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Houses for Sale in Simcoe Under $5 Million - P44

Showing results 1291 - 1320 of 5140
Last Updated: August 12, 2026
  • New Listings
  • Price(Lo-Hi)
  • Price(Hi-Lo)
  • Bedrooms(Hi-Lo)
  • Bathrooms(Hi-Lo)
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  • Square Feet(Hi-Lo)
35 Photos
Last Updated : 6 Days ago
86 Trillium Crescent, Simcoe, ON , MLS #S13641180 , Image - 1
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86 Trillium Crescent Allandale Heights, Barrie, Simcoe, ON MLS® S13641180

Residential Freehold (Detached)

$649900.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Welcome to 86 Trillium Crescent - a fantastic opportunity in one of Barrie's most convenient family-friendly neighbourhoods! This charming 2-storey ho
29 Photos
Last Updated : 6 Days ago
2 Wasaga Pines Lane E, Simcoe, ON , MLS #S13080762 , Image - 1

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2 Wasaga Pines Lane E Elmvale, Springwater, Simcoe, ON MLS® S13080762

Residential Freehold (MobileTrailer)

$115000.0
price drop iconPrice drop by 18.6%
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Welcome to Wasaga Pines, with Seasonal Site six (6) months occupancy. This recreational lifestyle includes shared us of 2 pools, playground, volleyba
20 Photos
Last Updated : 6 Days ago
1048 Sylvan Glen Drive, Simcoe, ON , MLS #S13573098 , Image - 1

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1048 Sylvan Glen Drive Brechin, Ramara, Simcoe, ON MLS® S13573098

Residential Freehold (Detached)

$675000.0
price drop iconPrice drop by 2.2%
  • 3 Beds
  • 1 Baths
  • 700-1100 sq-ft
Visit REALTOR website for additional information. Fabulous four season, 3 bedroom waterfront home on Lake Dalrymple near Brechin ON. Perfect for year
50 Photos
Last Updated : 6 Days ago
1512 Champlain Road, Simcoe, ON , MLS #S13526650 , Image - 1

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1512 Champlain Road Rural Tiny, Tiny, Simcoe, ON MLS® S13526650

Residential Freehold (Detached)

$725000.0
price drop iconPrice drop by 3.3%
  • 5 Beds
  • 2 Baths
  • 2500-3000 sq-ft
STEPS FROM WATERFRONT ACCESS TO GEORGIAN BAY! Welcome to this stunning 5-bedroom, 2-bathroom property with breathtaking views of Georgian Bay. Situate
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
45 Photos
Last Updated : 6 Days ago
14 & 16 Fletcher Street, Simcoe, ON , MLS #N13636236 , Image - 1

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14 & 16 Fletcher Street Alliston, New Tecumseth, Simcoe, ON MLS® N13636236

Residential Freehold (Duplex)

$949000.0
  • 6 Beds
  • 2 Baths
  • 1500-2000 sq-ft
This well-maintained legal duplex offers incredible flexibility for investors, multi-generational families, or buyers looking to offset their mortgage
20 Photos
Last Updated : 6 Days ago
6 Rosemarie Drive, Simcoe, ON , MLS #S13640898 , Image - 1

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6 Rosemarie Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13640898

Residential Freehold (Detached)

$819900.0
  • 3 +1 Beds
  • 1 Baths
  • 1100-1500 sq-ft
THE UPDATES ARE DONE, THE DECK IS CALLING & THE REC ROOM HAS SPACE FOR EVERYONE! Set on a generous 97 x 135 ft lot in a quiet neighbourhood near Lake
41 Photos
Last Updated : 6 Days ago
11 Pinetree Drive, Simcoe, ON , MLS #S13535282 , Image - 1

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11 Pinetree Drive Rural Oro-Medonte, Oro-Medonte, Simcoe, ON MLS® S13535282

Residential Freehold (Detached)

