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Simcoe, ON Luxury Homes - P5

Showing results 121 - 145 of 145
Last Updated: December 24, 2025
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
  • Square Feet(Lo-Hi)
  • Square Feet(Hi-Lo)
50 Photos
Last Updated : 169 Days ago
91 Lakeshore Road W, Simcoe, ON , MLS #40721480 , Image - 1
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91 Lakeshore Road W Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40721480

Residential (Single Family Residence)

$2825000
price drop iconPrice drop by 3.4%
  • 4 Beds
  • 3 Baths
  • 3893 sq-ft
Immaculate once in a lifetime opportunity to be on Lake Simcoe's shores in this breathtaking ranch bungalow with bright walk-out lower level. With fo
17 Photos
Last Updated : 169 Days ago
7369 5th Sideroad Sideroad, Simcoe, ON , MLS #40714577 , Image - 1

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7369 5th Sideroad Sideroad Rural King, Essa, Simcoe, ON MLS® 40714577

Farm (Agriculture)

$2875000
price drop iconPrice drop by 17.7%
  • 5 Beds
  • 3 Baths
  • 2610 sq-ft
This property offers a prime location, immediately abutting the border of New Tecumseth, with two road frontages for easy access. The 2610 sq. ft. far
17 Photos
Last Updated : 169 Days ago
7369 5th Sideroad Side Road, Simcoe, ON , MLS #40714562 , Image - 1

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7369 5th Sideroad Side Road Rural King, Essa, Simcoe, ON MLS® 40714562

Land (Residential)

$2875000
price drop iconPrice drop by 17.7%
This property offers a prime location, immediately abutting the border of New Tecumseth, with two road frontages for easy access. The 2610 sq. ft. far
41 Photos
Last Updated : 169 Days ago
376 Brewery Lane, Simcoe, ON , MLS #40710630 , Image - 1

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376 Brewery Lane Orillia, Simcoe, ON MLS® 40710630

Residential (Single Family Residence)

$4799000
  • 5 Beds
  • 5 Baths
  • 5393 sq-ft
Welcome to 376 Brewery Lane, a stunning luxury waterfront home situated on one of Orillia’s finest streets. This exceptional property offers 104 feet
Pre-Construction
Rosehaven Simcoe Woods
6 Photos

Rosehaven Simcoe Woods

Innisfil Beach Road & Webster Boulevard
From $879,990 - $1,339,990
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Project Info
  • Units
  • Townhouses
building outline
Property Mix
Floorplans coming soon
Developer:Rosehaven Homes
48 Photos
Last Updated : 169 Days ago
6409 10th Line, Simcoe, ON , MLS #40702268 , Image - 1

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6409 10th Line Rural King, Essa, Simcoe, ON MLS® 40702268

Farm (Agriculture)

$3250000
  • 4 Beds
  • 2 Baths
  • 1869 sq-ft
100 acre Farm for sale / 80 acres of workable land. Cash crop and livestock opportunities. Nicely maintained 4 bedroom, 2 bathroom farmhouse. Huge kit
44 Photos
Last Updated : 169 Days ago
1775 9th Line, Simcoe, ON , MLS #40700578 , Image - 1

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1775 9th Line Rural Innisfil, Innisfil, Simcoe, ON MLS® 40700578

Residential (Single Family Residence)

$2198000
price drop iconPrice drop by 4.4%
  • 5 Beds
  • 4 Baths
  • 5681 sq-ft
Experience the perfect blend of luxury and location in this extraordinary 5-bedroom, 4-bathroom estate, offering approximately 5,681 square feet of ex
12 Photos
Last Updated : 169 Days ago
7089 5th Sideroad, Simcoe, ON , MLS #40700033 , Image - 1

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7089 5th Sideroad Rural Innisfil, Innisfil, Simcoe, ON MLS® 40700033

Residential (Single Family Residence)

$6750000
  • 4 Beds
  • 2 Baths
  • 3215 sq-ft
A Rare Opportunity in Coveted Innisfil! Seize this exceptional chance to own 8.36 acres of prime real estate in one of Ontario’s fastest-growing hotsp
20 Photos
Last Updated : 169 Days ago
1536 Tiny Beaches Road N, Simcoe, ON , MLS #40685833 , Image - 1

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1536 Tiny Beaches Road N Rural Tiny, Tiny, Simcoe, ON MLS® 40685833

