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100 Chesswood Trail — Detached

Sold

Hamilton, ON L8N 2Z7

8 Bed · 6 Bath · Detached

MLS #X12799512

$2,110,000

Sold on July 13, 2026

July 13, 2026

Originally listed at $2,300,000 102 days on market

About This Property

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.

Property Details

Bedrooms

8

Bathrooms

6

Square Feet

3500-5000 sqft

Property Type

Detached

Style2-Storey
Approx. Age16-30 years
Lot Size181 938 ft
Frontage181.0 ft
Depth938.1 ft
GarageAttached
BasementFull, Finished with Walk-Out
CoolingCentral Air
HeatingHeat Pump
FireplaceYes
Parking Spaces21
Listed OnFeb 17, 2026
MLS Size3500-5000
Property Tax$18,338/year

Property Details Available

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Rooms

NameSize (m)Size (ft)Features
Living Room(Main)3.96 x 3.8613.0 x 12.7-
Living Room(Main)3.96 x 3.8613.0 x 12.7-
Living Room(Main)3.96 x 3.8613.0 x 12.7-
Living Room(Main)3.96 x 3.8613.0 x 12.7-
Living Room(Main)3.96 x 3.8613.0 x 12.7-
Living Room(Main)3.96 x 3.8613.0 x 12.7-
Living Room(Main)3.96 x 3.8613.0 x 12.7-
Living Room(Main)3.96 x 3.8613.0 x 12.7-
Living Room(Main)3.96 x 3.8613.0 x 12.7-
Living Room(Main)3.96 x 3.8613.0 x 12.7-
Living Room(Main)3.96 x 3.8613.0 x 12.7-
Living Room(Main)3.96 x 3.8613.0 x 12.7-
Living Room(Main)3.96 x 3.8613.0 x 12.7-
Living Room(Main)3.96 x 3.8613.0 x 12.7-
Kitchen(Main)2.57 x 9.028.4 x 29.6-
Kitchen(Main)2.57 x 9.028.4 x 29.6-
Kitchen(Main)2.57 x 9.028.4 x 29.6-
Kitchen(Main)2.57 x 9.028.4 x 29.6-
Kitchen(Main)2.57 x 9.028.4 x 29.6-
Kitchen(Main)2.57 x 9.028.4 x 29.6-
Kitchen(Main)2.57 x 9.028.4 x 29.6-
Kitchen(Main)2.57 x 9.028.4 x 29.6-
Kitchen(Main)2.57 x 9.028.4 x 29.6-
Kitchen(Main)2.57 x 9.028.4 x 29.6-
Kitchen(Main)2.57 x 9.028.4 x 29.6-
Kitchen(Main)2.57 x 9.028.4 x 29.6-
Kitchen(Main)2.57 x 9.028.4 x 29.6-
Kitchen(Main)2.57 x 9.028.4 x 29.6-
Dining Room(Main)3.63 x 4.5711.9 x 15.0-
Dining Room(Main)3.63 x 4.5711.9 x 15.0-
Dining Room(Main)3.63 x 4.5711.9 x 15.0-
Dining Room(Main)3.63 x 4.5711.9 x 15.0-
Dining Room(Main)3.63 x 4.5711.9 x 15.0-
Dining Room(Main)3.63 x 4.5711.9 x 15.0-
Dining Room(Main)3.63 x 4.5711.9 x 15.0-
Dining Room(Main)3.63 x 4.5711.9 x 15.0-
Dining Room(Main)3.63 x 4.5711.9 x 15.0-
Dining Room(Main)3.63 x 4.5711.9 x 15.0-
Dining Room(Main)3.63 x 4.5711.9 x 15.0-
Dining Room(Main)3.63 x 4.5711.9 x 15.0-
Dining Room(Main)3.63 x 4.5711.9 x 15.0-
Dining Room(Main)3.63 x 4.5711.9 x 15.0-
Family Room(Main)4.65 x 3.9415.3 x 12.9-
Family Room(Main)4.65 x 3.9415.3 x 12.9-
Family Room(Main)4.65 x 3.9415.3 x 12.9-
Family Room(Main)4.65 x 3.9415.3 x 12.9-
Family Room(Main)4.65 x 3.9415.3 x 12.9-
Family Room(Main)4.65 x 3.9415.3 x 12.9-
Family Room(Main)4.65 x 3.9415.3 x 12.9-
Family Room(Main)4.65 x 3.9415.3 x 12.9-
Family Room(Main)4.65 x 3.9415.3 x 12.9-
Family Room(Main)4.65 x 3.9415.3 x 12.9-
