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Detached Houses for Sale in Simcoe Under $500K - P8

Showing results 211 - 240 of 251
Last Updated: September 20, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
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20 Photos
Last Updated : 54 Days ago
60 Laidlaw Street, Simcoe, ON , MLS #S13612942 , Image - 1
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60 Laidlaw Street Wasaga Beach, Simcoe, ON MLS® S13612942

Residential Freehold (Detached)

$399900.0
  • 2 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
BUNGALOW WITHIN WALKING DISTANCE OF THE BEACH WITH A HEATED BUNKIE, MATURE TREES & A GENEROUS 60 X 125 FT LOT! Just a 10-minute walk from Wasaga's bea
8 Photos
Last Updated : 54 Days ago
418 Dominion Avenue, Simcoe, ON , MLS #S13445334 , Image - 1

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418 Dominion Avenue Midland, Simcoe, ON MLS® S13445334

Residential Freehold (Detached)

$499990.0
price drop iconPrice drop by 15.3%
  • 7 +1 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Rare opportunity to own a spacious Victorian-style home in the heart of Midland with views of beautiful Georgian Bay. Offering approximately 3,000 sq.
9 Photos
Last Updated : 54 Days ago
354 Midland Avenue, Simcoe, ON , MLS #S13436614 , Image - 1

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354 Midland Avenue Midland, Simcoe, ON MLS® S13436614

Residential Freehold (Detached)

$399990.0
price drop iconPrice drop by 16.7%
  • 5 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Perfect investment live in and run your business from this property, many of the commercial elements done, perfect for any type of office, Insurance,
27 Photos
Last Updated : 55 Days ago
341 Tiny Beaches Road N, Simcoe, ON , MLS #S13586334 , Image - 1

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341 Tiny Beaches Road N Rural Tiny, Tiny, Simcoe, ON MLS® S13586334

Residential Freehold (Detached)

$495000.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Charming and Traditional 3 Bedroom Summer Cottage Between Walker's Beach. 200 meters to Cawaja Sandy Beach and 400 meters to Rowntree Beach. A Great P
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
30 Photos
Last Updated : 57 Days ago
2135 Champlain Road, Simcoe, ON , MLS #S13604942 , Image - 1

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2135 Champlain Road Rural Tiny, Tiny, Simcoe, ON MLS® S13604942

Residential Freehold (Detached)

$449000.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Visit the REALTOR website for further information about this Listing. Year-round home or cottage in a natural setting, near Sawlog Point in Tiny. 2 B
27 Photos
Last Updated : 58 Days ago
2678 25th Side Road, Simcoe, ON , MLS #N13074692 , Image - 1

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2678 25th Side Road Rural Innisfil, Innisfil, Simcoe, ON MLS® N13074692

Residential Freehold (Detached)

$425000.0
price drop iconPrice drop by 9.6%
  • 1 Beds
  • 1 Baths
  • 700-1100 sq-ft
A rare opportunity to live and build in beautiful Innisfil Beach. This oversized lot of 50 X 200 feet with and approximate 700 sq ft bungalow frame fe
41 Photos
Last Updated : 59 Days ago
45 Andrew Drive, Simcoe, ON , MLS #S13469628 , Image - 1

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45 Andrew Drive Rural Tiny, Tiny, Simcoe, ON MLS® S13469628

Residential Freehold (Detached)

$499000.0
price drop iconPrice drop by 3.9%
  • 2 Beds
  • 1 Baths
  • < 700 sq-ft
Excellent four season bungalow offering an affordable entry into a highly desirable lakeside community. Situated in a quiet area of Rural Tiny, this d
15 Photos
Last Updated : 60 Days ago
9 Wolfe Street, Simcoe, ON , MLS #S13571870 , Image - 1

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9 Wolfe Street Penetanguishene, Simcoe, ON MLS® S13571870

Residential Freehold (Detached)

$399900.0
  • 4 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Welcome to 9 Wolfe Street in the heart of Penetanguishene! This spacious bungalow offers exceptional potential for first-time buyers, families, or inv
31 Photos
Last Updated : 62 Days ago
20 Marilyn Avenue N, Simcoe, ON , MLS #S13489146 , Image - 1

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20 Marilyn Avenue N Wasaga Beach, Simcoe, ON MLS® S13489146

Residential Freehold (Detached)

$399000.0
price drop iconPrice drop by 11.1%
  • 3 +0 Beds
  • 1 Baths
  • 700-1100 sq-ft
This cottage has been owned by the same family since 2005 .There are two water and two sewer connections. This cottage sits on a large triangular
21 Photos
Last Updated : 62 Days ago
30 Illinois Crescent, Simcoe, ON , MLS #S13558966 , Image - 1

