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CA > Ontario > Hamilton > Sherwood > 29 Woodside Drive

29 Woodside Drive, Hamilton, ON

Hamilton, Sherwood Hood
High St.
5 Br | 4 Bath | 2500-3000 Sqft
$1,399,000 For Sale

Property Overview

  • Detached — 2-Storey
  • SqFt: | 2500-3000 Sqft
  • Lot Size: 80.00 x 153.10 Feet
  • Age: 51-99 Years
  • Basement: Full, Walk-Up, Separate Entrance, Finished
  • Exterior: Brick, Vinyl Siding
  • Taxes: 9,422 / 2026
  • Zoning: n/a
  • MLS #: X14171602
  • Sewer: Sewer
  • Heat Source: Gas , Forced Air

Property Description

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.

Use Supplement with full list of Inclusions & exclusions per Schedule C; B/in Induction cooktop, 2 b/in Convection ovens, S/S fridge, Dishwasher, existing light fixtures & ceiling fans, Washer & Dryer, window coverings, 2 hot water tanks, 2 c/air units, 2 furnaces, Pool equipment; gas heater, pump & filter w/ cells, water fountain, winter cover, Outdoor kitchen; Gas BBQ, 2 fridges, 2 burner gas cooktop. Bar fridge in Gazebo. Bar fridge in Fam. Rm. & Dishwasher * Central Vac "as is" & attachments, Cold Room; Wine Cabinet "as is", S/S fridge, freezer & black metal shelving, inground sprinkler system, Garage door opener & remote, Exterior lighting, Bar stools main & lower levels

Property Details

  • For: For Sale
  • Type: Detached
  • Style: 2-Storey
  • Lot: 80.00 x 153.10 Feet
  • Region: Hamilton
  • Hood: Sherwood
  • Zoning: n/a
  • Lot Irreg: Fronting on: South
  • Fronting On: South

Building Details

  • Age: 51-99 Years
  • Exterior: Brick, Vinyl Siding
  • Heat: Gas , Forced Air
  • A/C: Central Air
  • Interior Features: 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
  • Pool: Inground
  • Sewer: Sewer
  • Garage: Attached
  • Total Parking: 6.00
  • Driveway: Private Double

Property Interior

  • Sqft: 2500-3000 Sqft
  • Bed: 5
  • Bath: 4
  • Kitchen: 1
  • Family Room: No
  • Basement: Full, Walk-Up, Separate Entrance, Finished
Rooms Details

Foyer

Main Level

2.97 x 4.24

Dining Room

Main Level

3.96 x 7.19

Office

Main Level

3.96 x 3.68

Kitchen

Main Level

7.04 x 3.51

Great Room

Main Level

6.83 x 4.9

Bedroom

Main Level

5.21 x 4.11

Bathroom

Main Level

1.27 x 1.73

Laundry

Main Level

2.79 x 4.83

Primary Bedroom

Second Level

5.28 x 4.06

Bedroom

Second Level

4.19 x 3.12

Bedroom

Second Level

3.76 x 3.35

Bedroom

Second Level

2.77 x 3.02

Bathroom

Second Level

2.9 x 1.96

3 Pc Ensuite

Bathroom

Second Level

3.84 x 1.93

4 Pc Bath

Recreation

Basement Level

5.61 x 4.11

Family Room

Basement Level

5.61 x 4.11

Gas Fireplace, B/I Bar

Bathroom

Basement Level

2.9 x 0.94

3 Pc Bath, Sauna

Other

Basement Level

1.7 x 1.83

Sauna

Cold Room/Cantina

Basement Level

11.18 x 2.69

Utility Room

Basement Level

10.87 x 4.5

Utility Room

Basement Level

10.67 x 2.51

Property Listed by: ROYAL LEPAGE STATE REALTY
Virtual Tour: https://sites.nomorecowboys.media/mls/226665176

Home Valuation Estimate

What is 29 Woodside Drive, Hamilton, ON worth in today’s Sherwood, Hamilton market?

This HomeZira valuation preview helps buyers and sellers think through the asking price for this 5-bedroom Detached with 2500-3000 sq. ft. in Sherwood, Hamilton. The full estimate reviews the property’s location, home type, bedroom count, size range, age, and nearby comparable market activity after sign-in.

Property-specific estimate See a valuation range built around this listing’s local profile.
Comparable market context Review how similar nearby homes help frame value.
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Location

  • Address: 29 Woodside Drive
  • Neighborhood: Sherwood
  • Zip/Postal Code: L8T 1C4
  • Nearby Amenities: Hospital, Library, Park, Place Of Worship, School, Public Transit
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Kazi Hossain

Kazi Hossain

Kazi — Serving the Community for 19 Years!
REALTOR®

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About 29 Woodside Drive, Hamilton, ON L8T 1C4, Hamilton

Located at 29 Woodside Drive, Hamilton, ON in Hamilton (Sherwood neighbourhood), near High St.. This freehold home offers Detached, ["2-Storey"], 5 bedrooms, 4 bathrooms and 2500-3000 sq.ft. (approx.) in a layout suited to everyday family living. Basement: Full, Walk-Up, Separate Entrance, Finished • 6 parking spots • Garage: Attached • Heating: Gas Forced Air • Cooling: Central Air. Property taxes are approximately $9,422 for 2026. 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 2.

FAQs for 29 Woodside Drive, Hamilton, ON , Sherwood , Hamilton

What are the listing details for 29 Woodside Drive, Hamilton, ON?
29 Woodside Drive, Hamilton, ON is a Detached for sale in Hamilton, in the Sherwood neighbourhood, Hamilton. The current list price is $1,399,000. MLS number: X14171602.
How many bedrooms and bathrooms does this home have?
29 Woodside Drive, Hamilton, ON is listed as a Detached with a ["2-Storey"] style, featuring 5 bedroom(s) and 4 bathroom(s). The listed interior size range is 2500-3000 sq. ft..
What lot, basement, garage, or parking details are listed?
The lot size is listed as approximately 80.00 x 153.10 Feet. The basement is listed as: Full, Walk-Up, Separate Entrance, Finished. Garage type: Attached. Total parking: 6 space(s).
What heating, cooling, and exterior details are shown?
Heating is listed as: Gas, Forced Air. Cooling is listed as: Central Air. Exterior/construction materials are listed as: Brick, Vinyl Siding.
Where is this property located?
29 Woodside Drive, Hamilton, ON is located in the Sherwood neighbourhood of Hamilton. The listed cross street is High St..
What information is available on this public listing page?
The public listing page shows current active listing information, property photos, room details when available, map location, listed price, property features, and contact options. Annual taxes are listed as $9,422 / 2026. Valuation tools and similar sold-property previews are available after sign-in where applicable, without displaying sold data in this public FAQ.

FAQ content is based on current active listing fields shown on this page. Sold prices, sold comparables, and VOW-only details are not included in this public FAQ.