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$2,750,000
5 Beds 8 Baths 5241609 MLS
Thirty-two acres in Chesterland, reached by a long gravel drive that winds through mature woods before the house comes into view. Two parcels, two homes, a stalled barn, ponds, and open pasture. Inside the main house, a two-story foyer, a coffered family room with an arched fireplace, a kitchen under a vaulted wood ceiling, a paneled office with built-ins, and a greenhouse under glass. Five bedrooms, one on the main floor. A vaulted recreation room with room enough for billiards and a grand piano. Below, a private whiskey and wine cellar. Outside, a tiered deck with a built-in outdoor kitchen looks over the pool and the pond beyond it. A detached garage with a wood shop and clearance for full-size equipment. Past the pasture fence, the barn and open ground for whatever comes next. A second drive leads through the trees to the guest house. Its own parcel, its own address, its own kitchen and garage. Somewhere people can actually live. A third adjoining parcel, with a house of its own, is available separately. Room for three generations, and enough land between them. Someday they'll say it started here. Horses, donkey, chickens, tractors, and farm equipment do not convey.

12157 Sperry Road, Chesterland

Listing Courtesy of: Terry Young, Terryyoung@theyoungteam.com With Keller Williams Greater Metropolitan

$1,295,000
5 Beds 5 Baths 5215468 MLS
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 luxury. A charming one bedroom carriage house with a full bath and private patio provides an ideal guest residence, while six-car garage capacity offers both convenience and prestige. Resort-inspired outdoor living takes center stage with a stunning in-ground saltwater pool, elegant pool house, tranquil pond, fire pit, lush gardens, barn, shed, and impeccably curated landscaping that transforms every view into a work of art. A whole-home generator adds seamless peace of mind.

7885 Pear Tree Drive, Chesterland

Listing Courtesy of: Danielle Angie, danielleangie@mcdhomes.com With McDowell Homes Real Estate Services

$995,000
5 Beds 5 Baths 5219403 MLS
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 throughout the main level. French doors open to a home office, while the opposite side reveals a formal dining room designed for large celebrations. The heart of the home is the expansive gourmet kitchen, perfectly crafted for both daily living and grand entertaining. With two large islands, dual sinks, granite countertops, and a generous walk-in pantry, it is as functional as it is beautiful. The adjoining sun-filled dining area and vaulted sunroom open seamlessly to the patio, creating an easy flow for indoor-outdoor living. Gather in the grand living room, where a striking stone fireplace and custom built-ins set the stage for cozy evenings and lively get togethers. Upstairs, the luxurious primary suite offers a serene retreat with vaulted ceilings, an oversized walk-in closet, and a spa-inspired bath. Four additional bedrooms, connected by Jack-and-Jill baths, provide space and comfort for family and guests. The walk-out lower level is designed for recreation and relaxation, with a spacious family room, wet bar, game room, and a full bathroom that includes a steam room attachment for a private spa experience, plus a bonus room that doubles as a sixth bedroom. French doors open to a private patio, extending the living space outdoors to your own private sanctuary, an expansive backyard perfect for weekend gatherings and entertaining. With an attached three-car garage and a detached two-car garage with loft area, there is no shortage of space. Recent improvements include a new roof 2026, 2 new furnaces 2026, 2 newer ac units, and a whole home generator!

7775 Woodlands Trail, Chesterland

Listing Courtesy of: Terry Young, Terryyoung@theyoungteam.com With Keller Williams Greater Metropolitan

$425,000
4 Beds 3 Baths 5148756 MLS
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 room. The living room has plenty of space to spread out and relax. Did you see that there is a First-floor laundry room! The basement has endless possibilities for a recreation room, workshop, and possible office space or gym or second kitchen. The yard once had a full sand volleyball court with plenty of parking in the oversized driveway that leads into the 3-car garage! Do not forget about the small creek that winds its way through the back corner of the yard backyard. 2023: New Furnace & Hot Water Tanks, 2024: New Roof, 2025 New Driveway.

12791 Morning Glory Trail, Chesterland

Listing Courtesy of: David A Fulton, davidismyrealtor@gmail.com With Da Vinci Fine Homes, LLC.

$400,000
5 Beds 3 Baths 5243801 MLS
Spacious Split-Level Home with Versatile Living Space! This generously sized split-level home offers a functional layout with multiple living areas. The large Living Room features vaulted ceilings that create an open, airy feel, while the vaulted Dining Room provides an inviting space for everyday meals and special occasions. The large Eat-In Kitchen is designed for functionality, offering a practical layout for meal preparation, casual dining, and entertaining. The spacious bedrooms provide comfortable accommodations with room for furnishings, personal belongings, and individual needs. Three full baths add privacy and convenience for both household members and guests. The basement offers additional storage. The Family Room serves as a comfortable gathering space centered around a wood-burning fireplace, creating a warm setting for relaxing or entertaining. From the Family Room, step outside to the expansive concrete patio, which provides an excellent area for outdoor dining, gatherings, and enjoying the surrounding landscape. The tree-lined backyard offers a private setting with space to enjoy the outdoors, while the impressive two-story pole barn adds exceptional versatility. Whether you need room for vehicles, equipment, a workshop, hobbies, or additional storage, this outbuilding provides a range of possibilities. Also, additional cars can fit in the pole barn. With its spacious interior, functional floor plan, multiple living areas and private outdoor setting, this property offers the flexibility to accommodate a variety of lifestyles. Come see the space, functionality, and possibilities for yourself—schedule your private showing today and don't miss this opportunity!

