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.
5 bedrooms, 3 bathrooms, about 2,500 sq ft, works out to roughly $560 per square foot. Chat with Zara if you'd like a deeper read on whether this detached fits your budget and timing.
Inside 29 Woodside Dr
Every detail from the listing, in one place.
Type
Detached
Style
2-Storey
Living space
2500-3000 sq ftas stated on the listing
Parking
6 spacesYes garage
Basement
Full, Walk-Up
Features & systems
Parking & garage
Garage
Yes
Parking spaces
6
Interior
Basement
Full · Walk-Up
Exterior & construction
Pool
Yes
Lot & land
Lot size (sqft)
12248
Listing & possession
Property style
2-Storey
Property class
Detached
29 Woodside Dr Price & Sale History
Earlier listings of this property, list-price changes, and the most recent annual property tax on the listing.
For saleListedThis listingMLS® X14171602$1,399,000
Sourced from MLS®. Includes earlier listings of this property on record.
What's it worth?
How 29 Woodside Dr Compares to the Hamilton Market
Zara compares it with recent sales of similar homes nearby. It's a guide, not an appraisal.
Independent mortgage broker · OAC · rates subject to change and underwritingMortgage Squad →
Referral disclosure: Summitly may refer you to Mortgage Squad Advisors, an affiliated mortgage partner. You are free to choose any lender or mortgage professional.
Monthly cost
Enter a rate to see the monthly cost
An estimate, not a quote. Utilities and insurance are extra.
Affordability calculator
Estimated monthly payment
$6,873
/mo
based on the purchase price of $1,399,000
$279,800 cash
$1,119,200 financed
$942,660 total interest
Principal54%$1,119,200
Interest46%$942,660
20% down · 25-yr amortization · 5.50% rate. Principal & interest only — taxes, condo fees, and insurance not included.
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Figures are Summitly estimates for illustration only — not from TRREB or the MLS® feed, and not a mortgage approval, appraisal, or financial advice.
Rental income potential
Est. monthly rent
low–high
Gross yield
rent × 12 ÷ price
Cap rate (est.)
net of tax + fees
Summitly AI estimate for discussion only — not from TRREB or the MLS® feed, and not an appraisal or investment advice. Yield and cap rate are derived from the estimated rent versus the asking price.
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Mortgage financing is arranged through Mortgage Squad Advisors. Summitly is the technology platform that powers this site. Estimated values, AI insights, calculator results, and rental projections shown on this page are generated by Summitly and are not provided by, reviewed by, or sourced from TRREB, the MLS®, or the listing brokerage; they are not appraisals or opinions of value. The trademarks REALTOR®, REALTORS®, and the REALTOR® logo are controlled by the Canadian Real Estate Association (CREA) and identify real estate professionals who are members of CREA. The Coldwell Banker® name and logo are trademarks of Coldwell Banker Real Estate LLC.
Similar homes for sale nearby in Hamilton
Other 4-bed homes for sale in Hamilton around $1.4M.
Average days on market41Homes sold in about 41 days on average.
Sale-to-list ratio96.9%On average, homes sold below asking.
Active listings2,532Homes for sale here right now.
Median vs prior 90 days−3.1%Compared with May 15 – Aug 13, 2026: prices down.
Based on 1,850 sales from Aug 13 – Nov 11, 2026 (1,568 in the prior 90 days). Aggregate MLS® figures for closed sales; individual sold prices are shown only to signed-in members.
Questions About 29 Woodside Dr
How much is 29 Woodside Dr listed for?
29 Woodside Dr is listed at $1,399,000 (MLS® X14171602). Summitly updates the price as soon as the MLS® record changes.
Is $1,399,000 a good price for 29 Woodside Dr?
Summitly rates it Good Deal: the asking price is 3% to 10% below Zara's estimate, an estimate built from recent sales in Hamilton. The rating is an automated opinion, not an appraisal; "What's it worth?" on this page shows how it is worked out. See Zara's estimate
Has the price of 29 Woodside Dr changed?
No — 29 Woodside Dr is still listed at its original asking price of $1,399,000.
How many bedrooms and bathrooms does 29 Woodside Dr have?
29 Woodside Dr has 5 bedrooms and 3 bathrooms, with about 2,500–3,000 square feet of living space. It is a detached home in Hamilton.
How much would the monthly mortgage be on 29 Woodside Dr?
About $6,873 a month — principal and interest on $1,399,000 with 20% down ($279,800), a 25-year amortization and an assumed 5.5% interest rate. The mortgage calculator on this page lets you change the down payment, amortization and rate.
How does 29 Woodside Dr compare with other homes in Hamilton?
Its asking price of $1,399,000 is about 108% above the median sold price in Hamilton over the last 90 days, $673,000, across 1,850 closed sales on the TRREB MLS®. A city median mixes every type and size of home, so the comparable sales on this page are the closer guide.
Has 29 Woodside Dr been sold before?
Summitly has no earlier MLS® sale or lease of 29 Woodside Dr on record from the last two years. Older records aren't shown under TRREB rules.
Where is 29 Woodside Dr?
29 Woodside Dr is in Hamilton, ON. Schools, transit, parks and shops nearby are under Location & lifestyle on this page.
How long has 29 Woodside Dr been on the market?
29 Woodside Dr was listed today (November 11, 2026).
What is the price per square foot of 29 Woodside Dr?
About $466 to $560 per square foot: the asking price of $1,399,000 over the 2,500–3,000 sq ft the listing gives as its size range.
Does 29 Woodside Dr have parking or a garage?
Yes — the listing gives 6 parking spaces. Garage: Yes.
Does 29 Woodside Dr have a basement, and is it finished?
The listing describes the basement as: Full, Walk-Up.
