335 Bailey Drive

There's something especially appealing about a home lovingly cared for by the same owners for decades, and this wonderful bungalow offers a solid, well-maintained option for your next chapter. Inside, the main floor has a comfortable, straightforward layout with hardwood floors and plenty of natural light. A large front window brightens the spacious living room, while the adjoining dining room overlooking the backyard offers an inviting place to gather. The kitchen provides plenty of cabinetry and workspace, along room to enjoy more casual meals. Three good-sized bedrooms are situated on the main level and share a functional four-piece bathroom, creating a practical layout. Downstairs, the finished space adds plenty of flexibility. A generous rec room with a gas fireplace creates a cozy second living area, while an additional bedroom and four-piece bathroom provide useful space for guests, older children, or extended family. Laundry, a cold cellar, and a furnace room/workshop round out a lower level that makes good use of the available space. Out back, there's room to enjoy the outdoors in more ways than one. The deck overlooks a spacious lawn surrounded by mature greenery, with a garden shed for the tools and a large vegetable garden ready for someone who loves spending a little time with their hands in the dirt. With an attached garage, a well-established lot, nearby parks and bus routes, plus convenient access to commuter routes, the location keeps everyday necessities within easy reach. Move in and appreciate how well the home has been maintained, update it gradually, or bring your own ideas and make it entirely your own. Either way, this longtime family home is ready for someone new to put down roots.

When Lot Size Matters to you. Opportunities like this don't come along often! This spacious and beautifully maintained 4-bedroom family home offers exceptional value in a sought-after neighborhood. With parking for up to 6 vehicles and a large, private backyard with no rear neighbors, you'll have all the space your family needs. The outdoor oasis features a large above-ground pool (approx. 2020), multiple decks and patios, storage sheds, and plenty of room for entertaining, relaxing, and enjoying summer with family and friends. Inside, you'll find a bright, open-concept layout designed for comfortable family living. The welcoming foyer features a new front door in 2025, pot lights, with additional pot lighting in the family room and finished basement. The cozy family room showcases a beautiful wood-burning fireplace with an iron insert and offers a walkout to the fully fenced backyard. The spacious living and dining rooms flow seamlessly into the kitchen, creating an ideal space for both everyday living and entertaining. The primary bedroom features his-and-hers closets with convenient semi-Ensuite access to the main bathroom. Interior access to the garage from the foyer adds everyday convenience. This home has been lovingly cared for and updated throughout, including: Furnace, central air conditioning, and on-demand water heater (2021), roof (2023), paved driveway (2023), patio door (2020), front door (2025), and above-ground pool (approx. 2020).Ideally located within walking distance to shopping, schools, the recreation centre, public transit, and other everyday amenities, this move-in-ready home truly offers the perfect combination of space, privacy, location, and value. Don't miss your chance to make this exceptional family home your own! PS the big front tree is a beautiful Mulberry Tree. Basement also has a huge Storage area for all your stuff and more.

Welcome to 16 Brenda Boulevard - a beautifully maintained bungalow that checks every box for first-time buyers and savvy investors alike. This move-in ready home features a thoughtfully renovated kitchen, updated vanities, and an open-concept living and dining area filled with natural light and finished with new laminate flooring. Relax and unwind in the three generous upper bedrooms, while the updated 4-piece bath with jacuzzi tub adds a touch of luxury. Step through the kitchen walkout onto a stunning deck - the perfect spot for morning coffee, summer barbecues, and evening entertaining in your private fenced backyard. The lower level offers incredible bonus living space with a full-size pool table, and laundry -ideal for hosting or simply unwinding. Direct garage access, close proximity to schools, parks, and all amenities make this an easy yes. Opportunities like this don't last. *Some photos are virtually staged.

Bright & Welcoming 3+1 Bedroom Home in Family Friendly Location. Covered Front Porch Entry into Open Foyer with Convenient 2pc Powder Room. Traditional Spacious Kitchen with Easy Flow into Open Concept Dining & Living Rooms, with Lg Windows & Patio Doors that Walk Out to Raised BBQ Lounging Deck & Private Backyard. 2nd Level with 3 Good Size Bedrooms. Primary with Barn Board Feature Wall, Lg Window & Wall Closet w/ Organizer. Lg Hallway Storage & Linen Closets plus Main 4pc Bath. Finished Lower Level with Bedroom/Office, Laundry/ Utility Rm with Lg Window. Bright Spacious Rec Room w/ Sliding Doors that Walk Out to Stone Patio & Yard with Side Gate Perennial Gardens & Lots of Backyard Green Space for Family, Friends & Pets to Enjoy. 1 Car Garage w/ Opener, Storage Space & Workbench. Close to Schools, Park and Minutes from Downtown Orangeville with All Amenities & Activities.

