Fully finished 4-level sidesplit on a premium 60 x 130 ft lot in one of Orangeville's most desirable, mature neighbourhoods. This is not your typical subdivision setting. Towering trees, pride of ownership and a quiet, well-kept streetscape create a private, established feel rarely found in newer areas. Ideally located close to schools while maintaining a peaceful residential atmosphere. Ample driveway space provides parking for up to 5 vehicles, ideal for growing families and guests a like. Inside, the home offers a versatile layout designed to suit a variety of family dynamics. The main level features a stunning open concept living, dining and kitchen space highlighted by a vaulted ceiling and an abundance of natural light, creating a bright and spacious central gathering area. Upper and lower bedroom options provide flexibility for growing families, guests or multi-generational living. The lower level includes above-grade windows, a second family room with a gas fireplace, a private bedroom and bathroom, offering excellent in-law or teen retreat potential. The finished basement adds even more adaptable space perfect for a home gym, office, playroom or media room. Step outside into a south facing backyard oasis on this fully mature, oversized lot. Enjoy the in-ground pool complete with a new heater, extending your swimming season for months at a time. The expansive yard still offers plenty of manicured lawn space for recreation, entertaining and everyday enjoyment. A rare opportunity to own a spacious home on a large lot in a sought-after Orangeville location.More details
Welcome to 17 First Avenue, a truly stunning red brick Century Home, built in 1933 and rich with timeless charm. Perfectly located in the heart of downtown Orangeville, this home is just steps to the town's best restaurants, cafes, and shops, offering walkable convenience with small-town charm. Set on an impressive 65 ft x 155 ft lot, the property features mature trees, lush gardens, and a massive fully fenced backyard backing onto a laneway that provides many opportunities including adding a detached garage or garden sweet with an in-law apartment- a rare find in such a prime location. Inside, you'll find nearly 2,500 sq ft of beautifully maintained living space with hardwood flooring throughout. The home offers 4 large bedrooms and 2 fully renovated bathrooms. The newly renovated kitchen is a showstopper, featuring cream-coloured custom cabinetry, quartz countertops, and a picturesque view overlooking the backyard. The back deck is brand new, this is the perfect space to enjoy the warm Summer months! The spacious dining room comfortably seats 8 guests and is ideal for hosting family and friends. The living room and family room are warm and inviting, each with a gas fireplace and tasteful updates that blend character with modern comfort. Just off the living room, a charming sunroom provides the perfect spot for morning coffee or quiet reading. The finished basement adds exceptional value, complete with a cozy movie theatre room with a third gas fireplace and a dedicated craft room. This home is full of warmth, charm, and thoughtful updates. A true haven for century home lovers seeking character, space, and an unbeatable downtown location.More details
This bright and welcoming 2-bedroom condo is designed for comfortable, easy living. The open-concept layout seamlessly connects the main living spaces, while the kitchen-finished with durable vinyl flooring-offers generous counter space and plenty of cabinetry, all overlooking the combined living and dining area, finished with laminate flooring. From here, step out onto your private balcony, an ideal spot to relax and enjoy some fresh air. The spacious primary bedroom features laminate flooring, a large walk-in closet, and convenient semi-ensuite access to the 3-piece bathroom. The second bedroom is filled with natural light thanks to its large window, making it perfect for guests, a home office, or additional living space. An in-suite laundry area with extra storage adds to the home's everyday convenience. For added convenience, the locker (No. 32) is located on the same level - just down the hall. Ideally situated close to downtown, shops, restaurants, theatre, parks, and everyday amenities. Condo fees include Rogers Internet & Cable contract. Extra visitor parking is available onsite. *some photos have been Virtually Staged*More details
Welcome to 218 Elizabeth Street - a beautifully renovated detached brick bungalow with a basement apartment nestled on a generous 50 ft x 142 ft mature lot. This impressive property features a newer roof(2020), a private inground pool, lush landscaped gardens, and an interlocking stone patio, creating the perfect outdoor oasis. A large workshop on-site offers incredible potential. Inside, the main floor has been professionally updated in 2025 with new hardwood flooring, a modern kitchen with quartz countertops and stainless steel appliances, three spacious bedrooms with built-in closets and new windows overlooking the mature treed property, a new sleek three-piece bathroom, and the convenience of main floor laundry. The lower level offers a fully self-contained apartment with its own private entrance - ideal for rental income or multi-generational living. This suite includes two bedrooms, a full kitchen with granite countertops, a three-piece bathroom, and in-unit laundry. Located in a family-friendly neighborhood, you're within walking distance to schools, parks, restaurants, and more. Whether you're a first-time homebuyer or an investor seeking a turn-key opportunity, this home offers exceptional value and versatility.More details
