Houses for sale in Whitby Rolling Acres area

Newest MLS listings in Whitby Rolling Acres area

Homes for sale in Whitby - Rolling Acres

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  • 25 Winterberry Drive in Whitby: Rolling Acres E12444341 - House

    25 Winterberry Drive Rolling Acres Whitby L1R 1Z2
    Main Photo: 25 Winterberry Drive in Whitby: Rolling Acres E12444341 - House

    25 Winterberry Drive Whitby L1R 1Z2 Rolling Acres

    $975,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12444341
    Bedrooms:
    5
    Bathrooms:
    4
    From the moment you enter, you ll be greeted by an impressive 18-foot ceiling in the entrance and a spacious, open-concept layout perfect for entertaining, with a generous dining area, a Chef s kitchen with gas oven and and a breakfast island , with a walkout to a beautifully designed deck added in 2023. Private fenced yard, A main-floor office provides flexible use as an extra bedroom if needed. Upper level offers four well-appointed bedrooms with high-quality Berber flooring and a thoughtful layout ideal for a growing family. The finished lower level expands your living space with a large recreational area, gas fireplace, with bathroom, and pot lights throughout. Ashfault driveway 2024, A superb residence in the heart of Whitby s Rolling Acres community. Minutes to Durham College and Ontario Tech, shopping, plazas, restaurants, and quick access to Hwy 407/401. This home blends modern convenience with timeless comfort, featuring Nest smart thermostats, wireless cameras, and smart speakers for seamless living. More details
    Listed by RE/MAX ULTIMATE REALTY INC.
    LISTING DETAILS
    John Owen, Broker

  • 155 Lady May Drive in Whitby: Rolling Acres E12443689 - House

    155 Lady May Drive Rolling Acres Whitby L1R 3M4
    Main Photo: 155 Lady May Drive in Whitby: Rolling Acres E12443689 - House

    155 Lady May Drive Whitby L1R 3M4 Rolling Acres

    $699,900
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12443689
    Bedrooms:
    3
    Bathrooms:
    4
    Tired of cookie-cutter homes? Or those listings saddled with monthly maintenance fees? This 4-bath home is a breath of fresh air, designed with versatility in mind. Three separate entrances to the basement yes, three. That means endless options: teen retreat, in-law suite, hobby studio, or even a private guest space. Hardwood floors? Everywhere. Even the stairs. The main floor is wide open, with a seamless living/dining/kitchen flow, upgraded cabinetry, and a tumbled marble backsplash that adds just the right touch of character. Step through the sliding doors to your deck overlooking a fenced backyard ideal for summer BBQs or letting the dog out with ease. Upstairs, the oversized primary suite pampers with its own ensuite, while the secondary bedrooms are anything but small. Downstairs, the lower level delivers again: a full bath, garage access, and a walkout to the backyard perfect for creating a truly separate space. And lets talk location: the north end of Whitby is as good as it gets. Minutes from shopping, the 407, and a cycling path that practically calls your name on the weekend. Whether you're a first-time buyer, a growing family in need of a teen hangout, or downsizers who still want space for visiting family this one checks the boxes. More details
    Listed by KELLER WILLIAMS ENERGY REAL ESTATE
    LISTING DETAILS
    John Owen, Broker

  • 14 Bach Avenue in Whitby: Rolling Acres E12442834 - House

    14 Bach Avenue Rolling Acres Whitby L1R 2M1
    Main Photo: 14 Bach Avenue in Whitby: Rolling Acres E12442834 - House

    14 Bach Avenue Whitby L1R 2M1 Rolling Acres

    $874,900
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12442834
    Bedrooms:
    4
    Bathrooms:
    3
    This spacious 4-bedroom, 2-car garage home is tucked into a family-friendly neighbourhood and filled with thoughtful updates that blend comfort and functionality. Inside, enjoy 9-foot ceilings and newer hardwood on the main level and a fully finished basement featuring a cozy gas fireplace - ideal for family gatherings, movie nights, or a home office setup. Key upgrades include windows, roof, furnace, and a refreshed front porch and walkway, with added perks like central vacuum and 200-amp service in the garage to enhance everyday living. Step outside to your private backyard retreat, complete with a pergola, patio furniture, BBQ area, shed, and a hot tub - perfect for entertaining or unwinding after a long day. Primary bedroom includes 4-piece ensuite. 6 cars total parking. More details
    Listed by KELLER WILLIAMS ENERGY REAL ESTATE
    LISTING DETAILS
    John Owen, Broker

