Rolling Acres Real Estate

Rolling Acres Real Estate

Welcome to Rolling Acres, a charming neighborhood nestled in the vibrant city of Whitby, Ontario. This picturesque community is a hidden gem that offers the perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, young professionals, and retirees alike.

Rolling Acres is characterized by its tree-lined streets, beautifully maintained parks, and a strong sense of community. Residents enjoy a peaceful atmosphere, with ample green spaces for outdoor activities, picnics, and leisurely strolls. The neighborhood is home to several parks, including the popular Rolling Acres Park, where families can gather for fun-filled weekends or simply relax amidst nature.

Education is a top priority in Rolling Acres, with access to highly-rated schools that cater to all age groups. Parents can feel confident knowing their children are receiving a quality education close to home. Additionally, the neighborhood boasts a variety of shopping options, from local boutiques to larger retail centers, ensuring that all daily needs are just a short drive away.

For those who commute, Rolling Acres offers convenient access to major highways and public transit, making it easy to reach downtown Toronto and other neighboring cities. Whether you’re seeking a cozy family home or a modern townhouse, the real estate options in Rolling Acres are diverse and appealing.

Embrace the welcoming spirit and vibrant lifestyle of Rolling Acres. With its perfect combination of community charm, convenience, and natural beauty, it’s no wonder that this neighborhood is a sought-after destination for those looking to plant roots in Whitby. Come discover your dream home in Rolling Acres today!

Newest Listings in Rolling Acres

$1,149,000
5 Beds ⋅ 4 Baths ⋅ E13805512 MLS
Welcome to this gorgeous, lovingly cared family home on a QUIET, SAFE COURT in Whitby's favorite ROLLING ACRES! Set on a premium private lot, you get nearly 2,900 SQ FT ABOVE GROUND plus a HUGE FINISHED BASEMENT. Start every day in your SUN-DRENCHED SUNKEN LIVING ROOM with tall, soaring windows that flood the home with warm MORNING SUNSHINE-the ultimate spot to sip coffee and recharge. Enjoy the ease of a quiet MAIN FLOOR OFFICE for effortless remote work, cook in the open chef's kitchen, and walk right out to your private BACKYARD RETREAT with an entertainer's deck, gazebo, and relaxing as-is HOT TUB. Upstairs features 4 BIG BEDROOMS, highlighted by a private primary suite with a hotel-style 5-PC SPA BATH and walk-in closet. The finished basement adds a 5TH BEDROOM, game room, rec room, and HUGE STORAGE SPACES-ideal for teens, guests, or in-laws. Best of all, every major upgrade is ALREADY PAID FOR AND DONE: brand-new OWNED WATER & AIR FILTER (2025), high-efficiency FURNACE & A/C (2022), modern Stainless Steel APPLIANCES WITH WASHER/DRYER (2021), ROOF (2018). Complete with 6 PARKING SPACES, TOP-RATED SCHOOLS (8+ RATING) just minutes away, and fast access to shops, Whitby GO, and HWY 401/407/412. 100% MOVE-IN READY -Book Your Private Tour Today!

19 Wigston Court, Whitby
$1,129,900
4 Beds ⋅ 3 Baths ⋅ E13803194 MLS
Welcome to this beautiful and lovingly cared-for family home, offering a bright and airy layout. The main floor features a spacious living and dining area with hardwood flooring, recessed lighting and detailed trim and baseboards throughout. The inviting family room offers hardwood flooring, a gas fireplace and an open-concept connection to the well-appointed kitchen. The kitchen is thoughtfully designed with extra-high custom cabinetry, under- and over-cabinet lighting, quartz countertops, a large centre island with seating, ceramic flooring and a stylish tile backsplash. The adjacent breakfast area provides a walkout to the backyard and overlooks the beautifully landscaped outdoor space. Convenient main-floor laundry adds functionality and ease to everyday living. Upstairs, four generously sized bedrooms provide plenty of room for the entire family. The spacious primary retreat features a walk-in closet and a private four-piece ensuite with ceramic flooring, a whirlpool tub and separate shower. Three additional bedrooms each offer comfortable living space, double closets and broadloom flooring. A second four-piece bathroom and convenient main-floor powder room complete the home. The backyard is an exceptional extension of the living space, featuring two expansive decks ideal for relaxing, dining and entertaining. One deck offers a gazebo-covered seating area, while the second is designed for outdoor dining and includes a natural gas BBQ. A built-in Jacuzzi hot tub provides the perfect spot to unwind, while the remaining lawn offers plenty of room for children and pets to enjoy. Interlocking adds both function and curb appeal along the side of the home and beside one of the decks. The unfinished basement offers excellent potential for future living space, along with a cold cellar and rough-in for plumbing. With its spacious principal rooms, thoughtful upgrades and outstanding backyard, this home is perfectly suited to comfortable family living and entertaining.

