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Houses for Sale in Simcoe Under $5 Million - P23

Showing results 661 - 690 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)
43 Photos
Last Updated : 3 Days ago
940 Nantyr Drive, Simcoe, ON , MLS #N13643372 , Image - 1
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940 Nantyr Drive Alcona, Innisfil, Simcoe, ON MLS® N13643372

Residential Freehold (Detached)

$749900.0
  • 4 Beds
  • 3 Baths
  • 1500-2000 sq-ft
Top reasons you will love this home. Premium large lot in prime location walking distance to Lake Simcoe. Large driveway with great curb appeal. Upgra
40 Photos
Last Updated : 3 Days ago
161 Forest Harbour Parkway, Simcoe, ON , MLS #S12905816 , Image - 1

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161 Forest Harbour Parkway Rural Tay, Tay, Simcoe, ON MLS® S12905816

Residential Freehold (Detached)

$741000.0
price drop iconPrice drop by 10.2%
  • 2 +2 Beds
  • 3 Baths
  • 1100-1500 sq-ft
There is a lot of house here for the money! Set on a large lot in the quiet Forest Harbour community, this 4 bedroom, 3 bathroom home offers approxima
44 Photos
Last Updated : 3 Days ago
330 Third Street, Simcoe, ON , MLS #S13044912 , Image - 1

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330 Third Street Midland, Simcoe, ON MLS® S13044912

Residential Freehold (Detached)

$439000.0
price drop iconPrice drop by 8.4%
  • 2 Beds
  • 2 Baths
  • 700-1100 sq-ft
Timeless Charm & Modern Comfort in the Heart of Midland! Welcome to a home that instantly feels just right. This beautifully updated 2-storey century
31 Photos
Last Updated : 3 Days ago
303 Broward Way, Simcoe, ON , MLS #N13094784 , Image - 1

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303 Broward Way
Unit-97, 303 Broward Way Rural Innisfil, Innisfil, Simcoe, ON MLS® N13094784

Residential Condo & Other (Condo Apartment)

$1039000.0
  • 2 Beds
  • 3 Baths
  • 1400-1599 sq-ft
Newly repositioned and offering exceptional value, this waterfront residence showcases standout views of the Marina, Centre Pier, and the sparkling wa
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
43 Photos
Last Updated : 3 Days ago
92 SANDRINGHAM Drive, Simcoe, ON , MLS #S13601698 , Image - 1

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92 SANDRINGHAM Drive Innis-Shore, Barrie, Simcoe, ON MLS® S13601698

Residential Freehold (Detached)

$799000.0
  • 2 +1 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Step inside 92 Sandringham and fall in love! This beautifully upgraded raised bungalow offers the perfect blend of style, comfort, and versatility, fe
50 Photos
Last Updated : 3 Days ago
75 Moonstone Road E, Simcoe, ON , MLS #S13652190 , Image - 1

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75 Moonstone Road E Moonstone, Oro-Medonte, Simcoe, ON MLS® S13652190

Residential Freehold (Detached)

$1549900.0
  • 4 +2 Beds
  • 5 Baths
  • 3000-3500 sq-ft
Welcome to 75 Moonstone Road East, a custom family home in Oro-Medonte where thoughtful design, exceptional space & everyday fun come together in a wa
40 Photos
Last Updated : 3 Days ago
12 Tupling Street, Simcoe, ON , MLS #N13563318 , Image - 1

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12 Tupling Street Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13563318

Residential Freehold (Detached)

$1195000.0
  • 4 Beds
  • 4 Baths
  • 2500-3000 sq-ft
Looking For a Private Backyard To Enjoy Summer Days? - Oh Yes We Have It! Welcome to Stunning 12 Tupling Street - Fully Detached 4-Bedroom Home With A
28 Photos
Last Updated : 3 Days ago
41 RUSSELL HILL Drive, Simcoe, ON , MLS #S13619534 , Image - 1

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41 RUSSELL HILL Drive Painswick South, Barrie, Simcoe, ON MLS® S13619534

Residential Freehold (Detached)

