds
  • 2.5 Baths
  • 3,381 Sq Ft
  • Built 1973

  Last Sold Summary

  • $146/SF
  • 4 Days On Market

  Current Estimated Value $514,191

  Last Listing Agent Diane Russo Armington Berkshire Hathaway HomeServices Professional Realty

  11855 Heath Rd, Chesterland, OH 44026
• 

  

  /20

  Est $279,671

  Not Listed For Sale

  13108 Marilyn Dr, Chesterland, OH 44026

  • 3 Beds
  • 1.5 Baths
  • 1,354 Sq Ft
  • Built 1960

  13108 Marilyn Dr, Chesterland, OH 44026

  Last Sold Summary

  • 35 Days On Market
• 

  

  /48

  $250,000

  • 3 Beds
  • 1 Bath
  • 1,254 Sq Ft

  9087 Ranch Dr, Chesterland, OH 44026

  Full general home inspection, septic and well inspections, along with a third-party appraisal have been completed and are available upon request. There is an offer deadline of 8 pm on June 18. Nestled on nearly 2 sprawling acres in desirable Chesterland, this charming ranch home offers privacy, character, and plenty of space to enjoy both indoors and out! The inviting living room features

  Kevin Wasie Exactly

  9087 Ranch Dr, Chesterland, OH 44026
• 

  

  /46

  $323,500

  Sold Oct 15, 2025

  12084 Heath Rd, Chesterland, OH 44026

  • 4 Beds
  • 2.5 Baths
  • 2,640 Sq Ft
  • Built 1964

  Last Sold Summary

  • 4% Below List Price
  • $123/SF
  • 14 Days On Market

  Current Estimated Value $360,895

  Last Listing Agent Meegan Smolsky Real of Ohio

  12084 Heath Rd, Chesterland, OH 44026
• 

  

  /41

  Est $333,251

  Not Listed For Sale

  8218 Maple Dr, Chesterland, OH 44026

  • 3 Beds
  • 2 Baths
  • 1,834 Sq Ft
  • Built 1960

  8218 Maple Dr, Chesterland, OH 44026

  Last Sold Summary

  • 6 Days On Market
• 

  

  /45

  $995,000

  Pending

  • 5 Beds
  • 4.5 Baths
  • 7,462 Sq Ft

  7775 Woodlands Trail, Chesterland, OH 44026

  Nestled on three wooded acres on a quiet street, this extraordinary estate combines refined sophistication with the warmth of a true family home. A circular drive framed by mature trees sets the tone, leading to a residence that offers privacy, elegance, and a lifestyle of effortless comfort. Step inside and you are greeted by a dramatic two-story foyer, where gleaming hardwood floors flow

  Terry Young Keller Williams Greater Metropolitan

  7775 Woodlands Trail, Chesterland, OH 44026
• 

  

  /49

  $365,000

  Sold Jun 17, 2026

  13310 Cedar Acres Dr, Chesterland, OH 44026

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Above List Price
  • $261/SF
  • 16 Days On Market

  Current Estimated Value $327,458

  Last Listing Agent Joseph Cicero Keller Williams Greater Metropolitan

  13310 Cedar Acres Dr, Chesterland, OH 44026
• 

  

  /50

  Est $471,271

  Not Listed For Sale

  8020 Birchwood Dr, Chesterland, OH 44026

  • 4 Beds
  • 3 Baths
  • 3,230 Sq Ft
  • Built 1977

  8020 Birchwood Dr, Chesterland, OH 44026

  Last Sold Summary

  • 28 Days On Market
• 

  

  /23

  $80,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths

  8701 Mayfield Rd Unit 148, Chesterland, OH 44026

  Looking to downsize or lower costs...this spacious 2 bed/2 bath well-maintained manufactured home in the much sought after 55+ Maywood Community is a great alternative to renting. Privacy yet affordable living in this lovely home with bump-out great room, large screened covered porch, and a dog kennel on a corner lot. Newly renovated spacious kitchen with new cupboards, granite countertop, new

  Susan Stone Keller Williams Living

  8701 Mayfield Rd Unit 148, Chesterland, OH 44026
• 

  

  /40

  $376,000

  Sold Mar 19, 2026

  13170 Caves Rd, Chesterland, OH 44026

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft
  • Built 1947

  Last Sold Summary

  • 5% Below List Price
  • $209/SF
  • 156 Days On Market

  Current Estimated Value $388,682

  Last Listing Agent Victor Cizek RealtyNet, Inc.

