Pickering Homes with 51-99 Approx Age

Pickering Homes with 51-99 Approx Age

Welcome to Pickering, Ontario—a vibrant regional municipality that beautifully balances urban convenience with natural beauty. Nestled along the shores of Lake Ontario, Pickering boasts a rich tapestry of parks, trails, and waterfront activities, making it an ideal place for families, nature enthusiasts, and professionals alike.

Pickering is renowned for its diverse communities and thriving economy, with easy access to major highways and public transit, including GO Transit, ensuring seamless connectivity to downtown Toronto and beyond. The city is home to a variety of shopping, dining, and entertainment options, from the bustling Pickering Town Centre to charming local boutiques and eateries that reflect the area's multicultural spirit.

For those seeking homes with character, Pickering offers an impressive selection of properties built between 51 to 99 years ago. These homes exude charm and history, often featuring unique architectural styles that tell a story of the region's past. Many of these residences have been lovingly maintained or tastefully updated, providing modern amenities while retaining their classic appeal. Whether you’re drawn to cozy bungalows or spacious two-storey homes, the options available in this age range cater to various lifestyles and preferences.

Living in Pickering means embracing a community that values both heritage and progress. With excellent schools, abundant recreational facilities, and a commitment to sustainable living, it’s no wonder that residents take pride in calling this city home. Explore the possibilities of finding your dream home in Pickering, where history and modern living harmoniously coexist.

Newest Pickering Homes with 51-99 Approx Age

925 Bayly Street Unit 17, Pickering
$579,950
4 Beds ⋅ 2 Baths ⋅ E14113424 MLS
Absolute Show Stopper!! ** Location Location ** - Fabulous Westshore Community, END UNIT, Walking Distance To The Lake & Pickering Beach!! GO Train, Quick access to 401, Restaurants & Shops At Pickering City Centre, Spacious kitchen with custom Backsplash overlooking Dining Room Perfect For Entertaining. Oak Staircase Leads To The 2nd Floor With 4 Spacious Bedrooms, Primary and second bdrm Offer Walk In Closets. Walk-out access to the deck from the living area enhances indoor-outdoor enjoyment. Perfect for Summer BBQ's with family and friends. Bright, spacious, and private unit, this home delivers flexibility, comfort, and exceptional value in a prime Pickering location. Includes: water, building insurance, 1 parking, Schools & Parks Steps away - Don't miss out!

925 Bayly Street Unit 17, Pickering
971 Oklahoma Drive, Pickering
$889,000
3 Beds ⋅ 3 Baths ⋅ E14103242 MLS
Steps to the Beach! Beautiful Detached Backsplit Large Lot Size 50 x 100 Ft! Amazing location around the corner from Frenchman's Bay Yacht Club! 3 Bedroom, 3 Bathroom. Great Layout with a Spacious Living Room Combined with Dining. Super Functional Kitchen with Lots of Cabinets and Counter Space. Family Room Located on Lower Level. Freshly Fully Painted Walls, Ceilings and Baseboards! Enjoy your Summers in the Beautiful Backyard Surrounded by Gardens and a Deck for Outdoor Entertaining. Spacious Solarium for cozy nights! Fully Fenced Backyard. Private Wide Driveway That Can Fit Up to 4 Cars. Join the Very Popular West Shore Community and Enjoy Frenchman's Bay, Waterfront Trail and Beach Point Promenade! 5 Minutes to 401 via Whites Rd S, Catholic and Public Schools, Pickering City Centre, Shops, Casino, Restaurants, Pickering Go Station and More!

