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Rural Whitchurch-Stouffville, Whitchurch-Stouffville, ON Luxury Homes - P2

Showing results 31 - 60 of 62

Last Updated: August 14, 2026

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17 Connor Drive, York, ON , MLS #N13464930 , Image - 1

17 Connor Drive Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13464930

Residential Freehold (Detached)

$2580000.0

4 Beds
7 Baths
3500-5000 sq-ft

Set on an impressive 125-foot frontage lot, this exceptional waterfront residence is offered independently from the adjacent parcel, which is subject

2 Photos

5 SHERRICK Drive, York, ON , MLS #N12567782 , Image - 1

5 SHERRICK Drive Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N12567782

Residential Freehold (Detached)

$3000000.0

Price drop by 14.3%

5 +1 Beds
6 Baths
5000 + sq-ft

Discover an extraordinary living in the prestigious Bethesda Estate, a Billionaire's Row of south Stouffville bordering Richmond Hill. Renowned for it

1 Photos

3932 St John Side Road, York, ON

3932 St John Side Road Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13166192

Residential Freehold (Vacant Land)

$2250000.0

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45 Loggers Trail, York, ON , MLS #N13540932 , Image - 1

45 Loggers Trail Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13540932

Residential Freehold (Detached)

$3080000.0

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

Rare Modern French Luxury Bungalow Estate. A rare offering in today's market, this exceptional Modern French-inspired luxury bungalow redefines high-e

50 Photos

61 SHERRICK Drive, York, ON , MLS #N13518060 , Image - 1

61 SHERRICK Drive Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13518060

Residential Freehold (Detached)

$3228000.0

5 +1 Beds
7 Baths
3500-5000 sq-ft

Stunning ravine estate in prestigious Bethesda Estates! Situated on a beautifully landscaped 1.04-acre lot, this 5+1bedroom, 7-bathroom home offers ov

36 Photos

10 Earl Cook Drive, York, ON , MLS #N13520970 , Image - 1

10 Earl Cook Drive Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13520970

Residential Freehold (Detached)

$2499000.0

4 Beds
5 Baths
2500-3000 sq-ft

Beautifully Updated 4-Bedroom Stone & Brick Bungaloft on a Breathtaking 2-Acre Lot Offering Privacy, Space, & Beautifully Curated Outdoor Living While

41 Photos

11 Cranborne Chase, York, ON , MLS #N12953598 , Image - 1

11 Cranborne Chase Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N12953598

Residential Freehold (Detached)

$3588000.0

4 +1 Beds
5 Baths
3500-5000 sq-ft

A Rare Custom Built Bungalow Offering Over 8,000 Sqft of Finished Living Space On An Exceptional 1.8 Acre Court Lot With 241 Ft of Frontage!Privately

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14059 McCowan Road, York, ON , MLS #N13483784 , Image - 1

14059 McCowan Road Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13483784

Residential Freehold (Rural Residential)

$2299000.0

4 Beds
5 Baths
2000-2500 sq-ft

Come check out this fabulous offering of a two-storey home, set on a 7.5 acre property, ready for you to move right in and enjoy the peaceful and tran

48 Photos

17 Hill Top Trail, York, ON , MLS #N13496388 , Image - 1

17 Hill Top Trail Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13496388

Residential Freehold (Detached)

$2480000.0

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

Luxurious custom built bungalow on approximately 1.3 acre lot, approximately 5,000 sq.ft. of beautifully renovated living space including basement on

27 Photos

4143 Vivian Road, York, ON , MLS #N13494876 , Image - 1

4143 Vivian Road Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13494876

Residential Freehold (Detached)

$2595000.0

5 Beds
4 Baths
3500-5000 sq-ft

DESIGNER BARNDOMINIUM/BUNGALOFT * LEGAL EXECUTIVE LARGE 1 BDRM LOFT APARTMENT & 2 OFFICES WITH SEPARATE ENTRANCES * 4 STALL BARN Welcome to Willow Tr

