Rolling Acres Homes for Sale

Rolling Acres Homes for Sale

Welcome to Rolling Acres, a hidden gem nestled in the heart of Whitby, Ontario. This charming neighborhood is renowned for its picturesque landscapes, friendly community atmosphere, and convenient access to urban amenities. With its tree-lined streets and well-maintained parks, Rolling Acres offers a serene suburban lifestyle that is perfect for families, retirees, and everyone in between.

One of the standout features of Rolling Acres is its strong sense of community. Neighbors often come together for seasonal events, fostering friendships and a welcoming environment. The area is also home to excellent schools, making it an ideal place for families looking to provide their children with quality education. Nearby recreational facilities, including sports fields and walking trails, ensure that residents can enjoy an active lifestyle right in their backyard.

For those seeking homes for sale, Rolling Acres boasts a diverse range of properties, from charming bungalows to modern two-storey houses. Each home is designed with comfort and style in mind, featuring spacious layouts and beautiful outdoor spaces perfect for entertaining or relaxing after a long day. With competitive pricing and a variety of options, there’s something for everyone in this desirable neighborhood.

Rolling Acres is not just a place to live; it’s a community to thrive in. With its blend of tranquility and accessibility to shopping, dining, and major transportation routes, this neighborhood is poised to be your perfect new home. Come explore the possibilities and discover why so many are proud to call Rolling Acres home!

Newest Rolling Acres Homes for Sale

$1,195,000
4 Beds ⋅ 2 Baths ⋅ E13769596 MLS
BUILDER & INVESTOR ALERT! Rare 80 x 200 ft (0.37 acre) lot on Rossland Rd E in Whitby's sought-after Rolling Acres neighbourhood. Purchase on its own or combine with the adjacent lot at 1910 Rossland Rd E to assemble an exceptional 160 x 200 ft (0.73 acre) parcel with 160 ft of frontage on Rossland. Currently tenanted and generating holding income while you plan your next move. Zoned R2, with strong potential for future intensification, including street townhomes, subject to rezoning and approvals through the Town of Whitby and Region of Durham. New development is already underway just steps from this exceptional opportunity, reflecting the continued growth and demand in this established, family-friendly pocket of east Whitby. Minutes to Thickson Square, Dryden Square, top-rated schools, parks and trails, with quick access to Hwy 401/412 and Whitby GO. Buy alone for a renovate-and-hold play, or assemble both lots for a larger development vision. Lot sold as-is, where-is. Do not walk the property or approach tenant without an accompanied appointment. A rare chance to secure land in one of Whitby's most established communities.

1906 Rossland Road E, Whitby
$1,195,000
4 Beds ⋅ 2 Baths ⋅ E13769594 MLS
BUILDER & INVESTOR ALERT! Rare 80 x 200 ft (0.37 acre) lot on Rossland Rd E in Whitby's sought-after Rolling Acres neighbourhood. Purchase on its own or combine with the adjacent lot at 1906 Rossland Rd E to assemble an exceptional 160 x 200 ft (0.73 acre) parcel with 160 ft of frontage on Regional Road 28. Currently improved with a bungalow, vacant and ready for your renovation, rental or redevelopment plans. Zoned R2, with strong potential for future intensification, including street townhomes, subject to rezoning and approvals through the Town of Whitby and Region of Durham. New development is already underway just steps from this exceptional opportunity, reflecting the continued growth and demand in this established, family-friendly pocket of east Whitby. Minutes to Thickson Square, Dryden Square, top-rated schools, parks and trails, with quick access to Hwy 401/412 and Whitby GO. Buy alone for a renovate-and-hold play, or assemble both lots for a larger development vision. Legal, deeded lot sold as-is, where-is. Do not walk the property without an accompanied appointment. A rare chance to secure land in one of Whitby's most established communities.

1910 Rossland Road E, Whitby
$975,000
4 Beds ⋅ 3 Baths ⋅ E13767746 MLS
Welcome to 41 Winterberry, a beautifully maintained all-brick two-storey home situated in the highly desirable Rolling Acres neighbourhood. Offering a spacious and functional layout, this carpet-free home features hardwood flooring throughout and is perfect for growing families and those who love to entertain. The inviting main floor features a bright living room with a cozy gas fireplace, a separate formal dining room, and an updated eat-in kitchen showcasing custom-made cherry cabinetry, Cambria countertops, stainless steel appliances, and undermount lighting, offering plenty of space for everyday family living. Convenient main-floor laundry with a separate side-door entrance adds to the home's practicality. Upstairs, you'll find four spacious bedrooms, including a generous primary retreat complete with a 5-piece ensuite. Outside, enjoy newer front landscaping, a double-car garage, and a backyard designed for summer fun with an above-ground pool complete with a newer gas heater. A wonderful opportunity to settle into a sought-after, family-friendly neighbourhood and make this home your own!