$849900.0
price drop iconPrice drop by 2.9%
  • 4 +0 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Welcome to this move-in ready family home on a premium 50-foot lot in Barrie's highly sought-after Painswick South community. Offering over 2,546 sq.
1 Photos
Last Updated : 3 Days ago
3 Tower Court, Simcoe, ON
3 Tower Court Bradford, Bradford West Gwillimbury, Simcoe, ON MLS® N13223422

Residential Freehold (Detached)

$899000.0
price drop iconPrice drop by 10.0%
  • 3 +1 Beds
  • 4 Baths
  • 1500-2000 sq-ft
Nestled on a peaceful court, Enjoy hardwood floors, 18 marble tile foyer, crown moulding, wainscoting, and natural stone accents.The modern kitchen bo
30 Photos
Last Updated : 3 Days ago
3618 Linda Street, Simcoe, ON , MLS #N13625676 , Image - 1

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3618 Linda Street Rural Innisfil, Innisfil, Simcoe, ON MLS® N13625676

Residential Freehold (Detached)

$974990.0
price drop iconPrice drop by 1.5%
  • 3 Beds
  • 3 Baths
  • 1500-2000 sq-ft
BEAUTIFUL ALL BRICK RANCH BUNGALOW STEPS FROM THE SHORES OF LAKE SIMCOE! Set on a private, treed corner lot backing onto forest, this A.N.T. built hom
40 Photos
Last Updated : 3 Days ago
1798 Emberton Way, Simcoe, ON , MLS #N12928322 , Image - 1

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1798 Emberton Way Alcona, Innisfil, Simcoe, ON MLS® N12928322

Residential Freehold (Detached)

$1168888.0
price drop iconPrice drop by 10.0%
  • 4 +1 Beds
  • 5 Baths
  • 3500-5000 sq-ft
Exceptional 6-year-old executive home featuring 3,500 sq ft of thoughtfully designed living space, complemented by a fully finished basement with a le
50 Photos
Last Updated : 3 Days ago
1521 Broderick Street, Simcoe, ON , MLS #N13072670 , Image - 1

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1521 Broderick Street Rural Innisfil, Innisfil, Simcoe, ON MLS® N13072670

Residential Freehold (Detached)

$999000.0
price drop iconPrice drop by 16.8%
  • 3 Beds
  • 3 Baths
  • 2500-3000 sq-ft
Experience luxury and privacy in Innisfil's 2,904 sq. ft. Fernbrook built Bungalow with loft. Welcome to Belle Aire Shore's Delta model elevation C f
50 Photos
Last Updated : 3 Days ago
2623 Con 10 N Nottawasaga Side Road N, Simcoe, ON , MLS #S13572766 , Image - 1

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2623 Con 10 N Nottawasaga Side Road N Rural Clearview, Clearview, Simcoe, ON MLS® S13572766

Residential Freehold (Rural Residential)

$3900000.0
price drop iconPrice drop by 13.3%
  • 3 +3 Beds
  • 4 Baths
  • 3500-5000 sq-ft
Capturing every changing views of the Niagara Escarpment from 95 breathtaking acres, this extraordinary country estate offers a rare opportunity to em
49 Photos
Last Updated : 3 Days ago
38 Sundew Drive, Simcoe, ON , MLS #S13630634 , Image - 1

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38 Sundew Drive Holly, Barrie, Simcoe, ON MLS® S13630634

Residential Freehold (Link)

$799000.0
  • 4 +2 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Welcome home to 38 Sundew Drive, an exceptional residence tucked away on a quiet street in Barrie's premier Holly community. Flooded with natural ligh
37 Photos
Last Updated : 3 Days ago
63 Dunsmore Lane, Simcoe, ON , MLS #S13638450 , Image - 1

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63 Dunsmore Lane Georgian Drive, Barrie, Simcoe, ON MLS® S13638450

Residential Freehold (Link)

$519900.0
  • 3 +0 Beds
  • 3 Baths
  • 1100-1500 sq-ft
Welcome to 63 Dunsmore Lane, a 3 bedroom linked home in Barrie's east end, an easy walk from RVH and Georgian College, zoned for Maple Grove Public Sc
36 Photos
Last Updated : 3 Days ago
375 Sea Ray Avenue, Simcoe, ON , MLS #N12891826 , Image - 1

