Chesterland OH Homes For Sale

View all the homes for sale in Chesterland OH at a median price for all buyers. See pricing and listing details of Chesterland real estate for sale.

Chesterland OH Homes For Sale

$499,000

4 Beds ⋅ 3 Baths ⋅ 5226224 MLS

Welcome to this beautiful one owner colonial nestled on a lovely wooded lot. Enter from the inviting front porch to the huge living room with bay window opening to the formal dining room. The spacious eat in kitchen with all appliances overlooks the backyard. You can watch all the birds as the maple syrup is being boiled in the sugar shack in the yard. The grand family room will be where everyone spends their time with a WBFP, windows overlooking front & back of property & an area for your home office . A complete laundry room w/ extra refrigerator & a half bath are also located on the 1st floor. On the second floor there are 4 big bedrooms including a spacious BDRM w/ ensuite full bath & huge walkin closet. The other full bath has a walkin shower & double vanity. The Rec room downstairs has lots of room for games as well as area for storage. There is an expansive deck overlooking the beautifully landscaped oasis in the backyard. A full house generator for peace of mind. Located on a quiet cul de sac street, the home is close to highways, schools & shopping. Come home to the country, close to everything historic Chesterland has to offer.

12181 W Shiloh Drive, Chesterland

$750,000

4 Beds ⋅ 5 Baths ⋅ 5225746 MLS

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 room with soaring ceilings, a fireplace, custom built-in cabinetry, and beautiful backyard views. The eat-in kitchen is the heart of the home with freshly painted cabinetry (2026), new flooring (2026), a bayed dining area, and adjoining workspace. Granite flooring throughout the main level (2021), formal living and dining rooms, a private first-floor den/office, first-floor laundry with new cabinetry (2023), and two half baths complete the main level. The first-floor primary suite includes a private bath and walk-in closet updated in 2022. Upstairs are three generously sized bedrooms, including one with an updated ensuite bath (2020), a renovated hall bath (2022), hardwood flooring throughout (2022), and a versatile loft ideal as a media room, playroom, or additional living space. Relax or entertain on the expansive rear deck overlooking the private wooded backyard. The 1.74-acre property also features a storage shed, invisible pet fence, and plenty of space to enjoy the outdoors. Additional updates include a new well pump (2025), hot water tank (2026), well pressure tank (2019), leaf gutter guards (2021), generator line, and an attached three-car garage. Combining space, quality, and a highly desirable cul-de-sac location, this is a wonderful opportunity to call Chesterland home.

12145 Reserve Lane, Chesterland

$299,900

4 Beds ⋅ 3 Baths ⋅ 5224421 MLS

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 area, and an eat-in kitchen complete with abundant cabinetry and plenty of space for everyday meals. Three of the bedrooms share a full bath while a standout feature of this home is the attached in-law suite, complete with its own living room, bedroom, and full bathroom, offering exceptional flexibility for multigenerational living, extended guests, or a private retreat. The spacious three-season sunroom overlooks the peaceful backyard and features all new windows and sliding doors installed in 2019, creating the perfect space to relax year-round. Main-floor laundry adds everyday convenience, while the attached garage and expansive driveway provide ample parking. Recent updates include luxury vinyl plank flooring throughout, a new asphalt driveway in 2024, a new water softener in 2024, a new hot water tank in 2025, re-enameled tubs and bathroom sinks, newer septic (2017), and a newer roof (2014). Surrounded by mature trees and offering the ease of ranch living with flexible spaces throughout, this inviting home is ready for its next chapter.

13099 Dorothy Drive, 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

$679,900

4 Beds ⋅ 4 Baths ⋅ 5214799 MLS

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 steel appliances, large island with seating & extends into the dining area anchored by a striking exposed brick wall showcasing a woodburning fireplace, wet bar area & a set of sliders leading to spacious deck areas, making gathering & entertaining easy. The kitchen/dining area flows into the family room & features an additional fireplace & large windows that frame picturesque wooded views. The expansive primary suite is a true retreat featuring dramatic vaulted ceilings w/exposed beams, a wall of windows showcasing treetop views, brick faced fireplace & French doors that open to the ensuite bath. Two additional bedrooms & a full bath complete the 2nd floor. Additional living space in the spacious LL recreation room (currently being used as a bedroom) offering recessed lighting, brick fireplace & walk-out access to an expansive deck with serene views. Outside is over 9 wooded acres including a 2 car attached garage, a chicken coop & so much more! Recent updates include: replaced furnace & central air, added additional parking pad & built chicken coop (2022), replaced washer, dryer, dishwasher, stove, refrigerator & microwave (2023), completed lower level remodel & added walk out deck, replaced siding on front of house, painted entire exterior & replaced carpet to the bedrooms (2025), repaired driveway (2026). Included are all kitchen appliances, washer/dryer & tv mounts. Conveniently located near I-90, I-271, OH-44, restaurants, shopping & other local attractions.

10640 Butternut Road, Chesterland

$529,900

4 Beds ⋅ 3 Baths ⋅ 5212177 MLS

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. The finished basement provides additional living and recreation space. Upstairs features four nicely sized bedrooms and two full bathrooms, including a spacious primary suite. A two car attached garage adds convenience and extra storage. This well-maintained home also features all new storm blinds throughout the property, split system boiler heat with central air, and gravity-flow drainage throughout the home. The basement sump pump is currently used only as a floor drain for the water softener. Major updates include a new high-efficiency hot water heater (2024), new lifetime roof (2024), new Kinetico water softener (2024), new well and pump (2024), brand new carpet (2026), fresh paint (2026), and new flooring (2026). A wonderful blend of modern updates, comfortable living, and peaceful surroundings.

7981 Mulberry Road, Chesterland

$1,200,000

5194492 MLS

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.

12513 Chillicothe Road, Chesterland

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