Simcoe & Rossland Real Estate for Sale

An architectural masterpiece. A legacy of craftsmanship. A home without equal. Set on one of Oshawa's most coveted streets, this extraordinary 4 bedroom residence is a remarkable piece of local history, originally built in 1918 for John Stanton of the Pedlar People Company. More than a century later, its distinctive architecture, craftsmanship remain as captivating as ever. This home immediately commands attention. A beautifully manicured landscape creates a grand approach, culminating in the home's unforgettable iconic moon front door. Step inside & discover generously proportioned principal rooms, 9 foot ceilings, 10" plaster crown moldings, a wood burning fireplace, built in bookshelves, a swing door, hardwood flooring, coffered ceilings, unique lighting, all creating an elegance in a home where craftsmanship takes centre stage. Glorious refinished wood trim frames the interiors, while Dutch & leaded windows bring a sense of warmth & artistry to the living spaces. The architectural story continues overhead with standing-seam copper roofs & copper troughs, complemented by a distinctive hand-hammered copper sink in the custom kitchen. Ascending to the 3rd storey, a private bedroom & loft offers a flexible space that could serve as a guest suite, office, or secluded hideaway. The lower level extends the home's versatility with a basement workshop & dedicated office space, along with a truly unique soundproofed room. Ideal for a podcast studio, recording space, creative studio, or media room. Beyond the home itself, the grounds boast a private hot tub, premium artificial turf & meticulously manicured gardens, which create an outdoor oasis. And then there is the garage, an architectural statement in it's own right. The spectacular 20'x32' garage with oversized automatic-carriage doors, provide a combination of functionality & visual impact. This is a residence defined by the extraordinary. Some homes are remembered. This one is unforgettable.

Welcome to 214 Winona! Set on a picturesque, quiet street in a convenient location, this charming home sits on an oversized lot with plenty of privacy. A large driveway and inviting front porch welcome you inside to a generous foyer that leads into the spacious, family-sized dining room - ideal for hosting! The updated kitchen features stainless steel appliances, an island with seating and storage, and plenty of cabinet and counter space. The cozy living room offers a gas fireplace, faux wood beams, and a lovely view of the front yard - the perfect spot for family movie nights. The primary retreat boasts laminate flooring and a large double closet, while two well-appointed secondary bedrooms each feature generous closets and large windows. A newly renovated 4-piece bathroom completes the main level. Step outside to the oversized, fully fenced backyard offering plenty of privacy and space to enjoy. With a walkout from the home, this is the perfect setting for summer BBQs, fall bonfires, or for kids and pets to play! Ideally located close to transit, Oshawa Centre, shopping, restaurants, Hwy 401, golf courses, and more. A great opportunity in a safe, family-friendly location!

Welcome to a charming and exceptionally well-cared-for home in one of Oshawa's most desirable and established neighbourhoods. Tucked away in a quiet, clean, and family-friendly community where homeowners tend to stay for years, this property offers the perfect blend of comfort, convenience, and versatility. Enjoy easy access to highly regarded schools, parks, golf, amenities, and major highways, all while coming home to a welcoming neighbourhood setting. Step inside to a bright and inviting main level featuring a lovely open-concept layout, an updated kitchen, and an abundance of natural light. Three spacious bedrooms upstairs are complemented by an updated bathroom, providing a comfortable and functional layout for families. The home's split-level design creates exceptional versatility, offering options for growing families, multigenerational living, or those looking for additional space and flexibility. The lower level is a standout feature, complete with a brand-new updated kitchen, living room, bathroom, and bedroom. With a walkout and separate entrance, this space offers the potential for a self-contained living area, extended family accommodations, guest space, or rental opportunities, subject to applicable approvals. A fantastic option for those seeking flexibility now and into the future. Outside, the impressive 90' x 125' double-wide lot is a rare find, offering incredible space and endless possibilities. Whether you're looking to move in and enjoy, accommodate extended family, explore additional income potential, or customize the home to suit your vision, this property offers the space and opportunity to make it your own. A wonderful home in a location people are proud to call home.

In Oshawa's Centennial Neighbourhood, This Completely Self-Contained 3+3 Bedroom Bungalow Offers An Amazing Opportunity For Buyers Looking For Space, Flexibility, And Long-Term Potential. With 2 Kitchens, Separate Entrances, A 1-Car Garage, And Parking For 6+ Cars, The Layout Is Well Suited For Extended Family, Multi-Generational Living, Or Investors. The Main Floor Features Hardwood Flooring, 3 Bedrooms, Laundry, A 4-Piece Bathroom, And An Updated Kitchen With Stone Counters And Vinyl Flooring, Giving The Upper Level A Clean And Functional Everyday Layout. The Basement Adds Serious Versatility With 3 Additional Bedrooms Featuring Egress Windows, A Second Kitchen, Living Room, 3-Piece Bath, And Laundry, Creating A Lower Level That Can Support A Variety Of Living Arrangements. Outside, The Large Backyard Offers Patio Space, Room To Enjoy, And A Garden Shed For Extra Storage. Close To Amenities And Set In A Mature Centennial Location, This Property Gives Buyers More Than A Bungalow; It Gives Them Options.

