York Homes with 100+ Approx Age

York Homes with 100+ Approx Age

Welcome to York, Ontario—a charming community steeped in history and brimming with character. Nestled in the heart of Canada, York offers a unique blend of urban convenience and rural tranquility, making it an ideal place for families, young professionals, and retirees alike.

York is known for its picturesque landscapes, featuring lush parks, serene waterways, and vibrant gardens that showcase the beauty of the changing seasons. The area's rich history is reflected in its architecture, with many homes boasting an impressive age of 100 years or more. These vintage properties are not just houses; they are stories waiting to be told, each with its own unique charm and character. Imagine living in a home that has stood the test of time, where original hardwood floors, ornate moldings, and antique fixtures whisper tales of the past.

Community spirit thrives in York, with friendly neighbors and local businesses that cater to a variety of tastes and preferences. Enjoy leisurely strolls through historic streets, visit quaint cafes, and explore boutique shops that offer a taste of local craftsmanship. The area is also well-connected to major highways, ensuring easy access to the bustling city life of Toronto while providing a peaceful retreat to come home to.

For those seeking a home with history, charm, and a strong sense of community, York is a hidden gem that promises not just a place to live, but a place to belong. Discover your dream home in this enchanting region today!

Newest York Homes with 100+ Approx Age

$1,149,000
5 Beds ⋅ 3 Baths ⋅ N13821518 MLS
Locations like this rarely become available. Commercially zoned and standing on one of Stouffville's busiest and most recognizable intersections, 6038 Main St offers the kind of daily exposure that no amount of advertising can replicate. This is a location that works for you every single day, whether you're running a professional practice, a personal service business, or a studio built around foot traffic and visibility.The building itself sets you apart from anything else on the market. A 2 storey brick Victorian dating to 1913, it brings genuine character to a commercial footprint, hardwood floors, original trim, and a wraparound porch that gives clients a grand sense of arrival that most businesses simply cannot offer. Five bedrooms and three bathrooms across approximately 2,294 sq ft above grade provide real flexibility for office layout, treatment, or consultation space, or the opportunity for a live-work arrangement. Two fireplaces plus a 200 amp electrical panel mean the property performs as well as it presents. Five minutes on foot to the GO train puts staff, clients, and owners within easy reach - a genuine advantage for any business drawing from the broader GTA. A detached garage and parking for five vehicles round out a setting that's this functional and this full of character on a single Main Street lot. This offering is for the real property only - the current business is not included in the sale - and possession can be arranged quickly for a buyer ready to move. Zoning, layout, and use flexibility make this a property worth a conversation.

6038 Main Street, Whitchurch-Stouffville
$1,149,000
5 Beds ⋅ 3 Baths ⋅ N13820884 MLS
A rare opportunity to own a piece of Stouffville's Main Street history. Proudly positioned on one of the town's most recognizable corners, this distinguished two-storey brick Victorian has stood here since 1913 and continues to make an impression. A sweeping wraparound porch welcomes you into a home filled with original character, including hardwood floors, rich wood trim, and two fireplaces. Offering approximately 2,294 sq. ft. above grade, the spacious layout features 5 bedrooms and 3 bathrooms, with a sense of scale uncommon for a home of this era. A 200-amp electrical panel adds an important modern upgrade. Flexible zoning - dual residential and commercial - provides a range of possibilities beyond a single-family residence, including a professional office, studio, personal service business, or beautifully restored home. Ideally located just a 5-minute walk to the GO Train and close to the heart of Stouffville, the property combines convenience with everyday Main Street exposure. Detached garage and parking for 5 vehicles complete this exceptional setting. Character, versatility, visibility, and location come together in a property that is truly difficult to replicate.

6038 Main Street, Whitchurch-Stouffville
$735,000
2 Beds ⋅ 1 Baths ⋅ N13820234 MLS
Situated in the heart of prestigious Aurora Village, this exceptional 60 x 181.5 ft lot presents a rare opportunity to secure a prime piece of real estate in one of Aurora's most desirable and high-exposure locations. Surrounded by a vibrant mix of residential homes, established businesses, restaurants, parks, and schools, and just minutes to the GO Train, this property offers unmatched convenience and connectivity. The property could permit a wide range of potential uses including office, service commercial, fitness, and other employment-oriented applications , making it an ideal candidate for investors, end-users, or developers looking to capitalize on Aurora's continued growth and strong demand. This standout lot delivers the flexibility and location to bring your vision to life. Opportunities like this in Aurora Village are few and far between - a premium lot, versatile permitted uses, and an unbeatable location all in one.

