Oakwood Village Homes with 100+ Approx Age

Oakwood Village Homes with 100+ Approx Age

Welcome to Oakwood Village, a hidden gem nestled in the heart of Toronto, Ontario. This vibrant neighborhood is a delightful blend of historic charm and modern convenience, making it an ideal place for families, young professionals, and retirees alike. Known for its tree-lined streets and a strong sense of community, Oakwood Village offers a warm and inviting atmosphere that truly feels like home.

One of the most captivating features of Oakwood Village is its rich architectural heritage. Many homes here boast an impressive age of 100 years or more, showcasing stunning craftsmanship and unique designs that tell a story of the past. From classic brick facades to intricate woodwork, these residences are a testament to the timeless beauty of early 20th-century architecture. Whether you’re strolling through the neighborhood or enjoying a cup of coffee on a porch, you can’t help but appreciate the character that these homes bring to the area.

Beyond the charming residences, Oakwood Village is also known for its vibrant local culture. The neighborhood is dotted with an array of boutique shops, cozy cafes, and diverse dining options, catering to every palate. Community parks and recreational facilities provide ample opportunities for outdoor activities, while the nearby subway station ensures easy access to the rest of Toronto.

In Oakwood Village, you’ll find not just a place to live, but a community to thrive in. Experience the perfect blend of history, culture, and convenience in this enchanting neighborhood—where your dream home awaits!

Newest Oakwood Village Homes with 100+ Approx Age

28 Conway Avenue, Toronto
$1,299,000
4 Beds ⋅ 3 Baths ⋅ C13865252 MLS
This is the one you have been waiting for. A stunning, renovated, detached 3+1 bed charmer just steps from the shops, cafes and restaurants of St. Clair West Village. All the original character is still here, but the old radiators are gone in favour of a gas furnace and central air conditioning, plus a main floor bathroom addition - three upgrades that are rare finds on these streets. Inside you will find real hardwood flooring, soaring 10' ceilings and thoughtful updates across 1,878 square feet of sun-filled living space. This highly coveted location features an extra deep lot with a private fenced yard, a detached garage off the laneway and zoning for a laneway home with room for 2-car parking and a generous suite above. The lower level has its own separate entrance and is set up as a one-bedroom apartment with a kitchen, bathroom, laundry and living room. Between the lower level and laneway zoning, 28 Conway offers 2 potential streams of additional income, or room for the whole family to grow. With a covered front porch, a 2-level deck off the kitchen and second floor rear bedroom, a stone patio and greenspace front & back, there is a ton of year-round outdoor enjoyment on offer rain or shine. Homes like this, in this neighbourhood, rarely come to market. Move right in with confidence. Pre-list home inspection available.

28 Conway Avenue, Toronto
44 Conway Avenue, Toronto
$980,000
3 Beds ⋅ 2 Baths ⋅ C13865220 MLS
Charming Detached Bungalow with Endless Potential in Vibrant Oakwood Village! *Welcome to this 3-bedroom, 2-washroom detached bungalow situated on an impressive 20 x 157-foot deep lot in Toronto's highly sought-after Oakwood Village. Offering a highly versatile floor plan, this property is perfect for families, urban professionals, and investors alike. Enjoy morning coffee on the wide, covered front verandah. Take advantage of the excellent layout flexibility provided by both a convenient side entrance and a separate rear entrance with an enclosed staircase leading straight to the basement from the rear garden.The outdoor space is a rare urban oasis. The massive, fully fenced backyard boasts a large patio area sheltered by a professionally built metal pergola-complete with several mature grape vines-along with a separate, dedicated fenced area for your dogs.At the rear of the deep lot, a major highlight awaits: an oversized, double car garage equipped with a bright, closed workshop, wide storage loft, and its own dedicated hydro panel, opening onto a wide public lane with several newly built laneway suites down the block! **Wonderful Location & Community! Nestled just a short walk from both Oakwood Ave and St. Clair Ave West, you are steps from cherished community hubs like the Nia Centre for the Arts, the Ontario School of Ballet, and the Oakwood Village Library and Arts Centre. The neighborhood is packed with family-run restaurants, independent bakeries, cozy cafes, and specialty shops. Commuting is effortless with quick access to Highway 401 via the Allen Road Expressway, nearby TTC transit routes, excellent local school options, and mature green spaces.A 1987 Land Survey and a recent Pre-Listing Home Inspection are available on file.

