Simcoe Homes with 100+ Approx Age

Simcoe Homes with 100+ Approx Age

Welcome to Simcoe County, Ontario – a captivating region that beautifully blends natural beauty with rich history. Nestled in the heart of Central Ontario, Simcoe County is renowned for its stunning landscapes, vibrant communities, and an abundance of recreational opportunities. From the sparkling shores of Lake Simcoe to the lush forests and rolling hills, this area is a haven for nature lovers and outdoor enthusiasts alike.

In Simcoe, you'll find a diverse range of homes, many of which boast an impressive age of 100 years or more. These charming properties are steeped in history, offering a unique glimpse into the architectural styles and craftsmanship of bygone eras. Whether you’re drawn to the classic Victorian designs or the rustic charm of century-old farmhouses, there’s something truly special about owning a piece of Simcoe’s storied past.

The region is also home to a welcoming community that values its heritage while embracing modern living. With a plethora of local amenities, including boutique shops, delightful eateries, and cultural attractions, residents enjoy a balanced lifestyle that harmoniously blends the old with the new.

Additionally, Simcoe County is perfectly positioned for those who crave outdoor adventures. From hiking and biking trails to winter sports and water activities, the region offers year-round fun for families and individuals alike.

Come explore the enchanting homes of Simcoe County, where every property tells a story and the charm of the past meets the vibrancy of today. Your dream home awaits in this picturesque corner of Ontario!

Newest Simcoe Homes with 100+ Approx Age

52 Parkside Drive, Barrie
$499,000
3 Beds ⋅ 2 Baths ⋅ S14028636 MLS
**Century Charm, Prime Queens Park Location & Exciting Investment Potential** Set in Barrie's sought-after Queens Park neighbourhood, this character-filled century home combines timeless details with thoughtful updates and an impressive range of possibilities. Offering plenty of space to spread out, the home sits on a generous 54' x 132' lot directly across from a large park with tennis courts. Quiet area, well-manicured exterior, and an interior ready for quality living! Inside, original character shines through with 9' ceilings, beautiful trim, a classic parlour, and a dedicated dining room. The bright eat-in kitchen features a separate pantry and peninsula, while the spacious great room adds a vaulted ceiling, gas fireplace, and 3-piece bathroom. Step outside from the great room onto the large deck overlooking the fully fenced backyard, complete with mature gardens, a shed/playhouse, and plenty of room to relax or entertain. Upstairs, you'll find three bedrooms, additional storage, and a charming 4-piece bathroom with a clawfoot tub. The finished basement adds valuable flexibility with a bonus room that could serve as a fourth bedroom, along with laundry and additional storage. The exterior offers excellent functionality with a double driveway accommodating up to five vehicles, patterned concrete, a detached single garage, dedicated garbage storage, stone pathways, and established perennial gardens throughout the property. Recent improvements include a new roof (2024), new vinyl flooring (2024), new staircase (2024), on-demand hot water system, and central air conditioning. Adding even more potential, the property is zoned RM2, allowing for multi-unit residential possibilities, subject to applicable approvals and municipal requirements. With similar development taking place nearby, this is an opportunity worth exploring for homeowners, builders, and investors alike.

52 Parkside Drive, Barrie
16 Blake Street, Barrie
$1,500,000
7 Beds ⋅ 3 Baths ⋅ S14027808 MLS
Own a remarkable piece of Barrie's history at 16 Blake Street. Known historically as "Foxley," this distinguished 1916 residence forms part of the city's architectural heritage, offering timeless character and exceptional space in a beautiful setting. With 7 bedrooms, 3 bathrooms and 4,446 sq. ft. above grade, the home provides room to gather, entertain and create spaces that suit your lifestyle. Set on an expansive 188 ft. x 270 ft. lot, the grounds are a defining feature: remarkably private and surrounded by mature trees, they create the feeling of a secluded retreat in the middle of a forest. Enjoy peaceful mornings, outdoor gatherings and the beauty of the changing seasons, all within easy reach of downtown Barrie, Kempenfelt Bay, waterfront trails, parks, restaurants and cultural attractions. A rare opportunity to become the next steward of a storied home where historic character, generous proportions and extraordinary privacy come together.

