Downtown Whitby Homes with 51-99 Approx Age

Downtown Whitby Homes with 51-99 Approx Age

Welcome to Downtown Whitby, a vibrant neighborhood that perfectly blends historic charm with modern conveniences. Nestled in the heart of Whitby, Ontario, this area is renowned for its picturesque streets, rich cultural heritage, and a strong sense of community. Here, you’ll find an array of homes, particularly those built between 51 to 99 years ago, showcasing unique architectural styles that tell stories of the past while offering the comforts of contemporary living.

Downtown Whitby is characterized by its beautiful tree-lined streets, where classic homes with character stand proudly alongside newer developments. Many of these residences feature stunning period details such as original hardwood floors, intricate moldings, and spacious porches, making them a delight for those who appreciate craftsmanship and history. The neighborhood is ideal for families, young professionals, and retirees alike, offering a warm and welcoming atmosphere.

In addition to its charming homes, Downtown Whitby boasts an array of amenities that cater to every lifestyle. Residents can enjoy boutique shopping, delightful cafes, and diverse dining options just a stone's throw away. The area is also home to several parks, community centers, and recreational facilities, ensuring that there’s always something to do.

With its strategic location, Downtown Whitby provides easy access to major highways and public transportation, making commuting a breeze. Whether you’re exploring the local arts scene or enjoying a leisurely stroll by the waterfront, Downtown Whitby is a neighborhood that truly has it all. Come discover your new home in this enchanting community!

Newest Downtown Whitby Homes with 51-99 Approx Age

$568,900
2 Beds ⋅ 2 Baths ⋅ E13585722 MLS
Location - Location - Location!! Perfect for First time Home buyers, Renovators, Builders or Empty Nesters. Homes do not become available too often in this desirable area. This lovely detached bungalow in an ideal location is close to amenities, GO Station, walking distance to schools, parks, recreation, downtown. This Home features two bedrooms upstairs with and open concept dining/family room, the living & dining rooms that are both enhanced by large windows offering plenty of natural light & a warm, inviting feel along with a walkout to a massive Private Backyard with Mature Trees, Perfect FOR ENTERTAINING!! Separate side entrance leads to the basement. Roof and furnace is newer and in great condition. YOU ARE JUST MINUTES TO THE POPULAR PEEL PARK , THIS HOME has a TON of potential ! Opportunities like this are rare. So please do not miss out!!!!

917 Green Street, Whitby
$580,500
5 Beds ⋅ 2 Baths ⋅ E13578022 MLS
Welcome to 322 Rosedale Drive, Whitby! Nestled in a mature, family-friendly neighbourhood, this 3-bedroom, 2-bathroom semi-detached bungalow offers an exceptional opportunity for first-time buyers, investors, or anyone looking to add their own personal touch. With approximately 1,040 sqft above grade, plus a partly finished basement, this home features a functional layout with endless potential. The bright, open-concept living and dining area showcases hardwood floors and a charming bay window overlooking the front garden. The updated kitchen is equipped with quartz countertops, a breakfast bar, stylish backsplash, large pantry, and ample cabinetry, making it both functional and inviting. The partly finished basement expands the living space with a spacious rec room featuring a large above-grade window, an additional room ideal for a home office, gym, or hobby room, and a separate side entrance offering excellent in-law suite or income potential. Ideally located just minutes from highly rated schools, parks, shopping, transit, and everyday amenities, this home combines a desirable location with solid bones and outstanding potential. Whether you're looking to renovate, customize, or invest, this is a fantastic opportunity to build equity in one of Whitby's established communities.

322 Rosedale Drive, Whitby
$649,900
4 Beds ⋅ 2 Baths ⋅ E13570064 MLS
Welcome to 341 Rosedale Drive in Whitby! Situated in a desirable family-friendly neighborhood, this 3+1 bedroom, 2 bathroom bungalow offers an excellent opportunity for first-time buyers, investors, or those looking to add their own personal touches. Featuring approximately 1,012 sq. ft. above grade (plus a partly finished basement), the home offers a functional layout with plenty of potential. Roof 2013.Enjoy the privacy of having no neighbor's behind while being just minutes from highly rated schools, parks, shopping, and everyday amenities. The basement features a spacious rec room with a cozy gas fireplace, a 3-piece bathroom, an additional room ideal as a fourth bedroom, home office or hobby room, and a separate side entrance offering excellent in-law or income potential (subject to any required approvals).With solid bones, a sought-after location, and endless possibilities, this is a fantastic opportunity to renovate, customize, and build equity in one of Whitby's established neighborhood.