Discover an exceptional opportunity to own 25 acres of clear, flat, and highly usable land in the sought-after community of East Garafraxa. This beautiful parcel offers the perfect canvas to build your custom dream home, private estate, or future country retreat. Currently being actively farmed, the land benefits from open, workable acreage with excellent soil conditions and minimal clearing required-making it ideal for a variety of agricultural or residential uses. The level topography provides ease of development and flexibility in designing your ideal layout. Ideally situated just north of Orangeville, this property offers the perfect balance of peaceful rural living while remaining within a short drive to shopping, schools, dining, and essential amenities. Enjoy the tranquility of the countryside without sacrificing convenience. A Vendor Take-Back (VTB) option may be available for a limited time, presenting added flexibility for qualified buyers. Please note: Do not walk the property without a confirmed appointmentMore details
Welcome to this breathtaking countryside estate, a true gem set on 28 acres of picturesque land. This stunning property boasts mature trees, meticulously designed perennial gardens, and views of rolling hills. Offering 4,963 square feet of above-grade living space, plus a fully finished walkout basement, this luxurious home is designed for both entertaining and everyday comfort. Step inside to find 9 spacious bedrooms and 7 bathrooms, ensuring ample space for family and guests. The primary suite is a true retreat, complete with its own private balcony, a sunlit sitting room with panoramic windows, spacious walk-in closet, and a 5-piece ensuite. The main level showcases multiple walkouts to an expansive deck, where you will find a beautifully landscaped inground pool, surrounded by stone and lush gardens. Enjoy the serene surroundings from the charming gazebo, an ideal spot for relaxation. At the heart of the home, the large eat-in kitchen is a chefs dream, complete with a central island and an open-concept layout ideal for both everyday dining and entertaining. Additionally, the home includes a separate entrance to the second storey, which could serve as a nanny or in-law suite, providing added privacy and flexibility for extended family and guests. This estate is as practical as it is beautiful, featuring a triple-car garage, a cedar shingle roof, and an energy-efficient geothermal heating and cooling system. A carriage barn on the property adds character and offers additional storage or potential for various uses. Offering the perfect blend of luxury, comfort, and natural beauty, this extraordinary estate invites you to embrace the tranquility of country living. Do not miss your opportunity to make this exceptional home your own!More details
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, kitchenette, powder room, and a guest bedroom area-ideal for an in-law suite or extended family. 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.More details
Set in sought-after Purple Hill, this home offers a neighbour that's hard to come by. Quiet, established, and located beside Island Lake Conservation Area, it brings a sense of privacy and calm that you notice right away. Inside, the home has been thoughtfully updated and is move-in ready with a layout that works for everyday living. The main level flows naturally between the living and dining areas, creating a bright, comfortable space for both daily routines and entertaining. The refreshed kitchen features updated finishes and appliances, and opens into an eat-in area with a walkout, making indoor and outdoor living feel connected. Upstairs, three well-sized bedrooms are served by an updated four-piece bathroom, offering a clean and cohesive feel. The ground level adds flexibility with a spacious family room with a walkout, two additional bedrooms, and an updated three-piece bathroom, ideal for guests, extended family, or a home office setup. The lower level offers laundry, mechanicals, and plenty of storage, along with a large crawl space. Outside, the fully fenced backyard is a great size for families, pets, or simply enjoying the outdoors. With Purple Hill Park nearby and easy access to trails and green space, this location balances convenience with a more peaceful pace. Recent updates create a clean, consistent look throughout, including new flooring, full interior repaint, refreshed kitchen and bathrooms, and updated stair details. Updates extend beyond the interior, with new windows, exterior improvements, and recent servicing already taken care of. If you're looking for a move-in ready home in a quiet, established neighbourhood close to nature and amenities, this could be the one for you.More details