Residential (Single Family Residence)

$3399000
  • 4 Beds
  • 1 Baths
  • 950 sq-ft
For more information, please click Brochure button. Your opportunity to own an awesome four season waterfront beach house with 102 feet of sandy shore
18 Photos
Last Updated : 169 Days ago
LOT 39 Friesian Court, Simcoe, ON , MLS #40639068 , Image - 1

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LOT 39 Friesian Court Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® 40639068

Residential (Single Family Residence)

$2073900
  • 4 Beds
  • 4 Baths
  • 4291 sq-ft
Customized builder home under construction. ACT NOW! You still have time to choose all of your interior colours and materials. This home incorporates
43 Photos
Last Updated : 309 Days ago
2710 Nottawasaga Concession 10 N, Simcoe, ON , MLS #40653337 , Image - 1

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2710 Nottawasaga Concession 10 N Rural Clearview, Clearview, Simcoe, ON MLS® 40653337

Residential (Single Family Residence)

$4750000
price drop iconPrice drop by 4.0%
  • 6 Beds
  • 5 Baths
  • 5321 sq-ft
Introducing Winterbrook, your year-round retreat nestled in the heart of nature! First time to market, this chalet boasts an expansive layout that eff
48 Photos
Last Updated : 310 Days ago
668 Broadview Avenue, Simcoe, ON , MLS #40698592 , Image - 1

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668 Broadview Avenue Orillia, Simcoe, ON MLS® 40698592

Residential (Single Family Residence)

$2495000
  • 5 Beds
  • 4 Baths
  • 2596 sq-ft
Welcome to this exquisite, professionally renovated waterfront property on Orillia's highly sought-after Couchiching Point. Sitting along the pristine
46 Photos
Last Updated : 331 Days ago
6 Thicketwood Place, Simcoe, ON , MLS #40662100 , Image - 1

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6 Thicketwood Place Rural Ramara, Ramara, Simcoe, ON MLS® 40662100

Residential (Single Family Residence)

$2098000
  • 6 Beds
  • 1 Baths
  • 4144 sq-ft
Luxurious Lake Side Living At Its Finest. From The Moment You Enter This Spectacular Home, You Are Greeted By Stunning Views of Beautiful Lake Simcoe.
40 Photos
Last Updated : 338 Days ago
3298 Seydel Lane Lane, Simcoe, ON , MLS #40678691 , Image - 1

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3298 Seydel Lane Lane Rural Severn, Severn, Simcoe, ON MLS® 40678691

Residential (Single Family Residence)

$4295000
  • 5 Beds
  • 4 Baths
  • 3200 sq-ft
Located on the serene Gloucester Pool, this rare beauty is a stunning waterfront home. Featuring 4 bedrooms and 4 bathrooms, it boasts 337 feet of wat
50 Photos
Last Updated : 351 Days ago
1428 10 Nottawasaga Concession N, Simcoe, ON , MLS #40662574 , Image - 1

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1428 10 Nottawasaga Concession N Rural Clearview, Clearview, Simcoe, ON MLS® 40662574

Residential (Single Family Residence)

$4950000
  • 6 Beds
  • 5 Baths
  • 6609 sq-ft
Spectacular 37.4-Acre Luxury Estate with Breathtaking Georgian Bay Views. Nestled in the heart of nature, just minutes from Collingwood and Blue Mount
45 Photos
Last Updated : 393 Days ago
49 Sydenham Trail W, Simcoe, ON , MLS #40679451 , Image - 1

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49 Sydenham Trail W Rural Clearview, Clearview, Simcoe, ON MLS® 40679451

Residential (Single Family Residence)

$2399900
  • 5 Beds
  • 4 Baths
  • 3701 sq-ft
This immaculate custom-built residence is situated amidst 2.5 acres of lush, mature trees. Set on a rolling landscape, this remarkable home showcases
37 Photos
Last Updated : 394 Days ago
874 Tiny Beaches Road S, Simcoe, ON , MLS #40655289 , Image - 1

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874 Tiny Beaches Road S Rural Tiny, Tiny, Simcoe, ON MLS® 40655289

Residential (Single Family Residence)

$2500000
  • 3 Beds
  • 2 Baths
  • 1382 sq-ft
Owned by the same family since 1949, this beachfront cottage and cabin are being offered for sale for the first time in 75 years. Located 90 minutes
36 Photos
Last Updated : 398 Days ago
53 Niagara Street, Simcoe, ON , MLS #40661720 , Image - 1

