Whitby Homes with 31-50 Approx Age

Whitby Homes with 31-50 Approx Age

Welcome to Whitby, Ontario – a charming town that perfectly balances vibrant urban living with the serene beauty of nature. Nestled in Durham Region, Whitby boasts a rich history, a thriving community, and an enviable location along the shores of Lake Ontario. With its picturesque waterfront, lush parks, and well-maintained trails, Whitby is a haven for outdoor enthusiasts and families alike.

As you explore Whitby, you’ll find a delightful mix of residential neighborhoods, each with its own unique character. For those seeking homes with a bit of history, the area offers a variety of properties that fall within the 31-50 year age range. These homes often feature classic architectural designs, spacious layouts, and mature landscaping that adds to their charm. Many of these residences have been lovingly updated, blending modern amenities with the timeless appeal of their original construction.

Whitby is not just about beautiful homes; it’s also about community. With excellent schools, vibrant shopping districts, and a plethora of recreational activities, this town is perfect for families, young professionals, and retirees. The downtown area is bustling with restaurants, boutiques, and cultural attractions, while the nearby waterfront provides a tranquil escape for leisurely strolls or picnics by the lake.

Whether you’re looking to buy your first home, upgrade to a larger space, or invest in a property with historical significance, Whitby has something for everyone. Discover the warmth and charm of this remarkable town, where community spirit and natural beauty come together to create an inviting place to call home.

Newest Whitby Homes with 31-50 Approx Age

7 Houghton Court, Whitby
$999,000
5 Beds ⋅ 4 Baths ⋅ E14142950 MLS
Opportunity knocks! This beautiful, modern, multi-generational home on a quiet dead-end street offers peace, privacy, and exceptional value. Step into a bright, spacious open-concept layout made for everyday living and entertaining. The stunning kitchen features sleek modern cabinetry, stainless steel appliances, and a large island, the heart of the home for family gatherings and dinner parties. The family room has a charming fireplace and a walkout to the private backyard oasis, ideal for summer barbecues, gardening, or quiet evenings. The expansive primary bedroom includes a luxurious 4-piece ensuite. Even better, the 2-bedroom in-law suite offers incredible opportunity for multi-generational living. Ash Creek Park is just steps away. This is the perfect blend of style, comfort, and functionality in a family-friendly setting.

7 Houghton Court, Whitby
29 Bellwood Drive, Whitby
$989,000
5 Beds ⋅ 4 Baths ⋅ E14142616 MLS
Located in established Blue Grass Meadows, this well-maintained 4+1 bedroom home offers plenty of space for the whole family. The renovated kitchen (2017) features quartz countertops, ample storage and a breakfast bar island. Four spacious bedrooms upstairs include a primary bedroom with ensuite and walk-in closet. The finished basement offers a large recreation room, additional bedroom or office and 3-piece bathroom.The fully fenced backyard features a two-tiered deck, multiple seating areas and four oversized raised garden planters. A custom-built shed with electricity, cable, and telephone service, plus its own deck and seating area, offers great space for hobbies or a workshop.Additional updates include furnace (2025), two bedroom windows (2026), roof shingles (2018), hot water tank (2019), A/C (2017) and gas fireplace conversion (2017).

29 Bellwood Drive, Whitby
509 Dunlop Street W, Whitby
$599,900
2 Beds ⋅ 1 Baths ⋅ E14140384 MLS
Welcome to this immaculate, beautifully updated all-brick bungalow nestled in the highly sought-after Old Whitby community! This stunning home showcases gorgeous new plank laminate flooring, modern pot lighting, fresh neutral paint, and a bright, inviting open-concept living and dining area overlooking the front gardens. The spacious kitchen features stainless steel appliances and a sliding glass walkout to an expansive entertainer's deck, complete with a charming pergola, mature trees, and exceptional privacy-perfect for relaxing or hosting family and friends! Generously sized bedrooms offer ample closet space and large windows that fill the home with natural light. A beautifully renovated main bathroom adds to the home's appeal. The unspoiled basement features above-grade windows, laundry area, abundant storage, and endless possibilities to create additional living space. Ideally situated just steps from schools, parks, and the charming shops and restaurants of Downtown Whitby, with quick access to Highway 401 and the GO Train for an effortless commute. A rare opportunity to enjoy stylish, move-in-ready bungalow living in one of Whitby's most desirable neighbourhoods!

