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Detached Houses for Sale in Simcoe Under $5M - P19

Showing results 541 - 570 of 3367
Last Updated: September 21, 2026
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50 Photos
Last Updated : 4 Days ago
295 Sunnybrae Avenue, Simcoe, ON , MLS #N13786620 , Image - 1
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295 Sunnybrae Avenue Stroud, Innisfil, Simcoe, ON MLS® N13786620

Residential Freehold (Detached)

$1399000.0
  • 4 Beds
  • 3 Baths
  • 3500-5000 sq-ft
Estate living in prestigious Innisfil Estates. Positioned on a quiet, generously proportioned street among distinguished custom residences and meticul
Open House : Sun Sep 27, 01:00 PM to 03:00 PM
41 Photos
Last Updated : 4 Days ago
2997 Stone Ridge Boulevard, Simcoe, ON , MLS #S13559916 , Image - 1

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2997 Stone Ridge Boulevard Orillia, Simcoe, ON MLS® S13559916

Residential Freehold (Detached)

$799999.0
  • 5 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Whether you're searching for a spacious single-family home, a true multigenerational property with a private in-law suite, or an investment opportunit
49 Photos
Last Updated : 4 Days ago
75 Edward Street E, Simcoe, ON , MLS #S13795114 , Image - 1

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75 Edward Street E Creemore, Clearview, Simcoe, ON MLS® S13795114

Residential Freehold (Detached)

$884000.0
  • 3 +1 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Thoughtfully updated and beautifully presented, this inviting bungalow in the picturesque Village of Creemore reflects its owners' commitment to quali
47 Photos
Last Updated : 4 Days ago
25 Glengrove Avenue, Simcoe, ON , MLS #S13713254 , Image - 1

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25 Glengrove Avenue Prices Corners, Oro-Medonte, Simcoe, ON MLS® S13713254

Residential Freehold (Detached)

$649900.0
  • 2 +1 Beds
  • 1 Baths
  • 700-1100 sq-ft
WOW! MOVE-IN READY, FULLY FINISHED & JUST STEPS TO BASS LAKE! This extensively updated home sits on an AWESOME 100' x 150' lot and offers OPEN-CONCEP
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
38 Photos
Last Updated : 4 Days ago
36 Meadows Avenue, Simcoe, ON , MLS #S13795086 , Image - 1

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36 Meadows Avenue Rural Tay, Tay, Simcoe, ON MLS® S13795086

Residential Freehold (Detached)

$849900.0
  • 3 Beds
  • 2 Baths
  • 2500-3000 sq-ft
Are you looking for space? Do you need space to roam? Space for recreational toys? Storage? A Workshop? Your own Private Retreat? This property has it
15 Photos
Last Updated : 4 Days ago
5263 Elliott Side Road, Simcoe, ON , MLS #S13679224 , Image - 1

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Unit-5, 5263 Elliott Side Road Rural Tay, Tay, Simcoe, ON MLS® S13679224

Residential Freehold (Detached)

$169000.0
price drop iconPrice drop by 11.0%
  • 3 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Fixer-upper opportunity in Tiny Township in the Bramhall Community! This 3-bedroom, 1-bathroom modular home sits on a land leased lot in a private set
35 Photos
Last Updated : 4 Days ago
50 Regina Boulevard, Simcoe, ON , MLS #S13488432 , Image - 1

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50 Regina Boulevard Wasaga Beach, Simcoe, ON MLS® S13488432

Residential Freehold (Detached)

$799000.0
price drop iconPrice drop by 5.9%
  • 3 +2 Beds
  • 3 Baths
  • 1500-2000 sq-ft
This beautiful home and spectacular lot is a must see. Perfect for a retiring couple or a large family who needs an in law suite. The whole house
49 Photos
Last Updated : 4 Days ago
109 Vipond Way, Simcoe, ON , MLS #N13748148 , Image - 1

