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

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With Square Yards Canada, you can find your dream luxury homes for sale in Rural Whitchurch-Stouffville. Explore your options from condo apartments, condo townhouses, detached houses, semi detached homes posted by agencies/owners who provide spacious and luxurious amenities in luxury houses for sale in Rural Whitchurch-Stouffville

Last Updated: August 14, 2026

49 Photos

38 Lakeview Avenue, York, ON , MLS #N13219822 , Image - 1

38 Lakeview Avenue Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13219822

Residential Freehold (Detached)

$2188000.0

1 +2 Beds
2 Baths
1500-2000 sq-ft

Welcome To Prestigious & Quiet Preston Lake! Direct Waterfront On A 75X241 Lot Just 35 Mins From Downtown Toronto. This Is Your Opportunity To Secure

36 Photos

38 Hill Country Drive, York, ON , MLS #N13661700 , Image - 1

38 Hill Country Drive Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13661700

Residential Freehold (Detached)

$2699888.0

5 Beds
5 Baths
5000 + sq-ft

Luxury estate living on exclusive Hill Country Drive. Situated on 1.877 acres with private long drive and 4 car garage surrounded by forest. This 5 be

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9 Emerald Heights Drive, York, ON , MLS #N13634594 , Image - 1

9 Emerald Heights Drive Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13634594

Residential Freehold (Detached)

$2099000.0

3 Beds
3 Baths
3000-3500 sq-ft

Stunning and Rarely Found 3-Car Garage BUNGALOW situated on an Ultra premium 85' Lot Backing onto One of the Top-rated & Private Emerald Hills Golf Co

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9 Island Lake Drive, York, ON , MLS #N13596018 , Image - 1

9 Island Lake Drive Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13596018

Residential Freehold (Detached)

$2148000.0

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

Rare lakefront Custom Built House on a approx. 1.51 acres Estate Lot with direct waterfront, 3-car garage with 12 parking, in a private, exclusive com

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46 Sawmill Lane, York, ON , MLS #N13660518 , Image - 1

46 Sawmill Lane Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13660518

Residential Freehold (Detached)

$2480000.0

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

Welcome to your own private nature retreat - an exceptional 12-acre property where timeless elegance meets the beauty of the outdoors.At the heart of

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111 Lake Woods Drive, York, ON , MLS #N13643798 , Image - 1

111 Lake Woods Drive Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13643798

Residential Freehold (Detached)

$4250000.0

5 +5 Beds
10 Baths
5000 + sq-ft

Welcome to one of Whitchurch-Stouffville's most exceptional luxury estates, where timeless elegance meets modern family living. Situated on approximat

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55 Ogden Crescent, York, ON , MLS #N13652812 , Image - 1

55 Ogden Crescent Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13652812

Residential Freehold (Detached)

$2100000.0

3 Beds
4 Baths
2500-3000 sq-ft

55 OGDEN CRESCENT CUSTOM ESTATE BUNGALOW | APPROX. 2 ACRES | 3-CAR GARAGE | ESTABLISHED ESTATE COMMUNITY [HOUSE] Beautifully maintained custom stone a

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18 Mccowan Lane, York, ON , MLS #N13578848 , Image - 1

18 Mccowan Lane Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13578848

Residential Freehold (Detached)

$2990000.0

4 +3 Beds
6 Baths
5000 + sq-ft

Welcome to your private 2-acre sanctuary at 18 McCowan Lane, where peaceful country living meets everyday convenience. Set against a beautiful, scenic

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3957 Bethesda Road, York, ON , MLS #N13436114 , Image - 1

3957 Bethesda Road Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13436114

Residential Freehold (Detached)

$4511000.0

Price drop by 4.0%

5 Beds
6 Baths
5000 + sq-ft

Welcome To This Rare Find 10-acre Estate Surrounded By Mature Trees And Park-like Views. This Custom-Built 5 Bedroom Bungalow Offers Over 5,000 sqft O

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2 Earl Cook Drive, York, ON , MLS #N13655422 , Image - 1

