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Houses for Sale in Rolling Acres Whitby Under $5 Million

Showing results 1 - 30 of 48

Looking for houses under $5m for sale in Rolling Acres, Whitby? With Square Yards Canada, discover a vast range of properties within your budget in Rolling Acres across Toronto. If you plan to buy houses under $5m in Rolling Acres, Whitby, you can refine your search by property size, specific amenities, and property age. Filter the listings by the number of bedrooms, bathrooms, and surface area to match your requirements. Our listings feature a wide range of Rolling Acres houses for sale under $5m, including freehold properties, condos, and commercial spaces.

Last Updated: September 26, 2026

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8 Watersdown Crescent, Durham, ON , MLS #E13825666 , Image - 1

8 Watersdown Crescent Rolling Acres, Whitby, Durham, ON MLS® E13825666

Residential Freehold (Detached)

$999000.0

4 +1 Beds
5 Baths
3000-3500 sq-ft

Magnificent 4+1 bed, 4 bath executive home on a large lot in a prestigious enclave. Soaring 2-storey foyer w/wall of windows 7 chandelier, rare octago

47 Photos

54 Thames Drive, Durham, ON , MLS #E13793658 , Image - 1

54 Thames Drive Rolling Acres, Whitby, Durham, ON MLS® E13793658

Residential Freehold (Detached)

$915000.0

3 +1 Beds
4 Baths
1500-2000 sq-ft

Welcome to 54 Thames Drive, a beautifully updated 3+1 bedroom, 4-bathroom home in Whitby's highly desirable Rolling Acres community. Offering a functi

Open House : Sat Oct 03, 01:00 PM to 03:00 PM

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8 Butterfield Crescent, Durham, ON , MLS #E13827418 , Image - 1

8 Butterfield Crescent Rolling Acres, Whitby, Durham, ON MLS® E13827418

Residential Freehold (Detached)

$748000.0

4 Beds
3 Baths
2000-2500 sq-ft

NO ACCESS, Ravine Lot , Fully Detached, Need TLC, Situated in a prime location with Unbelievable Breathtaking Views Of Nature Surrounding You, A Forma

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33 Waller Street, Durham, ON , MLS #E13738790 , Image - 1

33 Waller Street Rolling Acres, Whitby, Durham, ON MLS® E13738790

Residential Freehold (Detached)

$899000.0

Price drop by 5.3%

4 Beds
3 Baths
2000-2500 sq-ft

Welcome to 33 Waller Street, a beautifully maintained Tormina-built Westchester Model nestled in one of Whitby's most sought-after family communities.

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84 Braebrook Drive, Durham, ON , MLS #E13776384 , Image - 1

84 Braebrook Drive Rolling Acres, Whitby, Durham, ON MLS® E13776384

Residential Freehold (Detached)

$999999.0

4 +2 Beds
4 Baths
2000-2500 sq-ft

A MUST-SEE! Welcome to 84 Braebrook Drive, an impressive all-brick detached residence nestled in the prestigious Rolling Acres community of Whitby. Si

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57 Sutcliffe Drive, Durham, ON , MLS #E13824510 , Image - 1

57 Sutcliffe Drive Rolling Acres, Whitby, Durham, ON MLS® E13824510

Residential Freehold (Att/Row/Townhouse)

$815000.0

3 +1 Beds
3 Baths
1100-1500 sq-ft

Welcome to this beautifully appointed, 3 bedroom, 2.5 bathroom freehold townhouse, where timeless style meets effortless living. With upgraded finishe

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39 Bach Avenue, Durham, ON , MLS #E13751776 , Image - 1

39 Bach Avenue Rolling Acres, Whitby, Durham, ON MLS® E13751776

Residential Freehold (Detached)

$749900.0

3 Beds
3 Baths
1100-1500 sq-ft

Welcome To 39 Bach Avenue, A Meticulously Maintained, Bright And Inviting Home In The Highly Sought-After Rolling Acres Neighbourhood. Step Inside To

Open House : Sun Sep 27, 01:00 PM to 03:00 PM

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84 Bedell Crescent, Durham, ON , MLS #E13802384 , Image - 1

84 Bedell Crescent Rolling Acres, Whitby, Durham, ON MLS® E13802384

Residential Freehold (Detached)

$1100000.0

4 Beds
3 Baths
2500-3000 sq-ft

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 i

Open House : Sun Sep 27, 01:00 PM to 03:00 PM

50 Photos

16 Donald Wilson Street, Durham, ON , MLS #E13700070 , Image - 1

16 Donald Wilson Street Rolling Acres, Whitby, Durham, ON MLS® E13700070

Residential Freehold (Detached)

$1199000.0

Price drop by 2.1%

4 Beds
3 Baths
2500-3000 sq-ft

Welcome to Whitby's Prestigious Rolling Acres Community! This impressive all-brick detached two-storey home seamlessly blends sophisticated updates wi

