Chesterland OH Real Estate & Homes for Sale

13 Properties Found

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Beds:
3
Baths:
2.00
Sq.Ft.:
1,008
Status:
NEW LISTING
MLS#:
5220568
Type:
Single Family
Subdivision:
Herrick Country Estate
Lot size:
0.69 Acres
Year built:
1963
Courtesy: Ohio Property Group, LLC 419-790-3106
View additional info

ADDITIONAL INFORMATION

Bring your vision and creativity to this rare opportunity in the heart of Chesterland! Located on a quiet dead end street, this 3 bedroom, 2 bath ranch offers convenient single floor living on a spacious 0.69-acre lot. The property backs to a wooded area, creating a peaceful park like setting with plenty of privacy. This home is in need of a complete renovation and is being offered as an excellent opportunity for people looking to customize a home to their exact tastes. Features include vinyl siding, public sewer (a rare find in Chesterland), and a functional ranch layout ready for transformation. Whether you're looking to renovate and resell, create a rental property, or build your dream single-story home, the possibilities are endless. Enjoy the quiet surroundings, generous lot size, and desirable Chesterland location while bringing new life to this property. Sold as-is. Cash buyers only.

Beds:
5
Baths:
5.00
Sq.Ft.:
7,462
Status:
NEW LISTING
MLS#:
5219403
Type:
Single Family
Subdivision:
Woodlands Sub
Lot size:
3 Acres
Year built:
1999
Courtesy: Keller Williams Greater Metropolitan 216-839-5500
View additional info

ADDITIONAL INFORMATION

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!

Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
5217370
Type:
Single Family
Subdivision:
Sherwood Trail
Lot size:
5.05 Acres
Year built:
1995
Courtesy: Keller Williams Greater Metropolitan 216-839-5500
View additional info

ADDITIONAL INFORMATION

Tucked away on a quiet, picturesque cul-de-sac and set back along a stunning tree-lined drive, this rare Chesterland estate offers the ultimate in privacy, serenity, and natural beauty. Nestled on a lush, wooded 5-acre parcel bordering a sprawling 58-acre farm, this expansive 3,649 sq ft home delivers an unmatched sense of seclusion. Inside, four generously sized bedrooms, all appointed with a bath, offer space and character, including a first-floor primary suite with soaring vaulted ceilings. The crown jewel is the magnificent sunroom, wrapped on three sides by expansive windows and crowned with skylights that flood the space with natural light year-round. A three-car garage completes this exceptional package. Properties where wooded acreage, stately bedrooms, and stunning sunsets converge rarely become available. This is more than a home. It's a lifestyle.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,724
Status:
Active
MLS#:
5214401
Type:
Single Family
Subdivision:
Willow Hill Estates
Lot size:
1.53 Acres
Year built:
1968
Courtesy: Engel & Völkers Distinct 440-568-0400
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ADDITIONAL INFORMATION

Spacious split-level home located on a quiet cul-de-sac in Chesterland, in the West Geauga School District, set on over 1.53 parklike acres w/ city sewer, mature trees, wooded views, and an exceptional backyard designed for everyday enjoyment and entertaining. A spacious 2-level stamped concrete patio with hot tub overlooks the expansive yard and is complemented by 2 storage sheds, a wood playset, attached side-entry 2-car garage, and oversized parking pad. Offering 4 bedrooms, 2.5 baths & 2,724 sq ft, the interior features generous living spaces and a functional layout. A spacious living room is filled with natural light from a large picture window and flows into a formal dining room. An eat-in kitchen includes all appliances, a dinette area, and sliding door access to the patio, making indoor-outdoor living effortless. Just steps away, a cozy family room is anchored by a fireplace and provides the perfect gathering space. The primary bedroom features a walk-in closet and private en-suite bath, while one additional bedroom also includes a walk-in closet. A large utility room offers laundry facilities and flexible space for a home office, hobby room, fitness area, or additional storage. RECENT UPDATES include: Replaced refrigerator (2024), dishwasher & washer (2023), microwave (2024), water pressure tank (2022), garage door (2026), whole house electrical box (2021), installed stamped concrete patio & concrete driveway w/ extra parking pad (2018), updated family room (2024), laundry room & mud room (2023) & half bath (2024), replaced flooring throughout 1st level (2024), installed playset (2021), shed (2022), hot tub (2021), replaced all closet doors (2026), mailbox (2026) & much more! INCLUDED are ALL kitchen appliances, washer/dryer, hot tub, playset, basketball hoop, riding mower, snow blower, portable generator, all window treatments & a 1-year home warranty. Conveniently located near OH-306, schools, shopping, restaurants, parks & other local attractions.

