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Chesterland, OH Homes for Sale

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  • /44

    $450,000

    • 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.

    Agent Photo

    Joseph Zingales

    Berkshire Hathaway HomeServices Professional Realty

    (440) 291-2915

    8585 Carmichael Dr, Chesterland, OH 44026
  • /3

    $216,666

    • 3 Beds
    • 2 Baths

    12963 Lynn Dr, Chesterland, OH 44026

    This is an ONLINE ONLY foreclosure sale. There are NO SHOWINGS. Deposit due by wire transfer within 48 upon conclusion . Cash deal; funding must take place within 30 days of confirmation of sale. 5% Buyer’s Premium shall apply. Subject to postponement and cancellation. Full terms and conditions at online registration.

    Ross C Barton, III Beth Rose Real Estate and Auctions, LLC

    12963 Lynn Dr, Chesterland, OH 44026
  • /2

    $80,000

    • Land
    • 1.5 Acres
    • $53,333 per Acre

    0 Cedar Rd, Chesterland, OH 44026

    Amazing opportunity to build in Geauga county on 1.5 acres in Newbury! Great location on a great street! Wooded lot with a slight ravine for amazing views on the property. Build your dream home right here!

    Anne Harmody Howard Hanna

    0 Cedar Rd, Chesterland, OH 44026
  • /14

    $529,900

    • Land
    • 65 Acres
    • $8,152 per Acre

    9448 Mayfield Rd, Chesterland, OH 44026

    This rare offering features more than 65 acres of unimproved land across two parcels, located only 2 miles from Downtown Chesterland. With over 500 feet of road frontage, easy access, and utility connections available for power, this property combines privacy with convenience. Septic and well water options offer independence, providing an excellent foundation for future plans. Currently used as

    Greg Erlanger Keller Williams Citywide

    9448 Mayfield Rd, Chesterland, OH 44026
  • /23

    $150,000

    • 3 Beds
    • 1.5 Baths
    • 1,288 Sq Ft

    7501 Mayfield Rd, Chesterland, OH 44026

    Endless potential with this gutted ranch home set on a spacious 1-acre lot with a barn and shed. Whether you're looking to create your dream home or invest in a promising property, this blank slate offers a solid foundation and plenty of room to grow. Surrounded by trees and open space, enjoy the peace of country living with the convenience of nearby amenities on the main road. Bring your vision

    Kylie Houlahan Keller Williams Chervenic Rlty

    7501 Mayfield Rd, Chesterland, OH 44026
  • /31

    $324,900

    • 3 Beds
    • 1.5 Baths
    • 1,408 Sq Ft

    13251 Hickory St, Chesterland, OH 44026

    Beautifully updated ranch in a quiet Geauga County setting with direct access to a scenic park across the street. Enjoy paved walking trails, a long bridge, playground, pavilion, and restrooms—all part of a hidden gem that often feels like your own private retreat. Inside, the home blends modern updates with warm, natural light and authentic hardwood floors. The open flow from the living room to

    TJ Weigel eAgent Real Estate Corp.

    13251 Hickory St, Chesterland, OH 44026
  • /33

    $329,000

    • 3 Beds
    • 2.5 Baths

    12487 Harold Dr, Chesterland, OH 44026

    Arthur Volpe Howard Hanna

    12487 Harold Dr, Chesterland, OH 44026
  • /41

    $675,000

    • 4 Beds
    • 3 Baths
    • 3,371 Sq Ft

    11661 Sherwood Trail, Chesterland, OH 44026

    LOCATION LOCATION LOCATION! Welcome to your charming, rustic retreat in sought after Chesterland - on a private Culdesac street - Did I mention 5+ acres! This home features 4 bedrooms, 3 baths, The Large foyer entrance leads you into the Massive vaulted Great room with soaring wood-burning fireplace! The fully remodeled kitchen with island, gas range and 2 dishwashers for all those

    Shannon Gerome Keller Williams Greater Cleveland Northeast

    11661 Sherwood Trail, Chesterland, OH 44026
  • /43

    $535,000

    • 5 Beds
    • 4.5 Baths
    • 2,974 Sq Ft

    12931 Westchester Trail, Chesterland, OH 44026

    This flexible 4-5 bedroom Chesterland colonial is designed to grow and shift with you. it’s perfect for multigenerational living, blended families, or anyone craving a home that adapts as life evolves. Step into a living room where a gas fireplace wrapped in custom built-ins sets the tone for holiday moments, slow mornings, and the calm rhythm of daily life. The kitchen offers generous storage &

    Annalie Glazen Berkshire Hathaway HomeServices Professional Realty

    12931 Westchester Trail, Chesterland, OH 44026
  • /28

    $450,000

    • 4 Beds
    • 2.5 Baths

    12791 Morning Glory Trail, Chesterland, OH 44026

    Great home, Great location nestled in Geauga County ! This one owner’s home is waiting for your magical decoration! The upstairs is complete with a master bedroom walk-in-closet & master bedroom, 3 additional bedrooms that share a full bath. The sprawling first floor has an eat-in-kitchen and a dining room that will be the center for entertainment, with a slider to step out onto the four-season

    David Fulton Da Vinci Fine Homes, LLC.