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15502 York Durham Line, York, ON , MLS #N13245954 , Image - 1

15502 York Durham Line Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13245954

Residential Freehold (Detached)

$8999900.0

5 +2 Beds
10 Baths
5000 + sq-ft

Step into your private oasis - where design becomes art and every detail tells a story. Set in one of York Region's most coveted neighbourhoods, this

44 Photos

12068 Mccowan Road, York, ON , MLS #N13493434 , Image - 1

12068 Mccowan Road Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13493434

Residential Freehold (Detached)

$8888000.0

8 Beds
10 Baths
5000 + sq-ft

Iconic Masterpiece Ready for Your Vision. An extraordinary opportunity awaits on this sprawling 48.4-acre property to a partially built, 20,000 sq ft

31 Photos

15660 Kennedy Road, York, ON , MLS #N12987660 , Image - 1

15660 Kennedy Road Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N12987660

Residential Freehold (Detached)

$3450000.0

4 Beds
3 Baths
2000-2500 sq-ft

Welcome to 15660 Kennedy Rd - a breathtaking private 24-acre sanctuary of privacy and natural beauty. Rolling hills, mature forest, and a spectacular

50 Photos

4074 St. John's Side Road, York, ON , MLS #N13487596 , Image - 1

4074 St. John's Side Road Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13487596

Residential Freehold (Detached)

$2488888.0

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

Architect/Engineer custom built home on 10 forested acres with groomed trails, views in every direction & a quiet and highly desirable location on St.

33 Photos

4901 Vandorf Road W, York, ON , MLS #N12855240 , Image - 1

4901 Vandorf Road W Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N12855240

Residential Freehold (Farm)

$3988000.0

4 Beds
4 Baths
3000-3500 sq-ft

Set on a serene 25-Acre Equestrian Property, this Exceptional Estate Blends Country Privacy with Unbeatable Convenience-just 12 Minutes to Downtown St

50 Photos

6468 Bethesda Road E, York, ON , MLS #N13484580 , Image - 1

6468 Bethesda Road E Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13484580

Residential Freehold (Detached)

$8299000.0

4 +1 Beds
8 Baths
5000 + sq-ft

Experience Unparalleled Luxury In This Exceptional Custom Estate Set On A Gated 10-Acre Property. Thoughtfully Designed And Expertly Curated, This Stu

27 Photos

16 Lake Woods Drive, York, ON , MLS #N13471454 , Image - 1

16 Lake Woods Drive Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13471454

Residential Freehold (Detached)

$2988000.0

5 Beds
6 Baths
5000 + sq-ft

Custom Built Bungalow Loft in Prestigious Camelot Estates on a 2.12 Acre Lot, Beautifully Updated, Cobblestone Circular Driveway, Thousands Spent Desi

40 Photos

29 Moraine Forest Trail, York, ON , MLS #N13471280 , Image - 1

29 Moraine Forest Trail Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13471280

Residential Freehold (Detached)

$7980000.0

6 Beds
8 Baths
5000 + sq-ft

Wow, A Rare Gem In Moraine Forest Tr.*Newly Cstm-Reno'd Approx.13,500 SqFt.Lvg Spcs Incldg Fin.W/O Lwr Lvl,Top-Tier Lux.Hm Nstld On10+Acr Frst Lnd & S

3 Photos

13099 Kennedy Road, York, ON , MLS #N13470086 , Image - 1

13099 Kennedy Road Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13470086

Residential Freehold (Farm)

$2598000.0

3 Beds
2 Baths
1100-1500 sq-ft

Rare Opportunity To Own This Outstanding 10 Acre Land With Beautiful Pond Situated In The Heart of Stouffville . This Country Style Home With 3 Bedroo

33 Photos

16902 Mccowan Road, York, ON , MLS #N13241828 , Image - 1

16902 Mccowan Road Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13241828

Residential Freehold (Detached)

$3480000.0

3 Beds
2 Baths
1500-2000 sq-ft

A rare opportunity to create a true country estate on approximately 29 acres in a peaceful, established rural setting. Much of the property offers ope

