218+ 5 Bedroom Houses Sale for Simcoe in Under $10M

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24 Brentwood Road, Simcoe, ON , MLS #N13482862 , Image - 1

24 Brentwood Road Angus, Essa, Simcoe, ON MLS® N13482862

Residential Freehold (Triplex)

$649000.0

5 Beds
4 Baths
2000-2500 sq-ft

Exceptional Investment Opportunity in Angus! Rare legal triplex offering strong income potential and exceptional versatility. This property features o

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17 Sanford Circle, Simcoe, ON , MLS #S12975748 , Image - 1

17 Sanford Circle Centre Vespra, Springwater, Simcoe, ON MLS® S12975748

Residential Freehold (Detached)

$1374900.0

5 Beds
4 Baths
3500-5000 sq-ft

Experience the pinnacle of turnkey luxury in this immaculate 3,945 sq. ft. Lilac model by Yorkwood Homes (2023). Situated on a premium lot in the pres

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22 Caroline Street, Simcoe, ON , MLS #S13494256 , Image - 1

22 Caroline Street Allandale Centre, Barrie, Simcoe, ON MLS® S13494256

Residential Freehold (Detached)

$1249900.0

5 Beds
4 Baths
2000-2500 sq-ft

Prime Land Assembly Development in Barrie. Offering two contiguous properties 22 & 26 Caroline Street totaling approx. 25,700 Square Feet of Land. Ind

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2032 Lakeshore Drive, Simcoe, ON , MLS #S13493972 , Image - 1

2032 Lakeshore Drive Rural Ramara, Ramara, Simcoe, ON MLS® S13493972

Residential Freehold (Detached)

$1598000.0

5 Beds
4 Baths
2000-2500 sq-ft

Spectacular Family Cottage with 78ft of Perfect West Facing Lake Simcoe Shoreline. Just a One Hour Drive From the Eastern End of the GTA. The Cottage

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238 Sixth Street, Simcoe, ON , MLS #S13487250 , Image - 1

238 Sixth Street Midland, Simcoe, ON MLS® S13487250

Residential Freehold (Detached)

$699900.0

5 Beds
3 Baths
2000-2500 sq-ft

Step into the timeless charm of this beautifully maintained century home, offering the perfect blend of character, comfort, and versatility. Lovingly

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995611 Mono-Adjala Townline N/A, Simcoe, ON , MLS #N13472276 , Image - 1

995611 Mono-Adjala Townline N/A Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N13472276

Residential Freehold (Detached)

$7250000.0

5 +1 Beds
6 Baths
5000 + sq-ft

Set amid 97+ acres of rolling countryside, forests, ponds and productive farmland, Pond Hill Farm is a rare legacy estate where heritage architecture,

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4 Woodview Drive, Simcoe, ON , MLS #S13476610 , Image - 1

4 Woodview Drive Rural Clearview, Clearview, Simcoe, ON MLS® S13476610

Residential Freehold (Detached)

$1995000.0

5 Beds
3 Baths
3000-3500 sq-ft

Welcome to 4 Woodview Drive in the highly sought-after Collingwoodlands community. Extensively renovated between 2023 and 2024 with approximately $400

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8418 Tosorontio 20th Side Road, Simcoe, ON , MLS #N13483456 , Image - 1

8418 Tosorontio 20th Side Road Lisle, Adjala-Tosorontio, Simcoe, ON MLS® N13483456

Residential Freehold (Detached)

$2888000.0

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

Top 5 Reasons You Will Love This Home: 1) Remarkable custom estate set on nearly 50 acres of private wooded land, offering an exceptional sense of sec

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17 Staglir Drive, Simcoe, ON , MLS #S13481642 , Image - 1

17 Staglir Drive Rural Tiny, Tiny, Simcoe, ON MLS® S13481642

Residential Freehold (Detached)

$1290000.0

5 Beds
3 Baths
3000-3500 sq-ft

Modern Custom-Built Home (2025) Featuring Over 3,500 Sq. Ft. Of Total Luxury Living Space, This Home Includes 5 Spacious Bedrooms, 3 Full Bathrooms, H

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3778 Vasey Road, Simcoe, ON , MLS #S12826236 , Image - 1

3778 Vasey Road Rural Tay, Tay, Simcoe, ON MLS® S12826236

Residential Freehold (Detached)

$2599900.0

5 Beds
4 Baths
3500-5000 sq-ft

Quiet Luxury on 75 forested Acres in Tay. Long, paved, tree-lined winding driveway leads to this unique custom-built executive home, offering unmatche

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1688 Lakeshore Drive, Simcoe, ON , MLS #S13479230 , Image - 1

