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NEXT Open House + more
Jan 17, 2026 02:00 PM - 04:00 PM EST

373 Gilpin Drive
Woodland Hill Newmarket L3X 3H2

$1,395,888
Residential Freehold beds: 5 baths: 5.0

373 Gilpin Drive
Photo 1: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 2: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 3: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 4: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 5: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 6: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 7: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 8: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 9: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 10: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 11: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 12: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 13: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 14: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 15: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 16: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 17: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 18: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 19: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 20: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 21: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 22: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 23: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 24: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 25: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 26: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 27: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 28: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 29: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 30: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 31: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 32: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 33: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 34: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 35: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 36: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 37: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 38: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 39: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 40: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 41: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 42: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 43: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 44: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 45: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 46: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 47: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 48: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 49: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Photo 50: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
Open House - Jan 17, 2026
02:00 PM - 04:00 PM EST
NOTES: Open House on Saturday, January 17, 2026 2:00PM - 4:00PM
Open House - Jan 18, 2026
02:00 PM - 04:00 PM EST
NOTES: Open House on Sunday, January 18, 2026 2:00PM - 4:00PM
Status:
Active
Prop. Type:
Residential Freehold
MLS® Num:
N12695156
Bedrooms:
5
Bathrooms:
5
***Your Ravine Lifestyle Awaits*** Set on one of Woodland Hills' most desirable streets, this exceptional custom-built residence offers a rare opportunity to own a premium 50-foot wooded ravine lot backing directly onto the protected trails and natural beauty of Environmental Park. With well over 3,000 square feet of finished living space and close to $160,000 in upgrades, this home delivers a remarkable blend of scale, craftsmanship, and lifestyle in a setting that feels both private and inspiring. The arrival is both welcoming and refined, with six-car asphalt driveway and an elegant interlock walkway. Inside the 9-foot ceilings, crown moulding, and classic wainscoting establish a sense of timeless quality, while distinctive multi-level design creates a thoughtful balance between open gathering spaces and well-defined principal rooms, making it ideally suited for larger or multi-generational families. At the heart of the home, the beautifully refreshed open-concept kitchen includes quartz countertops, and quality stainless steel appliances complemented by a dramatic picture window allowing the beauty of the forest to become part of everyday living as the seasons change. The versatility of this residence continues with two primary suites and an abundance of principal rooms that adapt effortlessly to evolving family needs and can easily provide 5-bedroom residence. The private backyard retreat features a tiered deck, covered porch, and fire pit, creating an inviting outdoor sanctuary surrounded by mature trees and natural privacy. The property opens onto miles of scenic walking, biking, and hiking trails, offering a true connection to nature. Only minutes to shopping and dining at Upper Canada Mall, GO Train station, VIVA transit, and is centrally located between Highways 404 & 400!This is more than a home - it is a lifestyle defined by space, convenience, and a deep connection to nature, offered on an irreplaceable ravine lot in the heart of Woodland Hills.
Property Type:
Residential Freehold
Property Sub Type:
Detached
Home Style:
2-Storey
Total Approx Floor Area:
3000-3500
Lot Size:
<.50
Lot Depth:
89'8"
Lot Frontage:
50'
Direction Faces:
West
Bedrooms:
5
Bathrooms:
5.0
Water supply:
Municipal
Kitchens:
1
Bedrooms Above Grade:
5
Kitchens Above Grade:
1
Rooms Above Grade:
10
Rooms Below Grade:
1
Zoning:
Freehold Residential
Heating type:
Forced Air
Heating Fuel:
Gas
Fireplaces:
1
Foundation:
Concrete
Roof:
Asphalt Shingle
Basement:
Finished with Walk-Out, Separate Entrance
Fireplace Features:
Natural Gas
Fireplace/Stove:
Yes
Garage:
Attached
Garage Spaces:
2.0
Other Structures:
Sauna
Parking Features:
Private
Parking Spaces:
6
Total Parking Spaces:
8.0
Family Room:
Yes
Possession Details:
TBD
Lot Irregularities:
Irregular
Pool:
None
Link:
No
HST Applicable To Sale Price:
Included In
Taxes:
$7,044.03 / 2025
Assessment:
$- / -
York
Newmarket
Woodland Hill
Fenced Yard, Hospital, Park, Public Transit, Ravine, School Bus Route
Sauna
Hot Water Tank