509 Dunlop Street W, Whitby
61 Forest Hts Street, Whitby
$889,900
4 Beds ⋅ 4 Baths ⋅ E14138404 MLS
Welcome to this beautifully designed Tribute-built home in Pringle Creek, a mature, family-friendly community. With nearly 2,500 square feet of thoughtfully planned living space, this home offers 4 generous bedrooms and 4 bathrooms.A grand foyer with a sweeping spiral staircase sets the tone, leading to a formal living room, a separate dining room, and a cozy family room with a wood-burning fireplace. Hardwood and ceramic flooring run throughout the main level, adding warmth and easy maintenance. The spacious kitchen features a large pantry, stainless steel appliances, and a bright breakfast area with a walkout to a two-tiered deck, ideal for barbecues, morning coffee, and outdoor entertaining. Finally, rounding out this level is a spacious laundry room with a convenient side entrance and a 2-piece powder room. Upstairs, the primary suite offers a walk-in closet and a 4-piece ensuite with a soaker tub and separate shower. Three additional spacious bedrooms and a full 4-piece main bath complete the second level.The partially finished basement includes a 2-piece bath, a recreation room, and a gym area, with an unfinished space ready for your personal vision. Outside, the fully fenced, private backyard features a large storage shed.Location is a major bonus: Whitby GO Station is just 10 minutes away, and shopping, recreation centres, parks, schools, and everyday amenities are only a 2-minute drive.

61 Forest Hts Street, Whitby
52 Longfellow Court, Whitby
$849,000
4 Beds ⋅ 3 Baths ⋅ E14138274 MLS
Welcome to 52 Longfellow Court, Whitby! Discover the perfect blend of space, comfort, and functionality in this beautifully appointed 4-bedroom, 3-bathroom home. Thoughtfully designed for everyday living and effortless entertaining, this inviting property features an open-concept main living area adorned with engineered hardwood flooring stretching seamlessly across the living, dining, and family rooms. The main floor flows naturally to a walkout with a spacious deck overlooking a massive, private backyard with no neighbours behind-your own peaceful outdoor retreat. The cozy family room, complete with a gas fireplace creates the perfect setting for relaxing evenings. For added everyday convenience, the main floor also offers a 2-piece powder room and laundry room with a separate side entrance. Classic crown moulding throughout adds a touch of timeless elegance, while updated bathrooms beautifully enhance the home's appeal. The possibilities continue downstairs with a large, unfinished basement, offering a blank canvas to create the additional living space you've always wanted. Imagine a recreation room, home gym, games room, or an ideal footprint for an in-law suite-the choice is yours! Ideally situated close to schools, highway 401 & 407, parks, and everyday amenities, this wonderful home offers the space, privacy, and versatility today's families are looking for, all within the welcoming Whitby neighbourhood of Pringle Creek. A wonderful place to put down roots, make lasting memories, and call home! *Roof 2019, Staircase refinished 2017, All Windows & Doors have been replaced over the years by homeowner, Furnace and A/C 2005- Well maintained by homeowner who is a Certified Gas and Refrigeration Mechanic. (All photos are from when home was vacant)

52 Longfellow Court, Whitby
137 Old Colony Drive, Whitby
$1,149,000
5 Beds ⋅ 4 Baths ⋅ E14138240 MLS
Welcome to 137 Old Colony Drive, an impressive executive home nestled in the highly desirable Pringle Creek community of Whitby! Offering 5 spacious bedrooms, 4 bathrooms and over 3,000 sq. ft. of above grade living space, this exceptional home provides the perfect blend of comfort, space and functionality for a growing or multigenerational family.The thoughtfully designed main floor features generous principal rooms, including a formal living and dining room, a spacious family room, a dedicated home office and a bright kitchen with a breakfast area, creating the perfect setting for both everyday living and entertaining. A convenient main-floor laundry room adds to the home's practical layout.Upstairs, discover five generously sized bedrooms, including an expansive primary retreat complete with walk-in closets and a private ensuite, offering a peaceful escape at the end of the day.The expansive unfinished basement presents an incredible opportunity to create a space tailored to your lifestyle. Whether you envision a home theatre, recreation room, fitness studio or additional living space, the possibilities are endless!Situated in an established, family friendly neighbourhood close to parks, schools, shopping, recreation and everyday amenities, this wonderful home offers the space and flexibility to grow with your family.An exceptional opportunity to make this impressive executive home your own!

