Oshawa Homes with 100+ Approx Age

Oshawa Homes with 100+ Approx Age

Welcome to Oshawa, Ontario—a vibrant city that beautifully marries the charm of historical roots with the conveniences of modern living. Nestled in the heart of Durham Region, Oshawa is known for its rich automotive history, thriving cultural scene, and diverse community. With its close proximity to Lake Ontario, residents enjoy stunning waterfront parks, picturesque trails, and recreational activities that cater to all ages.

Oshawa boasts a variety of architectural styles, particularly in its neighborhoods featuring homes with a rich history. Many properties in this area are over 100 years old, offering a unique glimpse into the past with their timeless designs and character. These vintage homes often showcase intricate craftsmanship, high ceilings, and stunning woodwork, making them a perfect choice for those who appreciate the charm of yesteryear.

Living in Oshawa means being part of a community that values both heritage and progress. The city is home to excellent schools, lush parks, and a bustling downtown area filled with shops, restaurants, and entertainment options. The local arts scene thrives with galleries, theaters, and festivals that celebrate creativity and culture.

Whether you’re a first-time homebuyer, a family looking for a friendly neighborhood, or a retiree seeking a peaceful retreat, Oshawa offers a variety of housing options that cater to every lifestyle. Embrace the beauty and history of this remarkable city—where the past meets the present, and every street tells a story. Discover your dream home in Oshawa today!

Newest Oshawa Homes with 100+ Approx Age

$849,999
3 Beds ⋅ 2 Baths ⋅ E13585340 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 tranquillity 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
$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
$699,900
4 Beds ⋅ 2 Baths ⋅ E13514596 MLS
Charming and full of character, this 1.5 story detached home offers over 2100 square feet of timeless appeal blended with everyday comfort. Upon entering the large foyer, you will feel the history through solid wood detailing, and peak craftsmanship that harkens back to a bygone era. Bathed in natural light, the main floor den opens into the living room which boasts a brick fireplace and large windows. You are then led into a dining room that has the perfect balance of privacy and functionality. The kitchen provides a warm and inviting space for family and friends to gather, complete with a breakfast area and storage benches. In 1991, the addition of a family room and primary bedroom was built with the spacious family room offering an ideal setting for entertaining or relaxing. Upstairs, you will find 3 generously proportioned bedrooms, and just before the entrance to the sizeable primary bedroom, a charming alcove offers a cozy nook, perfect for a reading corner, or a quiet sitting area. The finished basement grants additional living space along with a well-appointed laundry room and ample storage areas. Step outside to a spacious, private backyard with no neighbours behind - perfect for relaxing, entertaining, or enjoying a beautiful evening of quiet contemplation. A rare opportunity to own a truly special home with enduring charm. Perfect for families. Close to public transportation, Lakeridge Health, elementary and secondary schools, places of worship and all amenities.

482 Simcoe Street N, Oshawa
$468,990
3 Beds ⋅ 3 Baths ⋅ E13448182 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!

11 MAPLE Street, Oshawa
$535,000
3 Beds ⋅ 1 Baths ⋅ E13147898 MLS
Open House this Sunday, July 26th from 1pm to 3pm! 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
$489,900
2 Beds ⋅ 1 Baths ⋅ E13116692 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
$857,000
5 Beds ⋅ 5 Baths ⋅ E13089484 MLS
Victorian Style 2 1/2 Storey Home Located In Central Heart Of Oshawa. Close to All Amenities. Featuring 4+1 Bedrooms & 5 Baths. High Ceilings, Laminate wood flooring Thru Out, Refinished stairs, Potlights in & out. Approx 3000 SqFt. Large Primary Rooms, Beautifully Renovated Kitchen W/Quartz Counters, Centre Island. Upper Floor Loft Can Be Converted To Huge Office - Work From Home Space Or 5th Bedroom W/Ensuite Bath. Large Corner 85Ft Lot. Double Car Garage. Needs Some TLC. Inground Pool (Not Completed) Rewired full house 200AMP panel, water softner as- is.

512 Simcoe Street N, 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
$599,000
6 Beds ⋅ 3 Baths ⋅ E12901112 MLS
Turnkey investment opportunity offering strong cash flow. This residential property features three self-contained units rented out to tenants. The property has been extensively renovated, including a roof (2016), A/C (2021), furnace (2021), and windows(2020), with all three units fully updated in 2021. The main unit includes 2 bedrooms and 1 bathroom, the second unit offers 1 bedroom and 1 bathroom, and the lower-level unit features 3 bedrooms and 1 bathroom.

211 Albert Street, Oshawa
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