All Existing Stainless Steel Appliances: Samsung French Door Fridge, Bosh Built-In Dishwasher, Danby Wine Fridge, GE Flat Top Stove, Samsung Over the Range Microwave, White GE Washer and Dryer, All Window Coverings, All Electrical Light Fixtures, Indoor Wet Built-In Sauna, Garage Door Openers with Remotes, Furnace, Nfilsk Central Vac and all related attachments, Water Softener, AC.
Hot Tub, TVs, Patio Furniture
Water Heater
Brick
Floor
Type
Size
Other
Main
Kitchen
14' × 13'7"
Ceramic Floor, Breakfast Bar, Quartz Counter
Main
Breakfast
10' × 9'11"
Ceramic Floor, Combined w/Kitchen, Overlooks Backyard
Main
Living Room
13'7" × 11'11"
Hardwood Floor, Combined w/Dining, Coffered Ceiling(s)
Main
Dining Room
13'7" × 8'4¾"
Hardwood Floor, Combined w/Living
Second
Primary Bedroom
14'10" × 12'6"
French Doors, 5 Pc Ensuite, Walk-In Closet(s)
Second
Bedroom 2
13'10½" × 11'7¾"
Laminate, 3 Pc Ensuite, Walk-In Closet(s)
Second
Bedroom 3
14'8" × 12'5"
Laminate, 4 Pc Bath, Closet
Second
Bedroom 4
13'7" × 10'5"
Laminate, Double Closet, Window
Lower
Family Room
20'4½" × 13'8"
Hardwood Floor, Gas Fireplace, W/O To Deck
Lower
Bedroom
21'3" × 13'
Broadloom, Window
Lower
Laundry
13'1" × 7'10⅞"
Ceramic Floor, Laundry Sink, B/I Shelves
Basement
Recreation
30'10" × 18'5"
Broadloom, Walk-Out, Ceiling Fan(s)
UFFI:
No
Utilities Cable:
Yes
Utilities Telephone:
Yes
Utilities Gas:
Yes
Utilities Hydro:
Yes
Utilities Water:
Yes
Sewers:
Yes
Special Designation:
Unknown
Sewers:
Sewer
Air Conditioning:
Central Air
Central Vacuum:
No
Seller Property Info Statement:
No
Laundry Level:
Lower Level
Date Listed:
Jan 14, 2026
Original Price:
Previous Price:
  • Photo 1: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    373 Gilpin Drive
  • Photo 2: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Foyer
  • Photo 3: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    2 Pc Bathroom
  • Photo 4: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    2 Pc Bathroom
  • Photo 5: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Dining Room
  • Photo 6: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Living/ Dining Room
  • Photo 7: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Kitchen
  • Photo 8: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Kitchen
  • Photo 9: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Kitchen
  • Photo 10: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Kitchen
  • Photo 11: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Kitchen
  • Photo 12: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Breakfast / Kitchen
  • Photo 13: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Primary Guest Room
  • Photo 14: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Primary Guest Room
  • Photo 15: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    3 Pc Bathroom
  • Photo 16: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    3 Pc Bathroom
  • Photo 17: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Primary Bedroom
  • Photo 18: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Primary Bedroom
  • Photo 19: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Primary Bedroom
  • Photo 20: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    5 Pc Ensuite in Primary Bedroom
  • Photo 21: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    5 Pc Ensuite in Primary Bedroom
  • Photo 22: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Bedroom 3 / Office
  • Photo 23: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    4 Pc Bathroom
  • Photo 24: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    4 Pc Bathroom
  • Photo 25: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Bedroom 4
  • Photo 26: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Bedroom 4
  • Photo 27: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Family Room
  • Photo 28: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Family Room With Gas Fireplace
  • Photo 29: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Wet Sauna With 3 Pc Bathroom
  • Photo 30: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Wet Sauna (Steam Room)
  • Photo 31: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Laundry
  • Photo 32: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Bedroom 5 / Gym
  • Photo 33: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Rec Room
  • Photo 34: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Rec Room Walk-Out To Backyard
  • Photo 35: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Back of the house
  • Photo 36: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Backyard
  • Photo 37: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Top Deck Overlooking Ravine
  • Photo 38: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Top Deck Overlooking Ravine
  • Photo 39: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Backyard With Firepit
  • Photo 40: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Park Entrance at the back of the house
  • Photo 41: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Park at the back of the house
  • Photo 42: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Back of the house from the Park
  • Photo 43: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Summer picture of the backyard
  • Photo 44: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Summer picture of the backyard
  • Photo 45: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Lower Deck in summer
  • Photo 46: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Top Deck In Summer
  • Photo 47: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Patio at Night
  • Photo 48: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Backyard at Night
  • Photo 49: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Backyard at Night
  • Photo 50: 373 Gilpin Drive in Newmarket: Woodland Hill House for sale : MLS®# N12695156
    Twilight View of the house

Virtual Tour

Listed by ROYAL LEPAGE YOUR COMMUNITY REALTY
Data was last updated January 14, 2026 at 07:15 PM (UTC)
Area Statistics
Listings on market:
14
Avg list price:
$1,183,500
Min list price:
$999,000
Max list price:
$1,498,000
Avg days on market:
9
Min days on market:
3
Max days on market:
70
These statistics are generated based on the current listing's property type and located in Woodland Hill. Average values are derived using median calculations. This data is not produced by the MLS® system.
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.