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Detached Houses for Sale in Simcoe Under $5M - P29

Showing results 841 - 870 of 3391
Last Updated: August 06, 2026
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  • Price(Hi-Lo)
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49 Photos
Last Updated : 7 Days ago
29 TECUMSETH Street, Simcoe, ON , MLS #S13622146 , Image - 1
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29 TECUMSETH Street Orillia, Simcoe, ON MLS® S13622146

Residential Freehold (Detached)

$849000.0
  • 5 Beds
  • 4 Baths
  • 3500-5000 sq-ft
Welcome to 29 Tecumseth Street in Orillia, a distinctive 2 1/2-storey century home where history meets modern updates. Originally built in 1900 just a
24 Photos
Last Updated : 7 Days ago
24 Indianola Crescent, Simcoe, ON , MLS #S13620996 , Image - 1

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24 Indianola Crescent Wasaga Beach, Simcoe, ON MLS® S13620996

Residential Freehold (Detached)

$699000.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
209 FEET OF FRONTAGE!! DEVELOPMENT POTENTIAL ~Spacious 209.15 ft x 230 ft irregular lot~ incredible potential for property development/ severances. Th
38 Photos
Last Updated : 7 Days ago
706 Reid Street, Simcoe, ON , MLS #N13602004 , Image - 1

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706 Reid Street Alcona, Innisfil, Simcoe, ON MLS® N13602004

Residential Freehold (Detached)

$699900.0
  • 2 +1 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Beautifully renovated home in a terrific neighbourhood. Just down the street to the bottom of 9th line and Lake Simcoe. Full size single car garage wi
39 Photos
Last Updated : 7 Days ago
39 Orma Drive, Simcoe, ON , MLS #S13619188 , Image - 1

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39 Orma Drive Orillia, Simcoe, ON MLS® S13619188

Residential Freehold (Detached)

$639900.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Every home is like a book, filled with stories of family, character and adventure. At 39 Orma Drive, you can feel the chapters that have already been
Pre-Construction
Rosehaven Simcoe Woods
6 Photos

Rosehaven Simcoe Woods

Innisfil Beach Road & Webster Boulevard
From $879,990 - $1,339,990
project size image
Project Info
  • Units
  • Townhouses
building outline
Property Mix
Floorplans coming soon
Developer:Rosehaven Homes
29 Photos
Last Updated : 7 Days ago
60 Church Street, Simcoe, ON , MLS #S13571092 , Image - 1

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60 Church Street Penetanguishene, Simcoe, ON MLS® S13571092

Residential Freehold (Detached)

$349000.0
  • 2 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Warm, Inviting & Opportunity-Focused. Full of history and potential, this century-old 2-bedroom storey-and-a-half home is ready for someone with crea
35 Photos
Last Updated : 7 Days ago
211 Roy Drive, Simcoe, ON , MLS #S13621396 , Image - 1

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211 Roy Drive Stayner, Clearview, Simcoe, ON MLS® S13621396

Residential Freehold (Detached)

$849900.0
  • 3 +2 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Tucked away on a quiet street with no through traffic, this raised bungalow offers the space, privacy, and location today's families are searching for
44 Photos
Last Updated : 7 Days ago
104 The Steps Road, Simcoe, ON , MLS #S13584416 , Image - 1

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104 The Steps Road Rural Ramara, Ramara, Simcoe, ON MLS® S13584416

Residential Freehold (Detached)

$1299888.0
  • 5 Beds
  • 3 Baths
  • 1500-2000 sq-ft
YOUR OWN PRIVATE BEACH ON LAKE SIMCOE! Experience waterfront living at its best with this beautifully renovated Lake Simcoe home, complete with your o
39 Photos
Last Updated : 7 Days ago
2 Hook Court, Simcoe, ON , MLS #S13621808 , Image - 1

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2 Hook Court West Bayfield, Barrie, Simcoe, ON MLS® S13621808

Residential Freehold (Detached)

$999999.0
  • 5 +3 Beds
  • 5 Baths
  • 2500-3000 sq-ft
Discover this stunning oversized two-storey detached home with a double-car garage, ideally situated on a quiet court in the highly sought-after North
29 Photos
Last Updated : 7 Days ago
1246 Leslie Drive, Simcoe, ON , MLS #N13621368 , Image - 1

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1246 Leslie Drive Alcona, Innisfil, Simcoe, ON MLS® N13621368

Residential Freehold (Detached)

$1074900.0
  • 4 +1 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Ready for the pages of a magazine, this executive home delivers city luxury and country serenity in one complete package. Enjoy exceptional curb appea
1 Photos
Last Updated : 7 Days ago
3525 Tenth Line, Simcoe, ON
3525 Tenth Line Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13422752

Residential Freehold (Detached)

Price On Request
  • 5 +2 Beds
  • 4 Baths
  • 3000-3500 sq-ft
Discover an exceptional opportunity to acquire 20 acres of prime land in the highly sought-after Bradford West Gwillimbury area**. Ideally positioned
34 Photos
Last Updated : 7 Days ago
146 Nottingham Road N, Simcoe, ON , MLS #S13621668 , Image - 1