44 Conway Avenue, Toronto
167 Westmount Avenue, Toronto
$1,125,000
3 Beds ⋅ 3 Baths ⋅ C13861920 MLS
Updated, well maintained, detached house, a Duplex + basement unit, in superbe location. For investors: all units are occupied by great tenants, who would be happy to stay. This house can also be perfect as a multi-generational home, or for an end-user to live-in & have rental income. Quiet street, steps to the most vibrant part of Corso Italia with plenty of shops and cafés on St Clair West, excellent TTC access. walking distance to Wychwood barns, parks and Metrolinx new line on Eglinton. All units have been updated, ground & upper floors have their own washer/dryer & window units AC. Central heating is gas, radiant. 2 legal front pad parkings. 1333 sqft above ground, 642 bsmt, lot 25 x 119ft. Duplex + bsmt unit, renovated & tenanted, 1 lease until April 2027. Seller, agent do not warrant retrofit of bsmt. Fl plans, Financials, Inspection, Upgrades att. Some photos are before tenancy.

167 Westmount Avenue, Toronto
303 Oakwood Avenue, Toronto
$1,069,000
5 Beds ⋅ 3 Baths ⋅ C13831764 MLS
Semi-Detached In One Of Toronto's Great Neighbourhoods, Fronting across from park Park. Clear View. Bus At Front Steps, 3 Spacious Units, With A Great Layout And Independent Access, 3 Kitchen, Large Front Porch, Large Garage, Permit Parking On Street. Don't Miss The Opportunity To See This Great House.

303 Oakwood Avenue, Toronto
61 Appleton Avenue, Toronto
$1,399,000
5 Beds ⋅ 4 Baths ⋅ C13824332 MLS
61 Appleton is a meticulously updated, move-in-ready semi-detached 3-storey home in the family-friendly Oakwood-Vaughan neighbourhood! This versatile 4+1 bed, 4 bath home offers 2,227 sq ft above grade plus 780 sq ft below, living beautifully as a spacious four-level family residence, or add a single wall on the main floor to convert it into a low-maintenance three-unit dwelling, complete with three full kitchens already in place. The professionally finished lower level offers its own separate entrance, kitchenette, above-grade windows, and a full 3-piece bath, making it ideal for an in-law or nanny suite. Enter through the enclosed, insulated porch/mud room into a bright main floor featuring a solid wood staircase, bay-windowed living room, and a dining room with a coffered ceiling and French doors. The chef's kitchen boasts custom solid wood cabinetry, quartz counters, a stainless appliance package with a gooseneck faucet and built-in garbage disposal, plus a walk-out to the backyard. The second floor offers a full second kitchen, a generous primary suite, second bedroom, home office, powder room with in-suite laundry, and a private balcony with BBQ gas line. A vaulted third-floor loft with built-in storage completes the upper levels, flexible as a primary retreat, teen space, or studio. Extensive mechanical upgrades throughout: high-efficiency Bosch hybrid boiler, four wall-mounted A/C units, copper plumbing with 15 drains, backflow preventer, 200-amp service with surge protection, and a wired smoke/CO system. 3/4 Solid oak hardwood runs throughout, and two laundry stations offer everyday convenience. Outside, enjoy a cedar-covered deck, fully fenced private yard, garden shed, and parking for 2 via mutual drive. Steps to the St Clair streetcar, cafes, restaurants, and top-rated schools, including Oakwood Collegiate and York Memorial.

61 Appleton Avenue, Toronto
815 St Clair Avenue W, Toronto
$299,000
2 Baths ⋅ C13547578 MLS
Don't miss this opportunity to own a well-known restaurant in a densely populated, high-traffic location surrounded by thriving residential and commercial developments. This turnkey operation features a fully equipped kitchen, dine-in area, and efficient take-out setup, making it ideal for both experienced restaurateurs and first-time owner-operators. Known and loved by the local community, the restaurant offers a warm and inviting atmosphere, a loyal customer base, and a strong brand recognition. With low overhead costs, low rent, attractive lease terms, and excellent growth opportunities through catering, extended hours, or delivery expansion, this business offers outstanding value and long-term earnings potential.

815 St Clair Avenue W, Toronto
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