
100 Chesswood Trail
Hamilton (Rural Flamborough), ON L8N 2Z7
- 6+2Bedrooms
- 6Bathrooms
- 3Garage
- 3500–5000Sq Ft
- $18,000Tax
- 181×938 ftLot Size
- Estimated Value:$2,223,869See Free Estimate Report

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Free Home EvaluationHow Much Is My Home Worth?Homes for Sale NearbySale & Price History for 100 Chesswood Trail, Hamilton, Rural Flamborough
| Start Date | End Date | Price | Event | MLS# |
|---|---|---|---|---|
| 2026-02-18 | 2026-06-01 | Login to See Prices | Sold | x12799512 |
| 2025-10-23 | 2026-02-04 | Login to See Prices | Terminated | x12477629 |
| 2025-10-01 | 2025-10-23 | Login to See Prices | Terminated | x12436554 |
| 2025-05-18 | 2025-10-01 | Login to See Prices | Terminated | x12156899 |
| 2025-01-23 | 2025-05-18 | Login to See Prices | Terminated | x11937565 |
| 2024-11-27 | 2025-01-13 | Login to See Prices | Terminated | x11191661 |
| 2024-05-03 | 2024-11-27 | Login to See Prices | Terminated | x8302714 |
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*Sold prices and complete sale & price history are regulated data. Under the Trust in Real Estate Services Act, 2002 (TRESA) and the rules of the Real Estate Council of Ontario (RECO), and pursuant to the Multiple Listing Service® rules of the Canadian Real Estate Association (CREA) and the Toronto Regional Real Estate Board (TRREB), this information may be shown only to registered users who have agreed to the applicable terms of use (a Virtual Office Website, or "VOW," arrangement). HOMEH Inc., Brokerage therefore provides it to signed-in members only. Creating an account is free and takes under a minute.
About 100 Chesswood Trail, Hamilton, Rural Flamborough
Summarized Description
- Custom built estate home on over 8 acres
- Breathtaking countryside views throughout the property
- Luxurious primary retreat with spa-inspired ensuite
- Fully finished walk-out basement with in-law suite potential
- 19-foot two-story foyer and grand staircase
- Geothermal heating and cooling for energy efficiency
- Convenient location with quick highway access
- Professionally landscaped grounds enhance curb appeal
Welcome to 100 Chesswood Trail, an executive custom built estate home on a quiet cul-de-sac in prestigious Chestnut Grove Estates. Set on over 8 acres with breathtaking countryside views, this spectacular home has it all. Featuring over 6,000 sq ft of finished living space with 6+2 bedrooms, 5.5 bathrooms, this home makes a stunning first impression with a 19-foot, two-story foyer, marble flooring, and grand 'Scarlett O'Hara' Staircase. The wide-plank hardwood floors lead to a bright two-storey sitting room with floor-to-ceiling windows and a stone gas fireplace. The kitchen offers granite countertops, stainless steel appliances, and an oversized island, with a breakfast area opening to the backyard deck. The main level also includes a family room, formal dining room, office, versatile bonus room (bedroom or den), and a mudroom with built-ins, including separate exterior access and access to the 3-car garage. Upstairs, five bedrooms enjoy ensuite or shared Jack-and-Jill baths, ensuring privacy and convenience for family or guests. The luxurious primary retreat features a spa-inspired 5-piece ensuite, custom walk-in closet, and private sitting area. The fully finished walk-out basement has a separate entrance, offering excellent in-law suite potential, and includes a kitchen rough-in, large recreation area, media room, two bedrooms, a 3-piece bath, gym or multi-purpose room, and ample storage. Additional highlights include geothermal heating and cooling, pot lights, rounded wall corners, 200 AMP service, professionally landscaped grounds, and patterned concrete walkways. Conveniently located 15/20 minutes to Waterdown, Burlington, Guelph, Cambridge, this home offers quick highway access and is your perfect picturesque city retreat.
