Rolling Acres Real Estate for Sale

27 Listings
Rolling Acres real estate features properties such as multi-storey townhouses and spacious detached houses in an accessible community of Whitby, close to the main streets of Rossland Road, Thickson Road, Taunton Road and Gerrard Road. Houses and townhouses in Rolling Acres are located on tree-lined streets and are close to many parks and recreational green spaces including Willow Park, contributing towards the laid back and peaceful atmosphere of the community. Real estate properties in Rolling Acres are just a short drive to many of the city conveniences located in central Whitby including shopping centres, movie theatres, restaurants and more.
52 Lady May Drive, Whitby
3
BEDS
4
BATHS
$899,900
FOR SALE
This All-Brick, Fully Detached Family Home Situated in Whitby's Dryden Trail Neighbourhood is Ready to Move-In and Enjoy! Updated from Top To Bottom, This Home Features 3 Bedrooms, 3.5 Bathrooms, a Finished Basement, and a Fully Landscaped Backyard. Quiet Family Neighbourhood, with Community Park Nearby and Close to Schools, Shopping, Dining, Entertainment, Transit, and Highways. You Don't Want to Miss This One!
36 Ravenview Drive, Whitby
4
BEDS
4
BATHS
$1,199,000
FOR SALE
Beautifully updated 6-bed executive home in Rolling Acres. Features include hardwood floors, a custom oak staircase, and a spacious primary retreat. The modern kitchen offers quartz countertops, stainless steel appliances, and a walk-in pantry. Conveniently located near public transit, Willow Park, gas stations, grocery stores, daycares, and ATMs. Home is being sold as-is.
118 Bridlewood Boulevard, Whitby
4
BEDS
3
BATHS
$899,000
FOR SALE
Beautiful 4 bedroom premium home backs onto beautiful green space and offers the perfect blend of comfort, style, and family living in a quiet, highly sought after neighbourhood. Featuring a spacious functional layout, this home is located just minutes to transit, schools, shopping, and all amenities.Lots of upgrades including crown mouldings, 9 foot ceilings, and hardwood flooring throughout. The bright sunroom provides additional living space perfect for relaxing or entertaining. Beautifully landscaped with impressive curb appeal, this home also features a rough in basement with income potential and a convenient second floor laundry. A true must see property.
2 Bettina Place, Whitby
3
BEDS
4
BATHS
$1,052,000
FOR SALE
Space to spread out. Space to come together. And a backyard that feels like your own private retreat. This beautifully updated family home offers 3 bedrooms, 4 bathrooms, and the kind of thoughtful layout that gives everyone room to breathe. A welcoming living room at the front of the home creates the perfect spot to gather with guests, while the open-concept kitchen, dining, and family room- with cozy gas fireplace-becomes the true heart of the home. Walk out from the dining area to a stunning curated garden complete with multiple sitting areas, gazebo, and outdoor bar-made for summer dinners, week cocktails, and hosting family and friends long into the evening. Upstairs, the primary suite feels like a true escape with a walk-in closet and luxurious 5-piece ensuite. The second bedroom also features a walk-in closet, while the second floor laundry room adds everyday convenience exactly where you need it most. The double car garage and mudroom make busy mornings, grocery runs, and snowy winters effortlessly practical. Downstairs, the finished basement offers exceptional flexibility with a large office space, TV/media area, and generous storage to help keep the rest of the home beautifully organized. Move-in ready and ideally located close to parks, schools, shopping, groceries, transit, and with easy access to Highways 401 and 407-this is the kind of home your family can truly grow into.
