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Detached Houses for Sale in Simcoe Under $5M - P25

Showing results 721 - 750 of 3358
Last Updated: September 21, 2026
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  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
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47 Photos
Last Updated : 5 Days ago
213 Mary Street, Simcoe, ON , MLS #S13557334 , Image - 1
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213 Mary Street Creemore, Clearview, Simcoe, ON MLS® S13557334

Residential Freehold (Detached)

$879900.0
  • 3 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Enjoy living in the safe, friendly community of Creemore in this immaculate, low-maintenance, newly constructed 3-bedroom bungalow with 1600 ft. of li
35 Photos
Last Updated : 5 Days ago
6376 Rama Road W, Simcoe, ON , MLS #S13773952 , Image - 1

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6376 Rama Road W Rural Ramara, Ramara, Simcoe, ON MLS® S13773952

Residential Freehold (Detached)

$3725000.0
  • 4 +0 Beds
  • 3 Baths
  • 3500-5000 sq-ft
6376 Rama Road redefines the standard for LUXURY waterfront living in Simcoe County. This incredible 103 waterfront property with prime Western expos
37 Photos
Last Updated : 5 Days ago
34 Tuscany Grande N/A, Simcoe, ON , MLS #N13626258 , Image - 1

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34 Tuscany Grande N/A Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13626258

Residential Condo & Other (Detached Condo)

$845000.0
  • 1 +2 Beds
  • 3 Baths
  • 1200-1399 sq-ft
Welcome to executive bungalow living in one of the most desirable locations within Briar Hill, a great active adult community in Alliston! Perfectly s
49 Photos
Last Updated : 5 Days ago
28 Boyd Crescent, Simcoe, ON , MLS #S13706164 , Image - 1

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28 Boyd Crescent Moonstone, Oro-Medonte, Simcoe, ON MLS® S13706164

Residential Freehold (Detached)

$1075000.0
  • 3 +1 Beds
  • 4 Baths
  • 1500-2000 sq-ft
Tucked away on a picturesque, tree-lined half-acre lot in the desirable community of Moonstone, this stunningly renovated bungalow offers the perfect
Open House : Sat Sep 26, 11:00 AM to 01:00 PM
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
40 Photos
Last Updated : 5 Days ago
6815 4th Line, Simcoe, ON , MLS #N13665928 , Image - 1

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6815 4th Line Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13665928

Residential Freehold (Detached)

$979900.0
  • 3 +1 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Set on an expansive 150' x 200' lot, this Sidesplit offers over 2000sq ft of finished functional living space and offers the feeling of country living
48 Photos
Last Updated : 5 Days ago
2043 Concession 5 Road, Simcoe, ON , MLS #N13671462 , Image - 1

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2043 Concession 5 Road Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N13671462

Residential Freehold (Detached)

$1445000.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
This is not your everyday home its something truly special. Thoughtfully designed and full of character, this distinctive property stands out in all t
48 Photos
Last Updated : 5 Days ago
7765 5 Sideroad Tosorontio N/A, Simcoe, ON , MLS #N13672296 , Image - 1

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7765 5 Sideroad Tosorontio N/A Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N13672296

Residential Freehold (Detached)

$1699900.0
  • 3 +3 Beds
  • 6 Baths
  • 2500-3000 sq-ft
Located minutes from Alliston and backing onto Earl Rowe Provincial Park, this substantial 6-bedroom, 5-bathroom home offers over 5,500 sq. ft. of fin
10 Photos
Last Updated : 5 Days ago
157 Desroches Trail, Simcoe, ON , MLS #S13734936 , Image - 1

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157 Desroches Trail Rural Tiny, Tiny, Simcoe, ON MLS® S13734936

Residential Freehold (Detached)

$849500.0
  • 2 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Trade the GTA Commute for Georgian Bay Living!Imagine starting your day with a quiet coffee on your covered porch, walking to the beach or forest trai
50 Photos
Last Updated : 5 Days ago
8 Dunn Avenue, Simcoe, ON , MLS #S13791572 , Image - 1

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8 Dunn Avenue Orillia, Simcoe, ON MLS® S13791572

Residential Freehold (Detached)

$459900.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
This charming West Ward bungalow is proof that great things come in small packages! Set on a surprisingly deep, private lot surrounded by mature trees
35 Photos
Last Updated : 5 Days ago
4 Thomas Street, Simcoe, ON , MLS #N13719912 , Image - 1

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4 Thomas Street Glencairn, Adjala-Tosorontio, Simcoe, ON MLS® N13719912

Residential Freehold (Detached)

$949900.0
  • 5 Beds
  • 2 Baths
  • 3000-3500 sq-ft
Timeless Character, Nearly 3 Acres & Endless Possibilities! Welcome to this remarkable late-1800s century home, beautifully set on nearly 3 acres of p
50 Photos
Last Updated : 5 Days ago
2110 Concession 8 Road, Simcoe, ON , MLS #S13770576 , Image - 1

