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Detached Houses for Sale in Simcoe Under $500K - P4

Showing results 91 - 120 of 233
Last Updated: August 06, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
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33 Photos
Last Updated : 9 Days ago
3 Golf Avenue, Simcoe, ON , MLS #S13226438 , Image - 1
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3 Golf Avenue Wasaga Beach, Simcoe, ON MLS® S13226438

Residential Freehold (Detached)

$309900.0
price drop iconPrice drop by 2.9%
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Very well cared for and beautifully maintained bungalow with 2 bdrms, a renovated bath and beautiful big kitchen open to the tidy, bright living room
50 Photos
Last Updated : 11 Days ago
337 Colborne Street W, Simcoe, ON , MLS #S13222012 , Image - 1

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337 Colborne Street W Orillia, Simcoe, ON MLS® S13222012

Residential Freehold (Detached)

$395000.0
price drop iconPrice drop by 14.1%
  • 3 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Charming West Ward Opportunity - Perfect for First-Time Buyers or InvestorsWelcome to this well-loved 3-bedroom, 1-storey home located in Orillia's We
10 Photos
Last Updated : 12 Days ago
6583 Pioneer Village Line, Simcoe, ON , MLS #S13066072 , Image - 1

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6583 Pioneer Village Line Rural Ramara, Ramara, Simcoe, ON MLS® S13066072

Residential Freehold (Detached)

$399500.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Perfect reno opportunity for a team of trades or couple. Great bones ..some roof repair needed. All furniture will stay except bedding and person
30 Photos
Last Updated : 12 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
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
31 Photos
Last Updated : 12 Days ago
7 Tamarack Court, Simcoe, ON , MLS #N13448478 , Image - 1

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7 Tamarack Court Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13448478

Residential Freehold (Detached)

$424900.0
price drop iconPrice drop by 9.6%
  • 2 Beds
  • 2 Baths
  • 700-1100 sq-ft
A rare find in Tecumseth Pines - a must see bright and beautifully updated bungalow where the major work has already been done! Located on a sunny sou
40 Photos
Last Updated : 12 Days ago
680 Ontario Street, Simcoe, ON , MLS #S13602160 , Image - 1

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680 Ontario Street Midland, Simcoe, ON MLS® S13602160

Residential Freehold (Detached)

$474900.0
  • 3 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Welcome to the heart of Midland! Situated on an impressive lot 104 ft x 50 ft (double lot frontage), this beautifully updated home offers exceptional
24 Photos
Last Updated : 12 Days ago
120 Maple Street, Simcoe, ON , MLS #S13148258 , Image - 1

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120 Maple Street Victoria Harbour, Tay, Simcoe, ON MLS® S13148258

Residential Freehold (Detached)

$399999.0
price drop iconPrice drop by 4.5%
  • 4 Beds
  • 2 Baths
  • 700-1100 sq-ft
Ideal for investors, renovators, or buyers looking to live in and customize! Welcome to 120 Maple St in Tay - a great opportunity on a large 132 x 160
12 Photos
Last Updated : 12 Days ago
26 George Avenue, Simcoe, ON , MLS #S13603444 , Image - 1

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26 George Avenue Wasaga Beach, Simcoe, ON MLS® S13603444

Residential Freehold (Detached)

$349900.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Opportunity Knocks! Attention Renovators, Contractors, Investors, Builders And First Time Buyers. 3 Bedroom Bungalow Located On A Quiet Cul-De Sac. Ki
39 Photos
Last Updated : 12 Days ago
1 Tecumseth Pines Drive, Simcoe, ON , MLS #N13475370 , Image - 1

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1 Tecumseth Pines Drive Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13475370

Residential Freehold (Detached)

$449994.0
price drop iconPrice drop by 5.3%
  • 3 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Welcome to 1 Tecumseth Pines, a beautifully maintained home in one of Simcoe's most sought-after adult lifestyle communities. Perfectly located close
30 Photos
Last Updated : 12 Days ago
51 Leggott Avenue, Simcoe, ON , MLS #S13549500 , Image - 1