  13170 Caves Rd, Chesterland, OH 44026
• 

  

  /40

  Est $329,006

  Not Listed For Sale

  11402 Chillicothe Rd, Chesterland, OH 44026

  • 3 Beds
  • 1.5 Baths
  • 1,790 Sq Ft
  • Built 1938

  11402 Chillicothe Rd, Chesterland, OH 44026

  Last Sold Summary

  • 4 Days On Market
• 

  

  /37

  $1,495,000

  • 5 Beds
  • 4.5 Baths
  • 7,266 Sq Ft

  7885 Pear Tree Dr, Chesterland, OH 44026

  Set amidst over 5 acres of breathtaking, manicured grounds, this exceptional estate offers exquisitely designed living space, where timeless elegance meets unmatched tranquility. The five-bedroom, four and a half bath residence with walk-out lower level is surrounded by picturesque scenery, and a gated turnaround driveway, creating a private retreat defined by beauty, serenity, and refined

  Danielle Angie McDowell Homes Real Estate Services

  7885 Pear Tree Dr, Chesterland, OH 44026
• 

  

  /36

  $410,000

  Sold Mar 25, 2026

  8735 Cedar Rd, Chesterland, OH 44026

  • 4 Beds
  • 2.5 Baths
  • 3,656 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Below List Price
  • $112/SF
  • 254 Days On Market

  Current Estimated Value $435,159

  Last Listing Agent Anita Butler Howard Hanna

  8735 Cedar Rd, Chesterland, OH 44026
• 

  

  /49

  Est $346,959

  Not Listed For Sale

  12691 Opalocka Dr, Chesterland, OH 44026

  • 2 Beds
  • 2.5 Baths
  • 4,273 Sq Ft
  • Built 1955

  12691 Opalocka Dr, Chesterland, OH 44026

  Last Sold Summary

  • 33 Days On Market
• 

  

  /39

  $679,900

  $20K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,376 Sq Ft

  10640 Butternut Rd, Chesterland, OH 44026

  Architecturally striking, 4 bedroom, 3.5 bath, multi-level home sits on over 9 acres of private, wooded land with a layout that maximizes natural light & scenic views from every level, with expansive windows and multiple decks that create seamless indoor-outdoor living. The open-concept kitchen is the heart of the home with soaring vaulted ceilings with wood beams, sleek gray cabinetry, stainless

  Lisa Cole Engel & Völkers Distinct

  10640 Butternut Rd, Chesterland, OH 44026
• 

  

  /35

  $580,000

  Sold Aug 29, 2025

  8586 Kirkwood Dr, Chesterland, OH 44026

  • 4 Beds
  • 3.5 Baths
  • 2,784 Sq Ft
  • Built 2005

  Last Sold Summary

  • 5% Above List Price
  • $208/SF
  • 4 Days On Market

  Current Estimated Value $599,629

  Last Listing Agent Sarah Hendershot Redfin Real Estate Corporation

  8586 Kirkwood Dr, Chesterland, OH 44026
• 

  

  /26

  Est $401,341

  Not Listed For Sale

  12633 Ward Dr, Chesterland, OH 44026

  • 4 Beds
  • 2.5 Baths
  • 1,550 Sq Ft
  • Built 2023

  12633 Ward Dr, Chesterland, OH 44026

  Last Sold Summary

  • 309 Days On Market
• 

  

  /39

  $449,900

  $50K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,250 Sq Ft

  10200 Mayfield Rd, Chesterland, OH 44026

  Nestled in the woods in Munson Township, is a spacious log cabin home, with 4 bedrooms and 2 and a half baths. This home sits on 3.72 acres of picturesque land with views of the woods, ravine, rock piles, and more. Nature truly does surround you here. The wormy chestnut walls and ceilings in the living room and kitchen give this home so much warmth and country charm. The two stone fireplaces, one

  Cynthia Chiudioni CC Sells Homes, LLC.