971 Oklahoma Drive, Pickering
508 Cliffview Road, Pickering
$1,250,000
4 Beds ⋅ 3 Baths ⋅ E14098358 MLS
Welcome to this custom home with a one of a kind stunning layout with vaulted ceilings, large picture windows & plenty of space in generously sized rooms. The lot size is among the largest in the area, featuring a very large front & backyard. Use the room inside the front door as a mud room, dining room or a home office, whichever suits your needs. A small 3 pc bathroom on the main level. The livingroom has a large gas fireplace with a beautiful brick surround & the open sight line from the huge front window to the patio in the backyard which is a private woodland retreat in the city with natural landscaping & is fully fenced. There is a side door that exits onto a covered patio at the side of the house.The stairway to the bedrooms features a beautiful blackwrought iron railing & the upper hallway overlooks the open livingroom area. From the livingroom you step down into the huge family room with a w/out to the backyard. The large kitchen has white quartz countertops & plenty of cupboards. Upstairs are three generously sized bedrooms each with large windows to let in lots of natural light. The basement is suitable for an in-law suite with a multipurpose room, bedroom & 3 pc spa sized bathroom with marble tiled floors for multigenerational or multi family living. More storage space can be found in a very large laundry room. This property has lots of parking with its long single wide driveway & no sidewalk so there is space for multiple vehicles which could be expanded if needed with space the huge front yard offers. You are steps away from a park & the lake which is visible from the street & the park. The area is ideal for long walks, & time spent outdoors. This lot has ample space for your additions, ideal for investors & developers. There is deeded access to the waterfront trail that remains in effect if the home is renovated but not demolished. Book your visit today. Remember if you love it, you better put an offer on it.

508 Cliffview Road, Pickering
862 Boxworth Place, Pickering
$1,297,600
4 Beds ⋅ 4 Baths ⋅ E14031786 MLS
*Welcome to 862 Boxworth Pl in the desirable West Shore neighborhood of South Pickering. *Situated on a quiet cul-de-sac, this home is essentially a new house - modern, pristine, and updated with exceptional quality and care throughout. *The open layout is designed for functional living and daily comfort. *The bright kitchen features quartz countertops, a gas stove, a large center island, and plenty of cabinet storage, making it the focal point of the home. *It connects smoothly to the living and dining rooms, as well as the breakfast area and family room. *Three walkouts along the back bring in an abundance of natural light. Inside, comprehensive upgrades include new wiring (200-amp panel), plumbing, windows, roof, exterior siding, and fresh paint. *Key mechanicals and features include a newer furnace, a tankless water heater, smart-wired interior/exterior lights, pot lights, built-in shelving, an alarm system, and two basement crawlspaces for extra storage. *A professionally installed radon mitigation system is also included for added peace of mind. *The upper floor offers four spacious bedrooms, highlighted by an impressive primary suite with vaulted ceilings, a sitting area, his-and-hers closets, and an ensuite bath. *The fully finished basement adds a versatile great room and a 3-piece bathroom with a glass shower. *Outdoors, the property features an impressive pie-shaped lot with 150 feet along the backyard, mature trees, open side-yard space, a patio, and a large deck-providing a private setting for family gatherings and entertaining. *Enjoy a prime location steps from Lake Ontario, Frenchman's Bay, waterfront trails, parks, top schools, and quick access to the GO station and Highway 401 *Move-in ready-just unpack and feel right at home!

862 Boxworth Place, Pickering
1210 Radom Street Unit 208, Pickering
$439,900
3 Beds ⋅ 1 Baths ⋅ E13872864 MLS ⋅ The Bayshore Condominums BLDG.
Welcome to The Bayshore. Downsize your responsibilities not your lifestyle! Carefree living in the heart of Pickering, just minutes from Frenchman's Bay! This bright and spacious 3-bedroom condo with 2 private Balconies to enjoy, offers the perfect opportunity to downsize without giving up the space, comfort, and lifestyle you love. With sunny south exposure, an open and functional layout, and no carpet throughout, this beautifully maintained suite is truly move-in ready.Enjoy over $10,000 in new high-gloss flooring, new windows in all three bedrooms and the balcony, plus smooth-sliding patio doors for added comfort and efficiency. Two balconies offer wonderful outdoor space-the main balcony captures sunny southern views, while the second, located off the primary bedroom, provides a peaceful west-facing retreat. Perfect for morning coffee, evening relaxation, or simply enjoying the fresh air without the work of maintaining a home.The Bayshore has on site security, is a well-managed building with a welcoming renovated lobby featuring a fireplace, and an updated party/conference room nearing completion. Residents also enjoy a fitness centre, library, laundry facilities, and ample visitor parking.If you're ready to leave behind the upkeep of a larger home while still wanting room for guests, hobbies, entertaining, or a home office, this spacious condo offers an ideal balance of freedom and comfort. Lock the door, walk away, and enjoy a lifestyle where the maintenance is taken care of for you! An exceptional location puts you minutes from Frenchman's Bay, the waterfront, beach and boardwalk, parks, shops, restaurants, Pickering Town Centre, public transit, Pickering GO Station, Highway 401, and Lakeridge Health Ajax Pickering Hospital.Downsize your responsibilities-not your lifestyle. This is easy, comfortable living in a location you'll love. Book your showing today!

