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165 Winona Drive in Toronto: Wychwood House for sale (Toronto C02) : MLS®# C13751354
165 Winona Drive WychwoodTorontoM6G 3T1
OPEN HOUSE: Sep 12, 2026
02:00 PM
-
04:00 PM
EDT
Open House on Saturday, September 12, 2026 2:00PM - 4:00PM
A Rare Gem In The City With A "Private Driveway & Garage-Truly Exceptional!" This Solid-Brick Home Features 3+1 Bedrooms & 3 Bathrooms, Complemented By Hardwood Flooring Throughout. The Desirable 9Ft Flat Ceiling (on main), West-Facing Exposure Fills The Home w/an Abundance Of Natural Light, Creating A Warm Welcoming Atmosphere. Extensively Renovated From Top To Bottom w/ $$$ Spent, The Home Showcases Numerous Upgrades, Including Newer Windows, Doors, Flooring, Stairs, Bathrooms, Kitchen, Gas Range/Oven, All Appliances, Radiant Heating, Heat Pump, Crown Mouldings, Front Entrance Stairs & Much More. Enjoy Precious Family Moments In The Private Fully Fenced Backyard. Additional Updates Include An Upgraded Copper Electrical Panel & A Basement Equipped w/A Sump Pump, Providing Added Comfort & Peace of Mind. Move-In Ready And Meticulously Updated For The Pride Of Ownership. Don't Miss This Rare Opportunity To Own A Beautiful Home Offering The Perfect Blend Of City Convenience, Privacy And Comfort!More details
Welcome to 59 Galloway Road, a spacious detached home set on an exceptional 45 x 208 ft lot, a rare find in Toronto offering incredible space, privacy and flexibility. Step into the backyard and it is easy to see what makes this property so special. Surrounded by mature trees and lush gardens, this expansive yard feels like a private retreat from the city. Enjoy summer barbecues under the awning, relaxing beneath the gazebo, gardening, entertaining or simply the peace and privacy of your own outdoor oasis. Inside, this spacious 5 level back-split offers 4 + 2 bedrooms, 4 bathrooms and multiple living areas, ideal for a growing family, multigenerational living, guests, home offices or potential additional income. The bright main living and dining areas offer plenty of space for everyday living and entertaining. The updated eat in kitchen features granite countertops, a distinctive brick accent wall and a walkout overlooking the spectacular backyard. The inviting family room features a gas fireplace and direct access to the backyard, gardens and gazebo. Upstairs, the spacious primary bedroom offers its own ensuite bathroom and private balcony. The finished lower levels provide even more flexibility with additional bedrooms, recreation and living areas, a second kitchen and separate entrance with walkout, ideal for extended family or a potential income generating suite. Numerous improvements include updated flooring and lighting throughout, an additional backsplit window for more natural light, 200 amp electrical service (future proofed for a hot tub or EV charger) & high efficiency Lennox A/C. An attached double garage and private driveway provide plenty of parking. Located in beautiful Guildwood, enjoy mature trees, parks, ravines, waterfront trails, Lake Ontario and convenient access to Guildwood GO Station and 20 mins to downtown Union Station. A rare extra deep lot. an incredible backyard & a spacious and flexible home... Welcome home!More details
Big home, big lot and a great South Etobicoke location. Welcome to 102 Judson Street, offering over 3,000 sq. ft. of above-grade living space on a 50 x 120 ft corner lot. With 5 bedrooms and 4 bathrooms, including a bedroom conveniently located on the main floor, there's plenty of space and flexibility for a large or growing family. Outside, you'll find a private yard, carport and plenty of parking, with lots of room for family and guests. The location makes getting around easy. You're close to Mimico GO Station and Mimico Village, with quick access to the Gardiner Expressway, QEW and Highway 427, making the commute to Downtown Toronto or around the GTA convenient. Shops, restaurants, parks and the Lake Ontario waterfront are also nearby.With its size, large lot and convenient location, 102 Judson offers plenty of possibilities. Move in, renovate over time, or bring your own ideas and make it yours.More details