137 Old Colony Drive, Whitby
50 Lumsden Crescent, Whitby
$1,199,900
6 Beds ⋅ 4 Baths ⋅ E14137612 MLS
Pringle Creek, Whitby at its finest! This immaculate, move-in ready 2,286 sq ft home on a quiet street pairs a private backyard oasis with a showstopper kitchen and major upgrades done. New sliding doors open to an entertainer's deck with outdoor kitchen, gas BBQ area and pergola, overlooking an inground pool (new cover 2026). The open-concept kitchen features heated floors, an 8-ft island with sink and dishwasher, quartz counters and pantry, flowing into the family room. Crown moulding and pot lights on the main floor; French doors lead from the paneled living room to a formal dining room with built-in buffet. The primary retreat offers a walk-in closet, second closet and ensuite with heated floors. Finished basement with two large rooms, luxury vinyl flooring, 3-pc bath and kitchen, ideal for multi-generational living. Insulated, heated, EV-ready double garage. Energy-efficient upgrades: net-metered solar panels (2024, transferable warranty), 200-amp panel, new gas lines (2025), roof (2022), smart lighting and remodeled powder room. True indoor-outdoor living, turnkey and ready for you. Ask your Realtor for the upgrade list and solar details.

50 Lumsden Crescent, Whitby
42 Old Colony Drive, Whitby
$729,900
4 Beds ⋅ 3 Baths ⋅ E14133688 MLS
Welcome to this beautifully renovated, all-brick, 2-storey family home nestled in the highly sought-after Pringle Creek community of North Whitby! Offering 3+1 spacious bedrooms, 3 bathrooms, and a fully finished basement, this move-in-ready gem is perfect for growing families! Impressive curb appeal begins with an inviting interlocking walkway leading to a welcoming entry. Step inside to a bright, open-concept living and dining area featuring large windows that fill the space with natural light, complemented by fresh neutral paint and stylish décor throughout. The updated kitchen is sure to impress with quartz countertops, custom backsplash, plank-style ceramic flooring, abundant cabinetry and counter space, pantry, stainless steel appliances, and a sliding glass walkout to a beautiful interlocking patio and fully fenced backyard complete with a large garden shed. Upstairs, discover 3 generously sized bedrooms, all offering excellent closet space, including a spacious primary retreat with his-and-hers closets and peaceful backyard views. Need more room? The fully finished basement offers incredible versatility with brand-new vinyl flooring, a 4th bedroom featuring its own 4-piece ensuite, a convenient laundry area, and ample storage. Ideally located just steps from sought-after public and Catholic schools, parks, transit, shopping, and all major amenities. **A fantastic opportunity to own a beautifully updated family home in one of North Whitby's most desirable neighbourhoods!**

42 Old Colony Drive, Whitby
5 Heaver Drive, Whitby
$759,900
5 Beds ⋅ 3 Baths ⋅ E14130918 MLS
This home offers a fabulous layout with plenty of flexibility for family living. Located in the Pringle Creek neighbourhood. The main level features an eat-in kitchen, living and dining rooms with laminate flooring, and main floor laundry. Upstairs, the staircase splits to two separate areas, with a family room featuring a cozy fireplace (currently used as the 4th bedroom) on one side and three additional bedrooms on the other. The spacious primary bedroom includes a walk-in closet and ensuite bath. The finished basement offers even more living space with a recreation room or den and an additional bedroom. Freshly professionally painted throughout, with furnace and A/C updated in 2024, a one-car garage, room for 5-car parking and tons of storage space. Enjoy the fenced backyard with deck and a separate fenced dog run. Conveniently located steps to shopping and plaza, with easy access to Hwy 401. A great opportunity for families looking for space, flexibility and convenience!

