100 Chesswood Trail

FOR SALE
$2,499,000
100 Chesswood Trail, Hamilton
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6 + 2
BEDROOMS
6
BATHROOMS
1
KITCHENS
22
ROOMS
X12799512
MLSID
Contact Us
Property 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.
Property Features
Cul de Sac/Dead End, Golf, Greenbelt/Conservation, School, Place Of Worship, Park, Auto Garage Door Remote, Central Vacuum, Water Heater, Water Softener, Private Double
Property Details
Address
100 Chesswood Trail
Postal Code
L8N 2Z7
Property Type
Detached, Detached
Zoning
A2
Lot Size
181' x 938'
Taxes
$18,338 (2025
Basement
Full, Finished with Walk-Out
Exterior
Landscaped, Privacy, Patio, Porch
Heat Type
Heat Pump
Heat Source
Ground Source
Water
Well
Parking Spaces
18
Garage Type
Attached
Listing contracted with Royal Lepage Real Estate Associates
34 Penfold Court, Hamilton
5+1
BEDS
5
BATHS
$2,249,900
FOR SALE
Custom-built home with over 5000 sqft of finished living space, meticulously maintained by original owners. It offers 2 primary bedrooms, as well as a full in law suite, ideal for a multi generational family. Situated on an oversized pie shaped lot, 10 min to Upper James shopping. This stunning property boasts a wide stamped concrete drive w/ parking for 4 vehicles + oversized double car garage, 11 ft in height, w/ 9 foot high garage doors, perfect to accommodate a car lift. Main floor features a dream kitchen with custom cabinetry, quartz countertops, extra large sink & eating area with oversized patio door leading to the backyard oasis. Main floor primary bed w/ walk in closet & 6pc ensuite. Bright & spacious 2 storey family rm w/ natural gas fireplace, separate living & dining room, bed/office, 2 pc bath & main floor laundry off of the garage. The upper level offers a family room, 3 bedrooms, including 2 that offer ensuites & walk in closets. Fully finished basement has a full kitchen with dining area, rec room, bed w/ ensuite privilege to 3pc bath, office, workshop, 2nd laundry rm, + hot tub & hobby room. Gorgeous backyard featuring inground saltwater pool with new heater, stamped concrete surround, Trex decking on patio & in the covered outdoor kitchen area, outdoor speakers & oversized custom shed. 4 season sunroom is the perfect place to relax. Recent updates include pool heater 2025, roof shingles 2020, shed & sun rm shingles 2022, furnace & A/C 2023.This home must be seen! Luxury Certified.
248 Cloverleaf Drive, Hamilton
5+1
BEDS
5
BATHS
$1,995,000
FOR SALE
Welcome to 248 Cloverleaf Drive in Ancaster - an elegant & spacious executive home in a quiet, family-friendly area backing onto a forest. With over 3,500 sq. ft. above grade, plus a professionally finished basement (2022), this home has5+1 bedrooms, 4.5 bathrooms & a layout designed for modern living. The main floor combines formal & open spaces, including a separate living room & dining room, a large bright eat-in kitchen, family room with fireplace, 2-piece washroom & separate laundry room. Upstairs are five generous bedrooms & three full, renovated bathrooms including a luxurious primary bedroom & 5-piece ensuite (2023). The lower level adds versatile living space featuring a recroom with custom fireplace, a glass-enclosed gym, 3-piece bath, office or guest bedroom, wine cellar & large storage room. Step outside to a beautifully landscaped yard with an in-ground gunite pool with water feature, custom pool house, expansive stonework, all backing onto a picturesque, forested area. Other recent updates include: metal roof (2023), new garage doors (2023), furnace & AC (2022) pool heater (2025) chlorinator (2024). Close to excellent schools, parks, Hamilton Golf & Country Club, shopping & highway access - this is a superior, move-in-ready home. **INTERBOARD LISTING: CORNERSTONE ASSOCIATION OF REALTORS**
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