Family Room(Main)4.65 x 3.9415.3 x 12.9-
Family Room(Main)4.65 x 3.9415.3 x 12.9-
Family Room(Main)4.65 x 3.9415.3 x 12.9-
Family Room(Main)4.65 x 3.9415.3 x 12.9-
Bedroom(Main)3.33 x 3.9910.9 x 13.1-
Bedroom(Main)3.33 x 3.9910.9 x 13.1-
Bedroom(Main)3.33 x 3.9910.9 x 13.1-
Bedroom(Main)3.33 x 3.9910.9 x 13.1-
Bedroom(Main)3.33 x 3.9910.9 x 13.1-
Bedroom(Main)3.33 x 3.9910.9 x 13.1-
Bedroom(Main)3.33 x 3.9910.9 x 13.1-
Bedroom(Main)3.33 x 3.9910.9 x 13.1-
Bedroom(Main)3.33 x 3.9910.9 x 13.1-
Bedroom(Main)3.33 x 3.9910.9 x 13.1-
Bedroom(Main)3.33 x 3.9910.9 x 13.1-
Bedroom(Main)3.33 x 3.9910.9 x 13.1-
Bedroom(Main)3.33 x 3.9910.9 x 13.1-
Bedroom(Main)3.33 x 3.9910.9 x 13.1-
Office(Main)3.33 x 3.3510.9 x 11.0-
Office(Main)3.33 x 3.3510.9 x 11.0-
Office(Main)3.33 x 3.3510.9 x 11.0-
Office(Main)3.33 x 3.3510.9 x 11.0-
Office(Main)3.33 x 3.3510.9 x 11.0-
Office(Main)3.33 x 3.3510.9 x 11.0-
Office(Main)3.33 x 3.3510.9 x 11.0-
Office(Main)3.33 x 3.3510.9 x 11.0-
Office(Main)3.33 x 3.3510.9 x 11.0-
Office(Main)3.33 x 3.3510.9 x 11.0-
Office(Main)3.33 x 3.3510.9 x 11.0-
Office(Main)3.33 x 3.3510.9 x 11.0-
Office(Main)3.33 x 3.3510.9 x 11.0-
Office(Main)3.33 x 3.3510.9 x 11.0-
Den(Main)2.01 x 4.96.6 x 16.1-
Den(Main)2.01 x 4.96.6 x 16.1-
Den(Main)2.01 x 4.96.6 x 16.1-
Den(Main)2.01 x 4.96.6 x 16.1-
Den(Main)2.01 x 4.96.6 x 16.1-
Den(Main)2.01 x 4.96.6 x 16.1-
Den(Main)2.01 x 4.96.6 x 16.1-
Den(Main)2.01 x 4.96.6 x 16.1-
Den(Main)2.01 x 4.96.6 x 16.1-
Den(Main)2.01 x 4.96.6 x 16.1-
Den(Main)2.01 x 4.96.6 x 16.1-
Den(Main)2.01 x 4.96.6 x 16.1-
Den(Main)2.01 x 4.96.6 x 16.1-
Den(Main)2.01 x 4.96.6 x 16.1-
Bedroom(Second)3.35 x 3.8911.0 x 12.8-
Bedroom(Second)3.35 x 3.8911.0 x 12.8-
Bedroom(Second)3.35 x 3.8911.0 x 12.8-
Bedroom(Second)3.35 x 3.8911.0 x 12.8-
Bedroom(Second)3.35 x 3.8911.0 x 12.8-
Bedroom(Second)3.35 x 3.8911.0 x 12.8-
Bedroom(Second)3.35 x 3.8911.0 x 12.8-
Bedroom(Second)3.35 x 3.8911.0 x 12.8-
Bedroom(Second)3.35 x 3.8911.0 x 12.8-
Bedroom(Second)3.35 x 3.8911.0 x 12.8-
Bedroom(Second)3.35 x 3.8911.0 x 12.8-
Bedroom(Second)3.35 x 3.8911.0 x 12.8-
Bedroom(Second)3.35 x 3.8911.0 x 12.8-
Bedroom(Second)3.35 x 3.8911.0 x 12.8-
Bedroom(Second)3.35 x 3.8611.0 x 12.7-
Bedroom(Second)3.35 x 3.8611.0 x 12.7-
Bedroom(Second)3.35 x 3.8611.0 x 12.7-
Bedroom(Second)3.35 x 3.8611.0 x 12.7-
Bedroom(Second)3.35 x 3.8611.0 x 12.7-
Bedroom(Second)3.35 x 3.8611.0 x 12.7-
Bedroom(Second)3.35 x 3.8611.0 x 12.7-
Bedroom(Second)3.35 x 3.8611.0 x 12.7-
Bedroom(Second)3.35 x 3.8611.0 x 12.7-
Bedroom(Second)3.35 x 3.8611.0 x 12.7-
Bedroom(Second)3.35 x 3.8611.0 x 12.7-
Bedroom(Second)3.35 x 3.8611.0 x 12.7-
Bedroom(Second)3.35 x 3.8611.0 x 12.7-
Bedroom(Second)3.35 x 3.8611.0 x 12.7-
Bedroom(Second)3.38 x 4.2911.1 x 14.1-
Bedroom(Second)3.38 x 4.2911.1 x 14.1-
Bedroom(Second)3.38 x 4.2911.1 x 14.1-
Bedroom(Second)3.38 x 4.2911.1 x 14.1-
Bedroom(Second)3.38 x 4.2911.1 x 14.1-
