Whitby Homes with 31-50 Approx Age

Whitby Homes with 31-50 Approx Age

Welcome to Whitby, Ontario – a charming town that beautifully blends the tranquility of suburban living with the vibrancy of urban amenities. Nestled in Durham Region, Whitby is renowned for its picturesque waterfront along Lake Ontario, historic downtown, and lush green spaces. With a rich history dating back to the early 1800s, this community boasts a unique character that attracts families, professionals, and retirees alike.

One of the standout features of Whitby is its diverse housing market, particularly homes aged between 31 to 50 years. These residences often reflect the timeless appeal of classic architecture while offering modern conveniences that cater to today’s lifestyle. Many of these homes are situated in established neighborhoods, providing a sense of community and familiarity. With spacious layouts, mature trees, and well-maintained yards, these properties are perfect for those seeking a blend of comfort and character.

Whitby’s strategic location makes it an ideal choice for commuters, with easy access to Toronto via Highway 401 and the GO Transit system. Residents enjoy a plethora of amenities, including shopping centers, restaurants, and recreational facilities. The town is also home to excellent schools and parks, making it a family-friendly destination.

Whether you’re looking for a cozy bungalow or a spacious family home, Whitby offers a variety of options that cater to different lifestyles. Embrace the charm of this vibrant community and discover your dream home in Whitby, where history meets modern living!

Newest Whitby Homes with 31-50 Approx Age

$1,534,900
4 Beds ⋅ 4 Baths ⋅ E13677874 MLS
Some homes reveal their quality slowly. 63 Kennett Drive makes its impression before you reach the front door. Set beneath a canopy of mature trees, this distinguished brick residence feels established, private and beautifully at home in its surroundings. Manicured gardens frame the entrance, while the double garage and classic architecture give the property a quiet sense of presence. Inside, the mood is equally considered. A gracious foyer opens to generous principal rooms where rich hardwood, soft natural light and an understated palette create spaces that feel elegant without feeling formal. The living room invites conversation; the dining room was made for long dinners, celebrations and evenings that extend well beyond dessert. The kitchen is where the home truly comes alive. Upgraded cabinetry rises dramatically against granite surfaces and stainless steel, while an expansive peninsula creates a natural gathering place. Beyond it, the breakfast area is wrapped in windows, filling the space with sunlight and garden views. Patio doors lead to a private backyard surrounded by mature greenery. It is a setting made for unhurried summer evenings, dinner outside and weekends with nowhere else to be. Enjoy the beautiful salt water pool with waterfall feature, overlooking the ravine. What distinguishes 63 Kennett Drive isn't any single feature. It's the way the home comes together-the established setting, the natural light, the generous rooms, the connection to the outdoors and the sense that everything has found its place. This is not a house trying to impress. It simply does. For those who value warmth over excess, substance over spectacle and a home that feels as good as it looks, 63 Kennett Drive is something special. Steps from top-rated schools, parks, walking trails, and Whitby's vibrant downtown, with quick access to public transit, Highways 407, 412, and 401, this is a rare opportunity to own one of the community's most sought-after home.

63 Kennett Drive, Whitby
$1,324,900
5 Beds ⋅ 3 Baths ⋅ E13677394 MLS
Beautifully maintained and updated executive family home nestled in one of Whitby's most sought-after communities, Queens Common. Offering approximately 3,262 sq. ft. of thoughtfully designed living space, plus a partially finished basement, this exceptional residence perfectly blends elegance, comfort, and functionality. Step inside to discover spacious principal rooms designed for both everyday living and sophisticated entertaining. The main floor features a private office with custom built-in bookcases and desk, ideal for working from home, along with a formal dining room and a separate living room with vaulted ceiling and gas fireplace. At the heart of the home is the sun-filled gourmet kitchen, showcasing Silestone countertops, a custom stone backsplash, stainless steel appliances, a pantry, and a convenient built-in workstation. The kitchen flows seamlessly into the bright breakfast area and inviting family room with fireplace, creating the perfect space for family connection. Both areas offer walk-outs to the spectacular backyard retreat. Outside, enjoy your own private oasis featuring a heated in-ground pool, expansive deck, gazebo, mature landscaping, and a fully fenced yard surrounded by lush greenery-an ideal setting for summer entertaining, relaxation, and family fun. The upper level offers four generously sized bedrooms, including a luxurious primary suite complete with a cozy sitting area, walk-in closet, and spa-inspired 5-piece ensuite. The partially finished basement provides additional living space and endless opportunities for recreation, hobbies, or future customization. Additional features include gas and wood-burning fireplaces, direct garage access, a convenient main-floor laundry room, and pride of ownership throughout. Ideally located close to top-rated schools, parks, scenic walking trails, shopping, restaurants, public transit, and all major amenities. Commuters will appreciate quick access to Highways 401, 407 and 412.