Muskoka in the City! A rare urban retreat in the heart of Etobicoke. This beautifully renovated bungalow combines modern living, incredible versatility and exceptional income potential. The main level offers beautifully kitchen combined with the Breakfast area. Living room overlooks the front porch/deck and 3 bedrooms & 2 full baths, while the finished lower level features 2 additional bedrooms, 2 baths, a second kitchen, guest kitchenette & separate side entrance-perfect for extended family or flexible living arrangements. Walk out from the primary bedroom to a two-level deck overlooking a private backyard that opens directly onto expansive green space-your own peaceful escape without leaving the city. Parking for 6+ cars plus a detached 1 car garage. Conveniently located near Mimico GO, TTC, major highways, shopping, dining, Starbucks & Tim Hortons. Renovated, versatile and ideally connected-city living with a cottage-country feel!More details
Davisville Village Beauty! Beautifully updated 3-bedroom, 3-bath semi on a fabulous 23' x 100' lot, offering a rare combination for Midtown living: main-floor powder room, private south-facing backyard, double-car garage + 2 driveway parking spaces! Bright and spacious with the feel of a detached home. The main floor features a gracious living room with fireplace & built-ins, large dining room, family-sized kitchen and convenient powder room. Upstairs offers 3 bedrooms, including an spacious primary with large closet and adjoining sitting room - perfect for a home office or quiet retreat. The finished lower level adds valuable living space with a rec room, laundry and 3-pc bath. Step outside to a large deck, patio and beautifully landscaped private garden-ideal for relaxing, entertaining or family time. Furnace & A/C replaced in 2024. Steps to Bayview shops, restaurants & cafés, Maurice Cody P.S., TTC, with easy access to Bayview Extension, DVP & downtown. A rare blend of space, comfort, parking and outdoor living in one of Midtown's most desirable family neighbourhoods. Open House: Sat & Sun, 2-4 PM.More details
Stop the Search-This May Be the Best Value in Baby Point!Detached on exclusive Humbercrest Boulevard. At this price? Yes, you read that correctly. Take a moment to pick yourself up off the floor-Step inside to a bright, open-concept main floor with beautiful wood floors and an incredibly functional layout. There's room for a proper dining table, a comfortable TV area and a relaxed sitting lounge-plenty of space to entertain or simply enjoy family life.The open-concept kitchen is made for entertaining, featuring a breakfast bar and wrap-around counter space that gives you plenty of room to prep dinner while friends gather around with a glass of wine. Just off the kitchen, the spacious mudroom offers fantastic built-in storage and an easy connection to the backyard. Upstairs, you'll find three generously sized bedrooms and a stylish four-piece bathroom. A skylight floods the second floor with natural light, while the excellent bedroom sizes, closets and windows make this the perfect level for a growing family. And then there's the basement - the possibilities are endless! Use the space as a fantastic family room, playroom or hangout for the kids. Or keep the existing kitchen and bathroom and create an in-law, nanny or guest suite. It's a flexible space that can adapt as your family and needs change.With a new roof, eaves, siding, wall-mounted A/C/Heat Pump, windows and more, there's plenty already taken care of, allowing you to move in and enjoy.The lot is where this home really shines. A beautiful rear deck, two sheds, mature trees, grass and plenty of room for the kids to play - plus parking galore. This is the kind of backyard that gives you space to actually enjoy your home.Why squeeze into a semi or townhouse when you can own a detached home on one of Baby Point's most coveted streets?Humbercrest. Detached. Great lot. Incredible flexibility. An absolutely fantastic value.Don't miss your chance to move into Baby Point and make this exceptional property your ownMore details
Custom-built in 2018 on an extraordinary 57 x 297 ft lot spanning approximately 0.39 acres, this exceptional residence offers over 5,100 sq ft of finished living space with a rare combination of luxury, privacy, and long-term versatility. Offering approximately 3,426 sq ft above grade plus a 1,680 sq ft finished walk-up lower level, the home features 9 ft ceilings on the main floor, nearly 9 ft ceilings in the basement, and 8.5 ft ceilings on the upper level. The separate walk-up lower level offers excellent flexibility for extended family living or future income potential. Elegant finishes include large-format polished porcelain tile throughout the principal areas, rich white oak hardwood flooring throughout the living spaces and bedrooms, pot lights throughout the interior and exterior, and custom wrought iron railings across the staircase, patio, primary balcony, and second bedroom terrace. The spacious kitchen opens