16 Blake Street, Barrie
102 Clapperton Street, Barrie
$899,000
3 Beds ⋅ 2 Baths ⋅ S13886590 MLS
Discover the timeless elegance of this captivating Queen Anne-style residence, where historic charm and architectural beauty are showcased throughout. From the impressive wrap-around porch and expansive sash windows to the original stained-glass features, ornate ceiling mouldings and tall baseboards, this home is rich in character and craftsmanship. Set on a beautifully landscaped 0.3-acre lot, the home is ideally located moments from Downtown Barrie, its many amenities and picturesque waterfront. Adetached double-car garage with storage, plus two driveways offering parking for up to seven vehicles, provides exceptional convenience, with one driveway finished in attractive interlock stone. Step through the solid wood entrance door with a stained-glass insert into interiors featuring original wood floors, soaring ceilings and generous windows. French pocket doors connect the living room to the inviting family room, complete with a wood-burning fireplace and original wood surround. The spacious main floor offers a wonderful flow between principal rooms. The kitchen features ample cabinetry and counter space, an island, stainless-steel appliances and terracotta floor tiles. Adjacent, the breakfast area/conservatory provides a delightful space to enjoy garden views. The formal dining room boasts a beautiful custom-built display cabinet and charming servants stairs leading to the upper landing. Main-floor laundry and a 3-piece bathroom offer practicality, with convenient adjacent access to the rear deck. Upstairs are three generously sized bedrooms, including an impressive primary suite with an expansive walkin closet/dressing room and access to a private balcony. The 4-piece family bathroom features a classic clawfoot bathtub. A staircase leads to the attic, offering additional space and future potential. A rare opportunity to own a piece of Barries history, combining the elegance of a bygone era with generous living spaces, privacy and an exceptional downtown location.

102 Clapperton Street, Barrie
469 Robert Street, Midland
$199,900
3 Beds ⋅ 1 Baths ⋅ S13883766 MLS
Excellent opportunity for investors or buyers looking for a potential redevelopment project! Situated on a corner lot in a convenient Midland location, this property offers the opportunity to explore demolition and new construction, subject to applicable municipal approvals and requirements. Conveniently located close to schools, the Bourgeois Community Centre, Little Lake Park, marinas, restaurants, and downtown Midland.

469 Robert Street, Midland
408 Regent Street, Orillia
$469,000
3 Beds ⋅ 2 Baths ⋅ S13881028 MLS
WARM & INVITING INTERIOR WITH OVER 1,500 SQ. FT., A FENCED BACKYARD & CENTRAL ORILLIA LOCATION! 408 Regent Street offers distinct living spaces and a flexible main floor, with natural light filling the living and dining areas and a kitchen featuring rich wood cabinetry, a tiled backsplash and stainless steel fridge. A separate main-floor family room opens directly to the private, fully fenced 44 x 115 ft lot, where a landscaped yard and garden shed leave room for kids, pets, gardening and long summer afternoons outside. With a 4-piece bathroom and laundry on the same level, the family room could also serve as a main-floor primary bedroom, home office or playroom if desired. Three bright bedrooms share a second 4-piece bathroom, while the unfinished basement provides valuable storage. Metal roofing covers most of the home, complemented by a multi-vehicle driveway, 200-amp electrical service, forced-air heating and an owned water heater. Kids can walk home from local schools, afternoons can mean nearby parks and trails, and sunny weekends can be spent at Tudhope Park, Couchiching Beach or along the waterfront. The Brian Orser Arena, public transit, local shopping, downtown Orillia and Hwy 11 are also close by, keeping daily essentials, recreation and some of Orillia's best destinations close to home.

408 Regent Street, Orillia
226 Queen Street, Midland
$539,900
6 Beds ⋅ 3 Baths ⋅ S13880940 MLS
LEGAL TRIPLEX | INVESTMENT | MIDLAND - Legal triplex in Midland with three self-contained units. Two front units are heated by gas furnace that was updated in Dec 2021 and the back unit has a gas fireplace and electric baseboard heat. With a new roof in 2022, on demand hot water and water softener this is an ideal property to add to your investment portfolio - or - start your new real estate portfolio with this triplex! Don't miss out on this opportunity! The waterfront community of Midland offers outstanding all season recreation, key amenities (shopping, services, fine and casual dining, recreation and entertainment) and easy access to commuter routes. Financial information available upon request. Rents as stated are inclusive. Convenience of appliances, full bath, laundry and parking for each unit.

