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Chesterland, OH Homes for Sale

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  • /50

    $350,000

    • 3 Beds
    • 2 Baths
    • 1,856 Sq Ft

    12789 Manchester Dr, Chesterland, OH 44026

    Where timeless design meets modern luxury! Covering what’s not obvious first: The roof, gutters, windows, siding, concrete, a/c, water tank, electrical service feed, septic system, yard drainage, kitchen and bath renovations, flooring, paint - its ALL done within the last 11 years and MANY done within the last 2 years (list available). In addition to the extensive list of HUGE value items, garage

    Agent Photo

    Ben Murphy

    EXP Realty, LLC.

    (440) 671-7265

    12789 Manchester Dr, Chesterland, OH 44026
  • /44

    $437,500 Open Sun 1PM - 3PM

    • 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) 294-4796

    8585 Carmichael Dr, Chesterland, OH 44026
  • /15

    $350,000

    • Land
    • 2.5 Acres
    • $140,000 per Acre

    7959 Battles Rd, Gates Mills, OH 44040

    Remarkable Opportunity! Build your dream house in the tranquil Village of Gates Mills! 2.5 Acres off CountyLine Road just north of Mulberry. Low traffic area with a private wooded setting, yet close to shopping, schools, medical and highways! The original house has been removed and cleared and the former pool was removed and filled. The property benefits from a bonus, oversized storage garage

    Agent Photo

    Seth Task

    Berkshire Hathaway HomeServices Professional Realty

    (440) 271-8627

    7959 Battles Rd, Gates Mills, OH 44040
  • /50

    $425,000

    • 3 Beds
    • 2.5 Baths
    • 3,445 Sq Ft

    12376 Heath Rd, Chesterland, OH 44026

    NESTLED IN A PRIVATE WOODLAND SANCTUARY, this extraordinary Frank Lloyd Wright-inspired home harmoniously embraces its breathtaking 10-acre canvas. Rich wood and native river rock stone create an unparalleled retreat that must be experienced to be believed.The multi-level main residence features TWO DRAMATIC STONE FIREPLACES, a great room flooded with natural light through abundant windows,

    Jerry Kayser Keller Williams Chervenic Rlty

    12376 Heath Rd, Chesterland, OH 44026
  • /38

    $449,900

    • 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
  • /40

    $415,000 Open Sun 11AM - 1PM

    • 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
  • /37

    $415,000 Open Sun 2PM - 4PM

    • 3 Beds
    • 2 Baths
    • 1,900 Sq Ft

    12905 Cherry Ln, Chesterland, OH 44026

    Do not miss this tastefully updated, recently expanded, move-in ready ranch on one very private acre of land! The charming front porch welcomes you inside where you'll immediately notice the open concept floor plan adorned with cathedral ceilings and a spacious eat-in kitchen. The kitchen is equipped with stainless steel appliances (including a beverage refrigerator), soft close cabinets, ample

    Amy Smedira EXP Realty, LLC.

    12905 Cherry Ln, Chesterland, OH 44026
  • /28

    $449,000

    • 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
  • /44

    $599,900

    • 4 Beds
    • 3 Baths
    • 2,721 Sq Ft

    7161 Old Mill Rd, Chesterland, OH 44026

    Welcome to 7161 Old Mill Road in Chesterland, where quiet country living meets effortless sophistication. Set behind iron gates along historic Old Mill Road, this 2.5-acre wooded retreat offers privacy while remaining close to everything the East Side has to offer, and being right on the border of Gates Mill. Rolling lawn, mature trees, and newly planted white pines create a peaceful and private

    Anthony Latina RE/MAX Crossroads Properties

    7161 Old Mill 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
  • /31

    $309,900

    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    8304 Cedar Rd, Chesterland, OH 44026

    Welcome to this fully renovated home offering modern updates, functional design, and plenty of space both inside and out. Situated on a generous 1.30 acre lot, this property provides the perfect blend of privacy and convenience with room to enjoy outdoor living. This home has undergone a complete rehab, featuring new siding, new windows, updated electrical, a new furnace, and a new garage floor,

    Carly Sablotny Keller Williams Living

    8304 Cedar Rd, Chesterland, OH 44026
  • /24

    $189,900

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    13268 Shady Ln, Chesterland, OH 44026

    Enjoy One Floor living in this cozy Ranch set on 1.38 Acres! This charming home offers 2 bedrooms, 1 full bath, Foyer, Living Room, Bonus/Office, Eat-in Kitchen & 1st floor Laundry Room with newer vinyl flooring. Newer vinyl siding, windows & Roof. 1-car attached garage plus carport. Large yard with shed/outbuilding for additional storage. Newer septic system 2017. Great location....Close to the

    Dan McCaskey RE/MAX Revealty

    13268 Shady Ln, Chesterland, OH 44026
  • /43

    $264,900

    • 2 Beds
    • 1 Bath

    8564 Cedar Rd, Chesterland, OH 44026

    Move right in to this beautifully completely remodeled home set on nearly an acre in the heart of Chesterland! This turnkey property has been thoughtfully updated from top to bottom and is truly ready for immediate occupancy. Step inside to discover a brand-new kitchen featuring all-new cabinetry, quartz countertops, and a spacious layout with a comfortable eating area that opens seamlessly to

    Michael Kaim Real of Ohio

    8564 Cedar Rd, Chesterland, OH 44026
  • /2

    $1,200,000

    • Land
    • 10.82 Acres
    • $110,906 per Acre

    12513 Chillicothe Rd, Chesterland, OH 44026

    One of the most valuable pieces of undeveloped land in the center of Chesterland. Call to schedule a meeting to discuss research that has been done and the possibilities for development.

    Eric Uchbar Keller Williams Greater Metropolitan

    12513 Chillicothe Rd, Chesterland, OH 44026
  • /37

    $1,722,000

    • 5 Beds
    • 4.5 Baths
    • 4,866 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
  • /49

    $3,995,000

    • 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 $400,054.
How many homes have sold over the last 12 months in Chesterland, OH?
112 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 $384,950. If you put a 20% down payment of $77,000 and had a 30-year fixed mortgage with an interest rate of 6.3%, your estimated principal and interest payment would be $1,910 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $82K 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 West Geauga High School. Browse all the schools in Chesterland, OH to learn more.

Home Trends in Chesterland, OH

Housing Trends

Median Sale Price
$374,000
Median Single Family Sale Price
$373,000
Average Price Per Sq Ft
$171
Number of Homes for Sale
10
Last 12 months Home Sales
112
Months of Supply
1.10
Median List Price
$384,950
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
17%
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