Chesterland, OH Homes for Sale

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Newest Chesterland, OH Homes for Sale

$475,000

4 Beds ⋅ 3 Baths ⋅ 5254832 MLS

Welcome to your peaceful wooded escape engineered for modern efficiency. Tucked away on 5.1 private acres across two pristine parcels at the end of a quiet, low-traffic cul-de-sac, this fully modernized 4-bedroom, 2.5-bathroom home seamlessly fuses an intentional lifestyle with top-tier smart efficiency. Designed for an effortless indoor-outdoor flow, the thoughtful layout centers around dual expansive family rooms, a formal dining area, and tranquil 3-season retreat immersed in nature. At the heart of the home is a family focused chef's kitchen curated with custom KraftMaid cabinetry, quartz stone counters, a central prep island, and sleek induction cooking. The culinary space comes fully equipped with a premium Samsung French Door refrigerator featuring integrated reverse osmosis water filtration and a seamless Fisher & Paykel two-drawer dishwasher. The interior has been completely elevated with a 2026 design refresh, featuring an inviting warm neutral color scheme in all living areas, brand-new vanities, plush carpeting, and minimalist modern light fixtures. Seamless smart security and connectivity abound, featuring a Level-2 EV garage charger, a facial-recognition smart lock, and a Lorex 8-camera high-definition security network. Future-proofed against the elements, the home boasts an elite, self-sustaining infrastructure powered by Geothermal heating and cooling, an eco-conscious smart hybrid water heater, and an upgraded electrical setup, including a massive 22kW Generac whole-house generator paired with a battery backup system. Reimagined in 2021, the exterior showcases a striking exposed-wood porch, a premium Trex deck, a new roof, gutters, high-efficiency windows and updated architectural lighting. Your private estate comes completely turn-key, including all premium kitchen and laundry appliances, the outdoor hot tub, and a garden tractor with a leaf vacuum system and accompanying tools. This isn't just a home. It's an absolute lifestyle upgrade.

7925 Pear Tree Drive, Chesterland

$484,900

4 Beds ⋅ 3 Baths ⋅ 5254320 MLS

A PRIVATE 3-ACRE RETREAT IN CHESTERLAND'S COVETED ORCHARD HILL! Welcome to 11465 Peachtree Drive, where peaceful country living meets the comfort of an exceptionally cared-for home. Nestled in an intimate enclave of just 16 residences on approximately 3 to 4.5 acres each, this stately 4-bedroom, 2.5-bath colonial offers a rare blend of space, serenity and privacy. Beautiful grounds create an estate-like setting for relaxation and unforgettable gatherings. Entertain on the expansive deck, unwind in the impressive glass-enclosed bonus room, or enjoy the quiet beauty of your own three-acre haven. There's abundant room for outdoor recreation, pets and play, all surrounded by a remarkable sense of seclusion. Inside, discover comfortable living spaces, four bedrooms, a finished basement offering added versatility, generous storage and an attached 2-car garage. ANOTHER REASON TO LOVE CHESTERLAND? THE SCHOOLS! West Geauga High School ranked #2 statewide among public high schools by Performance Index, West Geauga Middle School ranked #8 among public middle schools, and the district earned Ohio's highest overall 5-Star Rating! Beyond the classroom, stroll to nearby Patterson Fruit Farm for cherished seasonal traditions and explore the scenic Geauga Park District. Shopping, dining and entertainment in Chardon and Mayfield Heights are conveniently close, with access to I-271 and I-90. Here, you can enjoy the best of both worlds: the tranquility of a private country estate and the convenience of nearby amenities. EXPERIENCE CHESTERLAND & ORCHARD HILL LIVING AT ITS FINEST!

11465 Peachtree Drive, Chesterland

$295,000

3 Beds ⋅ 2 Baths ⋅ 5252966 MLS

Enjoy One Floor living in this sprawling Ranch in the heart of Chester Twp! This wonderful home offers approx 1800 sqft of living space with 3 bedrooms, 1.5 baths, newer LVT plank flooring, freshly painted interior and desirable open floor plan. Living Room with new large picture window is open to the Eat-Kitchen with all appliances including brand new dishwasher. Family Room with brick wood burning fireplace. 3 generous sized bedrooms. Updated full bath with double sink vanity & skylight. 3-Season Sunroom with sliders to patio with outdoor brick fireplace & firepit overlooking private backyard. Large Laundry/Mudroom with cabinetry for storage, ceramic floors and half bath complete the main level. Finish the full basement for additional living space. Many updates include: New Roof 2023, water softener 2023, A/C 2020 & newer vinyl windows. Home is wired for generator. Nature stone flooring in both Sunroom & attached 2+car garage. Bring your finishing touches to make this home your own! West Geauga Schools.

12803 Lynn Drive, Chesterland

$570,000

3 Beds ⋅ 3 Baths ⋅ 5249938 MLS

Make this spacious, secluded ranch home on 5 wooded acres in Chesterland a home of memories!!! Welcome to your private retreat in Chesterland. Set on 5 wooded acres, this spacious 3-bedroom, 2-full-bath, 1-half-bath ranch offers approximately 3,100 square feet of comfortable living space surrounded by natural beauty and privacy. Step inside to discover beautiful natural woodwork throughout, abundant natural light, and a welcoming open floor plan designed for both everyday living and entertaining. The spacious dining room provides plenty of space for family gatherings, while the eat-in kitchen provides for a cozy, relaxed morning breakfast. The over sized master bedroom is a true retreat, featuring a step-out to the back patio and an impressive master bathroom with a jetted tub, stand-up shower, and Jack-and-Jill vanity. A generously sized living room and formal dining room flow into plenty of flexibility for family and guests. A cozy wood paneled office with wood burning fireplace make working from home a pleasure. Outside, enjoy the serenity of 5 wooded acres in a secluded setting. The property offers an expansive barn, perfect for your own livestock or creative usage. Enjoy the attached two car garage for snow/rain free entry from your vehicles to your new home. Additional features include a newer roof, newer furnaces, and an independent generator, providing added convenience and peace of mind. This exceptional Chesterland property combines space, privacy, natural character, and functionality with the beauty of a wooded 5-acre setting. A wonderful opportunity to enjoy the best of peaceful country living while remaining part of the West Geauga community.

11226 Sperry Road, Chesterland

$359,000

3 Beds ⋅ 2 Baths ⋅ 5244624 MLS

Your own private pond on more than four wooded acres in Chester Township, with West Geauga Schools and an address that puts everything within easy reach. The setting alone would be enough, but the inside has already been updated top to bottom. The kitchen is the centerpiece. Quartz countertops and custom Amish-built soft-close cabinetry set the tone, including a pair of pull-out pantries that put everything within reach. A generous L-shaped island anchors the room with built-in bench seating, and matching Samsung stainless appliances, an oversized farmhouse sink, and a white subway tile backsplash finish the space. New LVP flooring runs throughout, and an oversized custom slider opens the room to the deck. Just beyond, the living room offers brand-new carpet and a large wood-burning fireplace and stove, the room you'll want all winter. A private office, first-floor laundry, and an updated full bath complete the main level. Upstairs are three oversized bedrooms with new flooring, one of them overlooking the pond, along with an updated full bath featuring a double vanity and a deep soaker tub. Fish it, skate it, walk it, or just watch it from the window. On four-plus acres in Chester, the possibilities are endless.

13419 Sperry Road, Chesterland

$289,900

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

$40,000

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

$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

$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

$319,900

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

$279,900

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

$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

$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

$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

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Chesterland, OH Homes for Sale

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