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Unit-413, 375 Sea Ray Avenue Rural Innisfil, Innisfil, Simcoe, ON MLS® N12891826

Residential Condo & Other (Condo Apartment)

$540000.0
price drop iconPrice drop by 3.6%
  • 2 +1 Beds
  • 2 Baths
  • 800-899 sq-ft
***Move into this Luxury Relaxing Space Just In Time for Spring!*** Pinch yourself-this is the one. Welcome to a stunning penthouse residence at Frida
4 Photos
Last Updated : 3 Days ago
79 Frederick Street, Simcoe, ON , MLS #S13655208 , Image - 1
79 Frederick Street Orillia, Simcoe, ON MLS® S13655208

Residential Freehold (Detached)

$499000.0
  • 3 Beds
  • 1 Baths
  • 1100-1500 sq-ft
ESTATE SALE - A Rare Opportunity in the Heart of Historic Orillia! Offered for the first time in generations, this cherished family home was lovingly
46 Photos
Last Updated : 3 Days ago
41 Durham Avenue, Simcoe, ON , MLS #S13468682 , Image - 1

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41 Durham Avenue Rural Barrie Southeast, Barrie, Simcoe, ON MLS® S13468682

Residential Freehold (Detached)

$799999.0
price drop iconPrice drop by 2.4%
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Welcome to this stunning 2-storey Georgian model by Tiffany Homes in vibrant Barrie! Tucked into a sought-after neighbourhood just minutes from the Ba
30 Photos
Last Updated : 3 Days ago
1230 Grandview Lodge Road, Simcoe, ON , MLS #S13563974 , Image - 1

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Unit-F, 1230 Grandview Lodge Road Rural Severn, Severn, Simcoe, ON MLS® S13563974

Residential Condo & Other (Other)

$439900.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Experience captivating waterfront living at this beautifully renovated 2-bedroom, 2-bathroom cottage that sleeps 8 on the historic Trent-Severn Waterw
25 Photos
Last Updated : 3 Days ago
1386 Sheldon Street, Simcoe, ON , MLS #N13554880 , Image - 1

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1386 Sheldon Street Alcona, Innisfil, Simcoe, ON MLS® N13554880

Residential Freehold (Detached)

$919900.0
price drop iconPrice drop by 3.2%
  • 4 Beds
  • 3 Baths
  • 2000-2500 sq-ft
Absolutely stunning custom-renovated dream home situated in one of Innisfil's most desirable locations. Boasting incredible curb appeal, this property
49 Photos
Last Updated : 3 Days ago
4169 Lavis Lane, Simcoe, ON , MLS #S13541670 , Image - 1

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4169 Lavis Lane Rural Severn, Severn, Simcoe, ON MLS® S13541670

Residential Freehold (Detached)

$999000.0
price drop iconPrice drop by 16.7%
  • 5 Beds
  • 2 Baths
  • 1500-2000 sq-ft
TEA LAKE***Amazing Swimming Rock off The Front of 216ft of Prime Muskoka Rock all across The Waterfront Situated and Private on an Expansive, Heavily
36 Photos
Last Updated : 3 Days ago
8061 Main Street, Simcoe, ON , MLS #N13508274 , Image - 1

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8061 Main Street Everett, Adjala-Tosorontio, Simcoe, ON MLS® N13508274

Residential Freehold (Detached)

$695000.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Your private forest escape, hiding in plain sight. Step onto your covered front porch with coffee in hand, surrounded by mature trees that have stood
34 Photos
Last Updated : 3 Days ago
121 Green Briar Road, Simcoe, ON , MLS #N13597110 , Image - 1

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Unit-16, 121 Green Briar Road Rural New Tecumseth, New Tecumseth, Simcoe, ON MLS® N13597110

Residential Condo & Other (Semi-Detached Condo)