$1473900.0
  • 4 Beds
  • 5 Baths
  • 3500-5000 sq-ft
Welcome to your home at Eagles' Rest Estates - an exclusive luxury enclave of private estate homes, surrounded by lush, majestic greenery. Enjoy appro
34 Photos
Last Updated : 6 Days ago
84 Mississaga Street W, Simcoe, ON , MLS #S13571966 , Image - 1

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84 Mississaga Street W Orillia, Simcoe, ON MLS® S13571966

Residential Freehold (Fourplex)

$825000.0
  • 6 Beds
  • 4 Baths
  • 3500-5000 sq-ft
Downtown Orillia, Legal Fourplex, has been continually upgraded, offering great income producing potential. Secure an income-focused legal fourplex in
26 Photos
Last Updated : 6 Days ago
1152 Stoney Point Road, Simcoe, ON , MLS #N13640926 , Image - 1

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1152 Stoney Point Road Rural Innisfil, Innisfil, Simcoe, ON MLS® N13640926

Residential Freehold (Detached)

$574000.0
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
Tucked away on a quiet, private road with exclusive resident-only boat launch access, this exceptional property offers the ultimate lakeside lifestyle
47 Photos
Last Updated : 6 Days ago
164 Webb Street, Simcoe, ON , MLS #N13147832 , Image - 1

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164 Webb Street Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13147832

Residential Freehold (Detached)

$964900.0
price drop iconPrice drop by 3.0%
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Welcome to this beautifully upgraded, move-in ready home located in one of Bradford's most sought-after communities. Situated on a pool size lot, this
45 Photos
Last Updated : 6 Days ago
303 Sunnybrae Avenue, Simcoe, ON , MLS #N13571016 , Image - 1

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303 Sunnybrae Avenue Stroud, Innisfil, Simcoe, ON MLS® N13571016

Residential Freehold (Detached)

$1799999.0
  • 5 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Welcome to 303 Sunnybrae Avenue, A Truly One-Of-A-Kind Custom Home In Prestigious Innisfil Estates. Set On A Private Half-Acre Lot With No Neighbours
43 Photos
Last Updated : 6 Days ago
3371 Lake St. George Boulevard, Simcoe, ON , MLS #S13576368 , Image - 1

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3371 Lake St. George Boulevard Rural Severn, Severn, Simcoe, ON MLS® S13576368

Residential Freehold (Detached)

$1499900.0
  • 3 +2 Beds
  • 4 Baths
  • 1500-2000 sq-ft
Check this out!!! 130 ft of sandy beach, with just under an acre of land on Lake St George, ideal for swimming, water sports & fishing!! Private, gate
10 Photos
Last Updated : 6 Days ago
46 Beck Boulevard, Simcoe, ON , MLS #S12983150 , Image - 1

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46 Beck Boulevard Penetanguishene, Simcoe, ON MLS® S12983150

Residential Freehold (Vacant Land)

$524900.0
price drop iconPrice drop by 19.2%
HERE'S WHY 46 BECK BLVD COULD BE YOUR NEXT MOVE: ***89 FT OF WATERFRONT*** Direct access to Georgian Bay for paddling, boating, or an evening float. T
2 Photos
Last Updated : 6 Days ago
781-4 Katrina Street, Simcoe, ON , MLS #S13028044 , Image - 1
781-4 Katrina Street Wasaga Beach, Simcoe, ON MLS® S13028044

Residential Freehold (Att/Row/Townhouse)

$548664.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
New HST Rebate Pricing! To Be Built (Fall 2027) - Located in the Brightside community with walking distance to Wasaga Beach public school and future h
2 Photos
Last Updated : 6 Days ago
782-3 Katrina Street, Simcoe, ON , MLS #S13028046 , Image - 1
782-3 Katrina Street Wasaga Beach, Simcoe, ON MLS® S13028046

Residential Freehold (Att/Row/Townhouse)