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53 Niagara Street Collingwood, Simcoe, ON MLS® 40661720

Residential (Single Family Residence)

$2649000
  • 5 Beds
  • 4 Baths
  • 3700 sq-ft
Discover the ultimate in luxury and location with this stunning custom-built 5-bedroom VanderMeer home, just steps from the pristine shores of Georgia
50 Photos
Last Updated : 402 Days ago
1400 Chemin Du Loup Road, Simcoe, ON , MLS #40668549 , Image - 1

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1400 Chemin Du Loup Road Rural Tiny, Tiny, Simcoe, ON MLS® 40668549

Residential (Single Family Residence)

$2299000
  • 3 Beds
  • 3 Baths
  • 5267 sq-ft
An artistic masterpiece of design. Welcome to this extraordinary 48.9-acre estate, where luxury, adventure, and endless opportunity await! This 5,000+
49 Photos
Last Updated : 404 Days ago
3476 Garden Of Eden Road, Simcoe, ON , MLS #40667043 , Image - 1

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3476 Garden Of Eden Road Rural Clearview, Clearview, Simcoe, ON MLS® 40667043

Residential (Single Family Residence)

$4499999
  • 7 Beds
  • 8 Baths
  • 7745 sq-ft
Nestled in the heart of the Niagara escarpment on the esteemed summer road of Garden of Eden Creemore, You will find this exclusive seven bedroom& eig
20 Photos
Last Updated : 404 Days ago
1148 Concession 6 South Nottawasaga, Simcoe, ON , MLS #40671364 , Image - 1

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1148 Concession 6 South Nottawasaga Rural Clearview, Clearview, Simcoe, ON MLS® 40671364

Farm (Agricultural No Res)

$3599000
  • 0 sq-ft
Embrace the potential of this extraordinary 180+ acre property, perfect for creating a luxurious estate or serene weekend retreat. Nestled amidst scen
18 Photos
Last Updated : 408 Days ago
3869 7th Line, Simcoe, ON , MLS #40675056 , Image - 1

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3869 7th Line Rural Innisfil, Innisfil, Simcoe, ON MLS® 40675056

Farm (Agriculture)

$4888000
  • 4 Beds
  • 3 Baths
  • 2693 sq-ft
Located close to new developments in the rapidly expanding South Barrie area and minutes from a new major commercial warehouse, this agriculture zoned
30 Photos
Last Updated : 410 Days ago
15 Northwood Drive, Simcoe, ON , MLS #40669970 , Image - 1

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15 Northwood Drive Rural Clearview, Clearview, Simcoe, ON MLS® 40669970

Residential (Single Family Residence)

$2899000
  • 4 Beds
  • 4 Baths
  • 3383 sq-ft
Welcome to Pineapple Hill - a home built for active lifestyles in one of the most highly sought after neighborhoods.Drive down the private laneway to
20 Photos
Last Updated : 419 Days ago
1148 Concession 6 South Nottawasaga, Simcoe, ON , MLS #40671284 , Image - 1

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1148 Concession 6 South Nottawasaga Rural Clearview, Clearview, Simcoe, ON MLS® 40671284

Land (Residential)

$3599000
Embrace the potential of this extraordinary 180+ acre property, perfect for creating a luxurious estate or serene weekend retreat. Nestled amidst scen
50 Photos
Last Updated : 438 Days ago
7781 Poplar Sideroad, Simcoe, ON , MLS #40649180 , Image - 1

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7781 Poplar Sideroad Rural Clearview, Clearview, Simcoe, ON MLS® 40649180

Residential (Single Family Residence)

$6499000
  • 5 Beds
  • 7 Baths
  • 12111 sq-ft
Welcome to one of the most spectacular properties you will find located on the Clearview/Collingwood border just 2hrs from Toronto and located minutes
11 Photos
Last Updated : 454 Days ago
1081 Anderson Line, Simcoe, ON , MLS #40638464 , Image - 1

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1081 Anderson Line Rural Severn, Severn, Simcoe, ON MLS® 40638464

Land (Commercial)

$4999000
ATTENTION DEVELOPERS AND INVESTORS 51 Acres Land of Prime Residential Development Land. Property is Recently Designated in The Settlement Area of Col
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