8 Inverary Court, Whitby
3
BEDS
3
BATHS
$1,149,999
FOR SALE
Welcome to 8 Inverary Court in one of Whitby's most sought-after family neighbourhoods. Built by respected builder DeNoble, this beautifully maintained home offers a rare layout with soaring ceilings and an open, airy feel throughout. Originally designed as a 4-bedroom model, one bedroom was thoughtfully removed to create the dramatic two-storey great room flooded with natural light. Set on a quiet dead-end court and backing onto greenspace, this home offers exceptional privacy while still being within walking distance to schools, parks, and everyday amenities. The main floor features hardwood flooring, a spacious formal dining room, bright home office/living room, and an inviting open-concept kitchen with breakfast area and walkout to the backyard patio. The stunning family room is the heart of the home with its soaring ceilings, oversized windows, and gas fireplace. Upstairs, the generous primary suite includes a large ensuite with soaker tub and separate shower, while two additional bedrooms provide excellent space for family or guests. Freshly painted throughout and meticulously cared for, this home is truly move-in ready. Major updates include the roof (2014), furnace (2017), and central air conditioning (2024). The unfinished basement offers excellent potential for future living space, gym, recreation room, or in-law setup. Outside, enjoy a private backyard retreat with interlock patio and mature trees backing onto greenspace with no rear neighbours. A rare opportunity to own a quality-built home in an exceptional Whitby location.
7 Treen Crescent, Whitby
3+1
BEDS
4
BATHS
$924,900
FOR SALE
Welcome To 7 Treen Crescent, A Beautifully Maintained 3+1 Bedroom, 4 Bathroom Family Home Located In One Of Whitby's Most Desirable Neighbourhoods. Offering A Spacious And Functional Layout, This Home Is Perfect For Growing Families And Those Who Love To Entertain. The Main Floor Features An Updated Kitchen With Elegant Granite Countertops Overlooking Your Private Backyard Oasis Complete With A Stunning Inground Pool - The Perfect Setting For Summer Gatherings, Relaxing Weekends, And Outdoor Entertaining. Bright And Inviting Principal Rooms Provide Plenty Of Living Space, While The Generous Primary Bedroom Offers A Private Ensuite Retreat. The Fully Finished Basement Includes An Additional Bedroom And Ensuite Bath, Ideal For Guests, Family Visits, Or A Home Office Setup. Situated In A Highly Sought-After, Family-Friendly Area Close To Top-Rated Schools, Parks, Shopping, Restaurants, Recreation Centres, And So Much More. Enjoy Convenient Access To Highway 401, Go Transit, And Major Commuter Routes, Making Travel Throughout The GTA Effortless. Minutes To Downtown Whitby, Waterfront Amenities, And All The Conveniences This Vibrant Community Has To Offer. A Rare Opportunity To Own A Move-In Ready Home That Perfectly Combines Comfort, Style, And Location. Recent Updates Include Furnace (2025), A/C (2025), Hot Water Tank (2025), And Pool Liner (2024).
39 Braebrook Drive, Whitby
4+1
BEDS
4
BATHS
$798,000
FOR SALE
Incredible opportunity to purchase a lovely 4-bedroom home nestled on one of the most sought-after streets in the Rolling Acres community. Updated eat-in kitchen with stainless steel appliances, granite counters and walk-out to rear yard. This family home offers a main floor sunken family room with fireplace, formal living & dining rooms, main floor laundry and plenty of storage space. Other notable features include hardwood floors, spacious principal rooms, 4 bathrooms and a finished basement with potential for an in-law suite. Direct access to double car garage via private driveway. Minutes to great schools, parks, shopping and dining. Family-friendly neighbourhood with easy access to highways and transit.
55 Belfountain Drive, Whitby
4
BEDS
3
BATHS
$1,098,999
FOR SALE
Beautiful 4 bedroom home located on a child friendly street in lovely Rolling Acres. Great location ,hardwood staircase, spacious eat in kitchen, breakfast bar, large pantry, gas fireplace on main floor, family room, crown moulding and beautiful hardwood floors, home features a 2 storey entrance, big primary bedroom with ensuite and walk in closet, close to school, shopping , park and more, less than 15 min. to HWY 401, 407, 412 and Go Station
27 Furrow Drive, Whitby
3
BEDS
3
BATHS
$749,900
FOR SALE
Great starter home in central Whitby. You cannot beat this location. Quiet street in a mature area. Close to everything including 401 & 407. Walking distance to St. Mark the Evangelist and John Dryden schools. All brick home. Kitchen has large breakfast area with walk- out to covered deck and private fully fenced yard. Great starter home. Shows well. Don't delay book your showing today.
