$2,300,000
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100 Chesswood Trail, Flamborough on L8N 2Z7, Flamborough, ON L8N 2Z7

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8 Beds
6 Baths
4,629 Sq Ft

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.

Listing By: Kyrsten Feere - Royal LePage Real Estate Associates cnitso Realty.com
  • MLS® 40805215
  • Date Listed02/18/2026
  • Days on Realty 108 Days
  • Bedrooms 8
  • Bathrooms 4 Full baths, 2 Half baths
  • Lot Size 3 sq. ft
  • Sewer Septic Tank
  • Property Type Single Family Residence
  • County Hamilton
  • Year Built 2015
  • Water Well
  • Square Feet 4,629 sq. ft
  • Price Per Sq. Ft $496.87

Interior Features

  • Appliances Water Heater, Water Softener, Dishwasher, Dryer, Refrigerator, Stove, Washer
  • Cooling Central Air
  • Heating Geothermal

Exterior / Lot Features

  • Exterior Landscaped, Privacy
  • Roof -
  • Lot Size Acres -
  • Lot Size SQFT 3.34
  • Lot Features Rural, Pie Shaped Lot, Ample Parking, Cul- De- Sac, Near Golf Course, Greenbelt, Hospital, Landscaped, Open Spaces, Park, Place of Worship, Playground Nearby, Quiet Area, Rec./ Community Centre, Schools, Shopping Nearby, Trails

Sales & Tax History

Source: Public Records

Local Neighborhood Highlights for L8N 2Z7

Discover key demographics, population statistics, and environmental insights for the Flamborough, ON area.

Walkability in ON / L8N 2Z7

Source: Walk Score

4/100

Car-Dependent

Walk Score ®

0/100

Minimal Transit

Transit Score ®

26/100

Bikable

Bike Score ®

Overview

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

Transit Summary

0 nearby routes: 0 bus, 0 rail, 0 other

Walkability averages in the surrounding area

The average walkability score in the surrounding area is Walk Score: 2/100, Transit Score: 0/100, Bike Score: 24/100.

Points of Interest near 100 Chesswood Trail, Flamborough ON L8N 2Z7, Flamborough, ON L8N 2Z7

Frequently Asked Questions for 100 Chesswood Trail, Flamborough ON L8N 2Z7

Source: Realty.com

100 Chesswood Trail, Flamborough ON L8N 2Z7, Flamborough, ON L8N 2Z7 in Flamborough, ON L8N 2Z7 is a single family residence listed at $2,300,000. Highlights include 8 bedrooms, 6 bathrooms, 4,629 sq. ft., built in 2015, $497 per sq. ft.. Realty.ca has 44 photos, sales history, school insights, and mortgage tools fo...

Realty.com has 44 photos of 100 Chesswood Trail, Flamborough ON L8N 2Z7.

Our records indicate that 100 Chesswood Trail, Flamborough ON L8N 2Z7 was built in 2015.

The full address for this home is 100 Chesswood Trail, Flamborough ON L8N 2Z7, Flamborough, ON L8N 2Z7.

100 Chesswood Trail, Flamborough ON L8N 2Z7 has been listed on Realty.com since Wed February 18, 2026

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

The average walkability score in the surrounding area is Walk Score: 2/100, Transit Score: 0/100, Bike Score: 24/100.

Listing provided courtesy of: Keller Williams Real Estate Associates - itso - 1839902 (tel: 905-812-8123)
Listing agent: Kyrsten Feere - UnknownState (tel: 905-689-0002)

This content last refreshed on 2026-06-06 04:15:47. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.