Welcome To 44 Madison Ave In The Heart Of Orangeville. A Warm And Inviting 3level Backsplit Nestled In A Quiet, Family-Friendly Neighbourhood Just Steps From Parks, Trails, And Parkinson Centennial Public School At The End Of The Street, Offering JK Through Gr 8. This Home Offers An Excellent Opportunity For Growing Families, First-Time Buyers, Downsizers, Or Investors Looking To Get Into The Market.Step Inside To Find Bright And Spacious Principal Rooms Filled With Natural Light, New Windows Throughout (Except 2nd Flr Bath) Warm Hardwood Floors, And A Practical Layout Designed For Everyday Living. The Kitchen Offers Plenty Of Cabinet Space, A Functional Eat-In Area, And An Easy Flow Into The Dining Space, Making It Ideal For Family Dinners Or Entertaining. The Cozy Living Room Creates The Perfect Spot To Unwind. The Finished Basement Features A Spacious Rec Room, Convenient 2-Piece Bathroom, Laundry Room, Expansive Storage Space, And An Additional Room That Can Easily Function As A Fourth Bedroom, Home Office, Guest Room, Or Hobby Room. The Walkout From The Basement To The 3-Season Sunroom Adds Versatility And Creates A Seamless Connection Between Indoor And Outdoor Living.Outside Is Where This Property Truly Shines. The Fully Fenced Backyard Features A Brand-New Privacy Fence, Expansive Multi-Level Deck, 3-Season Sunroom, Above-Ground Pool, Mature Trees, And Plenty Of Green Space For Children And Pets To Enjoy. Whether You're Hosting Summer Bbqs, Relaxing Poolside, Gardening, Or Enjoying Quiet Evenings Outdoors, This Backyard Offers The Perfect Setting For Making Lasting Memories With Family And Friends.Located Close To Schools, Parks, Recreation Centres, Shopping, Restaurants, And Scenic Walking Trails, This Home Offers The Lifestyle So Many Buyers Are Searching For. With A Welcoming Community Atmosphere And Easy Access To Everyday Amenities, This Is A Fantastic Opportunity To Own A Well-Loved Home In One Of Orangeville's Desirable Family-Oriented Neighbourhoods.

Welcome to 67 Carlton Drive - Orangeville's best-kept secret! Perfectly perched on a beautiful corner lot in one of Orangeville's most family-friendly neighbourhoods, this charming home welcomes you with a spacious front porch and mature trees that create instant curb appeal. Steps from schools, parks, and places of worship, it's a dream location for families and commuters alike. Parking is a breeze with space for 4 vehicles, including a single-car garage. Out back, your private oasis awaits: a patio anchored by two steel gazebos, perfect for entertaining or relaxing, plus a garden shed for extra storage.This home has been meticulously maintained and thoughtfully updated from top to bottom. Move in with total peace of mind thanks to a brand-new roof (June 2026) with a transferable warranty. Major mechanicals are all in place, with a newer furnace, A/C, and hot water tank (2019), plus updated eaves, soffits, and fascia (2019). Inside, enjoy sleek laminate flooring on the main level (2016) and a beautifully renovated kitchen (2017), complemented by an updated main bathroom (2016) and a smart thermostat for effortless comfort and efficiency. The appliance list reads like a wish list: washer (2025), dryer (2026), central vac (2026), stainless steel dishwasher (2025), and stainless steel fridge, oven, and microwave (2017) - nothing left to do but move in! Looking for even more value? The finished basement offers incredible flexibility, with in-law suite or duplex potential and room for a private entrance - ideal for multi-generational living or extra income. Don't miss this rare opportunity to own a truly turn-key home in a location that has it all!

