Whitby Homes with 51-99 Approx Age

Whitby Homes with 51-99 Approx Age

Welcome to Whitby, Ontario—a charming town that beautifully marries history with modern living. Nestled in Durham Region, just a stone's throw from Lake Ontario, Whitby is a vibrant community known for its rich heritage, stunning waterfront, and family-friendly atmosphere. With a population of around 130,000 residents, this picturesque town offers a perfect blend of urban conveniences and serene suburban life.

Whitby boasts a diverse range of homes, particularly those built between 51 to 99 years ago, which exude character and charm. These homes often feature unique architectural styles that reflect the town's history, from classic two-storey designs to quaint bungalows. Many of these properties have been lovingly maintained or updated, allowing you to enjoy modern comforts while basking in the nostalgic ambiance of yesteryears.

Living in Whitby means you’re never far from nature. The town is dotted with beautiful parks, walking trails, and the scenic waterfront, perfect for weekend strolls or family picnics. Plus, with a variety of shopping, dining, and entertainment options, you’ll find everything you need right at your fingertips.

Education is another strong point for Whitby, with excellent schools and community resources that cater to families and young professionals alike. Whether you’re looking for a cozy home steeped in history or a vibrant community to call your own, Whitby is a gem waiting to be discovered. Come and explore the charm of Whitby—where every home tells a story, and every street feels like home.

Newest Whitby Homes with 51-99 Approx Age

$2,350,000
4 Beds ⋅ 2 Baths ⋅ E13778468 MLS
A stunning, recently renovated custom 3 + 1 Bedroom, 2 + 1 Bath, 2 Full Kitchens, 2 Laundry Rooms, Custom Office, sidesplit set on an extraordinary mature treed 66 x 265 ft ravine lot located in the heart of Brooklin. Perfect for entertaining, this home offers a backyard overlooking a creek, with multiple outdoor living spaces including multi zone outdoor speakers, swim-spa under a custom built gazebo, wood fire space, a covered walk-out proch with gas fire place and built in bbq and sink and an insulated cabana with 2 pc washroom. The built-in heated garage featuring expoxy flooring, cabinetry & sink + more elevates this property even further. Inside, enjoy a bright open-concept design with rich hardwood floors, pot lights, heated floors in two bathrooms, mudroom and lower level family room/entertainment room, bright open-concept main floor kitchen featuring a double sized fridge/freezer, extra large gathering island and wine/coffee bar. Centrally located in the heart of Brooklin this is a must see to experience all the property has to offer.

44 Bagot Street, Whitby
$919,000
3 Beds ⋅ 2 Baths ⋅ E13767858 MLS
Charming and beautifully updated and expanded bungalow nestled in the highly sought-after community of Brooklin. This turn-key home features a bright 2+1 bedroom layout perfect for downsizers or growing families. The renovated kitchen is a chef's delight, boasting sleek granite countertops, ample cabinetry, and modern finishes. Relax and unwind in the added sunroom flooded with natural light with walkout to a covered deck, overlooking the rear yard. Large 75 X 110 ft lot offers families many options. Conveniently located near the back entrance, the versatile office/crafting room offers the ultimate space for remote work or hobbies. The fully finished basement adds excellent additional living space with a third bedroom and a second full 3 piece bathroom/laundry combo. Steps to top-rated schools, parks, historic Downtown Brooklin shops, and quick access to Highways 407 and 412 make this community one of Ontario's most sought after places to live. Move in and enjoy!

48 Garside Avenue, Whitby
$899,900
2 Beds ⋅ 2 Baths ⋅ E13759304 MLS
Beautiful 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, Crown Molding And HUGE Windows, Open To Large Formal Dining Room For Family Dinners, Includes Glass Pocket Door. 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 This Home To Appreciate Its Charm & Features!

801 King Street, Whitby
$839,900
4 Beds ⋅ 2 Baths ⋅ E13754138 MLS
Location, Location, Location! Fully detached solid brick bungalow in a charming neighbourhood right in the heart of downtown Whitby. Legal basement apartment presents an excellent opportunity for the savvy buyer to generate rental income with flexible living options. Incredible versatility for multi-generational families or investors. The main floor delivers a great layout, with some select updates and room for your personal touches. Step inside to the spacious living room with picture window and open to the dining room, functional eat-in kitchen with some modern touches and includes a convenient pantry & stackable laundry unit. 3 Bedrooms, 4 pc bathroom and a delightful 3 Season Sunroom provides a bright and relaxing space and completes the main floor. The lower level apartment features a separate side entrance, private patio, 1 bedroom plus a den/office, open concept kitchen & living area, in unit laundry, and a 3 pc bathroom with stunning glass shower. Beautifully completed and includes all appliances, bringing an outstanding opportunity for those seeking income potential. Exceptional curb appeal, custom stone patios and walkway showcase the premium outdoor finishes. One of the home's unexpected treasures is the expansive rear yard, an extra deep lot of 158 feet, fully fenced and offering a greenspace for peace and play and a gardener's delight. Steps to highly rated EA Fairman Public School & Henry Street High School. Embrace one of Durham Region's most sought-after walkable Lifestyles. Commuters will love the easy access to 401, 407, 412 & Go Transit.

400 Harris Street, Whitby
$568,900
2 Beds ⋅ 2 Baths ⋅ E13733482 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
$834,999
4 Beds ⋅ 2 Baths ⋅ E13680628 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
$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
$1,049,000
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
$1,694,999
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
$1,125,000
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
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