Pickering Homes with 51-99 Approx Age

Pickering Homes with 51-99 Approx Age

Welcome to Pickering, Ontario—a vibrant city that beautifully marries the charm of suburban living with the conveniences of urban life. Nestled along the shores of Lake Ontario, Pickering boasts stunning waterfront parks, scenic trails, and a rich tapestry of community events that foster a close-knit atmosphere. With easy access to major highways and public transit, residents enjoy seamless connectivity to downtown Toronto and beyond, making it an ideal place for commuters and families alike.

When it comes to real estate, Pickering offers a diverse range of homes, including those with a charming history and character. For buyers seeking properties with an approximate age of 51-99 years, you’ll discover a unique selection of homes that reflect the architectural styles of their time, each with its own story to tell. These residences often feature spacious layouts, mature landscaping, and a sense of nostalgia that new builds simply can’t replicate.

Living in a home with a bit of history in Pickering means you’re not just buying a property; you’re investing in a lifestyle. Enjoy the benefits of established neighborhoods, where tree-lined streets and friendly neighbors create a welcoming environment. Plus, with nearby amenities such as shopping centers, schools, and recreational facilities, everything you need is just a stone’s throw away.

Whether you’re a first-time homebuyer, a growing family, or looking to downsize, Pickering’s blend of history and modern convenience makes it a truly enchanting place to call home. Come explore the possibilities in this dynamic city!

Newest Pickering Homes with 51-99 Approx Age

1841 Fairport Road, Pickering
$1,228,000
4 Beds ⋅ 2 Baths ⋅ E14140856 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
566 Rougemount Drive, Pickering
$1,199,000
6 Beds ⋅ 4 Baths ⋅ E14140814 MLS
Rosedale design meets south Rosebank: deceptively large, architecturally stunning, and built for multi-generational living in Pickering's most exclusive pocket! Forget cookie-cutter - this property serves up over 3,300 sq ft of finished living space across two separate structures. The main house features a sophisticated, multi-level layout reminiscent of a Rosedale cottage estate. The heart of the home is a stunning kitchen transported straight to Tuscany with granite tile floors, matching granite counters, and a sun-drenched, skylit family room. Rich hardwood leads to the primary bedroom's spa ensuite, while the massive, finished basement adds a 5th bedroom, gym, and a new bathroom with a luxury jetted dual shower. But the true magic of this property unfolds as you step outside. Tucked privately at the rear of your sprawling property sits a fully finished, detached 480 sq ft guest suite. Complete with its own kitchen, new appliances, bedroom, bathroom, two separate entrances, and an independent heat pump, it offers unmatched versatility. Whether it's used for independent multi-generational living, long-term guests, or a spectacular executive home office, it is a rare auxiliary layout that bends completely to your family's needs. Home has been updated to 200amp service and panel. Enjoy a massive deck, a 24-ft pool with a new liner, and parking for 4. Walk to Blaisdale Montessori and other top schools in the area. Nestled between Rouge Valley and Lake Ontario - minutes to Highway 401 and Rouge Hill GO. Don't miss this exceptional opportunity!

566 Rougemount Drive, Pickering
1235 Radom Street Unit 62, Pickering
$489,000
3 Beds ⋅ 3 Baths ⋅ E14140072 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
780 Liverpool Road, Pickering
$880,000
2 Beds ⋅ 1 Baths ⋅ E14131964 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
874 Grenoble Boulevard, Pickering
$715,000
4 Beds ⋅ 2 Baths ⋅ E14126934 MLS
**ATTENTION INVESTORS, CONTRACTORS, RENOVATORS & BUYERS WITH VISION!** Fantastic Opportunity To Unlock The Potential Of This Bungalow Situated On A Generous 50 x 100 Ft Lot In Pickering's Desirable Bay Ridges Community! Offering Approximately 1,135 Sq. Ft. On The Main Floor Plus An Additional 1,135 Sq. Ft. Basement With A Separate Entrance, This Home Provides Plenty Of Space And Possibilities! The Main Level Features A Kitchen Updated Approximately 6 Years Ago, Providing A Great Starting Point For Your Renovation Plans. The Home Is In Need Of Improvements And Updating, Offering The Perfect Opportunity To Renovate, Customize And Make It Your Own! Whether You're An Investor Looking For Your Next Project, A Contractor Ready To Transform A Property, Or A Buyer Dreaming Of Creating Your Ideal Home, This Property Is Full Of Potential! **LOCATION, LOCATION, LOCATION!** Just Minutes From The Beautiful Shores Of Lake Ontario, Frenchman's Bay, Scenic Waterfront Trails, Parks, Beaches And Pickering's Charming Nautical Village With Its Restaurants, Cafes And Marina. Conveniently Located Near Pickering GO Station, Highway 401, Schools, Shopping And Everyday Amenities. Enjoy The Charm Of An Established Residential Neighbourhood With The Added Benefit Of Being Close To The Waterfront! **BRING YOUR VISION AND IMAGINATION - A WONDERFUL OPPORTUNITY TO CREATE SOMETHING SPECIAL!**

874 Grenoble Boulevard, Pickering
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
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
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
Start Your Search

How much is your home worth?

Get instant property value now!