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51 Leggott Avenue Painswick North, Barrie, Simcoe, ON MLS® S13549500

Residential Freehold (Detached)

$499000.0
  • 3 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Welcome to this exceptional opportunity to own a spacious family home in the highly sought-after Painswick North community of Barrie. Offered as a Pow
6 Photos
Last Updated : 12 Days ago
10 Rhonda Road, Simcoe, ON , MLS #S13455332 , Image - 1

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10 Rhonda Road Collingwood, Simcoe, ON MLS® S13455332

Residential Freehold (Detached)

$299000.0
price drop iconPrice drop by 9.4%
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
PROPERTY IS CONDITIONALLY SOLD. Attention Developers, Builders, and Investors! Rare opportunity to redevelop, rehabilitate, or reimagine a fully serv
37 Photos
Last Updated : 12 Days ago
320 Scott Street, Simcoe, ON , MLS #S13538324 , Image - 1

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320 Scott Street Midland, Simcoe, ON MLS® S13538324

Residential Freehold (Detached)

$495000.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
This well-kept 3-bedroom, 1-bathroom all-brick backsplit offers a great family-friendly layout in a central Midland location. The main level features
27 Photos
Last Updated : 12 Days ago
225 Park Street, Simcoe, ON , MLS #S13476298 , Image - 1

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225 Park Street Victoria Harbour, Tay, Simcoe, ON MLS® S13476298

Residential Freehold (Detached)

$409900.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Attention investors, renovators, and first-time buyers! This 2-bedroom bungalow in the heart of Victoria Harbour presents an excellent opportunity to
30 Photos
Last Updated : 12 Days ago
308 Russell Street, Simcoe, ON , MLS #S13601082 , Image - 1

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308 Russell Street Midland, Simcoe, ON MLS® S13601082

Residential Freehold (Detached)

$389900.0
  • 3 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Bright, custom-designed kitchen thoughtfully crafted for both style and functionality, with an abundance of
39 Photos
Last Updated : 12 Days ago
110 24TH Street N, Simcoe, ON , MLS #S13600934 , Image - 1

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110 24TH Street N Wasaga Beach, Simcoe, ON MLS® S13600934

Residential Freehold (Detached)

$439000.0
  • 3 +0 Beds
  • 1 Baths
  • 700-1100 sq-ft
This three-bedroom home or cottage is ideally situated north of Mosley Street in highly sought-after Area 4, just a five-minute walk to the sandy shor
20 Photos
Last Updated : 13 Days ago
54 Homewood Avenue, Simcoe, ON , MLS #S13451232 , Image - 1

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54 Homewood Avenue Wasaga Beach, Simcoe, ON MLS® S13451232

Residential Freehold (Detached)

$389000.0
price drop iconPrice drop by 8.0%
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Cottage Life on Georgian Bay-what does it mean to you? Is it an easy stroll to New Wasaga Beach or cozy nights by the fire with sand between your toes
27 Photos
Last Updated : 13 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
39 Photos
Last Updated : 13 Days ago
10 Brookside Drive, Simcoe, ON , MLS #S13596848 , Image - 1

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10 Brookside Drive Rural Tiny, Tiny, Simcoe, ON MLS® S13596848

Residential Freehold (Detached)

$499999.0
  • 2 +1 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to 10 Brookside Drive, where the best of Georgian Bay's beach lifestyle is right at your doorstep. A two-minute walk to the stunning sandy sho
28 Photos
Last Updated : 13 Days ago
11 Tamarack Court, Simcoe, ON , MLS #N13589138 , Image - 1

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11 Tamarack Court Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13589138

Residential Freehold (Detached)

$449000.0
price drop iconPrice drop by 15.1%
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to Tecumseth Pines, a welcoming 55+ land-lease community known for its peaceful setting and active lifestyle. This Cypress-model bungalow sits
31 Photos
Last Updated : 13 Days ago
4 St James Place, Simcoe, ON , MLS #S13081644 , Image - 1

