Oshawa Homes with 51-99 Approx Age

Oshawa Homes with 51-99 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 known for its friendly community, stunning waterfront along Lake Ontario, and a variety of recreational opportunities. With a population of over 170,000, this dynamic city is a hub for culture, education, and economic growth.

Oshawa boasts a diverse real estate market, and for those seeking homes with a touch of character, properties aged between 51 to 99 years offer a unique charm. These homes often feature classic architectural styles, including Craftsman, Victorian, and Tudor designs, providing a nostalgic glimpse into the past while accommodating modern amenities. Many of these residences are situated in established neighborhoods, surrounded by mature trees and lush gardens, creating a serene environment perfect for families and individuals alike.

The city is not only rich in history but also in recreational activities. Residents enjoy easy access to parks, trails, and the scenic waterfront, making it an ideal location for outdoor enthusiasts. Oshawa is also home to a vibrant arts scene, with galleries, theaters, and cultural events that engage the community year-round.

With its excellent schools, convenient transportation options, and a strong sense of community, Oshawa is an ideal place to call home. Whether you’re a first-time buyer or looking to settle down in a historic gem, homes in Oshawa with an approximate age of 51-99 years offer a perfect blend of character, comfort, and community spirit. Discover the charm of Oshawa and find your dream home today!

Newest Oshawa Homes with 51-99 Approx Age

446 Brest Court, Oshawa
$599,900
3 Beds ⋅ 3 Baths ⋅ E14121164 MLS
Four level back split semi on massive pie shaped lot. Court location. Surprisingly large and spacious floor plan. Features 2 kitchens and 3 full baths. Barrier free showers in both 3-piece bathrooms. All four levels finished. Tons of space. Lots of closets. Shows neutral and clean. Huge family room walks out to covered deck and massive fenced yard with mature trees. Parking for 5 vehicles. Very unique. Great for multigenerational living.

446 Brest Court, Oshawa
169 Pontiac Avenue, Oshawa
$735,000
4 Beds ⋅ 2 Baths ⋅ E14116640 MLS
Welcome to this 3-bedroom detached bungalow in North Oshawa, located on Pontiac Avenue between Mohawk and Sommerville. A key feature is the oversized, insulated 25 30 ft detached double garage and workshop area, complemented by a private driveway with parking for up to six cars.Move-in ready, the home features an updated kitchen and bathrooms, hardwood floors throughout the main floor, and fresh paint. The spacious sunroom has new flooring and overlooks a fully fenced, private backyard surrounded by mature hedges.The fully finished basement offers an additional bedroom, a 3-piece bathroom, new flooring and a large laundry room.Just a 2-minute walk to Sunset Heights Public School.

169 Pontiac Avenue, Oshawa
430 Harcourt Drive, Oshawa
$649,900
4 Beds ⋅ 2 Baths ⋅ E14112580 MLS
This house is freshly painted and professionally cleaned, ready to move in. Rare 4-Level Backsplit Semi-Detached on an Extra-Large 27.6 x 200.3 Ft Lot! This spacious and well-maintained home offers exceptional potential for homeowners, extended families, and investors alike. Situated on an extra-deep lot measuring approximately 27.6 x200.3 ft, this property provides an abundance of indoor and outdoor space that is rarely found in the area. The main level features a large family-sized eat-in kitchen overlooking the living room, complete with a beautiful bow window that fills the space with natural light and laminate flooring. The upper level offers two generously sized bedrooms and a large 3-piece bathroom. The lower level features an extra-large primary bedroom with two closets and a renovated bathroom, providing excellent additional living space. A separate side entrance to the lower level adds tremendous flexibility and makes this property particularly attractive to investors and multi-generational families. The layout and separate entrance also offer potential for conversion into a legal duplex, subject to applicable municipal zoning, permits, building code and other requirements. Enjoy 3-car parking, a huge backyard with two storage sheds, and a front yard equipped with an installed sprinkler system for convenient lawn maintenance. The home also features a new air conditioner for added comfort during the warmer months. An exceptional opportunity to own a spacious 4-level backsplit with an extra-large, 200+ ft deep lot, excellent parking, separate entrance, and outstanding future potential. Must See! ***Note: Some pictures have virtual staging***

430 Harcourt Drive, Oshawa
523 Brentwood Avenue, Oshawa
$649,000
4 Beds ⋅ 2 Baths ⋅ E14111192 MLS
Tucked into an established Oshawa neighborhood, just north of Highway 401, 523 Brentwood Avenue offers a welcoming blend of character, thoughtful updates, and everyday convenience. At the heart of this inviting raised bungalow is a bright and welcoming living room, where an oversized picture window fills the space with natural light and overlooks the charming, tree-lined streets beyond. The combined kitchen and dining area features tasteful updates, including granite countertops and stainless steel appliances, with a walkout to a spacious elevated deck surrounded by mature trees, offering a quiet sense of privacy. The main level features three bedrooms and a four-piece bathroom, while the finished lower level provides additional living space and flexibility. Complete with a fourth bedroom, three-piece bathroom, recreation room with gas fireplace, walkout, and separate side entrance, this versatile space offers excellent potential for extended family or multigenerational living. Outside, the backyard enjoys a peaceful setting with a small creek bordering the rear of the property, adding to the home's natural surroundings. With its established neighborhood setting, functional layout, and thoughtful improvements, 523 Brentwood Avenue offers a wonderful opportunity to settle in and make it your own.

