Rolling Acres Homes with 31-50 Approx Age

Rolling Acres Homes with 31-50 Approx Age

Welcome to Rolling Acres, an enchanting neighborhood nestled in the heart of Whitby, Ontario. Known for its picturesque landscapes and friendly community atmosphere, Rolling Acres is a hidden gem that offers residents the perfect blend of suburban tranquility and urban convenience.

The charm of Rolling Acres is evident in its well-maintained homes, predominantly built between 1973 and 1990, giving the area a unique character that appeals to a variety of homeowners. These properties, with their mature trees and spacious yards, provide an ideal setting for families, retirees, and everyone in between. Many homes feature classic designs with modern updates, allowing residents to enjoy the best of both worlds.

Living in Rolling Acres means you are just a stone's throw away from an array of amenities. The neighborhood boasts excellent schools, parks, and recreational facilities, making it a prime location for families. The nearby shopping centers and restaurants cater to all your daily needs, ensuring convenience is at your fingertips.

For nature enthusiasts, Rolling Acres is close to beautiful green spaces and trails, perfect for leisurely strolls, cycling, or simply enjoying the great outdoors. The community spirit here is palpable, with friendly neighbors who often gather for local events and activities, fostering a sense of belonging.

With its ideal location, charming homes, and vibrant community, Rolling Acres is not just a place to live—it's a place to thrive. Discover your dream home in this delightful neighborhood, where comfort and convenience come together seamlessly.

Newest Rolling Acres Homes with 31-50 Approx Age

$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
$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
$799,990
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
$1,249,000
4 Beds ⋅ 3 Baths ⋅ E13237324 MLS
Welcome to Whitby's Prestigious Rolling Acres Community! This impressive all-brick detached two-storey home seamlessly blends sophisticated updates with exceptional everyday functionality. Meticulously maintained and beautifully presented, the property offers outstanding curb appeal with mature trees, manicured landscaping, an interlocking walkway, and a widened driveway. The renovated kitchen is the heart of the home featuring rich cabinetry, granite countertops, an oversized centre island, and a built-in pantry-perfect for both daily living and entertaining. Overlooking the kitchen, the inviting family room offers a gas fireplace and creates a warm, connected gathering space. Main floor living/dining room with hardwood floors. A spacious upper-level great room showcases high ceilings, pot lights, and a second gas fireplace, providing an ideal setting for large family gatherings or entertaining guests. The home features four generously sized bedrooms, each with ample closet space. The main bathroom has been updated including a walk-in shower and bluetooth mirror. The primary suite offers a walk-in closet and a private 4-piece ensuite.Thoughtfully designed with multi-generational and growing families in mind, this home offers an abundance of versatile living space, including multiple sitting areas throughout. The finished basement features two additional lounge areas and a custom-built bar, creating yet another exceptional space to relax and entertain. Step outside and enjoy your own private backyard retreat. Just in time for summer, the inground swimming pool and tiered deck provide the perfect setting for outdoor enjoyment, offering both privacy and a welcoming atmosphere for family and friends. **Please refer to the attached schedule for a complete list of upgrades.**Ideal location close to shopping, places of worship, excellent schools, and brand-new Rose Valley Community Park. Convenient access to public transit, Highway 401/407, making commuting a breeze.

16 Donald Wilson Street, Whitby
$735,888
4 Beds ⋅ 2 Baths ⋅ E13157956 MLS
This beautifully maintained 2+2 bedroom, 2 bathroom with finished basement with large rec room this home offers the perfect blend of comfort, space, and versatility in one of Whitby's most sought-after family neighbourhoods.Step inside to a bright and inviting main floor featuring a functional layout, spacious living and dining areas, and large windows that fill the home with natural light. The kitchen offers ample cabinetry and workspace, ideal for everyday living and entertaining.The main level includes one primary and a large flex space that could easily work as a second bedroom, while the fully finished lower level provides two additional bedrooms, a second full bathroom, and plenty of flexible space-perfect for extended family, guests, or a home office setup. Large recreation room. Enjoy a private backyard ideal for relaxing and enjoy the pond or entertaining, along with a quiet, family-friendly street close to parks, top-rated schools, shopping, and all amenities. Easy access to highways and transit makes commuting a breeze.

31 Thames Drive N, Whitby
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