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2110 Concession 8 Road Rural Clearview, Clearview, Simcoe, ON MLS® S13770576

Residential Freehold (Detached)

$1450000.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
A rare offering where exceptional design meets an extraordinary setting! Extensively renovated and impeccably presented, this private property is fram
31 Photos
Last Updated : 5 Days ago
19 Callander Crescent, Simcoe, ON , MLS #N13773014 , Image - 1

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19 Callander Crescent Alliston, New Tecumseth, Simcoe, ON MLS® N13773014

Residential Freehold (Detached)

$699000.0
  • 3 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Located in a family-friendly neighbourhood, this well-appointed home is just a short walk to the community park, local school, and the shops and resta
45 Photos
Last Updated : 5 Days ago
11 King Street S, Simcoe, ON , MLS #N13775290 , Image - 1

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11 King Street S Cookstown, Innisfil, Simcoe, ON MLS® N13775290

Residential Freehold (Detached)

$750000.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to Cookstown! Solid, well-maintained bungalow ideally located in the heart of Cookstown with a generous 70.63' x 177.05' lot with a large, ful
37 Photos
Last Updated : 5 Days ago
8116 Main Street, Simcoe, ON , MLS #N13771426 , Image - 1

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8116 Main Street Everett, Adjala-Tosorontio, Simcoe, ON MLS® N13771426

Residential Freehold (Detached)

$595000.0
  • 3 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Step into this affordable Century Home that perfectly blends historic charm with eclectic flair. Bursting with personality and warmth, this unique res
28 Photos
Last Updated : 5 Days ago
3118 Grange Avenue, Simcoe, ON , MLS #S13470060 , Image - 1

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3118 Grange Avenue Rural Severn, Severn, Simcoe, ON MLS® S13470060

Residential Freehold (Detached)

$899999.0
price drop iconPrice drop by 5.2%
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Newly built cottage on the Severn river on a year round road. 2 bedroom open concept cottage with a large loft and vaulted ceilings. Beautiful eat in
31 Photos
Last Updated : 5 Days ago
3304 Goldstein Road, Simcoe, ON , MLS #S13791484 , Image - 1

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3304 Goldstein Road West Shore, Severn, Simcoe, ON MLS® S13791484

Residential Freehold (Detached)

$724900.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to 3304 Goldstein Road, a beautifully maintained raised bungalow located just 10 minutes north of Orillia in the community of Washago, Ontario
50 Photos
Last Updated : 5 Days ago
4410 Manton Lane, Simcoe, ON , MLS #S13785380 , Image - 1

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4410 Manton Lane Rural Severn, Severn, Simcoe, ON MLS® S13785380

Residential Freehold (Detached)

$1998000.0
  • 3 +2 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Welcome to an exceptional Severn River retreat, privately positioned on a picturesque point with an impressive 465 feet of shoreline and panoramic vie
23 Photos
Last Updated : 5 Days ago
43 Graihawk Drive, Simcoe, ON , MLS #S13791426 , Image - 1

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43 Graihawk Drive Ardagh, Barrie, Simcoe, ON MLS® S13791426

Residential Freehold (Detached)

$829900.0
  • 4 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Original Owner, Exceptionally Maintained & Built By Highly Regarded Grandview Homes, This Beautiful Family Home Is Nestled On One Of Barrie's Most Des
26 Photos
Last Updated : 5 Days ago
1 Lang Drive, Simcoe, ON , MLS #S13791402 , Image - 1

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1 Lang Drive Northwest, Barrie, Simcoe, ON MLS® S13791402

Residential Freehold (Detached)

$599900.0
  • 2 +3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to 1 Lang Drive - Freshly painted throughout, this bungalow offers exceptional value in a popular, family-friendly neighbourhood! This beautif
45 Photos
Last Updated : 5 Days ago
46 Brick Pond Road, Simcoe, ON , MLS #S13581376 , Image - 1

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46 Brick Pond Road Coldwater, Severn, Simcoe, ON MLS® S13581376

Residential Freehold (Detached)

$814900.0
price drop iconPrice drop by 4.1%
  • 3 +1 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome to this stunning 5 year young custom bungalow backing onto lush greenery. With 3300 square feet, yes you read that right, of living space on t
50 Photos
Last Updated : 5 Days ago
2166 10th Side Road, Simcoe, ON , MLS #N13791364 , Image - 1

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2166 10th Side Road Rural Bradford West Gwillimbury, Bradford West Gwillimbury, Simcoe, ON MLS® N13791364

Residential Freehold (Detached)

$3248800.0
  • 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
1 Photos
Last Updated : 5 Days ago
38 Masters Drive, Simcoe, ON
38 Masters Drive East Bayfield, Barrie, Simcoe, ON MLS® S13723720

