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

168 Centre Street S, Oshawa
$726,000
5 Beds ⋅ 3 Baths ⋅ E14167046 MLS
**PRIME LOCATION IN THE HEART OF OSHAWA - RESIDENTIAL & COMMERCIAL POTENTIAL!** Incredible opportunity with endless possibilities. Discover this well-maintained property offering exceptional residential and commercial potential with R1-C/CIN/SO-D zoning. Featuring 2 separate units with 5 spacious bedrooms and 3 bathrooms, this versatile property offers living spaces on both the main and second floors. Enjoy beautiful hardwood flooring, an updated kitchen with elegant quartz countertops, and a functional layout. Ideal for residential living or a variety of potential professional and commercial uses, including accounting, law, real estate offices, daycare, retirement living, senior care, nursing facilities, and more, subject to municipal zoning and approvals. Conveniently located within walking distance of numerous amenities and just minutes from Highway 401 and Oshawa shopping centre. A RARE OPPORTUNITY FOR HOMEOWNERS, INVESTORS, AND BUSINESS OWNERS! DON'T MISS OUT!

168 Centre Street S, Oshawa
559 Masson Street, Oshawa
$749,900
3 Beds ⋅ 2 Baths ⋅ E14166304 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
11 MAPLE Street, Oshawa
$399,900
3 Beds ⋅ 3 Baths ⋅ E14163852 MLS
Discover the perfect blend of modern living, comfort, and convenience in this beautifully renovated home! Featuring 3 spacious bedrooms and 3 bathrooms, this move-in-ready property offers stylish, contemporary finishes throughout and a private second-floor rooftop terrace-perfect for relaxing, entertaining, or enjoying your morning coffee. Thoughtfully updated and ideally located just minutes from schools, parks, shopping, transit, and everyday amenities, this home offers exceptional value and lifestyle appeal. Whether you're a first-time homebuyer looking for the perfect place to call home or an investor seeking a turnkey opportunity, this is one you won't want to miss!

11 MAPLE Street, Oshawa
577 Albert Street, Oshawa
$388,500
2 Beds ⋅ 2 Baths ⋅ E14161140 MLS
Attention Investors, Renovators & Contractors! Excellent opportunity to own a detached home situated on a generous lot in an established Oshawa neighbourhood. This property offers great potential for buyers looking to renovate, restore, or add value through improvements. Ideal for investors seeking their next project or buyers looking to customize a home to their preferences. Conveniently located close to schools, parks, shopping, public transit, and other everyday amenities, with easy access to major transportation routes. Property is being sold in "as-is, where-is" condition, with no representations or warranties. Buyers are encouraged to conduct their own due diligence regarding the property's condition, measurements, permitted uses, and future potential. Don't miss this investment opportunity in Oshawa!

577 Albert Street, Oshawa
27 Rowe Street, Oshawa
$677,888
3 Beds ⋅ 3 Baths ⋅ E14152790 MLS
Some homes check the boxes. Others make you fall in love. This one does a little of both! With over 1,600 sq. ft. above grade, a newly finished basement and more than $300,000 in renovations, this distinctive 2.5-storey detached home delivers space, style and personality in equal measure. Thoughtfully reimagined from top to bottom, it offers 3 bedrooms, 3 bathrooms and unexpected details at every turn. Warm wood floors, an elegant coffered living room ceiling and a generous custom kitchen with a striking onyx backsplash and playful chalkboard wall set the tone. The second floor features two spacious bedrooms and a beautifully appointed 5-piece bathroom with double sinks, a jacuzzi tub, and a custom shower. Then comes the showstopper: an entire third-floor loft retreat, flooded with natural light from three windows! Currently enjoyed as a spectacular primary bedroom, this significant space offers exciting possibilities for reconfiguration into two or potentially three bedrooms, subject to the necessary approvals. Whether you envision a luxurious private sanctuary, additional bedrooms, or a home office or creative studio, the flexibility is yours to explore. The newly finished basement (2026) adds even more living space, complete with a charming clawfoot tub. Outside, lush gardens, a stamped concrete patio and pergola create an inviting outdoor escape without the burden of extensive yard maintenance. There's even a whimsical "General Store" shed with its own electrical panel! Major updates include electrical and plumbing (2019), flooring and front porch (2026), plus a durable metal roof. The house also has newer appliances (2021). Beautifully finished, refreshingly different and full of possibilities. Come see what makes this home so special!