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30 Illinois Crescent Wasaga Beach, Simcoe, ON MLS® S13558966

Residential Freehold (Detached)

$479000.0
  • 2 +0 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Welcome to 30 Illinois Crescent, nestled in the heart of Park Place Estates. Wasaga Beach's premier 55+ gated community, where comfort, connection, an
20 Photos
Last Updated : 65 Days ago
36 Sanford Street, Simcoe, ON , MLS #S13579022 , Image - 1

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36 Sanford Street Sanford, Barrie, Simcoe, ON MLS® S13579022

Residential Freehold (Detached)

$499900.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
BARRIE BUNGALOW! Welcome to this charming move-in ready 3-bedroom, 1-bath bungalow in a desirable Barrie neighbourhood. Bright and inviting, this wel
14 Photos
Last Updated : 65 Days ago
117 Fox Street, Simcoe, ON , MLS #S13577448 , Image - 1

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117 Fox Street Penetanguishene, Simcoe, ON MLS® S13577448

Residential Freehold (Detached)

$323000.0
  • 4 Beds
  • 1 Baths
  • 1500-2000 sq-ft
Prime Investment in Penetanguishene Attention investors and flippers! This solid 4-bedroom home sits on an impressive 0.54-acre lot (89 ft x 264 ft),
30 Photos
Last Updated : 66 Days ago
224 Tiny Beaches Road S Road, Simcoe, ON , MLS #S13568156 , Image - 1

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224 Tiny Beaches Road S Road Rural Tiny, Tiny, Simcoe, ON MLS® S13568156

Residential Freehold (Detached)

$424900.0
  • 1 Beds
  • 1 Baths
  • < 700 sq-ft
Imagine waking up just steps from the soft sands of Georgian Bay, coffee in hand, with the sound of the waves calling you to the beach. Welcome to you
26 Photos
Last Updated : 67 Days ago
8 Arbor Road, Simcoe, ON , MLS #S13565114 , Image - 1

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8 Arbor Road Rural Tiny, Tiny, Simcoe, ON MLS® S13565114

Residential Freehold (Detached)

$489900.0
  • 2 Beds
  • 1 Baths
  • < 700 sq-ft
YEAR-ROUND, FULLY WINTERIZED HOME/COTTAGE JUST STEPS TO THE BEACH! Located in the highly sought-after Balm Beach, this charming property offers the pe
32 Photos
Last Updated : 68 Days ago
101 Tecumseth Pines Drive, Simcoe, ON , MLS #N13561798 , Image - 1

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101 Tecumseth Pines Drive Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13561798

Residential Freehold (Detached)

$469900.0
  • 2 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
Enjoy the carefree-living adult lifestyle that awaits you at Tecumseth Pines just minutes from Tottenham, where residents can enjoy a range of ameniti
18 Photos
Last Updated : 69 Days ago
48 Mcarthur Drive, Simcoe, ON , MLS #S13455582 , Image - 1

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48 Mcarthur Drive Penetanguishene, Simcoe, ON MLS® S13455582

Residential Freehold (Detached)

$398000.0
price drop iconPrice drop by 6.3%
  • 1 Beds
  • 1 Baths
  • < 700 sq-ft
Location, location! This Charming turn key, open concept cottage, located in prestigious waterfront community, is within minutes walk to nearby beac
35 Photos
Last Updated : 70 Days ago
81 Andrew Drive, Simcoe, ON , MLS #S13520760 , Image - 1

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81 Andrew Drive Rural Tiny, Tiny, Simcoe, ON MLS® S13520760

Residential Freehold (Detached)

$429900.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to your perfect four-season retreat across the road from beautiful Farlain Lake! Whether you're searching for a year-round home or a cozy cott
50 Photos
Last Updated : 70 Days ago
118 Tecumseth Pines Drive, Simcoe, ON , MLS #N13553454 , Image - 1

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118 Tecumseth Pines Drive Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13553454

Residential Freehold (Detached)

$469000.0
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to Carefree Living in this Meticulously Maintained 2 Bedroom Detached Home in a Sought-After Adult Lifestyle Community in Rural New Tecumseth.
8 Photos
Last Updated : 72 Days ago
1274 Killarney Beach Road, Simcoe, ON , MLS #N13546298 , Image - 1

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1274 Killarney Beach Road Lefroy, Innisfil, Simcoe, ON MLS® N13546298

Residential Freehold (Detached)

$469000.0
  • 4 Beds
  • 1 Baths
  • 700-1100 sq-ft
10 Photos
Last Updated : 73 Days ago
310 Maple Street, Simcoe, ON , MLS #S13518402 , Image - 1

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310 Maple Street Collingwood, Simcoe, ON MLS® S13518402