Residential Freehold (Detached)

$859800.0
price drop iconPrice drop by 14.0%
  • 3 +2 Beds
  • 4 Baths
  • 2000-2500 sq-ft
WELCOME TO 38 MASTERS DR, LOCATED IN A FAMILY ORIENTED NEIGHBORHOOD, WITH LARGE WINDOWS AND A WALKOUT BASEMENT PROVIDES BRIGHT NATURE SUNLIGHTING, WIT
49 Photos
Last Updated : 5 Days ago
123 Ruffet Drive, Simcoe, ON , MLS #S13788796 , Image - 1

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123 Ruffet Drive Edgehill Drive, Barrie, Simcoe, ON MLS® S13788796

Residential Freehold (Detached)

$800000.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
UPGRADED DETACHED HOME, (4 BEDROOM 3 BATHROOM, 2 CAR GARAGE) IN EDGEHILL COMMUNITY. THE MAIN FLOOR OFFERS SEPARATE LIVING, DINING & FAMILY ROOMS. FAM
50 Photos
Last Updated : 5 Days ago
1520 Rosemount Road, Simcoe, ON , MLS #S13788036 , Image - 1

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1520 Rosemount Road Rural Tay, Tay, Simcoe, ON MLS® S13788036

Residential Freehold (Detached)

$1890000.0
  • 4 +2 Beds
  • 4 Baths
  • 3000-3500 sq-ft
Top 5 Reasons You Will Love This Home: 1) An extraordinary country retreat on 8.5 scenic acres overlooking the tranquil Sturgeon River, surrounded by
43 Photos
Last Updated : 5 Days ago
29 SANFORD Circle, Simcoe, ON , MLS #S13783696 , Image - 1

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29 SANFORD Circle Centre Vespra, Springwater, Simcoe, ON MLS® S13783696

Residential Freehold (Detached)

$1450000.0
  • 5 Beds
  • 4 Baths
  • 3500-5000 sq-ft
WELCOME TO LUXURY SCALE IN SPRINGWATER. Nestled on a premium lot, 29 Sanford Circle represents a rare opportunity boasting a monumental 4,269 sq ft of
38 Photos
Last Updated : 5 Days ago
37 Marilyn Avenue N, Simcoe, ON , MLS #S13791210 , Image - 1

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37 Marilyn Avenue N Wasaga Beach, Simcoe, ON MLS® S13791210

Residential Freehold (Detached)

$929900.0
  • 3 +1 Beds
  • 4 Baths
  • 1100-1500 sq-ft
Beautifully maintained 3+1 bedroom raised bungalow with a LEGAL 1-BEDROOM APARTMENT and rental income potential of approximately $20,000 annually. Ide
44 Photos
Last Updated : 5 Days ago
27 Nida Drive, Simcoe, ON , MLS #S13741416 , Image - 1

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27 Nida Drive Rural Tiny, Tiny, Simcoe, ON MLS® S13741416

Residential Freehold (Detached)

$575000.0
  • 2 +2 Beds
  • 2 Baths
  • 700-1100 sq-ft
So many possibilities in this fully renovated home with in-law potential just steps to the beaches of Georgian Bay! Located in Tiny Township, just a s
32 Photos
Last Updated : 5 Days ago
10 Sinclair Crescent, Simcoe, ON , MLS #S13479154 , Image - 1

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10 Sinclair Crescent Atherley, Ramara, Simcoe, ON MLS® S13479154

Residential Freehold (Detached)

$599900.0
  • 3 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Experience Refined Adult Living at Lakepoint Village. Discover The Perfect Harmony Of Rural Serenity And Urban Convenience In This Premier Adult Lifes
42 Photos
Last Updated : 5 Days ago
36 Regalia Way, Simcoe, ON , MLS #S13724266 , Image - 1

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36 Regalia Way Innis-Shore, Barrie, Simcoe, ON MLS® S13724266

Residential Freehold (Detached)

$1175000.0
price drop iconPrice drop by 5.9%
  • 4 +1 Beds
  • 5 Baths
  • 2500-3000 sq-ft
Beautifully renovated, thoughtfully designed and truly turn-key, this exceptional 4 + 1 bedroom, 5-bathroom home is made for living well and entertain
45 Photos
Last Updated : 5 Days ago
64 Vanessa Drive, Simcoe, ON , MLS #S13696376 , Image - 1

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64 Vanessa Drive Orillia, Simcoe, ON MLS® S13696376

Residential Freehold (Detached)

$679900.0
price drop iconPrice drop by 4.2%
  • 3 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Beautifully finished and move-in ready, this 3-bedroom, 3-bathroom home is located in Orillia's popular West Ridge community. Bright and airy, it offe
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