523 Brentwood Avenue, Oshawa
200 Oshawa Boulevard N, Oshawa
$499,999
3 Beds ⋅ 2 Baths ⋅ E14111170 MLS
Welcome to 200 Oshawa Blvd N, a beautifully updated home offering comfort, style, and everyday practicality.Inside, you'll find a refreshed kitchen ideal for cooking and gathering, paired with new flooring that flows through the main living spaces. Bright, open rooms create a warm and welcoming feel throughout.Step outside to your private backyard deck, perfect for entertaining, relaxing, or enjoying your morning coffee.The partially finished basement adds valuable bonus space and features a convenient 3 piece bathroom, complemented by a separate side entrance, offering flexible use for extended family, guests, or future potential.Thoughtfully improved and move in ready, this home delivers modern updates in a well established neighbourhood close to schools, parks, shopping, and transit.A great opportunity for first time buyers, growing families, or investors. Come see what makes this home special.Book your private showing today.

200 Oshawa Boulevard N, Oshawa
142 Adelaide Avenue W, Oshawa
$775,000
3 Beds ⋅ 2 Baths ⋅ E14106332 MLS
Absolutely beautiful All Brick circa 1931 home located in one of the most desirable neighbourhoods in all of Oshawa. Steps away from Parks, Hospital, Oshawa Private golf club, shopping, transit and historical Oshawa landmark Parkwood Estates. This stunner has been tastefully updated with keeping all the charm of the creative woodworking original finishes. Enter through the vestibule a spot to hang your coats and warm up w/ heated floors. Walk into the charming entrance to the living room that is spacious and cozy w/ the wood-burning fireplace. Updated mudroom (2020) off living area that has a walkout to a newer saltwater pool and fresh landscaping. Beautiful family dining area perfect for hosting updated w/built-in cabinets and coffee bar. Kitchen updated w/ Granite counters, subway tile b/s, plenty of cupboards and added homework nook. 2-piece powder room w/ heated floors on main updated (2026), Hardwood flooring throughout the entire home. Upstairs has 3 generously sized bedrooms, primary has a B/I closet and an added office space or nursery room. 2nd and 3rd bedrooms both have good-sized closets and hardwood flooring. Main bathroom updated w/ new double vanity, glass shower and heated flooring. Updated all-copper electrical, new shingles (2018), Furnace (2018), A/C (2018), Exterior doors (2023), Added attic insulation (2019). Driveway side of the home is on side street Grooms Ave

142 Adelaide Avenue W, Oshawa
219 Etna Avenue, Oshawa
$649,900
4 Beds ⋅ 2 Baths ⋅ E14106240 MLS
Welcome to this charming bungalow in Central Oshawa. Featuring 2+2 bedrooms, an open-concept main floor, and beautifully renovated kitchen and bathroom on main floor. Freshly painted all throughout and all hardwood on main floor. This home offers comfort and functionality for the whole family. The finished basement boasts a separate side entrance, a second kitchen and a 3-pc bathroom, making it ideal for extended family living. Enjoy the spacious backyard, perfect for outdoor entertaining and family gatherings. Complete with a single-car garage and conveniently located just minutes from Highway 401, GO Station, Durham College and Ontario Tech University, and Oshawa Centre. Close to parks, schools, shops, dining and public transit and everyday amenities. A fantastic opportunity for families, first-time buyers and investors alike.

219 Etna Avenue, Oshawa
868 Grierson Street, Oshawa
$475,000
3 Beds ⋅ 2 Baths ⋅ E14103702 MLS
Looking for a home with character, versatility, and incredible garage space? This detached brick bungalow offers much more than meets the eye! Featuring hardwood floors and a functional layout, the main level offers two bedrooms, a full bathroom, and a separate dining room that could easily be converted into a third main-floor bedroom. Bright enclosed sun porches at both the front and back provide inviting spaces to enjoy your morning coffee or relax at the end of the day. The finished basement offers even more flexibility with an additional bedroom, bathroom, and versatile living space ideal for extended family, guests, a home office, or multigenerational living. A convenient walkout from one of the bedrooms provides direct access to the outdoors. Enjoy year-round comfort with a modern hybrid heating system combining an energy-efficient heat pump and forced-air gas furnace. The real bonus? A massive detached garage with loft! Perfect for car enthusiasts, hobbyists, contractors, or anyone needing exceptional workshop and storage space. The fully fenced backyard features a large access gate for easy vehicle and equipment access, plus an additional storage shed and plenty of room to relax or entertain. Conveniently located in Oshawa's desirable Centennial neighbourhood, close to schools, parks, shopping, restaurants, public transit, and major commuter routes. Whether you're a first-time buyer, growing family, or looking for flexible living space with an exceptional garage, this property offers an incredible opportunity to make your next move! Downsizing has never been more affordable!