341 Rosedale Drive, Whitby
$924,900
2 Beds ⋅ 2 Baths ⋅ E13487684 MLS
Welcome to This Mid Century Modern Rancher In The Heart Of Desirable Historic Downtown Whitby. A Quiet Picturesque Neigborhood Full Of Mature Trees, Walk To GO Station, Downtown Shopping , Library, Parks And More. Quick 401 Access, Ideal For Commuters. Lovingly Maintained 2 Bedroom Bungalow On Oversized Rare 81' x 136 ' Lot Landscaped With Perennials, Shrubs And Shade Trees. Long Brick Walkway Leads You To The Large Entryway Of This Sunny Home. Open Concept Floor Plan Includes Spacious Main Living Room With Hardwood Floors, Original Wood Burning Fireplace And HUGE Windows, Open To Large Formal Dining Room For Family Dinners. Kitchen Boasts Gas Stove, Stainless Steel Appliances And Breakfast Room With Built-In Banquette Seating And Double Garden Doors To Expansive Backyard. Huge Primary Bedroom Is An Incredible Sanctuary With Sunken Sitting Area, Electric Fireplace And Double Doors With Views To The Gorgeous Gardens. 2nd Bedroom Is Nicely Sized With Full Length Wardrobe And Large Window. Recently Updated Main Bath Features Porcelean Tile, A Custom Walk In Shower, Built-In Bench And Rain Head. Substantially sized Recreation Room On The Lower Level With Gas Fireplace, Premium Lanmiate Floors And 3 Piece Bathroom. Breath Taking Private, Fully Fenced Park Like Backyard With Beautiful Perennial Gardens, Composite Deck, Interlock Brick Patio, Water Feature & Garden Shed. Great For BBQ'ing, Entertaining Or Just Enjoy The Birds & Wild Life On Your Own. You Need To View It To Appreciate It!

801 King Street, Whitby
$529,900
3 Beds ⋅ 2 Baths ⋅ E13439882 MLS
Beautifully updated, ground-level 3-bedroom condo apartment in the heart of Downtown Whitby! This spacious and functional layout offers the rare convenience of two full bathrooms, including a newly added 3-piece bath and a beautifully refreshed second bathroom (both 2025). Seamlessly blending convenience and space, this home is ideal for families, first-time buyers, or downsizers looking to establish roots in a highly desirable, walkable community.Step into bright, inviting living spaces and a modern kitchen featuring top-tier 2025 appliances, including a fridge, dishwasher, over-the-range microwave, and full-size washer & dryer. The true crown jewel of this property is your own privately owned, fenced front lawn-a rare condo luxury that provides a safe, private outdoor oasis for kids to play, or for hosting weekend family gatherings and gardening.With three generous bedrooms, an owned separate storage room, a high-efficiency heat pump for climate control (2021), and updated hydro (2021), this turn-key home showcases true pride of ownership throughout. Perfectly situated in a family-oriented neighbourhood, perfectly situated in a prime location for family living & for commuters, you are just steps away from excellent local schools like Julie Payette Public School, C.E. Broughton Public School, and St. Theresa Catholic School. Enjoy effortless access to downtown parks, boutique shopping, diverse dining, and transit. A fantastic opportunity to own a move-in ready home!

540 Mary Street E Unit 2, Whitby
$815,000
4 Beds ⋅ 1 Baths ⋅ E12947154 MLS
Beautiful 2+2 bedroom back-split bungalow featuring an open-concept layout with hardwood floors and a bright living room with gas fireplace. Spacious kitchen and dining area on the main level. Upper level offers a primary bedroom, second bedroom, and office with walkout to a sunroom. Enjoy a wrap-around deck and saltwater pool-perfect for summer. Lower level includes two additional versatile rooms, laundry, and generous storage.

920 Greenwood Crescent, Whitby
$989,000
4 Beds ⋅ 2 Baths ⋅ E12894560 MLS
Mature lot with a beautiful Garden , 3 bedrom + den. Located at 1002 Dunlop Street in Whitby, this charming home sits on a mature lot featuring a beautifully landscaped garden that offers both privacy and a serene outdoor setting. Offering approximately 1,500 sq. ft. of well-designed living space, the property includes three spacious bedrooms plus a versatile den, ideal for a home office or additional living area. The primary bedroom features a private 4-piece ensuite, while the large family room with a cozy wood-burning fireplace provides the perfect space for relaxing or entertaining. The kitchen is both functional and flexible, complete with a movable island on wheels for added convenience. Recent updates include a newer deck (2021) and an updated garage, enhancing both the appeal and functionality of this well-maintained home in a desirable, established neighbourhood.0 SQ .one ensuite 4 pc.Large Family room with Wood burning Fireplace, Kitchen with moveable Island on wheels, newer Deck 2021,newer garage, Dont miss your oppourtunity!

1002 Dunlop Street, Whitby
Start Your Search