Bedroom(Second)3.38 x 4.2911.1 x 14.1-
Bedroom(Second)3.38 x 4.2911.1 x 14.1-
Bedroom(Second)3.38 x 4.2911.1 x 14.1-
Bedroom(Second)3.38 x 4.2911.1 x 14.1-
Bedroom(Second)3.38 x 4.2911.1 x 14.1-
Bedroom(Second)3.38 x 4.2911.1 x 14.1-
Bedroom(Second)3.38 x 4.2911.1 x 14.1-
Bedroom(Second)3.38 x 4.2911.1 x 14.1-
Bedroom(Second)3.38 x 4.2911.1 x 14.1-
Bedroom(Second)3.28 x 4.0110.8 x 13.2-
Bedroom(Second)3.28 x 4.0110.8 x 13.2-
Bedroom(Second)3.28 x 4.0110.8 x 13.2-
Bedroom(Second)3.28 x 4.0110.8 x 13.2-
Bedroom(Second)3.28 x 4.0110.8 x 13.2-
Bedroom(Second)3.28 x 4.0110.8 x 13.2-
Bedroom(Second)3.28 x 4.0110.8 x 13.2-
Bedroom(Second)3.28 x 4.0110.8 x 13.2-
Bedroom(Second)3.28 x 4.0110.8 x 13.2-
Bedroom(Second)3.28 x 4.0110.8 x 13.2-
Bedroom(Second)3.28 x 4.0110.8 x 13.2-
Bedroom(Second)3.28 x 4.0110.8 x 13.2-
Bedroom(Second)3.28 x 4.0110.8 x 13.2-
Bedroom(Second)3.28 x 4.0110.8 x 13.2-
Primary Bedroom(Second)5.82 x 5.3119.1 x 17.4-
Primary Bedroom(Second)5.82 x 5.3119.1 x 17.4-
Primary Bedroom(Second)5.82 x 5.3119.1 x 17.4-
Primary Bedroom(Second)5.82 x 5.3119.1 x 17.4-
Primary Bedroom(Second)5.82 x 5.3119.1 x 17.4-
Primary Bedroom(Second)5.82 x 5.3119.1 x 17.4-
Primary Bedroom(Second)5.82 x 5.3119.1 x 17.4-
Primary Bedroom(Second)5.82 x 5.3119.1 x 17.4-
Primary Bedroom(Second)5.82 x 5.3119.1 x 17.4-
Primary Bedroom(Second)5.82 x 5.3119.1 x 17.4-
Primary Bedroom(Second)5.82 x 5.3119.1 x 17.4-
Primary Bedroom(Second)5.82 x 5.3119.1 x 17.4-
Primary Bedroom(Second)5.82 x 5.3119.1 x 17.4-
Primary Bedroom(Second)5.82 x 5.3119.1 x 17.4-
Den(Second)2.72 x 2.978.9 x 9.7-
Den(Second)2.72 x 2.978.9 x 9.7-
Den(Second)2.72 x 2.978.9 x 9.7-
Den(Second)2.72 x 2.978.9 x 9.7-
Den(Second)2.72 x 2.978.9 x 9.7-
Den(Second)2.72 x 2.978.9 x 9.7-
Den(Second)2.72 x 2.978.9 x 9.7-
Den(Second)2.72 x 2.978.9 x 9.7-
Den(Second)2.72 x 2.978.9 x 9.7-
Den(Second)2.72 x 2.978.9 x 9.7-
Den(Second)2.72 x 2.978.9 x 9.7-
Den(Second)2.72 x 2.978.9 x 9.7-
Den(Second)2.72 x 2.978.9 x 9.7-
Den(Second)2.72 x 2.978.9 x 9.7-
Laundry(Second)1.83 x 2.976.0 x 9.7-
Laundry(Second)1.83 x 2.976.0 x 9.7-
Laundry(Second)1.83 x 2.976.0 x 9.7-
Laundry(Second)1.83 x 2.976.0 x 9.7-
Laundry(Second)1.83 x 2.976.0 x 9.7-
Laundry(Second)1.83 x 2.976.0 x 9.7-
Laundry(Second)1.83 x 2.976.0 x 9.7-
Laundry(Second)1.83 x 2.976.0 x 9.7-
Laundry(Second)1.83 x 2.976.0 x 9.7-
Laundry(Second)1.83 x 2.976.0 x 9.7-
Laundry(Second)1.83 x 2.976.0 x 9.7-
Laundry(Second)1.83 x 2.976.0 x 9.7-
Laundry(Second)1.83 x 2.976.0 x 9.7-
Laundry(Second)1.83 x 2.976.0 x 9.7-
Office(Lower)3.33 x 3.410.9 x 11.2-
Office(Lower)3.33 x 3.410.9 x 11.2-
Office(Lower)3.33 x 3.410.9 x 11.2-
Office(Lower)3.33 x 3.410.9 x 11.2-
Office(Lower)3.33 x 3.410.9 x 11.2-
Office(Lower)3.33 x 3.410.9 x 11.2-
Office(Lower)3.33 x 3.410.9 x 11.2-
Office(Lower)3.33 x 3.410.9 x 11.2-
Office(Lower)3.33 x 3.410.9 x 11.2-
Office(Lower)3.33 x 3.410.9 x 11.2-
