16

Chesterland, OH Houses 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
  • /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
  • /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

Why Live in Chesterland

Chesterland blends suburban comforts with countryside calm, offering a unique living experience between Cleveland's suburbs and expansive farmlands. The community has seen significant residential growth over the past decade, transitioning from rural farmland to a rural suburb with spacious lots and lower home prices compared to nearby areas. Homebuyers are drawn to Chesterland for its roomy lots and tranquil environment, featuring ranch-style homes, Colonial Revivals, split-level houses, and Cape Cods with sprawling lawns and mature trees. The highly rated West Geauga Local School District serves the area, providing excellent educational opportunities including technical programs 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 feature nature trails, athletic courts, and sledding hills, with Chester Township Park and Bessie Benner Metzenbaum Park being popular spots for outdoor activities. Commercial options are concentrated around the major intersection, including fast food chains, cafes, and local businesses like Victoria's Bakery and Chesterland Tavern. Community organizations host various events throughout the year, such as concerts, flea markets, and Winterfest, fostering a strong sense of community.

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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