Oshawa Homes with 100+ Approx Age

Oshawa Homes with 100+ Approx Age

Welcome to Oshawa, Ontario—a vibrant city that beautifully blends rich history with modern living. Nestled in the heart of Durham Region, Oshawa is not only known for its stunning lakeside views along Lake Ontario but also for its welcoming community and diverse cultural scene. With a population of over 160,000 residents, Oshawa offers a perfect mix of urban conveniences and suburban charm, making it an ideal place for families, young professionals, and retirees alike.

One of the most captivating aspects of Oshawa is its historical architecture, particularly the homes that boast an impressive age of 100 years or more. These charming residences tell stories of the past, reflecting the city’s deep-rooted heritage and character. From stately Victorian homes adorned with intricate woodwork to cozy bungalows that exude warmth and nostalgia, the older homes in Oshawa are a treasure trove for those who appreciate craftsmanship and historical significance.

Living in one of these age-old homes not only provides a unique aesthetic but also connects you to the rich tapestry of Oshawa’s history. Many of these properties have been lovingly maintained or thoughtfully renovated, offering modern amenities while preserving their original charm. The neighborhoods surrounding these historic homes are often filled with tree-lined streets, local parks, and a sense of community that fosters lasting relationships among neighbors.

Whether you’re looking for a quaint abode with character or a family home steeped in history, Oshawa’s older homes present an enticing opportunity to embrace the past while enjoying the conveniences of contemporary living. Come explore the charm of Oshawa, where history and community thrive hand in hand!

Newest Oshawa Homes with 100+ Approx Age

$679,900
3 Beds ⋅ 2 Baths ⋅ E13773742 MLS
Location!Location! Buckingham Meats Across the street, Alexandria Park and Lakeridge Hospital behind you, Parkwood Estate 5 minute walk and Oshawa Golf golf at the end of the street. The perfect starter home for those looking to get into a detached home in one of the nicest pockets in Oshawa. A large covered front porch and an extra large composite deck in the back overlooking Alexandria park for your morning coffee. A large garden shed and a fully fenced, safe and worry free yard for the kids or furry friends. Within the last year a new AC, dishwasher, hoodfan and washer were installed.

27 BUCKINGHAM Avenue, Oshawa
$474,900
3 Beds ⋅ 2 Baths ⋅ E13767536 MLS
A 1925 built Century detached home on a generous 45 foot frontage by 207 foot deep lot in Vanier, a short walk from the Oshawa Centre, with eight parking spaces and a detached double garage at the back. A covered front porch runs the full width of the home. Inside, hardwood carries through the living and dining rooms and the main floor bedroom, an open staircase with turned newel posts climbs from the main level, and the living room has a wood burning fireplace under a painted brick surround. A glass paned French door for the storage room. The kitchen is at the back of the home with a walk out to rear deck and it offers white cabinetry, a glass front upper, tile backsplash, a double stainless sink under the window, stainless range and fridge. The 4 piece bath is on the main floor and the tub surround has been modernized. Upstairs, under sloped ceilings and dormer windows, are two more bedrooms, a 2 piece bath, and an original exposed post and beam at the landing. Both of those rooms are down to subfloor and ready for the flooring you pick. The full basement is finished with above grade windows and holds multiple rooms of potential, laundry with a sink, and the utility room. The lot runs 207 feet deep, hedged and treed on both sides, with an above ground pool, a large gravel drive, and a 23 by 21 foot detached garage at the end of it. Seven parking spaces in total. Walk to the Oshawa Centre, Memorial Park and downtown. Lakeridge Health, the Michael Starr Trail and Highway 401 at Park Rd are all within about two kilometres.

97 Park Road S, Oshawa
$699,000
3 Beds ⋅ 3 Baths ⋅ E13764562 MLS
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. Driveway can fit 2 small vehicles or a small and a mid size vehicle.

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
They don't build them like this anymore.Welcome to 569 Masson Street, a charming circa 1920 character home on one of Oshawa's most sought-after tree-lined streets, surrounded by beautiful century homes. This 3-bedroom, 3-bathroom home offers the character, space and outdoor living that cookie-cutter homes simply can't replicate. The bright main floor features hardwood floors, a spacious kitchen and oversized family room with brand-new broadloom, powder room, walk-in storage and walk-out to the deck. Upstairs are three generously sized bedrooms, all with hardwood floors, plus a 4-piece bath. The finished walk-up basement adds a recreation room, 2-piece bath, laundry and storage. Enjoy a private, fully fenced backyard with mature trees, garden shed and rear laneway-a gardener's delight. Detached garage plus 4-car driveway. Updates include furnace/A/C and roof (2021). Close to parks, amenities, transit and schools, including Dr. S.J. Phillips and O'Neill Collegiate. Character, space and a backyard with personality.

569 Masson Street, Oshawa
$499,000
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
Start Your Search