226 Queen Street, Midland
10 Eplett Street, Severn
$649,900
4 Beds ⋅ 2 Baths ⋅ S13880548 MLS
Top 5 Reasons You Will Love This Home: 1) Offering over 2,100 square feet above grade, this spacious century home provides an abundance of room for family living with four bedrooms, including one featuring its own unique loft space and additional storage 2) Rich in character and history, the home showcases original hardwood flooring, wood doors and trim, soaring ceilings, and timeless architectural details, complemented by a spacious kitchen with warm pine cabinetry and a wood-burning stove 3) Designed with plenty of room to gather, the bright living and dining areas are joined by a separate family room featuring a wet bar and built-in seating, creating an inviting space for entertaining and spending time with family and friends 4) Extend your living space outdoors with a large three-season room opening onto the back deck, while the covered front porch adds classic century-home charm and provides a welcoming spot to relax and enjoy the surroundings 5) Move in with added confidence knowing important improvements, including electrical and roofing, have been completed within the past five years, while the generous lot features a spacious backyard, mature trees, and multiple outbuildings offering valuable storage and versatile space. 2,187 sq.ft. plus an unfinished basement.

10 Eplett Street, Severn
48 Brock Street, Barrie
$749,000
3 Beds ⋅ 2 Baths ⋅ S13880368 MLS
CENTURY-OLD HOME FILLED WITH ORIGINAL CHARACTER, BEAUTIFULLY PRESERVED ARCHITECTURAL DETAILS & EXTENSIVE MODERN UPGRADES! Offering 2,155 finished sq. ft., this double-brick home showcases original wood trim with decorative rosette detailing, 13-inch baseboards, stained-glass accents and hardwood flooring that reflect its original craftsmanship. The main floor features a renovated kitchen with white cabinetry, quartz countertops, a built-in dishwasher and microwave, open shelving and a tongue-and-groove farmhouse-style backsplash. The adjacent living and dining area offers space to gather, while the family room occupies a rear addition featuring tongue-and-groove pine walls and a newer canopy-style window. Upstairs, three bedrooms and a second renovated kitchen provide additional living space, with both levels offering their own 4-piece bathroom and laundry area. The partially finished basement includes a rec room with built-in pine and brick cupboards. Outdoors, mature greenery and landscaped gardens add to the property's charm, while a large covered front porch, rear deck, cedar-trimmed garden shed, barbecue enclosure with gas hookup and detached garage complete the exterior. Significant updates include the roof (2026), furnace and air conditioning (2025), electrical upgrades to both units with 200-amp service to the house and 60-amp service to the garage, plus a sealed and patched driveway. Zoned RM2 in a central neighbourhood between two Highway 400 access points, the property is also within walking distance of Barrie's waterfront and Allandale Waterfront GO Station. Whether used as one large family residence, for multi-generational living or to generate potential rental income, this home's legal duplex configuration offers flexibility for its next owner.

48 Brock Street, Barrie
43 Brock Street, Barrie
$660,000
3 Beds ⋅ 2 Baths ⋅ S13879468 MLS
Warm and Charming Century Home in Barrie. All brick with lovely sunroom*grand foyer*Spacious Living room open to the Dining room with a full wall of built in cabinetry*Sunny kitchen has a walkout to a patio/garden*2 piece bathroom for guests*Three good size bedrooms*Recent updates include a new furnace, new underground water service *new window wells*newer windows, updates to the main-floor bathroom, roof about 6 years old*Nine foot ceilings, original 10" baseboards and hardwood floors throughout*Separate garage with extra workshop space and garage door opener*Best of all is the location - imagine strolling down to beautiful Kempenfelt Bay, enjoying Barrie's waterfront trails and parks, or walking to the GO Station when you need to commute. A welcoming home in a mature neighbourhood where history, convenience and lifestyle come together. 4 minute drive to 400, close to downtown restaurants and shops.

