Whitby Homes with 51-99 Approx Age

Whitby Homes with 51-99 Approx Age

Welcome to Whitby, Ontario – a charming town that perfectly blends rich history with modern living. Nestled in Durham Region, just a stone's throw from Lake Ontario, Whitby boasts a vibrant community atmosphere, stunning waterfront parks, and an array of recreational opportunities that make it an ideal place to call home.

Whitby is renowned for its picturesque downtown area, featuring quaint shops, delightful cafes, and a bustling farmers' market that showcases the best of local produce. The town is also home to the scenic waterfront trail, inviting residents to enjoy leisurely walks, cycling, or simply soaking in the serene views of the lake. With excellent schools, abundant green spaces, and a strong sense of community, Whitby is perfect for families, retirees, and young professionals alike.

For those seeking a home in this delightful town, Whitby offers a diverse selection of properties, particularly homes with an approximate age of 51-99 years. These charming residences often feature unique architectural details and character that new builds simply can't replicate. Imagine living in a home that tells a story, with vintage charm and modern updates that cater to today's lifestyle. Many of these homes are nestled in established neighborhoods, providing a sense of community and connection with your neighbors.

Whether you're drawn to the historic character of these homes or the vibrant lifestyle that Whitby has to offer, you'll find a welcoming community that feels like home. Explore the possibilities in Whitby and discover your perfect abode in this beautiful Ontario town!

Newest Whitby Homes with 51-99 Approx Age

$849,000
3 Beds ⋅ 1 Baths ⋅ E13628316 MLS
Welcome to this exceptional and incredibly rare offering. Nestled in the highly desirable family friendly Olde Brooklin neighbourhood. Featuring 3 spacious bedrooms, a large kitchen and dining area with a separate living room and gas fireplace. Enjoy a coffee on the covered front porch. Move in ready! Partially finished basement has great in-law suite potential with above grade windows. Minutes to shopping, schools, parks, 407 and the new Whitby sports complex.

12 Simcoe Street, Whitby
$829,999
4 Beds ⋅ 2 Baths ⋅ E13618326 MLS
Welcome to 326 Cochrane Street, a rarely offered, beautifully maintained all-brick bungalow situated on a 69 x 136 ft. lot. Nestled on the border of two of Whitby's most sought-after neighbourhoods - Downtown Whitby and Lynde Creek. Offering timeless charm, exceptional versatility, and outstanding future potential, this move-in-ready home is a rare find. The bright and inviting main floor features a functional layout with 3 spacious bedrooms, comfortable living and dining spaces, and thoughtfully designed storage, including brand-new custom closet systems in front hall and primary bedroom (2026) that enhances everyday functionality. The fully finished basement significantly expands the living space with an additional bedroom, dedicated office, large recreation room, versatile playroom or den, and brand-new carpeting (2026) throughout. Existing plumbing and electrical hookups remain in place, allowing the lower level to be easily converted into a 2 bedroom in-law suite or income-generating apartment-an ideal opportunity for multigenerational living or future rental potential The home has been freshly painted and updated with stylish new light fixtures, door hardware, and modern accents - creating a fresh, welcoming feel throughout. Outside, the oversized backyard offers endless possibilities for entertaining, gardening, family enjoyment, or the potential to build a future addition, maximizing the value of this impressive lot. Perfectly located across the street from a top tier elementary school and just a short walk to Downtown Whitby's vibrant shops, restaurants, cafés, grocery stores, parks, and playgrounds. This exceptional home also provides convenient access to GO Transit and Highway 401 for an easy commute.