Office(Lower)3.33 x 3.410.9 x 11.2-
Office(Lower)3.33 x 3.410.9 x 11.2-
Office(Lower)3.33 x 3.410.9 x 11.2-
Office(Lower)3.33 x 3.410.9 x 11.2-
Bedroom(Lower)3.38 x 3.5111.1 x 11.5-
Bedroom(Lower)3.38 x 3.5111.1 x 11.5-
Bedroom(Lower)3.38 x 3.5111.1 x 11.5-
Bedroom(Lower)3.38 x 3.5111.1 x 11.5-
Bedroom(Lower)3.38 x 3.5111.1 x 11.5-
Bedroom(Lower)3.38 x 3.5111.1 x 11.5-
Bedroom(Lower)3.38 x 3.5111.1 x 11.5-
Bedroom(Lower)3.38 x 3.5111.1 x 11.5-
Bedroom(Lower)3.38 x 3.5111.1 x 11.5-
Bedroom(Lower)3.38 x 3.5111.1 x 11.5-
Bedroom(Lower)3.38 x 3.5111.1 x 11.5-
Bedroom(Lower)3.38 x 3.5111.1 x 11.5-
Bedroom(Lower)3.38 x 3.5111.1 x 11.5-
Bedroom(Lower)3.38 x 3.5111.1 x 11.5-
Office(Lower)3.66 x 2.9212.0 x 9.6-
Office(Lower)3.66 x 2.9212.0 x 9.6-
Office(Lower)3.66 x 2.9212.0 x 9.6-
Office(Lower)3.66 x 2.9212.0 x 9.6-
Office(Lower)3.66 x 2.9212.0 x 9.6-
Office(Lower)3.66 x 2.9212.0 x 9.6-
Office(Lower)3.66 x 2.9212.0 x 9.6-
Office(Lower)3.66 x 2.9212.0 x 9.6-
Office(Lower)3.66 x 2.9212.0 x 9.6-
Office(Lower)3.66 x 2.9212.0 x 9.6-
Office(Lower)3.66 x 2.9212.0 x 9.6-
Office(Lower)3.66 x 2.9212.0 x 9.6-
Office(Lower)3.66 x 2.9212.0 x 9.6-
Office(Lower)3.66 x 2.9212.0 x 9.6-
Bedroom(Lower)4.22 x 3.5613.8 x 11.7-
Bedroom(Lower)4.22 x 3.5613.8 x 11.7-
Bedroom(Lower)4.22 x 3.5613.8 x 11.7-
Bedroom(Lower)4.22 x 3.5613.8 x 11.7-
Bedroom(Lower)4.22 x 3.5613.8 x 11.7-
Bedroom(Lower)4.22 x 3.5613.8 x 11.7-
Bedroom(Lower)4.22 x 3.5613.8 x 11.7-
Bedroom(Lower)4.22 x 3.5613.8 x 11.7-
Bedroom(Lower)4.22 x 3.5613.8 x 11.7-
Bedroom(Lower)4.22 x 3.5613.8 x 11.7-
Bedroom(Lower)4.22 x 3.5613.8 x 11.7-
Bedroom(Lower)4.22 x 3.5613.8 x 11.7-
Bedroom(Lower)4.22 x 3.5613.8 x 11.7-
Bedroom(Lower)4.22 x 3.5613.8 x 11.7-
Utility Room(Lower)3.71 x 2.1112.2 x 6.9-
Utility Room(Lower)3.71 x 2.1112.2 x 6.9-
Utility Room(Lower)3.71 x 2.1112.2 x 6.9-
Utility Room(Lower)3.71 x 2.1112.2 x 6.9-
Utility Room(Lower)3.71 x 2.1112.2 x 6.9-
Utility Room(Lower)3.71 x 2.1112.2 x 6.9-
Utility Room(Lower)3.71 x 2.1112.2 x 6.9-
Utility Room(Lower)3.71 x 2.1112.2 x 6.9-
Utility Room(Lower)3.71 x 2.1112.2 x 6.9-
Utility Room(Lower)3.71 x 2.1112.2 x 6.9-
Utility Room(Lower)3.71 x 2.1112.2 x 6.9-
Utility Room(Lower)3.71 x 2.1112.2 x 6.9-
Utility Room(Lower)3.71 x 2.1112.2 x 6.9-
Utility Room(Lower)3.71 x 2.1112.2 x 6.9-
Utility Room(Lower)1.83 x 3.846.0 x 12.6-
Utility Room(Lower)1.83 x 3.846.0 x 12.6-
Utility Room(Lower)1.83 x 3.846.0 x 12.6-
Utility Room(Lower)1.83 x 3.846.0 x 12.6-
Utility Room(Lower)1.83 x 3.846.0 x 12.6-
Utility Room(Lower)1.83 x 3.846.0 x 12.6-
Utility Room(Lower)1.83 x 3.846.0 x 12.6-
Utility Room(Lower)1.83 x 3.846.0 x 12.6-
Utility Room(Lower)1.83 x 3.846.0 x 12.6-
Utility Room(Lower)1.83 x 3.846.0 x 12.6-
Utility Room(Lower)1.83 x 3.846.0 x 12.6-
Utility Room(Lower)1.83 x 3.846.0 x 12.6-
Utility Room(Lower)1.83 x 3.846.0 x 12.6-
Utility Room(Lower)1.83 x 3.846.0 x 12.6-

