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Houses for Sale in Simcoe Under $5 Million - P35

Showing results 1021 - 1050 of 5157
Last Updated: September 26, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
  • Square Feet(Lo-Hi)
  • Square Feet(Hi-Lo)
22 Photos
Last Updated : 4 Days ago
121 Mary Street, Simcoe, ON , MLS #S13813678 , Image - 1
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Unit-314, 121 Mary Street Creemore, Clearview, Simcoe, ON MLS® S13813678

Residential Condo & Other (Condo Apartment)

$359000.0
  • 1 +1 Beds
  • 1 Baths
  • 700-799 sq-ft
Enjoy seamless, turnkey living at The Brix in Creemore --- ideal for any stage of life. This move-in ready One plus Den suite features 9-foot ceilings
29 Photos
Last Updated : 4 Days ago
65 Pearl Drive, Simcoe, ON , MLS #S13813638 , Image - 1

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65 Pearl Drive Orillia, Simcoe, ON MLS® S13813638

Residential Freehold (Detached)

$629900.0
  • 4 Beds
  • 3 Baths
  • 1500-2000 sq-ft
If you've been waiting for the right house in the right location, 65 Pearl belongs at the top of your list. There's plenty of room to spread out, a la
24 Photos
Last Updated : 4 Days ago
71 Gibbard Crescent, Simcoe, ON , MLS #S13588594 , Image - 1

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71 Gibbard Crescent Collingwood, Simcoe, ON MLS® S13588594

Residential Freehold (Semi-Detached )

$499000.0
price drop iconPrice drop by 3.9%
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Bright and fresh -- ready for you and your family. This is a two storey semi-detached with three bedrooms on the upper level and living room, kitchen
35 Photos
Last Updated : 4 Days ago
16 Austen Lane, Simcoe, ON , MLS #S13525564 , Image - 1

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16 Austen Lane Letitia Heights, Barrie, Simcoe, ON MLS® S13525564

Residential Freehold (Detached)

$549900.0
price drop iconPrice drop by 4.3%
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to 16 Austen Lane! Situated in Barrie's established Letitia Heights neighbourhood, this well-maintained 4-level back split offers a functional
Open House : Sun Sep 27, 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
8 Photos
Last Updated : 4 Days ago
11 Beck Boulevard, Simcoe, ON , MLS #S13809306 , Image - 1

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Unit-102, 11 Beck Boulevard Penetanguishene, Simcoe, ON MLS® S13809306

Residential Condo & Other (Condo Apartment)

$439000.0
  • 1 Beds
  • 1 Baths
  • 800-899 sq-ft
Private, Enjoyable Suite With Interesting Sight Lines, Garage Parking, Plus A Locker For Your Additional Storage Needs! Here you have full advantage o
5 Photos
Last Updated : 4 Days ago
1361 Rimkey Crescent, Simcoe, ON , MLS #S13720294 , Image - 1
1361 Rimkey Crescent Rural Severn, Severn, Simcoe, ON MLS® S13720294

Residential Freehold (Detached)

$1398000.0
price drop iconPrice drop by 4.2%
  • 3 +1 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Custom-built estate home, offering approximately 2,000 square feet of custom-designed living space plus a full unfinished basement with rough-in plumb
6 Photos
Last Updated : 4 Days ago
Lot 2 (R) Street B N/A, Simcoe, ON , MLS #N13810670 , Image - 1

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Lot 2 (R) Street B N/A Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13810670

Residential Freehold (Semi-Detached )

$779900.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
WELCOME TO THE MILANO - a beautifully designed all-brick 1534 sq.ft. semi-detached home in Tuscan Enclave, a newly released FREEHOLD community in Brad
36 Photos
Last Updated : 4 Days ago
3 Honeysuckle Lane, Simcoe, ON , MLS #N13683312 , Image - 1

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3 Honeysuckle Lane Rural Innisfil, Innisfil, Simcoe, ON MLS® N13683312

Residential Freehold (Modular Home)

$379000.0
  • 2 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Set on a quiet dead-end street in the north end of Sandy Cove Acres, this updated Monaco model combines a private-feeling lot with the convenience of
27 Photos
Last Updated : 4 Days ago
30 Periwinkle Road, Simcoe, ON , MLS #S13813538 , Image - 1

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30 Periwinkle Road Midhurst, Springwater, Simcoe, ON MLS® S13813538

Residential Freehold (Semi-Detached )

$739000.0
  • 4 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Priced for quick sale, this beautiful well maintained semi detached home with 2020 sq. ft. of above grade living space features 9 ceiling on main floo
34 Photos
Last Updated : 4 Days ago
360 Blake Street NW, Simcoe, ON , MLS #S13633042 , Image - 1

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Unit-24, 360 Blake Street NW Codrington, Barrie, Simcoe, ON MLS® S13633042

Residential Condo & Other (Condo Townhouse)

$480000.0
price drop iconPrice drop by 3.8%
  • 3 Beds
  • 2 Baths
  • 1200-1399 sq-ft
Welcome home! With over 1750 finished square feet this extremely spacious and beautifully maintained, move in ready, end unit townhome is a must see.
37 Photos
Last Updated : 4 Days ago
224 Foster Drive, Simcoe, ON , MLS #S13740594 , Image - 1