31 Thames Drive, Whitby
2+2
BEDS
2
BATHS
$749,000
FOR SALE
This beautifully maintained 2+2 bedroom, 2 bathroom 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.
49 Bettina Place, Whitby
3
BEDS
4
BATHS
$800,000
FOR SALE
3 Bedroom Detached Home In Highly Sought-After Rolling Acres Community In Whitby * 1470 Sq Ft* Carpet Free Home* Freshly Painted * Bright Open-Concept Layout * Hardwood Stairs With Wrought Iron Spindles* Breakfast Area With Walk-Out To Deck * Primary Bedroom Featuring Walk-In Closet & 4Pc Ensuite * Totally Updated Finished Basement * New Bathroom Vanities * Convenient Garage Access* Backyard Concrete Patio With Gazebo * Family-Friendly Location Close To Parks, Schools, Transit & All Amenities. Roof (5yrs) Furnace ( 6yrs)
141 Waller Street, Whitby
3
BEDS
2
BATHS
$679,900
FOR SALE
This one truly has it all! Step into a beautifully updated 3-bed, 2-bath semi in one of Whitby's most sought-after neighbourhoods - the perfect blend of style, comfort, and modern convenience. Soaring 9-ft ceilings, expansive windows, and California shutters fill the home with natural light, while new LED lighting on the main level adds a warm, contemporary glow. The refreshed interior features a modern renovated kitchen, fully updated bathrooms, hardwood and ceramic flooring, and a smart thermostat for year-round efficiency. Thoughtfully upgraded closet doors and generous storage throughout elevate the home's functionality and design.The versatile third bedroom with a Murphy bed easily transforms from guest room to office to play space - whatever your lifestyle needs. Enjoy effortless indoor-outdoor living with a walkout from the kitchen to a spacious deck, perfect for morning coffee, summer BBQs, or hosting friends. Partially finished basement with finished rec room area, and plenty of storage and utility space rough-in for additional bathroom is already to go! An attached garage plus ample driveway parking make everyday life a breeze. Stylish, warm, and completely move-in ready - all in a prime location close to top schools, shops, and restaurants. Homes like this don't come up often, this is you're chance!
54 Waller Street, Whitby
4+1
BEDS
3
BATHS
$1,049,900
FOR SALE
Outstanding family home in a highly desirable neighbourhood! This spacious 4-bedroom property offers over 3,000 sq ft of finished living space, beautifully updated from top to bottom. The main floor features a newer kitchen with quartz countertops, quality stainless steel appliances, and a bright breakfast area with sliding doors leading to the stunning inground pool and manicured backyard. Enjoy hardwood flooring, a warm family room with wainscoting, and an open-concept living/dining room with French doors and elegant trim details. A main-floor office/den and a convenient laundry room with side entrance and garage access complete this level. The second floor offers an impressive primary suite with a sitting area, views of the pool, and a new 5-piece ensuite featuring granite counters, a soaker tub, and a glass shower. Three additional generous bedrooms with closets provide ample space for the whole family. The finished basement includes a large recreation room, an additional bedroom, and a rough-in for a future bathroom, offering excellent potential for customization. Located close to schools, shopping, transit, and just minutes to Hwy 407 & 401.Be sure to view the virtual tour and photos - this home is a must-see.
149 Braebrook Drive, Whitby
4
BEDS
4
BATHS
$1,449,000
FOR SALE
Welcome To Stunning Medallion-Built Executive Home Located In The Highly Sought-After Rolling Acres Community Of Whitby. Situated On A Premium Corner Lot, This Beautifully Upgraded Residence Offers Luxurious Living Space Featuring 11-Ft Smooth Ceilings, Hardwood Flooring, Elegant Iron Picket Staircase, And A Bright Open-Concept Layout. Gourmet Custom Kitchen With Granite Countertops &High-End Appliances. Flexibility For Family Living.
