Whitby Homes with 51-99 Approx Age

Whitby Homes with 51-99 Approx Age

Welcome to Whitby, Ontario—a charming town that beautifully balances suburban tranquility with vibrant community life. Nestled along the shores of Lake Ontario, Whitby is celebrated for its picturesque landscapes, rich history, and a strong sense of community. With easy access to major highways and a convenient GO Transit service, residents enjoy a seamless commute to Toronto while relishing the serene environment of their hometown.

One of the appealing aspects of Whitby is its diverse housing market, particularly homes that fall within the 51-99 age range. These properties often boast unique architectural features and a sense of character that new builds may lack. Many of these homes are set in established neighborhoods, surrounded by mature trees and well-kept gardens, creating a warm and inviting atmosphere.

Living in a home with a bit of history means you’re not just buying a property; you’re becoming part of a story that has been unfolding for decades. These homes often come with spacious layouts and charming details, making them perfect for families looking for a blend of comfort and nostalgia.

Whitby is also home to numerous parks, recreational facilities, and cultural attractions, ensuring that residents have plenty of opportunities for leisure and entertainment right at their doorstep. Whether you’re exploring the scenic waterfront or enjoying community events, Whitby offers a lifestyle that is both enriching and enjoyable.

If you’re considering a move to this delightful town, homes with a vintage flair await you—each one a unique gem in the heart of Whitby. Come discover the perfect blend of history and modern living!

Newest Whitby Homes with 51-99 Approx Age

$698,000
3 Beds ⋅ 2 Baths ⋅ E13593922 MLS
This Is A Linked Property Bright, Spacious, And Beautifully Maintained, This Modern 3-Bedroom, 2-Bathroom Home Offers The Perfect Blend Of Style, Comfort, And Functionality. The Thoughtfully Designed Layout Features Generous Living Spaces Filled With Natural Light, While The Finished Basement Provides Additional Room For A Family Recreation Area, Home Office, Or Gym. Outside, The Home Boasts Fantastic Curb Appeal And A Private Backyard (A New Fence 2023), Complete With New Deck (2023) - Perfect For Relaxing Or Entertaining. Backing Onto Scenic Walking Paths And Green Space, You'll Enjoy Peaceful Views (With No Neighbours Behind) And Direct Access To Nature Right From Your Backyard. This Is An Exceptional Opportunity To Own A Move-In-Ready Home In A Desirable Setting That Combines Modern Living With Outdoor Enjoyment. Conveniently Located Mins To Hwy, Shops, Amenities, Schools & So Much More. Upgrades Include; New Furnace (2025), Air Conditioner (2021), Attic And Basement Insulated (2021), Garage Door (2025), Electrical Panel Replaced (2021), Basement Windows (2023), Upper Floor Windows (2025), Hot Water Tank (2024).

93 Kirby Crescent, 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
$788,000
3 Beds ⋅ 1 Baths ⋅ E13582544 MLS
OPEN HOUSES CANCELED! Some properties are defined by what they are today. Others by what they have the potential to become. Set on an exceptional 85 x 139 ft lot in one of Brooklin's most established neighbourhoods, 94 Way Street offers a rare opportunity to create something truly your own. Whether you envision thoughtfully updating the existing 1,334 sq. ft. bungalow, adding a second storey, or designing a custom home from the ground up, the possibilities begin here.The home has been well maintained and features three bedrooms, generous principal rooms, a finished lower level, an attached double garage, and updated mechanicals, making it easy to enjoy today while you plan for tomorrow. Surrounded by mature cedar hedges along the side and rear, with ravine views and no neighbours directly across the street, the property offers a level of privacy and openness that is becoming increasingly difficult to find. Located just minutes from downtown Brooklin, parks, schools, restaurants, shopping, and convenient access to Highways 407 and 412.Bring your imagination. Create your vision. Make it your own. Disclaimer: All digital renderings, illustrations, floor plans, and visual enhancements are artist's concepts and are intended for illustrative purposes only. Images may have been digitally enhanced or modified to showcase potential design ideas and do not necessarily reflect the current condition of the property. Nothing contained herein shall be interpreted as a representation or warranty that the property will be completed, renovated, or delivered in the manner depicted. No representation is made that any proposed improvements have been approved, nor that any permits have been obtained or will be issued. Buyers are encouraged to conduct their own independent investigations and satisfy themselves with respect to any future plans or development potential.

94 Way 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
$1,125,000
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
$899,000
3 Beds ⋅ 1 Baths ⋅ E13445708 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
$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
$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
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