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Houses for Sale in Simcoe Under $500K - P2

Showing results 31 - 60 of 1114
Last Updated: September 27, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
  • Square Feet(Lo-Hi)
  • Square Feet(Hi-Lo)
34 Photos
Last Updated : 2 Days ago
14 Butternut Court, Simcoe, ON , MLS #N13470288 , Image - 1
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14 Butternut Court Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13470288

Residential Freehold (Detached)

$398500.0
price drop iconPrice drop by 4.9%
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
When people consider resizing to the Tecumseth Pines Adult Community, they look at many of the same features, however one that is often given higher c
29 Photos
Last Updated : 2 Days ago
65 Ellen Street, Simcoe, ON , MLS #S13831392 , Image - 1

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Unit-1005, 65 Ellen Street City Centre, Barrie, Simcoe, ON MLS® S13831392

Residential Condo & Other (Condo Apartment)

$439000.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Welcome to waterfront living in Barrie's sought-after Marina Bay community! This spacious 10th-floor, 2-bedroom, 2-bathroom suite offers a wonderful
25 Photos
Last Updated : 2 Days ago
140 Dunlop Street E, Simcoe, ON , MLS #S13751624 , Image - 1

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Unit-1003, 140 Dunlop Street E City Centre, Barrie, Simcoe, ON MLS® S13751624

Residential Condo & Other (Condo Apartment)

$324900.0
price drop iconPrice drop by 7.1%
  • 1 +1 Beds
  • 1 Baths
  • 700-799 sq-ft
Welcome to Suite 1003 at Bayshore Landing, where waterfront living meets vibrant downtown convenience. This beautifully updated 1-bedroom and den cond
11 Photos
Last Updated : 2 Days ago
1327 Monck Road, Simcoe, ON , MLS #S13746958 , Image - 1

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1327 Monck Road Rural Ramara, Ramara, Simcoe, ON MLS® S13746958

Residential Freehold (Vacant Land)

$149900.0
Located in a secluded countryside setting, this prime 1.57-acre wooded lot offers the perfect canvas to build your dream home or rural retreat. Featur
Pre-Construction
Rosehaven Simcoe Woods
6 Photos

Rosehaven Simcoe Woods

Innisfil Beach Road & Webster Boulevard
From $879,990 - $1,339,990
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Project Info
  • Units
  • Townhouses
building outline
Property Mix
Floorplans coming soon
Developer:Rosehaven Homes
16 Photos
Last Updated : 2 Days ago
63 Ferris Lane, Simcoe, ON , MLS #S13722792 , Image - 1

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63 Ferris Lane
Unit-B1, 63 Ferris Lane Cundles East, Barrie, Simcoe, ON MLS® S13722792

Residential Condo & Other (Condo Townhouse)

$369990.0
  • 3 Beds
  • 2 Baths
  • 1000-1199 sq-ft
LOW-MAINTENANCE LIVING WITH THOUGHTFUL UPDATES! 63 Ferris Lane B1 is a thoughtfully updated 2-storey end-unit condo townhome in Barrie's north end, of
38 Photos
Last Updated : 2 Days ago
183 Paradise Avenue, Simcoe, ON , MLS #S13127128 , Image - 1

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183 Paradise Avenue Port McNicoll, Tay, Simcoe, ON MLS® S13127128

Residential Freehold (Detached)

$379000.0
price drop iconPrice drop by 5.2%
  • 3 Beds
  • 1 Baths
  • < 700 sq-ft
Welcome to 183 Paradise Avenue, this 3-bedroom, 1-bath home located in the heart of beautiful Port McNicoll. Just minutes from the waterfront, this pr
9 Photos
Last Updated : 2 Days ago
6569 Rama Road, Simcoe, ON , MLS #S12370323 , Image - 1

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6569 Rama Road Rural Ramara, Ramara, Simcoe, ON MLS® S12370323

Residential Freehold (Detached)

