Whitby Homes with 31-50 Approx Age

Whitby Homes with 31-50 Approx Age

Welcome to Whitby, Ontario, a charming town nestled along the shores of Lake Ontario, where history meets modern living. Known for its picturesque landscapes and vibrant community, Whitby offers a unique blend of small-town charm and urban convenience. With its rich heritage, friendly neighborhoods, and an abundance of parks and recreational activities, it's no wonder Whitby is a sought-after destination for families and professionals alike.

The town boasts a diverse real estate market, and if you're looking for homes with a bit of character, you'll find an array of properties that fall within the 31-50 year age range. These homes often embody the craftsmanship and unique architectural styles of their time, providing a warm and welcoming atmosphere. Many of these residences feature spacious layouts, mature trees, and established landscaping, creating a sense of tranquility and comfort.

Living in Whitby means enjoying easy access to a variety of amenities, including top-rated schools, shopping centers, and dining options. The town is also well-connected to public transit and major highways, making commuting to nearby cities like Toronto a breeze. Outdoor enthusiasts will appreciate the numerous parks, trails, and waterfront activities that Whitby has to offer, ensuring there’s always something to do.

Whether you're searching for a family home with a rich history or a cozy retreat with modern updates, Whitby’s diverse housing options will surely captivate your heart. Discover the charm of Whitby and find your perfect home in this delightful community today!

Newest Whitby Homes with 31-50 Approx Age

$1,029,000
3 Beds ⋅ 4 Baths ⋅ E13604926 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
6 Beds ⋅ 4 Baths ⋅ E13597710 MLS
Welcome to 1 Mayfield Crescent - an impeccably cared-for 5+1 bedroom, 4-bathroom corner-lot home in one of Whitby's most desirable family neighbourhoods. With 2,898 sq. ft. above grade plus 1,606 sq. ft. of finished basement space, this property offers exceptional room for growing families, multi-generational living, and effortless entertaining. The main floor features a beautifully remodelled kitchen (2014) with granite countertops, marble flooring, upgraded cabinetry, and a pantry, opening to a warm family room with hardwood flooring (2014) and a gas fireplace. A main-floor bedroom or office adds flexibility, while the convenient laundry room includes a separate side entrance - offering easy potential to convert the lower level into a private in-law suite. The charming screened-in front porch, with east-facing morning light and an additional north-facing entry, provides a peaceful retreat for coffee or evening relaxation. The fully finished basement enhances the home's versatility with a complete second kitchen, ideal for extended family or additional living space. Combined with the side entrance, the layout is well-suited for an in-law suite conversion. Meticulously maintained and upgraded: wood shutters (2013), roof (2017), LED pot lights (2021), furnace (2022), heat pump (2024), leased tankless hot water heater (2024), and refreshed landscaping (2025). A double-car garage with interior access adds everyday convenience. Located close to top-rated schools, parks, shopping, restaurants, and major amenities, this exceptional home offers the perfect blend of space, comfort, and location. Refer to the feature sheet for the full list of upgrades - the enhancements are extensive.

1 Mayfield Crescent, Whitby
$739,900
3 Beds ⋅ 3 Baths ⋅ E13596820 MLS
Welcome to 23 Woodward Drive, a beautifully maintained home nestled in one of Whitby's most desirable, family-friendly neighbourhoods. This area shows true pride of ownership, with manicured lawns, mature trees, and a warm community feel. Perfectly situated close to shopping, schools, parks, scenic walking trails, Durham Region Headquarters, and offering quick access to both Hwy 401 and 407, this location delivers exceptional convenience for commuters and families alike. Inside, you'll find spacious, well-designed rooms with plenty of natural light and an abundance of storage throughout. The generous bedrooms provide comfortable retreats for every member of the household. The backyard is a private oasis featuring lush perennial gardens and tranquil outdoor space ideal for relaxing, entertaining, or enjoying nature right at home. Recent updates include a new roof (2025) and a freshly paved driveway (2023), offering peace of mind for years to come. This home has been lovingly cared for and is ready for its next chapter. A fantastic opportunity to move into a mature, established neighbourhood with everything you need just moments away. Note that some pictures of the kitchen are virtually staged.