Open House : Sat Sep 26, 01:00 PM to 03:00 PM

50 Photos

57 Morning Glory Crescent, Durham, ON , MLS #E13745356 , Image - 1

57 Morning Glory Crescent Rolling Acres, Whitby, Durham, ON MLS® E13745356

Residential Freehold (Detached)

$1099000.0

4 +1 Beds
4 Baths
2000-2500 sq-ft

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 Fini

Open House : Sat Sep 26, 09:30 AM to 11:30 AM

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15 Mountainside Crescent, Durham, ON , MLS #E13812752 , Image - 1

15 Mountainside Crescent Rolling Acres, Whitby, Durham, ON MLS® E13812752

Residential Freehold (Link)

$898888.0

4 Beds
3 Baths
2000-2500 sq-ft

Welcome to 15 Mountainside Crescent, a lovely 4-bedroom, 3-bathroom detached-link family home located in Whitby's premier Rolling Acres neighbourhood.

Open House : Sat Sep 26, 01:00 PM to 03:00 PM

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17 Burgundy Court, Durham, ON , MLS #E13816052 , Image - 1

17 Burgundy Court Rolling Acres, Whitby, Durham, ON MLS® E13816052

Residential Freehold (Detached)

$1589900.0

2 +2 Beds
3 Baths
2000-2500 sq-ft

Welcome To 17 Burgundy Court - A Custom-Built Executive Bungalow On One Of The Most Spectacular Lots In Whitby's Coveted Rolling Acres Community. Tuck

Open House : Sun Sep 27, 01:00 PM to 03:00 PM

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34 Bridlewood Boulevard, Durham, ON , MLS #E13791066 , Image - 1

34 Bridlewood Boulevard Rolling Acres, Whitby, Durham, ON MLS® E13791066

Residential Freehold (Detached)

$918800.0

3 Beds
4 Baths
1500-2000 sq-ft

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 sp

Open House : Sun Sep 27, 11:00 AM to 01:00 PM

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3 Griffen Place, Durham, ON , MLS #E13808070 , Image - 1

3 Griffen Place Rolling Acres, Whitby, Durham, ON MLS® E13808070

Residential Freehold (Detached)

$1150000.0

4 +2 Beds
4 Baths
2000-2500 sq-ft

Modern 4-Bed Detach w/ Legal 2-Bed Basement Suite - Whitby (Rolling Acres), Welcome to 3 Griffen Place, a solid all-brick family home on a quiet stree

Open House : Sun Oct 04, 01:00 PM to 03:00 PM

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4 Divine Drive, Durham, ON , MLS #E13672542 , Image - 1

4 Divine Drive Rolling Acres, Whitby, Durham, ON MLS® E13672542

Residential Freehold (Detached)

$1079000.0

4 +1 Beds
4 Baths
2500-3000 sq-ft

Welcome to this exceptional family home in the highly desirable Rolling Acres! 4+1 Bedrooms, 4 bathrooms, Finished Basement. 2530 Sq.Ft above Grade +

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19 Lively Way, Durham, ON , MLS #E13546284 , Image - 1

19 Lively Way Rolling Acres, Whitby, Durham, ON MLS® E13546284

Residential Freehold (Att/Row/Townhouse)

$795900.0

Price drop by 6.3%

4 Beds
4 Baths
2000-2500 sq-ft

Welcome to 19 Lively Way stunning Nordic-inspired freehold townhome by Acorn Developments, ideally situated in the heart of Whitby! This bright and sp

38 Photos

104 Fencerow Drive, Durham, ON , MLS #E13803194 , Image - 1

104 Fencerow Drive Rolling Acres, Whitby, Durham, ON MLS® E13803194

Residential Freehold (Detached)

$1129900.0

4 Beds
3 Baths
2500-3000 sq-ft

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

50 Photos

82 Bridlewood Boulevard, Durham, ON , MLS #E13710964 , Image - 1

82 Bridlewood Boulevard Rolling Acres, Whitby, Durham, ON MLS® E13710964

Residential Freehold (Detached)

$1999000.0

4 +1 Beds
5 Baths
3000-3500 sq-ft

Welcome to 82 Bridlewood Boulevard, a stunning custom-built Delta-Rae home where luxury, craftsmanship, and design come together seamlessly. Offering

50 Photos

19 Wigston Court, Durham, ON , MLS #E13805512 , Image - 1

19 Wigston Court Rolling Acres, Whitby, Durham, ON MLS® E13805512

Residential Freehold (Detached)

$1149000.0

4 +1 Beds
4 Baths
2500-3000 sq-ft

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

Open House : Sat Sep 26, 01:00 PM to 04:00 PM

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41 Winterberry Drive, Durham, ON , MLS #E13767746 , Image - 1