$450000.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
This approximately 800 sq. ft. bungalow sits nestled amongst mature maple and oak trees that provide privacy and tranquility that your family will app
30 Photos
Last Updated : 2 Days ago
435 Walnut Street, Simcoe, ON , MLS #S13827436 , Image - 1

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Unit-101, 435 Walnut Street Collingwood, Simcoe, ON MLS® S13827436

Residential Condo & Other (Condo Apartment)

$379000.0
  • 1 Beds
  • 1 Baths
  • 800-899 sq-ft
Welcome to the desirable WALNUT WOODS condominium community, a well-maintained 16-unit brick building perfectly located in the heart of Collingwood. T
24 Photos
Last Updated : 2 Days ago
3301 Pleasant Road, Simcoe, ON , MLS #S13674698 , Image - 1

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3301 Pleasant Road West Shore, Severn, Simcoe, ON MLS® S13674698

Residential Freehold (Detached)

$449900.0
  • 2 Beds
  • 1 Baths
  • < 700 sq-ft
A great opportunity for first-time buyers! Located in Severn, just 10 minutes from Orillia with easy highway access, this well-maintained home sits on
26 Photos
Last Updated : 2 Days ago
299 Cundles Road E, Simcoe, ON , MLS #S13827640 , Image - 1

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Unit-505, 299 Cundles Road E 400 North, Barrie, Simcoe, ON MLS® S13827640

Residential Condo & Other (Condo Apartment)

$415900.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Welcome to Suite 505 at 299 Cundles Road East, a spacious and beautifully positioned 1,060 sq. ft. residence offering 2 bedrooms, 2 bathrooms and an i
10 Photos
Last Updated : 2 Days ago
681 Yonge Street, Simcoe, ON , MLS #S13819840 , Image - 1

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Unit-322, 681 Yonge Street Painswick South, Barrie, Simcoe, ON MLS® S13819840

Residential Condo & Other (Condo Apartment)

$425000.0
  • 1 +1 Beds
  • 1 Baths
  • 700-799 sq-ft
Welcome to one of Barrie's highly sought-after South District Condos! This bright south-facing**1 Bedroom + Den, 1 Bathroom** suite features an open-c
24 Photos
Last Updated : 2 Days ago
20 Koda Street, Simcoe, ON , MLS #S13830478 , Image - 1

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Unit-109, 20 Koda Street Rural Barrie Southwest, Barrie, Simcoe, ON MLS® S13830478

Residential Condo & Other (Condo Apartment)

$399000.0
  • 1 Beds
  • 1 Baths
  • 700-799 sq-ft
Welcome to 20 Koda St, Unit 109, located in the highly sought-after Bear Creek Ridge community! This beautifully designed condo offers an exceptional
18 Photos
Last Updated : 2 Days ago
317 Wardell Street, Simcoe, ON , MLS #S13619686 , Image - 1

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317 Wardell Street Port McNicoll, Tay, Simcoe, ON MLS® S13619686

Residential Freehold (Detached)

$457900.0
price drop iconPrice drop by 4.6%
  • 3 +0 Beds
  • 1 Baths
  • 700-1100 sq-ft
This newly renovated move-in ready home is a gem and ready to make it your own. Set on a large lot with a double detached garage that has heat and hy
6 Photos
Last Updated : 2 Days ago
LT 49 Whispering Pine Circle E, Simcoe, ON , MLS #S13246422 , Image - 1

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LT 49 Whispering Pine Circle E Rural Tiny, Tiny, Simcoe, ON MLS® S13246422

Residential Freehold (Vacant Land)

$260000.0
price drop iconPrice drop by 5.5%
Treed building cul-de-sac lot situated in Rural Tiny, less than a 10 minute drive to town/amenities. Build your dream home here, enjoy the benefits of
14 Photos
Last Updated : 2 Days ago
Lot 14 Concession 18 Road W, Simcoe, ON , MLS #S13427196 , Image - 1