  10200 Mayfield Rd, Chesterland, OH 44026
• 

  

  /49

  $420,000

  Sold Jul 08, 2025

  12539 Woodside Dr, Chesterland, OH 44026

  • 4 Beds
  • 3 Baths
  • 2,544 Sq Ft
  • Built 1964

  Last Sold Summary

  • 8% Above List Price
  • $165/SF
  • 3 Days On Market

  Current Estimated Value $445,163

  Last Listing Agent Sara Shier EXP Realty, LLC.

  12539 Woodside Dr, Chesterland, OH 44026
• 

  

  /50

  Est $519,772

  Not Listed For Sale

  11730 Legend Creek Dr, Chesterland, OH 44026

  • 4 Beds
  • 3.5 Baths
  • 3,584 Sq Ft
  • Built 1988

  11730 Legend Creek Dr, Chesterland, OH 44026

  Last Sold Summary

  • 136 Days On Market
• 

  

  /32

  $425,000

  Under Contract

  • 4 Beds
  • 3 Baths
  • 3,264 Sq Ft

  12445 Sperry Rd, Chesterland, OH 44026

  Escape to Your Own Private Woodland Retreat on Nearly 7 Acres in Schoenwald Trail Private Residences. This spacious 4/5 bedroom home is nestled on 6.92 wooded acres & backs directly to Sunnybrooke Preserve, offering exceptional privacy, natural beauty & endless possibilities for outdoor enjoyment. A full-length covered front porch greets you and your guests into a welcoming spacious foyer with

  Linda Ebersbacher Howard Hanna

  12445 Sperry Rd, Chesterland, OH 44026
• 

  

  /46

  $557,000

  Sold Jun 26, 2026

  11905 Sandgate Dr, Chesterland, OH 44026

  • 4 Beds
  • 2.5 Baths
  • 3,168 Sq Ft
  • Built 1974

  Last Sold Summary

  • 24% Above List Price
  • $176/SF
  • 4 Days On Market

  Current Estimated Value $453,924

  Last Listing Agent Jamie Iannetta Keller Williams Greater Metropolitan

  11905 Sandgate Dr, Chesterland, OH 44026
• 

  

  /50

  Est $668,790

  Not Listed For Sale

  12535 Heath Rd, Chesterland, OH 44026

  • 5 Beds
  • 3.5 Baths
  • 2,852 Sq Ft
  • Built 1847

  12535 Heath Rd, Chesterland, OH 44026

  Last Sold Summary

  • 12 Days On Market
• 

  

  /40

  $415,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,694 Sq Ft

  10571 Mayfield Rd, Chesterland, OH 44026

  Riverfront acreage in Geauga County! Welcome to the historic James Hopson home, built in 1853 and part of the original Hopson Homestead, the Hopson family being the first permanent settlers of Munson Township. Also a part of the Cleveland & Eastern Interurban Railroad, there is yet another layer of historic significance added to this beautiful property. The current owners have lovingly cared for

  Terry Mitchell Howard Hanna

  10571 Mayfield Rd, Chesterland, OH 44026
• 

  

  /21

  $268,000

  Sold Jul 09, 2025

  13014 Cherry Ln, Chesterland, OH 44026

  • 3 Beds
  • 1.5 Baths
  • 1,144 Sq Ft
  • Built 1960

  Last Sold Summary

  • 11% Below List Price
  • $234/SF
  • 14 Days On Market

  Current Estimated Value $267,531

  Last Listing Agent Erin Paglio Platinum Real Estate

  13014 Cherry Ln, Chesterland, OH 44026
• 

  

  /22

  Est $381,851

  Not Listed For Sale

  9721 Mayfield Rd, Chesterland, OH 44026

  • 3 Beds
  • 2.5 Baths
  • 1,543 Sq Ft
  • Built 1974

  9721 Mayfield Rd, Chesterland, OH 44026

  Last Sold Summary

  • 50 Days On Market
• 

  