5 Heaver Drive, Whitby
360 Watson Street W Unit 105, Whitby
$749,500
3 Beds ⋅ 2 Baths ⋅ E14101496 MLS
Welcome to The Sailwinds at Port Whitby. This quiet waterfront community with easy access to the 401 and 407 offers something for everyone. The Sports complex and Abilities centre are steps away as are many fine shopping and dining options. Located on the lakefront trail, its your home and getaway all in one. The Whitby GO is a 5 minute walk for easy access to the city. The stunning 1586 sqft condo overlooks a stand of fur trees and private sunken garden, to the west the Victoria fields and stunning sunsets. This suite offers unusual privacy reminiscent of a country home. Inside the bright, spacious 3-bedroom, 2-bath home has expansive windows, upgraded kitchen, hardwood floors and an open-concept living/dining area for entertaining and family gatherings. Freshly painted with stunning decor. Unique to condo life these days the amenities are outstanding with two gyms, a large indoor pool with hot tub and sauna and large entertaining area for social gatherings galore. Also included are two parking spaces. Truly a rare find.

360 Watson Street W Unit 105, Whitby
360 Watson Street W Unit 308, Whitby
$529,900
1 Beds ⋅ 2 Baths ⋅ E14098694 MLS
Lakeside Living with Resort Style Amenities! Welcome to Suite 308 at 360 Watson Street West in Whitby. This spacious 1 bedroom, 2 bathroom condo offers approximately 941 sq ft, providing comfortable living space in a highly convenient Port Whitby location.Freshly painted throughout with new light fixtures, the suite features in suite laundry, a lovely balcony and a functional layout with plenty of space to live and entertain. Residents also enjoy a fantastic selection of building amenities, including an indoor swimming pool, gym, sauna, recreation and party room, landscaped courtyard, and on site property manager.Located within walking distance of the waterfront, restaurants, shopping, the Abilities Centre, and Whitby GO Station, with parks, trails, Port Whitby Marina, and major commuter routes nearby. A great opportunity for first time buyers, downsizers, or commuters looking for low maintenance living close to the lake and GO.

360 Watson Street W Unit 308, Whitby
74 Henderson Drive, Whitby
$1,228,888
5 Beds ⋅ 4 Baths ⋅ E14098348 MLS
Welcome to an exceptional ravine-facing residence in one of Pringle Creek's most desirable mature neighbourhoods. Set on an extraordinary 49.21 x 230 ft lot, this meticulously maintained home offers just under 3,000 sq ft of finished living space, timeless curb appeal, and a rare connection to nature in the heart of Whitby. Wake up to deer, rabbits, birds and abundant wildlife as you enjoy morning coffee in the four season solarium. Floor to ceiling windows frame 230 ft of ravine views, mature trees, and peaceful green space. A meditation garden, waterfall, hammock, patio, and multiple seating areas create private cottage living in the city, with endless potential for your dream outdoor retreat. A spacious two storey foyer opens to a bright, functional layout with hardwood flooring on the main floor and greenery visible from nearly every window. The formal living room is complemented by a separate family room with a rustic gas fireplace. The renovated kitchen offers quartz countertops, stainless steel appliances, abundant storage, a large island with seating, and an open flow to the dining room, eat in kitchen area, and solarium. Main floor laundry and a powder room complete the main. Upstairs, the generous primary bedroom includes a walk-in closet plus an adjoining room ideal as a dressing room, study, nursery, or additional closet. The renovated 5pc ensuite features a double vanity, jacuzzi tub, and glass enclosed tiled shower. Three additional bedrooms offer excellent family and guest space.The finished basement adds a large recreation room, games area, wet bar, gym, additional bedroom, and jacuzzi bathroom perfect for relaxing, fitness, movie nights, or working from home. Enjoy direct access to an extensive trail system, with nearby parks, green space, schools, shopping, recreation, and everyday conveniences. 74 Henderson Drive offers a fantastic ravine lot, space, setting, and family lifestyle that are increasingly difficult to find in established Whitby.

74 Henderson Drive, Whitby
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