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Chesterland, OH Homes for Sale

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  • /28

    $525,000

    • 4 Beds
    • 2.5 Baths
    • 2,964 Sq Ft

    12580 Bentbrook Dr, Chesterland, OH 44026

    This charming Colonial features almost 3000 sq feet of space along with 4 bed rooms and 3 bathrooms (2/1). It sits on a quiet and beautiful 5.5 acres in Bentbrook Farms. The back offers incredible views of stunning land leading to a meadow and lake. It has been kept meticulously clean and in good condition with care over the years and is move-in ready, but this dream home is also ready for you to

    Michael Jenoff Century 21 Homestar

    12580 Bentbrook Dr, Chesterland, OH 44026
  • /50

    $498,000

    • 4 Beds
    • 3 Baths
    • 2,470 Sq Ft

    12790 Heath Rd, Chesterland, OH 44026

    Welcome to your dream home in the heart of Chesterland! Nestled on a serene 1.71-acre lot, this completely renovated 4-bedroom, 3-bath beauty offers 2,470 sq ft of luxurious living with modern finishes and timeless charm. Step inside to discover a bright, open layout with new LVP flooring throughout, recessed lighting, and three cozy fireplaces that create warmth and character in every corner.

    Joan Elfein Ohio Broker Direct

    12790 Heath Rd, Chesterland, OH 44026
  • /38

    $625,000

    • 5 Beds
    • 3 Baths
    • 3,326 Sq Ft

    9502 Winchester Valley, Chesterland, OH 44026

    Rare find with full first floor in-law or teen suite with large bedroom, full bath, full additional kitchen and laundry room. Six garage spaces . Car collector or shop craftsman dream. Very well maintained, newer high end windows, beautiful oak hardwood floors throughout some exposed and some under carpet. Could use some decorating with paint and carpet.Corian counters and counter depth

    Marks of Excellence Team RE/MAX Traditions

    9502 Winchester Valley, Chesterland, OH 44026
  • /31

    $479,000

    • 4 Beds
    • 2 Baths
    • 2,796 Sq Ft

    13228 Boulder Glen Dr, Chesterland, OH 44026

    Wonderful original owner colonial ready for a new generation to make this their home. The 5 acre property backs up to the golf course & is wooded for privacy. The brick & sided home was built for a family with a huge spacious living room & dining room with gleaming HDWD floors & expansive windows overlooking the property. The cozy kitchen has maple cabinetry, lots of counter space & all

    Mary Beth O'Neill Keller Williams Greater Cleveland Northeast

    13228 Boulder Glen Dr, Chesterland, OH 44026
  • /14

    $639,610

    • 3 Beds
    • 2.5 Baths
    • 2,303 Sq Ft

    Vacant Land Heath Road - To Be Built, Chesterland, OH 44026

    TO BE BUILT: JEMM Construction's "The Madison", Three Bedroom, First Floor Owner's Suite, Classic Style with All the Touches of Modern Living. 2,303 Total Square Feet, Covered Porch, Foyer Entrance, Beamed Great Room Open to Kitchen and Dining, First Floor Owner's Suite, First Floor Office/Guest Room, Half Bath, Two Additional Bedrooms and Full Bath Upstairs, Full Unfinished Basement, Attached

    Linda Ebersbacher Howard Hanna

    Vacant Land Heath Road - To Be Built, Chesterland, OH 44026
  • /24

    $439,999

    • 2 Beds
    • 1 Bath
    • 2,415 Sq Ft

    12480 Ward Dr, Chesterland, OH 44026

    Great investment opportunity in the heart of Chesterland, Ohio! This all-brick 4-unit complex sits on a spacious 1.1-acre lot with frontage to Chillicothe Road, offering future development potential. Each unit features 2 bedrooms, 1 full bath, a kitchen, and a comfortable family room. The property includes a private parking lot, a 2-car garage, and a storage shed for added convenience. All four

    Mathew Grazia McDowell Homes Real Estate Services

    12480 Ward Dr, Chesterland, OH 44026
  • /46

    $338,500

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

    12084 Heath Rd, Chesterland, OH 44026

    Welcome to your own Story Book Forest home that is nestled on a private 1.51-acre oasis. This home is a charming 4-bedroom, 2.5-bathroom split-level home offering serene views of the Chagrin River. Inside, beautiful wood floors flow through the open-concept kitchen and family room, boasting breathtaking property views. Enjoy year-round comfort in the four-season sunroom, equipped with a split