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146 Nottingham Road N Rural Barrie Southeast, Barrie, Simcoe, ON MLS® S13621668

Residential Freehold (Detached)

$999000.0
  • 4 +1 Beds
  • 5 Baths
  • 2000-2500 sq-ft
Only 2 years old! 4-bedroom home, perfect for a growing family. Thoughtfully designed with high ceilings and large windows, this home is filled with n
18 Photos
Last Updated : 7 Days ago
6121 Concession B C Road, Simcoe, ON , MLS #S11887032 , Image - 1

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6121 Concession B C Road Rural Ramara, Ramara, Simcoe, ON MLS® S11887032

Residential Freehold (Detached)

$818000.0
price drop iconPrice drop by 17.4%
  • 3 Beds
  • 2 Baths
  • 1500-2000 sq-ft
ANOTHER QUALITY KRISTENSEN BUILDERS HOME, 1600 ft. , THREE BEDROOMS, WITH A LARGE 2 CAR ATTACHED GARAGE,[ 22'.5 X 24'8] MAIN FLOOR AND BASEMENT ENTRAN
11 Photos
Last Updated : 7 Days ago
1521 Stovell Crescent, Simcoe, ON , MLS #N13621632 , Image - 1

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1521 Stovell Crescent Lefroy, Innisfil, Simcoe, ON MLS® N13621632

Residential Freehold (Detached)

$949999.0
  • 4 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Welcome to 1521 Stovell Crescent, an exceptional semi-custom residence offering 2,480 sq.ft. of impeccably upgraded living space on a premium ravine-f
43 Photos
Last Updated : 7 Days ago
108 Durham Avenue, Simcoe, ON , MLS #S13223302 , Image - 1

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108 Durham Avenue Rural Barrie Southeast, Barrie, Simcoe, ON MLS® S13223302

Residential Freehold (Detached)

$784900.0
price drop iconPrice drop by 9.2%
  • 4 +1 Beds
  • 4 Baths
  • 2000-2500 sq-ft
108 Durham does something most detached homes in Barrie can't: it gives you a full four-bedroom family home and a separate in-law suite under one roof
42 Photos
Last Updated : 7 Days ago
133 Timcourt Drive, Simcoe, ON , MLS #S13132304 , Image - 1

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133 Timcourt Drive Rural Tiny, Tiny, Simcoe, ON MLS® S13132304

Residential Freehold (Detached)

$599777.0
  • 3 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Welcome to 133 Timcourt Drive in Tiny Township, offering the perfect opportunity for those seeking a year-round home or a relaxing cottage retreat. Ne
41 Photos
Last Updated : 7 Days ago
2448 Stockdale Road, Simcoe, ON , MLS #S13548570 , Image - 1

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2448 Stockdale Road West Shore, Severn, Simcoe, ON MLS® S13548570

Residential Freehold (Detached)

$1479000.0
price drop iconPrice drop by 1.4%
  • 5 Beds
  • 5 Baths
  • 3000-3500 sq-ft
Welcome to 2448 Stockdale Road, Severn Township. Set on 4 acres, this luxurious custom-built home with wrap-around porch showcases exceptional craftsm
41 Photos
Last Updated : 7 Days ago
29 Nicholson Drive, Simcoe, ON , MLS #S13211664 , Image - 1

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29 Nicholson Drive Ardagh, Barrie, Simcoe, ON MLS® S13211664

Residential Freehold (Detached)

$699000.0
  • 3 +1 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome to 29 Nicholson Drive, a well maintained fully detached home in Barrie's desirable Ardagh neighbourhood. This property offers 3+1 bedrooms and
1 Photos
Last Updated : 7 Days ago
2872 Sunset Drive, Simcoe, ON
2872 Sunset Drive Rural Ramara, Ramara, Simcoe, ON MLS® S13246410

Residential Freehold (Detached)

$659000.0
price drop iconPrice drop by 2.9%
  • 3 +1 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Attention all Nature Lovers, Fishermen and Fisherwomen, People that like Privacy! Welcome to 2872 Sunset Drive. This private and peaceful brick bunga
42 Photos
Last Updated : 7 Days ago
3787 Harry's Lane, Simcoe, ON , MLS #S13217544 , Image - 1

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3787 Harry's Lane Rural Ramara, Ramara, Simcoe, ON MLS® S13217544

Residential Freehold (Detached)

$1299000.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome to prestigious Val Harbour Estates, ideally located just minutes from the beautiful city of Orillia. Situated on an impressive 109.98ft x 174.
38 Photos
Last Updated : 7 Days ago
16 Longman Drive, Simcoe, ON , MLS #S13531082 , Image - 1

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16 Longman Drive Northwest, Barrie, Simcoe, ON MLS® S13531082

