Stouffville Homes with 100+ Approx Age

Stouffville Homes with 100+ Approx Age

Welcome to Stouffville, a charming gem nestled in the heart of Whitchurch-Stouffville, Ontario. This vibrant community perfectly blends small-town charm with modern conveniences, making it an ideal place for families, retirees, and everyone in between. With its rich history dating back to the 1800s, Stouffville boasts a variety of homes that reflect its heritage, including many properties that are over 100 years old. These historic residences offer a unique character and timeless appeal, featuring intricate architectural details, spacious layouts, and mature landscaping.

Stouffville is known for its friendly atmosphere and strong sense of community. Residents enjoy a plethora of parks, walking trails, and recreational facilities, providing ample opportunities for outdoor activities and family fun. The downtown area is a delightful mix of quaint shops, cozy cafés, and local restaurants, where you can savor delicious cuisine and support local businesses.

Education is a priority here, with several highly-rated schools serving the community, making it a popular choice for families. The neighborhood is also well-connected, with easy access to major highways and public transit, allowing for convenient commutes to Toronto and beyond.

Whether you're captivated by the allure of historic homes or the welcoming vibe of this tight-knit community, Stouffville offers a truly enchanting place to call home. Explore the unique properties and discover the charm that awaits you in this picturesque neighborhood. Come and experience the warmth and beauty of Stouffville—your dream home is just around the corner!

Newest Stouffville Homes with 100+ Approx Age

$995,000
5 Beds ⋅ 3 Baths ⋅ N13525434 MLS
Attention Investors & Builders - Rare Value-Add Opportunity! Own a cash-flowing three-unit investment property with solid tenants in place and approved potential to expand into a six-unit residential building. Generate rental income from day one while creating substantial long-term value through future development-all at an attractive entry price. Brand-new roof installed in July 2026. Located on a newly rezoned RN5 lot, the property comes with Town-approved site plans and architectural drawings prepared as part of the rezoning process to support the approved six-unit concept. Years of planning, rezoning, and approvals have already been completed, allowing the next owner to move directly toward the building permit stage while retaining the flexibility to refine the design if desired. Multiple investment strategies are available: build the approved expansion and create a high-performing six-unit investment property, continue generating rental income while developing in phases, or modernize the existing units to further increase rental revenue and overall property value. Additional opportunity: the adjacent property may also become available for purchase, creating the potential to assemble nearly 0.5 acre in the heart of Stouffville-a rare opportunity for larger future development.Ideal for investors seeking both immediate cash flow and long-term upside. Guidance with project financing and commercial mortgage options may be available to qualified buyers.Strong rental demand, approved development potential, immediate income, and significant long-term value-all in one property.

6745 Main Street, Whitchurch-Stouffville
$979,000
2 Beds ⋅ 2 Baths ⋅ N13485756 MLS
Welcome to 213 Second Street - a rare blend of heritage charm, modern comfort, and backyard magic in the heart of Old Town Stouffville. Built in 1883, this beautifully maintained Gothic-Revival detached home is full of character, warmth, and the kind of curb appeal that makes you slow down when you walk by. Set on a spacious corner lot among some of Stouffville's most charming historic homes, this 2-bedroom, 2-bathroom property offers a thoughtfully designed living space. Inside, you'll find bright, cozy, and functional rooms that balance charm with everyday comfort. It's the kind of home that feels special the moment you step inside - updated without losing its soul. And then there's the backyard. Honestly, this is where things get really good. Designed for relaxing, entertaining, and making the most of summer, the outdoor space features a heated saltwater pool, lush landscaping, and a 200 sq. ft. cabana - perfect as a guest space, creative studio, home office, or private retreat. Morning coffee, pool days, evening cocktails, quiet nights under the stars... this backyard understood the assignment. The location is just as impressive. Tucked into beloved Old Town Stouffville, you're steps to local shops, cafés, parks, trails, and the GO Station, with downtown Toronto approximately 45 minutes away by car. Perfect for down-sizers, professionals, or anyone looking for a home with character, convenience, and a serious lifestyle upgrade, 213 Second Street is not just a place to live - it's a place to love.

