Chesterland OH Real Estate & Homes for Sale

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Beds:
5
Baths:
5.00
Sq.Ft.:
2,974
Status:
NEW LISTING
MLS#:
5173779
Type:
Single Family
Subdivision:
County Line Estates #2
Lot size:
2.03 Acres
Year built:
1959
Courtesy: Berkshire Hathaway HomeServices Professional Realty 440-781-2455
View additional info

ADDITIONAL INFORMATION

This flexible 4-5 bedroom Chesterland colonial is designed to grow and shift with you. it’s perfect for multigenerational living, blended families, or anyone craving a home that adapts as life evolves. Step into a living room where a gas fireplace wrapped in custom built-ins sets the tone for holiday moments, slow mornings, and the calm rhythm of daily life. The kitchen offers generous storage & prep space with an eat in nook. The formal dining room flows into a dreamy screened-in porch—an indoor/outdoor hideaway for coffee, cocktails, or late-summer dinners. Just beyond, the fenced patio opens to a wide, open lawn that feels like your own private park. A heated in-ground pool—freshly painted in ’24 and enhanced with new handrails and a bar—anchors the backyard, inviting pool parties, neighborhood chili cook-offs, or a sunset float. What makes this property especially rare is the flexibility of the floorplan: a true first-floor primary suite option with an ADA-compliant full bath and walk-in closet added in ’23, perfect for aging parents or anyone who wants main-floor living. Or, use the same area as a spacious family room with a picture window framing the pool and wooded backyard. Upstairs, 4 bedrooms and 3 full baths offer everyone their own retreat, including TWO large ensuite bedrooms with modern bathrooms and 2 additional bedrooms served by another full bath. The lower level—freshly waterproofed in ’25—provides excellent storage and a second laundry area. Throughout the home, the updates tell a story of thoughtful care: 200-amp electrical service (’23), whole-house Generac setup (’24), driveway sealing and coating (’25), new sulfur guard and pressure tank (’24), new front deck and ramp (’24), and responsible tree removal (’25). Set on a beloved street just east of Gates Mills and within top-ranked West Geauga Schools, the home is as practical as it is soulful—ready for the next chapter, the next generation, and every version of “family” you bring with you.

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
5172341
Type:
Single Family
Subdivision:
County Line Estates
Lot size:
1.84 Acres
Year built:
1955
Courtesy: Wittensoldner Realty 330-324-9371
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ADDITIONAL INFORMATION

This ranch has beautiful views with large windows and an open floor design for entertaining. The large kitchen was just remodeled 5 yrs ago. Come in from the outside thru a breezeway to take off your shoes and have easy access to the half bath. Off of the living room which has a fireplace, is a 18 X22 deck for grilling and relaxing. The 3 bedrooms and full bath are down the hall for complete privacy. Go downstairs to a walk out basement with a huge family and another fireplace. You will also find another full bath and a large laundry area with plenty of countertop and cabinets. Outside you have almost 2 acres to enjoy and family picnics.

Beds:
4
Baths:
2.00
Sq.Ft.:
3,015
Status:
Active
MLS#:
5172109
Type:
Single Family
Subdivision:
Township/Chester Tract 2
Lot size:
5.47 Acres
Year built:
1973
Courtesy: RE/MAX Revealty 440-247-3707
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ADDITIONAL INFORMATION

Exquisite log home on 5 serene acres nestled in the heart of Chesterland, OH. This stunning home exudes rustic elegance and timeless craftsmanship that offers a peaceful retreat with endless possibilities for outdoor living, equestrian pursuits, or simply enjoying nature's beauty. This meticulously crafted log home has 4 bedrooms, 2 baths, plus possible 1st floor bedroom. It boasts custom details throughout - hardwood floors, exposed beams, warm wood finishes, 2 wood burning stoves, and an inviting open floor plan that blends luxury with cozy charm. There are over 1,200 sq ft of unfinished walkout basement to create additional living space or recreation room. Detached 3 car garage with matching log construction of the home provides ample storage for vehicles, equipment, or hobbies/workshop. This property includes a beautiful 2-stall horse barn perfect for 4H and equestrian enthusiasts, featuring sturdy construction, a stall sized tack room and large hayloft, with potential for expansion. It has rolling hills, mature trees, and an open pasture that creates a picturesque, park-like setting, plus it abuts Sunnybrook Preserve providing gorgeous walking trails just a step away. The location has many local parks for close access to riding trails. This one-of-a-kind property combines many unique features with a secluded, serene location that is just minutes from local amenities. Whether you're seeking a family estate, hobby farm, or peaceful escape, this is a rare gem waiting to be called home!

