10 Incredibly Charming Homes on the Ontario Market

Experience the allure of old-world charm seamlessly blended with modern comforts in these ten incredibly charming homes on the Ontario market, each offering unique character and a welcoming atmosphere.

Listing agent: Deborah Cardiff

Stunning Victorian yellow brick home in desirable uptown Waterloo / Mary Allen neighborhood. This completely restored and updated century home combines the very best of old world charm with contemporary architectural design. The original Victoria home facade has been retained to keep and compliment the feel of the neighborhood.


Size: 3,003 sf


Price: $1,950,000


Listing details: The two story addition was added with a contemporary modern vision. Approximately 3700 finished sq feet of exquisite living space with high end finishes and top of the line appliances. Spacious bright open concept main floor features gracious foyer entrance, formal living room, state of the art kitchen with breakfast bar and adjoining dining room, formal living room, and fabulous main floor family room with gas fireplace & built-in wet bar.


Contact: Deborah Cardiff, Peak Realty Ltd., +1 519-747-0231


67 Mary Street, Thamesville, ON
Listing agent: Bridget Blonde

The incredible quality of construction and long-term maintenance are obvious the second you walk into this 1913-built beauty. On a massive double lot in the quiet town of Thamesville, Ontario, a place where your children can play outside and walk to school safely. The principal rooms include a living room, dining room, office and solarium – all with high ceilings and huge windows letting in endless light.


Size:   sf


Price: $574,000


Listing details: The bedrooms are also large with a primary en suite and a walk-in linen closet featuring a built-in cedar chest. The kitchen & bathrooms have had modern updates and the heating & cooling system was replaced in 2021. This home is more than a place to live – it’s a piece of history.


Contact: Bridget Blonde, Nest Realty Inc., +1 519.365.0568

6000 Trotter Rd | $649,900

6000 Trotter Rd, Perth Road, ON
Listing agent: Coleen Ure

Welcome to this cozy log home nestled on a serene and quiet country road! Step inside to discover a warm and inviting living space anchored by a cozy pellet stove, perfect for those chilly evenings. This home offers a very spacious primary bedroom with patio doors onto a side deck an ideal spot to savor your morning coffee.


Size: 2,172 sf


Price: $649,900


Listing details: With two bedrooms and a bathroom on each level, there’s ample space for family and guests. The fully finished lower level with its high ceilings and walk-out offers versatility and additional room for entertainment and possible future in-law suite. You’ll appreciate the lake view from the front windows and deck and the added bonus of a large private pond—perfect for skating in the winter, warm fires, hot cocoa and creating lasting memories.


Contact: Coleen Ure, Exp Realty, +1 613.929.6923

Rural Charm And Modern Comfort | $2,800,000

120 2nd Line, Otonabee South Monaghan, ON
Listing agent: Rennie Lowes

If you are looking for a tasteful home with lots of room for family, family events, and outdoor activities, then this home with 199 acres may be for you. The updated kitchen with a large island joins the living room that has a bank of windows that over look the ravine with a creek. From there a walkout leads to the lawn with a patio and a fire pit area.


Size: 3,500-5,000 sf


Price: $2,800,000


Listing details: In another direction from the kitchen is the family room with a vaulted ceiling that has great views of the farmland. The detached garage has room for two cars and has an unfinished loft. The farm provides a mixture of organically farmed fields, ravines, woods and a pond large enough for migratory birds.


Contact: Rennie Lowes, Exit Realty, +1 705 760 3818

322 Oxford Ave | $589,900

322 Oxford Ave, Crystal Beach, ON
Listing agent: Kelley Bartlett

Consider a home in Crystal Beach with its beautiful white sandy beaches, crystal clear water, charming shops and trendy restaurants… an extremely walkable and active community. Now offering for sale, this charming 4-season bungalow in the heart of the community is just minutes away from the sandy shores of Lake Erie.


Size: 892 sf


Price: $589,900


Listing details: A 3 bedroom, 1 bath bungalow boasting just under 900 sq feet of bright and beachy living space has plenty of natural light. Situated on 76’ x 85’ double lot, this property features no carpeting throughout, a new bathroom, recently replaced/enhanced plumbing and insulation.