49 Rothean Drive, Whitby
$799,999
4 Beds ⋅ 3 Baths ⋅ E13650778 MLS
Welcome to 20 Old Colony Dr, a gorgeous, move-in-ready haven nestled in Whitby's highly coveted, family-friendly Pringle Creek community. This exceptional property boasts a rare, sprawling pie-shaped lot that expands to an impressive 60 feet at the rear-framed by mature trees for ultimate privacy. Your private backyard oasis awaits, complete with a spacious deck and a refreshing above-ground pool, perfect for summer entertaining and family fun. Out front, enjoy the convenience of a double-car garage with a no-sidewalk driveway (allowing for maximum parking). Inside, the main level shines with brand-new flooring and the ultimate convenience of main-floor laundry. Upstairs, retreat to the spacious primary suite, featuring a generous walk-in closet and a beautiful 4-piece ensuite. Located steps from top-tier schools, daycares, shopping, and dining, and just minutes from the Whitby GO Station, Hwy 401, and Hwy 407, this home perfectly blends suburban tranquility with an effortless GTA commute.

20 Old Colony Drive, Whitby
$1,499,900
5 Beds ⋅ 4 Baths ⋅ E13648748 MLS
Exceptional executive residence situated on a premium pie-shaped ravine lot in the highly sought-after Queen's Common community of West Whitby. Ideally located close to parks, scenic walking trails, top-rated schools, shopping, restaurants, the library, charming downtown Whitby, and convenient access to Highways 401, 412 and 407. Beautifully updated from top to bottom, this impressive home showcases hardwood flooring throughout the main and second levels, designer lighting, pot lights, crown mouldings, and quality finishes throughout. The thoughtfully designed main floor offers a private study or office, elegant formal living room with vaulted ceiling, and a spacious family room with gas fireplace open to the renovated chef-inspired kitchen. Featuring quartz countertops, a centre island, built-in dining table and desk, premium stainless steel appliances, this kitchen is designed for both everyday living and entertaining. Walk out from the breakfast area to your private backyard oasis complete with a party-sized interlocking patio, heated in-ground pool, gazebo, pool cabana/change room, and spectacular ravine setting. The spacious primary retreat offers a sitting area and beautifully renovated 5-piece ensuite. Three additional bedrooms, including one with a vaulted ceiling and walk-in closet, provide exceptional family accommodation. Renovated bathrooms, main floor laundry with separate side entrance and direct garage access add everyday convenience. The finished basement expands the living space with a second kitchen featuring a breakfast bar, dedicated office area, large recreation room, and 3-piece bathroom-ideal for extended family or entertaining. Professionally landscaped with interlocking stone walkways and patios, mature trees, perennial gardens, and a dry riverbed. A rare opportunity to own a beautifully renovated executive home on one of Queen's Common's most desirable ravine lots.

75 Allayden Drive, Whitby
$499,900
3 Beds ⋅ 3 Baths ⋅ E13644888 MLS
Court Location in Prime Central Whitby. Attention Renovators and contractors. Good bones in this home, Solid 3 bedroom home on large Pie shaped lot. Drive Through Single Garage. Large Primary Bedroom with Semi Ensuite and Large Walk in Closet. SHower and Sink in Basement, Toilet Plumbing not tied in. Roof Shingles Approx 2.5 Yrs. Property being Sold As Is. Seller makes no warranties

41 Harrison Court, Whitby
$989,000
3 Beds ⋅ 4 Baths ⋅ E13644750 MLS
Completely renovated and never lived in since completion, this stunning home offers over 2,000 sq. ft. of finished living space with quality upgrades throughout. Featuring 3 bedrooms, 3.5 bathrooms, and a 2-car driveway, the home also includes an extended kitchen island, quartz counters, matching backsplash, and luxury hardware. The finished basement adds a full ensuite shower and office, while professionally finished hardscaping, brand-new sod, upgraded doors, and an oversized garage complete this impressive home on a quiet street.