43 Brock Street, Barrie
4177 County Road 124 Road, Clearview
$1,295,000
5 Beds ⋅ 2 Baths ⋅ S13878680 MLS
Your Winter Retreat Awaits! Imagine weekends on the slopes, evenings gathered around the fireplace and relaxing soaks in the hot tub after a day outdoors. This extraordinary, renovated 1897 church in the charming village of Nottawa offers a truly unique escape in the heart of Southern Georgian Bay's four-season playground. An ideal home base for skiing, snowboarding and enjoying the area's many outdoor adventures, it is equally suited to year-round living for those drawn to its remarkable character and welcoming atmosphere. Best of all, it is being offered fully furnished, from the linens, rugs and artwork to the antiques, dishes and thoughtful finishing touches, making it easy to settle in and start enjoying the season. Inside, soaring post-and-beam cathedral ceilings create a spectacular chalet-inspired atmosphere, complemented by the soft glow of stained glass windows and a beautiful blend of historic details and modern improvements. Gather by the wood-burning fireplace in the main living area, enjoy a drink at the welcoming bar reclaimed from an old general store, or unwind in the adjoining lounge with its gas fireplace and full-size billiards table. The generous dining area seats 14, making après-ski dinners and entertaining family and friends a pleasure. Five beautifully appointed upstairs bedrooms offer plenty of room for overnight guests, while a main-floor den with a pull-out sofa bed and ensuite bathroom provides additional sleeping space. Outside, a spacious deck, oversized BBQ and enormous hot tub beneath a canopy of mature trees invite you to relax and recharge after a day on the mountain. Full of warmth, character and unexpected charm, this is a home made for memorable weekends, festive gatherings and everyday living. A rare opportunity to own a fully furnished, turnkey retreat in a sought-after four-season destination, ready to enjoy this winter.

4177 County Road 124 Road, Clearview
202-204-206 Hurontario Street, Collingwood
$1,850,000
S13878412 MLS
A rare opportunity to own a piece of downtown Collingwood's heritage, this exceptional red-brick century mixed-use building at 202-204-206 Hurontario Street offers a compelling investment in the heart of one of the region's most vibrant and sought-after communities. Ideally positioned on the west side of Hurontario Street between 3rd and 4th Streets, the approximately 4,728 sq. ft. building features a 2,778 sq. ft. ground-floor restaurant complemented by two spacious 975 sq. ft. residential apartments above. The long-term, successful restaurant tenant has made significant improvements to the property, including an extensive renovation in 2022 and the combination of both ground-floor units into one impressive restaurant space. Restaurant is licensed for 77 people with 20 more on the patio. The two spacious 1-bedroom apartments were renovated in 2015 and feature high ceilings, glass showers and stainless-steel appliances. One apartment has also been further upgraded with a new kitchen and stone countertops. Both units are currently occupied on a month-to-month basis, with tenants responsible for their own utilities. New hot water tanks were installed in both apartments in 2025. The property also offers three private, reserved parking spaces at the rear-an exceptional benefit in downtown Collingwood. Surrounded by the restaurants, shops, cafés, galleries and amenities of Hurontario Street, this is an outstanding opportunity to acquire a fully tenanted mixed-use asset with strong income potential and enduring downtown appeal.

202-204-206 Hurontario Street, Collingwood
173 Dunlop Street W, Barrie
$1,149,000
S13878040 MLS
RARE LIVE-WORK-INVEST OPPORTUNITY ON ONE OF BARRIE'S BUSIEST CORNERS, OFFERING PRIME EXPOSURE, A FLEXIBLE 3,895 SQ FT LAYOUT WITH BOTH OFFICE & RESIDENTIAL SPACE, & ENDLESS FUTURE POTENTIAL! Capitalize on this exceptional mixed-use opportunity in Barrie's sought-after west end, where your business can be seen, remembered, and thrive. Commanding a high-profile corner location at the intersection of bustling Dunlop Street West and Eccles Street, this property delivers the visibility, flexibility, and income potential that savvy investors and entrepreneurs are seeking. The attractive brick building offers approximately 3,895 sq ft of space, including bright and welcoming professional offices and a self-contained 2-bedroom apartment, opening the door to multiple revenue streams or providing the convenience of living and working in one location. Benefiting from ongoing improvements and strategic renovations throughout the years, the property has been well cared for and thoughtfully positioned for long-term success. Expansive street frontage, excellent corner exposure, and prominent signage opportunities ensure your business stands out in one of Barrie's most travelled corridors. Approximately eight on-site parking spaces add exceptional value, while the versatile layout easily accommodates a wide range of professional uses, including medical, legal, accounting, real estate, mortgage, consulting, and other office-based businesses. Set on a 0.13-acre lot with RM2 (SP-189) zoning and future redevelopment potential, subject to municipal approvals, this property is as much an investment in tomorrow as it is a business opportunity today. Just minutes from downtown, the waterfront, public transit, established residential neighbourhoods, and major arterial roads, this is a rare chance to secure a landmark address with built-in residential accommodation, strong income-generating possibilities, and endless potential for growth.

173 Dunlop Street W, Barrie
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