Home Sweet Home! If the walls could talk, they would actually sing many of the songs that were played here over the years! First time offered for sale, this family home is filled with fun memories and now it is ready to welcome a new family to continue the joy! This 4 level backsplit will impress you with the open concept main floor, renovated kitchen with breakfast bar and built-in appliances, extra large primary bedroom (originally 2 bedrooms converted into 1, can be converted back), 3 more bedrooms and a 4th level family "music room" where there were many years of songs played, dancing and togetherness! An added bonus is the storage space above the garage that was used to store snowmobiles and motorcycles! The large lot is fantastic - 60 ft x 100 ft - which provides an extra long and extra wide driveway, with enough parking for 6 cars! The location is fabulous! Walking distance to 3 schools, parks, public transit and more! Recently freshly painted and 2 upstairs windows replaced! Roof was re-shingled in 2025! Hot water heater is owned and included! Furnace was replaced in 2011! All of the appliances are included! Great value for the asking price!! This home is simply awesome and you can be the next lucky owner to live in it!

Charming Brick Bungalow in a Prime Orangeville Location. Welcome to this well-maintained all-brick bungalow offering the perfect blend of comfort, functionality, and location. Featuring 3 spacious bedrooms and 2 full bathrooms, this home is ideal for families, downsizers, or anyone seeking convenient one-level living with additional finished space. Step inside to discover a bright and inviting main floor with a practical layout designed for everyday living. The fully finished basement provides exceptional additional living space, perfect for a family room, recreation area, home office, gym, or guest accommodations. Outside, you'll appreciate the covered carport, a handy workshop for hobbyists or DIY enthusiasts, and a separate storage shed offering plenty of room for tools, lawn equipment, and seasonal items. The private yard provides space to relax, entertain, or garden. This home is just minutes from excellent schools, beautiful parks, walking trails, shopping, restaurants, and the vibrant downtown core. Enjoy the convenience of nearby amenities while living in a welcoming, family-friendly community. *For Additional Property Details Click The Brochure Icon Below*

Spacious. Versatile. Connected. Welcome to 27 Rustic Street in the heart of Orangeville-a beautifully maintained 3-level side split offering exceptional space, flexibility, and lifestyle. Ideally located within walking distance to schools and parks, and just minutes to shopping, recreation facilities, and downtown, this home also provides convenient access to Highways 9 and 10 for an easy commute.This thoughtfully designed home features 4 bedrooms and multiple living areas, ideal for growing families or multi-generational living. The garage has been converted to expand the main living space, creating an oversized living room along with a functional laundry/mudroom offering direct access to the backyard.The kitchen is well-appointed with stainless steel appliances, including a gas stove, and flows seamlessly into the dining area with a walk-out to the backyard deck-perfect for everyday living and entertaining.Upstairs, the primary suite has been reconfigured from two bedrooms into a spacious retreat complete with his and hers closets.The lower level offers excellent in-law potential with a separate entrance, two additional bedrooms, a 3-piece bathroom, and a laundry hookup. A second lower level with approximately 5-foot ceilings provides additional versatile space for storage or future use.Set on a fully fenced lot, the backyard is designed for both function and enjoyment. A fantastic opportunity to own a versatile home in a family-friendly community, offering both comfort and convenience in one of Orangeville's most desirable locations.

ATTENTION FIRST-TIME BUYERS, MULTI-GEN FAMILIES & SAVY INVESTORS! Positioned on a premium 50x109 ft mature lot with NO sidewalk for maximum parking and privacy, this solid detached bungalow is the ultimate "forced equity" opportunity in South Orangeville, why pay a premium for someone else's renovations when you can secure this similar structural footprint at an entry-level price point and build your own wealth.......Big-Ticket updates are already complete: New Roof 2023, New High Efficiency Basement Windows 2023, New Front Door 2023, and and main Kitchen updated in 2021 wth stone countertops, stainless steel appliances, gas stove. The main level boasts original hardwood flooring, a bright layout, 3 well - sized bedrooms, and a full washroom. ...........THE WEALTH BUILDING OPPORTUNITY: Standing out with a rare official legal 6 bedroom designation (MPAC), this home offers unbeatable layout flexibility. The massive lower level is an ideal candidate for a compliant Town of Orangeville 2 Bedroom Additional Residential Unit (ARU). ......The deep lot easily satisfies the local zoning mandate for a 1.2m wide pedestrian path and off-street tenant parking space. ......With a proven , established value ceiling for converted bungalow configuration on this street, 26 Cardwell is a perfect "blank canvas" to invest your own finishes and instantly drive up appraisal value. Unbeatable location close to top schools, parks, shopping, and commuter routes. Pictures are from previous listing. NOTE: Re-Imagined concept photos of the lower level are provided as a visual aid to showcase the incredible potential.