41 Winterberry Drive, Whitby
$719,999
4 Beds ⋅ 2 Baths ⋅ E13763232 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
$949,900
4 Beds ⋅ 3 Baths ⋅ E13759274 MLS
Welcome to this stunning all brick 4 bedroom home in a prime North Whitby location! The inviting, spacious foyer offers convenient access to the main floor laundry and insulated garage. The beautifully updated eat in kitchen is the heart of the home, featuring a massive quartz island and plenty of space for family gatherings and entertaining. Gorgeous hardwood floors and crown moulding flow throughout the main level. Upstairs, the impressive principal retreat features a full ensuite and huge walk in closet, along with three additional spacious bedrooms. The finished basement adds even more living space with brand new carpet and large recreation room. Step outside to your own private backyard oasis, beautifully landscaped and perfect for relaxing or entertaining. A spacious, move in ready family home in one of Whitby's most desirable areas!

39 Mcivor Street, Whitby
$899,000
4 Beds ⋅ 4 Baths ⋅ E13757086 MLS
Welcome to this beautiful detached home featuring 3+1 bedrooms and 4 bathrooms in a desirable Whitby neighbourhood. Conveniently located close to schools, parks, shopping, restaurants, public transit and recreational facilities. Easy access to Highways 401, 407 and 412 makes commuting a breeze. Enjoy the convenience of nearby GO Transit and all the amenities Whitby has to offer. Numerous upgrades totaling approximately $100,000, including renovated bathrooms(2026), interlock patio(2024), kitchen(2026), windows(2024), refinished floors(2026), AC (2025), HWT (2021), roof (2016), furnace(2022), interior painting(2026), back door(2024), garage door(2019), and light fixtures(2026). A wonderful opportunity for families looking for a spacious, upgraded home in a well-connected community.

97 Bach Avenue, Whitby
$1,148,800
4 Beds ⋅ 4 Baths ⋅ E13752570 MLS
Lovingly cared for home built by renowned builder Delta Rae Homes, Durhams premier builder for over 20 years! The home is being offered for the first time from the original owners, a rare find! Beautiful 4 bedroom, 4 bathroom home boasts 2600 squre feet - a true gem on a child-friendly and family orientated area in one of Whitby's most convenient neighbourhoods! Amazing location close to Highways, Transit & just steps to top-rated schools, plazas & all other amenities! This move-in ready home has been renovated & upgraded throughout, offering comfort, style, & functionality. Step inside to find a bright, spacious layout with large rooms with plenty of natural light. The modern renovated kitchen features fresh cabinets, stainless steel appliances, extra pantry space - perfect for any home chef! The huge Eat-In kitchen area has large patio doors opens to a lush, private backyard oasis with a HUGE concrete deck, colourful gardens, & green space that feels like your own private paradise. Amazing mature trees offers plenty of privacy in the heart of Whitby! The main floor also offers a rare direct access to the garage & an amazing service stairwell directly to the partially finished basement. This private side entrance is excellent income potential or the ideal setup for multi-generational family living. Possibilities are endless! The cozy Family room offers a gas fireplace. This home offers a convenient Dining room-right off the kitchen, making entertaining family & friends a delight! On the upper level this home has a huge primary bedroom as a peaceful retreat complete with a walk-in closet, multiple windows, separate sitting area to relax and unwind & a rarely offered RENOVATED FULL 4-piece ensuite, with a stand alone tub & shower to enjoy quiet time after a hectic day! Three additional bedrooms offer generous double closet space for family & guests alike! The front features beautiful landscaping, a front veranda to enjoy your morning coffee or relaxing quiet time!

66 BRIDLEWOOD Boulevard, Whitby
$749,900
3 Beds ⋅ 3 Baths ⋅ E13751776 MLS
Welcome To 39 Bach Avenue, A Meticulously Maintained, Bright And Inviting Home In The Highly Sought-After Rolling Acres Neighbourhood. Step Inside To A Spacious Foyer Featuring Large-Format Ceramic Tile, Leading Into A Sun-Filled Living Room With Soaring 9-Foot Ceilings.At The Heart Of The Home Is The Beautifully Updated Kitchen (2026), Thoughtfully Designed For Both Everyday Living And Entertaining. Highlights Include New Quartz Countertops, A Stylish New Backsplash, Refreshed Cabinetry And A Generous Breakfast Bar With Seating For Up To Four. The Kitchen Flows Seamlessly Into The Dining Area, Where Large Windows Overlook The Lush Backyard. Step Outside Onto The Expansive Deck-An Ideal Setting For Outdoor Dining, Entertaining And Easy Access To The Garden.Upstairs, The Spacious Primary Bedroom Features A Double Closet And Access To The Beautifully Renovated Semi-Ensuite Bathroom (2024), Complete With A Large Vanity, Stunning Walk-In Shower And Separate Soaker Tub. Two Additional Bedrooms Offer Generous Proportions And Large Windows That Fill Each Room With Natural Light.The Finished Walkout Basement Provides Even More Versatile Living Space, Perfect For A Family Room, Home Office, Gym Or Play Area, Along With Plenty Of Storage And A Convenient Cold Room.Thoughtful Upgrades Throughout Include An Owned Tankless Water Heater (2024), Updated Powder Room (2026), Attic Insulation (2025), Washer And Dryer (2023), Basement Carpeting (2023), Furnace And A/C (2015), And Driveway Sealing (2024).Ideally Situated In The Heart Of Rolling Acres, This Home Is Close To Parks, Trails, Schools, Shopping, Restaurants, Recreation And Public Transit, With Convenient Access To Highways 401, 407 And 412, As Well As Whitby GO. Beautifully Cared For And Thoughtfully Updated, 39 Bach Avenue Offers Comfortable, Move-In-Ready Living In A Welcoming, Family-Friendly Neighbourhood.