1210 Radom Street Unit 208, Pickering
1235 Radom Street Unit 62, Pickering
$529,900
3 Beds ⋅ 3 Baths ⋅ E13868066 MLS ⋅ Village By The Lake BLDG.
Welcome to Families, First-Time Home Buyers, Empty-Nesters, Or Any One Looking For A Fantastic Home In Beautiful Bay Ridges. This Is A Great Home For Someone In Need Of Three Bedrooms, Lots Of Space, And Fantastic Access To Pickering Town Centre. So Much To Offer Here, Stainless Steel Appliances, Storage Space, Functional Layout, Peaceful Backyard With Access To Lots Of Green Space In Complex. There Is A Full Standing Shower In The Basement. Amenities Include Tons Of Fun To Be Had At The Pool With Its Own Lifeguard During The Summer. Two Children's Playgrounds Near The Complex. Very Family-Friendly Amenities! Very Quick 10 To 15 Minute Walk To Pickering GO Station. Lots Of Transit Options. Stroll Over To Pickering City Centre In A Mere 20 Minutes. Easy Access To Frenchmans Bay. Convenient Location To Parking Lot Access And Visitor Parking Access. Fantastic Enclosed Yard With Tomato And Bell Pepper Garden With Lots Of Greenery Around. Bay Ridges Is A Fantastic Neighbourhood For Families Of All Ages and Sizes Looking For A Peaceful And Beautiful Community To Live In.

1235 Radom Street Unit 62, Pickering
5290 Old Brock Road, Pickering
$1,060,000
4 Beds ⋅ 2 Baths ⋅ E13860442 MLS
Peaceful Country Living Meets Modern Convenience in Claremont. A quieter way of life without sacrificing city convenience. Welcome to this charming, beautifully updated family residence. Set on a sun-drenched, half-acre lot adorned with mature apple and maple trees and manicured grounds, this home pairs the warm, relaxed vibe of a country retreat with sleek modern upgrades throughout.The Interior:The thoughtful interior features an open-concept living and dining area with fresh flooring and a walkout to the backyard. At the heart of the home, the renovated chef's kitchen boasts stainless steel appliances and an inviting center island-the natural gathering point for everyday life. Unwind in the warm living room by the gas fireplace, or enjoy slow mornings and evening views from the light-filled front sunroom. With four bedrooms, two beautifully updated bathrooms, and a generous family room, there is ample space for growing families and hosting guests.The Outdoor Oasis:Step outside into an entertainer's paradise. The expansive backyard offers endless space to play and relax, featuring a large sun deck for alfresco dining and a fire pit for starry summer nights. The substantial lot also presents valuable future potential for a detached garage or side addition.The Location:Enjoy Claremont's close-knit community, top-tier local school, and incredible outdoor recreation-from nearby golf and ski hills to hiking trails in the Rouge Valley. When duty calls, commuting is effortless with quick access to the GO Station, Hwy 401, and Hwy 407.

5290 Old Brock Road, Pickering
1402 Fordon Avenue, Pickering
$949,900
3 Beds ⋅ 2 Baths ⋅ E13740268 MLS
Prime South Pickering Location! Ideally situated in the desirable Bay Ridges/South Pickering Community. This home offers an exceptional combination of lifestyle & Convenience. Enjoy easy access to Lake Ontario, waterfront trails, parks, Frenchman's Bay, marinas & beaches. Perfect for the outdoor enthusiast & families. Conveniently located close to schools, shopping, restaurants, Pickering Town Centre & everyday services. Quick and nearby access to 401 & walk to the Go Sation. A fantastic location that truly offers the best of lakeside living with urban convenience.