16 Ian Fleming Crescent, Whitby
$999,999
4 Beds ⋅ 3 Baths ⋅ E13633880 MLS
Welcome to this exceptional two-storey home in the highly coveted Lynde Creek community of Whitby, where comfort, elegance, and location come together perfectly. From the moment you arrive, you'll be welcomed by a spacious foyer highlighted by a beautiful winding staircase that sets the tone for the rest of the home. Ideally situated directly across from a picturesque park with scenic walking trails, this home offers the perfect balance of nature and convenience. The bright eat-in kitchen is designed for everyday living and entertaining alike, featuring a walkout to a spacious deck overlooking the large, private backyard. With desirable southern exposure, the home is filled with an abundance of natural sunlight throughout the day, creating warm and inviting living spaces. The backyard is an ideal setting for summer barbecues, family gatherings, or simply relaxing outdoors. The thoughtfully designed main floor offers an abundance of living space, including a formal dining room, separate living room and a warm, inviting family room anchored by a cozy gas fireplace. Whether hosting quests or enjoying quiet evenings at home, there is room for every occasion. Upstairs, the expansive primary retreat is a true showstopper. This luxurious space features a private sitting area with vaulted ceilings and a second gas fireplace, creating the perfect sanctuary to unwind. The suite is completed by a generous walk-in closet and a spa-inspired 5-piece ensuite bathroom. Located in one of Whitby's most desirable family-friendly neighbourhoods, you'll enjoy convenient access to top-rated schools, parks ,trails, shopping, dining, and all essential amenities. Commuters will appreciate being located on a public transit route with easy access to the GO Station, making travel throughout the GTA effortless. This is a rare opportunity to own a beautiful home in an outstanding location-one that you'll be proud to call your own.

108 Mcquay Boulevard, Whitby
$799,900
4 Beds ⋅ 3 Baths ⋅ E13632450 MLS
Lovely updated 2-storey home situated on a premium extra-deep fenced lot with no neighbours behind, offering exceptional privacy and outdoor enjoyment in a sought-after family-friendly neighbourhood. This well-maintained home features an attached garage, excellent curb appeal, and a spacious functional layout ideal for growing families and entertaining alike.The beautifully renovated classic white kitchen showcases quartz countertops, ample cabinetry, modern finishes, and a walk-out to the party-sized deck complete with a gazebo-perfect for summer BBQs, relaxing evenings, or hosting family and friends. The kitchen flows seamlessly into the inviting family room, creating a bright open-concept space designed for comfortable everyday living. The main floor also offers a spacious open-concept living room and formal dining area filled with natural light, providing the perfect setting for gatherings and special occasions.Upstairs, the generous primary retreat features a renovated 3-piece ensuite and his and hers closets. Two additional spacious bedrooms and an updated 4-piece main bath complete the upper level. The lower level offers excellent additional space with a rec room, laundry area with sink, abundant storage, and a separate office, gaming room, guest room, or potential 4th bedroom-flexible space. Step outside and enjoy the peaceful private backyard with mature trees and no rear neighbours-an ideal space for kids, pets, gardening, or simply unwinding after a long day.Located in a highly desirable neighbourhood. Just minutes to transit, parks, baseball diamond, recreation centre, top-rated schools, shopping, restaurants, charming downtown Whitby, and major highways. Updates include main bath, fresh paint & ceilings 2026, MB flooring & cupboards & refaced deck 2025; Carpet & Railing on staircase 2025; Ensuite 2023; furnace (with warranty) & A/C, bay window & front & back door 2022; Kitchen 2020; A/C & roof 2019; double pane windows 2017; Move-in ready.

868 White Ash Drive, Whitby
$729,900
3 Beds ⋅ 3 Baths ⋅ E13631692 MLS
Discover 23 Woodward Drive, a lovingly cared-for home tucked into one of Whitby's most sought-after neighbourhoods. Here, pride of ownership is on full display-tree-lined streets, tidy lawns, and a friendly community feel make this an ideal place to call home. With shopping, schools, parks, walking trails, Durham Region Headquarters, and easy access to Hwy 401 and 407 all close by, convenience is truly at your doorstep. Inside, the home offers bright, spacious rooms with thoughtful layouts and plenty of storage. Each bedroom provides a comfortable, peaceful & spacious retreat. The backyard is a private haven featuring lush perennial gardens and serene outdoor space perfect for unwinding or hosting gatherings. Recent improvements, including a new roof (2025) and a newly paved driveway (2023), add to the home's long-term value and comfort. This is a wonderful opportunity to settle into a mature, established neighbourhood where everything you need is just minutes away. Some kitchen images have been virtually staged.