39 Bach Avenue, Whitby
$939,000
3 Beds ⋅ 4 Baths ⋅ E13751754 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
$1,099,000
5 Beds ⋅ 4 Baths ⋅ E13745356 MLS
Welcome To A Home Where Space, Style And Everyday Comfort Come Together Beautifully. Offering 4+1 Bedrooms, 4 Bathrooms And Over 3,000 Sq. Ft. Of Finished Living Space, This Impressive Family Home Is Located In One Of Whitby's Most Desirable Communities, Surrounded By Excellent Schools, Parks And Everyday Conveniences. Step Inside To A Bright, Spacious Layout Designed To Accommodate Both Busy Family Life And Effortless Entertaining. The Main Floor Features Generous Principal Rooms And Premium Kentwood Originals Hardwood Flooring, Creating A Seamless Flow Throughout The Living Spaces. At The Heart Of The Home, The Custom Kitchen Offers Granite Countertops, Abundant Cabinetry, Under-Cabinet Lighting And A Gas Stove, With Plenty Of Room For Gathering, Cooking And Entertaining. Upstairs, Four Generously Sized Bedrooms Provide Comfortable Private Spaces For The Entire Family, Each Featuring Hardwood Flooring And Custom Built-In Closet Organizers. The Spacious Primary Suite Is A True Retreat, Complete With A Walk-In Closet, Private Ensuite And Additional Custom Built-Ins.The Finished Lower Level Extends The Home's Versatility With A Large Recreation Room, Wet Bar, 2-Piece Bathroom And An Additional Bonus Room Ideal For A Home Office, Gym, Guest Room Or Playroom. Outside, The Fully Fenced Backyard Is Ready To Be Enjoyed All Summer Long. A Large Deck Surrounds The Semi-Above-Ground Pool, Creating An Inviting Setting For Outdoor Dining, Entertaining And Relaxing With Family And Friends. Beautifully Maintained, Exceptionally Spacious And Thoughtfully Designed With Functionality In Mind, This Is A Home That Offers Room To Grow, Entertain And Make Your Own - All In A Sought-After, Family-Friendly Neighbourhood You'll Love To Call Home.

57 Morning Glory Crescent, Whitby
$829,990
4 Beds ⋅ 4 Baths ⋅ E13741710 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
$949,000
4 Beds ⋅ 3 Baths ⋅ E13738790 MLS
Welcome to 33 Waller Street, a beautifully maintained Tormina-built Westchester Model nestled in one of Whitby's most sought-after family communities. Cherished by its owners, this spacious home offers the perfect blend of comfort, functionality, and location for first-time buyers, growing families, and move-up purchasers alike. Set on a quiet, family-friendly street, this home is surrounded by parks, walking trails, and excellent schools, creating an ideal environment for raising children and building lasting memories. Families will appreciate the convenience of having both public and French-Immersion Catholic schools nearby, along with easy access to recreation facilities, shopping, dining, and everyday amenities. The neighbourhood is known for its strong sense of community, mature landscaping, and welcoming atmosphere. Inside, the popular Westchester floor plan offers generous principal rooms and a practical layout designed for everyday living and entertaining. Whether you're hosting family gatherings, enjoying quiet evenings at home, or creating space for a growing household, this home provides the flexibility today's buyers are looking for. Commuters will appreciate the convenient access to Highway 401, Highway 412, Highway 407, and the Whitby GO Station, making travel throughout the GTA simple and efficient. The location also offers quick access to shopping, restaurants, community centres, and recreational amenities while maintaining the peaceful feel of an established residential neighbourhood. A rare opportunity to own a quality-built Tormina home in a mature, family-oriented Whitby neighbourhood where pride of ownership and community spirit continue to shine.

33 Waller Street, Whitby
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