9284 Mayfield Road, Chesterland

Listing Courtesy of: Art Obleton Jr., artobletonjr@gmail.com With EXP Realty, LLC.

$340,000
3 Beds 2 Baths 5234209 MLS
If you’ve been searching for a nicely maintained home with major mechanical updates on a serene setting of over 2.5 acres, look no further! Enjoy peace of mind with significant recent improvements, including a new roof (2022), replacement windows (approx. 2016), and a new exterior electrical box equipped with a whole-house surge protector (2026). Step inside to discover beautiful red oak wood flooring running through the kitchen, dining room, living room, and main-floor laundry room. The heart of the home is the thoughtfully designed kitchen, complete with rich custom maple cabinets, quartz countertops, and sleek stainless steel appliances. Designed for ultimate comfort and easy one-floor living, the main level features 3 spacious bedrooms, 2 full bathrooms, and convenient first-floor laundry. Need even more room to expand? The full unfinished basement offers endless opportunities to create additional living space, a home gym, workshop, or entertainment area tailored to your needs. Enjoy peaceful living with modern updates—schedule your private tour today!

10435 Cedar Road, Chesterland

Listing Courtesy of: Kristen Fischer, kristenfischer@kw.com With Keller Williams Chervenic Rlty

$334,900
4 Beds 2 Baths 5242133 MLS
Mid-Century Charm Meets Modern Living in Desirable Chesterland Welcome to this stunning 1965 residence, designed and built by well-known local developer and architect Frank Bagaria during the height of mid-century architectural style. Set on a generous 1.14-acre lot, this 4-bedroom, 2-bath home offers the space, character, and craftsmanship that's increasingly hard to find. Step inside to an open, airy layout anchored by a dramatic cathedral beam ceiling that immediately sets this home apart. A flexible main floor room offers the perfect space for formal dining or a comfortable living room — whichever suits your lifestyle. This level also includes a spacious 16 x 20 bedroom addition completed in 1986. The kitchen flows easily into the main living areas and opens directly to the upper patio and backyard, making indoor-outdoor entertaining effortless. Upstairs, you'll find three spacious bedrooms and a full bath, including one with private access to a deck. The lower level features a bright and welcoming family room warmed by a classic wood-burning fireplace, with a large sliding door leading out to the lower patio and backyard for easy indoor-outdoor living. Just a few steps down, a full bathroom adds everyday convenience. A partial basement offers additional storage or workshop potential, while a large front porch invites you to slow down and enjoy the neighborhood charm that Chesterland is known for.

13037 Stratford Trail, Chesterland

Listing Courtesy of: Catrina Covino, Catrinacovino@hotmail.com With Century 21 Homestar

$325,000
3 Beds 2 Baths 5244661 MLS
This picturesque Chester Township home is beautiful situated on over an acre and offers more than 2,100 square feet of usable living space. With 3 bedrooms, 1.5 baths, multiple living areas and wonderful indoor-outdoor spaces, this charming property has so much to offer. Step inside from the inviting covered front porch into a light and bright living room featuring gleaming hardwood floors and an easy flow into the formal dining area. The updated eat-in kitchen showcases beautiful wood cabinetry, ample counter space, neutral countertops and lovely views of the rear yard. The cozy family room features a gas fireplace, a renovated half bath and access to the stunning four-season room. Complete with its own gas stove and views of the surrounding property, this space is perfect for enjoying crisp fall mornings or relaxing year round. Two bedrooms and a recently updated full bath are also located in the main level. Upstairs, you'll find a spacious third bedroom along with a huge attic area providing an abundance of convenient storage. A mudroom/laundry room is located just off the attached two-car garage, along with a heated 12x16 workshop - an ideal space for an artist, gardener, hobbyist or someone who works from home. The home features a newer reverse osmosis water system. Outside, the paver patio provides the perfect setting for entertaining, dining, or simply enjoying the peaceful and private backyard with recently refreshed landscaping. Offering generous living space, a beautiful setting and plenty of character, this Chester Twp home is ready for its next owner. For added peace of mind, the seller has completed a pre-inspection, which is available upon request.

