29 Woodside Drive, Hamilton, ON L8T 1C4
Sherwood, Hamilton · Near High St. · View map
About this home
A fantastic home, an extraordinary lifestyle! Set on a spectacular, professionally landscaped property in one of Hamilton's sought after East Mountain neighbourhoods, this impressive centre hall plan brings an exceptional combination of elegance, generous living spaces and resort-inspired luxury. Beautifully refreshed with neutral décor, the home welcomes you with spacious principal rooms, including an elegant formal dining room, private home office and fabulous Great Room with multiple walkouts to the backyard paradise. A main-floor bedroom with its own private entrance provides wonderful flexibility for guests or extended family. Upstairs, 4 spacious bedrooms offer comfortable family living. Stunning updated primary ensuite (June 2026) and refreshed 4 pc. bathroom. The finished lower level is an entertainer's delight, featuring a family room with fireplace, wet bar, recreation and fitness areas, and sauna. Two separate basement entrances add versatility and potential for multi-generational living. Step outside and discover your own private vacation destination! The magnificent, fully fenced grounds are designed for relaxation and entertaining, complete with a heated 20' x 40' inground pool, expansive deck, inviting patios, charming gazebo and fabulous outdoor kitchen featuring stone countertops, built-in gas BBQ, two-burner cooktop and two refrigerators. An inground sprinkler system helps maintain the lush, beautifully manicured landscape. An exceptional property where everyday living feels like a getaway! With room for the whole family, wonderful spaces to entertain and an outdoor setting that rivals a luxury resort, this is a home to enjoy, inside and out, for years to come.
The home
- Type
- Detached home
- Style
- 2-Storey
- Square footage
- 2500-3000 sq ft
- Bedrooms
- 5
- Bathrooms
- 4
- Kitchens
- 1
- Rooms
- 10
- Basement
- Full, Walk-Up, Separate Entrance, Finished
- Lot size
- 80 x 153.1 ft
- Faces
- South
- View
- Garden, Skyline
- Approximate age
- 51-99 years
Ownership & fees
- Ownership
- Freehold
- Monthly condo fee
- None
- Security
- Alarm System, Carbon Monoxide Detectors, Security System, Smoke Detector
- Exterior
- Brick, Vinyl Siding
Heating & cooling
- Heating fuel
- Gas
- Heating type
- Forced Air
- Air conditioning
- Central Air
- Fireplace
- Yes
Garage & parking
- Garage
- Attached
- Garage spaces
- 2
- Driveway spaces
- 4
- Total parking
- 6
- Parking features
- Private Double
Taxes & other
- Property taxes
- $9,422/yr
- Tax year
- 2026
- Occupancy
- Owner
- Possession
- 60 Days/TBD
- Cross street
- High St.
- Neighbourhood
- Sherwood
More
- Price per sq ft
- ~$509 (at 2,750 sq ft)
- MLS® number
- X14171602
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The home and its surroundings
- Auto Garage Door Remote
- Bar Fridge
- Built-In Oven
- Countertop Range
- Garburator
- In-Law Capability
- Primary Bedroom - Main Floor
- Sauna
- Storage
- Upgraded Insulation
- Water Heater Owned
- Water Meter
- Hospital
- Library
- Park
- Place Of Worship
- School
- Public Transit
- Deck
- Landscape Lighting
- Landscaped
- Lawn Sprinkler System
- Patio
- Privacy
- Porch
- Year Round Living
- Mortgage
- Property tax
- Maintenance fee
Cash needed to close
Estimates only, using Canadian semi-annual compounding, Ontario land transfer tax. Mortgage default insurance is added when you put down less than 20%. Your lender and lawyer will confirm exact numbers.
29 Woodside Drive, Hamilton, ON L8T 1C4
Sherwood, Hamilton · Near High St.
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Listing history for 29 Woodside Drive
See what this home and others at the same address were listed for, what they sold for, and how long it took.
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Frequently asked questions about 29 Woodside Drive
Answers come straight from this home’s MLS® listing.
How much is 29 Woodside Drive listed for, and what would it cost each month?