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224 Foster Drive Painswick North, Barrie, Simcoe, ON MLS® S13740594

Residential Freehold (Detached)

$604900.0
price drop iconPrice drop by 3.2%
  • 2 +1 Beds
  • 1 Baths
  • 700-1100 sq-ft
WELCOME TO 224 FOSTER DRIVE! THIS PROPERTY PRESENTS AN EXCELLENT INVESTMENT OPPORTUNITY, AS WELL AS A PRIVATE FAMILY HOME. SITUATED ON A 300 FOOT DEEP
43 Photos
Last Updated : 4 Days ago
7602 25th Sideroad N/A, Simcoe, ON , MLS #N13756938 , Image - 1

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7602 25th Sideroad N/A Rural Adjala-Tosorontio, Adjala-Tosorontio, Simcoe, ON MLS® N13756938

Residential Freehold (Detached)

$699000.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Escape the hustle and discover a peaceful country retreat just minutes from Alliston. Nestled on approximately 3 private acres along a quiet country r
Open House : Sun Sep 27, 12:00 PM to 02:00 PM
50 Photos
Last Updated : 4 Days ago
2249 Willard Avenue, Simcoe, ON , MLS #N13727878 , Image - 1

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2249 Willard Avenue Alcona, Innisfil, Simcoe, ON MLS® N13727878

Residential Freehold (Detached)

$884900.0
  • 3 +1 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Newly Renovated move in ready home with over $200,000 in upgrades and renovations throughout the home and the backyard with its very own resort like o
Open House : Sun Sep 27, 01:00 PM to 03:00 PM
43 Photos
Last Updated : 4 Days ago
8 Rogers Trail, Simcoe, ON , MLS #N13795160 , Image - 1

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8 Rogers Trail Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13795160

Residential Freehold (Att/Row/Townhouse)

$799900.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome to this bright and beautifully designed freehold townhome offering almost 2,000 sq. ft. of living space, nestled on a quiet, family-friendly s
Open House : Sat Sep 26, 01:00 PM to 03:00 PM
49 Photos
Last Updated : 4 Days ago
7 ORSI Drive, Simcoe, ON , MLS #S13813466 , Image - 1

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7 ORSI Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13813466

Residential Freehold (Detached)

$1199900.0
  • 3 +1 Beds
  • 3 Baths
  • 1500-2000 sq-ft
It's not often you find this much space and privacy this close to Orillia. Tucked into the small community of Bass Lake Heights on a beautifully lands
50 Photos
Last Updated : 4 Days ago
22 Baycrest Drive, Simcoe, ON , MLS #S13813438 , Image - 1

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22 Baycrest Drive North Shore, Barrie, Simcoe, ON MLS® S13813438

Residential Freehold (Detached)

$1699000.0
  • 2 +2 Beds
  • 3 Baths
  • 1500-2000 sq-ft
A rare North Shore opportunity where an unbeatable location, waterfront lifestyle, and exciting future potential come together! Set on a rare DOUBLE L
36 Photos
Last Updated : 4 Days ago
6776 County Road 10 N/A, Simcoe, ON , MLS #N13808200 , Image - 1

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6776 County Road 10 N/A Rural Essa, Essa, Simcoe, ON MLS® N13808200

Residential Freehold (Detached)

$999000.0
  • 3 +1 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome Home! This amazing 3-bedroom, 3-bath home offers the perfect blend of country living on just under an acre lot and modern updates, including a
Open House : Sat Sep 26, 01:00 PM to 03:00 PM
34 Photos
Last Updated : 4 Days ago
1764 Bay Park Road, Simcoe, ON , MLS #S13694004 , Image - 1

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1764 Bay Park Road Rural Severn, Severn, Simcoe, ON MLS® S13694004

Residential Freehold (Detached)

$1249888.0
  • 4 Beds
  • 1 Baths
  • 1500-2000 sq-ft
A Once-in-a-generation Opportunity To Own An Extraordinary Lakefront Estate On Lake Couchiching. Boasting More Than 400 Feet Of Pristine Shoreline, Th
16 Photos
Last Updated : 4 Days ago
2458 South Orr Lake Road, Simcoe, ON , MLS #S13794988 , Image - 1

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2458 South Orr Lake Road Rural Springwater, Springwater, Simcoe, ON MLS® S13794988

Residential Freehold (Detached)

$639888.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
A Unique Opportunity On The Shores Of Orr Lake Offering Approximately 1.2 Acres With Approx. 114 Feet Of Direct Waterfront And A Deep, Approximately 1
20 Photos
Last Updated : 4 Days ago
38 Chaucer Crescent, Simcoe, ON , MLS #S13653326 , Image - 1

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38 Chaucer Crescent Letitia Heights, Barrie, Simcoe, ON MLS® S13653326

Residential Freehold (Att/Row/Townhouse)

