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Bradford West Gwillimbury, ON Luxury Homes

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With Square Yards Canada, you can find your dream luxury homes for sale in Bradford West Gwillimbury. 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 Bradford West Gwillimbury

Last Updated: August 13, 2026

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245 Pine Hill Road, Simcoe, ON , MLS #N13615814 , Image - 1

245 Pine Hill Road Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13615814

Residential Freehold (Detached)

$2480000.0

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

A rare opportunity to own a luxury estate on one of Bradford's most desirable executive streets. Situated on a premium 1.66-acre pie-shaped lot, this

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102 Pine Hill Road, Simcoe, ON , MLS #N13427258 , Image - 1

102 Pine Hill Road Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13427258

Residential Freehold (Detached)

$2689000.0

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

Set Within The Prestigious Shires Estates Community, This Impressive All-Brick Country Residence Is Surrounded By 2.33 Acres Of Scenic Privacy With Ma

40 Photos

2 Dale Crescent, Simcoe, ON , MLS #N13596444 , Image - 1

2 Dale Crescent Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13596444

Residential Freehold (Detached)

$2199999.0

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

A Custom-Built Bungalow On 1 Acre, Complete With A Heated Saltwater Pool, Over 3,000 Sq Ft Of Main-Floor Living, And A Finished Basement With Two Stai

Open House : Sun Aug 16, 01:00 PM to 03:00 PM

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4421 5th Line N/A, Simcoe, ON , MLS #N13661380 , Image - 1

4421 5th Line N/A Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13661380

Residential Freehold (Detached)

$2258888.0

4 Beds
3 Baths
3500-5000 sq-ft

Truly a one of a kind property - The Carswell House is a remarkable Georgian-style home with immense history and character. Built circa 1840's by one

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2280 Simcoe County Road 27 N/A, Simcoe, ON , MLS #N13479332 , Image - 1

2280 Simcoe County Road 27 N/A Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13479332

Residential Freehold (Detached)

$3899999.0

4 +2 Beds
5 Baths
5000 + sq-ft

Welcome To 2280 Hwy 27 Bradford. A Private Luxury Retreat On 10 Acre Land With 7500 Sqft Of Living Space. Detached 6 Bedroom House, 5 Washrooms, Finis

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3591 Line 12 N/A, Simcoe, ON , MLS #N13089012 , Image - 1

3591 Line 12 N/A Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13089012

Residential Freehold (Farm)

$2999000.0

3 Beds
2 Baths
2000-2500 sq-ft

Rare Opportunity To Own An Extraordinary 26+ Acre Horse Farm Featuring Two Fully Independent Residences In Highly Desirable Bradford West Gwillimbury.

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4495 Line 11 N/A, Simcoe, ON , MLS #N12836026 , Image - 1

4495 Line 11 N/A Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N12836026

Residential Freehold (Farm)

$7995000.0

2 Beds
3 Baths
1500-2000 sq-ft

Located just north of Bond Head and offering prime exposure by its dual frontage along Highway 27 and Line 11. Outstanding 159.67-acre farm situated w

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3162 Line 12 N/A, Simcoe, ON , MLS #N12441196 , Image - 1

3162 Line 12 N/A Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N12441196

Residential Freehold (Detached)

$3999000.0

Price drop by 4.8%

4 Beds
3 Baths
2500-3000 sq-ft

Why Drive To The Cottage When You Can Live at Your Own Private Retreat With Spring Fed Pond On 43 Acres. This Absolutely Unique Country Estate is In T

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270 Walker Avenue, Simcoe, ON , MLS #N13646980 , Image - 1

270 Walker Avenue Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13646980

Residential Freehold (Detached)

$3000000.0

3 Beds
1 Baths
1100-1500 sq-ft

Exceptional investment opportunity in the heart of Bradford! This remarkable 1.189-acre property features three distinct lots, including two clear par

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168 Pine Hill Road, Simcoe, ON , MLS #N13557218 , Image - 1

168 Pine Hill Road Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13557218

Residential Freehold (Detached)

$2348000.0

4 Beds
3 Baths
3000-3500 sq-ft

Welcome to 168 Pine Hill Road, an extraordinary executive estate nestled on a breathtaking 1.38 acre private lot in one of Bradford's most prestigious

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2166 10th Side Road, Simcoe, ON , MLS #N13527220 , Image - 1

2166 10th Side Road Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13527220

Residential Freehold (Detached)

$3368800.0

6 +1 Beds
9 Baths
5000 + sq-ft

Generational Living at it's finest in Bradford's exclusive area. 2min to HWY 400. Feel the magnificence of this one of a kind property the second you

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331 Tornado Drive, Simcoe, ON , MLS #N12106179 , Image - 1

331 Tornado Drive Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N12106179

Residential Freehold (Farm)

$2900000.0

Price drop by 3.3%

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

Welcome to 331 Tornado Dr, Nestled in the Quiet Farming Community of Bradford West Gwillimbury. This residential farmland is a terrific opportunity fo

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4227 5 Line, Simcoe, ON , MLS #N13495092 , Image - 1

4227 5 Line Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13495092

Residential Freehold (Vacant Land)

$8999999.0

1500-2000 sq-ft

This 53 acre parcel is located close to Hwy 400 southbound between Highways 88 & 89 offering an exceptional chance to build your own vision. Located

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4268 Sideroad 5 Line S, Simcoe, ON , MLS #N13495076 , Image - 1

4268 Sideroad 5 Line S Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13495076

Residential Freehold (Vacant Land)

$11500000.0

Whether you're looking for a peaceful retreat, a development opportunity, or a long-term investment, this land is ready for your plans.102.93 acres of

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197 Nottingham Forest Road, Simcoe, ON , MLS #N13210752 , Image - 1

197 Nottingham Forest Road Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13210752

Residential Freehold (Detached)

$3199000.0

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

Discover unparalleled estate living in this magnificent executive residence, gracefully positioned on a commanding 1.14-acre lot in the prestigious Sh

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29 W Dykie Court, Simcoe, ON , MLS #N13086544 , Image - 1

29 W Dykie Court Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13086544

Residential Freehold (Detached)

$2250000.0

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

*Welcome To 29 W Dykie Court* Newly Built Custom Designed Home In Desirable Court Location* High Quality Custom Designer Finishes Throughout* Bright A

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84 Simcoe Road, Simcoe, ON , MLS #N12889150 , Image - 1

84 Simcoe Road Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N12889150

Residential Freehold (Vacant Land)

$2988000.0

Prime development opportunity in the rapidly growing community of Bradford West Gwillimbury. Approximately 0.82 acres (35,640 sq. ft.) ideally located

11 Photos

3568 4 Line, Simcoe, ON , MLS #N12641382 , Image - 1

3568 4 Line Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N12641382

Residential Freehold (Vacant Land)

$3500000.0

Are you ready to turn your real estate dreams into reality? Presenting a golden opportunity for savvy investors - a sprawling piece of vacant land nes

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Bradford West Gwillimbury, ON Luxury Homes

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