    Meegan Smolsky Real of Ohio

    12084 Heath Rd, Chesterland, OH 44026
  • /36

    $320,000

    • 4 Beds
    • 2 Baths
    • 1,796 Sq Ft

    7730 Cedar Rd, Chesterland, OH 44026

    This cozym rustic Chesterland ranch has all the warm vibes with huge wooden headers throughout, country wooden cabinets in the kitchen, and a barn door to separate the rear living space from the front. There are 4 bedrooms, a room that would make a great office space, music room or play area with a pellet stove, two full baths (one having a tub while one has a walk-in shower), both a living room

    Julie Hogston Real of Ohio

    7730 Cedar Rd, Chesterland, OH 44026
  • /31

    $419,900

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

    8735 Cedar Rd, Chesterland, OH 44026

    Walk right in to be met by an amazing spiral staircase. This generously sized Colonial at 2,552 sq ft offers 4 bedrooms, 2 1/2 baths, living room, dining room, family room and an enclosed sun porch. Step into the oversized kitchen that is complete with 3 wall ovens, spacious island, plenty of cabinet space, and sliders to a side patio. The home provides plenty of space for comfortable living.

    Anita Butler Howard Hanna

    8735 Cedar Rd, Chesterland, OH 44026
  • /35

    $439,900

    • 3 Beds
    • 2.5 Baths
    • 2,098 Sq Ft

    12845 Morning Glory Trail, Chesterland, OH 44026

    Welcome to this beautifully updated split level home nestled on a serene and private street in Chesterland. Situated on 1.30 acres, this 3 bedroom (potentially 4), 2.5 bath home offers a perfect blend of modern upgrades and timeless comfort. Enjoy two cozy fireplaces in the living rooms, a whole house generator hookup, and a thoughtfully updated layout ideal for everyday living and entertaining.

    Megan Magden Angelotta Howard Hanna

    12845 Morning Glory Trail, Chesterland, OH 44026
  • /49

    $365,000

    • 4 Beds
    • 3 Baths
    • 2,686 Sq Ft

    13443 Lakewood Dr, Chesterland, OH 44026

    Welcome to this Charming, Serene Home situated at 13443 Lakewood Drive in the heart of Chesterland Ohio within West Geauga School District! Set away from the street This Home has an landscaped treed yard, long driveway and paved walkway to the front door. Upon entering you’re welcomed to a small foyer leading to the front living room with its large bay window with a wonderful view of the front

    Cesar Hernandez Lokal Real Estate, LLC.

    13443 Lakewood Dr, Chesterland, OH 44026
  • /50

    $1,395,000

    • 4 Beds
    • 4.5 Baths
    • 9,256 Sq Ft

    12370 Rockhaven Rd, Chesterland, OH 44026

    This one owner custom designed and built stone and cedar "mountain modern" home is absolutely a masterpiece! Sited on a private 3+acre site, this home has an open flowing floor plan designed for grand scale entertaining and luxury living! Upon entering this home, one will notice the incredible ceiling heights, the walls of windows, the spectacular stone fireplaces, and the incredible use of wood

    Adam Kaufman Howard Hanna

    12370 Rockhaven Rd, Chesterland, OH 44026
  • /42

    $299,000

    • 3 Beds
    • 2 Baths
    • 2,976 Sq Ft

    8265 Merrie Ln, Chesterland, OH 44026

    Welcome home! Sitting on a private 1.03-acre lot, this 3-bedroom, 2-bath brick ranch offers the ease of one-floor living in a desirable Chesterland location. This 1,632 sq ft home features an open floor plan with a spacious great room and wood-burning fireplace, flowing into the dining area for comfortable everyday living. All bedrooms are on the main floor, and the primary bedroom includes a

    Richard Piraino Howard Hanna

    8265 Merrie Ln, Chesterland, OH 44026
  • /48

    $399,000

    • 5 Beds
    • 2.5 Baths
    • 3,078 Sq Ft

    8665 Prescott Dr, Chesterland, OH 44026

    Escape the hustle and bustle of everyday life and discover your peaceful sanctuary on this beautiful 1.5 acres, 5 bedrooms, 3 baths, Cape Cod with attached 2-car garage. The main floor of this home features a kitchen with an eat-in area, family room perfect for gatherings, living room, dining room, 2 spacious bedrooms, 1.5 baths and a laundry room. The second floor continues with 3 enormous

    Penelope Coutris Keller Williams Citywide

    8665 Prescott Dr, Chesterland, OH 44026
  • /38

    $390,000

    • 3 Beds
    • 1.5 Baths
    • 2,379 Sq Ft

    12980 W Geauga Trail, Chesterland, OH 44026

    Step into a delightful blend of country comfort and contemporary style in this beautifully maintained Chesterland residence. SO MANY UPDATES. Offering a generous 2,379 square feet of thoughtfully designed living space, this inviting home features three spacious bedrooms and one and a half bathrooms – both recently renovated to perfection! The heart of this home welcomes you with warm, open spaces