1402 Fordon Avenue, Pickering
803 Fairview Avenue, Pickering
$949,000
4 Beds ⋅ 2 Baths ⋅ E13657952 MLS
Welcome to 803 Fairview Ave, Beautiful Bangalow Raised located in sought-after Bay Ridges! This well-maintained & 3 Bedroom, 1 Bathroom in Upstairs. Property boasts spacious living areas and1bed room ,Living & 1 Bathroom basement Apartment with a separate entrance providing the perfect opportunity for additional income or a separate living space. Close To Schools, Parks, Frenchman's Bay, Lake Ontario & Trails. Perfect For The Outdoor Enthusiast, Close To Go Station, Restaurants, Pickering Town Centre, Shopping And More. Seller can provide the City-approved building permit for 2,500 sq. ft. two-storey home at no additional cost.

803 Fairview Avenue, Pickering
1841 Fairport Road, Pickering
$1,299,900
4 Beds ⋅ 2 Baths ⋅ E13636036 MLS
Welcome to 1841 Fairport Rd, a turn-key bungalow tucked into Dunbarton-one of Pickering's most coveted, high-end enclaves. Set among multi-million dollar estates, this rare property boasts a jaw-dropping 75 by 420 ft flat and landscaped lot backing directly onto serene Dunbarton Creek Ravine. Your sprawling backyard is a true private oasis, complete with a powered structure ripe for conversion into a future pool house, workshop, or bunkie. Inside, the home shines with tasteful updates and brand-new flooring throughout. The renovated kitchen features sleek stainless-steel appliances and flows effortlessly into a beautiful, sunny solarium made for morning coffee. The fully finished basement serves up serious lifestyle versatility, offering a distinct separate entrance for potential rental income, plus an authentic wood stove for cozy winter evenings. With a massive driveway accommodating 6-car parking, hosting is completely effortless. A commuter's dream - Hwy 401 is close by for fast highway access, and the Pickering GO station is just a short ride away. This prime location perfectly balances absolute ravine serenity with unbeatable everyday connectivity to transit, top-tier schools, and local shopping. Don't miss this one. *Basement photos virtually staged*

1841 Fairport Road, Pickering
956 Bayshore Court, Pickering
$1,250,000
5 Beds ⋅ 3 Baths ⋅ E13459980 MLS
Nestled on a premium lot just steps from the shores of Lake Ontario this one-of-a-kind bungalow offers an incredible blend of space, versatility, and character. Originally built in 1953 for the landowner, this solid custom home has been thoughtfully expanded over the years while maintaining its timeless charm. Backing onto a picturesque creek (Glen Ravine Park), the property offers a peaceful natural setting rarely found in the area. Inside, you'll find a spacious layout featuring 3+2 bedrooms, a large living and dining room perfect for entertaining, and an impressive chef's kitchen loaded with premium features and finishes. The added family room creates the ideal gathering space for everyday living. Picture windows on the main level are a real wow factor. The finished basement offers exceptional in-law or future income potential with a separate walk-up entrance, kitchenette with space to expand, and additional bedrooms for extended family, young adults, or guests. Ready for you to complete the finishes! Car enthusiasts, hobbyists, and business owners will appreciate the oversized double garage - large enough to accommodate two pickup trucks, a workshop, storage loft, and even the possibility of a car lift. With parking for up to nine vehicles in the driveway, there's room for work vehicles, trailers, campers, and more. Step outside to enjoy the reinforced deck (approx 1100 sq feet) designed to support a hot tub (50 amp service available) while overlooking the expansive yard and tranquil creek setting. Shed with electrical. Sprinkler system. A truly unique property with no comparable home in the neighbourhood - offering endless possibilities, multi-generational living potential, and an unbeatable location within walking distance to the lake. Close to all amenities and enjoy the proximity to the Whites Road east and west 401 ramps.

956 Bayshore Court, Pickering
780 Liverpool Road, Pickering
$880,000
2 Beds ⋅ 1 Baths ⋅ E13048408 MLS
This is a large lot in an established South Pickering neighbourhood. At 80 x 190 feet, there's potential for severance into two lots. The property is walking distance to Frenchman's Bay Beach, the waterfront, restaurants, and everyday shopping. The Pickering GO station and Highway 401 are close by, and Pickering Town Centre is minutes away. Being sold under Power of Sale on an as-is, where-is basis.

780 Liverpool Road, Pickering
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