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Lot 14 Concession 18 Road W Rural Tiny, Tiny, Simcoe, ON MLS® S13427196

Residential Freehold (Vacant Land)

$149900.0
price drop iconPrice drop by 44.5%
Discover 45 acres of natural beauty in Tiny Township. This wooded property features a mix of hardwood and softwood trees, creating a peaceful setting
29 Photos
Last Updated : 2 Days ago
12 Briarwood Place, Simcoe, ON , MLS #N13533472 , Image - 1

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12 Briarwood Place Cookstown, Innisfil, Simcoe, ON MLS® N13533472

Residential Freehold (Modular Home)

$389000.0
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to Royal Oak Estates. This Senior (Age 55+) Land Lease Community is in the heart of Cookstown.Just a short walk from the SHops and Restaurants
38 Photos
Last Updated : 2 Days ago
21 Laguna Parkway, Simcoe, ON , MLS #S13806418 , Image - 1

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Unit-# 21, 21 Laguna Parkway Brechin, Ramara, Simcoe, ON MLS® S13806418

Residential Condo & Other (Condo Townhouse)

$429900.0
  • 3 Beds
  • 3 Baths
  • 1400-1599 sq-ft
Welcome to 21 Laguna Pkwy - Lakeside Community Living at Its Best! Discover beautifullymaintained, maintenance-free living in this charming 3-bedroom,
32 Photos
Last Updated : 2 Days ago
8 Culinary Lane, Simcoe, ON , MLS #S13827900 , Image - 1

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8 Culinary Lane
Unit-604, 8 Culinary Lane Rural Barrie Southeast, Barrie, Simcoe, ON MLS® S13827900

Residential Condo & Other (Condo Apartment)

$455000.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
This is the one! A beautifully upgraded top floor condo designed for comfortable, low maintenance living. With western exposure and no neighbours abov
Open House : Sat Oct 03, 11:00 AM to 01:00 PM
4 Photos
Last Updated : 2 Days ago
242 Barnett Avenue, Simcoe, ON , MLS #S13799500 , Image - 1
242 Barnett Avenue Midland, Simcoe, ON MLS® S13799500

Residential Freehold (Detached)

$494000.0
price drop iconPrice drop by 3.1%
  • 4 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Exceptional opportunity in Midland! Situated on an expensive double lot with impressive 97.44' frontage by 123.50' depth, this 2-storey home offers in
10 Photos
Last Updated : 2 Days ago
179 Edgehill Drive, Simcoe, ON , MLS #S13830106 , Image - 1

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Unit-B7, 179 Edgehill Drive Letitia Heights, Barrie, Simcoe, ON MLS® S13830106

Residential Condo & Other (Condo Apartment)

$299500.0
  • 2 Beds
  • 1 Baths
  • 700-799 sq-ft
Enjoy comfortable, low-maintenance living in this bright and inviting 2-bedroom, 1-bathroom condo in Barrie, offering approximately 790 sq. ft. of fun
24 Photos
Last Updated : 2 Days ago
179 Seventh Street, Simcoe, ON , MLS #S13824824 , Image - 1

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179 Seventh Street Midland, Simcoe, ON MLS® S13824824

Residential Freehold (Detached)

$369900.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Enjoy quiet mornings on the welcoming front porch or relaxing evenings on the private rear deck. With three bedrooms and 1 bath this century home is i
7 Photos
Last Updated : 2 Days ago
Lot 514 Tall Pines Drive, Simcoe, ON , MLS #S13078030 , Image - 1

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Lot 514 Tall Pines Drive Rural Tiny, Tiny, Simcoe, ON MLS® S13078030

Residential Freehold (Vacant Land)

$219000.0
price drop iconPrice drop by 12.0%
WORK AND PLAY IN GEORGIAN BAY! BUILD YOUR DREAM HOME AT THE BEACH! This vacant partially cleared lot has a 20 Ft easement and is a Short Walk to Georg
16 Photos
Last Updated : 2 Days ago
241 Sea Ray Avenue, Simcoe, ON , MLS #N13829902 , Image - 1

