Oshawa Homes with 100+ Approx Age

Turnkey has never had this much personality! Extensively renovated from top to bottom, inside and out with an artistic eye, this distinctive 2.5-storey home combines significant upgrades with character, craftsmanship and unexpected details at every turn. Offering 3 bedrooms, 3 bathrooms and beautifully finished living space on every level, this home is anything but cookie-cutter.The main floor welcomes you with warm wood flooring, pot lights and a beautiful coffered ceiling in the living room. At the heart of the home is a generous custom kitchen, where a striking onyx backsplash adds a touch of elegance and a chalkboard wall brings a playful dose of personality. The second floor features two bedrooms and a beautifully finished 5-piece bathroom with double sinks and a custom shower. Continue upstairs to the home's true showstopper: a sun-filled loft-style primary bedroom. Three windows, pot lights and a generous layout create a bright, private retreat with plenty of room for a sitting area, dressing space or office nook. The newly finished basement (2026) adds even more living space and vintage charm with a beautiful clawfoot tub. Extensive updates include new electrical, plumbing and pot lights(2019), as well as a new front porch and flooring (2026), plus a durable metal roof. Outside, lush gardens and stamped concrete create a charming, low-maintenance outdoor setting, while a barn-style storage shed has been playfully transformed into the home's own "General Store," complete with its own electrical panel. From the coffered ceiling and onyx backsplash to the chalkboard wall, sun-drenched loft, clawfoot tub and General Store out back, this is a home where thoughtful renovation meets artistic expression. Warm, creative and anything but ordinary, this is a home with a little more soul.

27 Rowe Street, Oshawa

$599,900

4 Beds ⋅ 2 Baths ⋅ E13733472 MLS

Welcome to 97 Adelaide Avenue East in Oshawa. This very well-maintained legal duplex is found in a convenient Oshawa location in the O'Neill area. This property features two clean, nicely appointed two-bedroom units, making it an excellent opportunity for investors, multi-generational living, or buyers looking to offset their mortgage with rental income. Each unit boasts its own laundry, fully equipped kitchen, four piece bathroom, private yard, outdoor shed, and ample parking. Both units offer comfortable layouts and functional living spaces, with a clean and inviting presentation throughout. The property is ideally situated close to public transit, Lakeridge Health, downtown Oshawa, O'Neill High School, the Oshawa Golf & Curling Club, and a variety of shopping and everyday amenities. With a legal duplex designation and a desirable location, this property offers excellent flexibility and long-term potential. A great opportunity to own a well-kept income property in an established Oshawa neighbourhood.

97 Adelaide Avenue E Unit East, Oshawa

$540,000

2 Beds ⋅ 2 Baths ⋅ E13732830 MLS

The Ideal Home For A First-Time Buyer Or Investor. Semi-Detached 2 Bed 2 Bath Laid Out Perfectly. Large Open Concept Main Floor Providing A Spacious Living And Dining Room. The Kitchen Has A Walkout To The Side Of The Home Where The Parking Pad Is. A Breakfast Bar Provides Convenience With A Pass Through To Dining Room. 2nd Floor Has A 4 Piece Bath And Main Floor Has A Powder Room. Close To The University, Parkwood Estate, Downtown, Schools, Parks,Transport.AC AND FURNACE OWNED ONLY WATER HEATER RENTAL $42/MONTH.

13 Brock Street E, Oshawa

$434,990

3 Beds ⋅ 3 Baths ⋅ E13720064 MLS

This home has been fully renovated with 3 bedrooms and 3 full bathrooms. And a private second-floor rooftop terrace. The property is move-in ready and conveniently located near schools, parks, shopping, transit and more! Great for 1st time homebuyers and/or investors.

11 MAPLE Street, Oshawa

$819,999

3 Beds ⋅ 2 Baths ⋅ E13718674 MLS

Welcome to 559 Masson Street for a rare opportunity to own a beautifully updated century home on one of Oshawa's most coveted and picturesque streets. Full of character, charm, and timeless appeal, this exceptional residence perfectly blends the craftsmanship of a bygone era with a large main-level extension for a desirable modern living space. Nestled in a highly sought-after family-friendly neighbourhood, this home is located close to top-rated schools including Dr S.J. Phillips Public School, O'Neill C.V.I. and just minutes from Lakeridge Health Oshawa, one of the region's leading hospitals. Lovingly maintained and extensively upgraded, this remarkable home boasts over $100,000 in renovations, including a stunning new kitchen with whirlpool stainless steel appliances (incl. gas range) and gorgeous granite countertops. Elegant coffered ceilings that add warmth, style, and architectural distinction, and a brand new welcoming front porch to enjoy your evenings. Step out back and discover your own private retreat, complete with a beautiful in-ground swimming pool - perfect for entertaining, relaxing, and creating unforgettable summer memories with family and friends. The mature surroundings and tree-lined street create an atmosphere of tranquility and prestige that is increasingly difficult to find. Rich in history yet thoughtfully updated, 559 Masson Street offers a rare combination of character, comfort, and location. Whether you are drawn to the home's century-old charm, its impressive upgrades, or its prime setting in one of Oshawa's most desirable neighbourhoods, this is a property that truly stands apart.

559 Masson Street, Oshawa

$999,900

4 Beds ⋅ E13692308 MLS

Legal Four Plex 2 Story built in 1910 on a quite street, the property has a large back yard with lots of driveway and parking one spot for each apartment plus some extra. The property has four one bedroom apartments all very similar in size and layout. The basement is split into 2 sections the back section is laundry and has 2 washers and 2 coin dryers. All units are currently rented one at $1325 plus Hydro this tenant takes care of the yard maintenance, one rented at $1500 Monthly plus hydro and 2 rented at $1525 plus hydro all of the tenants would like to stay. The property shows very well all units only one may not in excellent shape. The tenants are excellent tenants always pay on time and keep the units looking really good. The property backs onto the development underway to the north, which is the vacant parcel that starts at Adelaide Road and Ritson Road and goes south and east. 278 William is being sold as well and listed at $684,900.00 the two properties combined are almost an half an acre.