23 Woodward Drive, Whitby
$939,000
4 Beds ⋅ 4 Baths ⋅ E13587214 MLS
Welcome to this beautifully maintained detached 2-storey home, offering the perfect blend of comfort, functionality, and outdoor living. Complete with an attached double garage and in the highly sought-after Pringle Creek area of Whitby, this property has been lovingly cared for and is ready for its next family to call it home. Step inside to a spacious and welcoming main floor featuring a bright living and dining room combination, ideal for entertaining or family gatherings. A separate family room provides the perfect place to relax, complete with a charming brick wood-burning fireplace and a walk-out to the backyard patio. The expanded eat-in kitchen is truly the heart of the home, boasting custom cabinetry, sleek black appliances including a gas stove, a large picture window overlooking the beautifully landscaped backyard, a breakfast bar, and a convenient moveable centre island with locking wheels. A second walk-out leads directly to the backyard, making outdoor dining and entertaining effortless. Upstairs, you'll find four cozy bedrooms, including a spacious primary retreat featuring a walk-in closet and a private 4-piece ensuite. An additional 3-piece bathroom with a walk-in shower serves the remaining bedrooms, while broadloom carpeting throughout the upper level adds warmth and comfort. The backyard features an inviting and professionally maintained in-ground pool with a maximum depth of approximately 5.5 feet, expansive patio space, and beautifully maintained gardens that create a peaceful outdoor oasis. The front yard offers equally impressive landscaping, providing exceptional curb appeal. The full, unspoiled basement offers endless possibilities with bathroom rough-ins already in place, making it easy to create the additional living space you've always envisioned. Whether you're looking for room to grow, space to entertain, easy access to major highways or a backyard retreat to enjoy all summer long, this exceptional home delivers it all.

38 Trinity Crescent, Whitby
$619,000
3 Beds ⋅ 2 Baths ⋅ E13586932 MLS
Welcome to the perfect blend of style, comfort, and convenience in the highly sought-after Bradley Estate community. This beautifully renovated 3-bedroom, 2-bathroom home is move-in ready. Extensive renovations completed between 2021 and 2026 showcase quality craftsmanship and timeless design. Rich engineered hardwood flooring flows throughout, complemented by bright, inviting living spaces and beautifully redesigned bathrooms with herringbone tile floors on both the main and 2nd floors. At the heart of the home is a stunning kitchen featuring elegant quartz countertops, stainless steel appliances, and sophisticated finishes that make cooking a pleasure. The rear garden features a walkout to a 96 sq ft paved patio from the dining room, and privacy fences on 3 sides (open to yards on either side). A covered 55 sq ft front porch, 213 sq ft single-car garage, private driveway, and abundant visitor parking provide everyday convenience for both homeowners and guests. The partially finished basement has a deep 8 ft ceiling height at the rear making this a blank canvas you'll be eager to personalize! Whether you're a first-time buyer, a growing family, or looking to downsize without sacrificing space or style, this home offers the perfect balance of comfort and low-maintenance living. Maintenance fees include water, and groundskeeping, giving you more time to enjoy the things you love. Plus, this pet-friendly community welcomes pets in accordance with Whitby by-laws, making it a wonderful place for every member of the family! Ideally located just minutes from shopping, restaurants, grocery stores, parks, excellent schools, and the Whitby Civic Recreation Complex. You'll also enjoy effortless access to Highways 401, 407, and 412-making commuting across the GTA a breeze. Beautifully updated, thoughtfully designed, and perfectly located, this is a home you'll be proud to call your own.