Room Dimensions Available

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100 Chesswood Trail History

Complete transaction history for this property

Terminated

Listed: Oct 22, 2025

$2,500,000

103 days on marketSale
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5 More Transactions Available

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Transaction History Available

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Price History

Original List Price

$2,300,000

Listed on Feb 17, 2026

Sold Price

$2,110,000

Sold on Jul 13, 2026

-$190,000

-8.3%

102 days on market

Price History Available

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OVAIS QASSIM

Broker of Record

PREMIER MATRIX REALTY LTD. BROKERAGE

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Home Features

Property TypeDetached
Style2-Storey
Approx. Age16-30 years
Lot Size181 × 938 ft
Frontage181.0 ft
Depth938.1 ft
GarageAttached
BasementFull, Finished with Walk-Out
CoolingCentral Air
FireplaceYes

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About 100 Chesswood Trail, Hamilton, ON L8N 2Z7

100 Chesswood Trail, Hamilton, ON L8N 2Z7 is a 8-bedroom, 6-bathroom 2-storey detached with approximately 3500-5000 square feet of living space, situated on a 181 938 foot lot. This property is currently sold (sold for $2,110,000). The home features a attached garage and a full, finished with walk-out basement, built approximately 16-30 years ago.

Rural Flamborough Neighbourhood

This home is located in Rural Flamborough, part of Hamilton in the Hamilton area. Explore more homes for sale and recently sold properties in this neighbourhood.

Whether you are looking to buy, sell, or lease in Rural Flamborough, our team of experienced real estate professionals can help you navigate the market and find the perfect home. Contact us today for a free consultation.

100 Chesswood Trail, Hamilton, ON L8N 2Z7

100 Chesswood Trail, Hamilton, ON L8N 2Z7 sold,8 bedroom detached Rural Flamborough,Hamilton homes for sale,Hamilton real estate,2-Storey homes, detached sold