100 Chesswood Trail

100 Chesswood Trail
100 Chesswood Trail
100 Chesswood Trail
+47
6+2
 bed
6
 bath
21
 parking
3500 - 5000
 sqft
Detached
$2,499,000
For Sale
2 hours
 on site
$2,499,000
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Size
-
Lot size
3.90 Acres
Street frontage
-
Possession
Flexible
Price per sqft
$500 - $714
Taxes
$18,000 (2025)
Parking Type
-
Style
2-Storey
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Description
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.
Broker: Royal Lepage Real Estate Associates
MLS®#: X12799512
Property details
Parking:
21
Parking type:
-
Property type:
Detached
Heating type:
Heat Pump
Style:
2-Storey
MLS Size:
3500-5000 sqft
Lot front:
181 Ft
Lot depth:
938 Ft
Listed on:
Feb 18, 2026
Show all details
Rooms
LevelNameSizeFeatures
Second
Bedroom
10.8 x 13.2 ft
Second
Primary Bedroom
19.1 x 17.4 ft
Main
Family Room
15.3 x 12.9 ft
Show all
Instant estimate:
orto view instant estimate
$199,325
lower than listed price
i
High
$2,420,883
Mid
$2,299,675
Low
$2,204,965
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About 100 Chesswood Trail

Located at 100 Chesswood Trail, this Hamilton detached house is available for sale. 100 Chesswood Trail has an asking price of $2499000, and has been on the market since February 2026. This 3500-5000 sqft detached house has 6+2 beds and 6 bathrooms.

Nearby grocery options: Cristello's Village Market is a 10-minute drive. 100 Chesswood Trail, Flamborough is a 13-minute walk from great parks like Mountsberg Hall Park.

Getting around the area will require a vehicle, as the nearest transit stop is a Bus Stop (Brock Rd. / McLean Rd. (Aberfoyle) P&R) and is an 8-minute drive