37 Photos

69 Raeview Drive, York, ON , MLS #N13451486 , Image - 1

69 Raeview Drive Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13451486

Residential Freehold (Detached)

$2699000.0

5 +1 Beds
7 Baths
5000 + sq-ft

Experience resort-style living in prestigious Sleepy Hollow Estates. Situated on a private 1.07-acre cul-de-sac lot, this extensively renovated luxury

32 Photos

6 Kingstree Court, York, ON , MLS #N13423112 , Image - 1

6 Kingstree Court Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13423112

Residential Freehold (Detached)

$2198000.0

4 Beds
4 Baths
3000-3500 sq-ft

Welcome to this exceptional estate home in the prestigious Bloomington Woods community of Whitchurch-Stouffville, built by renowned builder Geranium H

26 Photos

13645 Ninth Line, York, ON , MLS #N13147146 , Image - 1

13645 Ninth Line Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13147146

Residential Freehold (Detached)

$5975000.0

Price drop by 0.0%

2 +2 Beds
2 Baths
2500-3000 sq-ft

Set on an impressive 8.08 acres in the prestigious and highly sought-after hamlet of Bloomington, this exceptional estate presents a rare blend of lux

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16718 Pleasantville Curve Court, York, ON , MLS #N13125436 , Image - 1

16718 Pleasantville Curve Court Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13125436

Residential Freehold (Vacant Land)

$2200000.0

Make this amazing Pleasantville is one of the most sought after Whitchurch-Stoufville location to build or own homes. Over 9 Acres Of Vacant Land To B

25 Photos

6523 Bloomington Road, York, ON , MLS #N11983951 , Image - 1

6523 Bloomington Road Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N11983951

Residential Freehold (Vacant Land)

$3799000.0

< 700 sq-ft

This VACANT Lot has 853 ft of premium wide frontage with incredible sunset views! This lot islocated in an area near many multi-million dollar Estates

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4971 Bloomington Road, York, ON , MLS #N13039970 , Image - 1

4971 Bloomington Road Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13039970

Residential Freehold (Farm)

$9988888.0

1500-2000 sq-ft

Exceptional 108 Acre Prime Farm Parcel in the Heart of Stouffville, Ideally Positioned at the High-Traffic Intersection of Bloomington Road and Highwa

27 Photos

8 Greenvalley Circle, York, ON , MLS #N13021860 , Image - 1

8 Greenvalley Circle Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13021860

Residential Freehold (Detached)

$2490000.0

5 +1 Beds
5 Baths
3500-5000 sq-ft

Lucky Number 8. 5000 sqft +Total Living Space. Exquisite Home In Prestigious Trail Of The Woods Siting On 1.4 Acre Of Private Land Overlooking Greener

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15672 Warden Avenue, York, ON , MLS #N12643350 , Image - 1

15672 Warden Avenue Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N12643350

Residential Freehold (Vacant Land)

$5550000.0

Price drop by 3.5%

Excellent opportunity to own 94 (Per MPAC) acres of serene land ideally located just minutes from Stouffville, Aurora, Markham, and Highway 404. This

43 Photos

3125 Vandorf Side Road, York, ON , MLS #N12956384 , Image - 1

3125 Vandorf Side Road Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N12956384

Residential Freehold (Farm)

$5500000.0

4 +3 Beds
4 Baths
2000-2500 sq-ft

Rare opportunity must see 10-acre lot of equestrian retreat in the heart of Whitchurch-Stouffville. Investors, family, equestrian enthusiates welcome!

38 Photos

13123 Mccowan Road, York, ON , MLS #N12951180 , Image - 1

13123 Mccowan Road Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N12951180

Residential Freehold (Detached)

$9990000.0

3 +2 Beds
4 Baths
3000-3500 sq-ft

A once-in-a-generation opportunity to own an extraordinary private estate in Rural Whitchurch-Stouffville, set on approximately 42.35 acres at McCowan

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