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Unit-A101, 241 Sea Ray Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N13829902

Residential Condo & Other (Condo Apartment)

$498888.0
  • 2 Beds
  • 2 Baths
  • 800-899 sq-ft
This is your chance to own a slice of luxury vacation living, just one hour from the GTA. Whether you're looking for a full-time home, weekend escape,
34 Photos
Last Updated : 2 Days ago
67 Fittons Road E, Simcoe, ON , MLS #S13829864 , Image - 1

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Unit-18, 67 Fittons Road E Orillia, Simcoe, ON MLS® S13829864

Residential Condo & Other (Condo Townhouse)

$379900.0
  • 4 Beds
  • 2 Baths
  • 1200-1399 sq-ft
Discover an exceptional opportunity for first-time buyers, investors, or those looking to downsize into low-maintenance living. Ideally situated in th
29 Photos
Last Updated : 2 Days ago
778 William Street, Simcoe, ON , MLS #S13764872 , Image - 1

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Unit-85, 778 William Street Midland, Simcoe, ON MLS® S13764872

Residential Condo & Other (Condo Townhouse)

$399900.0
  • 3 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Welcome to this beautifully updated 3-bedroom, 2-bathroom condo townhouse in Midland-an excellent opportunity for families, first-time buyers, or anyo
42 Photos
Last Updated : 2 Days ago
371 William Street, Simcoe, ON , MLS #S13828834 , Image - 1

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371 William Street Victoria Harbour, Tay, Simcoe, ON MLS® S13828834

Residential Freehold (Detached)

$459900.0
  • 2 Beds
  • 1 Baths
  • 1100-1500 sq-ft
Lakeside Charm Meets an Ultimate Private Backyard Oasis in Victoria Harbour! Welcome to 371 William Street, a captivating detached home offering the p
18 Photos
Last Updated : 2 Days ago
1102 Loggers Run, Simcoe, ON , MLS #S13792836 , Image - 1

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Unit-7, 1102 Loggers Run Ardagh, Barrie, Simcoe, ON MLS® S13792836

Residential Condo & Other (Condo Apartment)

$275000.0
  • 2 Beds
  • 1 Baths
  • 1000-1199 sq-ft
**OPEN HOUSE SAT SEPT 26 AT 11-1 PM** Welcome to this bright and inviting 2-storey condo townhouse in Barrie's sought-after Ardagh neighbourhood. Offe
9 Photos
Last Updated : 2 Days ago
PL 20 Concession 18 N/A W, Simcoe, ON , MLS #S13063306 , Image - 1

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PL 20 Concession 18 N/A W Rural Tiny, Tiny, Simcoe, ON MLS® S13063306

Residential Freehold (Vacant Land)

$459000.0
price drop iconPrice drop by 13.2%
  • < 700 sq-ft
Discover the perfect blend of natural beauty and privacy with this exceptional 26 plus acre parcel located near Lafontaine and Thunder Beach in the To
20 Photos
Last Updated : 2 Days ago
13 Raglan Street, Simcoe, ON , MLS #S13829354 , Image - 1

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Unit-27, 13 Raglan Street Collingwood, Simcoe, ON MLS® S13829354

Residential Condo & Other (Condo Townhouse)

$495000.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
One of Collingwood's most sought-after neighbourhoods, Sunset Point! This charming and affordable 2-bedroom, 1.5-bathroom condo offers comfortable, lo
5 Photos
Last Updated : 2 Days ago
Part 6 Cedarlane Drive, Simcoe, ON , MLS #S13829332 , Image - 1
Part 6 Cedarlane Drive Wasaga Beach, Simcoe, ON MLS® S13829332

Residential Freehold (Vacant Land)

$279900.0
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