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109 Vipond Way Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13748148

Residential Freehold (Detached)

$999000.0
price drop iconPrice drop by 2.9%
  • 4 +1 Beds
  • 4 Baths
  • 2500-3000 sq-ft
UNBELIEVABLE PRICE FOR A DETACHED CORNER-LOT HOME! Don't miss this incredible opportunity to own a spacious 4-bedroom, 4-bathroom detached home in a h
33 Photos
Last Updated : 4 Days ago
7 Empire Drive, Simcoe, ON , MLS #S13674480 , Image - 1

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7 Empire Drive Innis-Shore, Barrie, Simcoe, ON MLS® S13674480

Residential Freehold (Detached)

$949999.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Welcome to 7 Empire Dr, a stunning detached four bedroom home offering modern elegance and complete move in ready comfort. Featuring a bright open con
28 Photos
Last Updated : 4 Days ago
2709 Wainman Line, Simcoe, ON , MLS #S13794896 , Image - 1

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2709 Wainman Line Rural Severn, Severn, Simcoe, ON MLS® S13794896

Residential Freehold (Detached)

$1295000.0
  • 3 +1 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Tucked away in 5 Acres of pristine forest, this extraordinary private estate offers a rare opportunity to own a place where peace, nature, and luxury
34 Photos
Last Updated : 4 Days ago
64 Wahnekewening Drive, Simcoe, ON , MLS #S13788876 , Image - 1

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64 Wahnekewening Drive Rural Tiny, Tiny, Simcoe, ON MLS® S13788876

Residential Freehold (Detached)

$1189000.0
  • 3 +2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Georgian Bay Beachfront Living at Its Best! Wake up to stunning views of Georgian Bay and step directly onto one of the area's most beautiful sandy be
43 Photos
Last Updated : 4 Days ago
191 Livingstone Street W, Simcoe, ON , MLS #S13743630 , Image - 1

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191 Livingstone Street W Sunnidale, Barrie, Simcoe, ON MLS® S13743630

Residential Freehold (Detached)

$699000.0
  • 4 +2 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Rare legal duplex in Barrie's established Sunnidale neighbourhood: a beautifully updated 4 bedroom, 2.5 bath detached home offering 2,338 sq. ft. abov
46 Photos
Last Updated : 4 Days ago
2944 County Road 50 Road, Simcoe, ON , MLS #N13794682 , Image - 1

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2944 County Road 50 Road Loretto, Adjala-Tosorontio, Simcoe, ON MLS® N13794682

Residential Freehold (Detached)

$1150000.0
  • 5 Beds
  • 2 Baths
  • 2000-2500 sq-ft
Welcome to this beautifully renovated country home with 5 bedrooms and 2 bathrooms, where modern updates meet spacious living and a peaceful setting.
50 Photos
Last Updated : 4 Days ago
1326 Gilford Road, Simcoe, ON , MLS #N13698412 , Image - 1

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1326 Gilford Road Gilford, Innisfil, Simcoe, ON MLS® N13698412

Residential Freehold (Detached)

$1298800.0
  • 3 +1 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Original Owners never been for sale. Custom Built Bungalow with 3500+ Sq Ft of Living Space. Gorgeous private yard over 1/2 Acre. Extensive gardens, t
40 Photos
Last Updated : 4 Days ago
199 Shephard Avenue, Simcoe, ON , MLS #N13769658 , Image - 1

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199 Shephard Avenue Alliston, New Tecumseth, Simcoe, ON MLS® N13769658

Residential Freehold (Detached)

$899000.0
  • 3 +1 Beds
  • 4 Baths
  • < 700 sq-ft
WELCOME TO THIS STUNNING DETACHED HOME IN THE HEART OF DESIRABLE ALLISTON! BEAUTIFULLY RENOVATED AND MOVE-IN READY, THIS BRIGHT AND SPACIOUS HOME FEAT
50 Photos
Last Updated : 4 Days ago
49 Black Creek Trail, Simcoe, ON , MLS #S13760208 , Image - 1

