Chesterland OH Real Estate & Homes for Sale

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Open House:

Saturday, 7/18

More Open House Info >

Beds:
4
Baths:
5.00
Sq.Ft.:
3,350
Status:
NEW LISTING
MLS#:
5225746
Type:
Single Family
Lot size:
1.74 Acres
Year built:
1988
Courtesy: Redfin Real Estate Corporation 216-586-3067
View additional info

ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
3.00
Sq.Ft.:
3,022
Status:
NEW LISTING
MLS#:
5226022
Type:
Single Family
Subdivision:
Battles Sub
Lot size:
5.26 Acres
Year built:
1986
Courtesy: Keller Williams Greater Metropolitan 216-839-5500
View additional info

ADDITIONAL INFORMATION

Set on 5 sprawling acres, this beautifully remodeled home offers the perfect blend of privacy and move-in-ready comfort. Remodeled throughout, the interior showcases fresh, updated finishes from top to bottom. Cambria quartz countertops, KitchenAid double oven, master closet with custom built-ins, and Stainmaster carpets throughout are just some of the luxurious improvements. Enjoy peace of mind with a new furnace and HVAC system, both installed in 2022. Step outside to a spacious wood deck off the back of the home, perfect for morning coffee, grilling, or simply soaking in the peaceful, wooded views. The partially finished walk-out basement offers effortless access to the expansive grounds, ideal for entertaining, hobbies, or future expansion. Two additional sheds provide excellent storage or workshop space for tools, equipment, or hobbies. A rare opportunity to own acreage with all the major updates already done. Don't miss this one!

Beds:
4
Baths:
3.00
Sq.Ft.:
1,638
Status:
Active
MLS#:
5224421
Type:
Single Family
Subdivision:
Chester Estates 02
Lot size:
1.33 Acres
Year built:
1958
Courtesy: RE/MAX Crossroads Properties 440-331-2870
View additional info

ADDITIONAL INFORMATION

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.

Beds:
6
Baths:
5.00
Sq.Ft.:
5,560
Status:
Active
MLS#:
5224281
Type:
Single Family
Lot size:
2.91 Acres
Year built:
1965
Courtesy: HomeSmart Real Estate Momentum LLC 440-578-8058
View additional info

ADDITIONAL INFORMATION

Set on approximately 3 private acres in Munson Township, within the sought-after Chardon Local School District, this beautifully updated home offers peaceful surroundings, thoughtful renovations, and exceptional flexibility. Tucked back from the road and surrounded by mature trees, the property features ponds, cascading waterfalls, and inviting outdoor living spaces. The main residence includes 5 bedrooms and 4.5 baths, plus a detached 3-car garage with a renovated carriage house apartment above - ideal for guests, extended family, a home office, or possible rental income. A welcoming foyer opens to a dramatic great room with soaring exposed-beam ceilings, panoramic windows, and a floor-to-ceiling stone fireplace. The updated interior includes refinished oak hardwood floors and a redesigned kitchen with quartz countertops, new cabinetry, tile backsplash, updated lighting, and new appliances. A home office with built-in shelving adds convenience for work or study. The first-floor primary suite includes a private bath, dressing area, and nearby first-floor laundry. Upstairs, 4 additional bedrooms include an en suite bedroom with private bath, plus an additional full hall bath, providing comfortable space and privacy. Recent improvements include newer roofs on main home and carriage house, cedar-siding repairs, exterior paint, updated stonework, plumbing and electrical improvements, updated HVAC in 2026, 2 EV charging stations, refreshed porch posts and beams, stone patios and bridgework, updated landscaping, and a refurbished driveway. Conveniently located near NDCL, Alpine Valley, Fowler's Mill Golf Course, shopping, dining, and recreation, this distinctive property offers the best of natural beauty, privacy, and modern updates. Schedule your private showing today.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,444
Status:
Active
MLS#:
5223343
Type:
Single Family
Subdivision:
Munson 03
Lot size:
2 Acres
Year built:
1958
Courtesy: HomeSmart Real Estate Momentum LLC 440-578-8058
View additional info

ADDITIONAL INFORMATION

Opportunity awaits with this spacious 4-bedroom, possible 5-bedroom ranch situated on 2 beautiful acres! Offering 2 full bathrooms and a finished attic space that could serve as an additional bedroom, office, or bonus room, this home has plenty of room to grow. New Roof and Gutters 2024. Outside, you'll find a HUGE barn/garage with a second story, providing endless possibilities for storage, hobbies, a workshop, or future expansion. All appliances stay, making this property an even better value. With a little vision and some TLC, this property could truly shine. Don't miss your chance to transform this hidden gem into your dream home!

Beds:
4
Baths:
4.00
Sq.Ft.:
3,373
Status:
Active
MLS#:
5222240
Type:
Single Family
Subdivision:
Chester 02
Lot size:
3.61 Acres
Year built:
1989
Courtesy: HomeSmart Real Estate Momentum LLC 440-578-8058
View additional info

ADDITIONAL INFORMATION

Secluded 4 bedroom 3 ½ bath colonial located at the end of the cul-de-sac in sought after Chesterland that sits on 3.5 wooded acres. This home has over 3,300 sq ft and boasts a grand 27 x 16 eat in kitchen with granite counters, center island/breakfast bar with seating for 3, appliances that stay and a ton of cabinets that will meet all your kitchen storage needs, a very large pantry and then some and a spacious dining area with a bay window. A great kitchen for friends and family to gather. The large great room features a brick gas fireplace, crown molding and recessed can lighting, the dining room is big enough to accommodate a large table for those holiday dinners. There is a first floor bedroom and full bath with a walk-in shower that could potentially be an in-law suite or a first floor office. A first floor laundry room/mud room cabinets, utility sink and stall shower, another half bath and a 3 season room that complete the main floor. The second floor includes the HUGE master suite with 2 walk-in closets, linen closet, a glamour jetted bathtub, large walk-in shower, a full wall double vanity, and ceramic flooring. There are 2 extra large bedrooms and another full bath that complete the second floor. The lower level has a partially finished basement and two concrete floored crawl spaces. Amenities include: 3 car attached garage, whole house generator, newer A/C and hot water tank, water treatment system, large backyard, deck, front/wrap around porch, ADT security system, outdoor shed, lots of storage throughout the house and West Geauga Schools.

Open House:

Saturday, 7/18

More Open House Info >

Beds:
5
Baths:
5.00
Sq.Ft.:
7,462
Status:
Active
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:
5
Baths:
5.00
Sq.Ft.:
4,866
Status:
Active
MLS#:
5215468
Type:
Single Family
Lot size:
5.31 Acres
Year built:
1971
Courtesy: McDowell Homes Real Estate Services 440-205-2000
View additional info

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.

Open House:

Sunday, 7/19

More Open House Info >

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
View additional info

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. $600 Monthly land rental fee covers water & sewer, trash and snow removal.

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:
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

    $460,000
    13.4%
    change since last quarter
  • # Active listings

    12
    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