Get into the market with this charming detached home tucked away on a quiet cul-de-sac. From the moment you arrive, the curb appeal stands out. A newer driveway and carport lead to a covered front porch-an ideal spot to unwind. Out back, you'll find a fully fenced yard with mature trees, offering privacy and space for kids, pets, or entertaining. Commuters will appreciate the quick access to the bypass just seconds away. Inside, the main floor offers a bright eat-in kitchen complete with stainless steel appliances. The spacious living room sits at the rear of the home and walks out to a private sunroom overlooking the backyard-perfect for year-round enjoyment. Upstairs, there are three bedrooms, including two generously sized rooms with double closets, along with redone full 4-piece bathroom. The lower level is partially finished with a rec room, giving you additional flexible living space. Added comfort comes from supplemental heating and cooling units in the living room and primary bedroom and second bedroom. A solid opportunity for first-time buyers or families looking for space, privacy, and convenience. 15 minute walking distance to downtown Orangeville. Updates include: new ceiling with pot lights, electrical sockets & all light switches, new plumbing, attic insulation has been added to todays R Value, staircase carpet and railings, all closet doors, EV charger, both washrooms redone, roof approximately 11 years old, sunroom, carport and driveway approximately 12 years old, AC/heating units, new lighting, and fresh paint throughout. Heat pumps are very efficient & the hydro bill is very reasonable.

Welcome to this beautifully updated family home, perfectly situated in one of Orangeville's most sought-after neighborhoods! Enjoy the convenience of being just minutes from top-rated schools, shopping, dining, the hospital, and multiple parks-all while having effortless access to Highway 10 and Highway 9, making commuting a breeze.Step inside to discover a spacious and inviting layout with thoughtful upgrades throughout. The large primary suite is a true retreat, featuring a cozy fireplace, spa-like en-suite bathroom, and ample closet space. With two additional bedrooms and a total of three bathrooms, there's plenty of room for the whole family to thrive.The heart of the home is the modernized kitchen, complete with a stunning quartz countertop with waterfall edge, sleek cabinetry, and updated appliances-perfect for cooking and entertaining. New luxury vinyl flooring flows throughout, adding a fresh and stylish touch.Need more space? The fully finished basement provides endless possibilities-whether it's a home office, playroom, gym, or media lounge. And for the ultimate relaxation experience, enjoy your very own private sauna, perfect for unwinding after a long day!Enjoy the best of both worlds with nature and convenience at your doorstep! This home is within walking distance of Island Lake Public School, Island Lake Conservation Area, local restaurants, vibrant bars, and the charming downtown core.Don't miss your chance to own this move-in-ready gem in a fantastic community! Book your showing today!

Welcome to 344 Adams Court, an exceptional family home nestled in one of Orangeville's most sought-after neighbourhoods. Tucked away at the end of a quiet court, this beautifully updated property offers a safe, family-friendly setting where children can play and neighbours quickly become friends.Situated on a desired pie-shaped lot, the backyard has been thoughtfully designed for both relaxation and entertaining. Enjoy summer evenings on the spacious composite deck overlooking the private yard, complete with a poured concrete patio, gazebo, and beautifully finished outdoor spaces that create the perfect extension of the home. Inside, you'll find a bright, open-concept floor plan that seamlessly blends comfort with modern elegance. The heart of the home is the stunning, newly renovated kitchen featuring sleek cabinetry, premium appliances, and a large centre island designed for gathering with family and friends. The adjoining living room offers a warm and inviting atmosphere with a cozy fireplace, custom built-in wall unit, and abundant natural light throughout.The newly finished basement (2026) provides exceptional additional living space, complete with new flooring, trim, and a beautifully updated bathroom, making it ideal for a family recreation room, home office, gym, or guest accommodations. Pride of ownership is evident throughout, with virtually every aspect of the home thoughtfully updated. Recent improvements include a concrete driveway (2022), pathway and composite deck (2022), backyard shed (2022), roof (2021), front windows (2021), primary bedroom windows (2021), front entry door (2021), sump pump (2023), gazebo (2023), custom entertainment wall with built-in pot lights and under-cabinet lighting, and the fully finished lower level completed in 2026. Offering timeless finishes, exceptional outdoor living, and an unbeatable location within one of Orangeville's premier communities, 344 Adams Court is the perfect place to call home.