1688 Lakeshore Drive Rural Ramara, Ramara, Simcoe, ON MLS® S13479230

Residential Freehold (Detached)

$3999999.0

5 Beds
5 Baths
5000 + sq-ft

Welcome to 1688 Lakeshore, a spectacular custom-built waterfront estate set on an impressive 151'x 305' lot. Offering over 5,000 sq. ft. of beautifull

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11 Caldwell Drive, Simcoe, ON , MLS #S13475136 , Image - 1

11 Caldwell Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13475136

Residential Freehold (Detached)

$1799900.0

5 Beds
5 Baths
2500-3000 sq-ft

Brand new custom-built bungalow with 5,000 Sqft + living space offering elevated luxury, exceptional craftsmanship, and ultimate comfort on a sprawlin

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1250 Frankland Lane, Simcoe, ON , MLS #S13473724 , Image - 1

1250 Frankland Lane Rural Severn, Severn, Simcoe, ON MLS® S13473724

Residential Freehold (Detached)

$4699000.0

5 Beds
3 Baths
5000 + sq-ft

Top Reasons You Will Love This Home: Experience the epitome of lakeside living in this breathtaking 5,348 square foot waterfront estate, gracefully se

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10 Misty Court, Simcoe, ON , MLS #S13060582 , Image - 1

10 Misty Court Rural Ramara, Ramara, Simcoe, ON MLS® S13060582

Residential Freehold (Detached)

$2680000.0

Price drop by 7.2%

5 +0 Beds
5 Baths
3000-3500 sq-ft

Stunning Large Two-Storey Waterfront Family Home Located In Bayshore Village, A Unique, Friendly And Highly Sought-After Community On A School Bus Rou

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26 Cathedral Pines Road, Simcoe, ON , MLS #S13467448 , Image - 1

26 Cathedral Pines Road Horseshoe Valley, Oro-Medonte, Simcoe, ON MLS® S13467448

Residential Freehold (Detached)

$1349000.0

5 Beds
5 Baths
2500-3000 sq-ft

TIMELESS ESTATE-STYLE LIVING IN DISTINGUISHED CATHEDRAL PINES WITH NEARLY 2,900 SQ FT ON OVER HALF AN ACRE! Hidden behind a veil of mature evergreens

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203 Coates Drive, Simcoe, ON , MLS #S13467204 , Image - 1

203 Coates Drive Stayner, Clearview, Simcoe, ON MLS® S13467204

Residential Freehold (Detached)

$1687000.0

5 Beds
5 Baths
3500-5000 sq-ft

Welcome to 203 Coates Drive, a beautifully designed 5-bedroom, 4-bathroom home built in 2023 in one of Stayner's newest and most desirable neighbourho

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246 Mary Street, Simcoe, ON , MLS #S13115594 , Image - 1

246 Mary Street Orillia, Simcoe, ON MLS® S13115594

Residential Freehold (Detached)

$525000.0

Price drop by 9.5%

5 Beds
2 Baths
2000-2500 sq-ft

VERSATILE 2-STOREY HOME WITH TWO SELF-CONTAINED LIVING SPACES ON AN EXTRA-DEEP LOT IN THE HEART OF ORILLIA! Rarely offered and full of opportunity, th

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537 Ste Marie Street, Simcoe, ON , MLS #S13127624 , Image - 1

537 Ste Marie Street Collingwood, Simcoe, ON MLS® S13127624

Residential Freehold (Detached)

$699000.0

Price drop by 17.7%

5 Beds
2 Baths
1500-2000 sq-ft

UNIQUE OPPORTUNITY to purchase a delightful 3 Bedroom Victorian heritage property with wrap around porch and ample parking in an excellent location an

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896 Booth Avenue, Simcoe, ON , MLS #N13463956 , Image - 1

896 Booth Avenue Alcona, Innisfil, Simcoe, ON MLS® N13463956

Residential Freehold (Detached)

$1299000.0

5 +1 Beds
4 Baths
2500-3000 sq-ft

Welcome to this stunning 5-bedroom family home nestled in a sought-after neighbourhood just steps from the lake and nearby parks! Situated in a quiet,

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311 Tollendal Mill Road, Simcoe, ON , MLS #S13458972 , Image - 1

311 Tollendal Mill Road South Shore, Barrie, Simcoe, ON MLS® S13458972

Residential Freehold (Detached)

$1689000.0

5 Beds
3 Baths
3000-3500 sq-ft

A rare find within the City of Barrie - private, treed 1.23 acre lot, backing onto Lover's Creek, in the exclusive lakeside South Shore neighbourhood.