  • 30 Chatsworth Crescent in Whitby: Rolling Acres E12441987 - House

    30 Chatsworth Crescent Rolling Acres Whitby L1R 1J3
    Main Photo: 30 Chatsworth Crescent in Whitby: Rolling Acres E12441987 - House

    30 Chatsworth Crescent Whitby L1R 1J3 Rolling Acres

    $985,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12441987
    Bedrooms:
    4
    Bathrooms:
    4
    Open house Saturday and Sunday, October 4 & 5 from 2 to 4 PM! Welcome to this beautifully maintained 4-bedroom, 4-bathroom home in the highly sought-after Rolling Acres community of Whitby. Offering a perfect balance of comfort and style, this home is ideal for families and entertainers alike. The main floor features formal living and dining rooms, a bright eat-in kitchen with a centre island and built-in stove and cooktop overlooking the backyard, and a cozy family room with fireplace. Enjoy the convenience of a main-floor laundry room with garage access and side entrance. Upstairs you'll find four spacious bedrooms, including a primary bedroom with walk-in closet and 4-piece ensuite featuring a soaker tub and separate shower. The fully finished basement expands your living space with a recreation room, wet bar, 3-piece bathroom, and an additional area perfect for a home office, gym, or guest room. Step outside to your private backyard oasis complete with in-ground pool, rubber granule surface landscaping, gazebo with natural gas firepit, and natural gas BBQ hookup , and bar fridge, the ultimate setting for family fun and entertaining. Notables: Broadloom on Stairs 2024, Ingound Pool and Landscaping with outdoor kitchen 2020, Roof (approx. 5 years). Close to top-rated schools, parks, shopping, transit, and all amenities in a family-friendly neighbourhood this is the home you've been waiting for! Check Out The Virtual Tour! More details
    Listed by ROYAL HERITAGE REALTY LTD.
    LISTING DETAILS
    John Owen, Broker

  • 47 Scepter Place in Whitby: Rolling Acres E12440532 - House

    47 Scepter Place Rolling Acres Whitby L1R 3A8
    Main Photo: 47 Scepter Place in Whitby: Rolling Acres E12440532 - House

    47 Scepter Place Whitby L1R 3A8 Rolling Acres

    $974,900
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12440532
    Bedrooms:
    4
    Bathrooms:
    4
    Welcome To This Stunning, Move-In Ready Home Nestled In The Highly Sought After And Family Friendly Neighbourhood Of Rolling Acres! The Main Floor Boasts Hardwood Flooring Throughout, Access To The Garage From The Front Foyer, A Spacious Combined Living And Dining Area With Large Windows That Fill The Space With Natural Light, And A Separate Family Room Featuring A Cozy Fireplace And Views Of The Backyard. The Renovated, Eat-In Kitchen Is A Showstopper With Quartz Countertops, Under-Cabinet Lighting, Soft Close Cabinets, A Stylish Backsplash, And A Convenient Walkout To The Deck And Fully Fenced Backyard, Perfect For Family Living And Entertaining. Upstairs, You'll Find Four Generously Sized Bedrooms, Including The Beautiful Primary Suite With Double Door Entry, A Walk-In Closet, And A Beautifully Updated Ensuite Complete With A Double Vanity And Separate Glass-Enclosed Shower. A Convenient Four-Piece Main Bathroom And A Laundry Room With A Spacious Linen Closet Complete The Upper Level. The Finished Basement Adds Fantastic Extra Living Space, Featuring Pot Lights Throughout, Making It Ideal For A Rec Room, Home Office, Or Play Area. There Is Also A Convenient 4th Bathroom! Step Outside To Your Private Backyard, Complete With A Brand New Deck & Side Fence And Mature Trees That Offer Privacy And Shade, Perfect For Hosting Gatherings Or Relaxing With The Family. Situated In A Mature Neighbourhood, This Home Is Just Minutes From Schools, Parks, Shopping, And More. Don't Miss The Opportunity To Make This Beautiful Property Your Forever Home! EXTRAS: Fridge (2019), Dishwasher (2019), Microwave (2019), Roof (2019), Furnace (2019, As Per Previous Owners), A/C Replaced (2020), Kitchen Renovated (2021), Ensuite Bathroom Renovated (2021), Front Landscaping (2024), Newly Built Deck (2025), Backyard Side Fences (2025), Siding On Bay Window (2025), Outdoor Columns (2025). *See Attached Fact Sheet For All Dates & Information* More details
    Listed by KELLER WILLIAMS ENERGY REAL ESTATE
    LISTING DETAILS
    John Owen, Broker