There's no place like home; and this area has so much to offer! Welcome to 699 Grierson St., Oshawa, a 3-bedroom bungalow in an established neighbourhood with Dr. S.J. Phillips Public School and O'Neill CVI as the currently assigned public schools. Backing onto the Michael Starr Trail, this carpet-free home gives you direct access to one of Oshawa's paved urban trails. Inside you'll find an updated kitchen and washrooms, hardwood flooring and the convenience of bungalow living with the principal living spaces and bedrooms on the main floor. The lower level adds even more living space with a rec room and fireplace. With so many of the big-ticket items already taken care of, there is plenty to appreciate here. Key Dates: Freshly painted ~2026; Main washroom ~Mar. 2025; Front porch railings ~2021; Furnace ~2020; Air conditioner ~2017; Water tank ~2022; Screen doors ~2021; Windows ~2016; Kitchen ~2016; Shingles ~2007; replaced caps ~2026; New driveway ~2020; Deck ~2016; Hardwood floors ~2023; Ducts cleaned Nov. 2025.

A home that grows with you. This charming brick bungalow in the quaint & historic community of Centennial offers the space, flexibility & backyard you've been waiting for. Tucked away on a quiet street, this lovingly maintained 3-bedroom + 1, 2-bathroom home has an easy, comfortable flow that makes sense. Freshly painted throughout, the main floor connects the kitchen, dining room & living room effortlessly, perfect for everything from quick weekday dinners to hosting friends and family on the weekend. Gorgeous baseboards and plenty of built-ins add character and charm, while the abundance of storage keeps everyday life organized. The oversized primary bedroom is a true retreat, with plenty of windows bringing in natural light. And when the weather turns chilly, light the natural gas fireplace, grab a blanket & settle in for a movie night without ever leaving bed. Because sometimes the best nights happen right at home. Need more space? The basement gives you room to spread out, w a family room, an additional bedroom for guests, teens, a home office or whatever life requires, plus a dedicated laundry room. And then there's the backyard. The great-sized lot gives you plenty of room to entertain, let the kids run, enjoy dinner under the gazebo or simply relax with a glass of something delicious while the day winds down. Add a pool or trampoline & you've got the makings of years of backyard memories. And you'll know fall has officially arrived when the walnuts start dropping from the tree! A garage? Bonus! Plenty of room for a small car, tools, bikes & all those decorations you swear you're going to use again next year. Let's swoon a min over the perfect pet-friendly 4-season Northway Court Park. Walking trails, soccer field, a hill perfect for tobogganing. This is the kind of home that gives you room to live now and possibilities for what's next. It's comfortable for your first chapter, flexible enough for your family years and manageable enough for what's to come.

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.

Registered as a Two-Unit Dwelling with the City of Oshawa and situated on a 50 by 122 foot lot in a great neighbourhood with 2 furnaces and 2 Hot Water Tanks, welcome to 858 Grierson St., Oshawa! The main floor of this brick bungalow offers charming arched doorways and a wide east facing, front window to let the morning light flood the living and dining rooms. Separately laid out at the back of the home are two inviting bedrooms just off the hall with access to the updated bathroom. The kitchen was also redone with quartz counters, a tiled backsplash, new stainless fridge and range, and a window over the sink. The 4 piece bath was rebuilt with a new tub, tiled surround, vanity, toilet, lighting and floor. The lower unit has its own side entrance and stays bright under the many above-grade windows. It holds a 22 foot living and dining area, its own kitchen, a bedroom, a second 4 piece bath finished to the same standard, and the 2 units are finished with a laundry room. Two gas furnaces, one per level, installed 2014/2015. Roof 2015. 2 hot water tanks as well, which are owned. Luxury vinyl plank runs through both levels, the paint is fresh, and the light fixtures are new throughout. A private drive runs the full length of the house offering four spaces in total. The yard behind it is fenced on three sides with mature trees along the back and a concrete patio for evenings watching the sunset at the end of a great day. Quiet centrally located street, walkable to Beau Valley Public School and North Oshawa Park, minutes to Ritson Rd N and the Costco plaza it offers, with Lakeridge Health Oshawa close by, and both the Oshawa Centre and Highway 401 a short drive south. This is the perfect home to get into the market with, living upstairs while renting out the basement, or rent out both!