104 Fencerow Drive, Whitby
$915,000
4 Beds ⋅ 4 Baths ⋅ E13793658 MLS
Welcome to 54 Thames Drive, a beautifully updated 3+1 bedroom, 4-bathroom home in Whitby's highly desirable Rolling Acres community. Offering a functional, family-friendly layout and thoughtfully upgraded living space, this move-in-ready home is designed for comfortable everyday living and entertaining. The bright main level features a welcoming open-concept layout with modern finishes and plenty of natural light. The updated kitchen flows seamlessly into the living and dining areas, creating an inviting space for family gatherings and entertaining. Upstairs, you'll find three generously sized bedrooms, including a spacious primary retreat. The professionally finished basement provides valuable additional living space with an extra bedroom and bathroom-perfect for a home office, guest suite, recreation area, or growing family. Outside, enjoy a private backyard and the convenience of three parking spaces. Additional highlights include solar panels and a newer garage, adding both functionality and long-term value. Located in sought-after Rolling Acres, you're minutes from excellent schools, parks, shopping, restaurants, transit and major commuter routes.3+1 Bedrooms 4 Bathrooms Finished Basement Solar Panels 3 Parking Spaces Updated Throughout Prime Rolling Acres Location. A fantastic opportunity to own a spacious, move-in-ready home in one of Whitby's established family communities. Come experience 54 Thames Drive for yourself.

54 Thames Drive, Whitby
$1,100,000
4 Beds ⋅ 3 Baths ⋅ E13802384 MLS
Welcome to 84 Bedell! Nestled on a quiet, family-friendly street, this beautiful home sits on an extra-deep, pool-sized lot-and a backyard like this is rarely offered! Enjoy a gorgeous mature yard, inground saltwater pool, built-in BBQ, and beautiful professional interlocking-creating the perfect setting for summer entertaining and making memories with family and friends.Inside, the updated kitchen overlooks the backyard, making it easy to stay connected while entertaining. The separate living and dining rooms offer wonderful versatility and can easily be used as a home office, playroom, or additional living space to suit your family's needs. The spacious primary bedroom features a walk-in closet and an updated 5-piece, spa-inspired ensuite. Three additional generously sized bedrooms provide plenty of space for family, guests, or a home office.The unspoiled basement is ready for your vision and offers excellent potential for additional living space, a recreation room, gym, or home theatre. With numerous updates throughout, this is a home you can move right in and enjoy! Located in a wonderful Whitby neighbourhood, close to excellent schools including St. Paul, St. Mark's, John Dryden, Father Leo J. Austin Secondary School, and Sinclair Secondary School. Conveniently located near the 401 and 407, with shopping, restaurants, parks, and everyday amenities close by. A beautiful home, an incredible backyard, and a location your family will love-welcome home to 84 Bedell! Updates incl: furnance 2014, AC 2017, Eavestrough 2019, roof 2013, pool liner 2022, robatic cleaner 2022.

