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$1,399,999Asking Price

138 Winona Drive, Toronto C02, ON M6G 3S7

Hillcrest, Toronto

Semi-Detached
3 + 1
Bedrooms
3
Baths
2
Parking
Day on Market

An extraordinary custom residence where elevated design and impeccable craftsmanship converge. Thoughtfully reimagined and fully renovated, this home embodies a level of sophistication rarely offered.The main level unfolds in a seamless open-concept design, curated for both grand entertaining and intimate everyday living. At its heart, a striking chef's kitchen showcases premium stainless steel appliances, an oversized statement island, and refined finishes, all overlooking the lush rear garden. Floor-to-ceiling patio doors create a dramatic indoor-outdoor experience, inviting natural light to pour in while offering effortless access to a private, serene backyard retreat.Upstairs, a tranquil sanctuary awaits. Three beautifully proportioned bedrooms are complemented by a spa-calibre bathroom, designed to evoke relaxation with elegant, timeless detailing. A conveniently located second-floor laundry adds a layer of modern practicality.The lower level continues the home's elevated aesthetic, offering a fully finished space with a separate rear entrance. Complete with a generous family room, a fourth bedroom, and a sleek full bath, it provides exceptional versatility for guests, extended family, or private quarters.An elegant electric fireplace and a cohesive palette of bespoke, high-end finishes throughout complete this remarkable home.A rare offering, 138 Winona Drive is a statement in refined living - where luxury, comfort, and design exist in perfect harmony.

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An extraordinary custom residence where elevated design and impeccable craftsmanship converge. Thoughtfully reimagined and fully renovated, this home embodies a level of sophistication rarely offered.The main level unfolds in a seamless open-concept design, curated for both grand entertaining and intimate everyday living. At its heart, a striking chef's kitchen showcases premium stainless steel appliances, an oversized statement island, and refined finishes, all overlooking the lush rear garden. Floor-to-ceiling patio doors create a dramatic indoor-outdoor experience, inviting natural light to pour in while offering effortless access to a private, serene backyard retreat.Upstairs, a tranquil sanctuary awaits. Three beautifully proportioned bedrooms are complemented by a spa-calibre bathroom, designed to evoke relaxation with elegant, timeless detailing. A conveniently located second-floor laundry adds a layer of modern practicality.The lower level continues the home's elevated aesthetic, offering a fully finished space with a separate rear entrance. Complete with a generous family room, a fourth bedroom, and a sleek full bath, it provides exceptional versatility for guests, extended family, or private quarters.An elegant electric fireplace and a cohesive palette of bespoke, high-end finishes throughout complete this remarkable home.A rare offering, 138 Winona Drive is a statement in refined living - where luxury, comfort, and design exist in perfect harmony.

Key Info

  • 2-Storey Semi-Detached
  • 2-Car Driveway
  • No Garage
  • Benson Avenue & Winona Dr
  • 1100-1500 Approximate Sq Feet
  • Finished Basement
  • 1 Kitchen
  • Forced Air Gas Heating
  • Central Air

Property

  • Lot Size 14.83 x 88.08 Feet
  • Brick Exterior
  • Taxes were $5,565 in 2025

Details

  • Fireplace
  • Family Room
  • Sewers
  • Municipal Water
  •  
  • MLS #C12898116
  • RIGHT AT HOME REALTY

Extras

Room Floor Dimensions Details
1 Kitchen Main 12.30' x 11.25' Centre Island, Stainless Steel Appliances, Quartz Counter
Washroom1 2-Piece Bathroom on Main Floor
Washroom1 5-Piece Bathroom
Washroom1 4-Piece Bathroom

Who lives here?

Hillcrest, Toronto is a central Toronto neighbourhood notable for its singles, renters, university grads, executives and education, law & public sector and arts & culture professionals. Residents tend to be older with a significant number of adults aged 25 to 49 and seniors aged 65 to 74.

Families

Kids Per Family

1.0

kids per family
in the neighbourhood.

Toronto  (1.2)
Gta  ({{ '1.29999995231628' | number: 1 }})

Singles

52% of residents are
single and loving it.

52% singles

Toronto (50%)
Gta ({{ '44.8800010681152' | number: 0 }}%)

Renters

52% of residents
are renters.

52% renters

Toronto (47%)
Gta ({{ '33.0200004577637' | number: 0 }}%)

Education

58% of residents are
university grads.

58% university grads

Toronto (48%)
Gta ({{ '43.6699981689453' | number: 0 }}%)

Income

Average Household Income

$143K

is the average household
income in the neighbourhood.

Toronto  ($132K)
Gta  ({{ '135056.828125' | minifiedCurrency }})

Professions

Professions

Government 15%
Sales 13%
Business 11%
Management 10%
Culture 7%

Immigrants

29% of residents were
born outside of Canada.

29% immigrants

Toronto (48%)
Gta ({{ '45.4300003051758' | number: 0 }}%)

Birthplace - All

Greece was once home to 3.3% of immigrants.
Philippines 3.0%
Caribbean 2.9%
Italy 2.2%
China 1.9%

3.3% from Greece
All-time

Birthplace - Recent

Philippines was once home to 1.0% of immigrants.
Other South America 0.4%
China 0.4%
USA 0.3%
Columbia 0.3%

1.0% from Philippines
Recent

Foreign Languages

Foreign Languages

Greek 4%
Italian 3%
Portuguese 3%
Spanish 3%
French 2%

Religions

Religions

Christian 49%
Jewish 10%
Buddhist 2%
Muslim 2%
Hindu 1%

Social Housing

Social Housing Buildings

3

Social housing buildings
in the neighbourhood.

Gta Avg (5.19)

Shelters

Shelters

4

Homeless shelters in
the neighbourhood.

Gta Avg (0.54)