Welcome to 100 Arlington Ave. Located in the highly sought after O'Neill Community. This fully updated one and a half storey cottage bungalow offers 3+1 bedrooms and 2 full bathrooms. Many improvements including a new 10' x 16' shed and base '25, eaves '25, kitchen '25, 3 main doors '24, new front porch, stairs and ceiling '24, sunroom windows and flooring '24, furnace '18, floors throughout 18' and roof '15. Unspoiled basement with 6ft height ceilings. With parking for 3-4 cars. Enjoy the 3-season sunroom and the fully fenced private backyard which offers an oversized deck and two patios. Steps to the golf course, shopping, schools (k-8 and high school), Alexandra Park and Lakeridge Hospital. Simply move in and enjoy!

**Legal Duplex! Attention Investors & Multi-Generational Families!** Welcome to this spacious 2+2 bedroom legal duplex situated on a large corner lot in a mature North Oshawa community. Offering two self-contained units, each with its own laundry, this property is an excellent opportunity for investors, extended families, or buyers looking for added income potential. The upper unit features a bright and spacious living room with a large picture window overlooking the front yard and beautiful hardwood flooring that continues into the dining room. Garden door leads to a relaxing sunroom with peaceful views of the backyard. The generous kitchen offers a custom backsplash, large pantry, and plenty of cupboard and counter space. Two well-sized bedrooms and a 4-piece bathroom complete the upper level. The lower-level unit offers a separate side entrance, above-grade windows, a comfortable living room, eat-in kitchen, two bedrooms, and a 3-piece bathroom. Ideally located just steps from parks, schools, public transit, Lakeridge Health Oshawa, grocery stores, and big-box shopping. Recent updates include: roof (2015), furnace (2022), central air conditioning (2022), eavestroughs (2022), basement washer/dryer (2023), and driveway (2024). A fantastic opportunity to own a versatile income property in a convenient and established Oshawa neighbourhood!

OPEN HOUSE SUNDAY SEPT 20 2-4PM **This true ranch-style bungalow on a premium lot features a gorgeous custom kitchen with tall cupboards, overlooking the backyard with walk out to a large breezeway that gives you access to the covered patio, front of home and garage. The main floor features a gas fireplace, distressed hardwood flooring, large picture windows throughout, crown moulding & upgraded baseboards. 3 Main-floor bedrooms (zero stairs!). Need more? There are 2 additional generous sized bedrooms in the lower level, a massive open concept recreation room with many windows flooding the area with natural light, vinyl plank flooring, electric fireplace, distressed wood beam framing that leads to a full size kitchenette and eat-in area. Turn-key multigenerational living: The basement has a separate entrance via the private breezeway: think in-laws, adult kids, or an epic guest suite, basement apartment potential for extra income or just enjoy the space for yourself! Plus a gorgeous private fully fenced backyard with a large garden shed, covered porch, perennial gardens, mulberry trees, grapes, raspberry bushes and mint for those summer time mojitos. The deep double driveway can accommodate 5-6 cars so you never have to worry about parking. No side walk to shovel either! Situated in a fantastic niche community walking distance to Sunset Heights PS, grocery shopping, restaurants to tempt your taste buds. The Hospital is a 5 minute drive away as well. If you enjoy walking a lovely park with trails is just a short walk down the street from the property. The garage features high ceilings and epoxy glazed flooring with storage shelving on the walls for all your extras. Furnace'22. See Feature Sheet for more details & updates

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.

COME - LOOK - LOVE! This spacious North Oshawa Home located on a Quiet Court is the perfect place to call HOME! Offering generous living space, excellent storage, and an impressive detached garage, this home is perfect for families, hobbyists, or anyone looking for room to grow. The bright, spacious kitchen features ample cabinetry and plenty of counter space, with a convenient walkout to the deck and peaceful backyard-perfect for morning coffee, outdoor dining, or entertaining.The L-shaped living and dining area features beautiful hardwood floors, 5-panel bow window and plenty of space to relax or host family and friends. Upstairs, the original three-bedroom layout was thoughtfully converted to two bedrooms, providing additional comfort and versatility. A convenient 4-piece bathroom completes the upper level.The ground floor offers a welcoming main entry, direct access to the single attached garage, a large laundry area with abundant storage, and a 3-piece bathroom with a double shower. A rear entrance provides easy access to the backyard and the standout feature of this property: a 2+ car detached garage that is insulated, heated, and equipped with hydro-ideal for a workshop, storage, vehicles, or hobbies.The finished basement adds even more living space, featuring a comfortable recreation room with a gas fireplace and a separate office. Large windows bring in plenty of natural light, creating bright and welcoming spaces throughout the year.A quiet location, generous living space, multiple bathrooms, finished basement, attached garage, and an exceptional heated detached garage make this a home worth seeing.