213 Second Street, Whitchurch-Stouffville
$1,499,900
4 Beds ⋅ 3 Baths ⋅ N13161418 MLS
Welcome to 227 Second Street an architecturally striking custom luxury home in the heart of downtown Stouffville. Designed for elevated everyday living and exceptional entertaining, this one-of-a-kind residence blends dramatic design with warm, sophisticated finishes.Inside, soaring 25-foot open-to-above ceilings and floor-to-ceiling windows flood the home with natural light, while heated travertine marble floors, rich hardwood, exposed wood beams, and curated designer details create a refined yet inviting atmosphere.The chef-inspired kitchen features quartz countertops, premium Wolf and Sub-Zero appliances, custom cabinetry, and an expansive open-concept layout ideal for entertaining and family living alike.Step outside to your private resort-style backyard complete with a sparkling in-ground pool, multiple lounge areas, and beautifully designed outdoor living spaces perfect for summer gatherings.Upstairs, spacious bedrooms provide comfort and privacy, while the luxurious primary retreat offers a dedicated home office space and spa-inspired ensuite.Located just steps to Main Street Stouffville, restaurants, parks, schools, and the GO Train, this exceptional executive home delivers the perfect blend of luxury, community, and commuter convenience.

227 Second Street, Whitchurch-Stouffville
$973,000
3 Beds ⋅ 3 Baths ⋅ N13154386 MLS
5% Cap rate makes for a very attractive real estate investment located on Main St in central Stouffville. GO train is a 5 minute walk. This well maintained established legal triplex (R3) with three individual units; 1 x bachelor + 1 x 1-bedroom + 1 x 2-bedroom. Each of long term tenants (2017, 2019, 2022) wish to remain. This triplex has been well maintained with many updates including a complete make over of apartment #2, plus a updated bathroom and kitchenette in the bachelor unit. Roof 2019. Paved driveway 2021. The large front covered porch defines welcoming curb appeal into the secure front door to each apartment. The decking was new 2021. The paved driveway provides 2 parking spots for each tenant = 6 total parking spots. The driveway is off Albert Street. The side porch doubles as a gathering space and the common laundry room with commercial grade coin washer and dryer - approx $2k/yr. The side and back yards are a grass canvas enjoyed by the residents. The Upper unit includes a private balcony facing east to delight in each morning sunrise, plus a sunroom facing north. The basement with a separate entrance is ideal for storage, includes the gas furnace and the three owned hot water tanks. Optimal for investors looking for positive cash flow; Cap rate 5%. NOI 3.4%. Stouffville is growing, and offers a choice of schools, worship, shopping, sports fields, restaurants, banking and close to the Markham Stouffville hospital. #404 access from Stouffville Rd. Straight drive on 9th Line to #407. Floor plan attached. Financials attached.

6153 Main Street, Whitchurch-Stouffville
$1,279,000
N12820784 MLS
Prime Main Street Corner Opportunity - Live, Work, or Invest. Positioned on a highly visible corner lot on Main Street, 6038 Main St., Stouffville offers exceptional exposure and flexibility. Zoned for mixed commercial use, the property is ideally suited for a principal residence, professional office, clinic, studio, or personal service business. Currently operating as a osteopathic clinic.This distinguished 2-storey brick building, originally built in 1913, features outstanding curb appeal with a sweeping wraparound Victorian-style porch. The interior has been thoughtfully restored, showcasing original hardwood floors and wood trim and electrical panel with 200-amp service.The layout includes five bedrooms and three bathrooms, providing ample space for residential living, business use, or a combination of both. Additional highlights include parking for four vehicles plus a garage, a fenced backyard, and strong street presence that supports a wide range of permitted uses. A rare opportunity to own a commercially zoned residential property on Main Street in one of Stouffville's most desirable locations-ideal for owner-users, professionals, or investors seeking long-term value in any market.

6038 Main Street, Whitchurch-Stouffville
$1,279,000
5 Beds ⋅ 3 Baths ⋅ N12777908 MLS
Prime Main Street Corner Opportunity - Live, Work, or Invest. Positioned on a highly visible corner lot on Main Street, 6038 Main St., Stouffville offers exceptional exposure and flexibility. Zoned for mixed commercial use, the property is ideally suited for a principal residence, professional office, clinic, studio, or personal service business. Currently operating as a osteopathic clinic.This distinguished 2-storey brick building, originally built in 1913, features outstanding curb appeal with a sweeping wraparound Victorian-style porch. The interior has been thoughtfully restored, showcasing original hardwood floors and wood trim and electrical panel with 200-amp service.The layout includes five bedrooms and three bathrooms, providing ample space for residential living, business use, or a combination of both. Additional highlights include parking for four vehicles plus a garage, a fenced backyard, and strong street presence that supports a wide range of permitted uses. A rare opportunity to own a commercially zoned residential property on Main Street in one of Stouffville's most desirable locations-ideal for owner-users, professionals, or investors seeking long-term value in any market.

6038 Main Street, Whitchurch-Stouffville
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