84 Bedell Crescent, Whitby
$1,099,000
5 Beds ⋅ 4 Baths ⋅ E13796176 MLS
Offering more than 3,500 sq. ft. of finished living space, this beautifully cared-for home delivers the space, comfort and flexibility today's families are looking for.The main level is bright, welcoming and designed to flow effortlessly from everyday living to entertaining. A dedicated home office, open oak staircase and spacious living areas set the tone, while the renovated kitchen (2015) anchors the home with Cambria quartz countertops, an induction stove and open sightlines into the family room. A wood-burning fireplace adds warmth and character, while pot lights throughout the main floor create a clean, updated feel.Upstairs, the generous primary suite features hardwood flooring, a walk-in closet and a renovated 4-piece ensuite (2011) with a rain shower. The main family bathroom was also updated in 2012, offering a fresh and functional space for the rest of the household.The newly finished basement (2025) significantly expands the home's versatility, with a large recreation area, egress window, separate den and 3-piece bathroom. Whether used as a guest space, second office, gym, playroom or teen retreat, the layout offers plenty of options.Outside, the oversized backyard provides exceptional space for entertaining, relaxing and play. A large deck with a remote-controlled awning creates a comfortable outdoor living area and an easy extension of the home.Additional features include an owned tankless hot water system, 200-amp electrical service, wiring for a future hot tub, an additional 15-amp exterior electrical connection, and a furnace and air conditioner (2013) that have been professionally serviced annually.Spacious, thoughtfully updated and exceptionally well maintained, this is a home that offers room to grow, flexible living space and a backyard designed to be enjoyed.

29 Stratton Crescent, Whitby
$699,900
4 Beds ⋅ 4 Baths ⋅ E13791246 MLS
Beautiful 2-story 4 bedroom detached house in desirable area of Whitby. This home features a large eat-in kitchen with ceramic flooring, ceramic backsplash, window and walk out to the backyard. Family room with hardwood floors, fireplace and crown moldings. Living room with hardwood floors, French doors, crown moldings and a window. Dining room with hardwood floors, French doors and a window. Primary bedroom with broadloom, 5 piece ensuite and a walk-in closet. Second bedroom with broadloom, double closet and a window. Third bedroom with broadloom, double closet and a window. Forth bedroom with broadloom, double closet and a window. An open concept finished basement with broadloom, dry bar, games area and a two piece washroom. Main floor laundry, garage access into the house. Close to all amenities: schools, shopping and transit.

38 Brownell Street, Whitby
$918,800
3 Beds ⋅ 4 Baths ⋅ E13791066 MLS
Move-in ready and truly turn-key, this 3-bedroom home has been lovingly cared for by its original owner and sits in one of Whitby's most convenient spots - close to fantastic schools, parks, and everyday amenities and shops, so you're never far from what you need. Inside, the home has clearly been well cared for, freshly painted (2026), with new flooring on both the main floor and upstairs.This main floor is full of light, thanks to an abundance of beautiful windows throughout. The open-concept kitchen and dining area is practical and attractive - a great space for everyday living and entertaining alike - with a walkout straight to the backyard for easy indoor-outdoor flow. Rounding out the level is convenient garage access and a 2-piece powder room, adding everyday functionality to a genuinely lovely space.The upgrades here are extensive and include: furnace (2021), new 60-gallon hot water tank (2023), AC (2025), upstairs windows (2016), newer ground floor windows, roof shingles (approximately 2016), and a new front door. Upstairs, three good-sized bedrooms give everyone their own space, along with a 3-piece ensuite and another full 4-piece washroom. The fully finished basement is bright and cozy, with good-sized windows that bring in plenty of natural light. It features a dedicated office, a large carpeted family room, and a convenient 2-piece washroom, as well as a cold room and plenty of extra storage and laundry space.The backyard is particularly lovely - private, attractive, and thoughtfully finished. A spacious deck sets the stage for outdoor dining and relaxing evenings, while established trees and hedges frame the space in greenery and create a real sense of seclusion. A good-sized storage shed adds handy extra space for tools, toys, or seasonal items. Well-kept and full of character, it's an outdoor space that's ready to enjoy from day one.