148 Centre Street, Aurora
$875,000
3 Beds ⋅ 2 Baths ⋅ N13804358 MLS
Welcome to 6055 Main Street, a distinctive 1.5 storey property located in the West Main Street/Stouffville Junction Heritage Conservation District. Set on a private corner lot in the heart of Stouffville, this charming arts and crafts style property combines character, functionality, and versatility in a location that is exceptionally convenient. Recognized as a triplex in the MPAC structural description, the property offers multiple independent living spaces, making it well suited to multigenerational living, extended family, or those looking to explore rental opportunities. The main floor and second floor units are move in ready, while separate entrances provide privacy and convenient access between the different levels. The rear entrance leads directly to the basement, which also offers potential to create additional living space through renovation. Architectural character is evident throughout, including distinctive Art Deco inspired trim surrounding the windows and a welcoming covered front porch that adds to the home's timeless appeal. The porch offers a lovely place to enjoy a morning coffee or unwind while taking in the established neighbourhood. Situated on a corner lot, the property enjoys a generous private driveway bordered by a mature tree line, creating a beautiful natural separation from the road. The spacious driveway provides plenty of parking, while the mature trees add privacy, greenery, and a peaceful feel to the property. Location is a standout feature. Enjoy the convenience of being within walking distance of grocery stores, the GO Train station, shops, restaurants, parks, and everyday amenities. Laundry facilities are conveniently located in the basement, adding practical everyday convenience. 6055 Main Street is a unique opportunity to own a character filled property with versatile living arrangements, privacy, and an outstanding central Stouffville location.

6055 Main Street, Whitchurch-Stouffville
$959,900
4 Beds ⋅ 2 Baths ⋅ N13780968 MLS
A rare opportunity on a 51.25 130 ft lot in the heart of Richmond Hill, just steps from Yonge Street and the Mill Pond community. This 4-bedroom detached home combines a highly desirable location, substantial lot and Mixed Use designation offering potential for professional or business use. Inside, the centre-hall layout features hardwood flooring and wide-plank floors in select rooms, with a bright living room and separate formal dining room. The renovated kitchen includes granite countertops and stainless steel appliances, complemented by two updated bathrooms. The spacious principal bedroom features a walk-in closet with custom organizers. A flexible main-floor laundry and exercise room offers heated flooring, built-in cabinetry and a walkout to the large backyard, with plenty of room to relax, garden or entertain. The property also includes a patio, storage shed and parking for two vehicles. Walk to transit, shops, restaurants, parks and Richmond Hill's historic village core. A designated heritage property offering character, comfortable living space and exceptional flexibility in a central Richmond Hill location.

37 Arnold Crescent, Richmond Hill
$1,880,000
7 Beds ⋅ 5 Baths ⋅ N13777242 MLS
MUST BE SEEN! Wonderfully decorated and updated throughout, just the right touch of modern and charming. Great opportunity for extended family or investment, live in one half and rent the other half. TWO...main floor Kitchens, living rooms, dining rooms, 2 Main floor laundry rooms, and seven bedrooms upstairs! Majestic over one-acre manicured lot with large Eating and Entertaining area/Patio and gardens, lot backs onto protected land No homes behind! Walk to quaint shops, restaurants/patios on Historic Main Street. The home is currently being used as a single-family dwelling; however, it can easily be used as two separate homes with two front and back entrances. Many Possibilities.