23 Woodward Drive, Whitby
$959,000
5 Beds ⋅ 3 Baths ⋅ E13622922 MLS
First Time On the market! A rare opportunity to acquire a lovingly maintained property from its original owners! This Sprawling Bungalow with 1,775 sf of main-floor living space is nestled in the highly sought-after Rolling Acres community of Whitby and is set on an expansive 49.74f wide by 118.11f deep lot and has exceptional curb appeal with plenty of setback and mature landscaping. The backyard offers an abundance of private outdoor space-ideal for entertaining on a large patio deck, gardening, or adding a future pool. Boasting 11.5 foot high ceilings in the grand living and dining room & 9 foot ceilings in the foyer and an expansive 1,100sf in-law suite (approx. estimate) with kitchen, 3 piece bathroom & 2 bedrooms in the professionally finished basement! Other Features include an attached 2 car garage with total 4 car parking spaces, new paint June 2026, new basement vinyl plank flooring (June 2026), new dishwasher (June 2026), a huge master bedroom with 3 piece ensuite bath and a turn-key handicap/wheelchair walk-way along the side & up to the rear deck of the property. This unique bungalow is designed for comfortable family living and easy main-floor accessibility and offers effortless versatile living for seniors or a growing family! Living in Rolling Acres places everyday essentials and lifestyle perks right at your doorstep: Top-Rated Schools including John Dryden P.S., Sir Samuel Steele P.S., and St. Mark the Evangelist Catholic School. Surrounded by family-friendly green spaces such as Darren Park, Jack Wilson Park, and connected walking/cycling trails along local creek systems. Shop & Dine Convenience minutes from major retail hubs along Taunton Road and Thickson Road, including local grocery stores, big-box shopping, coffee shops, and diverse dining options. Seamless Transit & Commuting with quick and convenient access to Highways 401, 407, and 412, as well as Durham Region Transit & the Whitby GO Station for a quick commute into Toronto.

51 Daines Drive, Whitby
$799,000
3 Beds ⋅ 3 Baths ⋅ E13622464 MLS
Beautiful and Extra large Corner Lot. Renovated 3 Bedrooms, 3 Bathrooms Home In FabulousWhitby Location. Perfect For First Time Buyers! Gorgeous Kitchen, Quartz Counters & Beautiful Backsplash! Flooring was done recently through out and updated with morden finishes! Massive Master W/His & Hers Closets & Semi-Ensuite! Generous Bedrooms W/Ample Storage! Across TheStreet From New Park, Steps To School, Shopping & all big box stores. Close To GO Transit & 401!

56 Winston Crescent, Whitby
$799,990
4 Beds ⋅ 4 Baths ⋅ E13611628 MLS
Attention First Time Home Buyer or Upgrade Families, here is 42 Fieldnest Crescent, Whitby for you, a 3+1-bedroom, 4-bathroom detached home in Whitby's sought-after Rolling Acres neighbourhood where every upgrade has already been done. Property has got fresh paint, new electrical fixtures, LED lighting, fully renovated bathrooms, new doors and door hardware throughout. All you bring is furniture and enjoy living in approximately 2,250 sq. ft of total living space, this home gives your family room to spread out - not just exist. A separate living room and family room let your household breathe - morning quiet in one room while life happens in the other. It's the kind of layout families grow into, not out of. Recent updates include A/C (approx 2 yrs), furnace (approx 3 yrs), windows and front door (approx. 10 yrs), and roof (approx. 12 yrs).The finished basement tells its own story. A self-contained space with its own bedroom, bathroom, kitchen, living area, and a private separate entrance - offering the potential to generate up to $1,500/month in potential basement rental income. That's up to $18,000 potentially a year toward your mortgage. Or it becomes the space where your parents live independently under the same roof. A rare flexibility most homes in Whitby, don't offer.Then there's the backyard - and you'll feel it the moment you step outside. Deep, open, private. Saturday barbecues with no time limit. Kids on real grass. Evenings that end with sky, not a neighbour's window. Outdoor space like this is getting harder to find. Out front, the extended driveway fits up to six vehicles alongside a single-car garage - because parking should never be a daily problem.Rolling Acres offers top-rated schools with French Immersion and IB programs, parks within walking distance, and shopping at Thickson and Taunton. Highway 407, Highway 412, and the Whitby GO Station keep you connected to Toronto while your family enjoys one of Whitby's safest communities.

42 Fieldnest Crescent, Whitby
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