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49 Black Creek Trail Snow Valley, Springwater, Simcoe, ON MLS® S13760208

Residential Freehold (Detached)

$1725000.0
  • 3 +1 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Welcome to The Porches at 49 Black Creek Trail, an exceptional custom bungalow nestled in an exclusive enclave of upscale homes in sought-after Snow V
44 Photos
Last Updated : 4 Days ago
2266 Taylorwoods Boulevard, Simcoe, ON , MLS #N13702228 , Image - 1

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2266 Taylorwoods Boulevard Alcona, Innisfil, Simcoe, ON MLS® N13702228

Residential Freehold (Detached)

$859999.0
price drop iconPrice drop by 2.3%
  • 3 +1 Beds
  • 4 Baths
  • 1500-2000 sq-ft
OVER 2000 sq ft of renovated living space, Fully renovated home, LARGE lot & steps to the lake! Welcome to this stunning, fully Updated 3 + 1 Bedroom
46 Photos
Last Updated : 4 Days ago
214 Eighth Avenue, Simcoe, ON , MLS #N13789094 , Image - 1

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214 Eighth Avenue Alliston, New Tecumseth, Simcoe, ON MLS® N13789094

Residential Freehold (Detached)

$1199900.0
  • 4 Beds
  • 4 Baths
  • 3000-3500 sq-ft
Welcome to this exceptional Bedford model by Previn Court Homes, perfectly situated on a premium corner lot in one of Alliston's most desirable family
40 Photos
Last Updated : 4 Days ago
3 Best Court, Simcoe, ON , MLS #S13739186 , Image - 1

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3 Best Court Edgar, Oro-Medonte, Simcoe, ON MLS® S13739186

Residential Freehold (Detached)

$1499000.0
  • 3 +1 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Welcome to the very best of country living, just minutes from Barrie! Here's your chance to own this gorgeous custom-built home in the upscale Whisper
29 Photos
Last Updated : 4 Days ago
121 Mulcaster Street, Simcoe, ON , MLS #S13794532 , Image - 1

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121 Mulcaster Street Codrington, Barrie, Simcoe, ON MLS® S13794532

Residential Freehold (Detached)

$599000.0
  • 4 Beds
  • 2 Baths
  • 2000-2500 sq-ft
This imposing 2488 sq ft brick century home is a short walk to all of Barrie's vibrant downtown, arts and beautiful waterfront trails, parks and marin
50 Photos
Last Updated : 4 Days ago
2011 25th Side Road, Simcoe, ON , MLS #N13775064 , Image - 1

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2011 25th Side Road Alcona, Innisfil, Simcoe, ON MLS® N13775064

Residential Freehold (Detached)

$658700.0
  • 2 +2 Beds
  • 2 Baths
  • 700-1100 sq-ft
LAKE SIMCOE ACROSS THE ROAD! END-OF-ROAD PRIVACY!Welcome to 2011 25th Sideroad, the last home on the east side at the end of the road, directly across
6 Photos
Last Updated : 4 Days ago
43 Staglir Drive, Simcoe, ON , MLS #S13423876 , Image - 1

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43 Staglir Drive Rural Tiny, Tiny, Simcoe, ON MLS® S13423876

Residential Freehold (Detached)

$1575360.0
  • 4 +1 Beds
  • 4 Baths
  • 2500-3000 sq-ft
**FABULOUS BUNGALOW AWAITING YOUR TENDER LOVING CARE AND DESIGN**100FT X 150FT LOT WITH DETACHED DOUBLE GARAGE**APPROXIMATELY 5200 SF OF LIVING SPACE*
41 Photos
Last Updated : 4 Days ago
1034 Linden Street, Simcoe, ON , MLS #N13711180 , Image - 1