Beds:
4
Baths:
3.00
Sq.Ft.:
3,371
Status:
Active
MLS#:
5170279
Type:
Single Family
Lot size:
5.39 Acres
Year built:
1990
Courtesy: Keller Williams Greater Cleveland Northeast 440-255-5500
View additional info

ADDITIONAL INFORMATION

LOCATION LOCATION LOCATION! Welcome to your charming, rustic retreat in sought after Chesterland - on a private Culdesac street - Did I mention 5+ acres! This home features 4 bedrooms, 3 baths, The Large foyer entrance leads you into the Massive vaulted Great room with soaring wood-burning fireplace! The fully remodeled kitchen with island, gas range and 2 dishwashers for all those entertaining/holiday dinners! Plenty of counter space and cabinets for the gourmet cook. Check out that natural wood hood sitting over your chef's range. Pantry and coffee/cocktail station are also in the heart of the home. Kitchen also has a door that leads to the deck for summer barbecues. 1st floor bedroom with a 1st floor full bath is great for guests or can be used as an office. 3 car attached garage entry with space for all your coats, boots and backpacks. Heading up stairs you will find a generous Primary suite with a beautifully remodeled master bath and cedar closets. 2 additional bedrooms and another full bath along with a Library nook, laundry and walk out upper decks round out the upstairs! Lower level features finished recreation room with a Napoleon vented cast iron gas stove, and plenty of storage. Updates include*hot water tank* AC * whole house generator*whole house humidifier* All new kinetico water softener system* basement has been previously waterproofed * Massive 3+ car detached garage/barn added along with Network cable - 100 AMP power - and Natural gas. This garage is truly a mechanic's/car junkie/ toy collector's dream and has enough space for a car lift on one end. Enjoy this country setting just minutes from freeway access, shopping, and Patterson Fruit Farm! Come see it and fall in love!

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
5170800
Type:
Single Family
Subdivision:
Lynn Sub
Lot size:
1 Acres
Year built:
1961
Courtesy: Beth Rose Real Estate and Auctions, LLC 419-534-6223
View additional info

ADDITIONAL INFORMATION

This is an ONLINE ONLY foreclosure sale. There are NO SHOWINGS. Deposit due by wire transfer within 48 upon conclusion . Cash deal; funding must take place within 30 days of confirmation of sale. 5% Buyer’s Premium shall apply. Subject to postponement and cancellation. Full terms and conditions at online registration.

Beds:
5
Baths:
5.00
Sq.Ft.:
5,560
Status:
Active
MLS#:
5168262
Type:
Single Family
Lot size:
2.91 Acres
Year built:
1965
Courtesy: Keller Williams Living 440-318-1620
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ADDITIONAL INFORMATION

Nestled on nearly 3 private acres in Munson Township, this beautifully renovated home combines peaceful country living with timeless character. Set back from the road, it features 5 bedrooms, 4.5 baths, and a fully updated carriage house apartment above the detached 3 car garage, ideal for guests, in-laws, or rental income. An inviting foyer leads to a breathtaking great room with soaring beamed ceilings and a floor to ceiling stone fireplace, surrounded by panoramic windows that showcase the spring-fed waterfalls and ponds. The main level highlights refinished hardwood oak flooring, a fully reimagined kitchen with a new layout, quartz countertops, tile backsplash, new appliances, cabinetry, and lighting, plus a home office with built-in shelving. The first-floor primary suite includes a private bath and dressing area, along with convenient first-floor laundry. Upstairs, four comfortable bedrooms share two Jack and Jill bathrooms, providing space and privacy for family or guests. Nearly every surface has been refreshed, including new roofing on both the main home and carriage house, cedar siding repairs with full exterior painting, new exterior stonework, plumbing and electrical updates, and two EV charging stations. The setting is just as impressive, with new porch posts and beams, stone patios and bridge work, updated landscaping, and a refurbished driveway surrounded by mature trees. A truly special property where natural beauty meets thoughtful renovation, just minutes from NDCL, Alpine Valley Ski Resort, Historic Fowlers Mill Golf Course, and nearby shopping and dining. Don't miss your chance, schedule a showing today!