34 Bridlewood Boulevard, Whitby
$999,000
6 Beds ⋅ 4 Baths ⋅ E13789200 MLS
BRIGHT & BEAUTIFULLY RENOVATED 4+2 BED, 4-BATH FAMILY HOME WITH LEGAL BASEMENT APARTMENT IN HIGHLY DESIRABLE ROLLING ACRES! Extensively upgraded throughout with approximately $150K INVESTED IN RENOVATIONS, offering a bright, spacious and functional layout designed for modern family living. The main level features 9-FT CEILINGS, HARDWOOD FLOORING, POT LIGHTS, CALIFORNIA SHUTTERS & CROWN MOULDING, complemented by separate living and dining areas and a comfortable family room with fireplace. The NEWLY RENOVATED KITCHEN (2022) features a large pantry and walk-out to the patio, perfect for everyday living and entertaining. Upstairs offers generous bedrooms and excellent family space. The professionally finished LEGAL BASEMENT APARTMENT features a SEPARATE ENTRANCE, FULL KITCHEN & 2 SPACIOUS BEDROOMS, providing outstanding flexibility for extended family or additional income potential. Beautifully landscaped exterior with FRONT INTERLOCK (2022) and numerous major updates including ROOF (2021), WINDOWS (2021), A/C (2021), FLOORING (2022), FURNACE (2025) & CENTRAL HUMIDIFIER (2026). A truly MOVE-IN-READY HOME in one of Whitby's most sought-after family communities, close to excellent schools, parks, shopping, transit and everyday amenities.

157 Waller Street, Whitby
$995,000
4 Beds ⋅ 3 Baths ⋅ E13788698 MLS
Welcome to 17 Chatterson St in the desirable community of Rolling Acres! RECENTLY UPGRADED HOME. All brick, 2008 built and impeccably maintained single-family home. 2 car garage with interior access & mudroom. Fantastic curb appeal: updated covered porch with tile flooring, brick cladding upgrade around windows, and landscaped backyard. On the main floor: gleaming hardwood floors & stairs, formal dining area, living room with fireplace and well-appointed kitchen. The upper floor boasts 3+1 bedrooms (all with walk in closets!), large laundry room; and primary bedroom with huge 5 piece ensuite. Basement is fully finished and is current used as a recreational area; ready for your personal touches! This home is perfectly situated for convenience- access to many shopping center's/plazas, highly rated schools, and even the new Thermea Spa within minutes! Pride of ownership truly shows here- squeaky clean and ready to move- in..This is a must- see!

17 CHATTERSON Street, Whitby
$999,999
6 Beds ⋅ 4 Baths ⋅ E13776384 MLS
A MUST-SEE! Welcome to 84 Braebrook Drive, an impressive all-brick detached residence nestled in the prestigious Rolling Acres community of Whitby. Situated on a generous lot, this beautifully appointed home offers Refined living space, thoughtfully designed for both elegant entertaining and comfortable family living.The home features 4+2 bedrooms and 4 bathrooms, complemented by a spacious family room, expansive kitchen with breakfast area, and a professionally finished basement offering exceptional additional living space. Recent upgrades include a fully renovated two-bedroom basement with heated floors, new light fixtures throughout, new flooring in the primary bedroom, a new refrigerator, and a new washer and dryer.The main floor showcases soaring 11-foot ceilings, pot lights, and an inviting three-way fireplace, creating an impressive yet welcoming atmosphere. The luxurious primary retreat features 10-foot ceilings and a beautifully appointed ensuite complete with a glass-enclosed shower and double vanity.Additional highlights include granite kitchen countertops, an interlock driveway, charming front porch, attached garage, and a fully fenced private yard.Ideally located close to parks, schools, shopping, dining, transit, and major amenities, this exceptional residence offers an outstanding blend of luxury, space, comfort, and modern upgrades in one of Whitby's most desirable family-friendly communities. A rare opportunity that truly must be seen to be appreciated!

84 Braebrook Drive, Whitby
$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
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