Whitby Homes with 100+ Approx Age

Whitby Homes with 100+ Approx Age

Welcome to Whitby, Ontario – a charming town steeped in history and brimming with character! Nestled along the shores of Lake Ontario, Whitby offers a delightful blend of small-town charm and modern conveniences. With its picturesque waterfront, vibrant downtown, and thriving community, it’s no wonder that Whitby has become a sought-after destination for families, professionals, and retirees alike.

One of the most captivating aspects of Whitby is its rich architectural heritage. The town boasts an array of homes with over 100 years of history, showcasing stunning craftsmanship and unique designs that tell a story of the past. These historic residences are often characterized by their intricate woodwork, high ceilings, and expansive gardens, inviting you to step back in time while enjoying contemporary amenities. Living in one of these homes means becoming part of a legacy, where every corner holds a piece of Whitby’s storied past.

Whitby is not just about beautiful homes; it’s also a community that values connection and culture. With numerous parks, recreational facilities, and cultural events throughout the year, residents can enjoy an active lifestyle. From the scenic trails along the waterfront to the lively farmers' markets, there’s always something happening in this vibrant town.

Whether you’re exploring the charming streets lined with historic homes or enjoying the local cuisine at one of Whitby’s many eateries, you’ll quickly discover why this town is a wonderful place to call home. Experience the perfect blend of history and modern living in Whitby, Ontario – where every home tells a story!

Newest Whitby Homes with 100+ Approx Age

511 Centre Street S, Whitby
$1,399,900
4 Beds ⋅ 4 Baths ⋅ E13830758 MLS
INCREDIBLE century home in highly sought-after Olde Whitby, blending timeless charm & character with exceptional modern updates! Upgraded top to bottom with immaculate finishes, custom millwork, crown moulding, pot & sconce lighting, built-in speakers, shiplap & thoughtful details throughout. Set on a manicured 58 x 136 ft lot with lush gardens, ample parking, cozy front porch & detached garage with 6.64 x 4.39 m workshop addition. The private backyard oasis features a wrought-iron-gated inground pool, custom pool house, natural stone patio, mature trees, pergola, gazebo & ambient exterior lighting. Inside feels straight from the pages of a magazine! Elegant living room with wainscotting & front garden views. Formal dining room with stunning waffle ceiling. Gourmet kitchen with granite counters, subway tile backsplash, extended cabinetry, under & in-cabinet lighting, pantry, breakfast bar & breakfast nook with built-in chef's desk, seating & garden-door walkout to the backyard. Convenient anteroom with heated ceramic floors & picturesque garden views. Upstairs offers 3 generous bedrooms with closet organizers, including a beautiful primary retreat with beamed ceiling & shiplap detail. Fabulous loft provides additional living space with gas fireplace, built-in bookcase & desk, 2pc bath, vaulted ceiling & skylight-perfect for a home office, study or 4th bedroom. Finished basement with separate side entry, rec room, built-in closet, 3pc bath, above-grade windows, laundry & ample storage. Homes like this rarely come to market! Steps to parks, schools & transit, with easy Hwy 401 access, GO Train & close to downtown Whitby shops, restaurants & amenities. A truly special home!

511 Centre Street S, Whitby
130 Myrtle Road E, Whitby
$1,199,000
4 Beds ⋅ 3 Baths ⋅ E13826554 MLS
Welcome to 130 Myrtle Rd E, a truly special country retreat full of warmth, character and endless possibility. Set in the charming community of Ashburn, this cottage-inspired century home offers the cozy feeling of a weekend getaway with the space and versatility for everyday living.From the moment you step inside, the rich wood beams, timeless details, inviting fireplaces and warm architectural charm create a home full of history and heart. This property is ideal for someone who appreciates character, craftsmanship and the opportunity to make a home their own.The layout offers generous principal rooms, unique living spaces and a separate in-law suite with its own entrance, kitchen, loft bedroom and laundry-perfect for extended family, guests, a creative studio, or added flexibility. Outside, the approximately one-acre property offers room to garden, entertain, relax and enjoy the peaceful country setting, along with multiple outbuildings for storage, hobbies or workshop potential. This is not a cookie-cutter home; it is a rare opportunity for someone with vision to create something truly beautiful while preserving the charm and soul that make this property special. A warm, welcoming home for those who love character, cozy living and the feeling of a private country escape.