Residential Freehold (Detached)

$769900.0
price drop iconPrice drop by 1.9%
  • 3 Beds
  • 4 Baths
  • 1500-2000 sq-ft
Welcome to this beautifully updated detached home located in a family friendly neighbourhood close to schools, parks, shopping, and all amenities. Off
50 Photos
Last Updated : 7 Days ago
1834 Tiny Beaches Road S, Simcoe, ON , MLS #S13531538 , Image - 1

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1834 Tiny Beaches Road S Rural Tiny, Tiny, Simcoe, ON MLS® S13531538

Residential Freehold (Detached)

$1599000.0
  • 3 +3 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Lakefront Custom Bungalow Welcome to your dream waterfront retreat! This original-owner, custom-built lakefront bungalow offers a rare opportunity to
43 Photos
Last Updated : 7 Days ago
20 Nippissing Ridge Road, Simcoe, ON , MLS #S13091276 , Image - 1

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20 Nippissing Ridge Road Rural Tiny, Tiny, Simcoe, ON MLS® S13091276

Residential Freehold (Detached)

$1998000.0
price drop iconPrice drop by 9.2%
  • 6 Beds
  • 5 Baths
  • 3500-5000 sq-ft
Perched high on a ridge in the coveted Cedar Ridge community at Cedar Point, this exceptional four-season residence captures sweeping panoramic views
25 Photos
Last Updated : 7 Days ago
378 ABERDEEN Boulevard, Simcoe, ON , MLS #S13488556 , Image - 1

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378 ABERDEEN Boulevard Midland, Simcoe, ON MLS® S13488556

Residential Freehold (Detached)

$944900.0
price drop iconPrice drop by 1.6%
  • 3 +0 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Welcome to this beautifully maintained custom bungalow nestled on a generous lot in one of Midland's most sought-after neighbourhoods. This home offer
42 Photos
Last Updated : 7 Days ago
20 Falcon Crescent, Simcoe, ON , MLS #S13621018 , Image - 1

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20 Falcon Crescent Innis-Shore, Barrie, Simcoe, ON MLS® S13621018

Residential Freehold (Detached)

$974900.0
  • 4 Beds
  • 3 Baths
  • 3000-3500 sq-ft
Welcome to 20 Falcon Cres, an exceptional family home in Barrie's sought-after Innishore neighbourhood. Situated on a quiet, tree-lined street, this b
37 Photos
Last Updated : 7 Days ago
144 George Street, Simcoe, ON , MLS #S13597768 , Image - 1

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144 George Street Victoria Harbour, Tay, Simcoe, ON MLS® S13597768

Residential Freehold (Detached)

$724777.0
  • 3 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
Welcome to this versatile and family-friendly home located in the heart of Victoria Harbour! This spacious property offers 3+ bedrooms, two bathrooms,
50 Photos
Last Updated : 7 Days ago
449 Park Street, Simcoe, ON , MLS #S13592822 , Image - 1

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449 Park Street Rural Tay, Tay, Simcoe, ON MLS® S13592822

Residential Freehold (Detached)

$1324777.0
  • 6 +0 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Welcome to 449 Park Street, a fully renovated property offering incredible value and versatility. The main home has been updated from top to bottom wi
31 Photos
Last Updated : 7 Days ago
1032 Dominion Avenue, Simcoe, ON , MLS #S13592130 , Image - 1

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1032 Dominion Avenue Midland, Simcoe, ON MLS® S13592130

Residential Freehold (Detached)

$599777.0
  • 3 +1 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Location Plus in Midland's Desirable West End! This solid all-brick family home offers comfort, space, and convenience in a great neighbourhood. Featu
33 Photos
Last Updated : 7 Days ago
3086 Emperor Drive, Simcoe, ON , MLS #S13008040 , Image - 1

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3086 Emperor Drive Orillia, Simcoe, ON MLS® S13008040

Residential Freehold (Detached)

$759000.0
price drop iconPrice drop by 6.9%
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
*PRICE REDUCTION OF $50,000!* Step into this beautiful detached 2-storey home located in the heart of Orillia's highly sought-after West Ridge communi
42 Photos
Last Updated : 7 Days ago
65 Adams Street, Simcoe, ON , MLS #N13160288 , Image - 1

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65 Adams Street Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13160288

Residential Freehold (Detached)

$789000.0
price drop iconPrice drop by 1.4%
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to 65 Adams Street! Bright & beautifully updated 3-bedroom home with walkout basement located in a family-friendly neighbourhood in the heart
37 Photos
Last Updated : 7 Days ago
369 Queen Street, Simcoe, ON , MLS #S13560212 , Image - 1

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369 Queen Street Midland, Simcoe, ON MLS® S13560212

Residential Freehold (Detached)

$349900.0
  • 2 +1 Beds
  • 2 Baths
  • 1100-1500 sq-ft
This one is personal. This was my grandma's house-the place I grew up visiting for homemade apple pies, her home cooking and more family memories than
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