Beds:
4
Baths:
4.00
Sq.Ft.:
3,376
Status:
Active
MLS#:
5168163
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). Included are all kitchen appliances, washer/dryer & tv mounts. Conveniently located near I-90, I-271, OH-44, restaurants, shopping & other local attractions.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,408
Status:
Active
MLS#:
5167868
Type:
Single Family
Subdivision:
Baldwin Kenealy
Lot size:
1.22 Acres
Year built:
1956
Courtesy: eAgent Real Estate Corp. 440-391-2340
View additional info

ADDITIONAL INFORMATION

Beautifully updated ranch in a quiet Geauga County setting with direct access to a scenic park across the street. Enjoy paved walking trails, a long bridge, playground, pavilion, and restrooms—all part of a hidden gem that often feels like your own private retreat. Inside, the home blends modern updates with warm, natural light and authentic hardwood floors. The open flow from the living room to the dining area and new kitchen makes entertaining effortless. The kitchen was fully remodeled in June 2024 with new cabinetry, countertops, tile backsplash, flooring, and stainless appliances. Both bathrooms were tastefully redone in 2025, complementing the home’s fresh and comfortable feel. Major system updates include a new furnace and A/C coil (Nov. 2023), pressure tank (Sept. 2023), and water softener (Oct. 2025). The exterior received extensive upgrades—new siding, soffits, and gutters (Aug. 2024), full roof replacement (Mar. 2025), and new garage door (July 2024). The chimney was rebuilt from the roof up (Nov. 2024), and the septic system was serviced (Mar. 2025) with a new UV ballast installed (Oct. 2025). Additional highlights include a bright enclosed porch overlooking the large backyard with fire pit, main-floor laundry with built-in cabinetry, and a cozy wood-burning fireplace. Truly move-in ready—offering comfort, style, and peace of mind through thoughtful updates inside and out. Agent related to seller

Beds:
3
Baths:
2.00
Sq.Ft.:
1,528
Status:
Active
MLS#:
5164711
Type:
Single Family
Subdivision:
Chesterland Hills
Lot size:
1.28 Acres
Year built:
1959
Courtesy: Keller Williams Living 440-318-1620
View additional info

ADDITIONAL INFORMATION

Beautifully renovated 3 bedroom, 1.5 bath Ranch offering just over 1,500 sq ft. of stylish, comfortable living space on a serene 1.28 acre lot. Every detail has been thoughtfully updated- this home is truly move in ready! This home has been fully updated from top to bottom- new roof, HVAC, baths, flooring, doors, paint, fixtures, and more. Bright, open layout with spacious living and a brand new kitchen featuring modern finishes, all new cabinetry, granite countertops, and stainless steel appliances. In addition to the current owner's full renovation, there have been major system updates (taken care of by previous owner) with a full electrical rewire, replaced ductwork, and replaced well and septic system. That means peace of mind for years to come! This stunning ranch combines modern updates with worry-free living--all that's left to do is move in and make it your own. Schedule your showing today!

Beds:
3
Baths:
2.00
Sq.Ft.:
3,018
Status:
Active
MLS#:
5163622
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.:
2,876
Status:
Active
MLS#:
5165273
Type:
Single Family
Lot size:
2.17 Acres
Year built:
1973
Courtesy: RE/MAX Results 440-354-3334
View additional info

ADDITIONAL INFORMATION

Welcome to this 4 bedroom colonial situated on a wooded lot with a lake in the backyard. Hardwood floors throughout the eat-in kitchen & formal Dining Room. Large remodeled kitchen has lots of counter space, a breakfast bar, all stainless appliances and an eating area with views of the lake out back. The main floor features 4th bedroom or office space, Family room with French doors to the patio. The laundry area is located in a closet in the kitchen for convenience, but can be relocated back to the basement (hook ups are there). Fresh neutral paint throughout. Second floor features large master bedroom w/ walk-in closet and an ensuite bath. Tandem bedroom with 2 spacious areas as well as full bath upstairs. In the lower level, there is lots of storage space & a recreation room. Roof tear-off 2019, all windows 2010, leafguard on all gutters, super efficient Geothermal heating and cooling, serviced and hwt replaced in August, artesian well, & septic was serviced in June. Little over 2 acres but feels larger with shared beautiful large natural pond, a trail for walks, 3 years of a rustic permaculture garden that was so fruitful & Apple trees!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,288
Status:
Active
MLS#:
5163386
Type:
Single Family
Subdivision:
Manchester Farms
Lot size:
1 Acres
Year built:
1955
Courtesy: Keller Williams Chervenic Rlty 330-686-1644
View additional info

ADDITIONAL INFORMATION

Endless potential with this gutted ranch home set on a spacious 1-acre lot with a barn and shed. Whether you're looking to create your dream home or invest in a promising property, this blank slate offers a solid foundation and plenty of room to grow. Surrounded by trees and open space, enjoy the peace of country living with the convenience of nearby amenities on the main road. Bring your vision and make it your own!