130 Myrtle Road E, Whitby
780 Garden Street, Whitby
$1,995,000
5 Beds ⋅ 4 Baths ⋅ E13799118 MLS
Dating back to 1845, the Mayfield Residence is a truly distinguished Whitby heritage estate set on more than an acre of beautifully landscaped grounds. This remarkable property offers a rare opportunity to own a piece of Whitby history while enjoying the space, privacy and versatility of an exceptional residential setting. The stately main residence showcases the character and presence of a historic estate, with a flexible floorplan offering a variety of possibilities for modern family living. Generous living spaces, timeless architectural details and the expansive property create an impressive backdrop for both everyday life and entertaining. A separate 1,100 sq. ft. Coach House adds exceptional versatility, featuring covered parking for three vehicles along with abundant storage. The extensive grounds provide plenty of outdoor space to relax, entertain and enjoy the privacy of this remarkable setting, with ample parking for family and guests. Adding further flexibility, the property's zoning permits up to four residential units, offering potential for extended family living, additional accommodations or future income opportunities. The existing mixed-use zoning also permits office uses, providing the option to incorporate a professional component if desired. A rare offering where history, scale and versatility come together, the Mayfield Residence presents an extraordinary opportunity to own an iconic Whitby property with endless possibilities for its next chapter.

780 Garden Street, Whitby
780 Garden Street, Whitby
$1,995,000
4 Baths ⋅ E13798958 MLS
The Mayfield Residence, dating back to 1845 is a distinguished Whitby estate offering a rare opportunity for commercial and investment use. Situated on more than an acre of beautifully landscaped grounds this historic property presents a unique blend of character, versatility and modern business potential. The existing mixed-use zoning permits all office uses, creating an ideal setting for medical, dental or chiropractic practices, law and accounting firms, financial services, consulting businesses, design studios, wellness operators and more. The grand main residence offers a versatile layout that can be tailored to a variety of professional uses or configured to combine residential and commercial space, providing flexibility for both owner-users and investors. A separate 1,100 sq. ft. Coach House provides covered parking for three vehicles and generous storage, while the surrounding grounds accommodate an additional eleven exterior parking spaces. Zoning also permits up to four residential units on the property, further expanding its income and redevelopment potential. Signage available on Garden St. for good visibility! An exceptional heritage property with multiple possibilities, the Mayfield Residence offers an uncommon opportunity to bring together historic character, functional commercial space and long-term investment potential.

780 Garden Street, Whitby
311 Byron Street N, Whitby
$1,079,000
4 Beds ⋅ 2 Baths ⋅ E13755610 MLS
Get character and soul of late 1800s local history without losing a single convenience of modern urban living. Step inside the original front door with its working push bell and fall in love with soaring ceilings, high baseboards, original wide-plank hand-hewn pine floors, and large principal rooms-juxtaposed by a breathtaking primary suite featuring reclaimed Madawaska River log floors, a skylight, yard views, and a walk-in closet roughed-in for a future ensuite. A large secondary bedroom features a semi-ensuite bathroom with bath and shower, while the 3rd and 4th bedroom is perfect for kids, family, office or guests. Enjoy convenient main floor laundry, with heavy lifting done: a 2025 roof, 2024 furnace, newer windows, added attic insulation, and copper electrical - leaving you free to easily add your own touches. The crowning jewel of this property is a deep, near 1/4-acre fully fenced lot complete with an in-ground sprinkler system, gas BBQ line, perennial beds, and shade trees perfect for family games and pets to play, ample parking for 3-5 cars or an RV, plus a separate basement entrance to a lower level offering outstanding potential. Possible room to custom build an accessory dwelling unit or detached garage/workshop/studio - subject to municipal regulations and requirements. Recognized on Whitby's Perry's Plan for exceptional historic character, this 4-bedroom home in the Gothic Revival style-crafted by local artisan carpenter Michael Marshall-blends authentic architecture with contemporary everyday comfort. Crucially, enjoy NO municipal heritage designation or restrictive covenants for total ownership freedom in a century home. Walk to local parks, splash pads, top public, Catholic, French Immersion, and prestigious private school options, plus the historic downtown Four Corners district for top dining, cafes, pubs, and shops. Stay connected to the city-easy access to Whitby GO, Durham Transit, and HWYs 401, 412, and 407 makes any commute a breeze.

311 Byron Street N, Whitby
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