Welcome to 255 Kensington, a beautifully laid-out home in a highly desirable neighbourhood. The main floor offers a seamless blend of everyday comfort and functionality, featuring a combined living and dining room ideal for entertaining. The kitchen includes a bright breakfast area, perfect for casual mornings, while the inviting family room with an electric fireplace creates a warm space to unwind. With two walk-outs to the backyard, indoor-outdoor living is effortless.Upstairs, you'll find three well-proportioned bedrooms, offering plenty of space for family or guests. The unfinished basement presents a blank canvas, ready for your personal touch-whether you envision a home gym, recreation space, or additional living area.A wonderful opportunity to settle into a sought-after community and make this home your own!More details
Gorgeous, immaculately maintained, move-in-ready, spacious, 1 bedroom + den offering flexibility for a home office, reading nook, 2 bathroom Condo, located near the heart of the charming town of Orangeville. Condo has been newly painted throughout. Large spacious kitchen features lots of cupboard space and open to the dining room and living room. Walk out from the living room to a private balcony, great to sit outside and relax. Convenience of in-suite laundry. Large primary bedroom with 4 piece en-suite & spacious closet. This Condo combines both comfort and convenience. Included with the Condo are a private parking space, storage locker, and convenient visitor parking. Positioned along Broadway Street and within easy walking distance to Orangeville's downtown core, cafes, shops, restaurants, parks, schools, recreation centers, shopping and all the amenities you would every need. A great place to live and a great opportunity to get into the market and own your own home.More details
Step into downtown Orangeville living at its best. 5 Armstrong Street, Unit 13 is a bright, stylish one level stacked townhouse just steps from Broadway's cafes, bars, shops, festivals, and small-town charm. With 2 bedrooms, 2 full baths, and a smart all-on-one-level layout, this home delivers comfort, convenience, and modern appeal. Enjoy hardwood flooring throughout, a sun-filled living area, and a kitchen loaded with storage - complete with a 12.5-foot granite peninsula that's perfect for entertaining or everyday meals. The primary suite features a private 4-piece ensuite and walk-in closet, while the second bedroom offers ideal space for guests or a home office. Added perks include in-suite laundry, 1 exclusive parking spot, ample visitor parking and a private terrace for morning coffee or evening unwinding. Built in 2011 and part of a well-managed community, this home puts you minutes from restaurants, parks, transit, and year-round events. It's the perfect blend of downtown energy and easy living. Live where Orangeville shines - in one of its most desirable condo communities.More details
Historic Elegance Meets Modern Luxury at 9 Wellington St. Experience the perfect blend of century-old charm and high-end functionality in this grand 1926 home located on one of Orangeville's most prestigious streets. Spanning an impressive 4201 sq ft, this residence features 2 kitchens with a self-contained apartment, and a total of 6 spacious bedrooms and 5 bathrooms, providing ample space for both grand living and cozy retreats. The main home welcomes you with a charming sunroom of wood and exposed brick, leading into a formal dining room & library space centered around one of the home's three gas fireplaces. Culinary enthusiasts will appreciate the open-concept kitchen's central island and rich wood cabinetry, which flows effortlessly into a great room anchored by a striking brick fireplace that walks out to your spacious back deck. Retreat to the primary suite to find 2 double closets and a spa-like 5-piece ensuite bathed in light from a large skylight. A 2nd stairwell to this level brings you to 3 more bedrooms and a shared 3 piece bathroom while yet another bedroom or additional living space can be found in the unique top-level loft. The 3 Level Apartment on the South side of the home features its own entrance through a stunning vestibule, a main floor eat-in kitchen that walks out to the back deck, lower level family room with walk-out to the yard, a 3rd story primary suite with gorgeous 3 piece ensuite & laundry hookups, and the convenience of its own furnace, and hot water tank. The perfect space for rental income or extended family. Set on a deep 63 x 188 ft lot, the private backyard serves as a secluded oasis with mature hedges, low-maintenance gardens, and a spacious, multi-level deck for entertaining. Located just moments from the award-winning restaurants & shops of Broadway, the Island Lake Conservation Area, and within walking distance to local schools, this home offers a peaceful lifestyle with every urban convenience at your doorstep.More details
Data was last updated April 21, 2026 at 11:15 PM (UTC)
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