Beds:
5
Baths:
5.00
Sq.Ft.:
7,266
Status:
Active
MLS#:
5215468
Type:
Single Family
Lot size:
5.31 Acres
Year built:
1971
Courtesy: McDowell Homes Real Estate Services 440-205-2000
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,376
Status:
Active
MLS#:
5214799
Type:
Single Family
Lot size:
9.42 Acres
Year built:
1972
Courtesy: Engel & Völkers Distinct 440-568-0400
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ADDITIONAL INFORMATION

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.

Beds:
2
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
5213463
Type:
Single Family
Subdivision:
Maywood Community
Year built:
1984
Courtesy: Keller Williams Living 440-318-1620
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ADDITIONAL INFORMATION

Looking to downsize or lower costs…this spacious 2 bed/2 bath well-maintained manufactured home in the much sought after 55+ Maywood Community is a great alternative to renting. Privacy yet affordable living in this lovely home with bump-out great room, large screened covered porch, and a dog kennel on a corner lot. Newly renovated spacious kitchen with new cupboards, granite countertop, new appliances, with breakfast bar and new vinyl flooring throughout. Open concept kitchen, living room and dining area feature vaulted ceilings and fan. Master bedroom features large walk-in closet. Great floorplan puts the second bedroom at opposite end of the unit, providing additional privacy and a second full bath. Screened porch adds more living space. Side yard is fenced for a dog kennel and a storage shed. Roof and storm windows 10 yrs. old. Furnace 4yrs, Dryer & Hot water tank 9 yrs, AC ?, and brand new washer. Residents praise the quiet, semi-rural setting, beautiful wooded lots, and low Geauga County taxes. It is widely viewed as a peaceful, well-maintained place for active adults. Application and $50 fee must be submitted and approved by Maywood Community. Average gas bill $75/mo. and electric $65/mo. Monthly land rental fee covers water & sewer, trash and snow removal.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,252
Status:
Active
MLS#:
5212177
Type:
Single Family
Subdivision:
Buckingham Square Estate
Lot size:
3.05 Acres
Year built:
1976
Courtesy: Keller Williams Greater Metropolitan 216-839-5500
View additional info

ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,731
Status:
Active
MLS#:
5209046
Type:
Single Family
Subdivision:
County Line Estates
Lot size:
1.3 Acres
Year built:
1960
Courtesy: Redfin Real Estate Corporation 216-586-3067
View additional info