150 Lady May Drive, Whitby
3
BEDS
4
BATHS
$798,900
FOR SALE
Beautiful corner unit townhome in Whitby's highly sought-after Rolling Acres community. This bright and spacious home offers 3 bedrooms, 4 washrooms, and a functional open-concept layout designed for comfortable everyday living and entertaining. The main level features upgraded hardwood floors and ceramic tiles, a formal dining area, and a modern kitchen with brand-new countertops and breakfast bar setup. The breakfast area walks out to a large private fenced backyard, ideal for kids, pets, summer BBQs, or relaxing outdoors.The finished basement includes pot lights, a full washroom, and separate entrance through the garage, offering excellent flexibility as an entertainment space, home office, guest suite, or potential future studio apartment setup. The spacious primary bedroom features a walk-in closet and private ensuite bath. Freshly painted and move-in ready with major updates including roof (2019), tankless hot water tank (2019), and brand-new furnace (2026) for added peace of mind. Located in one of Whitby's most family-friendly neighbourhoods close to parks, trails, shopping, transit, highways 401 & 407, and sits in one of the highly-ranked schools in Durham Region. Rare opportunity to own a well-maintained corner unit with extra outdoor space in an established community families truly love!
51 Divine Drive, Whitby
4+1
BEDS
4
BATHS
$998,000
FOR SALE
Spacious 4+1 bedroom, 4 bathroom home situated on a desirable corner lot, offering a functional layout and excellent potential. Features include hardwood flooring, oak staircase, and a bright main floor with open-concept living and dining areas. Finished basement includes additional living space with kitchen, bedroom, and 3-piece bath. Property includes a separate side entrance and additional in-home modifications. Buyers to conduct their own due diligence regarding retrofit status and use. Property being sold in AS IS WHERE IS" condition. No representations or warranties. Exterior highlights include interlock walkways, extended driveway, and attached garage. Conveniently located close to schools, shopping, and major highways including 401 and 407.
112 Creekwood Crescent, Whitby
4
BEDS
4
BATHS
$699,000
FOR SALE
Welcome to 112 Creekwood - a move-in-ready freehold townhouse in one of Whitby's most family-friendly neighborhoods. Bright, spacious, and freshly painted throughout, this home offers a functional layout with generous living and dining areas, a walkout to a private fully fenced backyard, and an updated kitchen featuring granite countertops, stainless steel appliances, stylish backsplash, and plenty of natural light. Upstairs, you'll find three well-sized bedrooms, including a spacious primary retreat with a walk-in closet and 4-piece ensuite. The bonus family room with gas fireplace and soaring cathedral ceilings adds incredible flexibility - perfect as a second living area, home office, playroom, or easily converted into a fourth bedroom. The finished basement with a 3-piece bathroom provides even more usable space for guests, recreation, or extended family. Rare parking for 3-4 vehicles adds everyday convenience. Steps to top local schools, including Sir Samuel Steele and St. Mark the Evangelist, plus parks, transit, shopping, and everyday amenities. A clean, bright, and versatile freehold home in a prime Whitby location - perfect for first-time buyers, young families, or anyone looking for more space without the condo fees.
9 Mountainside Crescent, Whitby
4+1
BEDS
4
BATHS
$999,000
FOR SALE
Step into uncompromised luxury with this stunning 2,725 sq. ft. Cambridge Model home by Medallion Developments, offering 4+1 bedrooms and 5 bathrooms in a sleek, modern design. The open-concept main floor impresses with 11-ft ceilings, elegant hardwood flooring, and a gourmet kitchen featuring premium cabinetry and built-in appliances, all warmed by a cozy 3-way gas fireplace. Enjoy the convenience of main-floor laundry with a separate side entrance, ideal for multi-generational living or future flexibility. Upstairs, the primary suite is a true retreat with a spa-like 5-piece ensuite, complete with double sinks, a glass shower, and a soaker tub, plus a spacious walk-in closet. The second bedroom boasts its own private ensuite, while two additional bedrooms share a stylish Jack & Jill bathroom. The fully finished basement adds incredible value with a bright bedroom, a den, living area, kitchen, laundry, and a 4-piece bathroom. Move-in ready and designed for modern living, this home blends luxury and functionality seamlessly-schedule your private tour today.