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1034 Linden Street Alcona, Innisfil, Simcoe, ON MLS® N13711180

Residential Freehold (Detached)

$649999.0
price drop iconPrice drop by 4.3%
  • 3 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Welcome to 1034 Linden Street, Innisfil! This spacious 3-bedroom plus den, 2-bathroom home offers nearly 1,900 sq.ft of comfortable living space, with
39 Photos
Last Updated : 4 Days ago
654 Victoria Street, Simcoe, ON , MLS #S13701214 , Image - 1

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654 Victoria Street Midland, Simcoe, ON MLS® S13701214

Residential Freehold (Detached)

$509000.0
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Perfectly positioned in a sought-after Midland neighbourhood, this home places you within easy reach of down
31 Photos
Last Updated : 4 Days ago
1046 Henry Street, Simcoe, ON , MLS #S13688394 , Image - 1

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1046 Henry Street Waverley, Tay, Simcoe, ON MLS® S13688394

Residential Freehold (Detached)

$569000.0
price drop iconPrice drop by 5.0%
  • 3 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Country Feel, Close to Everything - 2.78 Acres. If you've been looking for space, privacy and the opportunity to make a home your own, this 2.78-acre
50 Photos
Last Updated : 4 Days ago
4082 Graham Road, Simcoe, ON , MLS #S13729646 , Image - 1

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4082 Graham Road Rural Severn, Severn, Simcoe, ON MLS® S13729646

Residential Freehold (Detached)

$1875000.0
  • 5 Beds
  • 2 Baths
  • 3000-3500 sq-ft
TEA LAKE - TURN KEY AND READY TO ENJOY Imagine, Arrive, unpack and start enjoying Cottage Life. Just Bring your Groceries! 236 ft of Beautiful SOUTHER
34 Photos
Last Updated : 4 Days ago
34 Bear Creek Drive, Simcoe, ON , MLS #S13674846 , Image - 1

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34 Bear Creek Drive Holly, Barrie, Simcoe, ON MLS® S13674846

Residential Freehold (Detached)

$949000.0
price drop iconPrice drop by 4.6%
  • 4 +1 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Completely Renovated , 3,500+ Sq. Ft. ,Premium Family Location. Welcome to 34 Bear Creek Drive - A stunning, completely renovated home offering over 3
26 Photos
Last Updated : 4 Days ago
25 Marshall Street, Simcoe, ON , MLS #S13794272 , Image - 1

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25 Marshall Street Allandale Heights, Barrie, Simcoe, ON MLS® S13794272

Residential Freehold (Detached)

$599000.0
  • 4 Beds
  • 3 Baths
  • 1500-2000 sq-ft
UBID HOME FOR SALE. HOMEOWNER RELOCATING ($599,000) Welcome to 25 Marshall Street, where style, space and everyday comfort come together. Offering ove
39 Photos
Last Updated : 4 Days ago
46 Kraus Road, Simcoe, ON , MLS #S13794232 , Image - 1

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46 Kraus Road Edgehill Drive, Barrie, Simcoe, ON MLS® S13794232

Residential Freehold (Detached)

$699000.0
  • 3 +2 Beds
  • 4 Baths
  • 1500-2000 sq-ft
Welcome to 46 Kraus Road, Barrie, a beautifully renovated home ( $200K in last few Years) in the desirable Edgehill Drive neighbourhood with 1986 sqf
13 Photos
Last Updated : 4 Days ago
37 Bedford Estates Crescent, Simcoe, ON , MLS #S13421204 , Image - 1

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37 Bedford Estates Crescent Bayshore, Barrie, Simcoe, ON MLS® S13421204

Residential Freehold (Detached)

$639900.0
price drop iconPrice drop by 1.5%
  • 3 +1 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Welcome to 37 Bedford Estates Cres. Nestled on a quiet family-friendly cul-de-sac in Barrie's desirable south end, this beautiful detached home offers
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