868 Grierson Street, Oshawa
621 Masson Street, Oshawa
$799,900
4 Beds ⋅ 2 Baths ⋅ E14102176 MLS
Step into the charm and character of a beautiful all-brick century home, where timeless craftsmanship meets the comforts of today. Rich with original and unique architectural details, this special residence offers a rare opportunity to own a home with true personality and history. Ideally situated in a prime location within a sought-after school district, this four-bedroom, one-and-a-half-bath home offers generous space for family living, entertaining, and making memories for years to come. Original features throughout tell the story of the home's heritage, creating warmth and character that simply cannot be replicated in newer construction. Every room offers its own sense of charm, while the solid brick exterior provides the enduring beauty and presence of a classic century home. Outside, the property becomes its own private escape. A beautiful stone patio provides the perfect setting for summer dinners, morning coffee, or evenings spent entertaining friends, while the large backyard offers plenty of room for children, gardening, pets, or simply enjoying the outdoors. Solid garage with hydro is perfect as a workshop or outdoor storage. A rare combination of architectural character, generous living space, a prime location, and an exceptional yard, this is a home with a story to tell - and the opportunity to become part of yours. A/C heat pump installed 2026.

621 Masson Street, Oshawa
390 Mary Street N, Oshawa
$899,900
6 Beds ⋅ 3 Baths ⋅ E14101730 MLS
Welcome to this beautifully updated 2 1/2-storey home, ideally situated in a fabulous area of tree-lined streets and well within excellent school districts! Offering a versatile layout with plenty of space for the whole family, the main and second floor of this home features an eat-in kitchen, 2 bedrooms and 2 full bathrooms, along with a finished basement providing even more room for guests/ teens, entertain, or work from home. One of the home's standout features is the amazing second suite spanning the back of the second and all of the third floors, offering an open-concept kitchen and living room with an electric fireplace, it's own washer & dryer, 2 more bedrooms and a full bathroom. Perfect for extended family, multi-generational living, guests, or added flexibility to suit your needs. Outside, enjoy a large lot with plenty of room to play, entertain, or simply unwind. Perfect area for kids to safely play street hockey, basketball, etc. and the little ones to ride their bikes! The oversized 2-car garage provides exceptional space for parking, storage, hobbies, and more. With its updated finishes, flexible living space, bright second suite, generous lot, and sought-after location close to great schools and everyday amenities, this home offers a wonderful combination of comfort, convenience, and versatility. A fantastic opportunity for families looking for room to grow and space for everyone! Two electrical panels, two hot water tanks. The two rooms in the basement are presently being used as bedrooms with large windows but no closets. Two separate units, there is no access to the second suite from the main house. Would suit families with out of town students looking to share a house or out of town hospital or court staff. Easy walk to downtown campuses and Lakeridge Health. Updated and move in ready. Includes 2 fridges, 2 stoves, 2 B/I microwaves, 2 dishwashers, 2 washers & 2 dryers.

390 Mary Street N, Oshawa
724 Clifton Drive, Oshawa
$735,000
3 Beds ⋅ 2 Baths ⋅ E14098742 MLS
Welcome to this spacious four-level side-split, situated on a generous lot in a sought-after, mature, family-friendly neighbourhood! Offering a versatile floor plan with plenty of room for the entire family, this one owner, well-cared-for home combines comfort, functionality and exceptional potential. The inviting interior features a spacious living room, dining room and kitchen, along with a separate main-floor family room, providing the perfect setting for everyday living and entertaining. The upper level offers three comfortable bedrooms, while the finished lower level provides additional living space, including a generous recreation room and a dedicated workout room - ideal for today's flexible lifestyle. Freshly painted and featuring new broadloom, this home offers a wonderful opportunity to move in and add your own personal touches. Situated on a large, mature lot, the private backyard provides plenty of space for outdoor entertaining, gardening or simply relaxing. Backing onto a church parking lot, the property enjoys added separation from rear residential neighbours. Located in a quiet, established neighbourhood, this inviting home offers the space, flexibility and setting that growing families are looking for. This well maintained home is an estate sale and not all of the details of the upgrades are known. What is known is: Air Conditioner - July 2023; Furnace - January 2025; Electrical panel - October 2026; Roof - 2025; New Carpet - October 2026; Awning over back deck. A wonderful opportunity to settle into a great neighbourhood!

724 Clifton Drive, Oshawa
76 Switzer Drive, Oshawa
$749,000
4 Beds ⋅ 2 Baths ⋅ E14097496 MLS
Solid Ranch Style Bungalow In Great North-Central Oshawa. Attached Garage Features Drive-Thru To Backyard. Hedged Private Lot Backing Onto Green Space. Newer Basement Windows, Side Entrance To Basement From Garage. Lots Of Potential! Steps To Somerset Park. Mins To 401, 407, Durham College, Oshawa Airport, 45 Min Drive To Downtown Toronto Or Take The Go.

76 Switzer Drive, Oshawa
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