54 Thames Drive, Whitby
3+1
BEDS
3
BATHS
$925,000
FOR SALE
Welcome to this beautifully upgraded home, where modern comfort meets thoughtful design. Featuring energy-efficient solar panels, a brand-new garage, and a fully renovated basement complete with a spacious bedroom and full washroom, this property offers exceptional versatility and style. Every detail has been carefully updated, creating a move-in-ready space perfect for families or those seeking extra living or rental potential.
92 Hartrick Place, Whitby
3+1
BEDS
4
BATHS
$939,922
FOR SALE
OFFER ANY TIME!!! Welcome to Amazing Home for Sale 3+1 Bedrooms and 4 Bathrooms. This meticulously maintained home is move-in ready The custom kitchen boasts quartz counters, a large island, stainless steel appliances, and custom cabinetry. Flooring enhances both the main and second floors. The Primary Bedroom features a newly built ensuite washroom that comes with a glass shower door and a modern shower. The finished basement includes an electric fireplace and a Potential Separate entrance to the basement, a feature wall with built-in shelves, and ample space for relaxation. Home is equipped with security system cameras and a touchpad key lock. Step outside to enjoy a private backyard with a deck, shed, and gas BBQ hookup. Driveway: With no sidewalk, the driveway accommodates parking for 4 cars. Walking distance to Transit /Plaza. Located in an AAA-rated school area, 5 minutes to Hwy 401 !!!! 4 Public & 4 Catholic schools serve this home. Of these, 8 have catchments. There are 2 private schools nearby.8 sports fields, 5 basketball courts and 7 other facilities are within a 20-minute walk of this home. Street transit stop less than a 1 min walk away. Rail transit stop less than 6 km away.
33 Bremner Street, Whitby
4+2
BEDS
4
BATHS
$1,380,000
FOR SALE
5 Year Old House on a Premium Lot. Quiet Family Friendly Street in One Of Whitby's Most Sought-After Neighborhoods. House Is Backing On To A Ravine And Walking Trail. No Neighbors Behind. Watch The Sunrise From your Living Room. Thousands Spent On Upgrades. Hardwood Floors, Upgraded Kitchen Cabinets, Handy Pantry, Gas Fireplace, Bi Bookcase, Pot Lights, Crown Molding. Open Concept W/Easy Flow From Dining Room To Lg Living Room Overlooking The Ravine And Eat-In Kitchen. 9' Ceilings, Sky light. Insulated Garage Ceiling, Ent From Garage W/Mudroom, 200 amp Service. Basement: Ove $100K Spent on Professionally Built New Legal Basement Apartment for Extra Income. Separate Private Entrance. In-Suite Separate Laundry. All New Appliances. Elegant Laminate Floors Through-Out. Kitchen With Ceramic Back-Splash, Quartz Counter-Tops, Rangehood And Dishwasher. Combined Living And Dining With Laminate Floors And Pot Lights. Bathroom With Glass Shower Enclosure And Tile Floors. 2 Good Size Bedrooms With Mirrored Closets And Large Windows. Close To Public Transit, Catholic And Public Schools. Parks and Shopping.
9 Lively Way, Whitby
4
BEDS
4
BATHS
$769,000
FOR SALE
Be the first owner of this beautiful brand-new traditional freehold Townhome with WALK OUTBASEMENT built by Acorn Developments. This bright and spacious Nordic Architecture inspired home features 4 good size Bedrooms and 3.5 bathrooms, 2,045 sq. ft, 9' smooth ceiling on Main Floor, Oak stairs, Extended Upper Kitchen Cabinets, and granite countertop and Stainless Steel appliances. Buy Directly from the Builder. Price does no include and is subject to HST & Home is qualified under the new Government Enhance HST New Home Rebate Incentives. (No Development charges, Tarion Warranty available). Conveniently located in the heart of Whitby. Public transit at doorsteps. Walking distance to Starbucks, Walmart, Daycare, Parks and playgrounds, groceries, shops, and dining. Easy access to both 401 & 407 for commuters. Luxury features include private Primary Bedroom level with 4-piece Ensuites, private balcony, and His & Her Walk-in closets, fully Walkout basement access to backyard. New Home, never lived in, Buy directly from the Builder. A Must See! Don't miss the opportunity to live in this urban charm Sincerely Acorn Community! Potl fee includes garbage disposal, snow removal & landscaping of the common area.