390 Main Street, King
$2,999,900
3 Beds ⋅ 3 Baths ⋅ N13757734 MLS
There are homes, and then there is 41 Kennedy Street West. Set on 2.3 private acres just minutes from Yonge Street, this exceptional home offers a rare combination: total privacy and complete convenience. Tannery Creek runs quietly through the grounds, crossed by two footbridges near a small waterfall, with the Aurora GO station, schools and shops all close at hand. The interior space is the real surprise. Monaco Interiors led the restoration, preserving the stucco and fieldstone exterior while completely rebuilding the inside for the way people actually live today. The kitchen is the clearest example: marble counters, a GE Monogram range, Sub-Zero fridge, Miele dishwasher, a built-in coffee bar, and an eat-in area that opens straight into the family room - shiplap ceiling, marble-surround fireplace, custom bar, and a walkout to the patio and gardens beyond. A sunroom, a coffered-ceiling dining room, and a great room with window seats round out the main floor, each holding onto a view of the property. Upstairs, the primary suite is built for retreat - gas fireplace, skylight, a private balcony, walk-in closets, and a 5-piece ensuite with heated floors and a freestanding soaker tub. Downstairs, a fully waterproofed lower level offers a recreation room, laundry, a craft space, and room still to finish to taste. Properties like this rarely change hands. 41 Kennedy Street West offers privacy, space, and a home built for modern life - all within reach of everything Aurora has to offer.

41 Kennedy Street W, Aurora
$1,299,900
5 Beds ⋅ 4 Baths ⋅ N13768580 MLS
Incredible value for this Beautiful property! Nestled on a quiet, tree-lined street in the heart of sought-after Mill Pond, this Beautiful Century Home masterfully blends Charm & Character with $$ THOUSANDS spent in meticulous modern upgrades. THE MAIN RESIDENCE OFFERS ALMOST 2200 SF, featuring 4 bedrooms & 3 bathrooms. The primary bedroom SANCTUARY is complete with a SPA-LIKE ensuite bathroom offering a cast iron tub, brand new shower, Juliet balcony, and an oversized walk-in closet. The fabulous main floor layout offers a formal living room, spacious family room, updated kitchen w/granite counter, plus a cozy library w/fireplace & brand new main floor 3 pc bathroom. Recent upgrades include; Updated kitchen in 2020, new appliances, Fridge 2024, Stove 2023, Washer/Dryer 2025, New pot lights in Family rm '25, New sump pump' 25, New gas boiler/6 rads in 2013, many new windows throughout, with original heritage glass at the front. Step outside to a fully fenced backyard with perennial gardens and an incredible DETACHED GARDEN STUDIO, previously used as a garage and now perfect for home office, artist studio, man cave. she shed, workshop, teen flat or nanny flat-completely self contained and Upgraded in 2021. This gorgeous home offers with a rare 10-car driveway, ample basement storage, and 200-amp service! Enjoy morning coffees & relaxing evenings on your sprawling front porch-reconstructed in 2024. The tranquility of a quiet side street while being mere minutes from the vibrant Mill Pond community events and walking paths, plus minutes to Yonge Street, offering restaurants, shops & cafes! A truly unique property offering unmatched value and lifestyle options. Please note, this is not a designated heritage house.

64 Powell Street, Richmond Hill
$1,689,000
4 Beds ⋅ 3 Baths ⋅ N13766652 MLS
Step into timeless elegance with this beautifully preserved century home where the character and craftmanship of 1916 blend seamlessly with the comforts of modern living. From the moment you arrive, the inviting veranda sets the tone - a perfect spot to unwind with a morning coffee or greet guests in style. Inside, you'll find expansive principal rooms with natural light, rich architectural details, and a warm welcoming atmoshpere ideal for both everyday living and entertaining. High ceilings and generous proportions create a sense of openness while maintaining the cozy charm that only a historic home can offer. The very functional kitchen was updated in 2026 with new cabinetry and ample storage. High-end appliances including SubZero fridge and wine fridge, WOLF induction range, Miele dishwasher, Wolf BBQ and LG washer/dryer. Set on a spacious 50x200' lot, the outdoor amenities are just as impressive. A large deck provides the perfect backdrop for summer gatherings, while the sport court offers endless recreation opportunites including basketball, pickleball, tennis, and ice rink. Evenings can be spent gathered around the fire pit under the stars. This is more than a home - it's a lifestyle where heritage charm meets outdoor living at its finest. Fabulous family location. Walking distance to the library, Town Park home of the Aurora Farmers Market, movie and music in the park evenings, shops and restaurants. 1.2km to Aurora GO Train. Conveniently located close to St. Andrew's College, St. Anne's School, Country Day School, and Villanova.