  • 27 Mac Carl Crescent in Whitby: Rolling Acres E12439534 - House

    27 Mac Carl Crescent Rolling Acres Whitby L1R 2T7
    Main Photo: 27 Mac Carl Crescent in Whitby: Rolling Acres E12439534 - House

    27 Mac Carl Crescent Whitby L1R 2T7 Rolling Acres

    $1,249,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12439534
    Bedrooms:
    4
    Bathrooms:
    3
    Experience Elevated Living in North Whitby ! Welcome to this beautifully upgraded family home, tucked away on a premium 50 fot lot on a peaceful crescent surrounded by executive residences and mature tree lines. Offering an impressive 2,937 sq. ft. of above ground living space, this property combines style, comfort and functionality. A professionally landscaped front yard and lush garden create a warm first impression. Step inside to discover a bright, open concept layout featuring freshly painted walls and rich hardwood flooring throughout - a carpet free home! The spacious main floor is designed for everyday comfort and effortless entertaining. The bright living and dining areas flow into a modern, updated kitchen featuring sleek stainless steel appliances, elegant quartz countertops and plenty of workspace for the family chef. Walk out to a large, maintenance free composite deck, perfect for relaxing or hosting summer gatherings in your private backyard oasis. A grand circular staircase leads to the second floor, where the primary suite feels like a peaceful escape with its generous sitting area, a large walk-in closet and an updated spa like 5-piece ensuite. Three additional large bedrooms provide plenty of room and comfort for the whole family. Well maintained and updated over the years, this home features a newer roof (2013), stylishly renovated kitchen and bathrooms (2020), an owned hot water tank (2022), upgraded garage doors (2015), a durable composite deck (2013) and freshly paved driveway (2022). The laundry can be relocated to the second floor if desired. This is a rare opportunity to secure an elegant, move in ready home in one of North Whitbys most established and prestigious neighbourhoods. More details
    Listed by RE/MAX COMMUNITY REALTY INC.
    LISTING DETAILS
    John Owen, Broker

  • 33 Mappin Way in Whitby: Rolling Acres E12439264 - House

    33 Mappin Way Rolling Acres Whitby L1R 0R4
    Main Photo: 33 Mappin Way in Whitby: Rolling Acres E12439264 - House

    33 Mappin Way Whitby L1R 0R4 Rolling Acres

    $679,900
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12439264
    Bedrooms:
    2
    Bathrooms:
    3
    Offers anytime - no offer date! Presenting a fantastic opportunity for first-time buyers or those seeking low-maintenance living at 33 Mappin Way - a beautifully maintained 2-bedroom, 2.5-bathroom townhouse built by Minto in 2021. Located in the desirable Rolling Acres community of Whitby, this home features a thoughtful layout and stylish finishes throughout. Step into the open-concept main level featuring upgraded luxury vinyl plank flooring and a modern eat-in kitchen complete with stainless steel appliances. A spacious, private covered balcony extends the living space, perfect for relaxing outdoors. Upstairs, you'll find two generously sized bedrooms and two full bathrooms, including a primary suite with a large walk-in closet, a 2nd closet and a 3-piece ensuite. Convenient garage access & powder room on the ground level! This is a great opportunity to own a modern townhouse located just minutes from the 401, 407, top-rated schools, shopping centres, parks & all of Whitby's amenities - offered at a fantastic price! More details
    Listed by DORNAN REALTY INC.
    LISTING DETAILS
    John Owen, Broker

  • 81 Sutcliffe Drive in Whitby: Rolling Acres E12439172 - House

    81 Sutcliffe Drive Rolling Acres Whitby L1R 0R4
    Main Photo: 81 Sutcliffe Drive in Whitby: Rolling Acres E12439172 - House