31 Gabrielle Crescent, Whitby
4
BEDS
3
BATHS
$994,000
FOR SALE
Welcome to this well-appointed 2-storey detached home in prime North Whitby. Featuring 4 spacious bedrooms, this home is ideal for growing families. The primary suite includes a large ensuite and walk-in closet, providing a private retreat. The main floor offers a spacious layout with eat in kitchen, large formal dining room, convenient laundry with extra storage and direct access to the garage. A partially finished basement adds additional living space with room to customize to your needs. Step outside to your own spacious yard, complete with an in-ground pool, perfect for summer entertaining. Situated on a quiet street in a family friendly neighbourhood, this home is just minutes to Highway 407, schools, parks, and all amenities.
25 Charterhouse Drive, Whitby
4
BEDS
3
BATHS
$1,299,000
FOR SALE
This Stunning Executive Home Boasts Impeccable Style & Design, Making It A Perfect Choice For The Most Discerning. With High-End Finishes Throughout, It's Clear That No Detail Has Been Overlooked In The Creation Of This Luxurious Living Space. One Of The Standout Features Of This Home Is Its Dream-Like Kitchen, Complete With Granite Countertops, Backsplash. Polished Porcelain Tiled Floors Only Add To The Overall Elegance And Sophistication Of This Space. The Family Room Is Another Highlight Of This Home With A Waffle Ceiling, A Custom Fireplace. 9Ft Smooth Ceilings, Can Be Found Throughout, Adding To The Overall High-End Feel Of This Property. With Four Exceptional Bedrooms Upstairs. The Luxurious Primary Bedroom Boasts A Five-Piece Ensuite, Spectacular Walk-In Closet! Beautiful Landscaping In Both The Front & Back Of The Property Includes A Stamped Concrete Driveway, As Well As A Backyard patio, Close To All Amenities!
1 Morningstar Avenue, Whitby
5+2
BEDS
6
BATHS
$1,588,888
FOR SALE
Welcome to 1 Morningstar Ave in Whitby's sought-after Rolling Acres community! This exceptional 3,794 sq ft home plus a 1,650 sq ft finished legal basement apartment offers over 5,400 sq ft of luxury living. The main floor features a brand-new designer kitchen (renovated 2025) with custom cabinetry, quartz counters, large pantry, and breakfast area open to the family room. Separate living, dining, and library rooms plus a powder room complete the spacious layout. The second floor boasts 5 extra-large bedrooms, each with an ensuite or semi-ensuite bath. The legal 2-bedroom basement suite includes a full kitchen, open living area, and separate entrance-perfect for rental income or extended family. Minutes to Hwy 401/407, top schools, parks, and shopping. A rare opportunity to own a fully upgraded, move-in-ready home in a prime Whitby location!
99 Creekwood Crescent, Whitby
3
BEDS
2
BATHS
$699,000
FOR SALE
Step into this stunning 3-bedroom townhouse located in the highly sought-after Rolling Acres community! Freshly painted throughout with brand-new rigid core vinyl plank flooring on the main level, a beautifully refreshed kitchen with refinished cabinets, and so much more. Perfectly situated near top-rated schools, shopping, and public transit, this home offers both comfort and convenience. An ideal choice for young families or couples. Don't miss the opportunity to make it yours!
25 Fieldnest Crescent, Whitby
3
BEDS
4
BATHS
$949,000
FOR SALE
Great property in a high demand neighborhood. Easy access to highways (401/407), Go Transit, Rec Centre W/Hockey & Figure Skating. Garage access. Hardwood Stairs. High Energy Efficient Home-3 Spacious bedrooms and 4 washrooms, Fully renovated-1. Metal roofing (Aug 2025), 2. Washrooms (2024), 3. Heat pump (2024), 4. Furnace and tankless water heater (2022), 5. Washer & Dryer (2022), 6. Porch & pot lights (2021). Ideally located near schools, high school, shopping plaza, and 1 min walk to public transit.
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