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Chesterland, OH Homes for Sale

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  • /50

    $575,000

    Open Sun 1PM - 3PM
    • 4 Beds
    • 2.5 Baths
    • 3,130 Sq Ft

    11425 Peachtree Dr, Chesterland, OH 44026

    Welcome to your own private retreat in Chester Twp. Tucked away at the end of a quiet cul-de-sac, this well-maintained 4-bedroom, 2.5-bath home sits on 4.4 picturesque acres, offering the perfect balance of privacy, space, and everyday convenience. Inside, you'll find over 3,100 sq.ft. of living space designed for both family life and entertaining. The spacious family room and study open to a

    Agent Photo

    Feliz Colon

    Keller Williams Living

    11425 Peachtree Dr, Chesterland, OH 44026
  • /49

    $750,000

    • 4 Beds
    • 5 Baths
    • 3,350 Sq Ft

    12145 Reserve Ln, Chesterland, OH 44026

    Nestled on a beautifully landscaped 1.74-acre cul-de-sac lot in desirable Chesterland, this brick Transitional Colonial offers timeless style, thoughtful updates, and exceptional privacy. Set back from the road and surrounded by mature trees, the property provides a peaceful setting while remaining close to everyday conveniences. Inside, a spacious floor plan features a dramatic step-down great

    Sarah Hendershot Redfin Real Estate Corporation

    12145 Reserve Ln, Chesterland, OH 44026
  • /45

    $995,000

    • 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
  • /27

    $309,000

    Open Sun 1PM - 2:30PM
    • 4 Beds
    • 2.5 Baths
    • 2,381 Sq Ft

    11709 Pinewood Trail, Chesterland, OH 44026

    Opportunity Knocks! Bring your vision and unlock the incredible potential of this spacious 4-bedroom, 2.5-bath center hall Colonial on a private, wooded lot in the highly desirable W. Geauga School District. This home presents an exceptional opportunity for investors, flippers, or buyers looking to build instant equity through renovations. Inside, you'll find a fantastic floor plan featuring a

    Lynn Large EXP Realty, LLC.

    11709 Pinewood Trail, Chesterland, OH 44026
  • /37

    $1,295,000

    $200K PRICE DROP
    • 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
  • /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
  • /41

    $799,000

    Open Sat 12PM - 2PM
    • 5 Beds
    • 3 Baths
    • 4,023 Sq Ft

    11865 Africa Acres Dr, Chesterland, OH 44026

    Nestled on 17 breathtaking private acres in Chesterland, this charming century home offers the perfect blend of timeless character and peaceful country living. Surrounded by mature trees, rolling landscapes, and the soothing sounds of a beautiful creek winding through the backyard, this one-of-a-kind property is a true retreat. The home has been thoughtfully maintained and features a brand-new

    Santino Perfetto Howard Hanna

    11865 Africa Acres Dr, Chesterland, OH 44026
  • /43

    $334,000

    $33K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 3,051 Sq Ft

    13480 Shady Ln, Chesterland, OH 44026

    Rare opportunity to own a spacious 4-bedroom ranch in the highly sought-after West Geauga School District! Offering nearly 2,000 square feet of thoughtfully designed living space, this home features a generous family room and private primary suite addition completed in 2018, creating the perfect blend of comfort and functionality. The inviting floor plan offers plenty of room to gather, while the

    Kelsey Bezdek Howard Hanna

    13480 Shady Ln, Chesterland, OH 44026
  • /28

    $430,000

    $20K PRICE DROP
    • 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
  • /45

    $529,900

    $60K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,252 Sq Ft

    7981 Mulberry Rd, Chesterland, OH 44026

    Beautifully updated 4 bedroom, 2.5 bathroom colonial situated on 3.05 picturesque acres. The first floor offers a spacious living room, formal dining area, eat-in kitchen, convenient half bathroom, first-floor laundry, and a cozy family room with a fireplace. Sliding doors from the family room lead to the stone patio, perfect for relaxing or entertaining while enjoying the scenic backyard views.

    Eric Uchbar Keller Williams Greater Metropolitan

    7981 Mulberry Rd, Chesterland, OH 44026
  • /28

    $299,900

    • 4 Beds
    • 2.5 Baths
    • 1,638 Sq Ft

    13099 Dorothy Dr, Chesterland, OH 44026

    Welcome to 13099 Dorothy Drive, a beautifully maintained 4-bedroom, 2.5-bath ranch nestled on a private 1.33-acre wooded lot in desirable Chesterland. Thoughtfully designed for comfortable one-floor living, this home offers a spacious and versatile layout with room for everyone. The main living areas flow seamlessly together, featuring a bright living room, inviting family room, formal dining

    Anthony Latina RE/MAX Crossroads Properties

    13099 Dorothy Dr, 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
  • /50

    $1,924,500

    $71K PRICE DROP
    • 4 Beds
    • 5 Baths
    • 5,184 Sq Ft

    650 County Line Rd, Gates Mills, OH 44040

    Welcome to this stunning custom built French Normandy style home offering luxury, comfort, and breathtaking views throughout. Step inside to a bright and open foyer that leads to the elegant dining room and impressive two-story great room featuring a dramatic floor-to-ceiling fireplace wall and expansive windows overlooking the private backyard. The great room flows seamlessly into the spacious

    Angelo Marrali Howard Hanna

    650 County Line Rd, Gates Mills, OH 44040
  • /45

    $3,495,000

    $1M PRICE DROP
    • 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 $426,401.
How many homes have sold over the last 12 months in Chesterland, OH?
114 homes have sold in Chesterland, OH over the last 12 months.
What is the average household income in Chesterland, OH?
The average household income in Chesterland, OH is $111K.
What are the most popular zip codes in Chesterland, OH?
The most popular zip codes in Chesterland, OH include 44026, 44072, 44040, 44022 and 44094.
How much do you need to make to afford a house in Chesterland?
The median home price in Chesterland is $389,000. If you put a 20% down payment of $77,800 and had a 30-year fixed mortgage with an interest rate of 6.66%, your estimated principal and interest payment would be $2,000 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $86K a year to afford the median home price in Chesterland. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Chesterland is $111K.
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, West Geauga High School and Robert C. Lindsey Elementary School. Browse all the schools in Chesterland, OH to learn more.

Home Price Trends

Median Sale Price
$380,000
Median Single Family Sale Price
$384,900
Median 2 Bedroom Sale Price
$80,000
Average Price Per Sq Ft
$169
Number of Homes for Sale
11
Last 12 months Home Sales
114
Months of Supply
1.20
Median List Price
$389,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
16%
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