Golf course views, total privacy, and curb appeal! Nestled on a quiet, no-thru street and framed by towering mature trees, this well maintained 3-bedroom bungalow is the ultimate private sanctuary. From the moment you step onto the charming front porch and walk through the updated interior, the home's exceptional pride of ownership and care are immediately evident. The inviting layout features practical principal rooms, a fully renovated main bathroom completed in 2023, and a bright, welcoming atmosphere throughout. The finished lower level adds valuable living space with a comfortable rec room, as well as a newly created basement bathroom and laundry room. Enjoy peaceful mornings and relaxing evenings in the screened-in three-season room overlooking the private backyard. Countless updates provide peace of mind, including all new electrical (2019), new plumbing (2021), furnace (2023), and a durable metal roof (2012). Septic pumped August 2026. A rare opportunity to own a beautifully updated bungalow in a serene setting where comfort, privacy, and pride of ownership come together effortlessly.

Welcome home to 47 Churchill Ave., a charming and cozy bungalow tucked away on a quiet cul-de-sac in a desirable pocket of the Centennial neighbourhood, situated on a spacious corner lot with incredible potential for families, investors, or multi-generational living! This well-maintained 3 bedroom, 2 bathroom home offers original hardwood flooring throughout the upper level and a warm, inviting layout full of character. While the home has a more classic interior, it has been lovingly cared for by the same owner for 40 years and provides the perfect opportunity to move in, renovate over time, or customize to your taste. Outside, you will find standout features rarely offered together: an inground pool, two separate driveways and two garages (one attached and one detached); providing ample parking, storage and workshop space. The separate entrance adds excellent flexibility and along with the two driveways, creates strong potential for a future in-law suite or second unit setup, making this property an attractive investment opportunity. Conveniently located close to schools, parks, shopping, transit and amenities, the property combines comfort, functionality and long-term potential in an established Oshawa neighbourhood!

Nestled within one of The Glens' most coveted ravine settings, this extraordinary six-bedroom bungalow is a private sanctuary where luxury and nature exist in perfect harmony. Surrounded by mature trees, lush landscaped gardens, and the calming sounds of the ravine, this remarkable property offers an exceptional sense of tranquility and seclusion. A serene zen pond and breathtaking panoramic ravine views create an unforgettable backdrop in every season. Thoughtfully designed for sophisticated family living, this meticulously maintained residence showcases over 4,400 square feet of beautifully appointed living space, where timeless elegance meets everyday functionality. From the impressive interlock driveway to the expansive walk-out lower level, every detail reflects pride of ownership and quality craftsmanship. At the heart of the home, the chef-inspired kitchen is designed to impress, featuring granite countertops, a gas cooktop, double wall ovens, and an inviting breakfast bar that seamlessly connects family gatherings with effortless entertaining. The grand foyer welcomes you into a spectacular sunken living room, where oversized windows frame the surrounding ravine and bathe the space in natural light. The walk-out lower level extends the home's exceptional living space, while a bright and beautifully finished two-bedroom in-law suite with a separate entrance provides outstanding flexibility for multi-generational living, extended family, or distinguished guests. Step outside into your own resort-inspired oasis, where the luxurious Hydropool swim spa invites year-round relaxation and wellness. Whether entertaining on the terrace, enjoying peaceful mornings overlooking the ravine, or unwinding amidst the beautifully landscaped grounds, every moment here feels like a private escape. This is more than a home-it's an extraordinary lifestyle in one of The Glens' most prestigious settings.

Set on a rare 100 x 175 ft lot in Oshawa's established Bessborough Park neighbourhood, just steps from the nearby ravine and surrounded by mature trees. Fully renovated from top to bottom, this home combines modern finishes with the space and privacy that make properties like this so desirable. Inside, the main floor opens into a bright open-concept living, dining, and kitchen space filled with natural light. Seamless recessed pot lighting throughout gives the home a clean modern feel, while the updated kitchen features sleek cabinetry, stainless steel appliances, and a generous island that naturally becomes the heart of the home for everyday living and entertaining. Upstairs you'll find 3 well-sized bedrooms and 3 bathrooms, while the fully finished basement with its own separate entrance adds valuable flexibility with 2 additional bedrooms, a kitchen, and a separate living area-ideal for extended family, multi-generational living, or private guest space. The home also includes two separate laundry areas with two washers and two dryers, adding convenience for larger households. The backyard truly sets this property apart. Sitting on an impressive 100 x 175 ft lot, it offers outdoor space rarely found in the area, with privacy created by the surrounding greenery and endless potential to relax, entertain, or create your own outdoor retreat. Located in a family-friendly neighbourhood close to parks, schools, and convenient highway access for commuters. Homes with this level of renovation on a lot of this size in Bessborough Park rarely come available-and this one is best experienced in person to appreciate the space and setting.