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
5163277
Type:
Single Family
Lot size:
3.16 Acres
Year built:
1947
Courtesy: RealtyNet, Inc. 440-729-5500
View additional info

ADDITIONAL INFORMATION

Great opportunity to own a 3 bedroom, 2 1/2 bath Ranch with walk-out basement on 3.16 acres / Enter this well maintained home through the Living Rm with FP and adjoining formal Dining Rm / Plenty of kitchen cabinets and counter space with all appliances included / Family Rm shares space with the Breakfast Rm exiting through sliding doors to a large Enclosed Patio / Basement is partially above grade with finished Rec Rm area and walk-out's to side and rear of home / Unfinished area of basement includes a Laundry Rm and Workshop / Hot water boiler / Long asphalt driveway approach off Caves Rd with turn-around at garage with second exit on to Cedar Rd / Large garage with lower level for storage and second floor Workshop with lots of glass to brighten your project space / Tennis court needs maintenance / Whole house generator

Beds:
5
Baths:
3.00
Sq.Ft.:
3,375
Status:
Active
MLS#:
5148365
Type:
Single Family
Subdivision:
Africa Acres
Lot size:
17.5 Acres
Year built:
1901
Courtesy: Berkshire Hathaway HomeServices Professional Realty 440-266-8085
View additional info

ADDITIONAL INFORMATION

This is truly a one of a kind property situated at the end of a semi private lane surrounded by 17.5 acres of scenic privacy, pastures, woods and streams! With many recent upgrades, this home is the perfect blend of classic charm and tradition with today’s modern amenities. Enter the impressive living room with hardwood flooring and trussed cathedral ceilings. The large wood burning fireplace is accented with a mantle dating to the late 1700's and the large windows allow an abundance of natural light. The formal dining room continues with hardwood flooring and a bay window, perfect for entertaining family and friends. The chef in the family will delight in the well equipped chef's kitchen with newer top of the line "Cafe" appliances, a center island breakfast bar and another cozy fireplace. Offering nonstop views of the property, the spacious family room has brick flooring, another wood burning fireplace and spectacular mantle, newer windows and a door to the back patio. The primary suite is tucked away for privacy on the first floor with hardwood flooring, private bath, another bay window and Dutch door to the patio. Another bedroom is found at this end of the home, which would be ideal for a home office or study. The first floor has another secluded bedroom and bathroom off the kitchen and the laundry is found there as well. The second level of the cape cod style house has two bedrooms and a third full bath. Outside, there are two patios, a four stall horse barn with two fenced pastures and a rustic "playhouse". New roof among other fantastic improvements! Welcome Home!

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.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,470
Status:
Active
MLS#:
5134926
Type:
Single Family
Subdivision:
Chesterland Hills Sub Tr 3
Lot size:
1.71 Acres
Year built:
1975
Courtesy: Ohio Broker Direct 614-989-7215
View additional info

ADDITIONAL INFORMATION

Welcome to your dream home in the heart of Chesterland! Nestled on a serene 1.71-acre lot, this completely renovated 4-bedroom, 3-bath beauty offers 2,470 sq ft of luxurious living with modern finishes and timeless charm. Step inside to discover a bright, open layout with new LVP flooring throughout, recessed lighting and three cozy fireplaces that create warmth and character in every corner. The sunroom with a fireplace and wall of windows is the perfect retreat for all seasons. The heart of the home - a stunning chef's kitchen - boasts porcelain tile flooring, a large quartz island, quartz countertops, shaker-style soft-close cabinets, and brand-new stainless steel appliances, including a washer and dryer. All three full bathrooms have been tastefully remodeled in 2025, featuring elegant walk-in showers and high-end finishes. You'll also appreciate the new roof, new windows, new interior & exterior paint, and brand-new sidewalk - all completed in 2025. The spacious, insulated 4-car attached garage provides comfort and convenience year-round, and the two separate living areas offer plenty of space for both entertaining and everyday living. With a newer furnace and AC, all the major updates are complete including newly upgraded septic in accordance with code, just move in and enjoy peaceful living on a quiet, tree-lined street with easy access to amenities, top-rated West Geauga School District, and parks. Don't miss this one-of-a-kind opportunity to live in a turnkey home on a picturesque lot in Geauga County!

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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 © 2025 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

    $380,000
    13.4%
    change since last quarter
  • # Active listings

    17
    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