Oshawa Homes with 100+ Approx Age

Oshawa Homes with 100+ Approx Age

Welcome to Oshawa, Ontario—an enchanting city nestled in the heart of Durham Region, just east of Toronto. Known for its rich history and vibrant community, Oshawa offers an inviting blend of urban convenience and natural beauty. With a population of over 170,000, this thriving city is renowned for its diverse neighborhoods, excellent schools, and a plethora of recreational opportunities.

One of the most charming aspects of Oshawa is its historic homes, particularly those with an age of 100 years or more. These vintage properties, steeped in character and stories of the past, showcase architectural styles that reflect the evolution of Canadian design. From stately Victorian mansions to quaint bungalows, each home offers a unique glimpse into the city’s heritage. Living in one of these timeless residences means you’re not just buying a house; you’re becoming part of a narrative that has shaped the community for generations.

Oshawa also boasts an array of parks, cultural attractions, and a burgeoning arts scene, making it a perfect place for families, young professionals, and retirees alike. The city’s commitment to green spaces is evident in its many parks and trails, encouraging outdoor activities and fostering a sense of community.

With its rich history, charming homes, and a vibrant lifestyle, Oshawa is more than just a place to live; it’s a place to thrive. Whether you’re looking to invest in a historic property or simply explore the area, Oshawa is ready to welcome you with open arms. Come discover the charm of this remarkable city!

Newest Oshawa Homes with 100+ Approx Age

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
168 Centre Street S, Oshawa
$765,000
5 Beds ⋅ 3 Baths ⋅ E13886168 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
$789,900
3 Beds ⋅ 2 Baths ⋅ E13865712 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
266 Division Street, Oshawa
$439,900
4 Beds ⋅ 2 Baths ⋅ E13747558 MLS
Welcome to 266 Division St! A Charming brick home in the heart of O'Neill - finished basement, detached garage, and everything you need justaround the corner. This 1.5-storey offers a bright kitchen and spacious family room on the main floor, well-sized bedrooms and a full bathupstairs, and a finished basement with 2 additional bedrooms and a second bathroom - ideal for growing families or investors. Private backyard on a 26.5 x 100 ft lot. Steps to transit, minutes to Durham College, Oshawa GO, and Lakeridge Health. Connaught, Mary Street, and CentennialParks nearby. Dr. S.J. Phillips PS and O'Neill CVI in catchment. Click on more information for 3D tour , virtual tour, feature sheet and floor plan.

266 Division Street, Oshawa
569 Masson Street, Oshawa
$699,000
3 Beds ⋅ 3 Baths ⋅ E13837112 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
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
27 BUCKINGHAM Avenue, Oshawa
$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
27 Rowe Street, Oshawa
$699,000
3 Beds ⋅ 3 Baths ⋅ E13764562 MLS
1,600 sq. ft. ABOVE GRADE, PLUS a finished basement, over $300,000 in renovations, and absolutely no shortage of personality! This extensively renovated 2.5-storey detached home is anything but ordinary, offering 3 bedrooms, 3 bathrooms and surprises at every turn. Step inside to warm wood floors, a beautiful coffered living room ceiling and a generous custom kitchen featuring a stunning onyx backsplash and a chalkboard wall. Upstairs, two bedrooms and a gorgeous 5-piece bathroom with double sinks and a custom shower are just the beginning. The real showstopper? An entire third floor dedicated to a spectacular, sun-filled loft-style primary retreat! Three windows, loads of space and endless possibilities for a sitting area, dressing room or home office. And there's more! The newly finished basement (2026) adds even more living space, complete with a fabulous clawfoot tub. Outside, the gardens are lush and the side yard is made for entertaining, with a stamped concrete patio and a lovely pergola. All the fun of outdoor living without spending your weekends mowing the lawn! And just when you think you've seen it all, there's a charming little "General Store" shed, complete with its own electrical panel. Behind the personality are serious upgrades: electrical, plumbing and pot lights (2019), flooring and front porch (2026), plus a durable metal roof. Big on space, big on style and refreshingly low on maintenance. Just move in and enjoy!

27 Rowe Street, Oshawa
97 Adelaide Avenue E Unit East, 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
13 Brock Street E, 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
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