    81 Sutcliffe Drive Whitby L1R 0R4 Rolling Acres

    $649,900
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12439172
    Bedrooms:
    2
    Bathrooms:
    3
    Welcome to this stunning townhome in the highly sought-after Rolling Acres community of Whitby! Featuring 2 spacious bedrooms, 3 modern bathrooms, and rare parking for 3 vehicles, this home is the perfect blend of style and function. The open-concept layout boasts a bright and inviting living space, while the chefs kitchen shines with quartz countertops and premium finishes ideal for entertaining or everyday living. Located in one of Whitby's most desirable neighbourhoods, you will enjoy easy access to top-rated schools, parks, shopping, dining, and convenient commuter routes. With its elegant design, generous parking, and unbeatable location, this home is a must-see for buyers seeking comfort, convenience, and modern living in Rolling Acres. Don't miss your chance to call this beautiful property home! More details
    Listed by RE/MAX HALLMARK FIRST GROUP REALTY LTD.
    LISTING DETAILS
    John Owen, Broker

  • 43 Chatterson Street in Whitby: Rolling Acres E12435736 - House

    43 Chatterson Street Rolling Acres Whitby L1R 0B3
    OPEN HOUSE: Oct 05, 2025
    02:00 PM - 04:00 PM EDT
    Open House on Sunday, October 5, 2025 2:00PM - 4:00PM
    Main Photo: 43 Chatterson Street in Whitby: Rolling Acres E12435736 - House

    43 Chatterson Street Whitby L1R 0B3 Rolling Acres

    $1,049,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12435736
    Bedrooms:
    3
    Bathrooms:
    3
    Welcome to this spacious and bright detached 2-storey home in Whitby's sought-after Rolling Acres community. Featuring 3 generous bedrooms and 3 bathrooms, this home is designed for modern family living. The sun-filled principal rooms are accented with California shutters, offering both style and privacy. Enjoy a large kitchen with stainless steel appliances and plenty of counter storage space. Upstairs, the impressive primary bedroom retreat features a walk-in closet, and a luxurious 5-piece ensuite with double vanity, soaker tub, and separate shower. The finished basement adds even more living space with a large rec room, perfect for entertaining, a home theatre, or a play area. With a family-friendly layout, tons of storage space, and a prime location close to schools, parks, shopping, and transit, this home is the perfect blend of comfort and convenience. More details
    Listed by AREA REALTY INC.
    LISTING DETAILS
    John Owen, Broker
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  • 36 Charterhouse Drive in Whitby: Rolling Acres E12434445 - House

    36 Charterhouse Drive Rolling Acres Whitby L1R 3R8
    Main Photo: 36 Charterhouse Drive in Whitby: Rolling Acres E12434445 - House

    36 Charterhouse Drive Whitby L1R 3R8 Rolling Acres

    $1,185,000
    Residential Freehold
    Status:
    Active
    MLS® Num:
    E12434445
    Bedrooms:
    4
    Bathrooms:
    4
    Welcome to this beautifully appointed executive home offering over 2,500 sq. ft. of finished living space in the sought-after Rolling Acres community. Featuring 4 spacious bedrooms and 4 bathrooms, this home is perfect for growing families or those who love to entertain. Step inside to discover an elegant open-concept dining area with gleaming hardwood floors that flow into a bright and airy great room, complete with large windows, a cozy gas fireplace, and views of the private, fenced backyard. The chefs kitchen is a showstopper, featuring a centre island, stainless steel appliances, custom backsplash, and a sunlit breakfast area with walkout to the deck - ideal for summer dining and entertaining. Convenient main floor amenities include a powder room and laundry room. Upstairs, the generous primary suite boasts a massive walk-in closet and a luxurious 5-piece ensuite with double sinks and a soaker tub. Two bedrooms share a stylish Jack and Jill bathroom, while the fourth bedroom enjoys its own private 4-piece ensuite. A versatile computer nook completes the second floor, perfect for homework or a home office. Additional highlights include California shutters throughout, ample closet space, and an unfinished basement offering endless potential. Located close to top-rated schools, parks, shopping, transit, and more, this exceptional home truly has it all. More details
    Listed by RE/MAX ROUGE RIVER REALTY LTD.
    LISTING DETAILS
    John Owen, Broker
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Data was last updated October 5, 2025 at 02:15 AM (UTC)
This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.
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This website may only be used by consumers that have a bona fide interest in the purchase, sale, or lease of real estate of the type being offered via the website. The data relating to real estate on this website comes in part from the MLS® Reciprocity program of the PropTx MLS®. The data is deemed reliable but is not guaranteed to be accurate.