    Jennifer Vidmar HomeSmart Real Estate Momentum LLC

    12980 W Geauga Trail, Chesterland, OH 44026
  • /11

    $82,000

    • Land
    • 1.50 Acres
    • $54,667 per Acre

    V/L Heath Rd, Chesterland, OH 44026

    This Breathtaking 1.5 Acre Parcel Offers the Perfect Landscape to Build Your Dream Home. Rare Opportunity As Parcels in West Geauga School District Are Few and Far Between. Majestically Situated on Heath Road with Sunnybrook Preserve Lodge, Geauga Park District Just Down the Street! This Parcel is Approximately 150' x 435', is Wooded and Offers Privacy and Nature Abounding! The Back of This

    Linda Ebersbacher Howard Hanna

    V/L Heath Rd, Chesterland, OH 44026
  • /2

    $175,000

    • Land
    • 2.87 Acres
    • $60,976 per Acre

    0 Merrie Ln, Chesterland, OH 44026

    Michael Petterson Howard Hanna

    0 Merrie Ln, Chesterland, OH 44026
  • /33

    $1,400,000

    • 5 Beds
    • 4.5 Baths

    1450 County Line Rd, Gates Mills, OH 44040

    Great opportunity in Gates Mills! This property offers multiple use, three total lots nestled in a beautiful serene private setting. Live in the present home - or build two more homes on the adjoining lots or simply enjoy your own private haven! Built in 1987 with long, secluded stone winding drive nestled between the two adjoining buildable lots total of almost 10 acres giving you complete

    Carmella Corbo Howard Hanna

    1450 County Line Rd, Gates Mills, OH 44040
  • /50

    $4,900,000

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

    7955 Gray Eagle Chase, Gates Mills, OH 44040

    GREAT NEW PRICE! Exquisite French Country Estate, set on over 5 acres of serene, private grounds. This architectural masterpiece blends timeless elegance with modern luxury in one of the most sought-after settings. The stone and shingle façade, crowned by a slate roof and turrets, evokes effortless country distinction. Stone walkways and terraces wind through meticulously designed gardens,

    Annalie Glazen Berkshire Hathaway HomeServices Professional Realty

    7955 Gray Eagle Chase, Gates Mills, OH 44040
  • /2

    $515,000

    • Land
    • 7 Acres
    • $78,339 per Acre

    1200 County Line Rd, Gates Mills, OH 44040

    Create your dream home on this stunning wooded lot, spanning over 6.5 acres, in the charming village of Gates Mills. Experience peace and tranquility while still being conveniently close to everything you need!

    Adam Kaufman Howard Hanna

    1200 County Line Rd, Gates Mills, OH 44040

Why Live in Chesterland

Tucked between Cleveland's densely populated suburbs and sprawling farmlands, Chesterland blends rural and suburban living. The community's sprawling landscape is a clear break from packed subdivisions, yet homebuyers can still find similar home styles at lower prices. "As the housing market has gotten tighter in surrounding communities, it has pushed homebuyers into this community," says Annalie Glazen, Realtor with Berkshire Hathaway HomeServices Professional Realty, who started her real estate career in Chesterland. "Maybe they weren't originally considering it, but it's turned out to be a really successful and hot real estate market." Residents enjoy being away from busy city life but still have quick access to major highways, retail centers and highly rated schools. Over the past decade, Chesterland has seen significant residential growth, shifting the community's identity from rural farmland to a rural suburb. Thick forests and a few farms still separate subdivisions, but this allows homes to keep their acreage as new construction enters. "People just want a little extra elbow room," Glazen says. "We see people coming from Mayfield or Lyndhurst, where they have quarter-acre

Frequently Asked Questions

What is the average home price in Chesterland, OH?
Homes for sale in Chesterland, OH have an average home price of $375,397.
Are home prices dropping in Chesterland?
Yes, home prices in Chesterland are down 9% in the last 12 months.
How many homes have sold over the last 12 months in Chesterland, OH?
125 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 44118, 44105, 44120, 44060 and 44077.
How much do you need to make to afford a house in Chesterland?
The median home price in Chesterland is $339,900. If you put a 20% down payment of $68,000 and had a 30-year fixed mortgage with an interest rate of 6.77%, your estimated principal and interest payment would be $1,770 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $76K a year to afford the median home price in Chesterland.
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, Robert C. Lindsey Elementary School and West Geauga Middle School. Browse all the schools in Chesterland, OH to learn more.

Home Trends in Chesterland, OH

Housing Trends

Median Sale Price
$330,000
Median Single Family Sale Price
$335,000
Average Price Per Sq Ft
$158
Number of Homes for Sale
16
Last 12 months Home Sales
125
Months of Supply
1.50
Median List Price
$339,900
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
-4%
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