27 Rowe Street, Oshawa
86 Gibbons Street, Oshawa
$522,500
3 Beds ⋅ 2 Baths ⋅ E14134490 MLS
Bring your vision and unlock the potential of this detached bungalow in an established Oshawa neighbourhood. Situated on a generous corner lot, this property offers an exciting opportunity for renovators, investors, contractors or buyers looking for a home they can update and personalize. The home features 2 + 2 bedrooms, a finished basement, private 3 car driveway and detached garage, providing flexibility for a variety of needs. Outside the spacious property includes plenty of outdoor space to reimagine and enjoy. Whether you are looking for your next renovation project, an investment opportunity, or a home you can transform over time, this property offers the space, lot size and location to bring your ideas to life. Located in Oshawa's McLaughlin neighborhood, close to schools, parks, public transit, hospitals, library, shopping and everyday amenities, with convenient access to major routes. Bring your ideas, see the possibilities and make this property your own. A unique opportunity for buyers ready to create something special.

86 Gibbons Street, Oshawa
168 Centre Street S, Oshawa
$739,900
5 Beds ⋅ 3 Baths ⋅ E14126230 MLS
**PRIME LOCATION IN THE HEART OF OSHAWA - RESIDENTIAL & COMMERCIAL POTENTIAL!** Incredible opportunity with endless possibilities. Discover this well-maintained property offering exceptional residential and commercial potential with R1-C/CIN/SO-D zoning. Featuring 2 separate units with 5 spacious bedrooms and 3 bathrooms, this versatile property offers living spaces on both the main and second floors. Enjoy beautiful hardwood flooring, an updated kitchen with elegant quartz countertops, and a functional layout. Ideal for residential living or a variety of potential professional and commercial uses, including accounting, law, real estate offices, daycare, retirement living, senior care, nursing facilities, and more, subject to municipal zoning and approvals. Conveniently located within walking distance of numerous amenities and just minutes from Highway 401 and Oshawa shopping centre. A RARE OPPORTUNITY FOR HOMEOWNERS, INVESTORS, AND BUSINESS OWNERS! DON'T MISS OUT!

168 Centre Street S, Oshawa
49 Brock Street E, Oshawa
$499,000
3 Beds ⋅ 1 Baths ⋅ E14028054 MLS
Charming, Welcoming and Fully of Character ~ This Oshawa Home Has So Much to Offer! Ideally Located in a Convenient Oshawa Neighbourhood, this Lovely Two Storey Home is Ready to Welcome Another Family for it's Next Chapter! Featuring 3 Bedrooms and 1 Bathroom, this Home Offers a Wonderful Combination of Comfort, Character and Space ~ Perfect for First time Home Buyers, Growing Families or Simply Anyone Looking for a Place to Call Home! Step Inside from the Spacious Front Porch to a Welcoming Front Entrance that Leads You into an Upgraded Kitchen Featuring Gleaming Countertops, Plenty of Pantry Space and Room to get Creative with Your Favourite Recipes! The Separate Dining Room is Filled with Natural Light From the Large Windows and Showcases Beautiful Hardwood Floors, Flowing into the Bright and Spacious Living Room ~ Perfect for Cozy Nights In, Family Time or Entertaining Friends! Head Upstairs Where You'll Find Three Well Sized Bedrooms, Including a Spacious Primary Bedroom Complete with His and Her Closets! The Two Additional Bedrooms Both Offer Closet Space, with One Featuring a Walkout to an Enclosed Porch ~ A Charming Little Bonus Space with So Many Possibilities! At the Back of the Home, You'll Discover a Large Porch Leading to a Generous Two Tier Deck Overlooking the Backyard. Whether You're Enjoying Your Morning Coffee, Soaking up the Summer Sunshine, Hosting a BBQ or Simply Relaxing after a Long Day, this Outdoor Space is Ready to be Enjoyed! With Convenient Private Parking for Two Cars and a Fantastic Location Close to Schools, Shopping Restaurants, Recreation Centres, the Hospital and So Much More, Everyday Living Couldn't Be Easier! Full of Charm, Wonderful Spaces and Endless Opportunities to Make it Your Own, this is a Home You'll want to see for Yourself! Don't Miss Your Chance to Make this Oshawa Home your Very Own.