10 Bassett Boulevard Unit 25, Whitby
$709,999
3 Beds ⋅ 2 Baths ⋅ E13576880 MLS
Welcome to 103 Guthrie Crescent, Whitby! This beautifully maintained 3 bedroom, 2-bathrooms semi-detached home offers approximately 1,138 sq. ft. above grade and a functional layout designed for comfortable family living. The home features an upgraded kitchen, renovated washrooms, and bright, sun-filled living spaces that create a warm and inviting atmosphere throughout. The finished walk-out basement adds valuable living space makes it ideal for extended family, guests, a home office, or recreation area. Outside, enjoy a fully fenced backyard, perfect for children and outdoor entertaining. Just steps to Col. J.E. Farewell Public School, this home offers exceptional convenience for growing families. Enjoy easy access to major highways including Highway 401, Highway 407, and Highway 412, as well as Thermea Spa Village Whitby and the GO Transit network for effortless commuting. Combining thoughtful updates, functional living space, and an unbeatable location, 103 Guthrie Crescent is a fantastic place to call "YOUR HOME".

103 Guthrie Crescent, Whitby
$1,199,900
5 Beds ⋅ 3 Baths ⋅ E13576380 MLS
Beautifully updated all-brick 2-storey home in a highly sought-after family neighbourhood! Finished from top to bottom, this spacious home offers an impressive vaulted 2-storey foyer and a functional open-concept main floor with hardwood flooring throughout principal rooms. Renovated kitchen features quartz countertops, porcelain flooring, ceramic backsplash, stainless steel appliances, and a bright breakfast area with walkout to a party-sized deck, patio, and fully fenced backyard. Cozy family room with hardwood floors and gas fireplace overlooks the kitchen, while the separate formal dining room with bay window and sunken living room provide excellent entertaining space. Renovated main floor powder room, mudroom, and interior garage access add everyday convenience. The elegant spiral staircase leads to a spacious primary suite with walk-in closet and 5-piece ensuite featuring a whirlpool tub, separate shower, and double vanity. Three additional generous bedrooms share an updated 4-piece bath. Professionally finished basement includes a bright recreation room with oversized windows, gas fireplace and laminate flooring, a versatile flex room or 5th bedroom with pot lights, large laundry room with sink, drying racks and ironing area, plus a workshop with built-in shelving and workbench. Beautifully landscaped with interlocking stone walkways, patio, mature gardens, and in-ground sprinkler system. Close to top-rated schools, parks, shopping, transit and all amenities. Move-in ready and perfect for growing families!

1 Glencedar Crescent, Whitby
$999,999
4 Beds ⋅ 4 Baths ⋅ E13566662 MLS
Welcome to this beautifully maintained 4-bedroom, 4-bathroom detached home in the highly sought-after Pringle Creek community of Whitby, proudly offered for sale by its original owners. Showcasing true pride of ownership throughout, this exceptional home has been lovingly cared for and thoughtfully maintained. Designed for comfortable family living, the main floor features elegant formal living and dining rooms, a spacious kitchen with a convenient pocket door, a separate family room with a cozy wood-burning fireplace, and an extended laundry room offering both side door access and direct entry to the garage. Step outside to your own private backyard oasis, complete with a large deck, gas BBQ hookup, and a stunning inground swimming pool-perfect for relaxing or entertaining family and friends all summer long. Upstairs, you'll find four generously sized bedrooms, including a spacious primary retreat featuring a walk-in closet and a beautifully renovated ensuite. Additional highlights include engineered hardwood flooring throughout the main and upper levels, garage attic storage for added convenience, and a cold storage room, providing practical solutions for all your storage needs. The finished basement offers even more versatile living space with a large recreation area, a 2-piece bathroom, a dedicated office nook, an expansive workshop ideal for hobbies, storage, or future customization, and a convenient cold storage room. Outside, the beautifully landscaped front yard is enhanced with an in-ground sprinkler system, making lawn maintenance effortless while maintaining exceptional curb appeal. Ideally located close to excellent schools, parks, recreation facilities, the public library, and premium shopping, this exceptional home offers the perfect blend of space, comfort, functionality, and convenience in one of Whitby's most established and family-friendly neighbourhoods.