$474900.0
price drop iconPrice drop by 5.0%
  • 2 +1 Beds
  • 2 Baths
  • 1000-1199 sq-ft
Welcome To This Charming 2+1 Bedroom, 2 Bathroom Semi-Detached Bungalow Situated On A Desirable Corner Lot In The Highly Sought-After Green Briar Comm
12 Photos
Last Updated : 3 Days ago
816 Jane Boulevard, Simcoe, ON , MLS #S13607774 , Image - 1

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816 Jane Boulevard Midland, Simcoe, ON MLS® S13607774

Residential Condo & Other (Condo Townhouse)

$475000.0
  • 2 Beds
  • 2 Baths
  • 1000-1199 sq-ft
THOUGHTFULLY UPDATED BUNGALOW STEPS FROM LITTLE LAKE! What if homeownership came with more freedom? Ditch the lawnmower and snow shovel for this beaut
48 Photos
Last Updated : 3 Days ago
245 Jane Street, Simcoe, ON , MLS #S13532262 , Image - 1

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245 Jane Street Stayner, Clearview, Simcoe, ON MLS® S13532262

Residential Freehold (Detached)

$1149000.0
  • 5 Beds
  • 5 Baths
  • 3000-3500 sq-ft
Exceptional legal duplex offering the perfect blend of family living and investment potential. The bright, open-concept main home features 3 spacious
26 Photos
Last Updated : 3 Days ago
2910 MacLean Lake North Shore Road, Simcoe, ON , MLS #S13176514 , Image - 1

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2910 MacLean Lake North Shore Road Rural Severn, Severn, Simcoe, ON MLS® S13176514

Residential Freehold (Detached)

$889000.0
  • 2 Beds
  • 1 Baths
  • < 700 sq-ft
MACLEAN LAKE OF GLOUCESTER POOL This Property is all about The View, The Privacy, & The Waterfront Lifestyle. Offering 230 feet of Pristine Natural Sh
50 Photos
Last Updated : 3 Days ago
243 Harvey Street W, Simcoe, ON , MLS #S13522568 , Image - 1

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243 Harvey Street W Orillia, Simcoe, ON MLS® S13522568

Residential Freehold (Detached)

$297500.0
price drop iconPrice drop by 20.7%
  • 2 Beds
  • 1 Baths
  • 700-1100 sq-ft
NEW LOW PRICE!! IT'S GOT TO GO. SELLER PURCHASED ! Welcome to 243 Harvey Street, a rare Orillia opportunity offering an expansive Estate 60' x 176' l
50 Photos
Last Updated : 3 Days ago
1072 Wickham Road, Simcoe, ON , MLS #N13512342 , Image - 1

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1072 Wickham Road Rural Innisfil, Innisfil, Simcoe, ON MLS® N13512342

Residential Freehold (Detached)

$1179000.0
  • 4 +1 Beds
  • 5 Baths
  • 3500-5000 sq-ft
Welcome to this stunning, fully upgraded 4-bedrms, 5-baths home in the prestigious, family-oriented neighbourhood. RARE FIND FOR BUYERS WHO VALUE SPAC
44 Photos
Last Updated : 3 Days ago
41 Treetops Boulevard, Simcoe, ON , MLS #N13521368 , Image - 1

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41 Treetops Boulevard Alliston, New Tecumseth, Simcoe, ON MLS® N13521368

Residential Freehold (Detached)

$999000.0
  • 3 +1 Beds
  • 4 Baths
  • 2000-2500 sq-ft
Sun-filled 3+1 bedroom + office home fronting a park in Treetops and giving you flexible 3 + 1 bedroom + office living. Over 3,000 sq ft of living spa
39 Photos
Last Updated : 3 Days ago
51 Lakeside Drive, Simcoe, ON , MLS #N13542196 , Image - 1

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51 Lakeside Drive Rural Innisfil, Innisfil, Simcoe, ON MLS® N13542196

Residential Freehold (Detached)

$698000.0
  • 3 Beds
  • 2 Baths
  • 1100-1500 sq-ft
Welcome to this beautifully and professionally upgraded home located right across from Lake Simcoe/Kempenfelt Bay with remarkable lake views! Enjoy be
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