ADDITIONAL INFORMATION

Welcome to 12808 Wellswood Trail in Chesterland, where peaceful country living meets everyday convenience. This beautifully maintained 3-bedroom, 2.5-bath California ranch offers true one-floor living on nearly 1.5 acres of lovingly landscaped property designed to feel like your own private nature retreat. Surrounded by mature trees for privacy, vibrant perennials, and a charming garden area, the outdoor space is perfect for relaxing mornings or entertaining evenings on the spacious patio. Inside, high ceilings and abundant natural light create a bright and airy atmosphere throughout the home.The inviting family room features a cozy wood-burning stove, making it the perfect place to gather during Ohio’s cooler months. The tastefully updated kitchen blends style and function, offering a welcoming space for cooking and entertaining. All three bedrooms are generously sized and provide ample closet space, while a versatile flex room off the dining area offers endless possibilities—ideal as a music room, craft room, library, playroom, or home office. Located just minutes from shopping, restaurants, and freeway access, this home delivers the best of both worlds: serene country living close to the city—without the burden of city taxes. BRAND NEW SEPTIC SYSTEM and ELECTRIC PANEL giving buyers added confidence and peace of mind by eliminating unexpected surprises. Sellers have installed an electric car charger in their garage. The septic company will level the dirt from the installation after it settles. This is a rare opportunity to own a private retreat in the heart of Chesterland—where comfort, nature, and convenience come together beautifully.

Beds:
3
Baths:
2.00
Sq.Ft.:
3,018
Status:
Active
MLS#:
5204455
Type:
Single Family
Subdivision:
Carmichael
Lot size:
1.03 Acres
Year built:
1975
Courtesy: Berkshire Hathaway HomeServices Professional Realty 440-296-5006
View additional info

ADDITIONAL INFORMATION

Meticulously Maintained Four-Level Split with Custom Addition on a One-Acre Lot! Updated 3-bedroom, 2-bath home combining privacy and convenience. Multi-level decks, screened porch, babbling brook, and wooded views! Interior highlights include fresh paint, LVT, ceramic, and carpet flooring, beautiful granite countertops, updated baths with full ceramic tile shower, and a new sliding glass door. The impressive home theater room offers 368 additional square footage and features African slate, solid maple floors, and a cozy fireplace! Major updates include a new well pump system (2022) and a newer central air unit (2021). Home also features a whole-house natural gas generator and boiler heat with central air, offering the best of both worlds! Ample storage with a large basement, oversized garage with storage above, and an invisible fence surrounding the property. Prime location with short distance to schools and library, with easy access to town and freeway. Truly move-in ready!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,250
Status:
Active
MLS#:
5201698
Type:
Single Family
Lot size:
3.72 Acres
Year built:
1950
Courtesy: CC Sells Homes, LLC. 440-942-0633
View additional info

ADDITIONAL INFORMATION

Nestled in the woods in Munson Township, is a spacious log cabin home, with 4 bedrooms and 2 and a half baths. This home sits on 3.72 acres of picturesque land with views of the woods, ravine, rock piles, and more. Nature truly does surround you here. The wormy chestnut walls and ceilings in the living room and kitchen give this home so much warmth and country charm. The two stone fireplaces, one in the family room (with a blower) and one in the living room, were hand built from rocks found on the wooded grounds. The primary bedroom plus two more are on the main level. There are two full baths plus a half bath on the main level also. Up the staircase with a hand carved railing, you will find the 4th bedroom, and also a great big attic for storage. There is a large dine in kitchen too. Just look out the large picture window in the kitchen and enjoy the views of the lush woods, as birds and woodland animals play. An enclosed porch is right off the living room in the rear of the house which also offers fabulous views. There is a two car attached garage, that leads into the laundry room/mud room. There is a shed or small cabin on the property that could serve many purposes. In 2025 a new roof was put on, along with some gutters, and also a new hot water tank. Come see this truly unique home, and enjoy peaceful country living.

Beds:
2
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
5182057
Type:
Single Family
Lot size:
0.92 Acres
Year built:
1948
Courtesy: Real of Ohio 855-450-0442
View additional info

ADDITIONAL INFORMATION

Move right in to this beautifully completely remodeled home set on nearly an acre in the heart of Chesterland! This turnkey property has been thoughtfully updated from top to bottom and is truly ready for immediate occupancy. Step inside to discover a brand-new kitchen featuring all-new cabinetry, quartz countertops, and a spacious layout with a comfortable eating area that opens seamlessly to the living room—perfect for everyday living and entertaining alike. The entire home showcases brand-new luxury vinyl plank (LVT) flooring and has been freshly painted throughout, offering a clean, modern feel. The home includes two bedrooms and a highly functional first-floor laundry room complete with an abundance of shelving and storage. Outside, enjoy the charm of a welcoming front porch, plus a backyard pergola ideal for relaxing or hosting guests. A detached garage adds convenience and additional storage. Don’t miss this opportunity to own a beautifully updated home with space, style, and comfort—schedule your showing today!

