Downtown Whitby Homes with 100+ Approx Age

Welcome to Downtown Whitby, a charming neighborhood that beautifully marries historic character with modern convenience. Nestled in the heart of Whitby, Ontario, this vibrant area is known for its rich history, friendly community, and a diverse array of amenities that cater to every lifestyle.

One of the standout features of Downtown Whitby is its collection of homes, many of which boast an impressive age of 100 years or more. These charming residences reflect the architectural styles of yesteryear, offering a unique glimpse into the past while providing the comforts of contemporary living. From classic Victorian houses to quaint bungalows, each home tells its own story and adds to the neighborhood's distinctive charm.

The streets of Downtown Whitby are lined with mature trees and beautifully manicured gardens, creating a picturesque setting that feels both welcoming and serene. Residents enjoy easy access to local parks, boutique shops, and delightful cafes, making it a perfect place for leisurely strolls or weekend outings. The community is also home to several cultural landmarks, including art galleries and theaters, ensuring that there’s always something exciting happening nearby.

Families will appreciate the excellent schools and recreational facilities in the area, while commuters benefit from convenient public transport options and quick access to major highways. Whether you’re looking to settle down in a historic home or seeking a vibrant community to call your own, Downtown Whitby offers a perfect blend of charm, convenience, and a welcoming spirit. Come and discover the timeless allure of this enchanting neighborhood!

Newest Downtown Whitby Homes with 100+ Approx Age

$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

$1,149,000

4 Beds ⋅ 2 Baths ⋅ E13755610 MLS

Get the grace, prestige, and soul of 1800s history without losing a single convenience of modern urban living. Recognized on Whitby's Perry's Plan for its 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. 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 gracious 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. Enjoy main floor laundry, updated windows, a late 2024 furnace, a 2025 roof, extra attic insulation, and a custom-fitted kitchen engineered for efficiency. The crowning jewel of this property is a deep, near 1/4-acre fully fenced lot complete with an in-ground sprinkler system, perennial beds, and shade trees perfect for family and pets, ample parking for 3-5 cars or an RV, plus a separate basement entrance offering outstanding potential. 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. No need to move far away from 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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