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4 St James Place Wasaga Beach, Simcoe, ON MLS® S13081644

Residential Freehold (Detached)

$319000.0
price drop iconPrice drop by 14.9%
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Amazing opportunity to own a fully detached home in Park Place, one of Wasaga Beach's premier adult retirement land lease communities. Lovely 2 bedroo
41 Photos
Last Updated : 13 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
20 Photos
Last Updated : 13 Days ago
1053 Glen Bogie Crescent, Simcoe, ON , MLS #S13597252 , Image - 1

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1053 Glen Bogie Crescent Midland, Simcoe, ON MLS® S13597252

Residential Freehold (Detached)

$499900.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to Midland's most sought-after west end neighbourhood, where mature trees, quiet streets, and long-time residents create a true sense of commu
28 Photos
Last Updated : 13 Days ago
379 Gloucester Street, Simcoe, ON , MLS #S13542010 , Image - 1

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379 Gloucester Street Midland, Simcoe, ON MLS® S13542010

Residential Freehold (Detached)

$299777.0
  • 2 +0 Beds
  • 1 Baths
  • 1500-2000 sq-ft
Welcome to 379 Gloucester Street in Midland, a fantastic opportunity for first-time buyers, investors, or anyone looking for a rewarding renovation pr
37 Photos
Last Updated : 14 Days ago
23 Maria Street, Simcoe, ON , MLS #S13251390 , Image - 1

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23 Maria Street Penetanguishene, Simcoe, ON MLS® S13251390

Residential Freehold (Detached)

$399000.0
price drop iconPrice drop by 4.8%
  • 3 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Endless Potential Meets Small-Town Charm On A Large Lot At 23 Maria Street In The Heart Of Penetanguishene. This 3-Bedroom, 1-Bathroom Home Presents A
4 Photos
Last Updated : 14 Days ago
8926 Mckinnon Road, Simcoe, ON , MLS #N13486348 , Image - 1
8926 Mckinnon Road Rural Essa, Essa, Simcoe, ON MLS® N13486348

Residential Freehold (Detached)

Price On Request
  • 4 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Once-in-a-generation opportunity on 24 acres in fast-growing Angus. A solid 4-bedroom detached home anchors the property today, while approximately 10
15 Photos
Last Updated : 14 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
21 Photos
Last Updated : 14 Days ago
3433 Beachview Avenue, Simcoe, ON , MLS #S13584470 , Image - 1

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3433 Beachview Avenue West Shore, Severn, Simcoe, ON MLS® S13584470

Residential Freehold (Detached)

$475000.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Freshly refurbished bungalow perfect for a couple starting out or retiring who are looking for a garage, outdoor space and a cottage-sized, move in co
30 Photos
Last Updated : 14 Days ago
5263 Elliott Side Road, Simcoe, ON , MLS #S13592224 , Image - 1

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Unit-5, 5263 Elliott Side Road Rural Tay, Tay, Simcoe, ON MLS® S13592224

Residential Freehold (Detached)

$220000.0
  • 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
14 Photos
Last Updated : 14 Days ago
857 Birchwood Drive, Simcoe, ON , MLS #S13537548 , Image - 1

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857 Birchwood Drive Midland, Simcoe, ON MLS® S13537548

Residential Freehold (Detached)

$449000.0
  • 3 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
SUN-FILLED BUNGALOW LIVING JUST MINUTES FROM MIDLAND'S WATERFRONT! Escape to a peaceful, tree-lined neighbourhood where quiet streets, mature trees, a
23 Photos
Last Updated : 15 Days ago
8 Myrtle Avenue, Simcoe, ON , MLS #S13578972 , Image - 1

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8 Myrtle Avenue Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13578972

Residential Freehold (Detached)

$499900.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Fully Renovated From Top To Bottom Over The Last 5 Years! Completely Turn-Key, Cozy Bungalow Situated On Large 50 x 110 Ft Lot With No Neighbours Behi
Shortlisted Properties
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