Beautiful Detached home Located In A Highly Desired Neighbourhood! Steps to Island Public School, Plaza and Headwaters Health care. Open Concept Main Floor Living Area W/ Hardwood Floors & Pot Lights, Stainless Appliances, Granite Counters, Pantry & Walk-Out To Backyard. Oak Staircases Throughout. Primary Bedroom W/ 4-Piece Ensuite & Walk-In Closet, 2nd Floor Laundry Room W/ Extra Shelving & Storage. Gas Fireplace In Basement. No Sidewalk-Lots of parking. Good size 1.5 garage. Garden shed for extra storage.

Welcome to 337 Broadway St, a spacious detached home in the beautiful and growing community of Orangeville! Thoughtfully updated to offer exceptional flexibility, this property is an ideal opportunity for growing families, multi-generational households, or investors looking for extra income potential.The main level features four bedrooms, providing plenty of space for family, guests, a home office, or whatever your lifestyle demands. Recent renovations have added even more functionality, while the finished basement offers the potential for completely separate living with excellent privacy-perfect for extended family, older children, guests, or additional living space.Enjoy a central Orangeville location with convenient access to shopping, dining, everyday essentials, recreation, and major routes. Families are well served by local schools including Orangeville District Secondary School, Westside Secondary School, and several elementary schools. Outdoor enthusiasts will love having Orangeville's extensive trail network, Island Lake Conservation Area, Harvey Curry Park, and Fendley Park within the community. Alder Recreation Centre and Tony Rose Memorial Sports Centre provide even more options for swimming, skating, fitness, and year-round activities.With space, versatility, privacy, and a fantastic Orangeville location, this home checks all the boxes. Act now before this opportunity is gone!

Nestled in a prime central town location, this quaint and well-maintained bungalow offers the perfect blend of historic character and incredible potential. The home welcomes you through a charming enclosed front porch, leading into a spacious living room highlighted by a large front picture window that floods the space with natural light. Beneath the existing carpeting in the living and dining rooms lies original hardwood flooring waiting to be revealed. The main floor features two comfortable bedrooms and a functional rear kitchen that overlooks an impressive 52' x 140' lot. For those who love the outdoors, the rear 3-season sunroom provides a peaceful retreat with a direct entrance to the home. The partially finished basement adds significant living space, featuring a recreation room, wet bar, powder room, and guest space. Practicality abounds with a separate laundry room equipped with a shower stall, a dedicated workshop, a cedar closet, and a cold cellar. Car enthusiasts or hobbyists will appreciate the double-deep tandem garage and ample parking. With updated main-level windows and a location that puts the Orangeville Theatre, local shops, restaurants, and professional services just a short stroll away, this home is a rare find for those seeking convenience and classic charm.

CHARMING CENTURY HOME STEPS FROM DOWNTOWN ORANGEVILLE! Full of character and warmth, this 2-bedroom, 1-bathroom home offers a wonderful opportunity for first-time buyers, downsizers, or investors in a fantastic central location. Built in 1890, this inviting century home blends small-town charm with everyday convenience, just steps from downtown Orangeville's shops, restaurants, cafés, parks, and amenities, while also offering quick access to the bypass for commuting. Inside, the home has a cozy and welcoming feel, with comfortable living spaces and the charm you would expect from an older Orangeville property. The kitchen offers great everyday function, while the two bedrooms provide flexibility for a small family, couple, home office setup, or investment use. The backyard is a true highlight, offering a large, fully fenced, private, and tranquil outdoor space surrounded by mature trees. Enjoy the lovely perennial garden, relax on the new deck, or gather with family and friends under the gazebo. With plenty of room to enjoy the outdoors, this property offers a peaceful retreat right in the heart of town. A private driveway and separate garage provide added convenience, storage, and functionality. Whether you are looking to enter the market, add to your investment portfolio, or enjoy a character-filled home in a walkable Orangeville location, this is a wonderful opportunity not to be missed. See Additional Photos for Video Tour!