2 Earl Cook Drive Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13655422

Residential Freehold (Detached)

$3290000.0

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

Welcome To This Architecturally Stunning Estate, Ideally Situated On A Premium Quiet Cul-De-Sac. Exceptional Living On A Sprawling 2-Acre Lot Backing

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14547 Highway 48 N/A, York, ON , MLS #N12966958 , Image - 1

14547 Highway 48 N/A Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N12966958

Residential Freehold (Detached)

$4500000.0

2 Beds
1 Baths
< 700 sq-ft

Excellent opportunity to acquire approximately 93 acres of prime real estate situated along the highly trafficked Highway 48 in Stouffville. The prope

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13695 Kennedy Road, York, ON

13695 Kennedy Road Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13647716

Residential Freehold (Detached)

$3890000.0

3 Beds
1 Baths
1100-1500 sq-ft

Client Remarks Incredible 25 acre parcel of land with two 2 Houses On Property Plus Huge Barn at Corner Of Kennedy And Bloomington. Close to major hig

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14597 Woodbine Avenue, York, ON , MLS #N13219092 , Image - 1

14597 Woodbine Avenue Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13219092

Residential Freehold (Detached)

$2998000.0

4 +3 Beds
9 Baths
3500-5000 sq-ft

Discover unparalleled luxury in this fully custom-built 3 garage masterpiece estate home nestled in the heart of Stouffville. This stunning home sits

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2 Heron Trail, York, ON , MLS #N13637638 , Image - 1

2 Heron Trail Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13637638

Residential Freehold (Detached)

$2675000.0

4 Beds
6 Baths
3500-5000 sq-ft

Welcome to this exquisite home in the prestigious Trail of the Woods community of multi-million dollar grand estate homes, sitting on 1.7 acres of qui

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3404 Vivian Road, York, ON , MLS #N13628134 , Image - 1

3404 Vivian Road Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13628134

Residential Freehold (Detached)

$4199000.0

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

What if home wasn't simply where you lived, but where you reconnected, recharged, and found space to breathe? Set behind a private gated entrance on 2

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17236 Kennedy Road, York, ON , MLS #N13618960 , Image - 1

17236 Kennedy Road Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13618960

Residential Freehold (Vacant Land)

$4100000.0

An Outstanding Opportunity To Own Over 50 Acres In The Prime Location Of Whitchurch-Stouffville! Discover the endless potential of this 51.65 acre par

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1 Foxlair Court, York, ON , MLS #N13627988 , Image - 1

1 Foxlair Court Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13627988

Residential Freehold (Detached)

$2599000.0

6 +1 Beds
5 Baths
3500-5000 sq-ft

Welcome to 1 Foxlair Court! A Beautifully Updated Home Nestled on Nearly 1.5 Acres on a Quiet Cul-de-sac in the Prestigious Trail of the Woods Communi

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19 Wolf Run Court, York, ON , MLS #N13627330 , Image - 1

19 Wolf Run Court Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13627330

Residential Freehold (Detached)

$4989000.0

4 +1 Beds
5 Baths
5000 + sq-ft

Stunning 7200Sf Luxurious Estate in The Prestige Trail of The Woods, Ultimate Luxury & Privacy, On A Quiet Cul-De-Sac, Top of The Hill, Surrounded By

34 Photos

2 Sam Davis Court, York, ON , MLS #N13627242 , Image - 1

2 Sam Davis Court Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13627242

Residential Freehold (Detached)

$2999888.0

6 +4 Beds
7 Baths
5000 + sq-ft

2 Sam Davis Court, Stouffville- A residence of extraordinary scale, elegance, and presence set on a rare 1.05-acre estate lot in one of Stouffville's

50 Photos

46 Lake Woods Drive, York, ON , MLS #N13622574 , Image - 1

46 Lake Woods Drive Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13622574

Residential Freehold (Detached)

$3188000.0

5 Beds
5 Baths
5000 + sq-ft

Elegant classic stone masterpiece mansion surrounded by beautiful thick private forest in the enchanted Woodlands of Camelot with private wooded trail