seamlessly into the main dining and family room overlooking the backyard. An electric fireplace adds warmth and character to the family room. The upper level features exceptionally large bedroom spaces, including oversized primary and secondary bedrooms with the potential to create additional bedrooms, office space, nursery areas, or custom dressing rooms if desired.The spa-inspired primary ensuite features oversized porcelain tile, dual floating vanities, a freestanding soaker tub, oversized glass shower with rainfall head, lighting, and custom mosaic accents throughout. The finished lower level showcases natural travertine flooring with heated floors throughout nearly the entire basement. Additional features include a durable metal roof installed in 2018, floating vanities throughout the bathrooms, and parking for up to 4 vehicles. A rare opportunity to own a newer custom-built home on an ultra-deep premium lot.More details
Welcome to 29 Denison Ave! This rare opportunity in the heart of downtown Toronto delivers style, space and incredible versatility just steps from Queen West and Kensington Market. Currently configured as two separate units, this beautifully updated home offers the flexibility to generate rental income, accommodate multi-generational living, or transform it into a spectacular single-family residence.The main suite is designed to impress, featuring two spacious bedrooms, two bathrooms and a stunning custom kitchen equipped with high-end Bertazzoni gas range and stainless steel appliances. The showpiece rear addition boasts soaring vaulted ceilings and skylights, filling the space with natural light and creating the perfect setting for everyday living and entertaining. Extra comfort with the heated floors in the kitchen/living room and lower level. Built-in speakers elevate the experience, while the private backyard deck offers the perfect place to unwind with views of the CN Tower. The underpinned lower level adds an impressive amount of functional living space, with enhanced ceiling height and flood protection. Complete with a 4-piece bathroom featuring an oversized shower, custom closet space, stacked laundry and a generous living area with bar, this level offers incredible flexibility as a primary retreat, family room, guest suite or additional entertaining space. Upstairs, a fully self-contained one-bedroom apartment features a large bedroom with city views, spacious living and dining areas, in-suite laundry and an updated kitchen with gas stove and full-size appliances. The generous layout also provides potential to create additional bedrooms. Exceptionally rare downtown feature: a detached 2-car garage offering both secure parking and additional storage! All of this in one of Toronto's most sought-after pockets, surrounded by some of the best restaurants, cafés and shops of Queen West and Kensington Market. This is downtown living at its best!More details
Freshly Updated. Move-In Ready. 165 Feet Of Possibility For Tomorrow.Set On An Exceptional 25 X 165 Ft South-Facing Lot In Coveted North Toronto, This Detached Bungalow Offers A Rare Combination Of Immediate Comfort, Valuable Recent Improvements And Remarkable Long-Term Potential.Featuring 2+2 Bedrooms, 2 Bathrooms And A Finished Basement With A Separate Entrance, The Home Has Been Freshly Painted And Enhanced With New Premium Waterproof SPC Luxury Vinyl Plank Flooring With A 20-Mil Commercial-Grade Wear Layer, Bringing A Clean, Contemporary Feel And Exceptional Everyday Durability.A Particularly Valuable Recent Improvement Is The Upgraded 200-Amp Electrical Service, Increased From The Previous 100-Amp Service, Providing Substantially Greater Electrical Capacity for today's needs and future possibilities. An Owned Tankless Water Heater adds further convenience and value, with no hot-water-tank rental to assume.Move In And Enjoy Today, Personalize Over Time, Expand The Existing Home, Or Explore The Possibility Of Building New. Steps To Avenue Rd And Minutes To Yonge St, With Excellent Schools, Parks, Transit, Dining, Shopping And Everyday Amenities Close At Hand.For An End User, A Fresh And Comfortable Home. For A Builder, An Extraordinary Canvas. For An Investor, A Rare 165-Ft-Deep Piece Of Toronto Land With Enduring Potential.Ready For Today. Powered For Tomorrow. 165 Feet Of Possibility.Basement photos are virtually staged.More details