$534504.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
New HST Rebate Pricing! To Be Built (Fall 2027) - Welcome to Brightside in the River's Edge community. This 'Thrill' floor plan offers 1,688 sq ft wit
50 Photos
Last Updated : 6 Days ago
30 Fisher Drive, Simcoe, ON , MLS #N13640778 , Image - 1

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30 Fisher Drive Everett, Adjala-Tosorontio, Simcoe, ON MLS® N13640778

Residential Freehold (Detached)

$1225000.0
  • 3 +2 Beds
  • 4 Baths
  • 1500-2000 sq-ft
Top 5 Reasons You Will Love This Home: 1) Elegant custom-built bungalow nestled within a mature neighbourhood, offering a peaceful, established settin
2 Photos
Last Updated : 6 Days ago
783-2 Katrina Street, Simcoe, ON , MLS #S13028052 , Image - 1
783-2 Katrina Street Wasaga Beach, Simcoe, ON MLS® S13028052

Residential Freehold (Att/Row/Townhouse)

$499106.0
  • 3 Beds
  • 2 Baths
  • 1500-2000 sq-ft
New HST Rebate Pricing! To Be Built (Fall 2027) - Affordable living in the Brightside at River's Edge community. The 'Cheer' townhouse provides 3 bedr
2 Photos
Last Updated : 6 Days ago
710R Katrina Street, Simcoe, ON , MLS #S13028054 , Image - 1
710R Katrina Street Wasaga Beach, Simcoe, ON MLS® S13028054

Residential Freehold (Detached)

$587602.0
  • 2 Beds
  • 3 Baths
  • 1500-2000 sq-ft
New HST Rebate Pricing! To Be Built (Fall 2027) - Welcome to bungalow living in the beautiful Brightside by River's Edge community. Walking distance t
2 Photos
Last Updated : 6 Days ago
711L Katrina Street, Simcoe, ON , MLS #S13028058 , Image - 1
711L Katrina Street Wasaga Beach, Simcoe, ON MLS® S13028058

Residential Freehold (Detached)

$614150.0
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
New HST Rebate Pricing! To Be Built (Fall 2027) - Welcome to Brightside in the River's Edge community. This 'Vivid' floor plan offers 1,798sq ft with
2 Photos
Last Updated : 6 Days ago
712R Katrina Street, Simcoe, ON , MLS #S13028060 , Image - 1
712R Katrina Street Wasaga Beach, Simcoe, ON MLS® S13028060

Residential Freehold (Detached)

$649549.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
New HST Rebate Pricing! To Be Built (Fall 2027) - The 'Luster' is a spacious floor plan with 4 bedrooms, 2.5 bathrooms and 2,109 sq ft. Main floor inc
41 Photos
Last Updated : 6 Days ago
3448 CORONATION Avenue, Simcoe, ON , MLS #S13640744 , Image - 1

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3448 CORONATION Avenue West Shore, Severn, Simcoe, ON MLS® S13640744

Residential Freehold (Detached)

$549900.0
  • 2 +1 Beds
  • 2 Baths
  • 700-1100 sq-ft
Set on an impressive 150x50 ft lot in Cumberland Beach, this well maintained raised bungalow offers more than 1,350 sq. ft. of finished living space
44 Photos
Last Updated : 6 Days ago
65 Ellen Street, Simcoe, ON , MLS #S13640736 , Image - 1

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Unit-1104, 65 Ellen Street City Centre, Barrie, Simcoe, ON MLS® S13640736

Residential Condo & Other (Condo Apartment)

$800000.0
  • 2 Beds
  • 2 Baths
  • 1200-1399 sq-ft
There are waterfront condominiums with a view... and then there are the ones people remember long after someone else buys them. Welcome to one of Barr
20 Photos
Last Updated : 6 Days ago
83 Shelburne Avenue, Simcoe, ON , MLS #S13514750 , Image - 1

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83 Shelburne Avenue Wasaga Beach, Simcoe, ON MLS® S13514750

Residential Freehold (Att/Row/Townhouse)