Contact: Kelley Bartlett, Your Home Sold Guaranteed Realty, +1 647.272.3344

Magnificent Sunrises! | $9,998,000

26 Trafalgar Rd, Oakville, ON
Listing agent: Sam Marji

Nestled at the base of Trafalgar Road, in the heart of Old Oakville, this home boasts an impressive Walk Store of 94 out of 100. With lake front access, steps to lakefront trails, parks, the marina, boutique stores and fine dining. This expansive property boasts dimensions of 155 by 104 ft, and offers a sweeping vista of the ever-changing lake, endless horizons, and magnificent sunrises.


Size:    sf


Price: $9,998,000


Listing details: Steeped in a rich history, the house has undergone a transformation into a stunning residence spanning 10,000 sq ft across three levels. With 4 bedrooms and an additional 2, totaling 6 beautifully appointed bedrooms, and a generous 9 bathrooms, this home exudes refined luxury.


Contact: Sam Marji, Century 21, +1 647.220.9588

Piece Of History | $1,650,000

31 Wellington St, Orangeville, ON
Listing agent: Carrie Tambasco

Welcome to a piece of history nestled within the heart of Orangeville. This circa 1885 Victorian gem exudes charm and character, showcasing a fusion of stone brick and timber adorned with classical and gothic motifs. Set upon a sprawling half-acre lot lined with majestic maples, it offers an unparalleled in-town oasis.


Size:   sf


Price: $1,650,000


Listing details: Stepping inside, discerning admirers of craftsmanship will be enchanted by the preservation of both interior and exterior details. With 3 bedrooms and 3 bathrooms, the residence seamlessly blends timeless elegance with modern comfort.


Contact: Carrie Tambasco, Royal LePage, +1 519.217.7656

Listing agent: Michelle Quevillon & Kristina Tardif

This charming 4 bedroom + study, 2.5 bathroom residence built in 1873, as the inaugural brick dwelling in the vicinity seamlessly combines Victorian- era allure with contemporary comforts. Boasting gingerbread gables, original hemlock floors, soaring ceilings & imposing 15-inch baseboards flanked by 9-inch casings, the home evokes a nostalgic journey through time.


Size: 5,086 sf


Price: $1,074,999


Listing details: Yet, alongside these historic features, the home showcases modern enhancements, such as a revamped kitchen & bathrooms. Upon entry, a majestic staircase sets a tone of elegance, welcoming guests into the residence.


Contact: Michelle Quevillon & Kristina Tardif, Kristina Tardif Real Estate Group, +1 705.795.5711, 705.734.5204

Sophisticated Privacy On 52+ Acres | $6,750,000

16261 And 16249 Shaws Creek Rd, Caledon, ON
Listing agent: Sue Collis & Sarah Maclean

Two residences that are deeded separately. Primary stone house with a seamless addition providing many popular contemporary design features including a main floor primary suite and main floor laundry, eat-in kitchen with a large island and walk-in pantry. The second floor has 3 additional bedrooms each with a private bathroom.


Size:   sf


Price: $6,750,000


Listing details: Multiple walk-outs to flagstone patios and wonderful open rooms make for easy entertaining. Floor-to- ceiling windows offer long views over rolling lawns to the natural pond with water lilies and mature Koi fish, spectacular mature trees and carefully planned perennial gardens. The destination pool awaits a short stroll away.


Contact: Sue Collis & Sarah Maclean, Chestnut Park Real Estate, +1 519.837.7764, 905.872.5829

Architecturally Dramatic On 4.98 Acres | $2,495,000

605094 River Rd , Melancthon, ON
Listing agent: Sue Collis & Sarah Maclean

Custom build nestled on 4.98 acres on the sought- after Pine River. Contemporary beauty with stone, wood, metal and glass cleverly blended to showcase the natural surroundings. Screened window walls, Muskoka room and walk-outs maximize enjoyment of this charming location with soothing river sounds.


Size:   sf


Price: $2,495,000


Listing details: This four-bed, three- bath home has wonderful bespoke details, from special custom kitchen cabinetry and handles to the hand-crafted two-level masonry heater with a pizza oven, and starlight ceiling lighting. The whole second floor is a dedicate d primary bedroom suite with office/yoga studio, balcony, spa bathroom, w/i closet and second laundry.


Contact: Sue Collis & Sarah Maclean, Chestnut Park Real Estate, +1 519.837.7764, 905.872.5829