Beds:
4
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
5148756
Type:
Single Family
Subdivision:
County Line Estates
Lot size:
1.29 Acres
Year built:
1979
Courtesy: Da Vinci Fine Homes, LLC. 440-840-0663
View additional info

ADDITIONAL INFORMATION

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.

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Andrea D. Conner, License BRKP.2017002935, Xome Inc., License REC.2015001703, [email protected], 844-400-XOME (9663), 11427 Read Hartman Hwy, Suite 236, Cincinnati, OH 45241


The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Yes MLS. Real estate listings held by brokerage firms other than the owner of this site are marked with the Internet Data Exchange logo and detailed information about them includes the name of the listing broker(s). IDX information is provided exclusively 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 purchasing. Information deemed reliable but not guaranteed. Copyright © 2026 Yes MLS. All rights reserved.



Chesterland Real Estate

Chesterland is located in Ohio. Chesterland, Ohio has a population of 7,481. Chesterland is less family-centric than the surrounding county with 26.69% of the households containing married families with children. The county average for households married with children is 34.64%.

The median household income in Chesterland, Ohio is $87,050. The median household income for the surrounding county is $90,285 compared to the national median of $69,021. The median age of people living in Chesterland is 52.3 years.

Chesterland Weather

The average high temperature in July is 80.7 degrees, with an average low temperature in January of 16.4 degrees. The average rainfall is approximately 45.6 inches per year, with 78 inches of snow per year.

Chesterland Map

Chesterland Real Estate Market Conditions

  • Median sales price

    $408,750
    13.4%
    change since last quarter
  • # Active listings

    14
    30-day change

Chesterland Schools and Demographics

Education near Chesterland, OH

City County
High School Graduates 91.41 90.59
College Degree - 2 year 7.41 7.31
College Degree - 4 year 35.64 38.42
Graduate Degree 6.62 9.71
Expenditures per Student 15,619 15,619
Students per Teacher 18.2 18.2

Elementary Schools near Chesterland, OH

Grades Students P/T Ratio ZIP
Edison Elementary School KG - 05 753 21 44094
Gates Mills Elementary School KG - 05 114 17 44040
Grant Elementary School KG - 05 679 18.4 44094
Kirtland Elementary School PK - 05 518 15.2 44094
Newbury Elementary School KG - 05 164 12.6 44065
Robert C Lindsey Elementary School PK - 05 336 20.1 44026
Westwood Elementary School KG - 05 413 19.4 44072

Middle Schools near Chesterland, OH

Grades Students P/T Ratio ZIP
Kirtland Middle School 06 - 08 307 13.6 44094
West Geauga Middle School 06 - 08 486 19.4 44026
Willoughby Middle School 06 - 08 780 16.2 44094

High Schools near Chesterland, OH

Grades Students P/T Ratio ZIP
Kirtland High School 09 - 12 360 13.5 44094
Newbury High School 06 - 12 292 12.5 44065
South High School 09 - 12 1,312 21.2 44094
West Geauga High School 09 - 12 781 19.3 44026

Ungraded Schools near Chesterland, OH

Grades Students P/T Ratio ZIP
School of Innovation UG - UG 0 44094

Demographics near Chesterland, OH

City County
Neighborhood Type Suburban
Population 7,481 95,408
Population Density 1,709 238
Median Age 52.3 44.6
People per Household 2.5 2.7
Median Household Income 87,050 90,285
Average Income per Capita 39,718 45,199

Real estate near Chesterland