8525 Kirkwood Drive, Chesterland

Listing Courtesy of: Claire Jazbec, clairejazbec@kw.com With Keller Williams Greater Cleveland Northeast

$324,900
3 Beds 1 Baths 5236901 MLS
Country living, acreage, and the character of a 1920s home come together in a beautiful rural setting. Situated on approximately 3.6 acres in the Northwestern Local School District, this property offers plenty of room to enjoy the outdoors, a spacious yard, and multiple outbuildings. Inside, you'll find the charm you'd expect from an older home along with updates that have been made over the years. The spacious eat-in kitchen features a large center island, providing plenty of room for gathering and entertaining. One of the highlights of the kitchen is the picturesque view of the surrounding property; a great reminder of the peaceful country setting just outside your door. The home does need some repairs and presents an opportunity for its next owner to make additional improvements and updates to suit their style. The front porch will need to be reconstructed or replaced; the property is being sold as-is. The real standout here is the setting. With approximately 3.6 acres, a large yard, outbuildings, and room to spread out, this property offers the space and rural atmosphere that can be difficult to find. Bring your ideas and vision and discover the potential of this charming country property!

3763 Bates Road, Wooster

Listing Courtesy of: Adam P Hanzie, adam@wileshanzie.com With Wiles Hanzie Realty

$305,000
3 Beds 1 Baths 5246391 MLS
Welcome to this completely updated Ranch home that has it all in the desirable Chesterland community! Thoughtful updates & an open floorplan make this move-in ready home an exceptional opportunity! Experience one floor living at its finest! Walk into the front door & you will notice how open this home is from the dining room into the bar area of the gorgeous kitchen and beyond to the family room! Entertaining is easy with this open floorplan! Family room offers a sliding door with inset blinds to the paver patio area with partially fenced rear yard! Updates include: New fence, garage door & front storm door (2026); vinyl siding, washer & dryer (2025); water softener (2022); complete house renovation 2021 that includes windows, doors, slider to patio, gorgeous kitchen remodel, bathroom gutted & remodeled, two electric panels, duct work, flooring, stainless steel kitchen appliances, laundry room, light fixtures, and added a gas heater in the family room. Outside the generous back yard features a spacious paver patio and storage shed as well as a garden area. The combination of open layout, thoughtful updates, and desireable location, make this home ready to welcome its next owners!

8264 Cedar Road, Chesterland

Listing Courtesy of: Stephanie D Scheiber, stephaniedscheiber@gmail.com With HomeSmart Real Estate Momentum LLC

$299,900
3 Beds 2 Baths 5232822 MLS
Bring your ideas and make this property your own! Situated on a scenic 1-acre lot in the desirable West Geauga Local School District, this 3-bedroom, 1.5-bath ranch is full of potential for buyers looking to renovate and build equity. The home offers the convenience of one-floor living with a practical layout and plenty of outdoor space to enjoy. While the interior may need some updates, the peaceful setting and sought-after location make this a fantastic opportunity for anyone looking to customize a home to their own style. Enjoy the privacy and room to roam that comes with a full acre, all while being conveniently located near shopping, parks, and major commuter routes. Bring your vision and unlock the potential this property has to offer! Don't miss your chance to transform this diamond in the rough into something special.

7415 Avon Lane, Chesterland

Listing Courtesy of: Ron Dahlhofer, Ron@woodlakeRE.com With Woodlake Realty LLC

$45,000
2 Beds 1 Baths 5245119 MLS
Welcome to 8701 Mayfield Rd Lot 156! This well-maintained manufactured home offers 2 bedrooms, 1 full bathroom, 919 square feet of comfortable living space, and a convenient carport, all located within a quiet 55+ community in desirable Chesterland. The home has benefited from numerous recent mechanical and appliance upgrades, including a new roof installed in 2017, furnace and central air conditioning in 2022, washer and dryer in 2023, refrigerator in 2021, hot water tank in 2015, and a generator added in 2024. Well water is included with the monthly lot rent, helping simplify your monthly expenses. For added peace of mind, the seller is also including a one-year home warranty through America’s Preferred Home Warranty. Enjoy the relaxed lifestyle Chesterland has to offer, with a peaceful suburban setting, nearby shopping, restaurants, parks, and everyday conveniences, while still providing easy access to surrounding communities and Greater Cleveland. Schedule your private showing today!

8701 Mayfield Road, Chesterland

Listing Courtesy of: Keyano Burgess, keyano.realtor@keysoldit.com With Lokal Real Estate, LLC.

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity™ program of the Multiple Listing Service of Greater Cincinnati. Real estate listings held by brokerage firms other than our company are marked with the Broker Reciprocity™ logo (the small house as shown to the left) and detailed information about them includes the name of the listing brokers. This data is up-to-date as of . Copyright 2026, MLS of Greater Cincinnati, Inc. All rights reserved. Information deemed reliable but not guaranteed.

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The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of the Dayton Area Board of Realtors® MLS IDX Database. Real estate listings from the Dayton Area Board of Realtors® MLS IDX Database held by brokerage firms other than Purtan Technologies, LLC are marked with the IDX logo and are provided by the Dayton Area Board of Realtors® MLS IDX Database. Information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in. Copyright© 2026 Dayton Area Board of Realtors®