  /41

  $665,000

  Pending

  • 5 Beds
  • 3 Baths
  • 4,160 Sq Ft

  8555 Red Oak Dr, Chesterland, OH 44026

  What an amazing place to call HOME! Center hall Colonial 4 bedroom with 5th bedroom on main floor! Completely remodeled with new fixtures, flooring, carpeting, kitchen counters and backsplash, fresh paint, and all 3 bathrooms are updated. But so much more! Start off when you arrive noting that there are 4 homes on the Cul de sac for added privacy and no traffic! The home boasts a 275 sf wrap

  Kymberley Hackle Howard Hanna

  8555 Red Oak Dr, Chesterland, OH 44026
• 

  

  /44

  $457,500

  Sold Jul 31, 2025

  7214 Mulberry Rd, Chesterland, OH 44026

  • 3 Beds
  • 3 Baths
  • 2,690 Sq Ft
  • Built 1970

  Last Sold Summary

  • 13% Below List Price
  • $170/SF
  • 91 Days On Market

  Current Estimated Value $479,961

  Last Listing Agent Karine Garfield Howard Hanna

  7214 Mulberry Rd, Chesterland, OH 44026
• 

  

  /44

  Est $344,381

  Not Listed For Sale

  12747 Rockhaven Rd, Chesterland, OH 44026

  • 3 Beds
  • 2.5 Baths
  • 2,034 Sq Ft
  • Built 1980

  12747 Rockhaven Rd, Chesterland, OH 44026

  Last Sold Summary

  • 7 Days On Market
• 

  

  /36

  $435,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,126 Sq Ft

  12259 E Shiloh Dr, Chesterland, OH 44026

  Looking for your forever home? This immaculate, beautifully maintained property truly has it all! Featuring 3 bedrooms, 2 full baths, and 1 half bath, this home offers both comfort and exceptional living space throughout. As you enter, you’ll immediately notice the pristine tile flooring and recently updated carpeting. The spacious family room features rich hardwood flooring and a stunning full

  Karen Russell Howard Hanna

  12259 E Shiloh Dr, Chesterland, OH 44026
• 

  

  /21

  $295,000

  Sold Oct 30, 2025

  8494 Sharp Ln, Chesterland, OH 44026

  • 4 Beds
  • 1.5 Baths
  • 1,554 Sq Ft
  • Built 1958

  Last Sold Summary

  • 13% Above List Price
  • $190/SF
  • 4 Days On Market

  Current Estimated Value $303,535

  Last Listing Agent Jillian Wright Deleted Agent

  8494 Sharp Ln, Chesterland, OH 44026
• 

  

  /50

  Est $483,199

  Not Listed For Sale

  12611 Heath Rd, Chesterland, OH 44026

  • 4 Beds
  • 2.5 Baths
  • 3,216 Sq Ft
  • Built 1999

  12611 Heath Rd, Chesterland, OH 44026

  Last Sold Summary

  • 19 Days On Market
• 

  

  /14

  $215,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft

  12555 Hovey Dr, Chesterland, OH 44026

  Bring your vision and creativity to this rare opportunity in the heart of Chesterland! Located on a quiet dead end street, this 3 bedroom, 2 bath ranch offers convenient single floor living on a spacious 0.69-acre lot. The property backs to a wooded area, creating a peaceful park like setting with plenty of privacy. This home is in need of a complete renovation and is being offered as an

  Glen Whitten Ohio Property Group, LLC

  12555 Hovey Dr, Chesterland, OH 44026
• 

  

  /50

  $375,000

  Sold Dec 05, 2025

  8189 Mulberry Rd, Chesterland, OH 44026

  • 4 Beds
  • 3 Baths
  • 1,784 Sq Ft
  • Built 1948

  Last Sold Summary

  • 7% Above List Price
  • $210/SF
  • 4 Days On Market

  Current Estimated Value $379,117

  Last Listing Agent April Pillar Russell Real Estate Services

  8189 Mulberry Rd, Chesterland, OH 44026
• 

  

  /50

  Est $343,325

  Not Listed For Sale

  12165 Heath Rd, Chesterland, OH 44026

  • 3 Beds
  • 1.5 Baths
  • 1,651 Sq Ft
  • Built 1940

  12165 Heath Rd, Chesterland, OH 44026

  Last Sold Summary

  • 6 Days On Market

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