7775 Woodlands Trail

Chesterland, OH
$ 995,000 Beds 5 Baths 4.5 Sq 5,158
Monthly Estimate* How much can I afford?

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!

Active

  • Price
  • $ 995,000
  • City
  • Chesterland
  • Bedrooms
  • 5
  • Full Bathrooms
  • 4
  • County
  • Geauga
  • Half Bathrooms
  • 1
  • Area
  • Lot Size
  • 3 Acres
  • Zip
  • 44026
  • Sqr Footage
  • 5,158
  • Year Built
  • 1999
  • Taxes
  • $ 11991
  • Style
  • MLS#
  • 5219403
Listed By: Keller Williams Greater Metropolitan
Data Source: MLSNow

Features

General

Sewer Septic Tank
Heating Forced Air,Gas
Cooling Central Air
Possession Negotiable
Roof Asphalt,Shingle
Garage Spaces 5
Patio/Porch Features Patio,Porch
Architectural Style Colonial,Conventional
Construction Materials Stone,Vinyl Siding
Year Built 1999
Stories Count 2
Township Chester Twp
Levels Two
Property Subtype Single Family Residence
Tax Year 2025
County Geauga
Property Type Residential
HOA false
Attached Garage true
Subdivision Name Woodlands Sub
Garage Y/N true
Total Rooms 9
Full Baths 4
Status Active
Directions Head north on Caves Rd toward Woodlands Trail, Turn left onto Woodlands Trail
ModificationTimestamp 2026-08-19T18:06:59.070-00:00
City Chesterland
High School District West Geauga LSD - 2807
Lot Size Units Acres
Carport Y/N false
Land Lease Y/N false
Tax Annual Amount 11991
Home Warranty Y/N false
Living Area Units Square Feet
Standard Status Active
Middle/Junior School District West Geauga LSD - 2807
Elementary School District West Geauga LSD - 2807
Year Built Source Public Records
Property Sub Type Additional Single Family Residence
PostalCity CHESTERLAND
Legal Description S/L 4 WOODLANDS SUB

Interior Features

Interior Amenities Wet Bar,Built-in Features,Eat-in Kitchen,Granite Counters,High Ceilings,Kitchen Island
Basement Full,Partially Finished,Walk-Out Access
Total Fireplaces 2
Fireplace Features Family Room,Living Room
Basement (Y/N) true
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N true
Above Grade Finished Area 5158
Half Baths 1
Total Bedrooms 5
Below Grade Finished Area 2304
Main Level Bathrooms 1
Below Grade Finished Area Source Estimated
Above Grade Finished Area Source Assessor
Total Baths 5

Exterior Features

Fencing None
Parking Features Attached,Detached,Garage
Lot Features Wooded
Water Source Well
Lot Size Area 3
Lot Size Acres 3
Lot Size Source Assessor
Waterfront Y/N false

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Youngstown, OH office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
Adjust Payment Options
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Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Unknown Elementary School
Middle School Unknown Middle School
High School Unknown High School

Price History

6/19/2026 Listed $995,000

Property vs Zip Code Average in 44026

Price
AVG $590K
$1,000K
Taxes
AVG $8,088
$11,991
Year Built
AVG 1975
1999

Areas That We Cover

7775 Woodlands Trail Chesterland, OH is a Single Family Home for sale at $995000 with 5158 sqft and a lot size of 3 Acres Acre(s). 7775 Woodlands Trail Chesterland has 5 bedrooms, 4 baths and was built in 1999. The property's zip code is 44026 which is in Chesterland, OH

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided 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.

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Marie Houston

Marie Houston

330-286-7585

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