49 Brock Street E, Oshawa
308 King Street E, Oshawa
$899,900
5 Beds ⋅ 3 Baths ⋅ E14005848 MLS
Welcome to this stunning brick two-storey home situated on a 50-foot lot east of downtown Oshawa, with nearly 1,900 square feet above grade (MPAC) as well as a lower-level in-law suite with its own entrance and an inviting and indulgent saltwater inground heated pool in the backyard. The main floor keeps its century charm while offering dreamy updates to offer the absolute best of both worlds! The combined living and dining rooms stretch nearly 27 feet, anchored by a fireplace at one end and bright south-facing windows at the other, finished with crown moulding and luxury vinyl flooring. The family room allows the light to flood through the open concept space with an abundance of south facing windows. It also opens to the kitchen featuring quartz countertops, white cabinetry, glass front uppers, a large island under a stainless chimney hood, and a double sink under the windows. This level is finished with a 2-piece bath and a mudroom leading to the covered back deck. Upstairs, four rooms open off the hall. The primary bedroom is spacious and bright with a large sliding door closets and ultra convenient laundry nook (2022) within! There are 3 more rooms that can be used as bedrooms but are currently presented as a second bedroom, a cozy family room and an office. The 5-piece modern bath includes a shower panel system in a glass shower and a freestanding tub. The lower level, finished in 2022, has a separate entrance, a second kitchen, a rec room, a bedroom, its own laundry, and an elegant 4-piece bath with a make-up station, soaker tub and a glass walk-in shower. Outside, enjoy the heated saltwater pool with concrete surround or let kids play on the lawn while you comfortably watch from the deck. A long private drive runs to the detached garage, with six parking spaces in all. Roof 2022, windows 2020, furnace and central air 2022. Costco and No Frills are both under a kilometre away. 401 is minutes away. Home is being sold as a single family residence.

308 King Street E, Oshawa
349 Kingsdale Avenue, Oshawa
$479,900
2 Beds ⋅ 1 Baths ⋅ E13826760 MLS
Welcome to this warm and welcoming 2-bedroom bungalow in Oshawa's desirable Connaught Park neighbourhood. Situated on a generous lot in a mature North Oshawa community, this charming home offers exceptional value for first-time buyers, down-sizers, investors, or those seeking future potential.Freshly painted throughout with bright, inviting living spaces, the home features a bright functional kitchen with space for casual dining and walk-out to a mudroom, two spacious bedrooms with ample natural light, and some original hardwood flooring and plank subfloors that add character and charm. The rear mudroom provides walk-out access to a private, fully fenced backyard, while the large covered front porch offers the perfect place to relax and enjoy summer evenings.The full unfinished basement includes a laundry area and abundant storage space. Parking for up to three vehicles adds additional convenience.Ideally located just steps to O'Neill Collegiate, Dr. S.J. Phillips Public School, parks, public transit, shopping and everyday amenities. Enjoy convenient access to the Costco retail district, Lakeridge Health Oshawa Hospital, Durham College, Ontario Tech University, and the restaurants, shops and entertainment of Downtown Oshawa.A unique feature of this property is the vacant lots located directly behind and beside the home, creating added privacy, an open feel, and potential future development opportunities.

349 Kingsdale Avenue, Oshawa
354 Verdun Road, Oshawa
$459,900
2 Beds ⋅ 1 Baths ⋅ E13822600 MLS
Beautifully renovated bright and spacious home! absolutely charming! Must be seen!!A rare gem! Full of character and charm, this unique home offers a comfortable bedroom on the main level, with an additional loft space completed in 2024 that can serve as a second bedroom, sitting area, or flexible living space. The kitchen and bathroom have been tastefully updated, while the additional family room/office provides direct access to a spacious deck and inviting backyard. An excellent location for commuters, with convenient access to the 401 and proximity to the proposed GO Train station.

354 Verdun Road, Oshawa
292 William Street E, Oshawa
$829,900
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
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