326 Cochrane Street, Whitby
$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
$549,900
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
$1,099,000
4 Beds ⋅ 3 Baths ⋅ E13577408 MLS
Welcome to this beautifully maintained four bedroom 2 story home, ideally situated on a quiet family court in one of Whitby's sought after neighborhoods. It features a pie-shaped lot backing onto peaceful conservation area. Large inground heated pool with terrace seating areas and scenic natural views and gardens. Inside, you will find spacious principal rooms, natural light throughout, a functional layout for family and entertaining, with a games room perfect for growing families. The upper level offers 4 large bedrooms, 4 pc main bath and 2 piece ensuite. The main floor family room has a corner gas fireplace and walk out to deck and yard. Upgraded windows, siding, insulation, kitchen, baths, hardwood flooring, landscaping and pool pump. Survey on file. Walk to parks, bike trails, shopping, schools, local transit and major highways. This home shows pride of ownership, a rare opportunity to own a home that combines location, privacy, and resort-style backyard living in the heart of Whitby.

19 Ann Arbour Court, 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
$1,699,000
5 Beds ⋅ 2 Baths ⋅ E13563186 MLS
Almost 2-acre private estate in prestigious Williamsburg. Enjoy the panoramic view of your treed lot with pond and the pristine Lynde Creek from your glass-paneled balcony with composite decking. You will have a spacious 3-car garage and the expansive paved driveway can accommodate 14 vehicles. The lower area has been upgraded with premium vinyl plank flooring. The living room's floor to ceiling glass windows allow plenty of sunlight. New Blinds. A UNIQUE, ONE-OF-A-KIND PROPERTY OFFERING THE EXPERIENCE OF LUXURIOUS COUNTRY LIVING CLOSE TO THE CITY.

3505 Cochrane Street, 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
$809,000
4 Beds ⋅ 2 Baths ⋅ E13471266 MLS
Exceptional opportunity in Whitby's prestigious Williamsburg community. This detached all-brick bungalow features a versatile 3+1 bedroom, 2-bathroom layout, feeding into top-tier local schools like Williamsburg PS. The main level offers a bright, functional floor plan with three spacious bedrooms. A fully finished lower level adds a fourth bedroom, full bath, and recreation area-ideal for an in-law suite or premium rental income. 6-vehicle parking capacity (5 driveway + 1 Carport )Exceptional opportunity in Whitby's prestigious Williamsburg community. This detached all-brickbungalow features a versatile 3+1 bedroom, 2-bathroom layout, feeding into top-tier local schoolslike Williamsburg PS.The main level offers a bright, functional floor plan with three spacious bedrooms. A fully finishedlower level adds a fourth bedroom, full bath, and recreation area-ideal for an in-law suite orpremium rental income. 6-vehicle parking capacity (5 driveway + 1 Carport )

922 Centre Street N, Whitby
$1,150,000
4 Beds ⋅ 2 Baths ⋅ E13116612 MLS
Welcome to 233 Wellington Street! One of Whitby's premier locations in the west-end, on a street that ends at Lynde Creek. Features large treed lots with custom homes. This house was built in 1965 and is 2198 sf as per MPAC. All on a 75'x166' lot. This property is being sold by the original owner. Updates include the kitchen, shingles (2015), garage door (2025), and most windows. Features four bedrooms, 1-1/2 baths, a main floor family room, hardwood floors in various rooms, and a recreation room. This is a great place to call home! This property is sold "as is" condition with no representations or warranties.

233 Wellington Street, Whitby
$879,900
3 Beds ⋅ 1 Baths ⋅ E13022532 MLS
Some lots just make sense. This one makes a statement. Measuring 82 x 145 feet and flanked by custom-built homes on one of Brooklin's most sought-after streets, this is the kind of property serious buyers quietly wait for. Builder can provide a custom built home or do your own thing. A mature, established neighbourhood. A generous, fully fenced lot. And a location that checks every box before you've even drawn up plans. The existing bungalow - 1,107 sq. ft., 3 bedrooms, 1 bathroom, metal roof, detached garage - is a solid starting point for a thoughtful renovation, or simply a placeholder while you design something extraordinary from the ground up. Either way, the lot does the heavy lifting. Top-rated schools, parks, dining, and seamless access to Highways 407 and 412 put everything within easy reach - without sacrificing the quiet, community feel that makes Brooklin such a compelling place to plant roots. Lots of this calibre, on streets of this reputation, don't surface often. When they do, they don't wait.

56 Queen Street, 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
Start Your Search