50 Photos

76 Cedar Ridge Road, York, ON , MLS #N13615968 , Image - 1

76 Cedar Ridge Road Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13615968

Residential Freehold (Detached)

$6995000.0

7 +3 Beds
14 Baths
5000 + sq-ft

Some homes are built. This one was composed. Bethesda Forest Estates is one of York Region's most distinguished custom estate enclaves -private conser

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43 Ogden Crescent, York, ON , MLS #N12939190 , Image - 1

43 Ogden Crescent Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N12939190

Residential Freehold (Detached)

$4450000.0

4 +1 Beds
8 Baths
5000 + sq-ft

Experience luxury living at this breathtaking modern estate on 2 acres! Portions of interior masterfully designed by award winning interior designer E

34 Photos

17 Sleepy Hollow Lane, York, ON , MLS #N13565328 , Image - 1

17 Sleepy Hollow Lane Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13565328

Residential Freehold (Detached)

$2449999.0

4 +2 Beds
4 Baths
3500-5000 sq-ft

Welcome to this exceptional, newly renovated executive residence in the prestigious community of Sleepy Hollow Estates. Perfectly situated on one of t

39 Photos

3141 Vivian Road, York, ON , MLS #N12973764 , Image - 1

3141 Vivian Road Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N12973764

Residential Freehold (Detached)

$5560000.0

5 +1 Beds
8 Baths
5000 + sq-ft

Seldom Find A 8 Year Old Prestigious Custom Built Home Nestled On Premium 30.42 Acre Treed & Wooded Ravine Lot! 2 Acre Private Spectacular Pond At Bac

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6 Stonegate Street, York, ON , MLS #N13517562 , Image - 1

6 Stonegate Street Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13517562

Residential Freehold (Detached)

$2348000.0

4 +2 Beds
5 Baths
3500-5000 sq-ft

Welcome to 6 Stonegate St - A home that instantly transports you to cottage country the moment you step into the backyard. Set on just under an acre o

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14467 Warden Avenue, York, ON , MLS #N13596034 , Image - 1

14467 Warden Avenue Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13596034

Residential Freehold (Detached)

$2590000.0

1500-2000 sq-ft

RARE 10-ACRE CORNER LOT W/ APPROVED PERMITS & DRAWINGS! Prime Estate Lot On Warden Ave (Between Bloomington & Vandorf), Directly Adjacent To Emerald H

50 Photos

28 Sam Davis Court, York, ON , MLS #N13419252 , Image - 1

28 Sam Davis Court Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13419252

Residential Freehold (Detached)

$3180000.0

Price drop by 6.1%

7 Beds
7 Baths
5000 + sq-ft

Welcome to an extraordinary estate residence where luxury, scale, and craftsmanship converge on a premium 1-acre lot in an exclusive court setting. Of

37 Photos

15 Skyridge Court, York, ON , MLS #N13091814 , Image - 1

15 Skyridge Court Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13091814

Residential Freehold (Detached)

$2550000.0

5 Beds
6 Baths
3500-5000 sq-ft

15 Skyridge Crt Offering 5 Acres | Approximately 7,000 Sq Ft Total | Mature Forest | Stream | & a Premium Location. Just Minutes from Highway 404, Top

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3228 Bloomington Road, York, ON , MLS #N13576782 , Image - 1

3228 Bloomington Road Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13576782

Residential Freehold (Farm)

$3800000.0

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

Incredible 25 acre parcel of land with stunning scenic views. Emerald Hills Golf Course to the North, beautiful equestrian centre to the East... and

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50 Maxson Lane, York, ON , MLS #N13580406 , Image - 1

50 Maxson Lane Rural Whitchurch-Stouffville, Whitchurch-Stouffville, York, ON MLS® N13580406

Residential Freehold (Detached)

$3250000.0

6 Beds
6 Baths
5000 + sq-ft

Welcome to 50 Maxson Lane, a spectacular 2024-built luxury estate situated on a premium end lot of just under one acre in one of Stouffville's most pr

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