12 Jason Drive, Whitby
$569,000
3 Beds ⋅ 2 Baths ⋅ E13552382 MLS
Welcome to this well-maintained 3-bedroom end-unit townhouse like a semi, in a desirable Whitby neighbourhood-perfect for first-time buyers or people downsizing. This bright and functional home offers a spacious functional layout . The main floor features a comfortable living and dining area ideal for everyday living and entertaining. The home also includes a fully finished basement, providing additional living space that can be used as a family room, recreation area, or home office. Step outside to a private backyard backing onto a park, offering a peaceful setting with no rear neighbours and direct access to green space. Conveniently located close to schools, parks, shopping, transit, and major amenities. A fantastic opportunity to own a great starter home in a family-friendly community.

927 Burns Street W Unit 29, Whitby
$1,250,000
4 Beds ⋅ 4 Baths ⋅ E13544494 MLS
Must see rare 5 level backsplit with Pringle Creek ravine at the back and side. Updated kitchen with quartz counters, abundant cupboards and built-in desk, under counter lighting and walk out to the side yard. Master has a 3 pc updated ensuite with walk in shower and a walk in closet. 2 more bedrooms and a 4 pc main bath complete the top floor. Open living dining room features floor to ceiling bay window over looking the ravine and large picture window facing the street. Fabulous in-law suite all above ground with a walk out to a gardener's and nature lovers paradise with large covered deck, inground pool (totally redone in 2024) and those incredible ravine vistas. There is also a large recroom that has a 2 pc bath and both a large cold room and workshop with a walk out to the side yard. Shed has hydro, water and houses the pool equipment In addition to all this there is a sub-basement with wine cellar and 3 more rooms for storage or whatever. 3 schools in very short walking distance. You have all the amenities of a great town like Whitby but you'll think you are up in Muskoka. Come see. You'll want to stay. We have ....for 30 years. Yes the realtor is also the seller and his wife.

150 Pringle Drive, Whitby
$379,999
2 Beds ⋅ 1 Baths ⋅ E13541042 MLS
Perfect for first-time buyers, down-sizers, or investors! Enjoy the stunning east facing views from the quiet and peaceful 10th floor. Natural sunlight floods this beautiful open concept layout. Kitchen overlooks the living and dining area, with beautiful glass backsplash. Just off the living room, you will find a second room which is suitable for an office, second bedroom, or a cozy reading nook. This unit includes an owned locker and underground parking space. This prime location offers access to all your wants and needs! Amenities include grocery, drugstore, dining/restaurants, banking, recreation centre, library, parks, public transit and more!

711 Rossland Road E Unit 1002, Whitby
$924,900
3 Beds ⋅ 3 Baths ⋅ E13534102 MLS
22 Ladies College Drive is a showpiece of timeless elegance, nestled beneath a canopy of mature trees in one of Downtown Whitby's most prestigious and sought-after neighbourhoods. From the moment you arrive, the exceptional curb appeal and meticulously landscaped grounds set the stage for what awaits inside. Beautifully finished from top to bottom, this impressive 3-bedroom home (easily converted back to 4 bedrooms) showcases quality craftsmanship and thoughtful upgrades throughout. The heart of the home is the stunning gourmet kitchen, featuring quartz countertops, a centre island with breakfast bar, custom cabinetry with built-in pantry, and an open-concept design that flows effortlessly into the spacious dining area-perfect for everyday living and entertaining. The inviting living room with gleaming hardwood floors offers an elegant space to gather, while the cozy family room with gas fireplace and garden door walk-out leads to your own private backyard retreat. Designed to impress, the award-worthy landscaping surrounds a heated inground pool with a brand-new liner and brand new rubberized pool decking (2026), newly resurfaced deck boards (2026), louvered pergola (2026), and multiple areas to relax, entertain, and enjoy summer days in complete privacy. The primary suite offers a walk-in closet and beautifully appointed 3-piece ensuite, creating the perfect place to unwind. The professionally finished lower level extends the living space with a generous recreation room featuring a stylish wet bar with built-in cabinetry, dedicated games area, recessed illuminated poster displays, built-in desk ideal for working from home, and abundant storage. Ideally located just minutes from Trafalgar Castle School, parks, walking trails, the charming boutiques and restaurants of vibrant Downtown Whitby, Highway 401, and the Whitby GO Station, this exceptional home perfectly combines luxury, comfort, and convenience.

22 Ladies College Drive, Whitby
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