    12791 Morning Glory Trail, Chesterland, OH 44026
  • /2

    $165,000

    • Land
    • 2.87 Acres
    • $57,491 per Acre

    0 Merrie Ln, Chesterland, OH 44026

    Michael Petterson Howard Hanna

    0 Merrie Ln, Chesterland, OH 44026
  • /38

    $315,000

    • 3 Beds
    • 1.5 Baths
    • 1,590 Sq Ft

    8075 Mulberry Rd, Chesterland, OH 44026

    Welcome to this 3-bedroom, 1.5-bath split-level set on a private 1.6-acre wooded lot in a desirable Chesterland location. Enjoy the peaceful setting, spacious yard, and the convenience of being close to town.

    Richard Piraino Howard Hanna

    8075 Mulberry Rd, Chesterland, OH 44026
  • /50

    $725,000

    • 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
  • /49

    $4,595,000

    • 6 Beds
    • 8 Baths
    • 14,995 Sq Ft

    7955 Gray Eagle Chase, Gates Mills, OH 44040

    Set upon more than five acres of secluded, wooded grounds, this extraordinary Tony Paskevich designed French Country residence embodies timeless elegance, uncompromising craftsmanship, and countless thoughtful renovations. A private retreat of remarkable beauty that blends classic design with modern luxury. Double doors open to a grand foyer with a sweeping spiral staircase. The family room

    Terry Young Keller Williams Greater Metropolitan

    7955 Gray Eagle Chase, Gates Mills, OH 44040

Why Live in Chesterland

Chesterland, OH, offers a blend of suburban comforts and countryside calm, situated between Cleveland's suburbs and expansive farmlands. This community has seen significant residential growth over the past decade, transitioning from rural farmland to a rural suburb. Homebuyers are drawn to Chesterland for its spacious lots and lower home prices compared to nearby areas. The housing styles include ranch-style homes, Colonial Revivals, split-level houses, and Cape Cods, all set on roomy lots with mature trees. The highly rated West Geauga Local School District serves the area, providing strong educational programs, including technical career courses for high school students. Chesterland's main roads, State Route 306 and Highway 322, offer quick access to Interstate 271 and downtown Cleveland, with Cleveland Hopkins International Airport just a 30- to 40-minute drive away. Local parks such as Chester Township Park and Bessie Benner Metzenbaum Park feature nature trails, athletic courts, and sledding hills, providing ample outdoor activities. The community's commercial hub near the main intersection includes various businesses, eateries, and essential services like Giant Eagle Supermarket and Discount Drug Mart. Chesterland also hosts numerous community events, including concerts, markets, and the annual Winterfest, fostering a strong sense of local engagement.

Frequently Asked Questions

What is the average home price in Chesterland, OH?
Homes for sale in Chesterland, OH have an average home price of $378,282.
How many homes have sold over the last 12 months in Chesterland, OH?
113 homes have sold in Chesterland, OH over the last 12 months.
What are the most popular zip codes in Chesterland, OH?
The most popular zip codes in Chesterland, OH include 44026, 44040, 44022, 44072 and 44094.
How much do you need to make to afford a house in Chesterland?
The median home price in Chesterland is $375,000. If you put a 20% down payment of $75,000 and had a 30-year fixed mortgage with an interest rate of 6.21%, your estimated principal and interest payment would be $1,840 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $79K a year to afford the median home price in Chesterland. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Chesterland, OH?
Chesterland, OH has highly rated public and private schools. Some of the best schools in Chesterland based on Niche Grades are Hawken Upper School, Orange High School and Ballard Brady Middle School. Browse all the schools in Chesterland, OH to learn more.

Home Trends in Chesterland, OH

Housing Trends

Median Sale Price
$365,000
Median Single Family Sale Price
$355,000
Average Price Per Sq Ft
$167
Number of Homes for Sale
11
Last 12 months Home Sales
113
Months of Supply
1.20
Median List Price
$375,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
16%
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