Nestled in the heart of Long Branch, just one block from Lake Ontario, this charming Tudor Revival home blends timeless character with exceptional versatility. Built in 1941, it showcases beautiful original details including leaded glass windows, hardwood flooring, rich wood trim, and a classic wood-burning fireplace.Currently configured as three self-contained living spaces, this unique property offers outstanding flexibility for investors, multigenerational families, or homeowners seeking supplemental income.The main floor features two bedrooms, a spacious kitchen, combined living and dining room, renovated bathroom (2023), separate laundry, and direct access to the backyard and rear deck. Recently renovated lower level includes a separate entrance, full kitchen, large bedroom, new bathroom, oversized utility/laundry room, and extensive updates throughout.The upper-level is currently configured as a separate suite with a kitchenette (could be converted to mudroom or den), generous bedroom, large living room (would serves as the primary bedroom if converting to a single family home), walk-in closet, spa-inspired bathroom, and private balcony (2005) 200 AMP Service. For those seeking a single-family home, the layout can be easily reconfigured to suit a variety of needs.Set on an impressive 50 x 150 ft lot, the fully fenced backyard features two new stone patios (2025), a new 6-foot privacy fence (2025), and a spacious deck ideal for entertaining. A circular driveway accommodates up to four vehicles and is complemented by an attached garage.Additional updates include a new roof (2021), waterproofing improvements, and numerous interior and exterior enhancements. The upper-level addition was completed in the early 2000s.A rare opportunity to own a distinctive property offering character, flexibility, income potential, and exceptional outdoor space in one of South Etobicoke's most desirable lakeside communities. Carson and Dunlop Home Inspection available upon request.More details
An outstanding opportunity to acquire a turnkey property with 4 self-contained units in the highly sought-after High Park North neighbourhood, just steps from Dundas West TTC Station. 61 Chelsea Ave has been lovingly maintained by an experienced owner, offering both stability and long-term investment appeal. Recent upgrades include vinyl flooring throughout, 200 Amp electrical panel, new furnace, AC and tankless water heaters (2), new bathrooms and kitchens, new composite decks (3), garbage pad, front and back walkways and patio, fencing, interior waterproofing, and most appliances. Current rents are at market level and investors benefit from a **strong cap rate of 4.92%**, with minimal need for repositioning.Tenants benefit from efficient floorplans and exceptional convenience, with Dundas West Subway Station just a 5-minute walk away and the UP Express only a 7-minute walk away, allowing for quick access to both downtown and Pearson Airport. The property is also just minutes from High Park, offering expansive green space, trails, and recreational amenities.Located near the vibrant Roncesvalles Village, residents enjoy easy access to some of the city's best cafes, restaurants, and boutique shops-enhancing the overall lifestyle appeal and supporting strong rental demand.A turnkey asset in a premier location, 61 Chelsea Ave presents a compelling opportunity for investors seeking stable income, strong fundamentals, and enduring rental demand in one of Toronto's most desirable communities.More details
Welcome to 92 Gradwell Dr - a beautifully updated detached home that blends timeless character with modern comfort in Cliffcrest, one of the east ends most sought after neighbourhoods. Set on a large 45 x 136 lot, this spacious 4+1 bedroom, 4 bathroom home offers the kind of layout and outdoor space that's getting harder and harder to find in the city. Inside, you'll find bright, thoughtfully designed living spaces with an easy flow that works just as well for everyday family life as it does for entertaining. Upstairs features four well-sized bedrooms, including a primary retreat with walk in closet and ensuite, while the finished basement adds even more flexibility with a fifth bedroom (or home office), additional living space, room for guests, or the perfect kids play area. Out back, the private yard leads to an oversized 2-car detached garage complete with heat and power - ideal for car enthusiasts, a workshop, studio space, or simply the ultimate storage setup. A rare combination of space, function, and understated luxury in a fantastic family-friendly neighbourhood close to parks, schools, transit, and the waterfront. This is the kind of home you move into and stay for years.More details
Data was last updated September 8, 2026 at 06:15 AM (UTC)
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