29 Woodside Drive is listed for $1,399,000. With 20% down ($279,800), the mortgage payment would be roughly $5,643 a month at 4.5% over 30 years. Add property tax and the estimate comes to about $6,428 a month, all in. That figure is an illustration, not a quote.
Is 29 Woodside Drive freehold or a condo, and is there a monthly fee?
29 Woodside Drive is a detached home in Sherwood, Hamilton. Ownership is freehold: you own the home and the lot. There is no monthly condo fee, so the roof, windows, driveway, snow and lawn are yours to look after.
How many bedrooms and bathrooms does 29 Woodside Drive have?
29 Woodside Drive has 5 bedrooms and 4 bathrooms. The listing gives the style as 2-storey.
Does 29 Woodside Drive have a garage and parking?
Yes. The listing shows the garage as attached, with room for 2 cars. The driveway adds 4 spaces. In total the listing counts 6 parking spaces.
Does 29 Woodside Drive have a finished basement?
The listing describes the basement as full, walk-up, separate entrance, finished. Finished basement space is usually not counted in the square footage shown. A listing description is not proof of a legal second unit, so confirm zoning and permits with the municipality before counting on rental income.
What style of home is 29 Woodside Drive?
29 Woodside Drive is a detached home. A detached home stands on its own lot with no shared walls.
Does 29 Woodside Drive have a pool?
Yes. The listing shows inground for the pool. Ask about its age, liner and equipment before you offer, since those are the costly parts to replace.
How big is 29 Woodside Drive, and what is the lot size?
The listing puts the home between 2,500 and 3,000 sq ft. The board reports a range rather than an exact figure, and it usually leaves out the basement. The lot is listed as 80 x 153.1 ft.
How is 29 Woodside Drive heated and cooled?
Heating is forced air (gas). Cooling is central air.
What are the property taxes for 29 Woodside Drive?
Property taxes are $9,422 a year (2026), or about $785 a month.
Where is 29 Woodside Drive?
29 Woodside Drive is in the Sherwood community of Hamilton. The nearest main intersection is High St.. The postal code is L8T 1C4.
Is 29 Woodside Drive still for sale?
Yes. It is an active listing (MLS® X14171602). Listings here update from the board through the day and come down once a home sells.
What are similar properties near 29 Woodside Drive asking?
Similar properties for sale nearby right now include 9 Donlea Drive at $999,000 (3 bed), 575 Stonehenge Drive at $1,299,900 (4+1 bed) and 232 Cornwallis Road at $1,499,999 (4+1 bed). These are asking prices, not sold prices. The Sold history tab shows what homes at this address went for.
What have homes at 29 Woodside Drive sold for?
Recent sales, leases and expired listings for this home and others at the same address are in the Sold history tab, with the price and date of each. It is free for members.
How do I book a showing at 29 Woodside Drive?
Pick a day and time with Book a Tour on this page. Tours are free, with no obligation, in person or by video. You can also call or text 647-931-3923.
Have a different question? Ask about this home and get an answer, usually within the hour.
Similar properties nearby
More properties for sale near Sherwood, picked by style, size and price.
Detached home$999,0009 Donlea Drive, Hamilton3 bed · 3 bath · SherwoodCourtesy of: RE/MAX ESCARPMENT REALTY INC.View home →
Detached home$1,299,900575 Stonehenge Drive, Hamilton4+1 bed · 4 bath · MeadowlandsCourtesy of: ROYAL LEPAGE STATE REALTYView home →
Detached home$1,499,999232 Cornwallis Road, Hamilton4+1 bed · 4 bath · AncasterCourtesy of: EXP REALTYView home →Courtesy of: ROYAL LEPAGE STATE REALTY
Listing information comes from the Toronto Regional Real Estate Board through PropTx and is deemed reliable but is not guaranteed accurate. It is provided for consumers' personal, non-commercial use. The trademarks MLS®, Multiple Listing Service® and the associated logos are owned by The Canadian Real Estate Association (CREA) and identify the quality of services provided by real estate professionals who are members of CREA.
*Estimated monthly cost assumes 20% down, a 4.5% rate and a 30-year amortization, plus property tax. For illustration only.