41 Winterberry Drive Rolling Acres, Whitby, Durham, ON MLS® E13767746

Residential Freehold (Detached)

$949900.0

Price drop by 2.6%

4 Beds
3 Baths
2000-2500 sq-ft

Welcome to 41 Winterberry, a beautifully maintained all-brick two-storey home situated in the highly desirable Rolling Acres neighbourhood. Offering a

48 Photos

29 Stratton Crescent, Durham, ON , MLS #E13796176 , Image - 1

29 Stratton Crescent Rolling Acres, Whitby, Durham, ON MLS® E13796176

Residential Freehold (Detached)

$1099000.0

4 +1 Beds
4 Baths
2500-3000 sq-ft

Offering more than 3,500 sq. ft. of finished living space, this beautifully cared-for home delivers the space, comfort and flexibility today's familie

41 Photos

16 Morningstar Avenue, Durham, ON , MLS #E13587842 , Image - 1

16 Morningstar Avenue Rolling Acres, Whitby, Durham, ON MLS® E13587842

Residential Freehold (Detached)

$1200000.0

Price drop by 4.0%

4 +1 Beds
4 Baths
1500-2000 sq-ft

4 Year New House Offered At Unbeatable Value, Location, And Income Potential For Families From Ajax And Durham Region. This Home Offers A Large 2-Stor

40 Photos

157 Waller Street, Durham, ON , MLS #E13789200 , Image - 1

157 Waller Street Rolling Acres, Whitby, Durham, ON MLS® E13789200

Residential Freehold (Detached)

$999000.0

4 +2 Beds
4 Baths
2000-2500 sq-ft

BRIGHT & BEAUTIFULLY RENOVATED 4+2 BED, 4-BATH FAMILY HOME WITH LEGAL BASEMENT APARTMENT IN HIGHLY DESIRABLE ROLLING ACRES! Extensively upgraded throu

Open House : Sun Sep 27, 01:00 PM to 04:00 PM

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17 CHATTERSON Street, Durham, ON , MLS #E13788698 , Image - 1

17 CHATTERSON Street Rolling Acres, Whitby, Durham, ON MLS® E13788698

Residential Freehold (Detached)

$995000.0

3 +1 Beds
3 Baths
2000-2500 sq-ft

Welcome to 17 Chatterson St in the desirable community of Rolling Acres! RECENTLY UPGRADED HOME. All brick, 2008 built and impeccably maintained singl

39 Photos

31 Thames Drive N, Durham, ON , MLS #E13763232 , Image - 1

31 Thames Drive N Rolling Acres, Whitby, Durham, ON MLS® E13763232

Residential Freehold (Detached)

$719999.0

2 +2 Beds
2 Baths
700-1100 sq-ft

This beautifully maintained 2+2 bedroom, 2 bathroom with finished basement with large rec room this home offers the perfect blend of comfort, space, a

34 Photos

1906 Rossland Road E, Durham, ON , MLS #E13769596 , Image - 1

1906 Rossland Road E Rolling Acres, Whitby, Durham, ON MLS® E13769596

Residential Freehold (Detached)

$1195000.0

3 +1 Beds
2 Baths
700-1100 sq-ft

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

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1910 Rossland Road E, Durham, ON , MLS #E13769594 , Image - 1

1910 Rossland Road E Rolling Acres, Whitby, Durham, ON MLS® E13769594

Residential Freehold (Detached)

$1195000.0

3 +1 Beds
2 Baths
1100-1500 sq-ft

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

40 Photos

39 Mcivor Street, Durham, ON , MLS #E13759274 , Image - 1

39 Mcivor Street Rolling Acres, Whitby, Durham, ON MLS® E13759274

Residential Freehold (Detached)

$949900.0

4 Beds
3 Baths
2000-2500 sq-ft

Welcome to this stunning all brick 4 bedroom home in a prime North Whitby location! The inviting, spacious foyer offers convenient access to the mai

40 Photos

25 Bedell Crescent, Durham, ON , MLS #E13646362 , Image - 1

25 Bedell Crescent Rolling Acres, Whitby, Durham, ON MLS® E13646362

Residential Freehold (Detached)

$799000.0

3 +1 Beds
2 Baths
700-1100 sq-ft

Over 2,000 square feet of living space. Welcome to 25 Bedell Crescent, Whitby: A Perfect Blend of Comfort, Style, and Space! Nestled on a quiet, famil

38 Photos

63 Eric Clarke Drive, Durham, ON , MLS #E13697702 , Image - 1

63 Eric Clarke Drive Rolling Acres, Whitby, Durham, ON MLS® E13697702

Residential Freehold (Detached)

$1029000.0

4 +1 Beds
4 Baths
2000-2500 sq-ft

Welcome to a home where everyday comfort meets effortless entertaining. Situated on a beautiful corner lot in a sought-after Whitby neighbourhood, thi

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