$489888.0
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Spacious And Well-situated Townhome At 38 Chaucer Crescent Offering A Fantastic Opportunity For Buyers And Investors Alike. Bright Living Areas Featur
45 Photos
Last Updated : 4 Days ago
15 Byers Street, Simcoe, ON , MLS #S13748160 , Image - 1

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15 Byers Street Snow Valley, Springwater, Simcoe, ON MLS® S13748160

Residential Freehold (Detached)

$1925888.0
  • 3 +2 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Perfectly Located In One Of Springwater's Most Prestigious And Sought-after Neighbourhoods, This Stunning Modern Bungalow Offers Upscale Living With A
6 Photos
Last Updated : 4 Days ago
1644 Ridge Road E, Simcoe, ON , MLS #S13750798 , Image - 1

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Unit-Vacant Land, 1644 Ridge Road E Hawkestone, Oro-Medonte, Simcoe, ON MLS® S13750798

Residential Freehold (Vacant Land)

$249888.0
This Is A Rare Opportunity To Design A Custom Home That Reflects Your Vision And Lifestyle On A Beautiful 1.06-Acre Treed Building Lot In The Welcomin
32 Photos
Last Updated : 4 Days ago
1644 Ridge Road E, Simcoe, ON , MLS #S13750904 , Image - 1

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1644 Ridge Road E Hawkestone, Oro-Medonte, Simcoe, ON MLS® S13750904

Residential Freehold (Detached)

$769888.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Imagine Coming Home To A Peaceful Country Setting Where Mature Trees Surround You, Neighbours Still Wave As They Pass By, And Life Moves At A More Com
50 Photos
Last Updated : 4 Days ago
20 Speirs Road, Simcoe, ON , MLS #S13797606 , Image - 1

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20 Speirs Road Holly, Barrie, Simcoe, ON MLS® S13797606

Residential Freehold (Detached)

$899900.0
  • 4 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Stunning Curb Appeal, A Prime Setting On The Street And Beautifully Landscaped Make This Holly Home A Standout. Pride Of Ownership Throughout By Its O
Open House : Sun Sep 27, 12:00 PM to 03:00 PM
45 Photos
Last Updated : 4 Days ago
32 Carter Crescent, Simcoe, ON , MLS #S13810230 , Image - 1

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32 Carter Crescent Orillia, Simcoe, ON MLS® S13810230

Residential Freehold (Detached)

$745000.0
  • 2 +2 Beds
  • 2 Baths
  • 700-1100 sq-ft
Well-kept, all-brick bungalow in Orillia's sought-after Rynard Estates, offering a comfortable floor plan, generous finished living space and a privat
50 Photos
Last Updated : 4 Days ago
6 Alyssa Drive, Simcoe, ON , MLS #S13176562 , Image - 1

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6 Alyssa Drive Collingwood, Simcoe, ON MLS® S13176562

Residential Freehold (Detached)

$829000.0
price drop iconPrice drop by 7.8%
  • 3 Beds
  • 4 Baths
  • 1500-2000 sq-ft
Fabulous home in the very desirable & much sought after Georgian Meadows. This spacious 3 Bed 4 Bath property is ready to welcome its new owners. Whe
50 Photos
Last Updated : 4 Days ago
1025 Maclean Street, Simcoe, ON , MLS #N13809902 , Image - 1

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1025 Maclean Street Alcona, Innisfil, Simcoe, ON MLS® N13809902

Residential Freehold (Detached)

$679000.0
  • 3 Beds
  • 2 Baths
  • 1500-2000 sq-ft
Welcome home to 1025 Maclean Street, a beautifully maintained 3-bedroom, 2-bathroom family home in a sought-after Innisfil neighbourhood, offering app
44 Photos
Last Updated : 4 Days ago
17 CROMPTON Drive, Simcoe, ON , MLS #S13762408 , Image - 1

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17 CROMPTON Drive Little Lake, Barrie, Simcoe, ON MLS® S13762408

Residential Freehold (Detached)

$834888.0
  • 3 +2 Beds
  • 4 Baths
  • 2000-2500 sq-ft
This spectacular John Davies-built turnkey home in the esteemed Country Club Estates checks every single box for a growing family, offering over 3,000
47 Photos
Last Updated : 4 Days ago
2032 Chantler Street, Simcoe, ON , MLS #N13813290 , Image - 1

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2032 Chantler Street Stroud, Innisfil, Simcoe, ON MLS® N13813290

Residential Freehold (Detached)

$1124900.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Top 5 Reasons You Will Love This Home: 1) Enjoy peace of mind with major updates, including a new roof, furnace, central air conditioner, most windows
49 Photos
Last Updated : 4 Days ago
5 Grouse Glen, Simcoe, ON , MLS #S13772520 , Image - 1

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5 Grouse Glen Ardagh, Barrie, Simcoe, ON MLS® S13772520

Residential Freehold (Detached)

$1149900.0
  • 3 +1 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Beautifully renovated and thoughtfully upgraded, this move-in-ready home is ideally situated in sought-after Ardagh Bluffs. Poised on a mature lot wit
Open House : Sat Sep 26, 11:00 AM to 01:00 PM
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