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795853 Grey 19 Road, Simcoe, ON , MLS #S13452012 , Image - 1

795853 Grey 19 Road Collingwood, Simcoe, ON MLS® S13452012

Residential Freehold (Detached)

$1229000.0

5 Beds
4 Baths
2500-3000 sq-ft

Set on a beautifully private rural lot w/ stunning views of Blue Mountain & only 7 minutes from downtown Collingwood, this charming ranch bungalow off

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8352 Main Lisle Street, Simcoe, ON , MLS #N13450998 , Image - 1

8352 Main Lisle Street Lisle, Adjala-Tosorontio, Simcoe, ON MLS® N13450998

Residential Freehold (Detached)

$999800.0

5 +6 Beds
4 Baths
2500-3000 sq-ft

Investor Opportunity on a Rare Oversized Lot! Situated on an expansive 82 x 602 ft lot backing onto a serene forest, this private property offers exce

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19 Marigold Boulevard, Simcoe, ON , MLS #N13168070 , Image - 1

19 Marigold Boulevard Colgan, Adjala-Tosorontio, Simcoe, ON MLS® N13168070

Residential Freehold (Detached)

$2049000.0

Price drop by 2.2%

5 +1 Beds
5 Baths
5000 + sq-ft

Luxurious Tribute-Built Detached Home in Tottenham A Rare Gem!Welcome to this masterpiece, boasting an impressive 5,115 sq. ft. of thoughtfully design

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56 Redmond Crescent, Simcoe, ON , MLS #S13148482 , Image - 1

56 Redmond Crescent Centre Vespra, Springwater, Simcoe, ON MLS® S13148482

Residential Freehold (Detached)

$1560000.0

5 Beds
6 Baths
3500-5000 sq-ft

Set within the prestigious Stonemanor Woods community, this home stands out for its scale, layout, and level of finish. 5 bedrooms, 4 car garage and o

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71 OAK LEA Boulevard, Simcoe, ON , MLS #S13132518 , Image - 1

71 OAK LEA Boulevard Wasaga Beach, Simcoe, ON MLS® S13132518

Residential Freehold (Detached)

$1950000.0

5 +0 Beds
4 Baths
3500-5000 sq-ft

Experience the pinnacle of contemporary design in this newly built riverfront masterpiece boasting 4,000 above-ground square feet in a tranquil Wasaga

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9 Windrose Valley Boulevard, Simcoe, ON , MLS #S13102874 , Image - 1

9 Windrose Valley Boulevard Rural Clearview, Clearview, Simcoe, ON MLS® S13102874

Residential Freehold (Detached)

$2899000.0

5 +1 Beds
5 Baths
5000 + sq-ft

Welcome to WINDROSE VALLEY ESTATES. This beautiful home only 5 years old built by McPherson Builders is set on a 2.3 acre corner lot with a long drive

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1617 42 County Road, Simcoe, ON , MLS #S13005546 , Image - 1

1617 42 County Road Rural Clearview, Clearview, Simcoe, ON MLS® S13005546

Residential Freehold (Farm)

$1950000.0

Price drop by 14.8%

5 Beds
2 Baths
1500-2000 sq-ft

98 acre Farm property with Century Home and Commercial Facilities. An extraordinary opportunity to set up you own Farm Business with 5 bedroom Residen

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3730 Mangusta Court, Simcoe, ON , MLS #N13439676 , Image - 1

3730 Mangusta Court Rural Innisfil, Innisfil, Simcoe, ON MLS® N13439676

Residential Freehold (Att/Row/Townhouse)

$2899999.0

5 Beds
5 Baths
3500-5000 sq-ft

Client RemarksRESORT LIVING AT ITS FINEST - Stunning 3550 Sqft Fully Upgraded End Unit Island Town On Prime Mangusta Court In The Sought After Marina

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1 Sturgeon Bay Road, Simcoe, ON , MLS #S13431996 , Image - 1

1 Sturgeon Bay Road Coldwater, Severn, Simcoe, ON MLS® S13431996

Residential Freehold (Detached)

$599900.0

5 Beds
3 Baths
3500-5000 sq-ft

Located on the banks of the Coldwater river this 5-bedroom, 3-bath Victorian home offers plenty of space and a unique setting. The home features large

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2338 Buchanan Street, Simcoe, ON , MLS #N13431664 , Image - 1

2338 Buchanan Street Alcona, Innisfil, Simcoe, ON MLS® N13431664

Residential Freehold (Detached)

$2250000.0

5 Beds
5 Baths
3500-5000 sq-ft

2023 CUSTOM-BUILT STUDIO MCGEE-INSPIRED LUXURY ESTATE WITH 4,153 SQ FT OF DESIGNER FINISHES, RADIANT HEATED FLOORS IN THE BASEMENT & TRIPLE GARAGE! Bu

5 Bedroom Houses for Sale in Simcoe Under $10M - P6

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