$539900.0
  • 3 +1 Beds
  • 4 Baths
  • 1500-2000 sq-ft
Imagine waking up in your own home, breathing in fresh Georgian Bay air, just minutes from the beach...Welcome to Georgian Sands - a beautiful opportu
50 Photos
Last Updated : 6 Days ago
32 Reynolds Lane, Simcoe, ON , MLS #S13637852 , Image - 1

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32 Reynolds Lane Edgehill Drive, Barrie, Simcoe, ON MLS® S13637852

Residential Freehold (Detached)

$1200000.0
  • 4 +2 Beds
  • 4 Baths
  • 3000-3500 sq-ft
Welcome to this spacious detached home in Barrie on a massive pie shaped lot opening up to 100 ft wide in the back, offering a functional layout with
29 Photos
Last Updated : 6 Days ago
2150 Speare Court, Simcoe, ON , MLS #N13616044 , Image - 1

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2150 Speare Court Rural Innisfil, Innisfil, Simcoe, ON MLS® N13616044

Residential Freehold (Att/Row/Townhouse)

$868000.0
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Welcome to 2150 Speare Crt, this exceptional freehold end-unit townhome in the highly desirable Alcona Shores community of Innisfil. Offering 2,434 sq
38 Photos
Last Updated : 6 Days ago
1775 Loretta Avenue, Simcoe, ON , MLS #S13576854 , Image - 1

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1775 Loretta Avenue Rural Severn, Severn, Simcoe, ON MLS® S13576854

Residential Freehold (Detached)

$1048800.0
  • 3 Beds
  • 2 Baths
  • 2000-2500 sq-ft
Truly one of Severn's BEST VALUE! Experience the perfect blend of privacy, space, and lifestyle in this 3-bedroom detached bungalow featuring a 3-car
47 Photos
Last Updated : 6 Days ago
73 Pepler Place, Simcoe, ON , MLS #S13052504 , Image - 1

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73 Pepler Place Sunnidale, Barrie, Simcoe, ON MLS® S13052504

Residential Freehold (Detached)

$699000.0
price drop iconPrice drop by 6.7%
  • 2 +2 Beds
  • 2 Baths
  • 700-1100 sq-ft
All-Brick Four-Level Backsplit Showcasing Exceptional Pride of Ownership! Welcome to 73 Pepler Place-an ideal family home tucked away on a quiet stree
21 Photos
Last Updated : 6 Days ago
21 Pearcey Crescent, Simcoe, ON , MLS #S13568418 , Image - 1

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21 Pearcey Crescent West Bayfield, Barrie, Simcoe, ON MLS® S13568418

Residential Freehold (Att/Row/Townhouse)

$579900.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Built In 2013, This Beautifully Maintained & Move-In Ready Townhome Offers The Perfect Blend Of Modern Design, Functional Living & An Unbeatable Locat
41 Photos
Last Updated : 6 Days ago
404 Manly Street, Simcoe, ON , MLS #S13640472 , Image - 1

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404 Manly Street Midland, Simcoe, ON MLS® S13640472

Residential Freehold (Detached)

$665000.0
  • 4 Beds
  • 3 Baths
  • 2500-3000 sq-ft
RARE 3-STOREY CENTURY HOME SHOWCASING TIMELESS CURB APPEAL & A PRIVATE BACKYARD OASIS COMPLETE WITH AN INGROUND POOL! Welcome to this beautifully main
31 Photos
Last Updated : 6 Days ago
2811 Stephen Drive, Simcoe, ON , MLS #S13631208 , Image - 1

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2811 Stephen Drive Rural Ramara, Ramara, Simcoe, ON MLS® S13631208

Residential Freehold (Detached)

$749649.0
  • 2 +1 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Client RemarksBeautiful 3 Bedroom Bungalow Situated In The Community of Mara Shores Within Walking Distance to Neighbourhood Private Park on Lake Simc
Shortlisted Properties
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