292 William Street E, Oshawa

$999,900

4 Beds ⋅ 4 Baths ⋅ E13690834 MLS

Legal Four Plex 2 Story built in 1910 on a quite street, the property has a large back yard with lots of driveway and parking one spot for each apartment plus some extra. The property has four one bedroom apartments all very similar in size and layout. The basement is split into 2 sections the back section is laundry and has 2 washers and 2 coin dryers. All units are currently rented one at $1325 plus Hydro this tenant takes care of the yard maintenance, one rented at $1500 Monthly plus hydro and 2 rented at $1525 plus hydro all of the tenants would like to stay. The property shows very well all units only one may not in excellent shape. The tenants are excellent tenants always pay on time and keep the units looking really good. The property backs onto the development underway to the north, which is the vacant parcel that starts at Adelaide Road and Ritson Road and goes south and east. 278 William is being sold as well and listed at $684,900.00 the two properties combined are almost an half an acre.

292 William Street E, Oshawa

$479,900

2 Beds ⋅ 1 Baths ⋅ E13636850 MLS

Welcome to this charming 2-bedroom, 2-storey detached century home, set on a spacious ravine lot on a quiet Central Oshawa street. This inviting property features a large living room, perfect for relaxing or entertaining, along with a generously sized eat-in kitchen offering a walkout to a 15 x 10 deck and expansive backyard-ideal for indoor/outdoor living.The upper level was updated in 2022 and includes a large 4-piece bathroom, updated plumbing and wiring, laminate flooring throughout, and a gas furnace (2024). Parking for one vehicle is available on a shared driveway to the south of the property. Conveniently located near public transit, schools, shopping, and with easy access to the 401 and GO Train. Fantastic opportunity for first-time buyers, downsizers, or investors.

493 St. Lawrence Avenue, Oshawa

$715,000

3 Beds ⋅ 3 Baths ⋅ E13532976 MLS

Welcome to 569 Masson Street - an exceptional circa 1920 character home nestled on one of Oshawa's most sought-after, tree-lined streets. Surrounded by charming century properties, this beautifully maintained 3-bedroom, 3-bathroom residence is far from your typical cookie-cutter home. Step inside to a bright, warm and inviting main floor featuring hardwood flooring throughout the living and dining rooms, perfect for entertaining. The spacious kitchen offers ample counter space and functionality, while the oversized family room boasts brand new broadloom, a convenient powder room, walk-in storage closet,and walk-out to a private backyard deck-ideal for indoor-outdoor living. Upstairs, you'll find three generously sized bedrooms, all with hardwood floors and closets, along with a bright and well-appointed 4-piece bathroom. The finished basement adds valuable living space with endless versatility-perfect as a recreation room, home office, or guest suite (walk-up)-complete with a 2-piece bathroom, laundry area, and additional storage. Enjoy your own private, fully fenced backyard oasis, a true gardener's delight featuring mature trees, a garden shed, and a laneway behind. Parking is a breeze with a detached 1-car garage plus a 4-car driveway-ideal for families and entertaining guests. Major updates include furnace and air conditioning (2021) and roof (2021). Located in the highly desirable Dr. S.J. Phillips Public School and O'Neill Collegiate district, and close to parks, amenities, and transit. Come fall in love.

569 Masson Street, Oshawa

$525,000

3 Beds ⋅ 1 Baths ⋅ E13147898 MLS

Offered for the First Time in Many Years, this Charming Two Storey Home is Ideally Located in a Convenient Oshawa Neighbourhood. Featuring Three Bedrooms and One Bathroom, this Property is Perfect for Families or First Time Home Buyers. Step Inside to a Welcoming Front Entrance Leading to an Upgraded Kitchen Complete with Gleaming Countertops and Ample Pantry Space ~ Great For Anyone that Loves to Spend Time Creating in the Kitchen. A Separate Dining Room with Large Windows & Hardwood Floors that Opens Up to the Bright and Spacious Living Room with Plenty of Space for Everyday Living and Entertaining. Upstairs, you will Find Three Well Sized Bedrooms, Including a Spacious Primary Bedroom with "His and Her" Closets, the 2 Additional Bedrooms both Feature Closets and One Bedroom with a Walk out to the Enclosed Porch. At the Rear of the Home, there is a Large Uninsulated Porch that Leads to a Generous 2 Tier Deck Overlooking a Family Friendly Backyard - Perfect for Relaxing on Summer Days and Hosting Family Gatherings. The Property Offers Convenient 2 Car Parking. Located Close to Schools, Shopping, Restaurants, Recreation Centres, Hospital and Much More! This Home Combines Comfort, Space and the Convenience of a Great Location. Don't Miss Your Opportunity to View this Fantastic Oshawa Home!

49 Brock Street E, Oshawa

$899,000

E12915534 MLS

This well-maintained professional office building is located in a prime area near the business core of downtown Oshawa and the courthouse. It offers a turnkey solution suitable for both user and investment purposes. The building features finished office spaces on the main floor, second floor, and loft. Seven lined parking spots, with the capacity to stack up to 12 cars. Built in 1910, the building spans approximately 2,725 square feet across three levels, making it a versatile and attractive option for a variety of business needs.

32 Elgin Street E, Oshawa

Oshawa Homes with 100+ Approx Age

Newest Oshawa Homes with 100+ Approx Age