58 Tyler Street, Aurora
$2,249,000
4 Beds ⋅ 4 Baths ⋅ N13758492 MLS
Welcome to the distinguished John S. Millard House-an exceptional heritage residence where historic character has been thoughtfully preserved & seamlessly blended w/ modern comfort & sophistication. Sought after location just steps to Newmarket's award winning downtown w/ shops, restaurants, bars, farmers market, Riverwalk Commons & trail system. Fully renovated, the home showcases soaring ceilings, extensive trim, wainscoting, crown moulding & hand-scraped hardwood flooring. The gourmet kitchen features stone counters, retro appliances, tall cabinetry w/glass inserts, custom backsplash, lighting & flooring, flowing into a sunken "Muskoka" room rich in wood detailing & warmed by a gas fireplace, overlooking the expansive cottage-like backyard oasis w/ coveted western exposure. Formal living & dining rooms offer a step back in time w/ soaring ceilings, traditional baseboards & refined trim. The impressive primary suite features a generous walk-in closet leading to a fully updated ensuite w/ modern glass shower, inviting soaker tub & 9' ceilings. The walk-out lower level provides a private in-law suite, ideal for extended family or guests. Outside, the exceptionally rare, deep lot creates a private summer oasis complete w/ sparkling in-ground pool & private gazebo-perfect for entertaining & family gatherings. Beyond the pool, the original barn has been transformed into an extraordinary private retreat, featuring a games room, additional bedroom & ensuite on the lower level and a spectacular upper-level recreation room w/ live-edge bar, extensive wood & beam detailing and multiple lookouts overlooking the pool. The barn also offers exciting potential to become an exquisite carriage house. A rear bunky/shed adds to the property's authentic north-country charm. An incredibly rare offering that combines heritage, elegance, thoughtful renovation & exceptional recreational spaces-truly a piece of Newmarket history-reimagined for modern living!

150 Lorne Avenue, Newmarket
$3,888,000
6 Beds ⋅ 2 Baths ⋅ N13757856 MLS
Very unique high class freestading office building, right at downtown of Aurora, one of most oldest heritage structure in Aurora, Situated just west of Yonge Street, north of Wellington St, the property is surrounded by a dense network of established medical, legal, and financial offices. Approximately 3,000 square feet of highly functional, converted office space, Updated with a comprehensive interior renovation in 2016, featuring more than 10 partitioned offices optimized for professional practices. 1 washroom on the 1st floor, 1 washroom on the 2nd floor, 1 dedicated lunch room, and 1 fully equipped kitchen, A massive asset for downtown Aurora, providing 11 dedicated parking spaces equipped with 3 Tesla electric vehicle charger, building was build at 1875, well maintained heritage building.

15342 Yonge Street, Aurora
$1,399,999
4 Beds ⋅ 3 Baths ⋅ N13756530 MLS
Client RemarksEscape the ordinary and embrace extraordinary where small city feels meet big city access at 227 Second Street, in the heart of Stouffville! This breathtaking custom-built masterpiece is where luxury, design, and lifestyle come together seamlessly. From the moment you step inside, you're greeted by dramatic 25-foot soaring ceilings and an abundance of natural light pouring through spectacular floor-to-ceiling windows. The grand open-concept living space is perfect for entertaining or cozy family nights by the fireplace. Warmth and modern excellence create a truly unique space. Exquisite heated travertine marble flooring flows through the principal areas, complemented by rich hardwood flooring, sleek pot lights and gorgeous wood beams that enhance every architectural detail. Every inch of this home has been thoughtfully curated with upscale finishes and superior craftsmanship.The chef-inspired custom kitchen is a showstopper - featuring quartz countertops, premium Wolf and Sub-Zero stainless steel appliances, custom cabinetry, and an expansive layout perfect for both entertaining and everyday living. Step outside to your private backyard oasis - an entertainer's dream complete with a sparkling in-ground pool, beautifully designed lounging areas, and the perfect setting for summer gatherings or peaceful evenings under the stars. Upstairs you find generous sized bedrooms and a Primary Retreat complete with office and a spa like ensuite. With parking for five vehicles and a prime location just steps to charming downtown Stouffville amenities, parks, schools, and go train, this exceptional residence offers refined living without compromise. 227 Second Street is more than a home - it's a statement.

227 Second Street, Whitchurch-Stouffville
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