Key Facts & Features
Property Costs
- Annual Property Tax Amount
- $18,000
- Land Transfer Tax Fee
- $43,975
Rental Items
- Rental Equipment
- Hot Water Heater
- Basement Type
- Full, Finished with Walk-Out
Interior Features
- Interior Extras
- Auto Garage Door Remote, Central Vacuum, Water Heater, Water Softener
- View
- Clear
- Fireplace/Stove
- Yes
- Elevator
- No
Exterior Features
- Exterior Extras
- Landscaped, Privacy, Patio, Porch
- Pool
- None
- Property Features
- Cul de Sac/Dead End, Golf, Greenbelt/Conservation, School, Place Of Worship, Park
Building
- Building Type
- Detached
- Building Style
- 2-Storey
- Approx Age
- 16-30
Construction
- Exterior Finish
- Brick, Stone
- Roof
- Asphalt Shingle
- Foundation Details
- Unknown
- Special Designation
- Unknown
Lot
- Lot Front
- 181.04 ft
- Lot Depth
- 938.08 ft
- Lot Shape
- Pie
Inclusions
- Inclusions
- Frige, Stove, Dishwasher, Washer/Dryer
Parking & Garages
- Garage Type
- Attached
- Garage Spaces
- 3
- Parking Spaces
- 18
- Total Garage And Parking Spaces
- 21
Heating & Cooling
- Heat Source
- Ground Source
- Heat Type
- Heat Pump
- Air Conditioning
- Central Air
- Water
- Well
- Sewers
- Septic
- Bedrooms
- 6 + 2
- Washrooms
- 6
- Kitchens
- 1
- Family / bonus room
- Yes
Room sizes
- Living Room—Main level
- Kitchen—Main level
- Dining Room—Main level
- Family Room—Main level
- Bedroom—Main level
- Office—Main level
- Den—Main level
- Bedroom—Second level
- Bedroom—Second level
- Bedroom—Second level
- Bedroom—Second level
- Primary Bedroom—Second level, 5 Pc Ensuite
- Den—Second level
- Laundry—Second level
- Office—Lower level, Semi Ensuite, Walk-In Closet(s)
- Bedroom—Lower level
- Office—Lower level
- Bedroom—Lower level
- Utility Room—Lower level
- Utility Room—Lower level
Washrooms
- 2-piece
- 5-piece, Second
- 4-piece, Second
- 3-piece, Lower
- Municipality
- Hamilton
- Neighbourhood
- Rural Flamborough
- Main cross streets
- Chesswood Trail & Campbellville Road
- Zoning
- A2
- Directions
- Chesswood Trail & Campbellville Road
- MLS® number
- X12799512
- Data source
- Toronto Regional Real Estate Board
- Status change
- 2026-06-01
- Listed on
- 2026-02-18
- Days on market
- 103 days
- Possession type
- Flexible
- Co-op commission
- 2.5 % + HST
- Seller
- Listed by
- Royal Lepage Real Estate Associates
Home Market Value
Current home valuation for 100 Chesswood Trail, Hamilton, Rural Flamborough, Hamilton, ON. Listed for $2,300,000
HOMEH Estimate
$2,223,869
Estimated Sales Range
$1,556,708 - $2,891,030
HOMEH Estimate for 100 Chesswood Trail, Hamilton, Rural Flamborough
Calculated with a real agent's CMA method — 45+ years of experience, codified. Not an AI guess.
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| Scenario 1 | Scenario 2 | Scenario 3 | Scenario 4 | |
|---|---|---|---|---|
−Down payment | % $ | % $ | % $ | % $ |
+CMHC insurance | $0 | $0 | $0 | $0 |
=Total mortgage | $1,840,000 | $1,725,000 | $1,610,000 | $1,495,000 |
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=Mortgage payment | $8,984monthly | $8,422monthly | $7,861monthly | $7,299monthly |
Land Transfer Tax
$43,975
$43,975
Around this home
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