Residential Freehold (Detached)

$449000.0
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Walk to Downtown Collingwood!Endless potential awaits on this premium 28.8' x 165' deep lot, located steps from downtown Collingwood's shops, cafes, a
24 Photos
Last Updated : 74 Days ago
91.5 KING Road, Simcoe, ON , MLS #S13538398 , Image - 1

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91.5 KING Road Waubaushene, Tay, Simcoe, ON MLS® S13538398

Residential Freehold (Detached)

$119900.0
  • 2 +0 Beds
  • 1 Baths
  • < 700 sq-ft
TINY HOME ONLY! IT DOES NOT COME WITH THE LAND AND NEEDS TO BE MOVED TO YOUR OWN PROPERTY! Welcome to one of today's unique options for a year-round b
45 Photos
Last Updated : 75 Days ago
13 WHITE PINES Trail, Simcoe, ON , MLS #S13492930 , Image - 1

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13 WHITE PINES Trail Wasaga Beach, Simcoe, ON MLS® S13492930

Residential Freehold (Detached)

$179900.0
  • 1 Beds
  • 2 Baths
  • 700-1100 sq-ft
Welcome to 13 White Pines Trail in the highly sought-after Wasaga CountryLife Resort, offering an exceptional blend of craftsmanship, comfort, and wat
1 Photos
Last Updated : 79 Days ago
43 Ridge Avenue, Simcoe, ON
43 Ridge Avenue Rural Ramara, Ramara, Simcoe, ON MLS® S13516746

Residential Freehold (Detached)

$425000.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to Lagoon City-a unique community featuring a canal system and direct access to Lake Simcoe. Situated on a picturesque waterfront lot, this pr
50 Photos
Last Updated : 79 Days ago
56 TECUMSETH PINES Drive, Simcoe, ON , MLS #N13516582 , Image - 1

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56 TECUMSETH PINES Drive Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13516582

Residential Freehold (Detached)

$439900.0
  • 2 +0 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to Tecumseth Pines - A premier residential retirement community with a stunning landscape and friendly atmosphere! Lot 56 features a 2 bedroom
48 Photos
Last Updated : 85 Days ago
36 Tecumseth Pines Drive, Simcoe, ON , MLS #N13496326 , Image - 1

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36 Tecumseth Pines Drive Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13496326

Residential Freehold (Detached)

$449000.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to Tecumseth Pines, where peaceful country surroundings meet an active and welcoming 55+ lifestyle! Nestled in a beautiful community just minu
21 Photos
Last Updated : 90 Days ago
25 Balmoral Avenue, Simcoe, ON , MLS #S13475982 , Image - 1

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25 Balmoral Avenue Rural Tiny, Tiny, Simcoe, ON MLS® S13475982

Residential Freehold (Detached)

$499000.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Escape to your own slice of paradise with this charming rustic cottage! Perched high and dry overlooking a treed 240-foot deep lot, this property offe
45 Photos
Last Updated : 100 Days ago
1 WHITE PINES Trail, Simcoe, ON , MLS #S13436258 , Image - 1

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1 WHITE PINES Trail Wasaga Beach, Simcoe, ON MLS® S13436258

Residential Freehold (Detached)

$169900.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Nestled within the sought-after Wasaga CountryLife Resort, this charming woodland Park Muskoka at 1 White Pines Trail offers a rare blend of privacy,
4 Photos
Last Updated : 102 Days ago
339 Gill Street, Simcoe, ON , MLS #S13185992 , Image - 1
339 Gill Street Orillia, Simcoe, ON MLS® S13185992

Residential Freehold (Detached)

$499990.0
  • < 700 sq-ft
Welcome To 339 Gill Street! This Corner Property Is One Of A Kind! Suitable For Many Uses Including An Apartment Building Or A Townhouse Project. R2 Z
35 Photos
Last Updated : 102 Days ago
61 Pennsylvania Avenue, Simcoe, ON , MLS #S13425860 , Image - 1

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61 Pennsylvania Avenue Wasaga Beach, Simcoe, ON MLS® S13425860

Residential Freehold (Detached)

$439000.0
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Discover the thoughtfully updated two-bedroom bungalow in the sought-after 55+ Park Place community in the h
4 Photos
Last Updated : 104 Days ago
2766 Ireton Street, Simcoe, ON , MLS #N13412556 , Image - 1
2766 Ireton Street Rural Innisfil, Innisfil, Simcoe, ON MLS® N13412556

Residential Freehold (Detached)

$444900.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Reduced Price!! Incredible opportunity to build your dream home or cottage retreat on a premium lot just steps from one of Innisfil's most beautiful b
Shortlisted Properties
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